Lessons Learned from a Lifetime of Bootstrapping with Rob Walling of Drip and TinySeed

Courtland Allen 7s

What’s up, everyone? This is Courtland from IndieHackers.com and you’re listening to the Indie Hackers Podcast. On this show I talk to the founders of profitable internet businesses and I try to get a sense of what it’s like to be in their shoes.

How did they get to where they are today? How do they make decisions, both in their companies and in their personal lives and what exactly makes their businesses tick? And the goal here, as always, is so that the rest of us can learn from their examples and go on to build our own successful businesses.

Today I am excited to be talking to the one and only Rob Walling. I think the best way to describe Rob is that he’s really the entrepreneurs’ entrepreneur. He’s bought companies and grown them, he’s started companies from scratch. He has bootstrapped companies from nothing to profitability and millions of dollars in revenue. Somehow during all this, he found the time to write Start Small, Stay Small which is the book for developers looking to create their own profitable internet businesses.

He is the co-host for the podcast, Startups for the Rest of Us, which if you haven’t listened to, I highly recommend. He co-created MicroConf, the world’s biggest conference for self-funded software companies, which I was lucky enough to speak at this past year. Today he is working on a new project which a lot of people are talking about called TinySeed, the first start up accelerator designed for bootstrappers.

Rob, welcome to the Indie Hackers podcast. You are just everywhere, man, and I really appreciate you taking the time to come on.

Rob Walling 1m 16s

It’s my pleasure. That was a heck of an intro. You nailed it.

Courtland Allen 1m 19s

Well, you have done a heck of a lot of things.

Rob Walling 1m 20s

(Laughs.) It’s been a long list. I think that starts implying at a certain point that you are just getting old, so.

Courtland Allen 1m 28s

(Laughs.) Yeah, I was tempted instead of doing that whole intro to just introduce you as the grandfather of bootstrapping. But I didn’t want to date you.

Rob Walling 1m 34s

Appreciate that, man. I have been doing this for a while. I started trying to launch stuff around 18 years ago and really had my first success maybe 13 years ago. If that gives people an idea of time frame.

Courtland Allen 1m 47s

What made you decide to first become an entrepreneur? Take us back 18 years ago.

Rob Walling 1m 52s

I graduated from college about 20 years ago in ’98 and I really didn’t want to work for other people. I wanted the freedom to be able to make things. When I was a kid, say 8 years old, I learned to program on my little Apple 2E that my parents got me.

I loved the freedom and the power. I was 8. I felt God-like power to be able to write a text-based game with code that actually worked, and that people could play. Ever since then, that’s all I wanted to do is make stuff. I wrote booklets, non-fiction booklets in high school and I sold them through classified ads, just because I wanted to create something and have it justify my time with a little bit of income.

When I graduated from college, I worked construction for a couple of years. Which was hard, but a good learning experience to know what hard work is really like, to be out in the field. I started programming professionally, took a salary job and then contracting.

I realized it was super fun and I was creative for a while but then building things for other people got old for me. I started looking around to see what could I do that would allow me to have total control of my time? Should I write a book that can sell a bazillon copies? Should I buy real estate and create passive income? I literally was just looking for ways to own my own time.

After a couple of years of flailing around a little bit, including, I owned several properties in L.A. at the time and I was trying to turn that into a passive income stream. That’s a heck of a lot of work. It’s a lot of work to get that going.

I finally realized, I have this skill that so few other people have, why don’t I double down on that? It was writing code at the time, but I slowly learned to market and such over the years and that was really the goal, to own -- to just not to have to work for other people. To create what I wanted to create when I wanted to do it.

Courtland Allen 3m 57s

Your goal here was to find freedom to live your life the way you wanted. Did you know what you would do once you found that freedom?

Rob Walling 4m 6s

I didn’t. I figured that I would just create more things. The nice part of that is I didn’t know what happen but at that time I didn’t have kids. I now have three kids. Once I had one child I realized, “Oh, I would totally hang out with my kid more if I wasn’t doing this commute in Los Angeles, if I wasn’t working 40-50 hour weeks, coding for this credit card company and that is what I realized would probably fill in some of the time.

Then I would just work less, I would read more, I would write. I started blogging in 2005 and I was publishing two big, long blog posts a week. It was literally nights, weekends. I used to go out into my car. This is what a loser I am. I used to go into my car at lunch, when everyone else was eating, and I would scarf down my lunch and I would try to hammer out a blog post or an essay.

Courtland Allen 4m 56s

Wow.

Rob Walling 4m 57s

I was that determined to make this work. I didn’t know what the blog would get me in the end but looking back it was the seed that then became the podcast and MicroConf and all these other things. To answer your question, I didn’t know what I would do at the time, but I knew that I had plenty of things that I could do at the time.

Courtland Allen 5m 17s

People have a lot of trouble managing this transition between working a full-time job and eventually working full-time at their own company. For many people it can take years to make that switch. A lot of people never successfully do it. How did you manage to juggle those two facets of your life?

Rob Walling 5m 33s

I think anyone who is able to do this really quickly and easily, I think they either got lucky or they are a much smarter person than I am. For me, I dabbled in it from 2000-2005 where I would launch these little efforts and they would get a little traction, make 100 bucks a month and then it was so much work and I just knew it wasn’t going to grow.

I couldn’t spend six months of my nights and weekends, and nothing would happen. It wasn’t until 2005 I had this first break-through. I had a software business that wound up making about $2,000 to $3,000 a month, which was a house payment plus a car payment. It was pretty cool. Nothing compared to what I made as a programmer in L.A., but it was nice. It took me until December of 2008, so that’s really four years it took me.

I made the transition slowly and I did it by building small utilities and tools or by acquiring them. That was an interesting realization for me. By that time, I started consulting and contracting. I was billing about $125 an hour, writing code 40 hours a week. I didn’t ever want to carve out time to sit and spend 100 hours coding a little tool.

I started noticing that people were selling these little businesses that weren’t doing much in terms of making revenue, but I could apply my tool set that I had learned on this first product. All I learned was a little bit of SEO and a little bit of AdWords. I just started applying that to the next thing. Then I learned a little bit of display advertising.

Then I learned a little bit of retargeting and a little bit of copywriting. Each skill that I learned and put in my tool belt, I could apply to all the products I was working on at the time. I took a little unusual approach to it, honestly, in that I had almost a portfolio of these little products and even, there was an e-book that I purchased from someone, all the rights to it.

There was an e-commerce site. There were like six or eight things that all wound up generating about 10K, maybe 12K a month. That was when I was able to feel okay to quit. I had a wife and a child and a mortgage, so I was able to feel okay about pulling consulting out altogether. Which, as I said, was late 2008, maybe January 2009.

Courtland Allen 7m 52s

That story is fascinating for so many reasons. The first thing that sticks out is most developers who I talk to will say, yeah, they really want to start a business and achieve some measure of financial freedom but really what’s driving them is they want to code something from scratch on their own. It takes a tremendous amount of discipline to say, “No, I’m going to buy somebody else’s business, somebody else’s website and not build it from scratch and just work on that existing thing.” What motivated you to take that approach and how did you even learn that was possible?

Rob Walling 8m 20s

That’s a really good question and I’ve been asked this a lot. I think there were two things that allowed me to do it because I’m as picky about my code as anyone listening to this. I think I’m the best developer and that everyone else’s code sucks and no matter what code base I get into, they always did it wrong and I would do it differently.

I totally get that. It’s not that I’m not as picky as anyone else. But there were two things that allowed me and my mindset to do it. One was, I really did want the freedom. At a certain point I said, “What will it take to do that? Is there a way to shortcut this?” The answer to that was, don’t build it, buy it. As I said, I was making quite a bit of money as a developer.

Frankly, more money than – I grew up solidly working class. Dad was an electrician, my mom was a homemaker. We were fine but I didn’t have money as a kid. So when I had $10,000 - $15,000 in the bank after coding for x amount of months, that was a – I ‘d never seen that much money. To be able to take that and basically skip ahead. Instead of saying I need to launch five things – I’d already launched five things. None of them had worked.

Could I just buy one that is kind of working and make it work more and skip all the trial and error? That was part of the mindset. The first one I bought was called Dot Net Invoice. I was a dot net developer at the time. It was still in alpha. It was really early stage. The code – I took ownership of the code base and I felt okay that I hadn’t built it from scratch.

In fact, they’d done a bunch of really good plumbing code that kept me from having to rewrite a log-in screen and rewrite a forgot your password. They had taken care of all that. They had built a simple invoicing system that I could then build on. It excited me that I didn’t have to build all that. I wound up – I approached them and found – to your question of how did I figure out this was possible?

It was pure dumb luck. It was that whole thing, it’s that luck surface area, this idea of you do a bunch of things, and eventually your surface area gets so big that something hits it. I was on a forum called SitePoint. SitePoint forums, I believe, are still around but later became Flippa.

I was on SitePoint forums and it was the marketing and entrepreneurship forum and there were these two developers that said, “We’ve built this product, but we don’t know how to market it. We’d love to partner with someone who knows how to market.” I emailed and started talking with them and it was like, “You know, I really don’t want to partner, but would you just sell the whole thing to me? Because then I can take it and run with it.” And they agreed.

They said it was about 400 hours of work, of dev hours. Of course, stupidly, because I had no idea what I was doing, I did the math in my head And I said, 400 hours times my hourly rate is like $50 grand, maybe it was 40, $40 or $50 grand. I forget what I was billing at the exact moment. But I said, “Boy, if I can get this thing for even 10 grand, that’s a bargain. This thing’s worth a lot.”

Which it wasn’t because it wasn’t generating any revenue. (Laughs.) It’s not what we know today. This is 13 years ago. To be fair, it was generating $200-$300 a month. They had a month that was $800. Turns out there was a launch they did. Turns out it was a little bit shifty. But I bought it for that or – may have been $11,000. I think they countered.

I bought the thing and instantly, the price was $99 bucks, I tripled it to $300. It never sold that many copies. It made 2 grand, 3 grand a month so you figure it sold 7-10 copies. That was game changing for me. That’s when I knew, A, this is possible. I can actually make money on the internet.

I was coding 40 hours a week at a job and then I was coding 20-30 hours a week, nights and weekends. And I loved it. As much as I loved hanging out with my wife, when she left town I would just rachet that up. I’d do 30 plus hours a week, nights and weekends, and make some progress on it.

Courtland Allen 12m 14s

It strikes me as, when you’re talking about this, the thing that you have the most of when you have a job is money. You’re actually getting a salary. It’s coming in on a regular basis. The thing you have the least of is time. You’re spending 40 hours a week in this job.

What most people do when they’re trying to make this transition is find little stretches of time, like you said, go out to the car and eat your lunch and then find some time to blog. Work nights and weekends.

But the approach that you ended up taking was to take the thing – the resource you had a lot of, which was money, from your job and use that to save time. It’s really smart that you did it that way. I, even today, don’t see very many people buying businesses and building them up.

Rob Walling 12m 49s

Yeah, that’s really good insight. That’s a good way to put it. That is exactly how I thought of it, too. I remember at a certain point telling my wife, right now I have more money than time for the first time ever in my life. Because all the way through college and early married life you’re trying to save for a house and this stuff.

But when money started piling up in the bank, it’s a good problem to have but the bad problem that I had is I didn’t want to work for anyone else. So how can I take that? I’m not going to save a million bucks or two million and retire right now but how can I take that and leverage it. That’s exactly the calculus I did in my head. I did it multiple times. There were multiple things I acquired.

Courtland Allen 13m 24s

Do you have any salient memories of major failures or mistakes or things you did wrong when you were first starting out buying these companies and trying to grow them?

Rob Walling 13m 33s

I remember the realization after I bought Dot Net Invoice and gave the guys the money, took the code base, got the website and I emailed their existing customers and I said, “Hey, I’ve acquired this, and this is a good product, blah, blah, blah.” I thought the product was fully baked and it was not. I got 30, maybe 40 just pissed off replies. People saying, “Those guys weren’t maintaining it. There are bugs in it. We’ve reported all these bugs. No one’s doing anything.” I thought, holy shit. I just spent $10,000 on a lemon.

That’s more money than I’ve spent on anything. I’ve never spent that much on a car. I was like, “This is catastrophic.” I remember, the hair stands up on the back of your neck. You think, “I can’t believe I just made the worst mistake of my professional life.” I was reading through the emails and at a certain point I realized, “I can fix this. I’m a developer. These are bugs. These are pissed off people. I can make them not pissed off.”

So, one by one I would respond and say, “What’s your bug?” Well, this doesn’t do that and – so Cool. I’d spend two hours here and I would fix that thing. I spent 60 hours in the first two weeks just triaging angry customers and people who were trying it and they had errors and fixing little things.

The nice part about it, though, it was obviously super stressful. But there was an interesting thing, where – the fact that I had written that $11,000 check, my back was to the wall. I couldn’t justify walking away from the product. I feel like sometimes people launch a product, it doesn’t get traction, it gets hard and they walk away from it. This was actually motivation that I had to make it work. I was all in because I had written that check.

Courtland Allen 15m 21s

What an amazing way to build good will with these early customers. The juxtaposition between these earlier owners who weren’t responsive to customer complaints and feedback and then you, this new guy, who is taking it over, who immediately starts fixing bugs one by one. I bet they were pretty happy.

Rob Walling 15m 36s

It definitely got me some goodwill with them. Then I was able to get annual upgrades. It was a one-time sale, but I was able to get annual upgrades and when I increased the price and the annual upgrade price went up, I really didn’t get many complaints. It was worthwhile, not only for that but also for the learning experience for me.

I had never answered support emails. This is coming straight into my Gmail. I’m just sitting there, one by one answering them. Eventually realizing, this really is how you should talk to customers even when they’re angry. It’s stuff we all know today but it’s like, there were no blogs or podcasts talking about this.

There was no Indie Hackers. I was just making it up as I went along. Holding my feet to the fire was a helpful learning experience that I took forward with me to every other product I did. That’s the thing. It’s like, “Respond, don’t panic, get in there, elbow grease. Do what it takes to get this done and it will yield some results.”

It went from making $200 or $300 a month and it consistently made $2,000-$3,000 a month for years and years until I took on a business partner because I wanted to move on to other stuff. Eventually I just gave it to him when it – it was a small thing at a certain point, and it wasn’t worth my attention anymore.

Courtland Allen 16m 51s

So one of the more interesting projects, businesses you moved onto was a company called HitTail. What’s the story there?

Rob Walling 16m 58s

What was interesting is, around 2009, when I stopped consulting, I had this period of immense creativity. I acquired HitTail two years later, in 2011. There was this two-year span where I wrote my book, Start Small, Stay Small, that you mentioned. I launched, what I believe is the first ever online training for bootstrapped software founders.

It was called the Micropreneur Academy. Now it’s called Founder Café. It was a membership site with a bunch of content, everything I had learned from doing what I had done. We launched MicroConf and we launched Startups for the Rest of Us. All four of those things happened within 18 months. When you asked earlier, “Did you know what you were going to do with your time once you had it?”

I didn’t, but that’s what I wound up doing, was just pouring out information. I blogged more and the podcast went weekly and the conference and everything. I did that. Our son was born in 2010, our second son. I spent about 8 months with him. I was working about 10-15 hours a week and he and I hung out. I walked around the town with him, he was in Baby Bjorn strapped to my chest and I loved it, man.

Some of the fondest memories of my life are of that stretch of time. As it eeked into 2011, I was getting bored. I was just restless to do the next thing. I realized that I could build something from scratch, and I entertained that idea. But I came back to the, “What if I could acquire a SaaS app and basically do a Warren Buffet play.

Buy something that is valued at less than I think it’s worth and then grow it?” I had all these skills by that time, and I had an audience. I had so much more. I had stair-stepped my way up to where I felt confident enough that I could do some damage in a good way, really grow something.

HitTail was app I found that was neglected. It had been built by a PR firm in, I believe it was 2006. I found it by going back and googling, I think your listeners might dig this, but I went back and googled top ten start up launches or top one hundred start ups of 2006, top one hundred start ups of 2007. I would just go to the list. Anything that wasn’t B2B SaaS I just ditched.

But anything that was, I would then go and see, are they still around? Does it look decrepit and ancient and neglected? Even if it wasn’t, I would still just say, “Are people using it? Do I think this is making money?” I would cold email the founder or sometimes even just the contact form.

That’s how I found it. I sent out probably 50 emails, between 50 and 100 and got some responses and some not. HitTail resulted from that. HitTail is still around. I sold it in 2015. As Drip was scaling up, I just didn’t have the time anymore to maintain it. It is a long-tail SEO keyword tool.

Courtland Allen 20m 6s

At some point during all of this, you mentioned, you decided to sit down and write a book before acquiring HitTail but after your previous successes. The book was called Start Small, Stay Small and it was a step-by-step guide to teach developers how to launch a self-funded startup. What made you decide to write something like that?

Rob Walling 20m 25s

I was blogging since 2005 and so about five years into the blog and a few months, I believe into the podcast, which we started in 2010, I had this massive list of questions that people would send me about starting up.

I wrote about the HitTail acquisition – I’m sorry, not the HitTail one, I wrote about both of them but the Dot Net Invoice one is called, if you google, “The Inside Story of a Small Software Acquisition”. I have a three-part series where I went into as much detail as I could. I’m not sure if I mentioned dollar amounts, but I really went line by line.

I got tons of questions about all of this stuff. I also started using virtual assistants in 2007 when I read The 4-Hour Work Week, and I realized I was doing all my own support on all these products. I had no idea this whole world of virtual assistants, remote work existed. I was looking at hiring someone in L.A. and they were going to charge 40 bucks an hour.

I was thinking to myself, I can’t even make this work financially. I can’t get these products off the ground. But as soon as I found out about VAs I had a whole team, I had seven or eight VAs doing all different types of stuff, design work and support and SEO, just helping me. I would start blogging about that. Pretty soon I realized, “Wow, I actually do have some knowledge.”

I still had imposter syndrome, but I definitely thought, I know at least more than the person who is starting today. So, I took all those questions and I took a bunch of ideas that I hadn’t yet blogged about and I said, “I’m going to go out on a limb, and I’m going to write a book. I’m going to see if this even makes sense. I’m going to self-publish it.”

Because that’s what we do as bootstrappers. I don’t want to wait. I actually talked to a couple of publishers who had approached me on the blog, and they said it took 18 months from the first conversation to the time it was published.

And I don’t have that attention span. I need stuff to happen faster. That was really the reason I didn’t do that. It wasn’t even about the money because I didn’t think I would sell that many copies if I self-published, but it was something I wanted to build quick and I wanted to ship, and I wanted to see what the response was.

Instead of writing an entire book I put up a landing page. In true, smoke-test format I put up a landing page and I still have a screenshot of it somewhere if you want me to send that to you for whatever reason.

The headline said, “At Last a Book Built for Founders Who Want to Build a Product Without 6 Million Dollars in Venture Funding,” or something like that. It was kind of a snarky headline. Then it had a couple bullets of this is who I am, and this is what I’m doing. If you are interested, enter your email.

That was it. Which, of course, went into MailChimp. I blogged about it, I put it on Hacker News. It went to the front page. I got around 600 emails that said they were interested. To me, that was validation. I figured if I could sell even 200 copies at $30 a piece that would be 6 grand and I could justify sitting down and spending a couple months to write the book.

Which shows you what I thought my time was worth back then. (Laughs.) So, I sat down and wrote it, on and off took two or three months. I repurposed, actually I had some content in the Micropreneur Academy that fit really well that I repurposed. So, it wasn’t totally writing from scratch.

Then I launched it to the list, and I sold 300 copies in the first month which netted me about – well netted, it was gross, about 9 grand. I was like, that was so cool.

Courtland Allen 23m 52s

That’s great.

Rob Walling 23m 52s

I’m so glad I did that. And then next month it sold 300 more copies and the month after it sold 400 copies. It was crazy. It resonated with people enough that it just kept going. It has sold about 11,000 or 12,000 copies now. I think I’ve made about a quarter million dollars on it.

You can tell my aspirations were definitely not that. But it was a game changer. When it went on Amazon it got – it was part of the recommended books if you read The Lean Startup for a while. There were all these serendipitous things that would happen. Again, it is – the harder I work, the luckier I get. I’m not sure if you’ve heard that. It’s an old quote, but.

Courtland Allen 24m 30s

Yeah, it makes perfect sense.

Rob Walling 24m 31s

That’s how I feel, sometimes.

Courtland Allen 24m 33s

It’s funny, because your book is still relevant today. There was a post on the Indie Hackers forum, I think last week, where somebody was asking about advice from the book and then you ended up jumping in. Would you ever write another book yourself? Related to that, what’s your advice for other entrepreneurs who are considering writing a book today?

Rob Walling 24m 50s

I would write another book myself. Every year I consider it. Typically, every December I think, do I want to write another book next year? Or do I want to update Start Small, Stay Small, which is more likely what it’s going to be because I get that question a lot and it is fair. I feel like 80% of Start Small, Stay Small is mindset and high-level stuff that that is timeless and then there’s 20% of it that’s prescriptive.

That stuff went out of business 18 months after it was published. But the answer is, yes. I would love to write another book. I enjoy that creative process. Are you asking me if software founders are thinking about writing a book or just someone in general?

Courtland Allen 25m 27s

Yeah, maybe someone listening to the podcast who is thinking, “Maybe I want to start a company. Maybe I want to write a book.” They are both valid ways of generating income online.

Rob Walling 25m 35s

Yeah, that makes sense. My advice would be, I didn’t launch it with no audience. The reason it worked for me is that I had spent – this was five years after I was – I had 300 plus essays on my blog when I published the book. I had 25,000 RSS subscribers.

I had however many – I didn’t have very many email people yet because I was just six months into building email lists. I’d just discovered them. That would honestly – if you’re going to do the info product route or book route, I lean much more towards figuring out how to make a publisher work with that or building some kind of an audience so you just have someone to talk to about it and a built-in sales channel.

There are obviously alternatives. If you’re going to write a book about how to program for kids, if you created some killer visuals and had credibility you could go to Kickstarter or Indiegogo with that. I don’t think that’s a bad way to go. I know I back way too many Kickstarters and I would totally back that. Anything that teaches my kids how to do technology or nerdy stuff like that, I’m all over it.

I think less so if you’re going to start a software product or a software company, I don’t think you need to build an audience. It’s good to have one and it’s always treated me well, but I’ve seen many, many more people launch products without much of an audience and still do okay as long as they really serve that need and they do have some type of a good marketing channel.

Courtland Allen 27m 4s

Let’s fast forward back to HitTail. You’ve written this book, you’ve acquired a ton of experience, you’ve written tons of blog posts, built an audience. What is some of the advice you gave in the book, Start Small, Stay Small, that you found yourself taking when you were working on HitTail?

Rob Walling 27m 12s

That’s a good question. One of the things I did really early on is I went through and did a complete rehab. You know when they buy the houses and they rehab them and flip them?

Courtland Allen 27m 25s

Yeah.

Rob Walling 27m 25s

I bought it and rehabbed it and didn’t flip it. I guess I sold it four or five years later. I went through a complete conversion and funnel analysis. Like, this first page doesn’t get people to the next page, doesn’t get people to sign up. The sign-up flow is too cumbersome. There was just all this of CRO it’s called conversion rate optimization.

And that I talk about – I didn’t call it CRO in the book because I’d never heard that term. I talk about how to get people to your call to action and to have calls to action. I also applied SEO stuff I talked about in there, the keyword research, in terms of, it had all these incoming links. A PR firm had built it.

It had these amazing links from the New York Times, Wall Street Journal, Inc. Magazine.

All these places that I would have a hard time getting links from, high authority, but no one had ever done any SEO on it. So just looking at title tags and restructuring the site made it start rising in the ranks. Pricing was all wonk. It was way out of whack. It was 10 bucks a month and then there was some huge plan that only a couple of people were on and it was $100 a month.

That was it. There were no plans in between those. So, instantly change that to have pricing based on the value people were getting, not just some random, no one had ever tested pricing. And using virtual assistants. I got in there for about a month and did support for a month or two on HitTail. As I started growing it and figure out what questions were coming in and then I had one of my virtual assistants handle support to free me up time to get her done.

Courtland Allen 29m 5s

One of my big heroes is Ben Franklin and he has this quote, I think I’ve talked about it on the podcast before. It’s, “Experience keeps a dear school, but a fool will learn in no other.” What he means by that is, well, yes, it’s great to learn from making your own mistakes because those learnings will stick with you.

It’s better to learn from other people’s mistakes because you don’t have to make those mistakes yourself. It’s better to read Start Small, Stay Small and learn vicariously through Rob Walling than it is to spend 10 years making all those same mistakes. Rob, what are some of the mistakes you’ve made and learned from versus things you’ve learned from other people?

Rob Walling 29m 39s

That list is endless, but I think most things that I learned, it was from one or the other. I learned SEO, it’s a lot harder to do today but there was just more opportunity 2005-2012. I learned that by both. I learned it by being in the MOZ forums and there was SEObook.com, Aaron Wall.

He would be an SEO mentor of me, and Rand Fishkin would be an SEO mentor even though – I know Rand today, but I didn’t know him then. I would take tidbits, then it would be experience because A, I had to prove that it worked and B, I had to get the experience of doing it. So, there was a lot of stuff like that from both sides.

I’m trying to think of a mistake that I made. The mistake I made buying Dot Net Invoice for more than it was worth. That wasn’t great and I later learned how to value software products. I’m trying to think of a specific example because I have people I respect in the startup space.

There’s Jason Cohen. I had to have learn loads from that guy because he’s just so smart and every time he talks, I feel like I walk away with something that’s going to help keep me from making a mistake. I feel Dharmesh Shah is similar. He’s just a godfather of SaaS in my opinion. Those guys, Dharmesh talked about churn.

As I was doing HitTail it was the second SaaS that I’d done but this was the first that was at this scale. I took a bunch of stuff from a talk that Dharmesh did at Business as Software, about churn and thinking about it and trying to predict it and I implemented that. I don’t know if it kept me from making mistakes, but it certainly helped me grow HitTail to what it was.

Courtland Allen 31m 28s

You end up accumulating all this knowledge over the years and you end up with this curse of knowledge situation where you forget what you used to not know. It meshes together. You know all these things and it’s hard to track exactly where you learned something or when you learned something.

Rob Walling 31m 41s

That’s absolutely true, yep.

Courtland Allen 31m 43s

While you were working on HitTail you eventually started another business called Drip, which ended up being, I think financially, your biggest, most successful business that you started in your entire career. Where did the idea for Drip come from and why did you decide to start another company while you were running HitTail?

Rob Walling 31m 59s

That latter question of, why did I do both, is a good one, because I would not recommend that to most people. To that point I had started something or acquired it and then I built it up and then I put it on autopilot, and I moved on to the next thing. That works with really small things in really small niches where you can just kind of own they SEO keyword tools and Google wasn’t changing very frequently back then.

But it gets harder when you have something larger like a HitTail which was doing mid-six figures. There were a couple of things. Google started doing Panda and Penguin, those were updates to their SEO algorithms, and then they switched to not provided. I don’t know if you remember this, but you used to be able to go into Google Webmaster tools and you saw all the keywords that people were finding your keywords for and you would see which ones were converting for you.

It was this amazing knowledge that was so helpful. Then you could double down on trying to either buy ads or do SEO for those keywords. When they turned to this not provided thing, they did stop providing them. It kind of decimated HitTail temporarily until I rewrote this big piece of it to scrape this other thing. I rescued it from the ashes, but it was my biggest income source at the time.

It was me and a couple contractors working on that. And I looked around and said to myself, “How long is this going to last? Is this a decade or two-decade business or is Google going to crush it accidentally at some point and I’m going to have nothing else to go to?” That was one part of it.

I also didn’t love – it was $10 a month starting. $10, $20, $40, $80 were the price plans. $10 a month apps have high churn. Eventually they get hard to grow. You just have to have a really wide funnel. Certainly, it was making good money, but I also wanted to do – what’s it like to run a seven-figure business? There was that whole thought process.

The good news about HitTail, though, I sold it and it is still going strong. Google has not decimated it. In fact, they released an API that made HitTail way more stable. It very well could be a decade or two-decade app at this point. That led to me thinking is there something else out there that is a higher price point, hopefully has lower churn, isn’t built on someone else’s platform.

I didn’t really want Google or Facebook or Twitter to be able to crush it. It would be another SaaS app. I thought acquiring another one and eventually just decided, let’s build something. The Drip started off – eventually became an email service provider that competes with the likes of MailChimp or AWeber.

Then it eventually became my marketing automation provider with a lot of automations. But when it first started all it was, was a little email capture widget, little JavaScript widget and then it was autoresponders. This was at a time before SumoMe or OptinMonster or whoever else you think of when you think of the JavaScript pop ups that capture email.

We needed that on HitTail. I had a contractor named Derrick who I hired to build that out. It took him a week. He used a bunch of jQuery and hacked a bunch of stuff together and wired it into MailChimp. I was like, “This took way, way, too long. That is not a hard thing to do. Why isn’t this productized somewhere/?” So that is where the idea came from.

Courtland Allen 35m 26s

It strikes me that this experience you had of building HitTail on top of another product, Google, and then having the deer in the headlights moment where you think your entire company might crumble because Google made some small change, is a great example of something that you learn through your own experience.

I’m sure people have written about this, the risk of building on someone else’s platform but you go into the next business and that’s one of the items on your checklist. Don’t build something that’s completely dependent on someone else’s business. I’ve watched you give a talk. It was years and years ago and you touched on this topic of solving your own problem.

It’s the oldest advice out there. If you want to build a company, you should solve a problem that you yourself have so you know what it’s like to be in your customer’s shoes. The problem is that’s not enough. That doesn’t always work by itself. You need to validate your idea as well. How did you validate your idea for Drip besides knowing that it’s a product you, yourself needed for HitTail?

Rob Walling 36m 18s

I’m glad that you pointed out that doesn’t always work, because it doesn’t. Scratching your own itch only works if a bunch of people have the same itch. I knew that by this point. I was far enough in. It was probably October, November of 2012. I realized we’d built this thing and I talked to Derrick, this contract developer, and said, “Hey, do you think we could turn this into a little SaaS app?”

He knew Ruby and he was like, “Yeah, that would be interesting.” I said, “All right, don’t write a line of code. I’m going to talk to people I know,” specifically within SaaS because I knew founders from there. It was working on HitTail so that was where I was going to start with it.

I always knew or figured it would move out into other bloggers information products or whatever, which it did. I had a conversation with 17 different founders that I knew. I just emailed them, and I said, “Here’s what I’ve built, it’s going to do this, what do you think?”

If we built this thing and made it a service, a SaaS app, would you pay 99 bucks a month for it? Here’s the value it would provide.” I got 10 or 11 to say, “Yeah, that makes sense. It seems like it’s providing enough value.” Because on HitTail we were getting a bunch of traffic but anyone who didn’t sign up for trial they were just bailing.

They had no email list. Once we added this widget to it, we were collecting – I forget what the number was, it was like 1,000 emails a month or something. It was a huge amount. Huge, relative, right? Going from 0 to 6,000 in six months. It upped our visitor to trial conversion rate went up 33% once we implemented this.

To me, I was like, these results are insane. Again, insane is all relative but it was pretty nice. It was a lot more money to the bottom line for no ongoing work. I got the verbal that folks were willing to try it out and felt like it provided that value. So, in December of 2012 Derrick broke ground with code on it and essentially, at that point, in my head I had $1100 of MRR in presales.

Although, in the end, by the time we built it I had done a bunch more research talking to people and I had lowered the price to $49 as the starter. Of the 11 I think about 6 or 7 wound up actually purchasing it. So, the numbers didn’t work out exactly as I would have expected but it certainly was a good exercise to have these conversations. I don’t think any of those were telephone or video conversations. I believe they were all via email, which shows you there are different ways to do it.

Courtland Allen 38m 58s

I remember you showing the email off during your talk at a MicroConf and it was this ginmongus email you sent to people, paragraph after paragraph explaining what you were working on and somehow they read through this thing and helped you out.

Rob Walling 39m 12s

I shortened that later. It was pretty gnarly, yeah.

Courtland Allen 39m 14s

I think it’s cool because at that point you’d already built a huge audience for yourself through blogging, through MicroConf, through your book. I wonder how advantageous it was for you to take advantage of your network. How do you take advantage of your network and how did that help you build Drip?

Rob Walling 39m 29s

In all honesty it was the first time I had utilized my network in the entire time I was doing anything. I had utilized my audience. I had a blog audience I would mention HitTail to or the podcast. That got a few customers. It really didn’t make that big of a difference.

I had never gone to my network. I was never thinking of it like that. I think as an introverted developer, I know people. I run a conference. I invite really fancy speakers like Jason Cohen and Hiten Shah and all these people to come speak, but I don’t really have a network. Literally, this was my mindset. So, to reach out to folks who would respond to my email, to Ruben from BidSketch, Ruben Gomez, to Wade Foster from Zapier, to Jeff Epstein from Ambassador, these were three people I emailed as part of that Drip thing and of course they’re going to respond to my email because they know who I am.

There was an advantage, a unique advantage I had at that point because if I was cold emailing those folks, it would have been a much different story. That was the first time I reaped what I had been sowing in terms of becoming more prominent, having a personal brand. And that’s where I’ll get the question sometimes, “Is it worth building a personal brand?” Well, it depends.

Are you doing it for the audience? Are you doing it for the network? Are you doing it for both? What are you going to launch? You have to think longer term about it, but yes, at that one moment it was key that I had that personal brand.

With Tiny Seed, we will probably talk about it later, but that’s been a big thing as well. If I wasn’t who I am and people didn’t know me, I would definitely have a much harder time getting that off the ground as well.

Courtland Allen 41m 11s

I want to dial things back a little bit. At this point you have worked on 10, 15 businesses. I know in the short-term your goal is to grow this pre-sale revenue you’re collecting but what were your long-term goals at this point and how were those shaped by the fact that you’d found so much success with your previous businesses?

Rob Walling 41m 30s

My goals were bigger – each business I wanted to make it 5x bigger, 10x bigger than the previous one. I’m not sure that was necessarily healthy nor helpful, but I definitely wanted this to be at least a seven-figure business and I didn’t want to do the same thing again.

Growing another SaaS business to 30, 40K a month, as weird as this sounds for it to come out of my mouth, just sounded boring. That’s the thing, ten years ago, I wouldn’t have said that. That was a goal of “Oh my – are you kidding me? I can own or run or operate a SaaS business that’s doing that and see what it’s like on the inside and be part of it and all that?” But I was just done and needed that next challenge.

I think that’s the curse of – well, one of the blessings and the curse of being a founder who wants to continue innovating is that novelty is part of what keeps us interested. So, the creativity in the creation of that next business is something that I wanted out of Drip.

Courtland Allen 42m 38s

How do these loftier ambitions affect your decision-making? What did you do differently to ensure that Drip wouldn’t be something that stagnates at 40-50K a year but could get to 10 times that?

Rob Walling 42m 52s

The price point was one. The early marketing was another. We took six months before we got to an Alpha and all during that time I started talking about Drip and building an email list. We did a slow launch from about July or August until about November, where I would email groups, because it was 3400 people on this list.

I didn’t want to just email 3400 people and just say, “Come in the doors.” A, you’re just going to bleed people out because you don’t have the right features, can’t support all that many people trialing. There’s a problem with doing that. So, I started emailing them in 300 person groups, I believe.

Every week or two we would email another 300. That lasted through November, and that was when we officially opened the doors and people could get in. I spent a lot of that time being very cautious and careful about, I want to retain as many people as possible and really want to build it as something that can, like you said, can 10x from here.

So, I want to make sure all the marketing I do is worthwhile. I also ran ads to build the email list which was something I had never done. I’d run ads before but never to build an email list. That was a thing where I wanted to get off to a really good start at the beginning so that I could ramp this thing up pretty fast.

Frankly, when we launched, by the time we hit the end of November, December we were at about 8K, 7 or 8K MRR and I thought that was a pretty good start but I wanted to take it up and I thought it had a lot of potential to do something beyond that.

Courtland Allen I know the story of Drip and I know that once you hit that point where you were doing about $8,000 in monthly recurring revenue things stagnated there and you found it hard to grow. Why was that?

Rob Walling 44m 35s

Because we didn’t have product/market fit. We hadn’t built something that people really, really wanted. Although there were users using it, I was driving trials because this time I had the marketing engine going. Trials would come in and they would stay for a month or two and they’d churn out.

Some of the biggest reasons were “Well, I can kind of cobble this together with MailChimp plus some JavaScript.” Or, “You’ve built something, but it feels like it’s too expensive for what it does.”

I got a lot of feedback like that. That was a big take-away for me to make a decision. Because, one way you could look at the too expensive comment is to lower your pricing. But the way I looked at it is, I call it aspirational pricing, which is, I aspire to build an app that the minimum price point is 49 bucks, so what would I need to build to make it worth that?

I started asking that of people who canceled. It flips the question on its head. Rather than “Why did you cancel?” Oh, because it’s too expensive? Well, what would it need to do that? And some people started saying, “I already use MailChimp so if you built broadcasts and a couple other things,” but then – MailChimp is cheaper, it’s 15 bucks or whatever – it’s free and then has a low plan.

They said, “There’s this automation thing that’s coming around where you can – Infusionsoft does this and a couple other tools where you can click on a link in an email and it will do things. It will move someone from one campaign to another” Basic email automation. I was like, “What? I’ve never even heard of this. This is crazy.”

It’s the end of 2013. I’d never heard marketing automation or any of that stuff. That’s when I realized there was this movement in more advanced marketers away from these standard ESPs, MailChimp and AWeber are still wildly successful businesses and I have respect for them, but there was this movement towards having a more automated approach where you can do things in emails.

So we started looking at that and I realized, “This might be an avenue, might be a path to get us to some product market fit where not only have we built something people want but no one else has built this yet, at this price point in a package that’s this easy to use.”

Because it existed but it was all upmarket. Infusionsoft, HubSpot, Marketo, Eloqua, Pardot and even Ontraport. If you’ve never heard of those tools, don’t worry. Those start at $300 a month and they go up to 5 grand a month. Or they go up to way more than that but starting price is like $300 to a few grand. To build it in a $49 package, a stripped-down version of it. It was a light version, but it was built with modern software UX and sensibilities, it was easy to onboard, it was self-service, it was all the things that we like as founders and SaaS founders. That was the path that we eventually chose to go down.

Courtland Allen 47m 25s

A lot of people start companies and run into some wall where it’s hard to grow. They stagnate and they really haven’t reached product/market fit. By this point in your career you’d started tons of companies.

Did you have a playbook for how to get beyond this point? How did you know that talking to customers and doing the research that you did would lead you to the promised land?

Rob Walling 47m 45s

Oh, my gosh. It was agonizing, man. It was six months of waking up in the night and I would hear my inner voice say, “You should know how to do this.” I would literally hear, “How is it that – you’ve written a book on stuff. You should know how to do this.”

Talk about imposter syndrome creeping up. We’re not growing and what are we going to do to fix it? I had kind of a playbook. I knew I had to find something. I knew we weren’t working. I knew we weren’t going to grow. I was looking for how to either how to pivot or add the features. I don't know if it was exactly a pivot as much as a maturing of the product that we did.

I knew of Customer Development from Steve Blank. And Lean Startup was coming around at that point, but that wouldn’t have helped me as much as Customer Development was the big conversation in my head I was thinking about. Have your customers tell you stuff. There’s also danger in that because there were customers that were telling us to do stuff that were bad ideas.

I had to filter those out. That’s where the – there’s no playbook but there are some guidelines. We have all these requests and I could’ve followed one. We would get requested, “Hey build landing pages into Drip.” “Hey, build ecommerce, build a shopping cart into Drip.” “Build affiliate management.” Just all this stuff. We could’ve gone down that road, but it didn’t feel right to me with the vision of the product.

I think that’s where a founder has to go with their gut and build something people will want and then validate it a long the way. It took us five months to build all the automation but two months in, we dropped the first one.

Then we dropped another one every two weeks. As that happened, churn went down, trials went up, all the metrics started going in the right direction and I realized, “We’re going in the right direction. Let’s keep doing this.”

Courtland Allen 49m 44s

It’s a lot of pressure, Rob, to not only have a company that’s not working as it should but to feel like you should know how to do this because you’re the guy, you wrote the book. How could you possibly not know?

Rob Walling 49m 54s

It wasn’t fun times, for sure.

Courtland Allen 49m 57s

You’re, with this episode, part of the first husband and wife team to come on to the Indie Hackers podcast because your wife, Dr. Sherry Walling came onto the show earlier this year and we talked a lot about founder psychology and trauma and getting through – what you’re talking about right now, getting through the dark times. Were there any other dark times you had to go through and what’s your take on how to push through those as a founder?

Rob Walling 50m 18s

There were other dark times. There was a period where I burned out on Drip, where I was trying to grow it and I was just doing too much. I was making the founder mistake of, “I can handle everything. I’ll handle all the fires and all the hard decisions.” That was in 2015.

I had some burn out. That was tough. In me, burn out looks like depression a little bit, where I just lose motivation. And frankly, the acquisition, I don’t want to steal your punch line if we’re leading to there but ultimately, we were acquired by Leadpages.

That acquisition was super stressful for me. It was like four months, five months of really tough times. Advice is tough to give in these spots, but I’ve definitely learned to hold things looser and be less concerned about all the details. And to not to try to keep it to myself. I wasn’t talking to Sherry about nearly enough of these things as I should have. Which is funny, considering she’s a psychologist.

Courtland Allen 51m 13s

This is her job.

Rob Walling 51m 15s

She could’ve helped me. For some reason I bottled a bunch of it up. I stressed about things a lot more than they needed to be, in all honesty. Now that I’m going through this again, starting this new thing, we’re going through some of the same things that stressed me out last time.

The startup phase, there’s chaos in a new entity. But I’m like, this isn’t nearly as stressful as last time. I don’t think it’s because I’ve done it before, I think it’s because I’m having that mindset of, “This is all going to work out.” I think that’s a big thing to believe, not be stupid, to believe everything will always work out. But to know that just because you had a hard conversation with a customer or an employee or with a prospect today, it doesn’t mean that the whole business isn’t worthwhile.

Which is sometimes the narrative that I do, and other founders tell themselves. Do less of that and figure out how to look long-term and be like, “In a year this will all be figured out and it’s going to work. How do we get from here to there?” Rather than worrying about the things that are happening today.

Courtland Allen 52m 15s

Sage advice, but easier said than done as well.

Rob Walling 52m 18s

Indeed.

Courtland Allen 52m 19s

We could probably talk about Drip for hours, but you’ve talked about Drip on many different podcasts, many different talks you’ve given. So, people who are interested in how you navigated Drip into the major company and success that it became, I encourage you guys to go look at some of Rob’s other stuff online.

The ultimate end of the story, which you gave away, was Drip was acquired by Leadpages for an undisclosed sum. I think it’s safe to say you’re one of the few people I’ve had on this show where you would never have to work again if you didn’t want to. And here you are today starting a new company called TinySeed. What’s keeping it going? What is TinySeed and why are you excited to be working on it?

Rob Walling 52m 54s

It’s funny after the acquisition I worked for Leadpages, the acquirer, for about 18 or 20 months. Then I took about 4 months off and during that time there was an idea that had been percolating with me. I looked back in a notebook from 2011-2012 and I had written this idea and it said, “YC for bootstrappers.”

What I meant by that was, why isn’t there an accelerator like Y Combinator for people who would otherwise bootstrap their company. Where the end goal is not Demo Day Series A, here’s enough funding to get to the point where you’re sustainable. Then you can raise a round if you want to. Maybe you don’t want to.

Maybe you want to live off dividends, maybe you want to sell it eventually. There are all these options. But let’s preserve optionality without having to have unicorns, to have these billion-dollar companies. What I’ve done and people who I hang around with, they’re starting SaaS companies, typically B2B that get to say 1 to 20-30 million in revenue, and they are super fun, they’re lucrative. It’s a real viable market but you can’t raise funding.

Or it’s very, very hard to raise funding. You can’t raise traditional venture funding to do a business that’s that “small”. But it doesn’t feel small to me. So that was the idea when I wrote it down. As I did my MicroConf talk in April, someone approached me, and it wound up being my co-founder with TinySeed.

I had known him for several MicroConfs, and he does some stuff in the finance space. One of the reasons I didn’t do the YC for bootstrappers back in 2011-2012 is I didn’t really think I had the network and I didn’t want to deal with the legal and the fundraising and all the stuff it takes to do that. To do an accelerator you have to raise a small fund to then hand out money to the people and run it and there’s just a bunch of stuff to do.

That part didn’t sound like fun. But all the other stuff did. So, when approached me, his name is Einar Vollset. When he approached me, he said, “Hey, I really liked that idea you talked about of smaller companies raising smaller rounds but not from institutions, like you should raise a fund and I can help you do that.” I was like, “That’s really interesting.”

Because I know this guy is smart and connected and I trust his judgment. He said, “Yeah, we should do an accelerator.” We started noodling on that and that became what TinySeed is today. It’s basically the first startup accelerator designed for folks who would otherwise bootstrap. But the goal is not the Series A, it’s to get to a point of sustainability.

And whether sustainability means, “Hey, I decided that we are going to get bigger and raise another round,” the option is there. Or it’s “Hey, I just want to build a little one, five, ten-million-dollar business and pull dividends out.” The investors, being TinySeed, would get some and the founders get others. That would be the goal.

We announced a couple months ago and have been working hard on it. I think the other thing, the differentiator is, a lot of my folks, like my MicroConf people and a lot of the founders I speak with, they can’t move, aren’t able to move to San Francisco or Boston or another location for three months and hammer away on things.

They have a family or a kid or they’re in a situation there where they can’t move. Ours is one of the few virtual, remote accelerators and it’s a year long. The idea of the year is, it takes a long time to grow SaaS apps. It’s not the traditional, the venture funded model is, “Let’s throw a bunch of money at it and try to compress time.”

Try to make the time shorter so you grow super-fast. And with Facebook and Instagram and even maybe Google and Twitter, that works. But none of those are subscription SaaS apps and SaaS apps take forever. Almost no matter what you do, it’s going to take a long time.

At a certain point you can add stuff and it goes faster and such, but especially in these early days, like an accelerator would be time, in my opinion is even more important than money. That’s why we’re – we’ve thought it through from all the angles. I hope so, anyways.

Courtland Allen 57m 11s

Well, this is huge, and I think it’s badly needed. You mentioned this question you had back in 2011-2012 when you came up with this idea, which is, “Why isn’t there a YC for bootstrap companies?” What’s the answer to that question? What’s hard about this and why hasn’t anyone done this before?

Rob Walling 57m 27s

There’s definitely some challenges to it. One is that there aren’t a lot of funding sources that understand this. Meaning, when you raise a venture fund you go to these family offices and these wealthy individuals and endowments for universities and non-profits. You convince them to give you a small amount of money or often it’s a large amount of money and then you invest it in startups.

There’s a whole way you go about that. 90% of them are going to fail. One of them is a Dropbox or an Uber and it returns the fund. That’s how everyone thinks about it. What we’re proposing is not that. As we’ve said, we can come up with a model that is successful for these smaller businesses, 1 to 20-30 million. Convincing investors who have traditionally thought the venture capital approach forever, that this is viable, is a task.

That’s what we’ve been doing. We’ve been educating and then finding folks who are into that approach. So that’s one side of it. On the other side of it, on the founder or company side, it’s really only been the last four or five years that this community has become what it is. There’s Indie Hackers and there’s MicroConf, and there is Hacker News and there are a lot of bootstrapping podcasts.

A lot of these weren’t around even four or five years ago. Without some kind of ecosystem and some type of community, it’s really hard to get a fund like this off the ground. You need both. It’s a two-sided marketplace if you think about it. You need the investors to put the money in, which is an education thing that we’re working on. Then on the other side you do need companies that are even open to, or interested in, and you need to be able to talk to them, which is what we’re doing through MicroConf and our podcast.

Courtland Allen 59m 25s

In a lot of ways we’re living in the Golden Age of the slow growth, self-funded startup. TinySeed is really a bet that we’re not at the peak yet. This is a trend that’s just getting started.

It’s going to continue and explode into the future. What are some of the indicators, what is some of the evidence that you’re looking at to tell you that’s what’s happening? Why is today a better time to build one of these companies than at any time in the past?

Rob Walling 59m 51s

I think there is so much more opportunity and it’s untapped. So many great founders, they think that VC funding is the only way to go. So, they go, and they do the pitches and they do the accelerators. I’m not anti-VC funding. I never have been. I’m just anti- everyone thinking that’s the only way to start a business.

That’s in the first page of my book that I wrote in 2010. There are so many other options. You can bootstrap. You can go VC funding. Then there is this in-between that you can now – even without TinySeed, I’ve done six angel investments in the past three years that are all essentially this model. It’s B2B SaaS. One is called CartHook run by Jordan Gall, who has spoken at MicroConf and such. Folks may have heard of him. He has a bootstrap web podcast.

Churn Busters is another one, LeadFuze. These are B2B SaaS apps that when we talked, at the time they were like, “I don’t think we’re ever going to raise institutional money. We just want to get to millions in revenue so that everyone is successful.” That was the whole idea of it. That didn’t exist – I’d never heard of anyone doing that before Customer.io did it back in 2012, 2013, when they raised their – they call if fundstrapping.

Fund Strapping. They raised this round and they said, “We’re going to raise a quarter million bucks, it’s just to get escape velocity and then we hope to just be profitable.” And it’s becoming more common. Like I said, 2014, 2015 I really started talking about it on the podcast, realizing, there’s this third option that I think is totally viable and I wish I had done.

I wish that it hadn’t taken me 7, 8, 9 years to get the point where I could start Drip. The only reason I could start Drip is because I had all these apps throwing cash off. I funded it myself, but boy, if I could have done that 5 years earlier, my life would be a heck of a lot better.

That’s why I think – I totally agree with you that this Golden Age there’s so much opportunity and there’s so many untapped places because everyone’s been focusing on these billion dollar opportunities, whereas how many people do you and I know who have these amazing $5 million SaaS apps that throw off 50% net margins and they had no chance to raise funding from anyone, ever.

That’s where I think we are pouring gas on a fire that has started burning on its own and I just want to keep riding that.

Courtland Allen 1h 2m 16s

One of the cool things about TinySeed is it’s not just, here you go, here’s some money. Good luck building your company. It’s an accelerator. Like you said, you’re going to be providing one year of mentorship and guidance to these companies to help them succeed, which makes it super valuable.

You’ve obviously got a ton of startup experience over the past 15 years. What advice would you give to people listening to the show right now who are in the beginning stages of trying to decide whether or not to start a company and what kind of company they should start?

Rob Walling 1h 2m 44s

Know that it’s going to be harder than you think and start small. That’s what I would encourage. And you don’t have to stay small, like my book says. But I started really small. I started with an app that did 24 grand. And 24-30 grand a year, that’s not a very big app but it taught me so much. And then I stairs-stepped up to the next thing, to the next thing, to the next thing.

If I had tried to start Drip as my first app, I think we would’ve crashed and burned. I don’t think I had the skill, the experience, the confidence, certainly not the funds, to be able to do something like that. That would be my advice. Know it’s going to be harder than you think. Start smaller. Don’t look at someone like Jason Cohen – whoever your startup idol is, don’t look at what they’re doing now and try to do that because they’re at such a different place than you are. I really believe in this whole idea of starting small and building your skill set as you go.

Courtland Allen 1h 3m 39s

That’s great advice and I think it’s so deceptive, too, because some of the people that a lot of us look up to as having built these amazing things really, what they did, was started small. Even Drip itself, which is your biggest start up to date, started as a tiny little widget. Thanks a ton, Rob, for coming on the show.

It’s been really helpful to hear your story, to hear about TinySeed and what you’re working on today. Can you tell listeners where they can go to learn more about what you’re doing, whether they might want to apply themselves and where they can find more about you and what they’re doing online?

Rob Walling 1h 4m 8s

Absolutely. It’s my pleasure to come on. I appreciate you inviting me. So TInySeed.com is where the info is, all the info about TinySeed. And if you’re curious about what I’m up to because I talk about this stuff every week on my podcast and I write about it and I do all the things. But it’s just my name, RobWalling.com is my hub for all the activities that I’m doing.

Courtland Allen 1h 4m 30s

How would you describe your podcast, by the way? I think people should really listen to it and since this is an audience that listens to podcasts, I think it might be a good place to plug Startups for the Rest of Us. How is it different than the Indie Hackers podcast?

Rob Walling 1h 4m 40s

I appreciate that. It’s not an interview show. That’s probably the biggest difference. My co-host, Mike Taber, and I started it, two software entrepreneurs and we just started talking about what we were up to and our thoughts and recommendations and learnings. It’s 420 episodes now. It’s been going for eight years.

There’s a lot there. It’s typically just two people sharing their thoughts, insights and answering a lot of listener questions. We do interviews every couple of months, maybe, but it’s much more a day-to-day me talking. I talked all the way through the story of Drip, what I was up to and the challenges. Now I’m talking about how I’m launching TinySeed.

Courtland Allen 1h 5m 22s

It’s good stuff. It’s one of my favorite podcasts and I recommend people listening in to Indie Hackers right now to go give that show a listen as well. Anyway, thanks again, Rob, for coming on the show.

Rob Walling 1h 5m 32s

Absolutely. Thanks for having me on.

Courtland Allen 1h 5m 39s

: If you enjoyed listening to this conversation and you want a really easy way to support the podcast, why don’t you head over to iTunes and leave us a quick rating or even a review.

If you’re looking for an easy way to get there, just go to IndieHackers.com/review and that should open up iTunes on your computer. I read pretty much all the reviews that you guys leave over there, and it really helps other people to discover the show, so your support is very much appreciated.

In addition, if you are running your own internet business or if that’s something you hope to do someday, you should join me and whole bunch of other founders on the IndieHackers.com website. It’s a great place to get feedback on pretty much any problem or question that you might have while running your business.

If you listen to this show, you know that I am huge proponent of getting help from other founders rather than trying to build your business all by yourself. So, you’ll see me on the forum for sure as well as more than a handful of some of the guests that I’ve had on the podcast.

If you are looking for inspiration, we’ve also got a huge directory full of hundreds of products built by other Indie Hackers, every one of which includes revenue numbers and some of the behind the scenes strategies for how they grew their products from nothing. As always, thanks so much for listening and I’ll see you next time.