In episode 612, Rob Walling chats with longtime friend and repeat podcast guest Dave Rodenbaugh. Dave was even at the very first MicroConf back in 2011.
In this episode, we have a candid conversation on our experiences balancing side projects with a day job, struggling with the decision in our own different ways of when to quit, and the surprising habits you have to unlearn once you are finally independent of the day job and consulting work.
Topics we cover:
[1:27] Dave’s thought process behind expanding Recapture
[5:34] The decision to go full-time on Recapture
[15:05] Dave’s process for unlearning bad employee / consultant habits
[20:07] The danger of the arrival fallacy
[24:20] What would you do if you sold the business?
[26:03] Balancing a side project with your day job
Links from the Show:
If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you.
Rob: Welcome back to Startups For the Rest of Us. I’m Rob Walling. Today, I talked with longtime friend and friend of the show, Dave Rodenbaugh. We talked about both of our experiences, balancing a side project with our day jobs. We talked about that feeling of finally being independent.
Dave has been independent from consulting for about a year. We talked through what was surprising for him and not, and I share the same thing. This is a very much more collaborative conversation than an interview.
Since Dave and I have known each other for more than a decade now, he actually attended MicroConf 2011, the very first one. He’s one of the handful of folks that are still around in this community who’ve been going to MicroConfs for more than 11 years now. Since he and I know each other so well, the conversation flows.
I feel like it’s candid. We give some authentic thoughts on what it takes, or at least in our experience, what it took working nights and weekends balancing that side project with a day job, and eventually struggling with the decision in our own different ways of when to quit that consulting work or when to quit that day job when you may have a significant other and or a mortgage and kids. With that, let’s dive right into my conversation with Dave Rodenbaugh.
Dave, thanks for joining me on the show.
Dave: Thank you so much for having me. Always an honor and a pleasure to be on the pod here and chat with you, my friend.
Rob: It has been a while. We were actually looking through the archives trying to figure out how long that while has been. It’s just an indeterminate amount of years—six, seven, eight. Folks might know you as a co-host of the Rogue Startups Podcast with Craig Hewitt, founder of Castos. He’s been on the pod many times.
You run Recapture.io, which is ecommerce, email marketing software. It started as cart abandonment, but you have expanded into email marketing. What was the thought process behind making that move?
Dave: It was very much a land and expand strategy, both horizontally and vertically. When I saw Recapture for sale back in 2016, it was Magento only, abandoned carts, and one other feature at that point. I think it was review reminders and it had pop-ups too, so three things.
As soon as I saw that, I looked at the competitive landscape, I looked at the possibilities for places you could go, and it was pretty obvious. You can expand in both directions based on customer interests, customer demand.
As we started acquiring more customers, as we started going to different platforms, the drumbeat got louder and louder. Hey, do you do this? Hey, can you do this too? Hey, I bought this other thing that I expect on other email marketing platforms and ecommerce. I’m like, okay, great. Yes, I can do that, and I’ll charge you more for it. It works well to grow the business, it works well to make the customers happy.
Rob: Right. That’s kind of moving from micro-SaaS, which I typically define as almost a single feature with a single traffic channel, usually. Expanding from there is where you build the rest of the features, because just doing cart abandonment, you are a feature that Klaviyo has, that Drip has, or that MailChimp, any number of other tools have in addition to all this other stuff. You have dove headfirst into competitive waters for sure.
Dave: Yes, shark-infested, if you will.
Rob: Indeed, but it’s going well. Can you update folks on whatever metric you’d like to throw out, team size, progress, number of customers, revenue? Just give us some idea of where you’re at with it.
Dave: Sure. Since I bought Recapture six years ago, we’ve more than 10X the business at this point. The team was originally just me. Now it’s tripled, so there are three of us that are working on it in a dedicated more or less full-time way. We all have kind of an employee relationship at this point, so I would say we’re a real company, I guess.
Rob: You’re a team, yeah. Not just a group of contractors.
Dave: Right. In terms of customers, we’re on our way to 7000 installed customers across all different platforms out there. A significant number of those are paid. It’s grown in all the right directions. It’s come with a lot of growing pains too, like trying to figure out you’re in this competitive landscape. What does that mean? How do you carve out something that says, if you are in this part of the Venn diagram, you are perfect for our tool.
It took me a long time to really define that, articulate it, and then really start to promote it. But it’s gone well, so I’m quite happy with having been on Recapture. I went full-time a little over a year ago at this point. That was one of the milestones that I had been dying to hit for 11 years. To finally get there is huge.
Rob: I feel like I busted your chops at least once every year or two, usually at MicroConf. I would be like, Dave, you have all these products, because you had other products in addition to Recapture. You kind of had the portfolio approach, the bootstrapper portfolio.
I know what your total revenue was. Your day job was consulting and I was like, you can quit consulting, you need to quit consulting. This was me in 2015, probably 2016. You just kept doing it. You’re like, it’s just so lucrative, though. I have this day job. I’m like, yeah, but you’re grinding. Don’t do all this, just go full in.
You did finally basically go independent and worked for yourself. Your focus on Recapture is about a year ago. That’s our first topic. Just so folks know, this is more of a conversation than an interview. I’ll ask you a few questions, but I also will weigh in with my own experience on some of these questions.
You especially waited a longer time than most bootstrappers to go all in on your products. What was that decision like? What finally made it click where you were like, I’m doing this after all that time?
Dave: Oh, gosh. That’s a decade worth. Let’s see if I can condense that down into something that is less than War and Peace. You talked about those WordPress products. The problem I had with those WordPress products was the whole portfolio approach ended up with me kind of scattered in three different areas—two of which were kind of related and one of which was not.
The two WordPress plugins that I had were a directory plugin and a classified plugin. I had built those a long time ago. They were lucrative, but they had plateaued. That’s problem number one. I got them to a point where I was having trouble pushing them forward more than where they were at. They had definitely kind of hit a place where I was like, I’m stuck.
I let them kind of just sit there stuck for a while, because I was also freelancing at the time. None of those were actually a SaaS, so the recurring component of those was not nearly as strong as it needed to be. I think my renewal rates were somewhere between 26% and 33%, depending on the year and depending on what experiments I was running, things I tried, and so on and so forth, which is not great.
If you’re churning out 66% of your customers in a year’s time, that’s a pretty hefty churn rate, and definitely it’s difficult to make it a sustainable business. In the back of my mind, I was like, I got to do something with these because I built them up and I should get some kind of reward for that work, but it was clearly not the end game. That’s why I was looking at Recapture. I was trying to find a SaaS, and eventually, I found Recapture. That one was like, oh.
Rob: You wanted that recurring revenue to feel safe?
Dave: Yeah, it was the safety thing. That’s why it took so long. I never felt like I had the safety to say it’s okay to quit and that everything will be okay. It never felt like that until I got to Recapture, and then I had to get Recapture to a certain level.
That certain level was about 80% of my freelancer income, which you and I had conversations about that. I know you had talked about a similar kind of level when you were doing HitTail and even before when you had bought all those little microsites and AdSense stuff, et cetera.
They never quite made it all to that level. It was only when you got to HitTail and then later Drip that you were like, all right, all in now, I’m totally in it to win it. That’s kind of where it ended up with Recapture.
Rob: I went full time on products before I had a ton of recurring revenue. But the revenue, it was one time sale and I had a couple ebook sites, as you said, some AdSense stuff, and there were software. There was one SaaS, but it was wedding websites. It’s basically B2C, in essence, because it’s consumers buying.
I had my book and I had other stuff, but none of it was as recurring as SaaS or as predictable. Even if it was recurring revenue, the Micropreneur Academy, which is kind of the online training course, the turn of that was also quite high, because it’s going after the freelancers, indie hackers, who are trying to move into entrepreneurship.
I was so desperate. I so despised working for other people that I was willing to take a bit of a risk. For me, it was December 2008, maybe January 2009. I always forget. Right around that time was when I took the plunge. Similar to you, I was making boatloads of money consulting. It’s 2008 money and it was $20,000–$25,000 a month.
I remember quitting my day job or quitting that, basically winding down a project once my products had hit about $8000 or $9000 a month. It was a lot less, but we didn’t need any more than that to live on. It was just Sherry and I, one child at the time we were in—were we in New Haven, Connecticut or Boston? Yeah, we had an apartment or a townhouse but not… One’s lifestyle tends to expand as they get older, have more kids, and do more things.
Certainly, I couldn’t live on that now given our lifestyle. But for me, there was such a motivation to get that freedom that I was willing (I think) to take a bit more risk than other entrepreneurs do.
I remember Dave, you talked on Rogue Startups at one point, that when you were younger, was it your dad who started a business and it failed, or at some point you were really low on money or something, and entrepreneurship within that. I think there was a scarring almost.
Dave: The exact event was that my father got laid off when he was pretty close to my age now. I think he was 57, and I’m 52. When that happened, the timing was really terrible. It was my junior year in high school. We’re preparing for college.
There were house expenses and some other things that were going on. Previously, there had been some investments that went way south, like a CPA basically absconded with money from a bunch of different people, not just my father. The timing was scarring. It was a little scar, some financial trauma.
He couldn’t get another job after that. That was the hard part. That was the hardest thing to see. He sank into depression. He put all this effort into it and just was getting nothing back. It was straight up ageism.
I saw that, and it was always sticking in the back of my mind as I was working for the first 10 years. I’m like, what happens when I’m 50? What happens when I’m in my 40s?
Of course, tech is famous for ageism. I was in my late 30s and I’m like, I need an exit plan here and it needs to be something that I control, not somebody else. The main motivator was to really find something, make it mine, make it big enough, and make it something that I felt I could be proud of, sustain, and carry on when it was ready.
Rob: And that’s where entrepreneurship at the point where you’re at, I would say, is less risky than a day job because you are more in control. You are more in control of not directly in everything but how much money you make, how hard you work, whether you are fired for some random reason, whether you’re laid off because some CEO made a bad decision about XYZ and has to weigh the money when they hit a downturn. I think there’s just a lot more control.
I would say entrepreneurship in the early days is more risky because it’s super uncertain. Dave in 2010 as an entrepreneur, much riskier, but now you have the experience. You have a business that’s generating revenue.
I bring up that story about your dad or really it’s your childhood, because I want people listening to realize I was willing to take some risk, but it was calculated risk. I knew I could go back and start consulting or get a job if things tanked. Even though it’s 2008–2009, I knew that I had clients, I had people who wanted to pay me to write code. The risk to me was that I had to go back and get a day job, in essence.
I was so not liking it. I was so burned out on all that stuff. I’m just working for the people that I was willing to take the risk. But you, you listened to your own psychology. You listened to your own experience. It took you longer to get there, but that’s okay, too. We bootstrapped so we can be in control of these decisions.
Dave: Yeah. Like you said, you kept badgering me all the time. Psychologically, it wasn’t until things got so bad at my freelancing that I finally was able to take a look and say, can I actually do this now? Prior to that, I was doing some dumb things. I wasn’t monitoring my P&L as closely as I should have with Recapture. I was doing it once or twice a year. That’s bad. Don’t ever do that.
If you have a business, please, for the love of God, get your books in order every month. Have that showing up on your email or something. Do them yourself, hire somebody else to do it. I don’t care. It’s so important that you know that information all the time.
I didn’t, and I was making bad decisions because of it. But as a result of the anxiety attack, I basically suffered at my freelance client because things got so bad. I had to put the P&L together under duress to find out, can I get out of here because I need an exit plan right now? That’s what ultimately motivated it. It took me longer to get there. Similar path, maybe a bit longer.
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You’ve been on your own, in essence, for a year. I’d love to hear from you. What’s been surprising about that and what hasn’t been? Or if there have been things that are not surprising.
Dave: I would say the most surprising thing to me is how long it took me to kind of unlearn all of the ingrained habits that I had from working from somebody else. About the feeling of, oh, my God, it’s 8:00. I need to be sitting at my desk. Oh, my God, it’s 5:00. I should get the hell out of here. During that day, like, oh, I have to be here for all of these things. None of that is true anymore.
For me to suddenly be able to say, oh, my wife, Tracy and I now take Friday mornings off and we spend time together. It took me probably about four months to feel okay about that. It stressed me out when she would ask me that. Then we sat down and had a conversation, and I’m like, why am I stressed about this? She’s like, I don’t know, why are you stressed about this?
I kind of unpacked it like, I’m treating this in the same way I was treating my freelance client. I own my time. I own my flexibility here. If I’m not taking advantage of it, why did I do this? That was an eye-opening moment for me, a very surprising thing to say, my schedule is my own.
If I want to work till 4:00, great. If I want to start at 10:00, great. If I want to work at 7:00 at night, great. As long as it works for the family, as long as it works for me, as long as we’re getting stuff done and we’re moving the business forward, it’s all okay. Getting to that okay took me longer than I thought.
There might be a little PTSD from my freelance client, where it turned really toxic there in the last 12 months. Yeah, it was kind of an unlearning experience, and letting that tension go, and feeling okay with where I was suddenly at. That was the most surprising part.
Rob: I felt that 100%. That might be my most surprising as well, so I’m glad you said it. I remember that I was so hung up, because I was billing hourly. When you’re a contractor consultant, I would bill hourly. If I wasn’t working, I wasn’t getting paid. I didn’t have vacation days, didn’t have sick days. But it was fine, because I didn’t take a lot of vacation and didn’t get sick very often. And that you can make a lot of money.
But I got it so in my head that one hour equals money, that once I didn’t have that, I remember telling Sherry, we’re taking a week vacation, so I need to figure out how to work 40 hours out of the week before. In addition to the normal week, I need to work an additional 40 hours out of the week before or the week after.
She was like, why? I was like, well, because that’s what you do, because you work 40 hours every week. She’s like, no, not anymore. I couldn’t do it. It took me several months to do what you did, which was to kind of unwind it. It probably took me a couple of years to not still feel guilty when I did it, when I would wake up, get the kids to whatever daycare preschool.
I would go to Starbucks or I would go to Barnes and Noble. I would look through books, I’d drink some coffee at the cafe, and I would just not work even though (of course) I’m looking at business books and I’m thinking about marketing. I pretty much am working all the time, but I wasn’t actually sitting there pounding the keyboard. I would have this amazing sense of guilt that I was letting the family down or that I wasn’t growing the business as quickly as I should be.
It’s not a good thing. I talked about relentless execution, which we might have time to touch on a little later on. I think that’s such a strength, but that’s the dark side of it. That’s the other side of that coin, is the need to relentlessly execute, the inability to unwind, chill the […] out, and enjoy your life, instead of constantly feeling this guilt and pressure to sit in front of your computer.
Dave: That is super unhealthy. I find myself still doing that today. Here we are 13 months in, and there are days that it’s been a terrible afternoon, I’m […] productivity, and I still feel somewhat compelled to keep going. But now, I will actually realize that I’m at that point where the productivity is not where it should be. I’m like, all right, I’m done. I’m just going to go do something else.
If I still feel like I have to do something, I will try to do family productive stuff. Maybe it’ll be like catch up on the finances to do the bills, or go do some chores around the house, or something so I don’t feel like I’ve wasted the time, but at the same time, I’m not sitting here wasting time in front of the keyboard not doing anything that should move the business forward.
Now I realized that there are windows of productivity. Those are what I need to protect, enjoy, and take advantage of. When it goes—and it always goes, it never stays, your flow state is not infinite—then it’s okay. Let it go. Plan for that somehow. That’s the hard part. I’m still struggling with that today.
Rob: I think a big surprise for me, separate from that one that we just talked about, was that I felt an immense sense of relief and happiness to be finally be working truly for myself, not having clients, not having a boss. That stayed with me.
But what started creeping in was the arrival fallacy. It’s that I became gradually unhappy over the next 6–12 months, because (I think) as humans, that’s what we do. We figure out how to be unhappy with whatever mountain we climb. It’s like, oh, there’s another one over there and it’s higher.
For me, it was a boredom. I have all these autopilot. Basically, I didn’t have the four-hour–workweek. I had about the 10-, 12-hour–workweek, and I was making a full time living—$100,000–$150,000 at the time—but I got super bored. Is this it for me? I’m going to do this for 20 years? I’m more ambitious and this is what I started realizing.
I was surprised, and I stopped being surprised. This happened to me several times when I left full time employment to become a consultant, freelancer. When I started working from home, each of these things were things I’ve always wanted to do. I did them and I was happy with them for a few months until I wasn’t. This was another step.
This was one of the later ones where I was still surprised by it. Because then the next step after that, I’m like, oh, I want a recurring revenue SaaS app that does $30,000 a month, then I’ll be happy. I remember being that, which is what HitTail became. I remember being like, dude, you’re going to be happy for about six months.
At least I learned from it as I got older. But at that time, it was still surprising to me that it didn’t just solve all my problems, make my worries go away, and make me happy for the rest of my life.
Dave: Those things that you just talked about there, I’m constantly haunted by Dan Pink’s Drive—autonomy, mastery, and purpose. I’ve never gotten to a point where I’m like, okay, I’m happy, and none of those three things are present. The problem is that when you get happy with those three things, you will eventually also get bored because you’re no longer doing those three things.
Your purpose will change, wanes over time, or you’ve achieved mastery. Now, what? You may have autonomy already, great. But when you aren’t changing that mastery and finding something new to learn, or your purpose just isn’t there anymore, you’ve automated the crap out of it, what’s your purpose? Those things make me bored, too.
I worry about that a lot. In fact, with all the frothiness that’s going on in the M&A market and PE firms just getting stupid with throwing money around left and right, buying companies up willy-nilly, I’ve entertained, could I sell Recapture? Oh, yes. I could do that, but what would I do then?
I know that that’s an important question. If I don’t answer that question before I do the other question, then I’m going to be in huge, huge trouble. Because the times that I have sold things, it’s been when I had something else to jump to like, oh, I’m selling the plugins, but I’ve got Recapture to focus on. Oh, I’ve sold these other tiny businesses well, but I’ve got the plugins to focus on or something like that.
I don’t have something else. That lack of purpose says, then I’m not done with this yet. Until I find another purpose, then I can say, all right, maybe I’m done with this. It’s the same set of motivations.
I recognize that in everybody. When they don’t have that purpose and they get bored, they’re not happy. It doesn’t matter what level of success you achieve. You could have tens of millions of dollars and lack purpose, and you’re going to be miserable.
Rob: That’s why retirement is hard for a lot of people. I think our generation and younger is probably, now that we have the internet, we have podcasts, YouTube channels, and social media, the ability to kind of make a living in these ways, I don’t know if I will ever retire. I don’t know that I will.
My dad stopped working one day because he had to go into an office and manage construction projects. You don’t want to do that when you’re 75. I don’t know that I’ll be still doing a podcast and YouTube channel when I’m 75, but will I still be thinking, and writing books, and advising startups? I think so. I don’t know why I would stop doing that as long as I was able to, physically and mentally. It’s different these days.
One thing I want to call out, you said, what would I do if I sold? You hear that from Basecamp. David and Jason Fried would say, what would I do if I sold? For them, I struggle with it a bit more. I find bootstrappers repeating that, and mimicking it, and saying like, what would I do if they sold?
I think if you can sell for $10, $20, $30 million, or enough money to where you never have to work again is probably how I should phrase it, I actually think that you’ll find something to do, because you have infinite time and there’s no pressure. If you, Dave, could sell Recapture—I know that it’s not at that point yet—for $20 million and you know that you’re set for life, then I would say, the what I do next is whatever the hell you want and you’ll figure it out.
You can be a philanthropist. Maybe you write a book. Maybe you start another startup, maybe you buy a startup. Maybe you explore hobbies, because you literally have no time clock. You can not work on anything that you don’t want to for the rest of your life. That is different than I’m going to sell my bootstrap startup for a million dollars, which in the US is just—
Dave: That’s not life-changing money anymore.
Rob: No, it isn’t.
Dave: It can change your life, but it’s not an infinite change. Like $20–$30 million, you’re safe.
Rob: Right. That’s where I would say, listener, if you could sell for a million or two and you don’t know what to do next, fine. Keep growing that business, it’s great. Get it to that point if that’s your desire to where you can sell for $20 or $30 million.
But I do struggle sometimes with entrepreneurs who have changed their life, who have built an incredible business, and they’re just like, what would I do next? But also, they don’t like their job. If you love your company and you’re working on it, then fine. Keep doing it. I have nothing against that. It’s this fear mindset of I’m not creative enough to be able to replace what I do with this day job that I’m tethered to.
I want to mix it up a little bit, Dave, and go on to the second topic we’re going to talk about, which is balancing a side project with a day job. I get this question fairly frequently. Someone asked me in an in-person event a few weeks ago. It sparked again in my mind. Really, how do you work a day job? I’ll include full time, I’ll include contracting, freelancing, whatever you want to call it. How do you balance that with a “side project” that you want to become?
Your goal is for it to become your full-time income. You and I both have stories of how we’ve done this. I want to just toss it to you first and then I’ll weigh in. What was your process as you were doing?
You had three products at the time, and you were traveling. You had a client that you were traveling to. You hop on an airplane one week, a month, or something? And a family, right? Wife and kids?
Dave: Yeah. I could tell you how to do it badly in some cases here. It’s a juggling act. I’ll tell you right now, you can easily deceive yourself into thinking, I can totally do this and master all parts of that. The reality of it is, you will not.
If you’re trying to do three different things, let’s say you’re trying to do the family, you’re trying to do the side hustle, and you’re trying to do the contracting job, the full-time job, or something like that, I guarantee you, at least one of those will suffer and suffer badly. For most of us, especially men, it’s not going to be the full-time job, because that’s the one you’re going to make sure that one still brings in the paycheck. That means either the family or the side project are going to suffer.
I’ve seen people that have done both of those. I have done both of those as well. Neglecting your family and neglecting your relationship with your partner, your SO, that is not sustainable. That will resolve itself in one of two ways. Either you’re going to say, no, we’re not doing this anymore, or something more serious is going to happen, like into a divorce or other kinds of conflict there. That one is going to be really rough.
What ends up happening? Your side project ultimately ends up suffering. If you are lucky enough to get enough revenue, which I was for the plugins, then you can start to hire people to deal with some of those things and take some of that stuff off your plate. What that ultimately means is that you’re still not spending a ton of time on those, and your focus is on the other two, so at best, you can keep it to maybe sustenance mode.
You’re never going to be into hyper growth, hyper building, hyper expansion, hyper improvement mode. There’s a limit to your time. There are strategies you can do. You could say, all right, for this period of time, if you’re a contractor, you can say, I’m not going to contract and work on the side project. That way, you got two areas of focus.
That’s great. That’s one way to manage it. But then you have to make sure you’ve got a buffer built up, and that your family is on board with that, and you can handle your finances, et cetera. Then there’s another one of saying, all right, well, the full-time job is just not that demanding. I know several people that have had very undemanding full-time jobs.
They get their work done in 15 hours in a 40-hour week. They got these 25 hours just sitting around. They can do their side project during that time. I had that for a while. That was part of what helped me build that up. But ultimately, that is not going to last forever, not going to be sustainable.
Something will change at some point. That won’t work, but your focus is key to growing any business. Since I have tossed aside full time consulting, I have been able to focus on so many more things and drive Recapture forward and try a bunch of stuff, even stuff that didn’t work more quickly, more easily now that it’s my full-time thing.
I can do it more sustainably, because ultimately, if you’re trying to put your focus on all three of those things, you will hit burnout. It is not a question of if, it is always a question of when. There’s my tidbits of advice on that having tried that for close to a decade.
Rob: Man, you paint a dark picture. We can hear it, it’s something upbeat.
Dave: Don’t do it, man.
Rob: No, but it’s true. It’s true. I get questions on this podcast of people writing in and being like, I just can’t swing it, I’m too tired. It’s like, then you shouldn’t do it. Or you should take an alternate path to where maybe you work your number two at a startup, or you work for a startup, or save up enough money.
I’ve had some friends. I couldn’t do this with our expenses, having the family and Sherry was in grad school, but I had a friend who saved 18 months of living expenses in the bank in cash, and then quit the job and built something. That also scares me, of course, because SaaS can take a long time to find product-market fit.
Dave: Eighteen is not enough these days. No. Yeah, that’s tough.
Rob: I know, it doesn’t feel that way. But all that said, it is tough. I think people need to hear that. I think that there are alternatives. Some folks, they sell fund through (as you said) consulting on the side or consulting during the day, working at night. That’s what I did.
I always had either a day job or some type of 9–5 consulting five days a week, and then it was all nights and weekends. Part of it, we didn’t have kids, and then when we had kids, it was like, well, then we put the kids to bed and then I would work. I don’t do well on little sleep, but I just forced myself too for a while, where the kid would go to bed at 7:00, and then I’d go 7:00 to midnight, and then get up and do that. I got five hours a day.
It was tough on the marriage. But to your point, you’re not going to be great at all for any of these things all at once. There’s family and there’s your side project. You’re going to neglect one of them.
I remember really grinding on it for a while. I remember there was a moment where my contract said, you know what, we have you 40 hours. We’re running into some financial issues. Could we drop you to 20 hours? I was like, yes, this is the best idea ever.
In retrospect, I wished I had thought to propose to them, like, could I go to 32? Because I had done that with a day job where I’d actually dropped down to 80% time at a full-time job before I left a few months later to freelance and consult.
That was really nice, because then it truly was less of a grind. It wasn’t 60 hours weeks anymore. It dropped it down to about 50. It was like 20 consulting, 30 doing the other thing, and a lot of it was during the day.
I just remember the huge weight off my shoulders. Like I said earlier when I did finally quit that, I felt like I had so much time, infinite time. Let me get this straight. All that crap I’ve been doing from 7:00 PM to midnight most nights, I get to do during the day now, and then I have my evenings. That was actually a reset.
Another surprising one is I was like, okay, now I need to figure out how to do stuff in the evenings and not think about work, to back to our original point of letting it turn off. It’s like, I guess we do have friends. Maybe we should hang out with them sometimes.
Dave: Right. Ultimately, how many times have you said this on the pod over the years? It’s a marathon, not a sprint. If you try to sprint, you can try to sprint for short distances, but it’s not sustainable. You must rest after each sprint, literally and figuratively both. You have to have that time to rest, recoup, and find that sustainable strategy.
If you have the burn rate, you can work part time in consulting and do your side thing, great, do that. That is more sustainable. If you are single and don’t have the demands of the family that you would, if you had kids and an SO, great. That’s an excellent time that you can build a startup. But still, you have to take care of yourself.
You will burn out if you just try to burn the candle at both ends, 40 at the job, 20 at the side hustle, and just do that seven days a week. You think, oh, the weekends, hey man, I can totally do this 16 hours on the weekends. No, you can’t. Not indefinitely. Sure, you can for a while. It won’t feel great. When you hit the wall, you’re going to hit it hard.
Like you said, I don’t want to paint an unrealistic picture of this, because you and I have both tried various strategies on this with varying degrees of success. On the other end, we both realized, focus wins and you have to find a way to get that, protect that, and your health. Those two things. If you don’t have those, you’re not going to have a business that works.
Rob: This is one of the reasons that I started acquiring products early on. 2006 was my first and I realized, oh, this is a way that I don’t have to do nearly as much of that upfront grind with no return of just months, and months, and months of coding at night to finally launch and then realize, oh my God, now I’m at the starting line.
Now I got to figure out product-market fit and all that other stuff, whereas I could buy a product. My original one, it wasn’t SaaS. It was 2006, so that wasn’t really a thing. I was freelancing on the side, working a day job, and I put all the freelancing money into an account. I had $12,000–$15,000, and I spent most of that on DotNetInvoice. I dropped an $11,000 check.
It was very scary. I actually kind of got screwed in a way. I didn’t know what I was doing. It was freaking wild. It was 16 years ago. It might even have been 17, whatever. The revenue wasn’t what they said it was, but that let me skip twelve months of building that thing. It probably would have taken me twelve months of nights and weekends to do it. It already had a marketing set up. It had a little bit of SEO. They were doing a little bit of Adwords. It had just a skeleton of things. I think that’s another path.
Most entrepreneurs don’t want to do that because they want to build their own thing. A lot of them are developers and they want it to be their code. I get it. But one way to avoid some of the pain that we’re talking about is to acquire things, and that’s what you had done. Think all of your stuff, Recapture and the WordPress plugins. You’d acquired stuff before that as well.
Dave: All my successful stuff was acquired. The things that I tried to build from scratch like Support Line, yeah. I’m not saying you can’t do that. I screwed up on so many levels with that one not figuring out what the customers wanted, not trying to get people on board in advance. I made so many of those.
In the last episode, ten classic SaaS mistakes. Your number one was, make sure people want the product. I didn’t make sure that they wanted the product. I just started building it based on some faulty assumptions, and it blew up in my face $50,000 later.
Dumb things like that will kill you every time. You get a level up advantage if you can find something that has product-market fit that you think you can grow, that you can see the flaws in, and acquire it for a reasonable price that already has some revenue, some traction, and build on that. That’s still to me, a massive advantage today.
Rob: Indeed it is, sir. If folks want to keep up with you, you are @daverodenbaugh on Twitter and we will spell that out in the show notes of this episode. Of course, recapture.io if folks want to see what you’re up to. And you’re co-host of the Rogue Startups Podcast with Craig Hewitt. Thanks for joining me, Dave.
Dave: Thank you for having me Rob. Always a pleasure.
Rob: Thanks for joining me this week. If we’re not connected on Twitter, hit me up @robwalling and of course, @startupspod if you want to see our fun 90-second video clip that we kick out each week. Hope to connect with you there. Thanks so much for listening every week. Signing off from episode 612. Talk to you next week.