Episode 659 | Indie Hackers’ Newfound Independence + The SaaS Playbook with Courtland and Channing

Rob Walling:
Welcome back to Startups For the Rest of Us. I’m Rob Walling. Today I sit down with Courtland and Channing Allen, the co-founders of Indie Hackers, to talk about their newfound independence. They are no longer owned by Stripe. They also turned the tables on me in this interview, and we spend probably the first 30 minutes talking about my new book as well as sharing theories about entrepreneurship and just all the tasty goodness that comes when I sit down with really smart people who are thinking about entrepreneurship on a day-to-day basis. This episode will go live in both of our podcast feeds. If you haven’t checked out the Indie Hackers podcast, you definitely should. It’s a great companion podcast to Startups For the Rest of Us. But if this episode feels like kind of a cross between an episode of Startups for the Rest of Us and an episode of Indie Hackers, that’s because it is. Because essentially we have all the hosts and we were interviewing one another on the important topics of the day.
So we let this intentionally run long. There was just a lot to talk about. To be honest, we hit stop on the recording and talked for another 20 minutes about things that we probably should have recorded. We started talking about AI and about angel investing and a few other things, but that just goes to show you the content was flowing and it was one of those magical moments that you do want to capture. So I know I keep episodes between 30 and 40 minutes typically, and this one’s a little longer, but I hope you enjoy it and agree that it was worth doing. Before we dive into the episode, MicroConf Mastermind Matching opens on April 3rd. That’s just the day after this episode goes live. And realize you can head over now to microconf.com/masterminds and get on the wait list to be notified.
Every time we do Mastermind Matching, we have people contact us after the deadline closes begging to be included and unfortunately we can’t. There’s a reason there’s a deadline. Because we start matches. So we only do matching two or three times a year. We have matched more than a thousand founders across dozens of countries, dozens of time zones with a combined ARR somewhere approaching $200 million across all the companies. It’s been a very successful offering from MicroConf. One of the most successful offerings we’ve had in years. We’ve only been doing it three years, but it has just taken off and I’d really encourage you to check it out. Whether you are in the idea phase. Or whether you’re doing 10 million ARR, we have a match for you. And we match you up in these small groups of like-minded founders. If you apply between May 3rd and May 12th, which is the deadline, we’ll have your match sent by May 17th.
In addition, if you’re interested in chatting with me at an upcoming MicroConf local or you have a strategy or a framework that you think other bootstrap SaaS founders should hear, we are always looking for founders to come out and share their expertise during all of our conferences and events. If you’re interested, head to microconf.com/pitches and share your idea with us.
And with that, let’s dive into my conversation with Courtland and Channing.
Courtland:
Anyway Rob, welcome to the show. We sort of already introduced you in our preamble, and I’m sure anyone who’s listened to the show for a while also knows who you are. How you been, man? It’s been a while.
Rob Walling:
I’ve been good. I’ve been working on MicroConfs. I’m leaving tomorrow for MicroConf Denver in the US here. And then I got my book going. That’s my big project I’m heading up right now.
Courtland:
Nice.
Rob Walling:
Yeah.
Channing:
Wait, how many MicroConfs are there? There’s Denver, there’s Vegas.
Rob Walling:
Yeah, well so-
Courtland:
No, there’s not Vegas anymore.
Rob Walling:
There’s a US.
Courtland:
Oh, okay.
Rob Walling:
Yeah, there’s a US MicroConf and it used to be in Vegas, and then we moved it. It was in Minneapolis last year, it’s in Denver this year. I don’t know that we’ve announced the city for next year. And then there’s a Europe, and those are our flagship events. And then we do the locals, which are these just one day almost afternoon events where we get a big name guest and hang out for a few hours.
Courtland:
Channing and I were just talking about getting back in the game when you’ve felt kind of out of the game. And I know that we’ve been out of the game because we haven’t been doing MicroConf in a couple years.
Channing:
Yeah.
Courtland:
Part of that is because of the pandemic, but part of that is just out of the game. So next year Channing, we should bend our company budget to come.
Rob Walling:
Yeah, I was going to ask if you guys were going to make it to MicroConf next week.
Courtland:
Not next week, but next year. As soon as we know the city we’ll be there. Because it’s been a while and MicroConf has so much energy.
Channing:
And also we’re underwater actually becoming a real business again. So I feel like next year we’ll actually have the systems and the processes in place where we’re running it as opposed to-
Courtland:
It is nice to put everything on Stripe’s tab. That’s something we’ll miss.
Rob Walling:
Yeah. To not burn 10 grand a month of your own money.
Courtland:
Yeah, yeah.
Rob Walling:
It’s like uh-oh.
Courtland:
When it’s your business, it’s like, “Yeah, I could pay this. This could be my salary.” So you got to be way more judicious with business expenses.
Rob Walling:
Totally.
Courtland:
But MicroConf, of all expenses, I think is worth it.
Rob Walling:
Yeah, it’d be great to have you guys back. It’s been a while.
Courtland:
Yeah. It’s been so long. You are writing a book or have written a book. How far are you in your new book? It’s called the SaaS Playbook.
Rob Walling:
It’s all done.
Courtland:
Well done.
Rob Walling:
I finished that months ago. Four or five months. Yeah. I have a hard copy. Got some digital print copies. Yeah, it’s a hardback, which is like-
Courtland:
Wow. Look at that. That’s a beautiful book.
Rob Walling:
Thank you, man. I paid a lot for this. My first book, Start Small Stay Small, has a black cover. I don’t know if you’ve seen it. It’s ugly as hell.
Courtland:
Yeah. Yeah. I have it.
Rob Walling:
Because I had no budget, no money. Because I knew myself. This one, I was like, all right, I’m going to go all out and hire a legit designer, legit layout person, actually get an editor this time and not edit my own work.
Channing:
So you put that together your yourself. I was curious about the publishing process. This sounds like independently published and you kind of put together a team of the editor and the designer and all that stuff.
Rob Walling:
Yeah, exactly. So this time I hired a … I didn’t remember how much work it was, but I knew it was going to be a lot. So I went and found a book project manager who used to work for a publishing company.
Courtland:
Book project manager.
Rob Walling:
Isn’t that crazy? It’s very niche, but I was like I want … I went out just seeking if I can find any type of project manager, I’m sure they can do this, and if they have publishing experience, great. And turns out she had worked for a publisher for three years, so she knew everything. She’s like, “Oh, you can buy 10 ISBNs for the price of two so you should …” Just all the little internals. “Oh, and I already know four different printers in Hong Kong and in the US, and I’m going to tell you.” It was that type of stuff. So it really took a lot of load off of me.
Courtland:
How much money does it cost to basically do a book right? Self-publishing. You’re hiring a book project manager, you’re hiring an editor, you’re hiring someone to design the cover, to make a video for you on Kickstarter. How much all in does it cost to produce a book in 2023?
Rob Walling:
At this point, I bet I’m in 30 grand. 20 to 30 grand for all the labor. That’s before printing costs or any fulfillment.
Courtland:
Wow.
Rob Walling:
Yeah, it’s a trip.
Channing:
And so that’s all mostly upfront to get the thing produced by the different people.
Rob Walling:
That’s right. And that doesn’t include, obviously, I spent a bunch of time writing it and I had a writing coach who was busting my chops. I haven’t included her in that price because this is the first book where I’ve used a writing coach.
Channing:
What is a writing coach? I want to write a book, not nonfiction, but I’m curious about all these details.
Courtland:
Yeah. What does a writing coach say to you? Does she just say write more?
Rob Walling:
Yeah. They can have a bunch of different roles. If you want to write every word yourself, then you get the writing coach … He or she will be almost a developmental editor where … Well, it’s two things. Accountability and developmental editing is really what it is.
Channing:
Which is big.
Rob Walling:
Yep. So it’s weekly call. I know that I have to show up with X thousand words written, and if you don’t, then she was like, “So I guess we’re going to ship late.” And I’m like, “Oh no, I feel so guilty.” Taking advantage of my guilt complex. So accountability was a big thing for me. The second thing was she would just read through and be like … Not even copy editing, but like, “Yeah, it’s not hanging together.” So she’d reorganize pieces. And then the third thing for me that I needed was I didn’t have time. It’s 45,000 words in this book.
I didn’t have time to write every word, but literally, I had someone go through and scrape it for an AI project. Like close to a million words spoken on my YouTube channel, on my individual podcast episode. Just incredible. So I would pick topics and be like, I recorded a whole solo episode around just this topic, and I want that to be a section. So she would take that, transcribe it and turn it into a section. So she would write the words, but they were my … So you could say she’s a ghostwriter, but I always struggle with that because it’s all my thoughts.
Courtland:
It’s your ideas.
Rob Walling:
Yes. And then I would come back and put my voice on it. So she would do a first pass-
Channing:
That reminds me. Sorry, go on, go on.
Rob Walling:
No, that was it. So it cut a huge amount. In fact, I stalled. I got about halfway through the book and then I had about a year where I didn’t write a word, and that was when I realized I need someone else involved in this because I just can’t push it through with the other stuff I’m doing.
Courtland:
So there we go, content reuse in action. It actually works for books. And I’ve seen this before too because I interviewed for my other podcast, James Clear, who wrote Atomic Habits, which was literally the number one bestseller on Amazon for weeks. And Mark Manson who wrote The Subtle Art of Not Giving a … And they both did the same thing where instead of repurposing their podcast, they repurposed their blog posts and then just edited it and put it together in a book. And that actually works. And it doesn’t make the book any worse. It makes the book better because you’re picking the best ideas that you’ve already put out into the world, already tested on an audience. Now you’re just putting them in print format where they’ll just live forever.
Rob Walling:
That’s right. And I did that. So my second book … I’ve written four books. Start Small Stay Small. My second book is exactly that. It’s a collection of blog posts and it’s called Start Marketing The Day You Start Coding. I give that one away for free on my site. Third one I co-wrote with Sherry, Entrepreneurs Guide To Keeping Your Together, and then this one. But the second one is exactly that. It’s my favorite blog post. Because I had almost 200 blog posts at one point, essays and such. And compiling that into a best of was … I still get positive feedback about it.
Channing:
I just had a conversation actually with Josh Kaufman who wrote The Personal MBA. He’s sort of a regular at these MicroConf events. And he specifically mentioned that he’s struggling. He’s working on a new book, it’s going to be a followup to Personal MBA. And he’s like, “Well, I’ve got a lot of other stuff, a lot of other balls in the air as well.” He’s working on a website where he’s going to have courses and he wants to keep in touch with his email list. And he’s like, “Yeah, it’s kind of hard to figure out a way to work on any of these individual projects.” And that idea of, well, why don’t you figure out the topics? Because he’s still brainstorming for his book. Why don’t you figure out the topics that are going to go into your book by testing things out, going out to your email list and getting information. So it’s not just a way to save time once you decide you want to put the book together, but it’s also a useful way to figure out what goes in the book.
Rob Walling:
And that’s a big thing that I did. I mean, we really leaned into YouTube about a year ago on MicroConf. And so I’ve been putting out a YouTube video every week of unique content. And it’s a grind. It’s a ton of work in addition to the podcast and all that. But the topics that resonated the most there, I was pulling those in to this book. And the other book that I haven’t mentioned to anyone yet that I accidentally wrote that is also 40,000 words, and it’s a prequel to this. So now I got to figure out am I going to publish another book later this year? But there’s a lot of content.
Channing:
Before you came on, we were talking about your accolades, and Courtland was just going down this long laundry list. And I was like, it’s easier just to start from the negative. What hasn’t he done? And now we get to add to that list that you accidentally wrote a book. What does that even mean?
Rob Walling:
Yeah. I had this outline and I’m like, I want to cover everything in the SaaS Playbook. And it’s all the way from, I don’t even have an idea all the way to talking about exits and mindset, the whole lifecycle. So I start at the beginning and I’m writing about ideas and how to come up with them and how to validate and how to evaluate and how to find your first customers and just all that pre-product market fit. And eventually the book, it was just too damn big. And I realized the weaker part … Or maybe weaker is not the right word, but the more amorphous part of it where it’s kind of hard to be super prescriptive is everything before product market fit. Because product market fit onward, that’s what I do every day. I’m in it, right? TinySeed, that’s a lot of the higher end MicroConf founders, and that’s what the SaaS Playbook focuses on is at least some weak product market fit. One to 5K, one to 10K MRR and how do you then go from there. Rocket ship it.
Everything before that I had about 25,000 words and I was like, this just doesn’t belong here. So I just put it in a Google Doc somewhere. And then when my writing coach and I got done writing SaaS Playbook, she’s like, “Do you want to circle back on this stuff?” And I was like, “Yeah, we could flesh that out. Let’s just add it. I think if we add a few thousand words, it’ll be done.” And now it’s like 45,000. I mean that’s a 210 page book. Right now that tentative title is Idea to Traction. And I don’t know what I’ll do with it. Maybe I’ll publish it later this year, early next year.
Courtland:
Well, you did something with this book that I rarely see in our niche, which is you launched a Kickstarter. You’re only the second Kickstarter that I’ve ever backed. You and one other project in the last 10 years. And it’s crushing it. I mean, you’ve got I think another week to go on the Kickstarter and it’s already at $80,000. So it’s more than recouped your initial investment. It’s basically like you’ve paid yourself an advance that an author would have to go beg a publisher for usually, but you’ve done it through Kickstarter, which is super cool. And I’m wondering why you did that because I’ve just never seen anyone do that. Usually people launch on their email list or they just host their own presale. But you’ve used this platform that is super popular, but what’s the advantage? Why launch on Kickstarter?
Rob Walling:
Yeah. It’s a good question because I really went back and forth on it all the way up until the week we launched because all the books I’ve launched prior have been exactly what you’re saying. Set up a landing page, put a Stripe buy now link and have a few tiers. There’s one with a video and one with a blob that’s more expensive. And that’s how I’ve always done it. This time around, there were a couple reasons. One, I really wanted to be able to offer a bunch of tiers. Seven different things. There’s a live talk to Rob option. And that starts to feel weird on a landing page, but in Kickstarter it’s native. It was just really obvious that I … Because I don’t do one-on-one consulting ever. One-on-one advising outside of TinySeed. But I was able to offer, I don’t know, I remember five, six, seven slots of that.
Courtland:
Dude, you sold out for hundreds of dollars. You sold out immediately. You should have charged thousands.
Rob Walling:
I think I should have just offered more slots. So I really did want to have that option of just doing it, of seeing what happened. The second thing was I like learning. I like doing new stuff that I’ve never done. And doing yet another launch to my email list, that’s fine. I’ve done that a lot. But actually trying to do a Kickstarter, I was like, I don’t know. What does this entail? How hard is it? What goes into it? And the learning that I’ve had from that I think has been really cool. So there’s a bit of personal satisfaction there. The other reason is I’ve never had a hardback book. It’s always been soft cover because hardbacks, you got to order a 1,000, 2000, 3000, ship them over. It’s like a bunch of work and oftentimes it’s a four to six month delay. And so Kickstarter’s kind of designed for that.
It is a pre-order thing. I could have ordered two or 3,000 books and paid for them, but I didn’t want them sitting in my garage. So this is a way to do that. And lastly, I view Kickstarter as a community/ it’s not quite a social network, but it’s kind of. And I have exposure on Twitter. I have exposure and podcasts. I have exposure on YouTube. I’ve backed 275 Kickstarters, but I’ve never run one on my own.
Courtland:
Whoa.
Rob Walling:
Yeah, dude, go to my page. It’s embarrassing.
Courtland:
Good lord.
Rob Walling:
It is nerdy as hell though. It’s all not video games, it’s like tabletop gaming and stuff I play with my kids. And there’s certain slider belts and watches that I back to, but it’s a lot of nerdy stuff.
Courtland:
What’s your favorite thing you’ve bought on Kickstarter?
Rob Walling:
There’s a game. I think it was a kick … It was a crowdfunding. I’m not sure it was on Kickstarter, but it’s a game called Kingdom Rush Rift in Time that is based on … Kingdom Rush is one of the best iPad games, and it is a tabletop version of that with these … It’s like 125 bucks when I backed it. And it’s these great minis and endless-
Courtland:
You’re not messing around.
Rob Walling:
And my kid painted them. My 16 year old painted them and we’ve just had endless hours of fun playing with that one.
Channing:
That’s awesome. You have kids that you can have an excuse for you to get those things, but I would just get them and just be a 36 year old man with tons of tabletop games.
Rob Walling:
Totally. I know. I’m so glad that … It’s like having kids is tough, but this is the best time was when my oldest-
Channing:
It’s the excuse.
Rob Walling:
Exactly. It’s an excuse to like, I’m going to learn to play Dungeons and Dragons again. I hadn’t played it since the ’80s. I’m going to get into comic books and Star Wars stuff. I would never make time for that stuff if I was-
Channing:
I need a kid. I need a kid for the sole purpose, I have this omnidirectional virtual reality treadmill in my gym in the other room, and whenever anyone sees it, they go, “What the hell is that? Are you an adult or are you not?” I just need just a kid that’s just not even really my kid. A neighbor just to come and be like, “No, no, no. I got it for this kid. It’s like a charity thing. It’s not really my thing.
Rob Walling:
You need a nephew or a niece. Yeah.
Channing:
A nephew. There you go.
Rob Walling:
That’s awesome, man.
Courtland:
Thinking about Kickstarter, I wonder if … If you look at our niche, Indie Hackers, Bootstrap Founders, there’s not that many places where we launch products. It’s like Hacker News, Twitter, our own email list, product hunt. There’s only a few. And I feel like that number hasn’t changed in years. It’s kind of just the same. Especially if you want to launch to your customers, of course there’s lots of different channels. Some people are really good at SEO, some are good on YouTube, some are good on TikTok. But internally, when we want people in our own niche to support us, there’s those four places. I feel like I’m blanking on any others. I wonder if there’s room for another one. Channing, maybe we should build this. A Kickstarter for Bootstrap Founders that’s slightly different than Product Hunt that is a different model, but something that people understand so we can kind of support each other and invest in each other’s launches in a way that’s easy.
Channing:
Yeah. And just have more surface area for the discovery function.
Courtland:
And I like this idea of putting a credit card into it. One of the reasons why Kickstarter is good is because people like Rob who’ve already backed hundreds of Kickstarters when there’s a new one. There isn’t all this friction of, okay, I got to sign up and create another account and yet another website, et cetera. It’s just like, boom, click a button, click pledge, already in there, payment’s gone and it’s super simple.
Rob Walling:
I think that’s a really intriguing idea. There’s obviously all the logistics of well, what if they don’t deliver and all the same crap Kickstarter has to deal with. But the idea of bringing it to our space I think is … It’s kind of a novel way of thinking about it.
Channing:
I’m to say, Rob, also the idea of you going into Kickstarter is really smart. We just had Wes Kao on. She runs Maven, the online course platform, and she had had this idea where she’s like, “Look, there’s a pyramid of ways that you can deliver content to your audience and the higher up the pyramid you go, the more high touch and profitable you can get and obviously there’s higher stakes.” And she placed a book toward the top of the pyramid. The bottom is maybe sending a quick tweet where you don’t have to defend the things that you say, but then above book, she’s like an online course or you’re actually live with your audience. And with your Kickstarter, you actually get to segment out. You don’t just have this book that’s something you’ve already written, there’s nothing you can really add. You get the ability to have those tiers. So I really like that idea as well.
Rob Walling:
There was a MicroConf talk by Ryan Delk years ago who used to work at Gumroad and he had the typical launch for a book like this is you have a 1X, 2.2X and 5X price points. So if your 1X is 40 bucks, 2.2 is about 90-ish or 100 and then 5X going to be around 200 and maybe do 250. And then you figure out what’s worth 40 bucks, what’s worth 100 and what’s worth 200? And that is kind of how I approached it, but also I realized I don’t want to get on a one-on-one call for 200 bucks. I just can’t justify that. So yeah, there’s an $800 tier and then there is a $5,000 tier to come for two days to Minneapolis this summer and actually do an in-person thing, which I think in your pyramid would just stack on top of that. It’d just be up. I’ve never done one of those aside from MicroConf, so it’s certainly going to be an adventure.
Channing:
Are you open to sharing how many people have taken you up on those offers? How are you doing so far?
Rob Walling:
I had five slots and I think three are booked for five grand a piece, which would be a great … I mean anywhere between three and five is a good number. My fear was A, it would be zero or one. And it’s like uh-oh. Me and this person are just staring at each other for three days in Minneapolis.
Courtland:
Do you know who the backers are who got those slots?
Rob Walling:
Not yet.
Courtland:
Ooh. Total mystery.
Rob Walling:
I don’t think we learned … I know. It’s a trip. And what’s funny is my brother who lives out in California sent me a text and he’s like, “Hey man, if I bought back one of these in-person retreats, does that include a trip to Parler Burger,” which is a famous Minneapolis place. And I was like, “Heck yes, it does.” So I honestly don’t know if … One of them might be him. I have no idea.
Courtland:
It could be us.
Rob Walling:
It could be you.
Channing:
Here we are.
Rob Walling:
Could be anyone. I’ll know in nine days I guess.
Courtland:
So let’s talk about the book itself. You described it as what to do once you have product market fit. And obviously you have a pretty good perspective on this. You run TinySeed. You seed dozens and dozens of companies that you work with personally every day to help them basically grow their startups. How do you figure out what goes into this book? I’m sure there’s a lot of people listening, us included, who want to know what do you do once you have a big audience and your product has struck the market and you kind of have this elusive product market fit. What now?
Rob Walling:
Yeah, no, it’s a really good question. And it’s one I had only been through once or twice before running TinySeed. And I had been had in conversations and affiliated with folks at MicroConf. But you’re right, I’m really inside a bunch of businesses now and so I’m seeing the patterns. The book really starts off talking about, hey, even if you have weaker product market fit, here’s how to think about talking to customers and strengthening that. And it’s some stuff people have heard before and it’s also some of my unique thinking. But then I went through all the advice that I have emailed to founders. Every time I would post to Indie Hackers, I would take that post if it was a response to someone’s question and I was throwing this all in a Google Doc. And I realized there were patterns.
Talk about content reuse. There were patterns to what people were asking. Like, should I compete in a really competitive niche? How do I compete with big competitors? That’s a topic in the book. Pricing. The number two chapter after market is pricing because most founders screw it up. We under price our products and I talk through my psychology of pricing, what I see people doing well, what I see them doing poorly. And then of course marketing’s a huge one. Little different for Indie Hackers because your community much MicroConf. I don’t necessarily think about marketing beyond the content we produce, but if you’re a SaaS app, a B2B SaaS app, the hardest thing is what do I do? What do I try? What do I try in what order? And I have a whole chapter on that. I have a three factor framework of speed, scalability, and cost I think. I forgot what the third factor is, but it’s a whole mental map that I’ve developed of, hey, there are only about 20 B2B SaaS marketing approaches. These are the ones you should try in this order based on what you want to accomplish. And then I talk about hiring, building your team, tracking metrics. That’s kind of the high level.
Courtland:
I have a friend who’s an investor who who’s telling me his theory that it’s basically becoming harder and harder to build a successful SaaS business. And his idea is here’s why. There’s more competition than ever. 10 years ago, not that many people were building SaaS businesses, not that many people knew how to code. Tech startups seemed like a difficult thing to bust into, especially if you’re self-funded. Today, there are dozens of businesses for every product idea. The playbook for starting SaaS businesses is out. You literally wrote the playbook. Other people have written the playbooks. People have mapped this out and they kind of know how to attack a different distribution channel, et cetera. But he argues even as there’s more and more competition and more people starting things, the number of channels for marketing your product is not really growing as quickly as the number of people who are trying to do this thing. So everything’s becoming more competitive. Ads are becoming more expensive, the bar is getting higher and higher to do good SEO. Every company’s inundated with sales calls because there’s so many people doing sales. In your experience, is this true? Is it getting harder to start a SaaS company?
Rob Walling:
I would say yes, but it’s not hopeless. Is it slightly harder than a few years ago? Yeah. I honestly think everything that you’re saying is accurate. The content bar, especially with AI now, but even before that. 10, 15 years ago, I could hire someone to put out articles and just build links, almost buy links from what were they, blog networks or whatever. And you could rank in Google and you can’t do that anymore. So it is more challenging. I do think that’s where raising a bit of funding has become more and more in my head. I think if you get traction, it’s probably something you want to think about. Even if you’re a hardcore bootstrapper like myself, it just becomes hard to organically grow a business in the ways that we used to. With that said, there’s a flip side to this. We still see tons of companies apply to TinySeed that are competing in spaces where the competition is much less.
So Builder Prime is a CRM for home improvement contractors. And when I first heard the idea, I was like, “Ooh, that’s a tough market to sell into. How are you going to find them and how are you going to close them? Customer pain, right? Oh, nontechnical, and all this.” And he’s crushing it, just absolutely crushing it because he’s executing really well. So it’s the people. There are a lot of people starting, a lot of people trying things, but I still see Ruben Gamez with SignWell. I see Derrick with SavvyCal. A lot of folks we know and then a lot of folks you haven’t heard of that are in TinySeed, like Iran is the founder of gymdesk.com. And that’s another one where it’s like, well, aren’t … It’s booking scheduling software, management software for a gym, martial arts studios, all that. Wouldn’t you think that’s a solved problem? And yet, the dude is growing like crazy. But it comes down to you have to execute probably at a higher level than you did 10 years ago, but it’s still completely possible.
Channing:
There also seems like there’s a huge out of that challenge is finding a smaller niche and not just sticking with a market as it seems to declare itself to at first. There’s a really good anecdote about Gary V, who had some conference, he gave a talk somewhere and there were 400 people at the conference. And he goes, “Well, hey, listen, at the end of this conference, I’m going to give a one-on-one one hour coaching session to somebody. And this is an auction for charity. The bid starts at $500.” And at first all 400 people in the room were like, okay, well, we’re bidding it up maybe $50 at a time and then everyone started to fall off except for two people at the end who just really, really wanted it. And they just kept going up by $100 to the point where everyone was so restless that he was like, “Okay, well you’re both at 4,000. Would you both just pay me 4,000 and I’ll make it each of you get that. Can we just settle this here?” And so in a way, you could say, well, look, the market was everyone in the room and the supply and demand placed his little coaching session at whatever, $800. But really the market was two people.
Courtland:
At that price point. Yeah.
Channing:
Right. At this new price point. And so I kind of feel like one easy way to miss out is to go, oh, well, we can’t build a SaaS in this space because it’s so overcrowded. Because you’re just looking at the market as it’s been designated by everyone who’s come before.
Rob Walling:
I just recorded, or I think I released a podcast episode this week about positioning, and I was talking about positioning really is figuring out where there’s a gap in the market. Where is the corner of the market between … Sometimes it’s like, oh, there’s tools out there, but they’re too expensive and they’re hard to use. Is there an opportunity for a Drip or a ConvertKit to come in and kind of swoop in under. And we both got a lot of traction because of that. Or we see it with another electronic signature tool? Isn’t that a solved problem? And yet, SignWell’s crushing it. And there are reasons. Because he found out some unique angles, but also because he positioned himself well against the incumbents and people are a little tired of them. So I agree with you. I think the other thing too is it is more competitive, but the markets are all growing.
The market for email service providers compared to 10 years ago has got to be two or three times what it is. So there are more customers in these spaces, even though the marketing is more competitive, the channels are competitive. But I think that’s where people need to have some type of differentiation. The biggest mistake I see is someone trying to build the exact same thing as a bigger competitor. And they’d be like, “Well, the market’s huge. I just need 1% of it.” It’s like, no, no one’s going to sign up. You have to be opinionated and either have unique feature set or unique positioning and be like, we are really good for this subset and not good for everyone else.
Channing:
Exactly. Yeah.
Courtland:
I watched your video on Kickstarter where you’re marketing the book and you go through a list of different things that are included. I want to talk about a few of them. You have mindset, you have product market fit, you have marketing, you have new ways to differentiate and compete. You just mentioned that last one. New ways to differentiate and compete. So how do you do that? You said have an opinion, you can’t just be the same as the incumbent. What works in terms of differentiating yourself and what doesn’t work?
Rob Walling:
Usually early on, everyone says, “We’re the simpler version of this.” And that-
Courtland:
We’re that with no features.
Rob Walling:
Is kind of a cop out. Exactly. It’s usually-
Channing:
We’re the cheaper.
Rob Walling:
Right. We’re cheaper or simpler. And it’s like, okay, maybe for now, but really that’s not a durable advantage. There’s a couple angles. The one most of us think of is to pick a vertical. I’m going to be scheduling software for hair salons or for gyms instead of scheduling software for everyone. That’s kind of the most obvious. There are a couple others that if you’re in a big space with hated competitors, what you’re trying to look for is where are their achilles heels or where are their weaknesses? So as we were building … I’m going to use Drip as an example, even though it’s older because I did exactly this. We were undifferentiated and we were plateaued. We did not have strong product market fit. And then what I found out was these marketing automation providers were pretty expensive and they were hard to use and their sales process sucked.
They made you go through multiple calls, they made you pay a $2,000 onboarding upfront. A lot of them made you pay annually. And so I kept saying, is there a way to make not simpler software, but much easier to use software to remove that frustration? Is there a way to just have self sign up if you want it? And is there a way to still be super profitable, but under price them? Right? I’m not going to be Walmart. I’m not the low price leader. But they were charging outrageous. I mean, the cheapest one was $400 a month, and most of them were two grand a month and up. So this is a way to do it is how can we take something that enterprises are using now and paying a lot of money for and make it more accessible to the masses? So I think those are two. There’s other tactics there, but-
Channing:
And it sounds like if you reduce your operating expenses, so if you have an option where you don’t have to provide all of this onboarding, then that’s a way where you can build that into a lower price without cutting into your margins.
Rob Walling:
And it also becomes, if you’re competing against big hated competition, oftentimes their cost basis for everything, including their software. They were not on AWS because they launched 15 years ago. There’s I think a lot of opportunity there.
Courtland:
What about mindset? This is a big topic that I think a lot of people underestimate when they first become founders. What have you seen that helps people have the right mindset to basically succeed with their business?
Rob Walling:
I mean, there’s a lot to it. It depends on your own psychology. Some people like me are naturally more stressed or anxious. When I was running my last startup, I was like, “Ugh, I’m stressed. Everything’s going to be a deal ender.” And I had to learn to not make speed bumps into roadblocks. So some folks need to hear that, hey, it is not going to end your business. Most things are not going to end your business. Take a deep breath. We’re almost trained in life to go to school and then get a job and then go to … Well, you go to school and go to college and get a job. And you’re not faced with crises on a daily basis. But as a founder, you kind of are. And sometimes I find it’s hard to pick which of these crises are catastrophic and which are just not that big of a deal. And so I think that’s a big thing that I help founders with these days is I will do a call with a TinySeed founder and just say, “I know you’re stressed and I can tell this is a big decision. You’ll figure it out. Just know that you’re going to figure this out. It’ll work out.” I think being able to roll with things that feel difficult, but actually realize that they’re not business ending is a big one.
Courtland:
Where’s your mindset at nowadays? I mean you’ve been in the game for 15, 20 years, you’ve got a million things going on. Do you ever get disillusioned? Do you feel like you have more energy? How are you feeling?
Rob Walling:
I feel like I’m living my best life, and it’s because I’m working on what I want to do. And I do not take that lightly. I worked hard to get here. I got a little lucky to get here, but the best decision I made after selling my last company was to take six months off and say, what do I really want to do? Because I do see entrepreneurs sell their businesses and then start another one and do the same thing, and they don’t really want to do that. And that would’ve been a mistake. If I was running hardcore right now, pushing on a SaaS app, I would not be happy. It’s just not what I need to be doing at this stage and age and with the age of my kids. So for me, I looked back at what have I been doing for free forever? And it was writing about entrepreneurship and it was having a podcast about startups, and it was writing books, and it was starting a MicroConf, which made no money for several years. I almost walked away from all that at one point. Got a cash offer for MicroConf, and I was like, oh … This is 2018. I was like, “Oh, I could just walk away from all of it.” And then I realized, what am I doing? That’s like my legacy.
Channing:
That’s what you love. Yeah.
Rob Walling:
Yeah. So that’s what I’m doing. I mean, that was one of the reasons. It was like, okay, well what if I double … I did a what if. What if I double down on MicroConf? What if I double down on the podcast? What if I double down on all this stuff? And that’s where TinySeed started percolating as I talked to people of like, yeah, could you run an accelerator for bootstrappers? And it’s like, what would that look like? So I feel great these days.
Channing:
Courtland, you just quote tweeted someone. Someone mentioned, and no hate on them, they were like, “Look, now that Indie Hackers is independent again, if I were CS Allen and Channing Allen, I would list on listen on MicroConf,” or MicroAcquire. MicroConf. “And sell it again to someone else, this time for 10X. Could be a great success story.” And Cortland cheekily quote tweets this guy and goes, “The best success story is finding work you enjoy for a lifetime. Even if you sell and get a big payday, what’s next? You start experimenting and trying to build a life you enjoy. Of course. That’s always the end goal. Money’s a tool for that and not a destination.” And in a sense, I think of two things that you just said, Rob. On the one hand, you had the experience or the privilege or whatever to take a step back, take a satellite view and say, well, what do I actually want before I just jump into something?
But then the first piece, which is if you have a little bit of a temperament for being anxious and everything is a fire, well, when the house is on fire, you don’t have time to stop and navel gaze. And so putting those two things together, if you’re able, and it’s all in the how ultimately, but if you’re able to see a small fire raging, a little bit of an ember, and go like, “All right, I could put that out, but I really need to think about what I’m going to do after I put this fire out and then I put the next fire out. How do I build a system, for example, where I’m not really dealing with fires?” That’s the really difficult balance to strike.
Rob Walling:
That’s right. And it’s something I didn’t do well until I left Drip, until TinySeed, MicroConf. We have budget, but I also have experience to put the right people in place, such that producer Xander runs MicroConf day to day. And Tracy Osborne does a lot of the running of TinySeed. And that allows me to work on exactly what I want to work on, which is not a luxury you have when you’re bootstrapping a SaaS. You just have to do everything until you have money to hire it. And if you’re bootstrapping, you never have enough money to hire, which you really need.
Courtland:
There’s this, I would describe it as a scarcity mindset around coming up with ideas, where a lot of founders, myself included, for the vast majority of the time I’ve built stuff online, think that it’s very hard to come up with an idea for something to work on that can both make money and that can align with things that you enjoy doing. And so you got to choose one or the other. And if you’re a broke ass founder, your first time out of the gate, you choose the one that makes money. And so you see a lot of people starting companies that they would never want to do a second time after they sell the first time. Do you think that that is kind of a true dichotomy? Do you think it’s reasonable as a founder to think, okay, what am I going to enjoy running for the rest of my life and what will make money? Or do you think you have to go out there, build something that’s successful, and then once you’ve got your nest egg, then figure out what you want to do and build a company that aligns with what you want to do for the rest of your life?
Rob Walling:
I think that you have to enjoy the process of building a business, and you probably want to like your customers, but I don’t like the mindset of I have to build something that I don’t really like in order to make millions so that I can work on what I want. Because you got to enjoy the journey, but also the journey sometimes is not very fun. And so what are you going to hang on to during those not fun times when you’re grinding it out or when Russian spammers get all your IPs blacklisted on a Sunday night, as happened to us in 2014. And I wake up and I’m like, “Well, guess we had a good run. We’re done.” I literally was like, “I think we’re done. I think we’re going to have to shut down.”
Channing:
That’s it.
Rob Walling:
That’s it. Drip is no more. So do I love dealing with email deliverability and IPs and blacklists, and-
Courtland:
Is that your dream?
Rob Walling:
No, don’t. But I really love building businesses and thinking about them and solving hard problems creatively. Because there was constantly hard problems that we’d have to sit down and say, whether it’s how do we get our IPs unblacklisted? Or it’s we have these 50 feature requests and they’re all kind of related, but they’re all asking for different things. How do we turn this into a visual workflow that answers all of them? That was a super hard creative, almost engineering mindset problem to solve. That’s the part that I enjoyed the most. And so I think that’s what I’ll say is I could have run a business for gyms or for hair salons or whatever. It’s still creative problem solving. But I think the two things you want to love is building a business, creative problem solving and your customers. I do enjoy working with entrepreneurs, and it’s like if you don’t want to deal with hair salon owners, then don’t start a business for them. Because Patrick Mackenzie talks about this with Appointment Reminder.
Courtland:
And Bingo Card creator.
Rob Walling:
And Bingo Card, where it’s like he did it for the money and he learned a lot, but as he quickly learned, these are not the people I want to talk with every day. I think that’s something that a lot of people make a mistake around.
Courtland:
There’s this book, Channing, remember you recommended to me from Strength to Strength?
Channing:
Yeah.
Courtland:
And it kind of starts off by saying, look, if you’re reading this book, you have made it, you know are at the top of your field in some area, you’ve been a success. Congratulations. But what do you do now? This book is for people like you trying to find their second peak in life. And he studied all of these famous people from Charles Darwin to Johann Sebastian Bach and recognized a certain pattern that when people are younger and they’re sort of getting their first success, that’s when they seem to have the most energy sort of grind it out and to do this very hard, often creative or even mathematical work to try to figure it out. You’re trying to figure out how do I combat spammers? How do I push into this new market?
But once people get older, if they keep trying to do that same thing over and over, they tend to meet with less success. Like Charles Darwin, everybody knows him because he created the Theory of Evolution, but people don’t know is that he died tremendously unhappy because he kept trying to top that success and come up with new theories, which no one ever really knew anything about when he sort of died alone and unhappy. Versus others, which is tragic. I don’t why you’re laughing.
Channing:
Because it’s so tragic.
Courtland:
But I think that’s common. But I think the more successful approach that he talks about is as we get older and we have gained all this knowledge from our earlier wins, is to move into a much more social role, a much more teaching role, a role that aligns with our strengths, which as we get older is the fact that we have a ton of experience and wisdom and knowledge, much more than anyone younger has because they just haven’t been out there. Whereas at the same time, our horsepower’s slowing down quite a little bit. We’re a little bit more resting on our laurels. And so it’s not surprising to me to see this transition of a lot of people who do this crazy SaaS startup at first, and they’re fighting through all these thorny problems that aren’t really their life dream. And then later on when they look back and see what they enjoy when they want to get started again, it’s running conferences, doing one-on-ones and office hours and talking to people and just generally giving back and helping other people. And once you’ve sort of achieved that nest egg, you also have the clout to do that and make money from it because people will pay you $5,000 to go on a retreat with you because you have those wins under your belt.
Rob Walling:
Yeah. I’m really honestly impressed or surprised by the people who do just keep starting and starting. David Cancel’s on his fifth, I think company. And even AD PNR did Woo Themes, which became WooCommerce and then did Conversio and sold that to Campaign Monitor and now is on his third or fourth. And he had a couple that failed. And I’m like, I respect that, but that’s not me. But I’m also a lot older than AD, I think. So David Cancel is just an anomaly to me. I’m like, this guy’s unbelievable.
Or even, I guess Jason Cohen had three and he had a small success up front and then a bigger one. And then WP Engine has been the last 12 years. But I couldn’t see him doing another one after WP Engine, but maybe he would. But exactly to your point, I see a lot of entrepreneurs doing that. I mean, there’s a reason that TinySeed mentors … The mentor list is a lot of founders who have exited because they want to participate and give back and still be in the game, so to speak. But they don’t want to be the … They know, it’s a cliche, but I’m too old for this … That’s how I feel of actually being in the heart of it. I’ve done it for too many years and it doesn’t sound fun. Could I do it? Could I pull it off? Yeah. Do I want to do that? No.
Channing:
And see, that’s the big change. What the author of that book talks about is in the beginning, whatever, in your first 30, 40 years, you have a lot of fluid intelligence. You’re really creative. It’s easier for you to come up with the ideas and then eventually you have crystallized intelligence so it’s easy for you just to kind of … The wisdom that you’ve gained. But you’re saying for you, it’s not that you couldn’t, you’re just like, nah, I’ve been there, done that.
Rob Walling:
Or maybe I couldn’t and I just don’t know it. I do know that running TinySeed and MicroConf is still … When I first meet people and they say, “What do you do?” I say, “I’m a startup founder. I run startups.” That’s what TinySeed and MicroConf really are. TinySeed happens to have raised funding to invest in other startups, but internally we have engines that we’re building. We have marketing engines in MicroConf. It is different than running a SaaS, but is still a lot of problem solving.
Channing:
These days, I’m curious about you. What drives you? Are you driven by making more money a lot? Is it just the process?
Courtland:
Yeah. Because I think everyone has their own formula for what brings happiness, what motivates you. When I was younger, I wanted to be a success. I think now we’re sort of talking about the second peak in your life and it’s a lot more driven for most people by what makes me happy. What’s on your checklist for what makes you happy?
Rob Walling:
It’s a really good question, and it’s one that I grew up my whole life wanting to be able to work on whatever I wanted. I wanted freedom. The money never mattered, but I needed money to be free in my day job. I mean that’s-
Channing:
Like a constraint, not a goal.
Rob Walling:
It is. Exactly. And so my goal since I had my first job when I was a teenager was like, I want enough money that I never have to work again. That was it. And I don’t need more. Some people do need more and they’ve driven by the money and I haven’t been. The money’s nice. I have a house and a car and that’s great, but I achieved that point in 2016 in essence, where it’s like, okay, I literally never have to work again, but I’m going to work. So what am I going to work on? And that was the big come to Jesus moment, so to speak, of I went on a founder retreat and was like, I think I’m going to step away from all this. And I actually started talking to the number two board game/tabletop gaming website in the world in terms of traffic and reach, and I was going to acquire it from him.
And I was like, how much revenue do you have? I was going to go all in on tabletop games and all this. And then I had that moment I talked about earlier where I was like, no, that’s fine, but I’m going to regret this if I do this.
Courtland:
Would you?
Rob Walling:
Oh yeah. I would get into tabletop gaming and be happy for a couple of years and then the margins are terrible. You know what I mean?
Channing:
Sure.
Rob Walling:
Money is still a scorecard. It is. That’s something I think is a pro and a con or a strength and a weakness of me is that I have a tough time doing things that don’t involve money, even though the money doesn’t motivate me per se. But just doing things … Even my hobbies, I collect collectibles. I have this Beatles gold record back here. And I bought it, and it’s worth more than it used to be and it’s like, I’m never going to sell it, so that doesn’t matter, but somehow the money … It is.
Courtland:
Gives you a little jolt.
Rob Walling:
Yeah.
Channing:
I have to say, I want to write a novel, I’m working on a novel, and I feel like the fact that I’m trying to write a novel must mean by a logical extension that I don’t really care at all about the money.
Rob Walling:
Totally.
Channing:
But the thing about that though is one of my strongest convictions … I think that one of the things that I root for for everyone is to get to a point where they make the amount of money where they don’t have to think about money anymore. Not because, oh cool, now you’re going to have money, but it’s like every single time I’ve seen someone have that transition, they then have to stop and say, “Okay, but what do I want for myself besides money?” And it’s like this self realization that I feel like you can’t ever have good clarity around that until you reach that goal.
Rob Walling:
Yeah. And that’s the thing is the people I know who are doing it for the money, when you get there and you make 10 million bucks, 15 million bucks, what next now? Are you just going to do it for more money? Because I don’t know that you’re going to be happy. I think probably all of us know decamillionaires who are really unhappy. That sucks to have worked all that time and to be a whatever, a one percenter, a three percenter. Some of the most wealthy people in the world have that luxury and yet still not be happy. I think that’s a travesty.
Courtland:
Yeah. I know on my checklist, I’ve got four or five items on there that tell me I’m going to like working on this. And one of them is that there has to be some number that goes up. I don’t know why. I don’t know where that comes from. If I was a writer, Channing, maybe it wouldn’t be money. Maybe it’d be the number of readers or copies sold or something. But if there is no cumulatively growing thing, then I just get this weird feeling in the back of my head that I’m not really building anything. What’s the purpose? And so money in a way, when it ceases to become the primary motivator, it’s no longer, I need more money to be free, does become this scorecard. But there’s healthy and unhealthy ways for that to happen I think.
You’re the Scrooge McDuck character and you’re just collecting more and more money, but you’re unhappy because you have no idea what you want to do with it except put it in a room and swim through your vault of gold coins, then that’s unhappy and that sucks. But if it’s like, okay, well this is a way for me to measure my progress and feel good like I’m accomplishing something, then I think it can be healthy. And then you can always spend your money to do other things. Invest in other entrepreneurs, pay it forward, help out friends and family, et cetera because it’s not about spending it on yourself that matters. It’s just a motivational thing.
Rob Walling:
Yeah. I think that’s a big one. A number going up is something I think about a lot too. And this is going to sound maybe contrived or cheesy or whatever, but I realized at a certain point I really like making an impact. I really like impacting people. And the more people I can help or impact the happier I am. And that’s not just bull talk. If you look at my history, I grow the podcast so that more people … Every time I get an email it’s like, thank you. I get these emails and It’s like, “You changed my life. I had no idea what I was doing, I built an MVP, I just sold it.”
There was a guy in Romania or somewhere, very little cost of living who’s like, “I just sold it for half a million dollars. I can almost live the rest of my life on that and it was basically following your advice.” I made no money off of … They’ve never come to a MicroConf. I don’t care. I care that his life is better. Is that a bit of a luxury? Yeah. I have that. I don’t need to make money off him. But that’s where the numbers that go up these days are YouTube subscribers or podcast subscribers. If those are stagnant, I’m just like, so who am I helping then? What good is this? How am I making a difference in the world?
Courtland:
Yeah.
Rob Walling:
I wanted to ask you guys about the whole Stripe thing. Is it a weird transition to do this?
Courtland:
Yeah. No. No. No. We can talk about whatever you want. That’s why I love interviewing another podcast host.
Rob Walling:
Because we can just turn the tables. Yeah.
Courtland:
Exactly.
Rob Walling:
So I listened to your last episode. I saw the announcement Indie Hackers is Indie Again. I listened to your last episode. And I know you can’t divulge details of the deal, which I’m not going to ask about, but I totally get why you guys would do this because I would feel the same way. I know even no matter how good the parent company-
Courtland:
But why would Stripe do this?
Rob Walling:
That’s the question. And I believe Stripe approached you about it.
Courtland:
Yeah.
Rob Walling:
So is it a focus thing? I have my own theory of, well, markets are going down, I know they took a haircut on valuation. Are they just trying to focus? What’s the logic there?
Courtland:
I think it’s tricky to talk about. You’re right.
Rob Walling:
Yeah.
Courtland:
But I think at the end of the day … I know this also sounds cheesy, but people at Stripe are just really good. They are not very miserly. They’re not penny-pinching trying to save every nickel and dime. And I think Patrick in particular is pretty wise about the overall concept of branding and reputation. Compared to other big unicorn startups of its size, Stripe has remarkably small number of bad press stories, et cetera and that’s deliberate. It comes from the top because everyone at Stripe is conscious of making sure … We have what’s called the front page test. If what you’re doing appeared on the front page of a magazine, how would you feel about it for the company? And that takes precedent over, okay, how much money do we save this quarter or this half or something?
And so I think for Patrick, he’s just looking at Indie Hackers and looking at who we are and what we’re motivated by and how we feel. And a large part of it is like, hey, are you guys happy? Are you doing what you want to do? Do you still have the same fire? Do you still have the same drive? He’s asked me that question every single year that we’ve been at Stripe. And I think we could have stayed. We could have just continued doing exactly what we were doing. And Channing and I had to also go back and do some soul-searching and be like, well, are we happy? Would it be better if we owned Indie Hackers? That was never an option before. What would we do in that case? And what would we need to feel like it was even a fair deal or a good deal because Indie Hackers burns through a lot of cash. I don’t want to jump ship and then suddenly be losing money every month. And so I think it was just a hodgepodge of, it was just convenient for both parties to figure out a good deal for that. And here we are in this crazy situation where we owned this time last month, 0% of Indie Hackers, and now we own way, way, way more than that. And it’s just cool. It’s cool to be here.
Channing:
But I was going to say another thing from Stripe’s incentive perspective just aligns with the weird circumstances around them acquiring us in the first place, which is that if we do what we are … If we inspire a lot of new entrepreneurs and we help to educate a lot of entrepreneurs to be more successful, that’s a common rising waterline that lifts all the boats. And so that’s what we were doing at Stripe. We weren’t making a lot of revenue. It wasn’t a financial acquisition where we were raising their bottom line in that way. If we are healthy and happy and inspiring more entrepreneurs and doing what we are really designed to do better, then that helps with what Stripe actually wants from us. So us being cut loose, us being independent and having the energy to go 100% on Indie Hackers is directly in Stripe’s interest.
Rob Walling:
Yeah. And that’s a really mature way of thinking about it, and I would expect Patrick or Stripe in general to think about it that way. It’s a long-term way of thinking. It’s as you said … I know they talk about raising the GDP of the internet. And if you’re able to do that better independently … I was going to say before you said it of I know Stripes not making buckets of money off Indie Hackers.
Courtland:
No. No.
Rob Walling:
That was not the play. The play as I saw it years ago was, hey, we want Indie Hackers to stay alive and or … I think at the time you were running ads, and I think Patrick was like, “Ah, it’ll grow faster without ads.” That was my mental model of why they acquired you. Is they want MicroConf to exist. They want Indie Hackers to exist. I don’t know if you guys were there at the MicroConf where I was either talking to Patrick or John Carlson on stage, and I said, “Raise your hand if …” SaaS companies all abounding. And “Raise your hand if you use Stripe.” And it’s like 90% of the … Yeah. It was crazy, right?
Courtland:
Yeah. Yeah.
Rob Walling:
I totally get that it’s good for them. Companies don’t think that way and that honestly is one of the reasons I have respect. Tons. Just loads. They run it. I have similar respect for Ben Chestnut at MailChimp. There’s only a handful. Dharmesh at HubSpot. There’s a handful that I’m like, you are super legit and you are very wise, and you make decisions that are very mature.
Channing:
Also, Cortland, do you remember? I think it literally was the week before Patrick reached out to you via email to ask about acquiring us, you and I were posting on the forum about new business model ideas we were thinking of, and one of those ideas, and this was at the top of the forum, was pay gate Indie Hackers. I don’t know what the name of the post was, but we were like, okay, why don’t we do a membership thing? Because we were just looking at revenue and a lot of our revenue ideas-
Courtland:
You own a community, you have to at least consider that.
Channing:
Yeah. A lot of our really public facing revenue ideas that we talked a lot about were 100% going to limit the impact that we had and probably be good for us in the bottom line. But yeah, if you’re a Stripe and you’re like, “Okay, well this thing is really useful for us,” all of those types of ideas are going to be good for them maybe in the short term, but they’re not going to help raise the GDP of the internet.
Rob Walling:
When Patrick approached you about this and said, in essence, would you prefer to be independent, did the two of you have any hesitations around that? Was it actually a decision?
Courtland:
Oh, yeah. Yeah. Yeah. Yeah.
Rob Walling:
Oh, really? What were the hesitations?
Courtland:
It’s nice to get paid a steady paycheck every single week. It’s really nice. It’s expensive to run Indie Hackers. We haven’t been focused on cutting costs that much, nor have we been focused on generating revenue in six years. So how are we going to turn that ship around? It’s risky. What if Indie Hackers dies if it’s on its own? There’s just a lot of considerations. Also, okay, this is an inflection point. What’s our opportunity cost? What if we just quit Indie Hackers and went and did something else? What if I became an investor? What if I decided to go start a different company? What would that look like? Is our heart really in it I think it was a big one for me. I think to some degree the answer is getting to be a little more leaning towards no for me. I’m just not as passionate about this as I once was.
I think the peak passion that I had was probably the very first year where it was like, hey, I have to make this work or I can’t pay rent. And then the next year it was like, hey, I just joined Stripe, I want to be a success and impress people. And those are the two years where Indie Hackers grew by far the most. And so the question was, okay, well if we are Indie again, is that passion going to come back? Because if it doesn’t, this is probably the wrong decision. And so it wasn’t something we just decided overnight. It took us literally a month of talking and figuring out everything we wanted and opportunity cost before we decided we wanted to do this. And now we’re still in the process of, okay, what’s next? By the end of this month, Channing and I were super excited.
We’re like, holy, this is going to be … I feel energy flowing into me that I haven’t felt in a while. So now the question is, what’s next for Indie Hackers? What do we do? The sky’s the limit. There’s a million and one things that we could do to make money, and also to do what you’re saying. To have a positive impact. And then the third thing, which is to enjoy our lives. To wake up every day and be excited about what we’re going to work on, which I think it’s not worth doing anything if I’m not excited to work on it at this point.
Rob Walling:
Yeah. I have a mental model, but it’s just borrowed from other things. Jeff Bezos has the regret minimization framework when you come to a decision. Which am I going to regret least? In my head, it’s usually if I come to a hard decision, I pick the path that will let me either learn more or that’s riskier within reason. Not risky like putting my house on the line, but that scares out of me. Those are the ones that I tend to lean towards. I wasn’t able to do that in my 20s. I was too scared. And then as I matured, I was like, oh, risk actually brings fun. It brings a little a little bit of-
Courtland:
Stakes in there.
Rob Walling:
Yeah. So the two of you as founders, as entrepreneurs, I feel like you would’ve regretted not going independent.
Courtland:
Oh, definitely.
Rob Walling:
I just can’t imagine not doing it. Even though it’s scary and you have to work through it as an emotional process, it doesn’t even seem like a decision to me. It’s just a foregone conclusion that you would do this.
Channing:
Yeah. The risk point reminds me … Have you ever read The War of Art by Steven Pressfield?
Rob Walling:
Yep.
Courtland:
Yeah.
Channing:
In his way of seeing the world, if you look at something and you’re terrified of it, you almost should just assume, I need to go do that thing because I’m terrified. Obviously, this doesn’t apply to all things. It typically applies to … You clearly say, this is a way that I want to express myself. Whether it’s through writing something or creating something. Like Courtland said, I don’t think that there was an option where we didn’t go and do something that in a sense scared us. It was like, do we want to do it with Indie Hackers? Is this the best platform? And ultimately I think, obviously the answer ended up being yes, which I want to now leverage the fact that you just wrote a book called The SaaS Playbook. It sounds like you heard our last episode where we talked about some of our ideas, but we have a lot of ideas. And I feel like it, we’d be remiss to not try to use you to give us a thumbs up or thumbs down on some of those ideas. Courtland, do you have that list up?
Courtland:
Well, I’m curious, off the top of your head, Rob, what would you do in our situation? What do you want to see us do if anything?
Rob Walling:
Oh, that’s so interesting. It’s interesting because MicroConf and Indie Hackers are very similar, but I’ve seen Indie Hackers as definitely more early stages maybe not, but it’s definitely folks who maybe want to work on multiple projects at once. Yeah. There’s a tie in there. I’m not sure I have an idea off the top of my head of where I think Indie Hackers should go. And there’s a big reason for that. Is while you’re a community and MicroConf’s a community, you’re different. You’re like a social news site for bootstrappers. And I’ve never run one of those. So I actually don’t know where I would take it aside from … We can come up with revenue ideas and all that stuff, but I liked your idea of the Kickstarter before. I think that’s clever. But that’s got to be on your longer term. You need a shorter term of ads and or pay gating, right?
Courtland:
Yeah. Right now it’s ads, it’s pay gating. We were thinking of almost a Indie Hackers VIP. A little bit like Amazon Prime. You’d be like, sign up for Amazon, you get Prime. And they just stuff a whole bunch of features into Prime that have nothing to do with each other. Hey, do you want to stream videos? Do you want faster delivery? None of these things are related, but the more value they put in Prime, the more of a no-brainer it is to not only sign up, but to not churn. And I think running an online community, it feels like, well, there’s lots of different things you want to do. I want to have these new cool Indie hacker profile pages that people will actually link to on their Twitter. But is anybody going to pay for that? And if they do, it’s just going to be a super low price point.
Well, if we stuff that into some sort of Indie Hackers Prime subscription, or we add a few features, gradually over time as we build more and more things just makes that more and more valuable to opt into. And there’s lots of different things we can build that are just generally helpful for the community and impactful that don’t have to on their own be this amazingly killer SaaS idea. That appeals to me a lot because I just want to build small things. I don’t want to build some gigantic hairy SaaS that’s going to take eight years.
Rob Walling:
And you have a luxury of the community trust you. You have such a strong brand that people will … If you say, “Hey, this is what we’re launching and we’re going to keep building,” it’s going to be a bunch of people like myself who are going to throw their credit card in and be like, I’m sure they’re going to deliver.
Courtland:
Right. Yeah.
Rob Walling:
So here’s Breaking news that … Producer Xander’s probably going to be mad at me for saying this, but this is already in the works for us. We have MicroConf Connect, which is a Slack channel. It has 5,100 founders and aspiring founders. We are going to be offering a premium paid version of that, which just has five or 10 perks and premier access to MicroConf videos and you get a bunch of private channels in the Slack and whatever else. There’s a whole list of it that I actually don’t remember. So if you’re asking me what you would do, that’s what I’m doing.
Courtland:
Yeah.
Channing:
Yeah. You’re like, why yes, that is a good idea, Courtland.
Courtland:
It’s a no-brainer to some degree. If you love MicroConf, you’re part of the community, you’re going to go. Why wouldn’t you pay some small amount more to get all these extra features and things that allow you to not only support the community, but also get access to more benefits.
Rob Walling:
Right. And that’s the same with Indie Hackers. And your community itself is much larger or a bit larger than ours. And I think you have … It’s a no-brainer that you could make some money there.
Channing:
A little bit easier when you can add someone as a member of your community by them clicking a few buttons on the internet than having them come all the way.
Courtland:
I’ve got some other ideas on this list. One thing that a lot of people have asked me about is this idea of … You know we have this giant directory of products on Indie Hackers, Rob?
Rob Walling:
Mm-hmm.
Courtland:
A lot of people have asked about Indie Hackers investing in other Indie Hackers. In fact, Erik Torenberg DM’d me. Three months ago, he started On Deck, which is this … I don’t know how to explain. A school for people in the tech industry to help each other with these different topics. And he’s like, hey, why isn’t there a way for people who love these small Indie projects to basically support each other financially and invest in each other? I’m not sure how it would work, but why haven’t you figured that out? And it’s been in the back of my mind for a long time, but I haven’t just sat down and thought, how would that work?
And Rob, you’re the best person to talk to me about this because you actually invest in “bootstrapped” startups. You see what are the returns like? How does it actually work? And I think no one’s really cracks this. Not because generally speaking, people invest in tech companies hoping for a unicorn. And the average Indie Hacker is not trying to make a unicorn. They’re trying to pay their rent. And so something that I’m noodling on is there some way to financially … Because partly it’s just fun. If I could go to a giant directory of Indie Hackers and see all my favorite people building their stuff, and I could throw money at them to help them be able to take off work and launch earlier, et cetera, and expect not some huge return, but something that makes it somewhat worthwhile, that would be dope. I’m not sure what the numbers are like for that though. Realistically, is that even possible to get a return?
Rob Walling:
Yeah. That’s the complex … So there’s two complexities that I’m going to introduce. I love this idea as well because I would love to go to a directory of Indie Hacker Projects or MicroConf project and just be like a hundred bucks, 500 bucks, whatever. This is great. This is super fun. I think there’s two things that are going to get in your way or going to make it complicated. Number one, return drivers. Making your money back will be very, very difficult. Even if you go across all these Indie Hacker projects … As you said, people are trying to make their rent. Maybe they get to 20K or 30K. The money that’s thrown off from there just isn’t a lot. So the valuations would to be very … I’ll say they’d have to be very reasonable compared. It’s like if you raise at a million dollar valuation and you put in a $1,000, you own 1/1000 of that company.
And so as you throw dividends off … We can do quick math is nothing. So you can’t raise at a million. So you got to raise at maybe a hundred thousand valuation. And will people allow that? Will they say, “I’ll sell 20% of my Indie Hacker project for 20 grand.”? So that’s one thing. To make the economics work it will have to be different than … Certainly than Silicon Valley, but even then, the TinySeeds and the Indie VCs, you would be at I would say, a level lower just in valuations in order to make the economics ever work.
The other thing is on the … My God, the laws in this country. The securities laws. We spend so much money on lawyers, and we are literally lobbying Congress to try to get the 99 investor rule changed. We’ve raised a fund. We can only have 99 investors. They all have to be accredited. They’re already accredited. These are millionaires. And yet I can’t have more than 99 people in that fund. It’s ridiculous, right?
Courtland:
Yeah.
Rob Walling:
We’re working with a group to try to get that changed. But all that said, in your case with Indie Hackers, I think you’d want to go more the red CF. The crowdfunding route, right? Because then you can just put in a few hundred bucks. Because if you were to try to raise from accredited investors, A, there’s just only so many, and B, if you raise a thousand dollars from an accredited investor, the legal fees alone to just put that together are cost prohibitive. So I think with crowdfunding, I would then logistically want to go out to one of the crowdfunding platforms and partner with them.
Almost like you’d have a crowdfunding syndicate. Like a syndicate is, you go on AngelList and we run this, We get a SaaS deal, and they’re outside of TinySeed, but they’re in the TinySeed syndicate. And we can raise 100 grand, 200, 300 grand to help them raise a round from our investors. Now in a syndicate, they all have to be accredited. And I don’t know that that’s the best idea. I don’t know that’s the best option for Indie Hackers. But I’ve never seen a crowdfunding syndicate and I don’t know if that could exist. Because you don’t want to deal with the legal, trust me. It is mind-boggling. It’s expensive and time-consuming. Talk about stuff we don’t want to deal with. It’s the worst. It’s like-
Channing:
Yeah. It just seems like crowdfunding sidesteps so many of those issues. You get to invest. Let’s say you get to … Let’s call it invest, but you’re not necessarily only just buying equity. You allow for say, the founder of a company to innovate what they want to give people such that maybe there are way easier returns. Like, hey, if you invest this much money … They can do the tiers. Then you can be someone who has access to these features for my product. We’ll always have you on this page. Who knows, right? But it just allows-
Courtland:
Some benefit that’s not equity.
Channing:
Right. It just allows for some innovation on the kinds of returns. And we talk about markets and the personalities that go into markets. Well, it just so happens that if this happens on Indie Hackers, you’re dealing with people on the supply and the demand side who have a lot of initiative, have a lot of creativity, and have a lot of goodwill with one another. So that’s something that I’m … It’s a really fascinating idea.
Rob Walling:
If you remove equity, it becomes a lot simpler.
Channing:
Exactly. Exactly.
Rob Walling:
And if you go to the more … You talked about doing a crowdfunding model that isn’t equity. More of a Kickstarter model built into Indie Hackers, right?
Channing:
Yeah.
Rob Walling:
That’s where you get back to, I could see people needing … It would be a brand. The most famous Indie Hackers who … Like John Yong Fu. He’s big on the side. And I actually don’t … Is Pieter Levels a big Indie-
Courtland:
Yeah. Pieter’s on there.
Rob Walling:
So if they came on and we’re raising, a bunch of us would throw in money. I think people who have done less work and who have less of a following might struggle a bit more but that would be the game, right?
Courtland:
Yeah. That’s the game. Can you discover the diamonds in the rough? Can you be there when no one else is? Anyway, Rob, thanks a ton. I appreciate your ideas and your feedback.
Rob Walling:
Absolutely, sir.
Courtland:
I feel like we can work together in ways that we haven’t been able to in the past, which is cool. We’re just in a whole different playing field now and so excited to go to MicroConf next year. Excited to stay in touch. Excited to talk to you about being an investor because I think I might be an investor going forward. Stripe just did their tender offer and so my money is no longer just all on paper which is cool.
Rob Walling:
I was going to say. Yeah. Now you’re rolling. That’s great.
Courtland:
Yeah. Yeah. So life’s exciting. I’m excited for your new book. I ordered, I think the option on Kickstarter to give me two hardcover copies so I can give one away. And then I think the audiobook or the ebook. And then I’ll probably buy whichever one I didn’t get afterwards because I want every format possible.
Rob Walling:
All the formats. Yeah.
Courtland:
What’s your-
Channing:
And you know how I can tell that we’re beyond the Stripe tinder offer?
Courtland:
What?
Channing:
For once you’re not wearing your robe. You’re wearing an actual shirt.
Courtland:
I can afford clothes.
Channing:
It’s either the money or you just have a lot of respect for Rob because you really dressed up.
Courtland:
He just need to see my [inaudible 01:08:00].
Channing:
You have a whole T-shirt on.
Rob Walling:
Got dressed up.
Courtland:
I subjected Wes to my robe book the other day.
Rob Walling:
Epic.
Courtland:
So Rob, you get to see me fully clothed.
Rob Walling:
Appreciate it.
Courtland:
Thanks a ton for coming on, dude. What’s your parting advice for people listening who are trying to figure out what to do now that they’ve hit product market fit? This is where your head’s at nowadays. Besides just buying your book, which of course they should go out and do, what’s something you want founders to take away from your learnings?
Rob Walling:
I think founders should … There’s so many, right? But man, one thing I really regret is I didn’t delegate more.
Courtland:
Oh yeah.
Rob Walling:
That I didn’t hire more senior people. I hired a lot of junior people because I didn’t have money and I was always the bottleneck. Managing junior people. And I think one thing that’s on my mind these days is the luxury that I have, we talked about earlier of being able to work on what I want is because we have very senior people. And so the moment you can, hire someone who’s really good, even if they’re expensive, and that will allow you to 10X your business.
Courtland:
Love it. Feels amazing hiring somebody who’s good and then suddenly all this stuff is getting done and it’s getting done better than you would’ve done it and you’re just like-
Rob Walling:
It is. Crazy.
Courtland:
Yeah. It’s nice.
Channing:
It’s really a matter of inertia too. I say that to go from zero to one as a founder, you have to learn how to wear all the hats. But to go from one to two, you have to learn how to take them off. And it’s really a question of habit. But that’s awesome advice. Where can people go to find more about you?
Rob Walling:
Startups For The Rest of Us if they want to listen to podcasts or Twitter, @RobWalling.
Channing:
Boom.
Courtland:
Startups For The Rest of Us, highly recommend it. One of the longest running podcasts in the space. Super good. Rob’s silky voice coming through every episode. Like what you heard here.
Channing:
This is a three host episode.
Rob Walling:
It really is. Well, and people listening to this on my feed, Startups For The Rest of Us, should go check out indiehackers.com. These gentlemen need some more signups so they can get some ad revenue.
Courtland:
Survive.
Rob Walling:
And of course, the Indie Hackers podcast, which I’m glad you’re back because there were a few months there that were touch and go.
Courtland:
Glad to be back.
Rob Walling:
And I was like, what’s happening? They need to keep producing this.
Courtland:
All right. Thanks Rob.
Rob Walling:
Absolutely. Great to be here. Thanks so much to Courtland and Channing for joining me this week. You can find them on Twitter at CS Allen and Channing Allen. That’s A-L-L-EN. As well as obviously @IndieHackers. It’s always great to have them on the show. The conversation flows very naturally. So I hope you enjoyed this episode. This is Rob Walling signing off from episode 659.