In this episode of Startups For The Rest Of Us, Rob is joined by Jordan Gal and Tracy Osborn for a roundtable discussion. Some of the topics in this episode including Basecamp reinventing email with Hey.com, Leadpages being acquired by Redbrick, the growing popularity of subscription based pricing and how many active subscriptions a person or business has nowadays.
Items mentioned in this episode:
- Bootstrapped Web Podcast
- Leadpages acquired by Redbrick
- How a 2 person startup already uses 28 other tools
- Tracy Osborn
Intro: Welcome to this week’s episode of Startups for the Rest of Us. I’m your host Rob Walling. Each week on this show we cover topics relating to building and growing startups using an ambitious yet a sane approach. We’re not willing to sacrifice our health or our relationships to grow our company.
I’m excited about this week. I’m diving into this idea of a startup roundtable or a news discussion show. I discussed a few topics with Derek Rhymer a couple weeks ago, but going a little deeper, this is the first essentially roundtable where I invite two guests on and we talk through topics that are relevant to us in the MicroConf, the Startups for the Rest of Us, the self-funded, the indie funded community. I hope you enjoy the show and without further ado let’s dive right in.
Rob: Here we are at Startups for the Rest of Us inaugural startup roundtable discussion. I have some pretty interesting stories to discuss today. Before that, I have two interesting guests I’d like to introduce. First on my right, as no one can see, but we’re in a camera is Jordan Gal, he’s hosted the Bootstrapped Web podcast, as well as founder and CEO of CartHook.
Jordan: Thanks for having me on, Rob. I’m excited for this interesting new format. Let’s see where it goes.
Rob: I’m excited too. Above Jordan in my view is Tracy Osborn, founder of WeddingMarketplace, WeddingLovely that she shut down about a year or two ago, now the TinySeed Program Manager. How are you doing today, Tracy?
Tracy: Doing well, happy to be back. Always excited to join the podcast when I can.
Rob: That’s the cool part is each of you have been on the show now several times: interviews, Q&A episodes, all that kind of stuff. Hopefully, folks are familiar enough with where you come from. That’s what I wanted to do with the show is get different perspectives from different people coming from different directions. I’m pretty stoked to talk through a few of these things.
As you listen to this episode, if you have thoughts on whether I should do it again in a couple of months—what was interesting is I went back to a month’s worth of startup news and tried to pick out stuff that I think is interesting to our little space, kind of the MicroConf Startups for the Rest of Us community. There just aren’t that many stories that are interesting to talk about, and I think we can get going on.
Every month or two, or even two or three months, is what I consider doing. If you like the show, if you don’t like the show, please contact us at firstname.lastname@example.org.
Our first story is about Basecamp watching Hey, it’s at hey.com. They’re essentially reinventing email, they are saying they’re not going to allow tracking pixels so people can track opens. I’m curious, Jordan, have you been following this? Is Basecamp basically potentially taking it too far by blocking tracking pixels? D and J said they’re going to shame people who send with tracking pixels.
Jordan: I have been following it. I think it’s very interesting. We saw Superhuman come out of the gate on fire. Everyone’s talking about how they’re going to be the biggest thing ever. I think that excitement has waned a little bit, they’re not that obsessed with it anymore. Then Basecamp taking on emails is super interesting, but like most things with Basecamp it’s very difficult to separate the people, and Basecamp, and the controversy they create from the actual product. They’re really close to the edge of making themselves too much of the story right now.
These guys are very clever. It’s starting to feel a touch manipulative on what they’re doing with Twitter to get attention. I love their ideological approach. I love that they are unique in their opinions. They take it strongly and they’re not afraid to say it. That’s all awesome, but I think they almost need to chill a little bit and then let the product speak for itself because there’s a lot of talk and it’s constant controversy. It’s a little bit grating.
The latest tweet that Jason put out, I forgot exactly what the context was, but he kind of felt that it went a little too far. I think he was making a comment on another company. People are starting to push back on it where they really have a huge halo effect to their products, but I think they’re right on the edge. Now it’s time to let the products start to speak for itself. I’m definitely interested, I want to see what they do. Because my email, that landing page and the copy that they wrote resonated. My email is an unhappy place. It didn’t used to be, but it’s been so long you forgot that it used to be this cool thing that you communicated with people on and it’s no longer that. They definitely nailed that part of it for me.
Rob: If you go to hey.com, you can read their manifesto where they say exactly that. I’m a big fan of their products, they’re genius product builders, they’re great content marketers. They wouldn’t call themselves that but they are exceptional, some of the best there are. They have this massive audience. It’s been fascinating to watch. What are your thoughts on this, Tracy?
Tracy: I find it funny that you mentioned the Twitter stuff. I feel like they’re using Twitter effectively. It’s how Twitter is meant to be used nowadays, which is annoying. It’s one of the reasons why I’m not on Twitter very often, but I feel like I can’t hate on them for doing this kind of launch because that’s marketing. That’s the way that they’re going to differentiate themselves from say Superhuman or these other ones that are very email marketer focused where Superhuman’s like, “Oh, you’re going to see the location. You’re going to see the tracking pixel. You’re going to track the people that open and close it. We’re giving you all those rates and data and whatnot.” They’re at the opposite end of the spectrum to Superhuman.
I’m personally very excited for it because I think that we do need to have more privacy-focused email clients. Gmail was the king for so long. The average user would use Gmail at a default. We’ve had, as email marketers, this superpower that we were able to see when people open their emails, we were able to see those open rates. I want to say it’s great for email marketers, but for the average person and privacy and whatnot, I want to give people more choice. I think that Basecamp is doing that.
It’s funny to think about email and the superpower and all this data that we had and how it’s hard to give up that data. If you look back to just paper marketing, pay per mail marketing, you didn’t know how many people opened up that envelope that you sent or how many people threw it right into the recycling. I agree that it’s going to hurt email marketers, but for the average user or at least the privacy focusing technologists who need those privacy features, I think it’s something that’s necessary. Basecamp is simply using Twitter the way it’s meant to be used.
Rob: I signed up when I first heard about hey.com. I am curious to use it. They have a list of 25 things that they are saying is wrong with email. I don’t understand how they could possibly fix all those things, but that would tend to be—it’s all these problems with email. You screen your calls, you can’t screen your emails. Some emails are worth your immediate attention, most are not. Files are attached to email rather than the other way around. You don’t need to be told to check your email. I don’t even know, that’s like 5 of the 25. I don’t even know how you go about fixing that. Like you said, Jordan, that’s when it’s time to think about getting into the product and watching it speak for itself.
My take on it, I built Drip. I like the idea and I’m going to be a user of the product, I assume, if it works and has unified inbox and has all the stuff I need, but I feel like railing against the open tracking is taking it a little too far. I like open rates, I think having aggregated open rates of an email is something that is just fine for a marketer to have. Knowing when and where and how many times people open an email could be taking it a little too far, I would admit.
Here’s the thing, they can come out and say, “We don’t use any tracking. We don’t use Google Analytics. We don’t track open rates.” If you have $100 million business throwing off tens of million a year in net profit with 50 employees you can do that too, but if you’re a bootstrap startup and you’re trying to get to $10,000 or $50,000 or just trying to pay the bills, like you’re in such a different position that I would caution against taking that as advice or as something you should do as a business person because I think it can be dangerous.
You’ve heard the mentality of like, “Hey, you build a great product. That’s what we did.” and everyone uses it. I’m not saying Basecamp has said that but there are people who come out and say, “Look, I just built a great product and never marketed it and magic.” Everyone wants that to be the case and it almost never is, it’s the exception. That’s potential danger with coming out against that kind of stuff.
Jordan: We may be looking at it backwards because we are business people, and we build technology products, and we are looking at it from that point of view. In reality, it matters a lot less what is right for a business, and it matters a lot more to give the choice to the actual consumer, to the user. That’s really their perspective on it. I have an Amazon Alexa in my house, I have three of them. I have made the choice. I know what’s happening and I have made the decision that in the balance between privacy and convenience, that’s where I land on that product.
What they’re looking at in email is taking it back to the user’s control and saying, “If I don’t want tracking pixels, this is my inbox, not yours marketer. If I choose to degrade the experience of email with your company by blocking pixels, that’s my choice.” What Basecamp is kind of yelling about is it’s not okay that you don’t have the choice. It’s not okay that someone else decides what happens in your inbox because that’s not normally what happens other places in your life. In your home, you get to decide if you want an Alexa or not. People can make that choice once their right journalist do that work to uncover what was happening there. If looked at that perspective and it’s not a black and white tracking no tracking, it’s simply giving people the option, that’s tough to argue with.
Rob: That’s a good perspective. Tracy, do you feel like this blocking of tracking pixels will become a trend? Do you think it should become a trend?
Tracy: I think privacy, in general, is becoming a trend. I find it interesting you brought up Alexa because I feel like that was the start when people started realizing that this really great convenience in their homes could potentially be used for other reasons. I feel like those stories happened and then it evolved and some other internet communities are very privacy focused, almost to the extreme side of railing against all the things that are happening.
I personally had an Alexa and I ended up removing them from my house. That tells you a little bit about my own perspective. I want one, I want to have all these privacy tools but I personally have decided that the convenience is not worth it for me. I’m happy to see that it’s becoming a trend.
As the Internet has grown, I’m going to refer back to that word I used before, we have these superpowers. We start adding all these superpowers, all this technology, and all these things we could do. Now it’s like okay cool, we’ve reached this point where we need a lot of people to draw back a little bit and decide if it’s convenient for them.
Rob: Like a pendulum swinging different directions. That’s a good perspective.
Jordan: I was going to say you can see the email market has been around a long time and it’s mature. It’s gotten to the point that it’s so mature that this type of option makes sense. The in-home robot assistant isn’t very mature, but you can see how if someone came out with an Alexa-like device that you had more control over the privacy, that would be attractive.
It’s the same thing with the iPhone. People started freaking out where I just had a conversation in person about this topic and now I’m seeing ads on it, that’s creepy. The pendulum swung all the way toward maximum freedom and then we all realized, “Oh, I guess we’re the business model.” Now it’s coming back and that’s a healthy thing.
Rob: For the record, I have five Alexas in my house, maybe six. I think it’s hilarious that if you go to thisishey.com, it’s a business I presume has been around for a while. It’s an influencer marketplace, which is something I’m sure Basecamp would hate. What are the folks at This is Hey thinking right now? Where it’s like, “They just took our name and they have the dot-com.”
Let’s swing into our second story. Leadpages was acquired by Redbrick. By the way, all of these stories we will link up in the show notes. To clarify, because I actually had some people asking this, Leadpages was sold to Redbrick, which is like a software—it’s a holding company. I would almost phrase it as private equity, I don’t think they said that in the news story. You know with these private equity funds, they get together then they buy software companies and manage them. Leadpages was sold, Drip was not. In fact, to say that Leadpages acquired Drip is actually not technically accurate.
Leadpages and Drip are two products: Leadpages Landing Pages, and Drip is an ESP marketing automation. They were owned by a single holding company called The Avenue 81. Avenue 81, that’s the company that raised funding and stuff. It was synonymous with Leadpages but then it is what acquired Drip. Essentially, they’ve sold Leadpages. A quote from the CEO of Drip, John Tedesco, who I know personally, I actually worked for him before I left Drip a couple of years ago. He said, “The acquisition is allowing us to now ruthlessly focus on pursuing our markets. We have a clear capital base in which to execute. We’re flush with capital, so we’re going to use it with discretion. Use it intelligently.”
Obviously, the play here was to put dry powder in the coffers. If you have an asset, you can sell it in lieu of say raising a round of funding. It gives you not only the focus—I am conjecturing here, I will admit. I have not worked at Drip for two years and I have very, very little inside information at this point. If I were in Drip’s shoes, and I really see this marketing automation as a multi, many, many billion-dollar opportunity in the landing page market, it’s not; it’s a very small market.
That just kind of gives folks background. The first question I’d have for Tracy is MailChimp has launched free landing pages, in essence, with your email account. I know a few other providers that are making them very free or very cheap. Does it seem to you the landing page space is becoming commoditized?
Tracy: That’s an excellent question. The more options the better. I’m happy to hear that MailChimp is doing this. MailChimp has a really, really huge reach. Happy to hear that they’re making this stride because they also did—I can’t remember what happened with MailChimp but they had a controversy where they raised the prices or they took away their free tier. Do you recall what happened about a few months ago, six months ago?
Rob: I think it was if you unsubscribed, you were still charged for those subscribers because they’re moving a little more towards commerce.
Tracy: That came out and I think that kind of have hurt a lot of people’s usage of MailChimp. Now they have these free landing pages. You see that in ConvertKit as well. They have a whole landing page system and whatnot. It’s kind of a silly thing to say but I’m like, “I’m a fan.” Would love to hear what you guys say.
Rob: What do you think about this, Jordan?
Jordan: I think they’re commoditized. I think they’re lead gen. The business model is subscribers, so if landing pages help you get more subscribers, then the company whose pricing is based on the number of subscribers you have has a very vested interest in giving you the ability to add more subscribers. It makes sense with the business model, it’s also been commoditized. Just to clarify, the statement that you just quoted from the CEO, that’s the CEO of Avenue 81, the company that’s still-
Jordan: Okay, cool. Just want to make sure of that.
I love this corporate-level strategy stuff. It’s my favorite. A lot of people are going to look at it and say, “Oh, Leadpages failed,” or, “It wasn’t able to do what it wanted to.” I think this is brilliant. This is an asset that will only decrease in value moving forward. They’re able to effectively raise money for their email marketing product, which is Drip. They don’t need to sell equity in it because they had this other asset. It’s great.
They basically just raised, I don’t know how much they’ve sold it for but my assumption is they raised tens of millions of dollars in non-dilutive capital to go after a much bigger email marketing. It’ll be interesting to see what they do and which playbook they run. Are they going to run upmarket and hire salespeople and go after the Marketo version of things, or are they going to go with quantity and long tail and go after MailChimp?
I’m going to assume they’re going to go high-end with an enterprise sales team and run that playbook. They have the money to do it. They didn’t need to sell any equity in it. It’s great. Acquiring Drip was a very smart move, it worked out nicely for you. It looks like it might work out really nicely for them also. Especially if they thought this through over the past few years, then it was brilliantly executed. Let’s bring in a product, let’s make it the focus of the company, let’s sell-off this asset then we have our coffers ready. Now we can go after a much bigger market. That’s an optimistic view of it, but that’s an exciting version of things.
Tracy: The CEO that gave that quote, that’s the new CEO because the one that was around when Drip was acquired, that was a different person, right?
Rob: Yeah. Clay Collins was around when we were acquired. About a year after we were acquired, he stepped down and John Tedesco, who was the COO at the time, took over as CEO.
Jordan: I was going to ask if we’d look at John Tedesco’s history and what playbook he has been able to run successfully in the past, that’s going to tell us a lot about the future. Because it was an internal hire, it’s less clear.
Rob: He’s been part of multiple startups. I would say they are in line with the enterprise approach that you’re talking about, very much sales folks and that type of stuff.
Tracy: When I was looking at this announcement and the change in CEO, it seems like they had a certain strategy when they had Leadpages and they acquired Drip. From what I was reading into it, it sounded like things would work a little more together, but the strategy changed. The new CEO came on and they’re making this change because the strategy changed. It seems like it all makes sense in terms of the direction of Avenue 81.
Rob: I’m curious, Tracy, when you hear about a SaaS app like this being sold, so the original owner doesn’t have it, it’s now a holding company. Would you be more or less likely to use a product that’s been sold like that or does it matter to you? Do you even care?
Tracy: Interesting. Do you even hear about it too?
Rob: We’ve heard about this now. If you were looking for landing pages, there’s obviously a bunch of competitors to Leadpages. I’m curious if that would impact your decision to sign up as a customer or not?
Tracy: I’m thinking of the average user of how much they follow acquisition news. I’m assuming that Leadpages is going to continue to grow under the company that acquired it. If I was thinking as an average user I would suspect a) they wouldn’t know about it, b) if they did know about it, it sounds like instead of Leadpages being sold, it sounds like Leadpages was acquired. It could be spun in that way. Leadpages is acquired by someone who is going to spend more time and effort or more focus on it, both of those things are positive to me.
Rob: I want to wrap this up with just a funny little story that involves Best Buy and Geek Squad. I don’t know if you guys recall but Best Buy acquired Geek Squad, which is the tech support people who run around in the cars to fix stuff at your home. Geek Squad is now the vast majority of their revenue and profit. They are one of the big drivers that has kept them in business. When Circuit City and everybody else went under, they had this thing.
The CEO of Geek Squad, the founder who sold it, when he does stand up in front and does talks now, he’ll say things like, “When Geek Squad acquired Best Buy,” and everyone laughs. That’s the first thing I thought of with this is like did Leadpages acquire Drip five years or four years ago or did Drip acquire Leadpages? It kind of struck me as funny.
Jordan: Sounds like Avenue 81 is making the best of their situation.
Tracy: Leadpages wasn’t shut down. They spun it out and it still continues to live. It sounds like a win-win situation for everybody.
Rob: Yeah, for sure.
Our next story is about how a two-person start-up already uses 28 other tools. This is from acrossapp.com, it’s from their blog. They’re basically a tiny little two-person startup and they have 28 different subscriptions. I’m curious, ten years ago we may have had one or two subscriptions. You paid for Photoshop as a big package, everything was you buy it once and then you get the upgrades every couple of years. Now, most of us have 20, 30, 40 subscriptions. Tracy, do you feel like this whole movement towards the SaaS subscription economy is a good thing or do you feel like it’s cumbersome and we’re potentially paying more now but than we would have 10 years ago?
Tracy: I have to laugh because this is kind of a Tiny Seeds thesis, right? We’re betting on these business-to-business SaaS apps. We love to see people building things for other businesses to use. We’re part of this trend that’s happening right now. There are lots of little apps that are doing lots of little things for you that you can pay for individually.
Overall, I love it. I love it. I love anything that helps me save time. Ideally, that subscription cost is going to save me as much time and hopefully money that it makes it totally worth it. I love that there’s people out there that are building lots of little things to support themselves as they can create their startup and maybe get into Tiny Seed and all that. Huge fan of the system. I have no problem paying for subscriptions. I just want to make sure I don’t forget which ones I’m paying for because that’s the problem.
Rob: Something you pointed out there is that there are so many tools that could not exist in a non-subscription economy. These tiny little utilities you pay $10 a month for, I just think it’s changed the game. You can’t look at it as, “Oh, I have too many subscriptions or I don’t,” or “I wish there weren’t subscriptions that we just paid one time,” because it’s a completely different system now. All these apps that we use and that we build wouldn’t exist under a non-subscription economy. What are your thoughts, Jordan?
Jordan: I see an analogy to what happened with television. We don’t pay less for television now. Between all the different streaming services: Netflix, YouTube, Hulu, Amazon, everything; I’m paying about the same but the service is far better because I’m in control and I get to choose. I don’t think it’s any cheaper to pay for all these different pieces of software, but you do get a lot better service overall because you’re getting very specific needs for your business addressed.
I have the Google Doc open right now that we just went through a pruning exercise. Every two-three months I ask my assistant, “Okay, give me all the recurring subscriptions that we have in the business.” My CTO and I look at them. I have it in front of me, it is 61 rows long and maybe 10 or 15 of those are not traditional SaaS. It’s a good 40-50 services, if you’ll just excuse me for a minute if I read through a few of them. They’re all very specific and very necessary.
Adobe Creative Cloud, AWS, Atlassian, Atlassian Statuspage, BrowserStack, Calendly, Canva, ClickFunnels, Cloudflare, DigitalOcean, Docker, Drip, Dropbox, Figma. That’s alphabetic order. I could just keep going down to Z. It’s a Frankenstein but it’s a beautiful one. It does ebb and flow in frustration depending on where the market is and where your business is.
At some point last year we said, “Okay, that’s enough of these different systems, let’s go to HubSpot. Let’s go all-in-one.” But in other areas, that doesn’t make sense. For bootstrappers, for people building businesses, it’s a great thing to be able to address one specific need, but you may be caught in that ebb and flow of a larger all-in-one or you might need to go there. I love it as long as the individual services are good. The nice thing about the subscription version of things is if they’re not good, you just leave them.
Rob: That’s a big difference. It’s not like you drop $300 on a piece of software and then you get two months and you stop using it. You still paid the $300 versus the monthly. I’ve also found that the all-in-ones tend to be, it’s like you said, it combines, everything works together. I don’t know if it’s a little more expensive but the tools aren’t as good, the individual pieces aren’t as good. It is what it is. I’m obviously a big fan of this world. Having been around long enough to have several of my early software products were not subscription, they were one-time download. I remember the struggles of the first day of each month, I had zero dollars in revenue for that month. It wasn’t like I had that baseline that I had last time. That’s the big difference that you forget if you’ve never run a non-subscription business is you’re just grinding it out.
In fact, during the financial crisis of 2008/2009, I had one product. It was doing maybe $4000 a month but it was part of my income, it was a chunk of it. Sales dropped 80% overnight, one month to the next. That’s the kind of business that’s going to be—I mean imagine if we were doing $4 million a month and had a bunch of employees and it dropped 80%. That’s where you start laying people off. It’s just such a big difference that the subscription is from our perspective as the business I think they are a safety net. I’m like you two, I don’t mind paying for subscriptions because I like not having to install software and maintain it and do all that. That’s the benefit we get from it.
Jordan: I want to add something. If this is a bit of a news show about things that are relevant right now, I just saw last week a company launched named pipe.com. I jumped on a call with the founder. The reason for bringing it up is because the downside of the subscription economy, and being a developer, and running a company based on subscriptions is that that lifetime value is stretched out. We’re all familiar with Gail Goodman’s Slow SaaS Ramp of Death and the math behind paying to acquire and then collecting over a longer period of time.
This company pipe.com that just launched, what they do is they take MRR, they take your monthly payments, and they will pay you annually. If I have a customer that pays us $500 a month, Pipe will look at that and say, “Okay, we understand your churn rate. We think this is a good bet. You can choose to sell us this customer, we will give you the whole annual amount of money upfront, then you just continue collecting monthly from them.”
The subscription economy is great in a lot of these ways but one of the tricky parts is cash flow, especially for younger companies that aren’t in the only annual, you must pay as an annual contract or you could do business with us. That strength comes later. It is tricky on cash flow but there are additional financing options like pipe.com that are starting to address that. We’ve seen revenue-based finance, we’ve seen other things. Pipe.com is not debt. It’s kind of like factoring but for SaaS. They charge you 15%, which is basically what you would charge people anyway because you would give them two months free. That’s kind of the default.
Rob: If the customer cancels in six months, they eat it, so they have a risk model.
Jordan: No. You pay back the remaining portion.
Rob: Got it. Okay.
Jordan: There’s literally an online portal and you can choose an individual customer. “I know that customer. They’ve been around for two years. They’re not going anywhere. I’ll sell that to you because I’m very confident that they’ll stick around.”
Jordan: It’s fascinating. Or you can sign an annual contract, which is something that we do. Our annual contracts are paid monthly. We have annual contracts but we don’t have this big, large chunk so they sign it. That is even less risk. This is an annual contract, they’re paying monthly, and I’ll just choose. I’ll click that and hit sell. I’ll get the money for that entire thing upfront, minus the 15%.
Rob: I love the innovation, all the innovation that’s happening in the financial models around SaaS. You’re right, that is the biggest Achilles heel is the long slow ramp of death.
Jordan: It’s awesome. It’s just the relationship with you and your billing software.
Tracy: When you say sell the customer, is that they’re acquiring the customers’ information for use?
Jordan: They’re still in your Stripe account, you’re collecting money, and you’re charging their card every month like normal. But then they will see, “Oh, that customer paid in Stripe. Cool. We’ll take that much amount from your bank account.”
Rob: Pretty interesting if you need money in the short term. I know folks looking at raising around or doing debt kind of financing their SaaS revenue.
Jordan: I’m looking at the same thing. I looked at them and I’m like, “Oh, that’s basically just taking your MRR and creating a line of revenue off of the MRR, and then not actually putting any debt on the balance sheet and also not selling like equity.” I was like, “What is the catch here because that’s very attractive.”
Rob: I think the catch is like when you think about—
Rob: There is some risk but I also think you’re basically spending future earnings. It’s almost like when you put money on a credit card now that’s technically debt and this is not. When you put money on a credit card, you basically are spending future earnings before you have them. That’s what this is in essence. There is some danger. If you’re prudent at managing cash and you know where that cash is going to go or you’re in a spot where you do think you need some dry powder in the coffers, I think it’s certainly an interesting avenue to look at.
Wrapping us up for today, I’m curious from each of you what is your favorite podcast right now? I mean right now because sometimes I have a favorite podcast for two months and I binge them all and then I move on. Tracy, you want to go first?
Tracy: Gosh. Don’t go pick me first. I’m the worst at podcasts because I have a hard time with podcasts. I know some people are able to play something at 2x speed and then go through all their backlog. Then for me, it’s like, “Oh my gosh, I only have a certain amount of time. I can only do 1X.”
That said and it’s a dorky one, I’m still a big fan of Adventure Zone. It’s by My Brother, My Brother and Me. It’s their D&D podcast. Also, My Brother, My Brother and Me is another one I listen to. It’s just because I need to turn my brain off from work. I listen to a lot of work when I podcast, Startups for the Rest of Us, Out of Beta, a lot of other ones. It’s really nice to have something that’s just a bunch of people just in a room together having fun. I would say that my answer is the Adventure Zone and by extension My Brother, My Brother and Me.
Rob: How about you, Jordan?
Jordan: I’m just going to reject your premise entirely and mention several of my favorite podcasts.
Rob: I’m not picking five favorites, that’s cool.
Jordan: I need to be generic. I absolutely love the Joe Rogan podcast. It’s interesting, it is just really interesting. It challenges a lot of your thoughts, and assumptions, and is entertaining, it’s funny. There’s so much of it. You don’t have to listen to everyone and you’re fully entertained.
I also love the Dave Chang Show. Chef Dave Chang from Momofuku has a great podcast that is about food but also about creativity. He brings people on from his network in the Bill Simmons world. That’s a very interesting one. I like Brian Koppelman, The Moment. I absolutely love The Story Pirates. That podcast is so good, it’s for kids.
Rob: My kid knows about that.
Jordan: Oh my God. Look, I drive my four-year-old to school every day and it’s about a 20-minute ride. That’s what she wants to listen to and we just laugh our butt off about it. It is these extremely talented actors that take stories that were written by kids and dramatize them and turn them into a story and song and so on. It’s so brilliant and so entertaining. The kids all love it. You don’t mind listening to it. I don’t know how many more times I listen to the Descendants 3 soundtrack before I bang my head up against the wall. Story Pirates, big thumbs up.
Rob: Me as well. They’ve written books that my kids have. We actually saw them live. They came to Minneapolis and performed at the Parkway Theater. We went and saw them in there. They do a bunch of improv. They’re really talented improv actors.
Jordan: You saw Lee, Nimene, and Rachel?
Rob: Oh my gosh, we totally did.
For me, I listen to 40 podcasts so I’m not going to read through them. The one that I’m really digging right now is Reply All from Gimlet Media. You know you have a good podcast when every time I look at the title, typically I’m like, “That sounds totally not interesting. I don’t care about that.” I’ll read the description and by the time I’m three minutes in I’m like, “I care so much about this.” I’m sitting in my driveway waiting for it to finish before I walk in the house type thing. That’s been a big one. I’ve actually been listening—there’s an old D&D podcast that’s been around for 10 years. It’s not actual play. I can’t listen to people playing D&D. I can play it and I like it, but I cannot listen. I can’t do Adventure Zone. I tried and I just, I can’t get into.
There’s one where they talk about the lore and the history and they talk about the books and they talk about rules and how to be a better DM. Just all the stuff around at the meadow, which of course I’m always interested in the meadow. You can’t just start a company, you have to talk about starting companies. I can’t just play guitar I have to learn how they’re made. I can’t play D&D, I have to learn how to create it. Save or Die and Save for Half are the two that I’m really into. One has been around 10 years.
That’s going to wrap us up for today. If folks want to catch up with you, Jordan, you are @JordanGal on Twitter. Hey, do I pronounce your last name right? Is it Gal?
Jordan: It is Gal. Yes.
Rob: I used to call you Jordan Gal, but that’s not. That’s how it’s spelled, right?
Jordan: That’s right.
Rob: I heard you pronounce it differently. @JordanGal on Twitter and Tracy is @tracymakes on Twitter. Her website is tracyosborn.com.
Tracy: If I could get @tracyosborn on Twitter I would, but I did not. Some people might know my old Twitter username and that was a terrible idea and @tracymakes is better than what I had before. That’s what I have.
Rob: It’s all there. If you’re interested in podcasts, check out Jordan on Bootstrapped Web. Thanks so much for joining us today.
Jordan: Thank you, Rob.
Rob: I have to be honest, it was a fun show to prep for and record. I hope you enjoyed it. Certainly feel free to reach out. You can reach out privately: email@example.com. If you have constructive feedback, if you want to give some accolades, a thumbs up, hit me up on Twitter, @robwalling. I look forward to hearing from you.
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