On today’s episode of Startups For The Rest of Us, Rob Walling (@robwalling) talks with David Newell (@davidsnewell), a Senior Advisor at Quiet Light Brokerage, about the dos and dont’s of SaaS valuations.
The topics we cover
- 4:12 Running your business as if it were a sellable asset
- 5:15 Quiet Light deal count and other stats
- 8:53 SaaS valuations today and how SDE valuations work
- 17:50 How revenue valuations work
- 21:19 David Newell shares stories of dos and donts of valuations
- 29:52 What do the best buyers do?
Links from the show
- Quiet Light
- Resources for Buying and Selling Online Businesses
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Rob: Welcome to this week’s episode of Startups for the Rest of Us. I’m your host, Rob Walling. This week, I have a conversation with an M&A advisor named David Newell. David is a Senior Advisor at Quiet Light. According to his bio, he’s an industry expert in evaluation and sale of SaaS businesses. He’s a former investment banker at Citi which he did for three years before moving into the online business space.
He’s advised on the sale of several well-known bootstrapped B2B apps including in the sale of Drip back when he worked for FE International. He also helped with sale of apps like LessAccounting, Sifter, Codetree, and HitTail as well, which is another one that I had sold through FE back when David worked with them.
I’ve known David for several years. I met him at a few conferences. I believe he was at Rhodium Weekend, Chris Yates’ event in Vegas years ago. David just has a lot of experience on the sales side and also working with buyers of SaaS apps.
In our conversation, we talk about what valuations look like today and it’s fun because I threw out my rules of thumb and he says, “I think they’re a little bit richer.” He said, “I think they’ve gone up. It’s a little hotter.” My valuations were probably from (let’s say) 2–3 years ago and that’s the beauty of SaaS. It just keeps going up into the right. You can hear us bat back and forth some rules of thumb valuations, both on if you’re going to sell for net profit versus I’m going to sell for revenue multiple, at what point that transitions and then what instances you can sell for profit versus revenue multiple.
We talk about things that sellers do really well and things that some sellers do very poorly. You can mentally evaluate where you, yourself might fall even if you never plan on selling or buying a SaaS company. Still a lot of good information here about how to have a business that is well-documented and that operates well.
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Thanks again to Basecamp and I hope you enjoy my conversation today with David Newell.
David Newell, thank you so much for joining me on the show today.
David: Thank you.
Rob: As I said in your intro, you’re a Senior Advisor at Quiet Light Brokerage and you specialize in SaaS. I wanted to have you on the show today because obviously, a huge chunk of our listenership are either SaaS founders, aspiring SaaS founders. I’ve been saying this for years and people don’t tend to believe me. I’ll say you may never sell your business, you may never sell your SaaS app, but my guess is you will. Most people do.
We can point out a few examples, like Yesmail, MailChimp, Basecamp, and Wildbit. There are a couple others, but the majority of people eventually either get tired, get bored, get old and want to retire. They do whatever and they want to get rid of their business. Even if you don’t and you want to run it forever, running it as if it was a saleable asset can make the business more efficient. Not only make it more valuable if you want to sell it, but it can just remove your day-to-day stress and how much you need to be an operator in your business. Just make it a more efficient asset.
David: 100%. It’s very funny, actually, when almost everything that you do to improve the business for sale actually makes the business better operationally. It’s been said to me at least a dozen times when we’ve gone through the prep process for going to market. Owners have said I actually decided that I really, really love my business. I’m not sure whether I want to sell it now, having gone through the kind of understanding that it’s needed to prep it for the market. It’s a philosophy and a mindset that if you build in from the get-go, you’re only going to improve your life operation in and of course when you come to market.
Rob: That’s the thing we’re talking about before we hit record, that whether you’re a seller or whether you’re going to operate your business, thinking like a buyer is just helpful to have that context and that it can improve your business, as you’re saying, operationally. I think a key piece to this is as a listener, if you’re listening to this you think, I never want to buy a business or I never planned to sell a business. I would reconsider that mentally because I thought that I wanted to, and now I’ve sold many. Also, even if you truly never do, still hearing how this works can improve the business you run day-to-day.
As we get into it, I want to set the stage for folks. They may have heard of Quiet Light Brokerage. Quiet Light’s been around for 13 years, you were telling me since 2007. I didn’t realize that they’d been around that long. I’m curious how many deals approximately or just some idea of how large the brokerage is, how many deals you guys do in a year?
David: There are 10 of us now internally working as advisors in the business. The deal count varies by year (I think), but it ranges usually between 75 and 100 close transactions a year. The average is about a million to 1.5. Say, it’s typically around the 75–100 million in close transactions a year.
It’s a lot of activity across a lot of people and a lot of business models around us. We do e-comm, SaaS, and content. We really get to see a lot of different digital business models and interact with a lot of different buyers and sellers.
Rob: Some people hear those numbers and they think that’s not a lot and other people think that’s a lot, depending on the perspective you come from. When I think of building a little business and selling it for a $250,000– $500,000 sale price, you have to do a lot of deals in a year to get to that $100 million mark. I’m curious. Let’s say I own a SaaS app today and I was going to sell through a broker like Quiet Light. What’s the bottom end? It’s seller discretionary earnings, but let’s define that in a minute. Let’s just call it net profit for now. We both know it’s SDE, but what’s the bottom end net profit that would be worth going through a process like this for a SaaS app?
David: I think the floor really for us varies by different advisors. For us, it’s about $100,000. We tend not to list anything below the $250,000–$300,000 mark. There are the more independent brokers or smaller and […] places that might do it. Once you hit that $100,000 threshold in SDE, then it’s very much worth stepping into working with one of the more established brokerages.
Rob: Right. Let’s define SDE. Let’s get into that. Seller Discretionary Earning, the way I’ve heard it described to me or the way I understand it is, it’s your EBITA, it’s your net profit that you would make from the business in a year, but you get to add things back to that.
For example, I always charge my laptop, my cell phone bill, my home internet bill because I work from the house. Some people charge their cars, I don’t know how they justify that if you’re earning a SaaS app, but people charge all types of stuff. I’ll charge trips to conferences. I just charge it all to my business. Even a salary that I take out. All of that, I can add back in because it is profit in essence and I’m just taking out and maybe using for expenses that are maybe on the edge that otherwise, I would just pay for it personally. Is that an accurate representation? Do you have anything to add?
David: Exactly. I think it’s operating profit plus three big categories of expenses. All of your owner compensation, and that could include your health insurance and anything basically attached to you and compensating yourself, dividends and so forth. And like you said, anything that’s personal expenses—travel, meals, accommodation. Just random things that people like to add in to reduce their end-of-year tax bill. The third piece is one-time sunk expenses. For example, you got a trademark that year or you did something like intellectual property work or some legal work that sunk. Anything that’s not going to be recurring or that a new owner taking over the business wouldn’t like routinely have to pay for, so you’ve taken that on, you can add that back. Those three categories of expenses you can add back and then you get to that magic SDE number.
Rob: And then if we were to roll from SDE right into valuations. Let’s talk about SaaS valuations these days. I have some rules of thumb, I’m curious to see if they’re still relatively accurate.
There’s this conversation around selling based on SDE or profit, in a sense, versus selling on revenue multiple. The way I try to describe it is if you have a strategic buyer where they’re going to acquire the company usually with the team and the technology, if I were selling my company and their strategy was buying, I would only sell for a revenue multiple if I were selling a SaaS app.
In addition, there are private equity firms that are paying revenue multiples. Once you get started getting to seven figures, they will pay revenue multiples. This is specifically SaaS because I’m not hearing about this in ecommerce and I’m not hearing about this in content sites, but SaaS is hot these days. Versus selling on the net profit multiple, the SDE multiple.
I’m throwing this out and I want you to counter or correct it. But those tend to be the smaller deals that I hear about. If you’re doing, like you said, $100,000 a year in SDE, then you get a multiple on that. You’re not going to get a multiple on top-line revenue. Where am I correct and incorrect with that analysis?
David: You’re absolutely right. SaaS is very interesting as a valuation landscape. As you said, it’s the only business model that straddles to different valuation approaches. Your earnings led multiple or your revenue led multiple. I guess some of the confusion that comes up with that—which one to use when—is really in thinking about where’s the life cycle of the app?
As a rough guide, I would say that the revenue multiple starts to kick in as a valuation approach app, like you said, $1 million in ARR. That’s not an absolutely hard and fast number, but the reason it’s chosen there is typically because the business has started to achieve a level of scale at which the buyers that are operating there, like PE and strategics, feel that its commencer to apply that kind of valuation approach.
There are some other caveats to it, which the business also needs to (at that point) have been really reducing its churn down to 4% or lower per month. It really needs to have a proper team in place, proper CTO, proper development customer support, onboarding, customer enrichment team. All of which would have done the work of reducing the churn component. The last piece is it really needs to be starting to grow very, very strongly, at least 40% year over year in revenue growth.
What you see basically is most apps—you know this, Rob, because you started several yourself—start as they often a single owner operated businesses. You build out the code base, you start getting your customer base, you start generating some earnings, and you can beget to $100,000, $200,000 or $300,000 in MRR. An app can actually get to be relatively profitable if you start adding back your owner compensation.
That’s the kind of early stage life cycle of an app. If you want to, you can exit for an SDE-type multiple. But there’s almost a decision point you need to make there, and I think you did this expertly with Drip, of course, where you just decide, I’m going to start reinvesting all of the profits of the app, everything I have into getting a team in place, into getting proper development, customer support, and start ramping as much as the marketing as possible. You then start to head up to that seven-figure ARR figure and then you’re really solving some of the bigger challenges in the business. You’re taking it from this smaller side project app, if you like, into what starts to look like a proper company.
When it comes to deciding, is my business earnings or revenue multiple based, what does it command, you really have to look at what’s the stage in the life cycle that it’s at, how fast is it growing, does it have a proper company operator surrounding it. That’s going to inform who’s going to be interested in buying the business, which to your point, informs what actual valuation approach it takes.
That’s how the dynamic works. It can vary a bit even around the size because you can still get a revenue multiple for a business that sets (say) $400,000 or $500,000 in ARR because you may have solved all of those problems very quickly and you may have a strategy that’s a great fit knocking on your door. But on average, it tends to be at the seven figure and up.
Rob: Yeah. I’ll keep some folks anonymous for obvious reasons, but through stuff we’ve worked on with TinySeed, I know of a founder who got an offer and accepted it. It was 10X revenue and his revenue was approaching six figures ARR. He’s still in five figures, but he had really good tech and he had just enough traction. It was worth it and he wasn’t going to sell for less. There are always exceptions to the rules, of course, but I like the way you’ve thought about it, the way you described it.
When I think then, let’s talk about selling for SDE multiple. Someone asked me the other day. They said, I have a SaaS app that’s doing a couple hundred grand a year in net profit. What type of valuation should I expect? I said it depends on how fast it’s growing and stages, that and stuff, but I would think 3–4 times your annual net profit or your SDE.
Often, when I run a loose rule of thumb, I’d go 3½ is a typical one I use today. And then I said if it’s flat or declining, it might be something a business that I sold, that you and I worked on several years back. If I recall it, it was like 2.7X because it was either flat or actively declining a few percent per month that time. Of course, I was willing to sell it because it was still a nice chunk of cash for me and I had so much else going on that I just wasn’t going to turn it around. With that range in mind, what do you think?
David: I think the markets probably got a little bit more buoyant since then, which is good for sellers. I would say that now, the typical range is between three and five. The median, I would say is probably 3.8, 3.9 or so. The big informing, there’s always multiple variables that really define where you fall in that range, but I think the big things are really age, growth, churn, and owner time. Obviously in the one that we worked on.
Typically, you probably wouldn’t try and list something like that. We felt that we like the underlying app and even with slight decline, we probably got away with it. And we did at the end. I think 3–5 is a solid range to think about. If I think of an app that’s doing 25% growth year over year, that (say) 20 hours of work a week and maybe they’re 2 or 3 years old, that’s probably going to come on to something around the kind of 3.7–3.8 level with relatively low churn.
Rob: Yeah. This is great. I was doing this buying and selling stuff before I knew about any of the brokers. Really before the brokerage ecosystem had evolved in our space. I was buying and selling on SitePoint, and then on Flippa when it came around. The multiples there were 12–18 months of net profit. It was really gnarly.
David: It was the Wild West back then.
Rob: It was and it was tough. I bought a few deals I just got completely screwed on and then I got several deals that allowed me to quit my job. But I, for one, like the fact that we do have this. As a seller of apps, as a builder, as a maker, I think the fact that we have raised that multiple for SaaS, that this 3X–5X range exists, and then we all know that because it was really helpful.
It was similar to buying and selling real estate. Yes, we have Comps, Zillow, and Redfin. You can get an idea of what something’s worth versus certain assets like art of really expensive silver-age comic books. It’s not as liquid a market and often it’s hard to really find out how much this thing is worth. Having these rules of thumb is helpful for us as an industry. It just allows there to be more of a liquid space because buyers don’t come and think, I want 1X, and sellers aren’t thinking, I want 10x. That’s an illiquid market. The closer we can narrow it down to where everybody’s on the same page you’re coming to a transaction, the more likely it is to go through.
David: Yeah. Not to pat myself too much on the back here, a lot of that actual improvement evaluation has come from professionalization at the secondary market and that has come from a lot of advisors working really hard to present deals better, get better metrics, do a lot of buyer and seller education and just make the whole ecosystem way more transparent and robust now. That’s why the numbers have gone to where they are.
Rob: Yeah, I would agree with that. Those are SDE (Seller Discretionary Earnings) which again, in my mind it translates to net profit valuations. If we’re going to talk about revenue valuations, I don’t think we spent too much time on it, but again, when I think of an app that’s growing (like you said) 40% a year more, hits that seven-figure ARR mark, again, as a seller I would always do forward-looking ARR especially if I was growing. Meaning you take the current month then multiply it by 12. You don’t look back at the last 12 months.
I would think if I got to that million-dollar mark, then I’d be looking at between maybe 2X and 4X of revenue. As they start to get up to $3, $4, $5 million, I’m thinking 3X–5X, 3X–6X revenue. It can go up and down from there. Obviously, a lot of factors, but is my mental model (you think) is accurate or what are you seeing in the market today?
David: I think it’s probably a little richer again. This is a difficult one because as you know and you’ve seen a lot in TinySeed, there’s a big distortion factor between where should […] can come in on specific deals, when the right stars align, and where private equity (I think) arguably set a more stable financial approach to valuing businesses. I tend to try and stick with the financial private equity model because you never know when the strategics are going to come in with the whacking multiple that makes sense specifically for them.
I look a lot at this concept of the rule of 40 when it comes to revenue businesses. That’s a revenue multiple in SaaS businesses. That’s basically if the businesses’ revenue growth plus its EBITDA margin for that year is at or above 40%. Let’s say it’s growing at 35% year over year and it’s got 5% in EBITDA margin, then it’s just to that threshold. It starts to command (probably at that point) around the 3½X–4X revenue, and then every kind of meaningful step-up is above that level. If it’s growing 50% year over year or 55% year over year and has a 5% EBITDA margin, add it together it gets to 60%. Then, it’s 20% north of that rule of 40 number, so it really starts to approach higher than that. All of that needs to be qualified with the quality of that revenue growth, which then feeds into what’s going on with the churn number.
The range that I think balances revenue multiple would stretch if we’re just talking about where PE guys land. Yes, anywhere between two at the bottom, where something that’s really, really flat, stretching up to eight times of seeing private equity guys comfortably go to, they tend to tap out a bit after that. Then, north of that is very much the realm of strategics. That’s very, very specific and unique to the deal in question.
Rob: And the higher the revenue, the multiple it tends to edge up to you. If you’re at $2 million ARR versus $8 million ARR, it’s a different conversation.
David: 100%. That’s the same across every business model. The reason for that is simple, which is that it’s much harder to grow faster in a scale and you have a much more valuable business oversee your scale than you do believe that. If you’re continuing to grow 40% year over year doing $10 million in ARR versus $1 million then yeah, it’s going to be a meaningful shift in multiple.
Rob: I want to mix it up a little bit. You’ve done a lot of deals in your career, but maybe if you can think back to an example in your head of a deal that you worked on in the past year where you’re representing a seller. First, I want to talk about—obviously, we’ll keep it anonymous because of NDAs and all of that—when was a deal where you felt like the seller just did everything right, had all their ducks in a row and as an advisor, it was just a really, really easy deal to present and it was obviously had all right information and stuff?
I love to hear some items on that list where you showed up and this thing is dialed in. Then, we’ll flip and point where someone did everything wrong or most things wrong and maybe hear about the most common pitfalls that people have in businesses that lower their valuations. I really hope the one who did everything wrong was not me. Let’s start with everything right.
David: I think if you want to get the best value in the market, you have to have transparency and you have to be able to display how good a business is. That really pours through into two deep components, which is the SaaS metrics, pertaining to all of your revenue churn, LTV, ARPU, everything. The more granular you can get into that, the better that […], the better. The second is (of course) the financial side of things.
Where I see the biggest challenge come up with SaaS businesses is that, in my experience working with a lot of SaaS businesses, they often have multiple projects on the go at any one point in time. They hold them all under one particular holding company and they share their resources across different apps. Some of which works out, some of which don’t. Which means that you then have this incredibly mixed expense base across all of these different apps. When you go to sell it, it becomes extremely impossible or extremely difficult to articulate to a buyer how much expense should be attributed to a particular app, the particular app in question.
Thinking about this contrast of one business that worked really and one that didn’t, […] six months or so. The biggest marker as a difference was that in the case of the one that was working very well. She turned up everything was incredibly well dialed-in in terms of […] well her metrics. Financials were completely crisp and clear in QuickBooks, isolated within one corporate entity, everything was measured up and tracked. She had IP assignments already in place with third party developers. Measures how to […] documentation, set and ready.
The biggest thing that she did right was she had taken a very, very structured approach to marketing in terms of contacting, lots of affiliates, lots of influences in her space, and put everything that she’d ever done into a spreadsheet in terms of contact information and communication. That was an example of incredible level of detail. But when you could display that to a buyer and say you can literally just pick this up, go, and run with it now, it was a slam dunk going to market. We had incredible success with that and put it under offer very quickly, a very high multiple.
Conversely, just recently, I had a listing where all of the customers have built essentially by wire. Nobody’s using Stripe or any of the classic merchant processes. There’s nothing to plug in in terms of SaaS metrics. There was no tracking of customer numbers, no tracking of any SaaS metrics whatsoever, you just got X dollars in the bank every single month. We like complete opacity into what’s actually going on inside the business.
We essentially had to go back three years and rebuild the customer waterfall chart that you would normally see in biometrics or something by hand, which is very time-consuming. I think he’d run into the same issue, again, with the number side of things. He had multiple app developers working across them all and then you just run into a real problem with buyers around how do they trust the numbers that you’re saying in terms of the expenses associated with it.
It’s a tricky one. To be really honest with you, that situation is not entirely cured through the multiple. I think a lot of the times sellers […] take a whole multiple, one or multiple off my price if I deal with that. Sometimes, actually, it becomes almost impossible to sell. You reduce the trust down because it’s just not enough transparency. I think really having metrics and financials dialed. I know it sounds incredibly basic, but it’s very, very important before coming to market.
Rob: I can imagine it sounds like documentation is a big part of it and just clean finances and clean metrics with SaaS would be the thing. As I think about it, when we go to invest in TinySeed or pre-TinySeed when I would go to invest with my own money, there were just a handful of things I asked for. That’s what it is. It’s like, what do your numbers look like? What’s your funnel look like? What are your conversion rates here and there? And I’d probably dig in more maybe than a buyer of a SaaS app would because growth is the end result of all of that stuff.
When we invest, I’m like, what is your trial-to-pay, what is your visitor-to-trial and all that stuff. It gives me a sense of the business. I’d have a mental model about how SaaS works and I can start fitting it into these buckets. It does make sense that that, to a buyer, especially a savvy buyer, can really describe the health of the business just by having clean finances, clean metrics, and having a reading document in a way that you can prove it out.
I remember when I sold HitTail, I’m trying to think if I had stuff split out and I don’t think I did. Certainly with Drip, by that point I had spun it out into its own S Corp (I think), whereas HitTail was mixed in and I did have to do some pulling apart of expenses. I remember it was a lot of work on my side. It was not an ideal situation. That would certainly be a mistake I wouldn’t make again in the future, is having shared bank accounts, having shared credit cards and all that. It just seemed easy at the time.
Again, it’s that thing of, I don’t think I’ll ever sell this. Then, you get to a point where I want to sell this. Now it’s a real pain in the ass to go back and reconstruct the stuff.
David: You can get away with that to a crazy degree on a smaller sale, which is a situation around HitTail. If you did try to do that with Drip, it would be almost a nonstarter. The challenge is that—this all Rob—when you’re building a business, it can be very easy to get stuck into the operation nuts and bolts and not really zoom out and have to think about that particularly on the finances side of things. I think most of the time people have got the metrics property data, still sit every now and again without paying a bit of a piece. If you start scaling the business, you end up in the situation where you are (I’m saying this) at a reasonable scale, but it looks like a car crash when you look at it from a reporting standpoint.
Rob: Speaking of reporting, there’s obviously these great metrics tools like Baremetrics, ProfitWell, ChatMogul are the three that I hear about most often and frankly a bunch of my investments I use them. If someone uses one of those, is it pretty much a slam dunk for you guys to pull stuff out?
David: Yeah. That stuff is de facto standard now. I think ProfitWell is free as well. It’s no excuse to not use it.
Rob: Yeah, no indeed. In fact, one of the TinySeed companies called Summit—usummit.com—integrates with all three of those and then pulls their data in and does forward-looking projections. If I was a buyer these days, of course I want to look back, but I almost would love to see different scenarios of like, hey, if I can improve this number to this or if I hire a salesperson, I think it’s going to do this, you can project it out. I think that could be a pretty interesting thing moving forward.
I think the founder’s headed where the puck is going in terms of this like SaaS tools, both metrics tools but just all the tools we have to build these apps as they get more and more sophisticated. They can make it just a little bit easier as it gets more competitive. I think we need better tools to be able to keep up.
As we start to wrap up, I want to ask you a little bit on the buy side. I tend to think on the seller side and I know you do, too. As an advisor, you deal with the seller first. You have to get their numbers together, put together a prospectus, and you’re essentially marketing that to buyers.
If there are so many audiences who’re thinking about maybe buying their first SaaS app and whether they have a couple of hundred thousand in cash, which most people don’t—I’m guessing—whether they do have some money to do it or whether they are going to be thinking about doing an SBA loan or come in a little bit of seller financing along with some cash, what are the best buyers have? What do the best buyers do that’s different than deals that are maybe more difficult or they don’t go through because of issues with the buyer?
David: The most intelligent buyers tend to understand that a really successful deal will come together if they go out in partnership with the seller that’s already there. I think they take an extremely collaborative operation even from the outside. As soon as they jump on the call, if they’re like the early call about discovering more about the business, they’ll send you to sign a bill of friendship and relationship right away.
Rather than looking at it as a closed-and-done transaction, where just going to pay the amount, do the due diligence, clays out, and leave it, they realize that the owner is still a massive storehouse of information within the business. That is going to give them, if they can keep them on site and maybe can keep them incentivized to help consult (for example) after the deal, that’s going to be massively conducive to their success in the business. Everyone that I’ve seen is a master operator when it comes to buying the business. That’s a kind of partnership vibe right away and they continue it through due diligence.
That intent to create that deep relationship per sale is incredibly important. Particularly the larger the deal, the more so. Then there’s just so much per sale and any deal that you don’t know fully about the asset that you’re buying, and obviously, you know this Rob to some extent, it was obviously moving over to Lead pages to help the first few months or the first year or so. The same principle applies even on smaller transactions. I think that really, really intelligent buyers get that.
I’d also say we respect their due diligence process as well. They get very deep into ensuring that they’re going to be able to run with the business per sale, so looking a lot into the quality of the codebase, looking how well annotated it is, looking at how documented it is, speaking a lot with the developers to really understand some of the critical components behind it so that you don’t end up in a situation, 3-6 months post sale, where you were tinkering around with the codebase that you don’t fully understand yet, and the seller’s not around and not particularly amenable to helping you.
Everyone that I’ve seen that does very successful by-side work, kind of sticks to those principles and plays them out from offer through due diligence and then to closing.
Rob: All right, David. Thanks so much again for taking some time with me today. Folks want to dig more into this stuff. You’ve done a lot of writing on this topic and one of the articles is like a damn book. It’s like an ebook length for sure. Will link it over the show notes, but it’s called How to Build, Value, and Sell a SaaS Business for Six, Seven or Eight Figures. There are eight different sections and you just talk more in-depth about all the stuff we’ve talked about today. Again, link that up into that show notes.
If folks want to keep up with you at Quiet Light, it’s quietlightbrokerage.com, and on Twitter it’s @quietlightinc.
Thanks again to David for coming on the show. I haven’t done a Q&A episode in a while, but I think in the next one or two episodes, I will be. If you have questions for me or a guest that I bring on the show about this ambitious yet sane SaaS companies, a lot of bootstrap, some self-funded, there’s a few that are raising their angel rounds and they’re indie funded, but just around this idea of building companies where it’s founder first, where founder maintains control, where we focus on building profitable, real companies, real businesses for real customers. Send those questions in firstname.lastname@example.org. Voicemails always go to the top but always happy to accept text questions as well.
Thank you so much for listening and I will talk to you again next Tuesday morning.
In this episode of Startups For The Rest Of Us, Rob interviews Derrick Reimer about the selling of his product Codetree. They discuss everything from the inception of the idea, to gaining traction, to launching, and finally the negotiation and sale.
Items mentioned in this episode:
Rob [00:00]: In this episode of ‘Startups for the Rest of Us,’ I talk with Derrick Reimer about what it’s like selling a $128,000 side project. This is ‘Startups for the Rest of Us’, episode 311.
Welcome to ‘Startups for the Rest of Us’, the podcast that helps developers, designers and entrepreneurs be awesome at building, launching and growing software products whether you’ve built your first product, or you’re just thinking about it.
Derrick [00:28]: And I’m Derrick.
Rob [00:31]: And we’re here to share our experiences to help you avoid the same mistakes we’ve made. What’s the word this week, sir?
Derrick [00:35]: Well, I’m getting geared up for a real winter to come for the first time in my life.
Rob [00:40]: Indeed. It’s been getting chilly the last couple of weeks, huh?
Derrick [00:42]: Yeah. We had our first drop below freezing last night, I think. For those who don’t know, I recently relocated, along with you, from Fresno, California out to Minneapolis, Minnesota. I’m a born and raised California native, so this is all a new experience for me.
Rob [00:56]: Well, I guess the highs have been in the 50’s, which isn’t bad, but when I’ve been getting to work in the morning it’s like 44 with wind. And realizing that it’s going to be 50, 60 degrees cooler than that here in a few months is a little chilling. But it’s been like, “Boy, I’ve got to get the big coat out of the closet.”
Derrick [01:12]: Yeah. My wife and I went out and bought jackets that can actually keep you warm in this type of climate, because we’re used to just our California jackets. Right now we’ve basically reached California winter status and it’s only October.
Rob [01:23]: Yes. That’s right. It’s really October. Cool. We’re here to talk today about your recent sale of Codetree. To give folks a little bit of background, you’re Derrick Reimer, cofounder of Drip. You were CTO to my CEO, nd we were acquired three months ago by Leadpages, everyone knows. But during the time that we were building Drip I have always had my little side projects, podcasts, and conferences, and I had HitTail going, and you went and built Codetree.com which is lightweight project management that lays over GitHub Issues. This actually came out of a need that we had internally, right? Managing multiple developers and prioritizing?
Derrick [02:02]: Yeah. We were using FogBugz before we switched to using GitHub Issues, and we were just starting to see the product wasn’t totally actively maintained and it wasn’t meeting all of our needs. So I really wanted to start using GitHub Issues. We were already using GitHub in a lot of our processes, so looked at that idea of using GitHub Issues, and it was not quite there. It was about 80% there what we needed. It seemed like there was an opportunity to just build a little layer on top, something that would give us the ability to prioritize things, and maybe view things in a little bit more compact manner. And so I looked into what it would take to do that, and then the light bulb went off in my head and I thought, “You know, I wonder if other people are using GitHub Issues in this way, and need to do a little bit more project management type of stuff with it?” So it was right around 4th of July, just about a year and a half ago, when I threw up a landing page for it. I just threw it together in a weekend, and started tweeting about it, ran a little bit of Twitter ads to push it out to basically the people on Twitter who are following GitHub, so I could target them pretty easily, and immediately started getting a bunch of interest, which kind of set me off on the track of building it.
Rob [03:09]: And were there a lot of competitors doing similar things at the time, or were you the one of the early ones?
Derrick [03:13]: There were a few. There have been more that have popped up in the last year and a half for sure. I did take a look at them, and they all were kind of lacking exactly what we were looking for. I had a little bit different vision for how it would work. Most of them were kind of locking you into a Trello-style task board view. It wasn’t quite exactly what we were looking for.
Rob [03:35]: Right. That’s what I liked about Codetree. We – just to give folks full disclosure – this is still what we use – even though you don’t own it anymore – we use it as it runs all of Drip’s [basically?] engineering prioritization. So all of our issues, bugs, new features go into Codetree, and we assign them out to all the folks who are working on them. We have our DBA in there. I’m in there for some kind of project management level stuff, and decision making stuff, obviously not pushing code. But one of the coolest parts of it — well there were a couple of cool parts. One is that you can do prioritization, which I think at the time you couldn’t do in GitHub. And the other thing was the fact that I can look at a table-based view per developer. So the Home screen for me is just each developer with a table of the first 15 issues that are assigned to them in priority order. But the developers themselves can just switch to basically a task-based view, I think you call it – task list view – and it’s like Trello. And so you can just work in that view. That was like the ray of sunshine. It just made tons of sense to do that.
Derrick [04:30]: Right. So it was very specific use case around GitHub Issues, and so it was something that I felt like was pretty safe from GitHub building themselves. I felt like this was a good alternative use case that that would be, hopefully, pretty resilient against GitHub kind of clobbering what I was trying to do.
Rob [04:48]: Right. I mean we had conversations all during this, because you and I were in a Mastermind with Phil, and we would meet every couple weeks. We were talking through like you need to be agile enough to stay ahead of them. It could potentially be an acquisition target later on, which is good. They very well may clobber you, but you have to think about innovating and doing things that they aren’t doing.
Derrick [05:06]: Right.
Rob [05:07]: And, you know, when you initially launched it, if I recall – I mean this was before you had an ownership stake in Drip, and you were essentially an employee of the Numa Group, which is what owned Drip at the time. And you were looking to grow this into like a full time gig.
Derrick [05:24]: Yeah. I definitely had the itch at that point to have equity in something, and to be using my skill set that I had built up over the last few years building products and then working alongside you on HitTail and Drip. I was really looking to leverage that into something that I could have ownership in. So I saw Codetree as a good stepping stone. You know, you talk about your stair stepping approach, and I felt like it is SaaS – which is a little bit more complex than something like a Word Press plugin or a one-time sale product – but I also felt like it was small enough in scope that it was manageable for my first crack at a SaaS app.
Rob [05:57]: Yeah, for sure. And this kind of was part of the reason we started having conversations about that, because it occurred to me like, “Wow! Derrick’s really valuable to Drip.” And you, obviously, had ownership and kind of a love for both of these products, right? You kind of had the desire to do them both, I think. And you were doing them both for quite some time. And I think you had dropped down to three quarter time with Drip at one point. And that’s when you and I really started talking about, “What does the future look like? Where are we 6 to 12 months?” And that really led to the conversation of, “All right. Let’s talk about cofounder status. Let’s talk about ownership.” And you communicated well. You were like, “I need to feel ownership in something. Like I’m the founder, I’m an entrepreneur. Can’t keep doing this stuff forever and working for somebody else.”
Derrick [06:37]: Yeah. There were like two conversations that stand out in my mind. There was a conversation we had right around the time when I was starting to build Codetree. And you approached me and were like, “All right. So, where are we heading?” Basically, “Is my long-term with Drip, or is my long-term with Codetree?” And at that point you were looking for a commitment, like which way is it going to go. And it was a tough decision at the time, and I ultimately decided to continue development on Codetree and forego setting that aside in favor of an equity stake in Drip. And then I think it was maybe seven, eight months later when Codetree had launched, and it was just starting to gain traction when we had a second conversation that ultimately led to me kind of doubling down my time on Drip and letting Codetree remain a side project.
Rob [07:19]: Yeah. I mean speaking of that launch, let’s give folks a context of how long did you spend developing it? How big was the list by the time you launched? How did you do the launch? Did you just email everybody? What was the early traction? We can talk numbers if you want, loose MRR, or if you don’t feel comfortable, that’s cool too.
Derrick [07:35]: I broke ground on – at least launching a landing page – in July. And –
Rob [07:41]: Yes. You started marketing before you started coding.
Derrick [07:43]: I did, yeah.
Rob [07:44]: I love it.
Derrick [07:45]: It was the first time I had done that. I had tried building other projects before, and I, of course, spent months building the product before anyone had even heard about it. So, I was determined not to make that mistake again. So, I put up a landing page, got the early traction. I started running Twitter ads and I felt like I could target the GitHub audience specifically. I felt like that was a good medium, and a lot of developers are on Twitter. I managed to find some things that converted well. I was gathering maybe 20 to 50 email addresses a day of just people clicking a button saying, “Yes, I’m interested in this product when it launches.” I had basically a one-page landing page set up that kind of described the problem it was solving. It had a headline something like, “You love GitHub Issues, but you hate project management, and here’s how Codetree can help you do your project management in the GitHub flavor.” basically. So that seemed to resonate really well with a lot of developers. I would say I didn’t have as many conversations up front as I probably should have had, but I took the signal of people clicking this button at least signaled their interest enough for, hopefully, a few people to be willing to pay for it once it launched. So with that bit of traction I started development probably a few weeks after I launched the first landing page. It really was a nights and weekends project for me. I was fulltime on Drip. It took me a good six months before I was able to launch an early access. I had a list of maybe about 20 people who I had more direct conversations with later on in the process, and I think I just gathered those based off of sending out an email to the mailing list that I had gathered through the process of running Twitter ads. By the time I launched early access I probably had maybe 1,500 people on that list; so a good chunk of people to start trying to get for my early access program. The response was good, but it was a good learning phase, as is most early access programs for SaaS apps. I learned a lot about what things people wanted built, and I kind of had to come to the decision of: Was I going to spend a bunch more time building full laundry list of features that people wanted, or was I going to launch what I had? And you, me and Phil sat around Mastermind meetings talking about strategy about this, like ‘Should I just get it out there, or should I try to build more features?’ Ultimately there were a few 11th hour features that made it in. Like I built a rough version of the task board, I believe, right before launch, but a lot of the things I just saved for post-launch. So it launched in January. First landing page in July, launch in January.
Rob [10:12]: Very cool. Do you remember what the conversion rate was to trial? And did you ask for credit card up front? I don’t recall.
Derrick [10:19]: Yeah, so no credit card upfront. I felt like developers especially would have a big aversion to that. And the conversion rate, that’s a good question. I’m pretty sure I got hundreds of trials after the launch, and I had a 14-day trial, so of course, there was the waiting game of waiting to see how many of those would actually convert. I believe at the end of my first month I had maybe between $400 and $500 a month in MRR, which felt like a big win at the time.
Rob [10:44]: Yeah. That was a nice little jump, kind of from a standing start, right, because you weren’t working from a network you had, you weren’t working from an audience. You just kind of proposed an idea, landing page, and built enough of a list to hit that. And that, if I recall, covered your expenses at the time. I think you were on Heroku and stuff, and maybe you made just a trivial amount of money.
Derrick [11:03]: Yeah.
Rob [11:03]: That’s cool. And then, it was a side project but you were investing time into a little bit of marketing and a lot of feature-building for the next, what was it, like four to six months before we really had the conversation about Drip, and you kind of shifted focus and really put it on? It wasn’t autopilot so much. You were still fixing bugs, and I remember you released some tiny little features stuff over the next six months after that maybe. But how long was that initial kind of investment after launch, and then we can take it from there.
Derrick [11:31]: Yeah, so I definitely spent a lot of time – nights and weekends – building out functionality in those months’ post-launch. I was trying to keep momentum going, and also trying to address all of the feedback that I had gotten from early access and from the initial wave of interest. So I think my wife could attest to that time was pretty crazy. We were still super aggressive on building out Drip, and so my days were filled with a lot of high intensity work, and then nights and weekends I was spending a lot of time building out features and probably not focusing much on marketing at that point. I was really just trying to keep the momentum going from the initial wave after the launch, and I remember, I think it was in March, I actually took a work retreat where I knew there were some features that I needed to bang out but I wasn’t going to necessarily have time to do them split up into small chunks. I really wanted to get some long stretches of time to get stuff done. So, I think I stole away to the central coast for a few days and just worked around the clock trying to hammer out some of those features. So I definitely tried to get creative during that time to get some big things done.
Rob [12:33]: Cool. And then at a certain point, obviously, you know, we had this conversation, and then you kind of made that transition. It was doing a few thousand dollars a month at that point. Is that right?
Derrick [12:41]: Yeah. I think it might have been around $2,000 a month at that point.
Rob [12:44]: Cool. And then at a certain point late last year — it was funny. I think I had gone on a retreat, or something, and I had written in my notebook – it was a bunch of stuff for me. And then I thought, “You know what, I wonder if Derrick should think about – he has enough revenue history, and I wonder if he’s still kind of committed to Codetree long-term, or if he should think about maybe selling it? And I wonder what he could get for it.” It was kind of just this thought process, and I think at the next Mastermind meeting you brought it up. And you said, “I’ve been thinking about selling Code -.” It was just funny that it had like both hit us at the same time. It was either late 2015, or maybe early 2016?
Derrick [13:17]: Yeah. I think you’re right. Something like that.
Rob [13:20]: Cool. What was the process for you? What made you – the thought process? You know, why did you decide to sell it?
Derrick [13:26]: You know, I was feeling like the product had a lot of potential still, and I felt like I just — especially with my decision to double down on Drip, I didn’t feel like I had the time to commit to it. The product was relatively bug free, and there was a happy base of users using it. I was growing by a handful of customers each month, so MRR was slowly ticking up. But there was still kind of an ever-mounting list of kind of larger, high level features and directions that I could take the product to really provide a lot more value to the customers. And I just didn’t have the bandwidth to tackle those larger things. I knew that in the hands of someone else it could definitely reach a much higher potential then where I was taking it. Also, I felt like ‘This can’t last forever.’ This market is competitive enough, and there’s enough innovation happening with project management in general, that Codetree can’t maintain its growth and its revenue in an auto-piloted state. So really, if I am going to sell it, probably the right time was then before the product started to decline.
Rob [14:29]: Yeah, and if I recall I said I would kind of check – I think I even checked anonymously. Didn’t I say, “Hey, I’ll talk to Tom Smale at FE and just check, “Hey, hypothetically I have this friend who has an app doing this much per month, and this much history, and what do you think he could get for it?” And he kind of asked some more questions and threw some multiples around, and I think you were like, “Yeah, I think this is worth investigating.” And so I made an intro between the two of you guys. What came next?
Derrick [14:55]: Yeah, you introduced me to Thomas, and we talked back and forth a little bit. I provided some more numbers, and he came back and said, “You know, I think this is a really strong app. There’s a lot of people looking for SaaS apps in this price range. There’s a lot of people wanting a first app to buy, and many of their best ones are in the $500,000 and up range which are just kind of out of the range for a lot of beginning folks. Then on the lower end there’s like the types of products you see on Flippa, that are maybe $30,000 to $50,000, and not great code base and all the other problems that come with that.” So, he made me believe that Codetree really kind of sits in that sweet spot, and he felt like we would be able to sell it quickly and be able to get an all-cash buyer. So all these things sounded really attractive to me. At that time, we were already knee deep in negotiation with Leadpages and, I believe, we were starting to near letter of intent and due diligence phase with that. So really, all these things were compounding at once, and that made it especially attractive to me the prospect of getting this sale done in a relatively short period of time.
Rob [15:59]: Yeah, if I recall you and I sold Drip; you sold Codetree; you sold your house; I sold my house. Did you sell a car or anything during that time?
Derrick [16:09]: I didn’t, but, yeah, it was really like a period of mass liquidation.
Rob [16:13]: Yeah, it was such an interesting and chaotic time. But there was a feeling of energy. I remember us kind of talking about it, of like, “Man, it’s good to kind of get some of the fruits of your labor.” You know, or like to be able to take some money off the table. And also to feel – I know that it had bothered you for a while that Codetree was there, and you knew it was solid, and you knew it could grow, and you felt like — It’s just a shame. I felt the same thing with HitTail. It was like, “Somebody should be growing this, and it’s just sitting there.” And so I knew it was going to be a relief for you when it finally closed.
Derrick [16:41]: Right.
Rob [16:41]: And so, it’s due diligence, but it’s essentially like all the requirements gathering and all the numbers, right? The FE has a really intense process there where they ask you a lot of questions about MRR, and where the traffic comes from, and growth opportunities and all that. How was that? How long did it take?
Derrick [16:56]: I had been warned ahead of time. I think at MicroConf earlier that year, Patrick McKenzie had talked about his experience selling Bingo Card Creator. You had the experience of selling HitTail. And so, I knew that it was going to be an intense process, but I feel like you’re never prepared for that; for just the amount of in-depth questions that need to be answered. So preparing income statements, and deep in-depth discussion about what marketing has been done, and how much has been invested in all the different areas to grow the business, and on and on and on. It probably took a solid two weeks of time just in my off-hours compiling together information and pulling data out of Stripe and all the different places.
Rob [17:34]: Cool. And then the sale happened pretty quickly, is that right? If I recall, you had several offers or at least several highly interested parties pretty early on.
Derrick [17:42]: FE likes to do like an early access circulation of a new prospectus. So they emailed their insiders group and tried to drum up interest that way. I think there were maybe three interested parties who came forth during that period before it even went to the broader audience. And, ultimately, the buyers who bought Codetree came through in that early phase.
Rob [18:05]: Right. And for folks interested in hearing more about this – especially from the other side – the buyers did a really good job of putting together a series of three blog posts. The third one culminated in this extremely long, very highly informative article about all the terms of the deal, and negotiation, and all that stuff. That’s really why you and I are able to come on here and talk about it, and why in the intro, or in the title of this there is going to be a price. Otherwise you wouldn’t have done that. But they wrote a blog post called ‘What It’s Like Buying a $128,000 Side Project.’ And we’ll, of course, link this up in the show notes. During the negotiation, once you had all the docs in there and then you started getting offers, was that stressful for you? Or was it — you know, compared to the Drip sale, I know that they are different orders of magnitude in terms of stress – but were you stressed or concerned or, I don’t know, did you feel out of control at all with the Codetree sale?
Derrick [18:53]: I think I would have felt that way if I were handling it on my own. I think having David from FE International, my broker who happened to also work with us on the Drip sale, was really pivotal for me in just keeping a level head. He bore the brunt of circulating this to perspective buyers, and vetting incoming buyers, and handling all of the follow up. We would have discussions and he would say, “Okay, this is what they’re offering. What do we want to say? Are you okay with this?” And I could just give him back an answer like, “No, I’m not okay with that.” Then he would handle the whole process of thinking through the best way to craft a response to the buyer that would not totally tick them off, or turn them away, or whatever. So just not having to deal with those finer points of the negotiation really eased my mind. It was in that first weekend – right after David had circulated the prospectus to the FE insiders – when I got initial interest from the ultimate buyers of Codetree. We had a call with them, and that was a little bit stressful to jump on a call with potential buyers. You want to make sure you don’t say something wrong, or something that’s going to hurt your negotiating position. So I definitely felt on guard with the first one, but David did a good job of kind of mediating the conversation and making sure that he jumped in any time there was a question that maybe was not something that we were willing to disclose at that time. So shortly after talking to them on a call an offer came through. That was a really exciting – just to get the first offer was a really exciting thing. We can talk about numbers, talk about what we’re going to ask for it, but actually getting a cash offer was pretty exhilarating. But the cash offer was for $103,000. So it was way lower than what I was asking at the time. And so, that stuck in my head where I was – there was a lot of emotions around it. One, I was exhilarated, but I was also mildly offended maybe that I would receive such a low ball offer. I remember thinking I had to decide at that point, was I willing to take less than what I was asking or was I willing to sit it out and wait for the right buyer to come along? And fortunately, David was there. I think I also talked to you about it. And everyone said, “Look, you don’t need to concede at all at this point. Just wait.” And that turned out being the right decision. But I think not being a savvy trained negotiator myself, it’s hard to think of like, “I’m going to just completely walk away from $103,000.”
Rob [21:14]: Right. Yeah. It’s definitely shocking the first time you see that and think, “Wow! That’s going to be wired to me in a few weeks if this all goes through.” But I totally remember you were in such a good negotiating position because the app looked gorgeous, it was solid, it was well built. You had your reputation of quality from Drip. I don’t want to say “overshadowing”, but kind of that Codetree benefited from, because Drip is just a really respected product, easy to use, and looks good. There was just so much going for it that Codetree was, in my mind, a premium product and a nice – it was a low priced product in the sense of we see a lot of SaaS apps that come through and they’re $800,000 or whatever. And it’s like, “Really?”, you either have to have a lot of cash or take out a big loan to do it. But to find an app of this quality in let’s say the low six-figure range, it’s pretty uncommon. And so, my gut was that, yeah, you were going to get a full price or close to that offer.
Derrick [22:07]: Yeah. It was fascinating to read the third part of the blog post series that the Codetree buyers put out, where they kind of go in detail about negotiation from their side. And they kind of outline, “At this point in the deal, here was our negotiating position, and here was the seller’s.” And kind of talk about how I think as a seller I was probably in the better position on this deal. So it’s really fascinating to see their thought process and how it aligned with what I was thinking at the time.
Rob [22:31]: Yeah. There is just a dearth of solid SaaS apps for sale, period. And especially at this price range. And I have several friends who have been trying to acquire things along this line for 12 to 18 months, and it’s just not happening. It’s definitely a seller’s market today, in terms of if you have a decent quality SaaS app you can get a good multiple for it. Cool. And so, you guys went through negotiations, you eventually settle on the price – as we said it was $128,000 – and after closing, did you get the bank wire right away? The same day that it closed?
Derrick [23:04]: No, so okay. If you’re ever selling a SaaS app don’t chose non-wire transfer methods.
Rob [23:13]: You went with the three day ACH -?
Derrick [23:15]: I went with the ACH. And so that was, yeah.
Rob [23:18]: But why did you go with the ACH, Derrick? Tell everyone.
Derrick [23:21]: Because there was a $20 fee for the wire transfer.
Rob [23:23]: There was a $20 fee! That killed me. I loved it.
Derrick [23:27]: When I made the decision, this was like weeks before it was ever going to close, I’m like, “You know, yeah I’ll save $20,” but totally not worth it.
Rob [23:35]: And then you got there and it closes. And there is some stress, or some anxiety, through it, and you get there and you’re like, “Finally, it closed today. Such great news.” And you’re like, “I cannot wait to see that wire in my bank account.” That is the true culmination, and the big dopamine rush, when you see it, and you had to wait three days for it. That’s terrible. I was like, “Oh, no!” And I think I was like, “Can you change that? I’ll throw the $20 in.” You’re like, “I totally want to do it.”
Derrick [24:00]: I tried. I tried.
Rob [24:01]: But it was too late, because it was Escrow.com or something, is that right?
Derrick [24:03]: Yeah.
Rob [24:04]: It was already locked in. So that was funny.
Derrick [24:05]: Yeah.
Rob [24:06]: And so, if I recall the next week you showed up in a Tesla, right? Is that what you did with all the money?
Derrick [24:14]: Oh man. I wish. No, I stuck it in a high yield savings account.
Rob [24:17]: Very good. Nice play, sir. Well, yeah, I think we’ve pretty much covered it. Is there anything else that you feel like you maybe left out of the story?
Derrick [24:24]: No, I think that covers it pretty well. I think probably my take-aways from this – if someone out there in the audience is looking to sell their product – one of the biggest things is don’t underestimate the amount of effort that due diligence is. And there’s things you can do to make your life easier, like keeping everything separated. I had a dedicated bank account for Codetree. I had a dedicated Stripe account for Codetree. All my other different SaaS things that helped power Codetree were all siloed in their own accounts, and that made the handoff a lot easier. It made it a lot easier to narrow down the exact costs that were involved, and where revenue was coming from. And I could produce a bank statement without having to filter out other non-relevant transactions. And so that made my life a lot easier. But there was still weirdness with like, when a Stripe charge comes in on one month do you count it in the month when it happened or do you count it in the month where the cash hit the bank? And you’ll see in the write-ups from the buyers that one of their big issues during due diligence was this supposed discrepancy in revenue reporting. So, some of these little things that don’t seem big in the grand scheme can potentially hold up the deal.
Rob [25:29]: Yeah, you were really well organized. And that’s kind of your nature and I think it helped make this a less stressful process. When I sold HitTail, which was November – it was almost a year ago now – it was so enmeshed with other things because the Numa Group had all these products at one point, that it was much more of a headache for me. Even to just suss out the numbers- the expenses mostly – because they were all comingled with things on the same credit card, and then the transfer over it was actually in the AWS account that Drip was in at the time. It wound up being a big mess during the actual transfer process. But yeah, I think that’s a really good piece of advice for folks who are listening.
Derrick [26:05]: Yeah.
Rob [26:06]: Sounds good. Well if folks want to keep up with you online where would they do that?
Derrick [26:10]: You can keep up with me on Twitter. I’m @DerrickReimer. And I also have my website at scalingsaas.com where I blog occasionally and publish other content.
Rob [26:19]: Sounds great. And you’ve been cohosting the Giant Robots podcast for a few weeks, right? I think you’re on maybe a hiatus right now?
Derrick [26:25]: Yeah. So, yeah, Giant Robots is in its third iteration, and Ben is bringing on cohosts to cycle in and out. And so, I’ve had an eight-episode stint there and it’s been a great time. We kind of delve into the behind the scenes of building out SaaS apps, so we talk a bit about behind the scenes of Drip, and also some technical things too.
Rob [26:44]: Sounds cool. So if you’re listening and you want to hear more from Derrick you could actually check out certainly Giant Robots, the last eight episodes. I’ve listened to them all. They’re very, very good. And there is more about Drip and other stuff in there, too. And then, actually episode 274 of ‘Startups for the Rest of Us,’ you came on and we talked about how to mentally and technically prepare for your launch, and we talked through the launch of workflows that happened earlier this year.
Derrick [27:03]: Yeah, it was a good one.
Rob [27:04]: Sounds great, man. Well, thanks for coming on the show.
Derrick [27:07]: Cool. Thanks for having me.
Rob [27:08]: If you have a question for us, call our voicemail number at 888-801-9690 or email us at email@example.com. Our theme music is an excerpt from ‘We’re Outta Control’ by MoOt. It’s used under creative comments. Subscribe to us in iTunes by searching for ‘Startups’ and visit startupsfortherestofus.com for a full transcript of each episode.
Thanks for listening and we’ll see you next time.
In this episode of Startups For The Rest Of Us, Rob talks about the acquisition of his company Drip, by Leadpages. After finally closing the deal and making it public, Rob is able to talk about the thought process, negotiation timeline, and address some of the commonly asked questions about the acquisition.
Items mentioned in this episode:
Rob [00:00]: In this episode of Startups for the Rest of Us, Mike and I discuss the acquisition of my startup Drip by Leadpages. This is Startups for the Rest of Us, Episode 298.
Welcome to Startups for the Rest of Us, the podcast that helps developers, designers and entrepreneurs be awesome at building, launching and growing software products; whether you’ve built your first product or you’re just thinking about it. I’m Rob.
Mike [00:29]: And I’m Mike.
Rob [00:29]: And we’re here to share our experiences to help you avoid the same mistakes we’ve made. What’s the word this week, sir?
Mike [00:33]: Well, I’m in the middle of testing a pretty large data migration for storing the emails that are kind of on the back end of Blue Tick. So one of the things that customers have been asking for is the ability to see inside the application the emails that are being sent to customers and also the emails that they’ve received from them and whether those emails were sent by Blue Tick or whether they were sent kind of independently.
And because we have access to the mailboxes we can pull that information and display it. But obviously there’s some historical significance to a lot of those emails. So, if you sign up, let’s say today on Blue Tick and you probably want to be able to see the emails that you sent three months ago, six months ago to that person. So, we’re working on making those available inside of the application itself. And it just involves this massive data migration because it’s got to be done for every single mailbox and for every email that they’ve sent, which is “important.”
Rob [01:25]: Yeah, it’s interesting that when you’re building an app for the first time if you haven’t had tens or 100’s of users or you haven’t built something that has a lot of through put, you underestimate how hard it’s going to be to display this stuff and even store it long term. And just how large these data stores can get and how slow they get to query. So, I think by making this change early you’re probably getting ahead of the game here in terms of not having to do it once you have hundreds of customers and gigs and gigs of data.
Mike [01:53]: Well, we already have gigs and gigs of data to deal with. I mean there’s some where there’s like I was just running some local tests and I had to scale things down and say, okay, only deal with like 16,000 of these things because otherwise I would have had to deal with 250,000 and I’m just like, “No, I don’t really need to do that for just an initial testing.”
But, yeah, there’s just a lot of stuff that needs to go on. And I can’t do it all at once. It’s got to be kind of gradual migration for each mailbox which is kind of a pain in the neck. But it also kind of brings to mind that there are certain types of things where it’s easy to do when nothing is moving. And then if you have like a SaaS application where things are constantly being done or moving around or changing in the background, it’s almost like you’re a heart surgeon and the heart’s still beating and you still have to operate on it.
Rob [02:40]: Yup. Exactly. I mean I think that this is why some apps – I mean at a certain scale you just can’t do this anymore. This is why some apps that don’t add certain features that everyone’s clamoring for because it just becomes impossible to do. You know you can imagine being at, let’s say the scale of MailChimp with massive visiting, sending a billion emails a day or ten billion? I mean it’s like incredible the volume that they’re sending.
And so, while I’m sure people have been asking for automation and other features for years, you just at a certain point can’t do it and maintain the app and the throughput of the volume that you’re trying to do. And so, you have to make some of these decisions early because if you do hit scale, it can become a lot harder to do this down the line.
Mike [03:21]: You could probably do it if you were just saying, “Okay, let me toggle a flag in somebody’s account and allow them to do it.” But you still have to spin up API’s that are specific to that account and cross machines or cross data centers or something like that. And I imagine once you get to the point where you have to worry a lot about the scale and redundancy then it becomes even more challenging. And I can see how some companies would just say, “Yeah, we’re just not going to do that.”
Rob [03:45]: For sure.
Mike [03:46]: So, what’s going on on your end?
Rob [03:47]: Not much. Just hanging out. Nothing new.
Mike [03:49]: Nothing new?
Rob [03:50]: No. Oh man. I mean, I don’t want to underscore the importance in both my career and for Drip. And also the difficulty, the challenge of the last several month in that I haven’t been able to talk about what’s actually been going on with me. And I have two podcasts. I have a blog which I haven’t been updating because there’s nothing relevant that I could write about, because we were in the middle of negotiations for months, five, six months was just discussions with Leadpages. It feels really good both to close the deal because this big wave of stress kind of goes away, I started sleeping again, i started living more of a normal life.
But also, just the ability to just talk about it a little bit in public. And, obviously, I’m under NDA as acquisitions always are. Both sides are under NDA’s about specific terms and stuff. But there is still so much about the thought process and timeline and what went down that, I think, is good to talk about. I’ve always liked to share this kind of stuff because I think it helps other people. And that’s really what we’re going to do today. Kind of dive into probably the most commonly asked questions that I’ve heard since Drip was acquired by Leadpages about what, maybe, two or three weeks ago.
Mike [05:02]: So, for the people who may do exactly what I generally do for podcasts is skip the first 30 or 45 seconds. Setting the stage for them, Drip was recently acquired by Leadpages. So, could you walk us a little bit through kind of what the result of that is? Was it like HitTail where you’re selling it and you’re walking away? Are you sticking around with them? What’s going on? How did that happen?
Rob [05:21]: The fun part about this episode is you know the answer to every question you’re going to ask me, but you have to ask them to get the information.
Mike [05:27]: Yes, I feel like a futurist at this point. I’m going to say something and I know the answer.
Rob [05:31]: Exactly. So, yeah, I mean it’s a good point. This Drip acquisition really is more of a – it is a startup acquisition rather than a “sell your app” kind of thing. So, you know, I sold HitTail last November. And it was just the technology and the revenue on the website and the incoming traffic. And that’s where the value was.
And that is a very, very different kind of sale than what just happened with Drip. I think of it as selling an app versus a startup being acquired, like a fast growing successful startup being acquired, not for parts and not just for the people, which is an aqua-hire,not just for technology, which is selling your app; but the whole package. In my experience and my understanding that is definitely where there’s the most value to the acquirer. Those are the startup acquisitions where the purchase price is maximized because you’re not just taking people or technology. You’re actually taking it as a whole entity.
With a strategic acquisition like this where Leadpages – it’s an obvious fit. It’s obvious that Leadpages has landing pages and they collect emails. And the next step in that process is then to send email to people. They’ve always integrated with third parties and in this case obviously acquiring one like Drip is – it’s a pretty natural fit.
Mike [06:41]: Interestingly enough, that’s one of the pieces of advice that you might give to a single founder or a small startup where they have an existing product and they want to develop or launch a new product. And the question is, “Okay, well, what should we do?” And the answer is, obviously, try to leverage your existing customer base and launch something that is going to be complimentary to them. Or more valuable to them down the road.
So whatever the next step of their sales process is, for example, or more advanced features. And Drip really fits into that with Leadpages because Leadpages captures those emails and then you can use Drip to manage those email addresses after the fact. Now, you don’t have to use Drip but you could at this point.
Rob [07:20]: Yeah, and that’s been a big thing. Clay, who’s CEO of Leadpages, has talked about they’re continuing to integratewith all the other email providers and they want to be fairly agnostic to it so that it’s an open playing field for everyone. But there’s obviously going to be more that’s possible because now that Drip and Leadpages are owned by the same company, we can just do more things. You can do provide queuing and API’s and stuff that can just move more data easily than with a third party.
So that’s the thing. To take a step back, there are really two types of acquisitions. There are financial acquisitions where it’s based purely on numbers. And that’s like if you buy through FE International or you buy on Flippa. Those are the types of acquisitions I’ve been involved in.
And then there are strategic acquisitions and those are the kind where it is a strategic fit with someone’s or a company’s vision and their road map. When you look at Facebook acquiring Instagram, as an example, that was not a financial acquisition. They weren’t buying it for the revenue. They were buying it because it was a strategic fit into where they’re headed. It’s thus worth a lot more. Strategic acquisitions tend to have a much higher purchase price than financial.
Mike [08:26]: So, I guess on the concerns that some people might have, especially some of the customers that you have that are listening to this episode – because I think when you first started out with Drip, you kind of reached into your own network of podcast listeners and people who are in your network – one of their questions might be: what does this mean for me as a customer of Drip?
So, I guess maybe talk a little bit about that, because that’s something that you kind of have to take into consideration when you’re selling the product that you have. Whether it’s an acquisition that you’re just going to completely walk away from or you’re going along with. But you also have to take into account what’s going to happen to your customer base. Because you don’t want to make them angry because suddenly they’re no longer being taken care of. What sorts of thoughts did you have around that? And what sorts of things could they expect?
Rob [09:10]: Yeah. That’s a good question. Probably the first one that comes to most people’s mind. An early thought that I had and an early conversation that came about from it was – and Derek, who’s my co-founder with Drip agreed with this as well – is that I absolutely would not let Drip be acquired and have either the customers or the employees get a raw deal.
There are some startup acquisitions where startup gets acquired and it just gets shut down. I think Microsoft did this with Sunrise, which is a calendaring app. And I think Google does this pretty often, where they buy it for the team, they shut the app down and they integrate the technology into their own product. That, to me, hoses your customers who have invested their time and/or money into you.
There are certain deal breakers when you go into something like this. And it’s good if you know what those are. And so, I spent a lot of time thinking about what would I not let happen. What would not feel right to me. And one of them was if any of our employees lost their jobs through no fault of their own or if suddenly our customers couldn’t use the product. Because a lot of people are invested in this app, time and money, and I didn’t want that to happen. And, luckily, Clay and the Leadpages teams was totally on board with that. The whole point was them acquiring it in order to grow the product itself. They want to add more customers rather than shut it down.
And in order to add more customers, you need the team we have in place. Because even though they have a team, ours is specialized in Drip and we know, we have years of experience working on it and experience in the space. And so, that was something that I thought a lot about early on.
We’re fortunate that we’re in a position where I was approached by many potential acquirers. It wasn’t a few, it wasn’t several, it was many potential acquirers over the course of the past two years. And so, I wasn’t going to sell to someone who was going to do one of my deal breakers, who was going to go against that. And so, it was really cool that Leadpages was on board with that and, specifically, Clay was very supportive of that.
So, that kind of sets the stage of where I was coming from. The point of this acquisition is, I think it’s going to mean we can release more features faster; scale our infrastructure faster; and, even within the first couple days after this acquisition, we made a bunch of improvements to the acquisition in terms of doubling server capacity and doing all the stuff that we didn’t have the money for before. We’re bootstrapped, we’re profitable, but very cash limited as a result of growth. Typically, growing companies don’t have a lot of profit and that’s why companies raise funding is to help them manage this growth and scale and do all that stuff.
And so, it’s almost like being acquired by Leadpages allows us – you can think of it almost as we got funding through this – it’s like this indirect funding round without having to go through the funding rounds and all that stuff. We now have more budget to do interesting things. And there’s a bunch of stuff in the works. I can’t talk about that right now, but there’s a bunch of stuff in the works that we just plain did not have the budget to do.
And so, the goal of this – again, my deal breakers were: can’t hose our customers, can’t hose our employees. And then the goal of it – those are the negatives that I wanted to avoid – and then the upside or the goal of it was let’s grow this thing faster. Let’s build it bigger. Let’s do what large funding and large team can do for a product like ours, even though I personally and Derek as well, didn’t want to go out and raise a round of funding.
Mike [12:28]: So part of the goal of this acquisition was really to allow you to create more features faster and scale the infrastructure and provide a better experience and better product for the customers. That’s kind of what you’re getting at with what they can expect.
Rob [12:38]: That is the goal. And I don’t want to sugar coat it. It’s easy for someone to say, “Oh, we got acquired and everything’s going to be great!” I really do believe that and I wouldn’t have gone through with it if I didn’t, that kind of thing. I’ve done enough of these. I’ve built enough products; I’ve bought enough; I’ve sold enough that it was the opposite of a desperation move. If that makes sense. I genuinely believed the entire time and I still believe that this is – this or getting funding – was probably the right next move for Drip for it to be the best product it could be for our customers.
Mike [13:09]: Couple of things that you mentioned earlier were that there’s different types of acquisitions that can happen where – you mentioned Microsoft as an acquirer for Sunrise and they bought it and then shut it down. I think that there’s different viewpoints for that where a company will come in and they’ll just buy a product or a technology specifically for that one small piece that they want to integrate into a much larger suite of products that they have. And then they stop selling it as an individual product because they want to sell it to the suite and they want to sell it to enterprises.
And it’s interesting that this was much more of a boxed purchase, I’ll say, where they wanted the entire container. They wanted everything in it and they want to say, “Okay, let’s plug this entire block” as opposed to, “Let me just grab this one small piece of it or these ten people over here because that’s what important.” It sounds more like it was, “We want everything.”
Rob [13:53]: Yup. And it kind of makes sense if you think about what they’re up to. Leadpages announced publicly that it was, what 18 months ago or 2 years ago, they raised a big round of funding. It’s on TechCrunch, but I think it was 27 million or 30 million or something. And they said this is for strategic acquisitions. And so, it’s not a surprise that they would buy an email marketing company.
Mike [14:11]: Let’s talk a little bit about the timeline itself. I’m pretty sure you can talk about this because I saw it on Facebook and it wasn’t you that posted it, I don’t think. It was a screenshot of an email that Clay Collins had sent to you and it included the date, which I thought was interesting. So let’s talk a little bit about the timeline because right now it is July 13th of 2016. When was that email sent?
Rob [14:37]: Yeah, Clay’s first email was early June of 2015. So it was 13 months ago.
Mike [14:42]: So, it took 13 months for the acquisition to go through. Now was that 13 months of negotiation? Was it 13 months of legal work? Was it three months of this, six months of that? What does that approximate timeline look like?
Rob [14:45]: Yeah. The cool part about this is from all the research I’ve done and the reading and the talking to founders – I’ve talked to several founders who have been acquired. As soon as this started ramping up that’s where I went, was to try to get myself educated on this process. And the neat part is, my experience here or our experience getting acquired, I think is fairly typical. It tends to take a long time. It’s the dramatic exception to the rule when – again, Facebook buys Instagram for a billion dollars over a weekend – that just never happens. That happens once a year, once a decade. It’s just completely anomalous.
So for you to hear an announcement that Leadpages acquired Drip, everybody probably saw it on Twitter a couple of weeks ago and thought, “Well, that came together fast.” It actually was, again Clay emailing me 13 months ago, we emailed back and forth casually for a couple of weeks and then just kind of nothing happened. It was just radio silence. And then, I think it was in September/October, something else came up where we started talking again. And then it kind of just trailed off. We never got to a point where things got serious.
And then, I think it was November/December, things got serious again. And then we started talking more about some detailed points and how things might look. And you really started getting into the nitty-gritty. And then, eventually, there was another four or five weeks of silence. And so, it wasn’t until really until late January where things ramped up in a way that I would call active negotiations from then on.
So it was probably five/six months of pretty heavy negotiating. And I guess, to put a spin on that, it was more like three to four months of negotiating and then, the way it works is you sign a Letter of Intent. That’s what you’re negotiating upfront. And then you sign the Letter of Intent. And then you have due diligence which can be anywhere from – for companies it’s 45 days to 90 days or 120 days. They could be pretty long. As the seller, you want the shortest due diligence as possible and typically the buyer wants the longer one. But the range for startups our size would probably be 45 to 60 days.
And so, that’s when you get legal involved. It’s less negotiation. There’s still negotiation going on but it’s a lot more of like contract negotiation where you’re not negotiating these high level terms. You’re actually negotiating sentences and paragraphs in contracts. You’re trying to negotiate liability and who absorbs what liability where.
So that gives you an idea of how long this takes. And it seems like how could this possibly take this long? That’s really the question that came to my mind when I would hear these stories about – how can it take six months of active stuff? When I hear people saying it took a year, it’s like, yeah, but the first six months is really not that much time. But how does it take four, five, six months to close a deal? And now I understand.
Imagine you sell your house and there’s stuff going on constantly. There’s contracts going back and forth. And think about how much is standardized in a home sale. How that entire contract from the Realtor’s association is just done and everybody, generally, agrees on it. You don’t go through and read every sentence and red line that contract and go back and forth. Well, that’s what happens with acquisition because there are no standards. Nothing is standard. And so, every sentence and every deal point and every contract is essentially created from scratch. I know they use boilerplate and everything but they’re negotiated back and forth from scratch by the lawyers and the people involved. That’s why this stuff takes a long time.
And it can also take a long time to arrive at – you think about one point is price. And that’s the one that everybody puts on the press release, “It was acquired for this much.” But there are hundreds of other points to negotiate. It’s like, does the team stay on? Does the team have to move? How long do the founders have to stay on if at all? Well, what about stock options? Is the price paid all cash? Is there stock involved? What happens to different assets? Is it an asset-only acquisition? And it it…? On and on and on, and all of these things. That’s what takes the time, is negotiating and then once you’ve negotiated and the founders on both sides have shaken hands, it’s like, “Alright, those are the terms.” Now the lawyers get to put that into writing and that literally takes another couple of months just to sort that out.
Mike [18:48]: I remember talking to my attorney at one point about a couple of different contracts that we were working on and I distinctly remember he looked at one particular line. He was like, “That’s interesting. I’d never agree to that but let me put that in as boilerplate in some of my other contracts.” And it’s just interesting that because there aren’t really any standards to those agreements people are just kind of going on what other Edge cases or exceptions they’ve seen. And that’s really where a lot of these contracts come from, it’s like the Edge cases and the exceptions and the ways that different customers or – I don’t want to call them opponents – but people on the other end of the contract agreements that they have worked on have gotten screwed. And it’s just a matter of trying to figure out how can you get the best deal for the person who you’re working for and minimize the downside for it?
Rob [19:32]: Right. As well as be reasonable because there are certain things that you’ll throw in a contract and, in a perfect world, that would remove all liability and risk from you. And the other side would be insane to accept that. And so, at a certain point, both sides accept some time of risk, some type of liability. I mean, I’ll throw some crazy things like, what if we get into this and suddenly Rob gets killed, Rob dies from something? What does that mean for this whole thing? What does it mean for the deal and subsequent payment and all the terms of everything? It creates complexity and you have to sit down and think about that and talk back and forth. What does that mean for my family? That’s the kind of thing that lawyers have to think about. They’re anomalous. They’re not likely to happen. But if they do it sucks if you don’t have something in place to deal with that.
One other thing I want to add is throughout the timeline – and this probably a topic I will dive more into with Sherry over on ZenFounder – is I’m making it out like, “Oh yeah, it was a year and then five months of that was hard negotiation or whatever.” It was one of the most stressful things I’ve ever done. You’ll probably hear this over and over from people who were acquired. It was extremely stressful. And at the beginning I was able to continue to do my day to day work and run the company and do all that. Towards the end, it was pretty much my full time job. It was between 30 and 40 hours a week of what I was dealing with.
It’s really nice, to be honest, that I have the team that I do because those [?] were able to keep the company running. I just didn’t have the focus to push things forward and it was cool to see things still being pushed forward even though I was involved in a lot of phone calls; a lot of meetings; and a lot of getting documentation for the acquisition.
Mike [21:09]: One of the pieces of feedback that I had heard actually at MicroConf was there were several people who would listen to your talk at this most recently MicroConf back in April that they saw the talk and they said, “Oh, I’m a little disappointed because I’ve been watching Rob’s talks over the years and every single years he’s talked about the numbers and the snapshot of where he was at. And this year he didn’t.” Is that why?
Rob [21:33]: It’s interesting. It wasn’t why. I suppose it was probably good that I didn’t share revenue. But that was not the reason. The reason was – there were two things. I don’t like talking about revenue specifically. I don’t like sharing it. I feel like maybe that’s a whole other podcast. But the transparency thing can cause problems. And the people who are all into the transparency, I think you may want to go listen to the episode that I recorded with Josh Pigford a while back and how transparency came back to bite him in the butt. And it can bite you in butt in a lot of ways. One it can bring in competition who can much more easily replicate what you’re doing. Two, it can result in you not raising funding, VC’s – I’m not saying all of this are like this – but I know that some funders and some VC’s they don’t want all your metrics public. And it can impact acquisitions. Some acquirers do not want all that history up online.
And so, those are the reasons, to be honest. The reason for me was because stuff that I’ve released in the past couple years, intimate details of Drip has been – how do I say this? It has been commandeered and used to replicate what we’ve done and compete with us. And that had never happened at this scale. And so when I had HitTail or when I had these little businesses, DotNetInvoice, if people competed with me it didn’t really make that much of a difference. At the scale of Drip where we have ten people working on it and I’m paying people’s mortgages, the stakes are much higher.
And as more things started to come about that it was obvious had been used based on things I’ve been teaching and intimate details that I had exposed, I made a decision to do that less and to be a little more guarded about it. And I had long conversations with folks who are respected in the startup space and asked them, “Hey, why don’t you share this?” And they had similar stories of, yeah, I did that and then this happened.
It can happen to you eventually. That’s not a reason not to do it but it was my reason not to do it. I had hit the point where it made more sense not to share the revenue than it did to share it. And, in fact, at MicroConf I did give kind of a revenue range and said how many employees. And you can tend to figure that stuff out anyways. But, no, I didn’t give the big revenue graph. And there was definitely a thought process behind it.
Since I didn’t, like I said, I actually think that’s probably better in terms of the acquisition. It didn’t complicate things, but it probably wasn’t a major factor. I don’t remember it being a major factor when I put my talk together.
Mike [23:46]: So let’s move on a little bit to the thought process behind selling Drip. Because, obviously, there’s a lot of consideration that you need to put into the different components whether the employees are going to stay on or not; whether they’re going to move with the company. I think one of the biggest considerations is your family. Because you said that this was probably the most stressful thing that you have ever gone through. And I would imagine that it’s probably more stressful than selling your house. Because selling your house, hopefully, would only take a couple of months and once you find a buyer you can generally get those things straightened out in a month or two.
But with selling your company, that was 13 months of back and forth and ongoing stuff and you probably weren’t sleeping well near the end. That’s got to have some kind of an impact on your family. And in addition to that, there’s considerations for your family afterwards. So, can you talk a little bit about what role your family played in the acquisition and whether there were active discussions about it. Was there a lot, a little bit? Were they involved early, late? Talk a little bit about some of those things.
Rob [24:43]: Yeah, sure. There’s a lot to consider there. It was stressful and it definitely made me less pleasant to be around, as stress will do to most people. And that was a bummer. I think Sherry probably has a lot to say about that. I mean, if you’ve ever been through a really stressful time for an extended period of time, it changes the way you feel about the world and about yourself and about people around you. And it just puts you in a bad place. You can be in a bad place mood or whatever all the time. I don’t feel like it was that constant until closer to the end where things just really ramp up and they get really serious. It was something that I knew was a season.
Some people, when they’re just growing their startup, that’s how their life is. And they’re stressed all the time just building the company. I would not sacrifice myself for my company that way. I know founders personally who put on a lot of weight, as an example, because you’re so stressed and just eating like crap and they’re working all the time and they don’t have time for exercise. I know founders who’ve had divorces due to funding their company. I know founders who developed health problems and ulcers and that kind of stuff. And that has never been something I’ve been willing to sacrifice in order to grow a company.
In order to sell a company, I think that you are going to need to undergo a tremendous amount of stress. I think if you don’t undergo a large amount of stress, then you probably didn’t negotiate hard enough, is kind of how I feel. But I knew that there was a timeline to it. That was the thing. I knew that it would have to end within a few months. It did take longer than I had hoped but it did eventually close. And I had to be honest, the weight that lifted off my shoulders when that happened was tremendous. It wasn’t the same day. I remember it being surreal and just being totally in a daze for a few days. But the following week, as we started ramping things and I realized,boy, all that’s done and I don’t have to think about that anymore, my demeanor and my whole outlook changed. And I became back to normal is how I think about it.
So, there were definitely family considerations there. I had a lot of conversations – I had just a few conversations with Sherry early on and then as it got later and later and more stuff was being decided, especially – There was a decision at a certain point and like is it a smart decision to move to Minneapolis, which is where Leadpages is based. So Drips in Fresno, Leadpages in Minneapolis. There was genuinely a conversation of what is best for the long term play out of this deal. What makes Drip a success and what makes this acquisition a success for Leadpages. And so Sherry and I had a lot of conversation about that.
It’s funny, I think some people go into negotiations and they think, “I want to get everything for me, as much as I can. And I don’t care about the other party.” And I don’t go into negotiations like that. Maybe if you’re negotiating for a car, then yes. You just want the highest price, they want the lowest and you go. And you’re never going to see the person again. You’re never going to work with them again. In an acquisition like this where you know that you’re going to be working with that team and you respect that team and you respect the person on the other end, it’s less about maximizing everything in your outcome and it’s more about, in my opinion, maximizing the deal. Maximizing the benefit of this for everyone. And obviously you have your certain minimums, you probably have a minimum price. You probably have some minimum deal breaker terms – I won’t shut the product down, I won’t let the product have crazy features added to it, I won’t let my employees be fired.
But aside from that, it’s like the decisions of should we move and should the employees move were things of what’s best for the deal. And in the end we decided to move and the rest of the company totally had a choice. None of our employees had to move to Minneapolis and everyone was brought on as an employee of Leadpages. Some folks have decided to stay in Fresno or where they are, because we have remote employees. We have a guy in the Bay Area and a guy in New York. And then other folks made the decision that they wanted to move to Minneapolis. They ‘A’ thought Minneapolis was cool or ‘B’ thought being at Leadpages HQ would be a cool experience.
And so to go back to your original question, yeah, the conversations with Sherry were super helpful. Derek as well. Being my co-founder he and I talked a lot about deal terms. I talked a lot with FE International. David from FE was the broker on my side and he gave Derek and I from the broker’s perspective because he had been in investment banking and had done larger deals and so he had a lot of experience with that.
And then talking with Sherry was more about the mental side and it was about stuff that impacted the family because certain things did and certain things didn’t. Certain parts of the deal did and didn’t impact the family. And so, she was definitely helpful during that time for helping me keep a sanity check on things. Because you get so far into this deal and you get a certain lens you’re viewing everything through and it’s helpful to come out of a deal and then have a conversation and say, “Look, this is the situation. They’re asking for this. This is what I think.” And for her to say, “Oh, yeah, that’s totally reasonable.” Or, “No you’re way off base.” It was helpful.
Mike [29:16]: You mentioned that you’re going to be moving to Minneapolis and some of the members of the team had the option to also move. I would imagine that every single piece of that was probably negotiable. Because when you’re talking about an acquisition because there aren’t really standard terms for that stuff, some of that stuff probably could have been negotiated upfront for people or you probably could have gone back to them and asked them, “Hey, would this be okay with you?” But also, you’re looking at it from a holistic perspective of what’s best for the deal; what’s going to be best for the employees; and what’s going to be best for the company moving forward to be able to still do kind of what its core mission was. But the core question there is really is all of that stuff generally negotiable or is it something that you think that other companies might come in and say, “Hey, these are our terms, kind of take them or leave them”?
Rob [30:01]: Yeah, I think it’s going to depend on the acquirer and their goals. To answer your question, I think everything is negotiable and I just think that there are going to be certain deal breakers that certain acquirers have. Where maybe they say, “It is an absolute deal breaker if everyone does not move to our headquarters.” And then, as the founder, you have to decide is that something I’m willing to deal with? Am I willing to kind of force my employees to move and if they don’t then essentially they get laid off? That wasn’t something Derek and I were willing to do for sure. And the cool part, Leadpages never even asked because that wasn’t in their best interests either.
And that was a cool thing. Again, if you’re in a financial acquisition there is some alignment there but I think with a strategic there can be a lot more alignment and our goals for growing Drip and making it the best marketing automation, lightweight marketing automation app was in line. And we both have that goal still. A lot of that wasn’t hard negotiation. It was like, “Hey here’s what I think would be the best. The employees have the choice and it they want to come they can and if they can’t – some people just can’t do it due to family situations or whatever – then they don’t.”
That was a super easy point. It wasn’t even a back and forth because it just kind of was a no-brainer for keeping the company together. We already have remote people. It just made sense. But I can imagine getting into negotiations and having that be a complete deal breaker with the acquirer. And you’d have to ask yourself the question of are you willing to do that. And, again, for us, that would have been a deal breaker. That would have been an okay, we can’t do this deal. And so, if you have the luxury of having multiple acquirers who’ve approached you or if you’re talking to multiple at once then you can pick and choose the deal that works best for you.
And that’s really the position you want to get yourself into, is where there are multiple people because then you can stick to the terms that are most important for you.
Mike [31:48]: As you were talking through there, one of the things that came to mind was, I saw a talk by Eric Sink back in, I don’t know, it was 2011 or 2012 at the Business of Software. And he had talked about how sold his company, Teamprise, to Microsoft. And there’s a lot of parallels that I can draw from my mind from his talk to what it sounds like your experience was. It doesn’t sound like there was anything necessarily out of the ordinary.
Rob [32:12]: Yup. There’s a good podcast I’d recommend. If you are thinking about selling. There’s a good book called ‘Built to Sell,’ get that on audiobook it’s a quick listen. And then there’s Built to Sell radio which is where the guy who wrote that book interviews folks who’ve been acquired. And so there’s a bunch of stories of these real acquisitions. These are not the Instagrams and the billion-dollar blah blahs that are on the front page of Inc. Magazine or whatever. These are the more realistic ones where it’s a manufacturing company or retail company or service company or a tech company – there are tech companies in there as well. And those stories will really level set you for what’s more realistic. And in listening to those, that was also my experience, that Eric Sink’s discussion and then that our acquisition here of Drip was fairly typical in terms of the things that you have to sort out.
Mike [32:57]: So, I think I have probably two more questions for you. The first one is that you had mentioned that you’re going to be moving to Minneapolis to essentially work for Leadpages as part of this. So, what you said before was, the entire team is staying on and you’re sticking around with Leadpages. What sort of career considerations does that have for you? How do you justify going to work for somebody else as an employee after having been an entrepreneur for what, 10/15 years?
Rob [33:22]: Yeah, that’s a really good question actually. And it’s certainly one that I thought about. The one plus of having all this stuff take so long is you just have a lot of time to sit and reflect. You have a lot of time to think about what’s important to you and what you really want out of the acquisition and then out of post-acquisition. Because, that’s the thing, it doesn’t end at acquisition unless you walk away. And most founders do not walk away right at the end, either because they are required to stick around or because they want to stick around. Because, again, for the success of your product, there has to be some kind of hand off time frame. Can you imagine if the day that it closed, suddenly Rob and/or Rob and Derek were just not around Drip anymore? How would that work? I would have serious fears that things could go off the rails pretty easily. Like the wheels could fall off the cart because the two people who’ve been there since the start are suddenly gone.
Anyways, that’s how I think about it. I think for the long terms success of this, both Derek and I have to be around at a minimum, we’d have to be around for hand-off. And it’s not to say that no one else can run Drip better than us. Because certainly there are people who could take the reins from us at any time and be able to grow it. But the idea of the acquisition is probably shocking to some customers anyways and to hear that the founders also walked away would be a little jarring.
But I think, coming back to your question, which was how can I go work for someone else? The interesting thing – I talked to Clay about this, and I gave a lot of thought to it. Derek and I also went and visited Minneapolis and checked out Leadpages and the first thing is Leadpages is a pretty cool company to work for. And I’m not just saying that because I work there or because I’m going to be trying to hire engineers to work for us at Leadpages. But it’s just a fun environment. It’s not the crappy environments that I used to work at. You work for certain companies and it’s not very fun. You’re there either for the paycheck or the pension or whatever.
It was pretty obvious to me from our visit and from folks that I talked to because I knew folks who had worked there – who work there currently or had worked there – it’s a pretty fun company to work for. And so I figured company-wise I’ll be fine because I don’t have a problem playing well with others. I just never like working for companies that had a lot of red tape and, I don’t know, bureaucracy and politics and that kind of stuff.
And based on my conversation – you know, a lot of stuff comes from founder down or from CEO down – and in my conversations with Clay it was pretty obvious he wants to run a lean organization. I like lean, I like moving fast even though their company, now with the acquisition of Drip, they’re 180 employees, they operate like a smaller company. There’s way to stay lean and to keep moving fast because that’s the fun part. And so, that’s why where I saw it as a company-wide thing. In addition, I’ll continue to work with Derek and my whole team, who I really like. I mean it’s the best team I’ve ever worked with. And I’m able to work with Clay and, then there’s folks on the inside there. And everybody that I met, I really liked. And Derek felt the same way. We’d come back and I’d be like, “We met two or three people today and they were awesome. I would have no problems working with them.”
That’s always been my deal of working with people I don’t like. I don’t do very well with that. Working with people who aren’t on the same trajectory or have the same ferocity of getting things done. That always bothered me. And just the more people we met it was like, “Oh yeah, I cantotally work with this.” The other cool thing that wound up out of this was it wasn’t like Drip was going to be swallowed out and we were going to be distributed throughout the company where suddenly our engineers will report to the head of Leadpages engineering and our support people report to the head of Leadpages support. We got to keep the team together in essence, even though obviously we all work for Leadpages I still get to work very closely with the team.
And so, in actuality, not very much is changing here. Like me working for someone else, you imagine having this slave driving boss that’s like – I think Clay and I have this mutual feeling of we view each other more as colleagues. Just like Derek and I. I hired Derek as a contractor and then as a W-2 employee and then he became co-founder of Drip. But I’ve always viewed him as a colleague rather than some type of employee. And actually everyone on my team, if you ever hear me talk about the Drip team, when I introduce them at MicroConf or whatever, I always say, “Anna and I work together.” “Zach and I work on growth for Drip.” You’ll never hear me say, “Zach’s my employee” or “Zach works for me.” It’s just not how I think about things. I know in bigger organizations you need hierarchy and you need that stuff. That’s not how I personally think about things.
And so the cool part is it seems like Clay does as well. And so, all of our conversations it’s never been I’m going to be reporting to some backbreaking boss who’s making decisions that I don’t agree with. These are all things that have happened to me and all the reasons that I didn’t like working for other people. I like to frame questions. I realize this, I try not to be dogmatic about stuff. So I don’t say, “You should always bootstrap. You should never take funding. You should never sell your company.” That’s just not the way I think. And when people say that it bothers me because I don’t believe that’s the case.
I like to ask myself instead, I like to re-frame it, under what circumstances does taking funding make a lot of sense? Under what circumstances would selling your company make sense? Under what circumstances would working for another company make sense? And the answer may be never. There’s no circumstance. But I believe that there are circumstances where maybe you’re autonomous and you really believe that long term it’s the best thing for your employees and your customers. And you believe that you can be part of something really cool. And maybe there are other factors. For you maybe it’s a big salary. Maybe someone throws a bunch of money at you and that makes sense. Or they give you a ton of stock. I’m just throwing things out here. Any of these could be factors, but I think instead of thinking, “Boy, I’m an entrepreneur. I could never work for another company.” It’s like really? What if your boss was awesome and everybody you worked with was really cool and you didn’t hate the job and you got all these perks and the safety of this and that and healthcare and 401K and things you haven’t had for a long time?” I don’t know. There’s other factors into it and so I asked myself these questions. And I sat there in front of my notebook and I wrote all this stuff down. And as it turns out, it just made a lot of sense.
Mike [39:05]: Well, a lot of what you just said there kind of leads me to my last questions which is you probably had a choice as to whether or not to sell the company or to go out and raise funding. And, obviously, being in a position where you were profitable and you were growing the company, you kind of had that option. It wasn’t like your back was against a wall and you had no other choice. You actively chose to pursue the path of selling the business versus going out and raising funding. Why did you do that?
Rob [39:25]: That’s a good question. You are absolutely correct. I mean, aside from the cold emails that I was getting I’ll say maybe on a weekly basis – I don’t know if it’s that often but it’s pretty frequent – from venture capitalists and people looking to invest in equity funds and that kind of stuff. I have a network of people who are into startups and have money. I genuinely believe I could have raised an angel round or a seed round very quickly without a lot of hassle. And so that was something that we evaluated. Derek and I had conversations about that. Because, again, I never say you should never take funding. There are times when taking funding is a really good idea. If you’re growing fast and you know that putting a dollar in here gives you $2 or $3 on the other end and you want to grow and get big, why would you not? There are times when it makes sense.
And so, we evaluated that. And that was not off the table. We may have raised a round in the next six months, twelve months or whatever. There are some things to think about. It’s interesting, once you raise funding, you’re funding valuation is going to be tend to be higher than your acquisition valuation. So let’s just say you could raise funding at a $20 million valuation. You’re probably not going to be able to get acquired at $20 million today. It would be anomalous. It’s going to tend to be – I don’t know the numbers- probably half as much or a third as much. People actually writing you cash for a company versus giving you money based on funding valuations, they’re very different.
So, let’s say you did raise at a $20 million valuation. You can’t sell that company today for $20 million because the funding valuations are really high historically speaking. So as a result, once you take that funding you now have to grow the company to reach that valuation in order for your investors to even break even on their investment. So, if you raise funding you are signing up for three, five, seven years of just hammering on and growth and definitely growing headcount because that’s going to be a big part of why you’re raising the funding.
And so that was a question that Derek and I kept asking ourselves. Do we want to go down that road? Do we want to sit here and plan to go three, five, seven more years and to grow the company because we’re at ten people? On the trajectory we’re at, we’re going to be at 20 people on then 30 people. It’s kind of the natural way you have to go. In addition, there are situations where you do that. You raise that funding. You don’t take funding off the table. You don’t put that in your personal bank account. That goes into the business to grow it. So then you can go that three, five, seven years and if you get killed, if you go out of business, if you get acqua-hired at the end – because some acquisitions really are just a failing company and you get pennies on the dollar- if any of those things happen, you’ve spent many years of your life and basically walked away with almost nothing. And you could spend all that time grow a big business and walk away with literally nothing or hundreds of thousands of dollars which would completely not be worth all that effort.
So there is an advantage, if you get acquired at the price you want, essentially, that makes sense and the terms you want because price is just one of them; and you could also kind of have that funding. Like I explained earlier, we have the advantages of having these extra resources but there was also a fit for us in terms of the terms. And we are able to take money off the table. I actually want to quote Jason Cohen here, who I’ve long respected. He wrote a post called ‘Rich Versus King in the Real World: Why I Sold My Company’. And there’s a quote from it that I think is fascinating. It’s a really good post and it impacted me. He wrote it seven years ago, it was 2009. And just to add a little bit of context, to be king is to kind of run your own company forever and be king of the company. To be rich is to sell it and have money to live for the rest of your life, in essence.
And he says, “See, it’s good to be king but what do you do when you’re at Trudy’s North Star TexMex restaurant tucking into a chili relleno and the guy across the table looks you in the eye and offers you enough money that you never have to work again.” And it’s an interesting thing to think about. There are many paths here. And there are a lot considerations. And you’re going to have a lot of time to think about these things if whether from now until you get acquired or even if you’re in the acquisition process. And that’s probably a question that Jason Cohen just asked that you’re going to wind up asking yourself someday.
Mike [43:18]: I actually remember talking to Jason Cohen at a MicroConf over dinner once and he had talked a little bit about that. Because I told him, “Wow,” because he had mentioned that particular quote in his Business in Software talk. And he said that he had, basically, personal experience with going through that and he knew somebody who said, “Well, let me hang onto my company a little bit longer and grow it a little bit more.” And six months, twelve months later they were completely out of business and were left with completely nothing because they had chosen to go that path.
And I could see that happening if you decided to go get VC funding or angel investment or additional funding of any kind and then you grow it or something happens to the economy and everything just goes out the window. And then you’re left with nothing versus the situation he was in where I’m going to “take the money and run” but it was more of a calculated decision to, essentially, put himself in a situation where he wouldn’t have to worry about money in the future. And there’s really only so many opportunities that each person’s going to have to do that.
Rob [44:18]: That’s right. There are definitely limited opportunities to be able to do it. And the interesting thing is – I’m not even talking about, let’s say maybe you don’t run your company completely into the ground or you don’t get swiped by a competitor and go to zero. What if public SaaS valuations, as an example, they drop 57% earlier this year? There’s a Tom Tunguz article talking about public SaaS valuations and that does impact that ripples all up the chain. Because then venture capitalist’s valuation goes down, then acquisition values go down. And so, what it just that happens? Because right now there’s pretty frothy, there’s talk of bubble, there’s all that stuff.
I’m not saying there is or isn’t but per your own judgment what if we are hitting peak SaaS and things are going to come down on the other side and you can sell for a great multiple and get the terms you want? There’s something to be said for the bird in the hand. What if even broader? I’ve lived through several recessions. I remember the recession of ’93, it was a real estate recession. There was 2000, the dot com bust, 2008 housing bust. It’s 2016.
Again, I’m not saying that something’s coming here in the next six months or a year, but we do travel in cycles. The economy is a cyclical thing and we will have another recession. We will have one. Period. It’s just a fact. The timing is what’s in question. But for you to think that you can continue growing your company forever like it’s growing today, I believe is foolish logic. Because you are going to hit – let’s say a recession hits us sometime in the next three years. Those recessions can take a long time to pull out of.
So, again, you just have to ask yourself are you in this for the long haul? I did hear stories of several founders who didn’t sell – they got an offer, they didn’t sell, they decided to grow it – and then then they sold later but at half the price. So it wasn’t that they got nothing but they definitely felt like they had run their business over the top. And, again, I’m not making a comment on Drip. I don’t think it’s gone over the top. I actually believe that we’re going to – and I’ve already seen it – stuff’s starting to accelerate and everything’s continuing to go up and to the right. But I think this is something that the people don’t really think enough about in our space.
People get the vision of this founder who just goes and starts this and they’re just all about not selling their company. And so they look at Mark Zuckerberg. He started and never sold but it’s like, “Yeah but he made buckets of money from it. And he’s set for life, so he doesn’t have to worry about that.” And even like, let’s say Basecamp – formerly 37signals. They’re often brought up as an example of a company that they bootstrapped it and then they just run it forever. There are very few companies like that, by the way, that either don’t get really big, don’t get killed or get acquired. And Basecamp’s one of the few examples that I can think of of a company that’s not just on autopilot. Not some SaaS app someone has sitting on the side but an actual company with people working on it. It exists but it’s rare in a frothy space, I’ll add as well. Because if you’re in a niche, I think of like Moraware software. They are profitable in steady state but they’re in a very small niche and they kind of own the whole thing and it’s different than being an email marketing company where there’s 500 of them.
If you think of Basecamp as the counter example, even them, they got their big take home money when Bezos invested in them. He wrote a check, and I think it’s estimated – I don’t know if it’s public – but it was like $10 million or $20 million. And DHH said on an interview a while back, that was when he got his eff you money in essence. And so for them, to stick on, that makes sense. They were able to take that money off the table. And so they have different concerns then you or I, where you’re sitting there thinking, “I this fails, I’m back to square zero. I have to start something completely from scratch again after all this work.”
And it is, I think, a real concern that the folks should at least keep in mind. I’m not saying you should always sell if that happens or the economy’s going to hell in a hand basket or any of that stuff. But you have to ask yourself these questions, I think. And I don’t think they’re asked enough kind of in the mainstream press. And I think people have this romantic view that you’re going to keep your company forever or that everyone should be in it forever and I don’t think that’s the right way to think about this. I think there’s more realities that need to play into this.
In terms of Jason Cohen’s thing, he talked in that post also about he has enough money to pay for his kids college, to never have to work again. For everybody to be financially secure and like, that’s a good feeling.
Mike [48:19]: That’s the ability to buy your freedom, so to speak. Eventually, the longer time goes on, the more you’re rolling the dice. And, just like Vegas, eventually a house wins. Eventually, you’ll get hit by a bus or you just grow old and you’re not able to effectively run the business anymore. You just don’t want to or the economy goes down – there’s lots of things that can happen. So it’s a matter of risk versus reward. And when do you want to take the money off the table.
Rob [48:42]: Right. And some people do. MailChimps is an example of a company that just kept going. They never raised funding and they’re huge and they’re awesome. I really like Ben Chestnut. I have a lot of respect for him, the founder. And he has stuck with it for long term and they have seen all the recessions. Well, I guess they started in 2007 – so they saw the big 2008, 2009 dip and they’ll weather it through and they’ll be fine. And Ben will probably run that company until he retires. So there are going to be some exceptions to that. But I guess, from what I’ve seen, those are the rare ones. And he was able to – they got profitable. So, obviously, Ben Chestnut, as an example of probably doing really well for himself.
Mike [49:15]: But as you said, that’s an example of an exception and it’s not necessarily the general case rule. And I think that that’s something that people need to pay attention to when considering the risk versus reward for selling the business and taking that money off the table and setting up yourself and your family for the financial freedom. That’s part of why entrepreneurs do what they do. They want to build something for themselves and essentially profit from it. And if you don’t make the decision to do that at some point then what was the point?
Rob [49:44]: Yeah, there’s a lot to be said of that. A closing thought for me is, there’s a lot of considerations if you’re even going to evaluate this as an option. And I think the question to keep in mind is what are your true deal breakers. Not dogmatic stuff you’ve heard or you think always/never. What really are your deal breakers? And then, what is the ideal outcome? And if you can get pretty close to that ideal outcome where the terms of the deal make sense and you wind up really feeling positive about it at the end, I think that’s super important.
And I do. I guess, I’ll summarize by saying it’s been about two weeks I think since the deal closed. And I can say in all honesty, it has been really fun. I’m meeting a lot of cool people. Starting to just get work done, getting things done really quick. We’re ramping up hiring. We’re doing all the things that were harder to do as we were trudging along and I just feel like I’m excited. I’m optimistic about the future and I have a sense of personal calm that I haven’t felt in a long time. Because, of course, going through the acquisition it was – I wasn’t calm for even a few minutes at a time during that.
And so, I think that’s what I would advise someone, don’t take what the press has shown you. Try to be realistic about it and ask yourself what are your deal breakers and what are you really looking for out of all of this.
Mike [50:59]: Well, Rob, thanks for sharing the experience with us. There’re certain things that you can’t talk about but I think that everybody really appreciates the things that you have been able to talk about and the general process and things that you’ve learned going through that.
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