Episode 782 | Why I Succeeded: My 10 Best Entrepreneurial Decisions

Rob Walling:
I never bet the house. I didn’t rack up credit card debt. I didn’t gamble on my mortgage, but as my confidence, my experience and my savings grew. I started making bigger bets with my time, with my money, and with my energy. And when those bets paid off, they created leverage that helped me stair-step my way into the life that I wanted. It’s another episode of Startup For the Rest Of Us. I’m Rob Walling, and in this episode I talk about why I succeeded my 10 best entrepreneurial decisions. This episode is the counter episode, if that’s a term I can coin to last week. It’s a continuation of sorts. In last week’s episode, I talked about my biggest regrets, my biggest mistakes. And as I put that episode together, I realized, and yet I still succeeded. So why is that? And I started thinking, well, it’s because I made these other decisions that even in spite of the regrets and the mistakes, I still made it. 

I still achieved what I wanted to achieve. And of course, I’m still achieving things today. I have new goals, but realistically, most of the goals for my life growing up were to be an entrepreneur and to have enough money that I could work on whatever I wanted to work on when I wanted to work on it. Having achieved that now 10 years ago or so, I enjoyed reflecting on both things I did well and the things I did not do so well. But this episode should be more upbeat than last week’s because it’s about success. It’s about things that I did Right. Before I dive in to these 10 takeaways I want to tell you about MicroConf Connect. It’s our online community for ambitious SaaS founders. If you haven’t checked it out, we have monthly live events. We have an online forum and discussion groups. 

I do a live q and a where you can ask me questions in here, my responses in real time, but once a quarter. And we have hundreds of founders that are in the group, and it is better than any paid community out there. And the reason is because people pay for it. And so there is a minimum bar of the quality of the members of the community. You can add to MicroConf connect.com if you are looking for an online community of support and encouragement and a place to offer insights and help you discuss stuff in a controlled environment. We have a full-time moderator who makes sure everything stays nice and tidy, and the conversations stay amazing. MicroConf connect.com. And with that, let’s dive in to my first best entrepreneurial decision. Number one is I stopped reading and I started shipping. So around thousand one or 2002, maybe 2003, nah, 2002, I think I stopped hiding behind business books and the excuse of learning, and I started writing code and launching products. 

It’s easy to hide behind the excuse of, I just don’t know enough yet. I’m waiting for someone to give me permission. I’m waiting to figure out what the secret is that’s going to guarantee me success. I have that secret. You know what it is? Nothing’s going to guarantee you success. No one can guarantee you success. You have to start shipping at a certain point. For me, I remember it being really scary, shipping things onto the public internet. What if someone got mad? What if someone criticized me? But realistically, I did it anyways, and shipping things publicly helped me push past my analysis paralysis, and it helped me start to build confidence. None of those early projects did much. You can refer back to last episode to hear how I just flailed for years of launching a bunch of stuff to see what sticks, and it was a big waste of time. 

But these were critical first steps to get me over that terror of firsts, the terror of doing something for the first time, launching code onto the public internet, launching a blog post, which I’ll talk about soon, launching a podcast, being on camera, all these things that really terrify you and doing things in public creates opportunity. I say that a lot. Doing things in public can create opportunity for you. And this was my start of doing things in public where I say I stopped reading and started chipping, and that’s not totally accurate. I kept reading. I just reduced the reliance on constantly needing to have the next book and the next book and the next book, and I reduced it dramatically, and I started chipping instead. It was a great first step that without it, I would not have succeeded. Decision number two is I learned from mistakes and I changed course. 

I see founders out there who have the blind spot of they don’t learn from their mistakes or they don’t change course. You can’t just try the same thing over and over and over. I didn’t try the same thing over and over. At first I did because I was like, well, it’ll work eventually. But I started realizing I need to make real adjustments to this. So early on, I had several sites that were ad-based that were like venture backed type startups, but I was bootstrapping. I made B2C software. You wonder why I say don’t do it. I’ve been there. I’ve done the things I tell you not to do. And I realized, well, I can’t just do that again. It didn’t just fail because it was going to fail. It failed because the economics of B2C businesses, especially SaaS, are not good. So I moved from B2C to B2B. 

I had a little super low price products early on, high churn, catastrophic unit economics because you can’t afford to pay anything to acquire customers. So I moved from lower priced to higher priced products. I moved from building everything from scratch to acquiring small apps with some traction. I learned from mistakes that I made and I changed course, and I evolved my strategy based on experience instead of blindly repeating past efforts. So I took the learnings from the last mistake that I made and I fixed it, and I didn’t know if I was going to fix it, but I just changed course and tried it, and that time it worked. So this was definitely one of the good decisions that I made. And this wasn’t just back in the early days. This still happens today as we are launching new marketing efforts or audience building efforts with MicroConf and TinySeed. 

Frankly, anything we do, we often launch it and we are directionally correct, but it is not a hundred percent there. It’s 50% there, and it’s kind of working, and we have to not try the same thing over and over. We have to make real adjustments course correct and learn what we did wrong and make it better. The third decision I made is I worked really hard to build a cushion for myself so that I could take early risks. So while I was working a full-time day job, I started freelancing on the side as a developer, and I slowly raised my rates until at some point I could quit my day job. So by 2005, I was charging around a hundred dollars an hour, maybe 1 25. And this isn’t $2,005. That’s significantly more. I dunno if that’s 1 75 or 200 these days, but I was working remotely before remote work was mainstream, and that allowed me to do it nights and weekends while I had the day job, which really none of the other developers that I was working with, I think there were probably 20 developers at the company, the credit card company when I left, I don’t think any of the other ones were moonlighting that way. 

And I did it so that I could build up that cushion first. I saved 10,000 bucks over the course of several months and nights and weekends. I was tired all the time. It really was kind of all I did was work, but I wanted to build that cushion so that I could afford to at some point, either take time off, quit the day job. Turns out I used it to buy my first software product, but if I hadn’t put in the work and done the savings, I wouldn’t have had that ability. I saved pretty aggressively. So first it was 10 K and then 20 K and eventually had 30 K, which is when I bought tail in 2011. But it gave us Sherry and I, the financial cushion where I could take bigger entrepreneurial risks and have my back a little bit to the wall, but not so much to the wall that we would say lose the house. 

And that cushion was something that in retrospect was a really good decision because it allowed me to take bets that were big enough that they made a difference in our lives if they succeeded. Decision number four is probably a controversial one for me to say, but I’m going to say it and then I’m going to say, this might not be for you. Number four is I started writing about what I was doing. So this is when I started blogging. Originally, I was going to journal for myself. It helped me clarify my thoughts, helped me reflect on decisions, kind of track my progress. It was a form of almost self-guided mentorship where it gave me structure and insights into what otherwise just felt completely chaotic. But I was trying to track progress. But as I watched Joel Spolsky publish essays, Paul Graham publish essays, I thought to myself, doing things in public creates opportunity. 

I don’t think I actually thought that to myself. I didn’t coin that till a decade later, but that’s what I was doing. That instinct was to put my thoughts out into the world. And this might be controversial because don’t I say don’t build an audience. I do. And if you’re going to start a SaaS company, I don’t think you should build an audience. 95 plus percent of the SaaS companies that I’ve invested in had no social media audience, no personal brand audience. When they launch, they still don’t. And they’re still wildly successful. And there’s dozens of seven and eight figure SaaS companies in TinySeed. But why is this on my list then? Well, because for me, my path, while it obviously was to start software companies, then start SaaS, when SaaS became a thing, it then led me to writing books. Being a blogger, podcaster, YouTube, or however you want to describe me, this is my higher calling. 

I really, really enjoy what I’m doing today and what I’m doing today. I don’t want to say it wouldn’t be possible, but it certainly started with this writing that I was doing. It started with the blogging. And so for my personal journey to find what I call living my best life, the best job I’ve ever had, which is being a podcaster, YouTuber, TinySeed writing books, I love it. In order to get here. I believe that this writing and blogging and publishing really kicked that off. Putting my writing online also in the early days, brought me into the orbit of people that I admired. Like Joel Spolsky noticed me, Jason Cohen bought my first book. I was blogging before Jason Cohen and Patrick McKenzie and Pelley from Balsamic. But as they came online and all the bloggers, we all, we knew of each other if we didn’t know each other. 

But I started respecting Jason Cohen’s blog. I think he started blogging maybe oh eight or oh nine. And then when I published Art, small State, small, he bought a copy. Patrick McKenzie started blogging, I think it was oh seven, and I started in oh five. But I was a fan of Patrick. We were kind of doing the same thing. We were kind of doing small software products. I say we were doing small software products, so we had some overlap. And he was in Japan, and I was here, but the first MicroConf 2011, Patrick McKenzie flew over and spoke, and then DY from Balsamic. Same thing. It’s like it put me in this network. If anything, it was like having the audience. I don’t serve me much in the future years of building SaaS specifically. It does serve me well now. But having the network of Jason Cohen, Patrick McKenzie, PEL, and whoever else I rubbed elbows with was more important. 

Build your network, not your audience. Publishing online, it helped me build credibility. I formed good relationships, and it really helped me discover opportunities that I probably couldn’t have predicted. One of those, and kind of a subset of this point is later I wrote a book. I wrote Start Small, stay Small, because I had a bunch of content on the blog. And then I started a membership website in 2009, which is like a precursor to MicroConf actually. And I decided to write the book, start Small, stay small. It was a huge time investment, but the potential upside I thought was significant, right? And it did put me on the map with a lot of people. It got me some speaking gigs. I spoke in the early days, I think it was in 2010 and 2011 alongside Eric Reese as the Lean Startup was coming up. And then years later, Eric was really generous in supporting TinySeed and when we first launched it and helping us meet some LPs and doing some promotion of it. 

And again, all those things. It wasn’t that Eric was in the audience, but it was that he was in my network because of these things that I had done in public. And writing a book, interestingly enough, transformed me from being just another blogger to someone who was seen as more of a leader of the bootstrapper movement. And so for me, for my journey starting to write and publish about what I was doing was definitely a life-changing decision. Decision number five was that I made increasingly larger, but still manageably sized bets. So this is a quote from Dave ett. He is the author and the creator of Sheldon and Drive, which are two of my favorite web comics, and he does Kickstarters and publishes them as books, but he is on a podcast called Comic Lab. You’ve probably heard me refer to him many times over the years. 

And he has this quote of make increasingly larger, but still manageably sized bets. And I had never heard someone put it that way before. But as I look back over my career, I did level up. And when I had a bit of success, I was willing to bet a little bit more and go a little bigger next time. I never bet the house, I didn’t rack up credit card debt. I didn’t gamble on my mortgage. But as my confidence, my experience and my savings grew. I started making bigger bets with my time, with my money, and with my energy. And when those bets paid off, they created leverage that helped me stair-step my way into the life that I wanted. This single decision might be the one that made me the most money in my career. So I bet $11,000 on dotted invoice in oh 5, 0 6, it was a tremendous bet. 

It was money I had just painstakingly worked hard to save nights and weekends. Then I bet 30,000, 35,000 maybe with legal fees on hit tail in 2011, I bet $200,000 building drip. All of those would’ve been brutal had they not worked out. But none would’ve sunk us. We wouldn’t have been bankrupt. And when I made those bets, I put my back to the wall a bit, not at risk of bankruptcy or losing the house. I did put pressure on me to succeed. See, I’m not of the personality that I could burn the boats, that I could quit the day job and watch my runway burn down. I actually don’t think that’s a good decision in most cases, especially if you’re supporting a family, unless you have a significant runway and you’ve already started building something, or you have some type of audience or some type of strong network. 

But for me, making these increasingly larger, but still manageably sized bets over the course of many, many years is really why I am where I am today. Decision number six, this was less of a decision and more of just what I did. And I said earlier that making increasingly larger, but manageably sized bets might be the number one takeaway. I take that back. I think that’s number two. I think this one is number one, I didn’t avoid hard, boring, grindy, scary work. I leaned into it. I never told myself, I’m not going to do this thing, particular marketing approach or write some code or whatever, insert whatever you don’t want to do. I’m not going to do this because I don’t feel like it. I never said that. I knew from really early on that if I was going to be successful with no network, no audience didn’t know any entrepreneurs, didn’t have any money, no investors, no clear path, that if I was going to be successful, it would require a lot of hard unglamorous work. 

And especially as I said, as an outsider with no role models and no wealthy friends. There were all kinds of things that I wasn’t passionate about. SEO kind of seem boring. Running ads kind of seem boring. Learning how to copyright that one seemed interesting. I was a writer fixing bugs, doing support launching products. I wasn’t passionate about fixing other people’s code. Tire code base is not written by me taking it over. You think I wanted to do that? Does any developer? And I didn’t just rewrite it from scratch. I didn’t. I just fixed the bugs and shipped it. It was often tedious, frustrating nights and weekends, hours of grinding. Seriously. I don’t want to overstate it, but I’m not. It was hundreds and hundreds of hours doing that I didn’t want to do, and I did it anyway. I think part of it was out of necessity because I wanted to succeed. 

Part of it was I was an athlete in high school and college, and I did a bunch of stuff that I didn’t want to do. That was really painful because the goal was to be faster than the other people. I was an athlete, a track athlete, and the goal was to run fast and beat my personal best and win. And I knew that I had to put in hard work to do that. And I worked construction after college, and that was hard work, but I needed the money. And so it just never, it did occur to me to question it. And Sherry would ask, and friends would ask, when is this going to pay off? And I was like, I think at some point it will be worth it. It was hard work, it was grinding, but I did it anyway. And I didn’t need every part of the work to be fun. 

I had hobbies for that. I still played the guitar. What I needed though was progress, and I was willing to grind to get it. So honestly, this mindset, as I said, is probably the number one thing and the number one most important reason that I feel like I achieved what I have. Number seven is I deliberately learned about myself so that I could turn my blind spots into weaknesses. So I believe that a blind spot is just a weakness that you don’t know about, and that keeps you from succeeding over and over and over and gets in your way, over and over and over. A weakness that you don’t see as a blind spot. The more you learn about yourself, how you operate, whether from self-reflection, taking personality tests. I mean, I’ve taken a dozen personality tests at this point, the Enneagram and the StrengthsFinder, and there’s a bunch of them, Myers Briggs, as well as feedback from my spouse, from colleagues, mastermind groups, co-founders that helped me turn blind spots into things that I saw. 

I still have several weaknesses, and I have worked on improving those as well. I’m more of a believer in leaning into your strengths. But I put in the work to understand myself such that I could get clarity on my weaknesses, and that allowed me to either power through them to work around them or to hire for them. At this point, I don’t think I have any major blind spots left. Now that may be hubris, but for several years now, probably a decade, I feel like pretty clear on who I am, what I’m great at, and what I’m not. And it’s because I made self-awareness a priority and learned about myself. So one of the things that I’m not sure I would’ve realized in the early days how much it would come into play in my success, but I think it’s had a tremendous impact. Number eight is I figured out what I wanted and I went for it. 

I was pretty focused. I didn’t wander aimlessly or chase trends like a lot of founders were doing and still do. I knew that I wanted to own products. I knew that I wanted to build equity in something, ownership. I wanted to stop working for other people. And it took six or seven years of focus to reach full-time product income. And then I reset my goals, more stability, more freedom, and eventually enough cash and never have to work again. And I believe I hit each of these milestones because I had clarity and referred to number six, I didn’t avoid hard, boring or scary work. I was pretty clear on my goals, and I just relentlessly executed to find them. And if you refer back to last episode, sometimes that relentless execution led to burnout and led to me not feeling super mentally healthy. So there are pros and cons to this, and I wished that I had still figured out what I wanted and went for it, but had a little more of a measured approach as I was pursuing it. 

But definitely kind of knowing what I wanted, and it wasn’t, I knew exactly how I was going to get there. At least I had these goals of like, I want to quit the day job and have product income. All I did was push everything into that bucket and basically say, everything’s going to get me to that. And from 2002 until 2008, that’s what I did. And then I wanted a bit more money in from 2008 to 2012, that’s what I did. And then I wanted to either sell for enough money that I never had to work again or make enough money off of SaaS app that I never had to work again. And that was 2012 to 2016, on and on and on. So I think knowing where you want to head, knowing where you’re going, and then working hard to get there, I think is just such a fundamental piece of that. 

Number nine is I learned when to persist, when to pivot, and when to quit. So early on in the early two thousands, I stuck with bad ideas for way too long, and I would grind for months and months without results. And then over time, I got better at reading earlier signals. So I learned how to pivot without abandoning everything. It’s not just I’m going to launch 20 things to see what works and just abandon, abandon, abandon ’em when it doesn’t work immediately. But I learned how to pivot things, how to take them and adjust, how to experiment with new angles, how to walk away when something wasn’t truly working. But I started getting a better sense of when that was, right. It’s knowing when to keep going, when to adapt, and when to shut things down. It’s a really hard skill in entrepreneurship, and one that I feel like I gained through watching people better at it than I, and through a lot of trial and error. 

But it definitely contributed to me finding the success that I wanted over the years. In fact, one example of that is I was a blogger, hundreds of hours a year. That’s a lot of time, man. I always wonder if that was worth it. But anyways, from 2005 until I think around 2011 is really when I kind of stopped publishing and I realized that blogging was a commodity. People were reading the blog among many others, kind of like a social media feed where no matter how much you try to stand out, you’re just another voice. You flip through TikTok, do you really know who’s there? Or are you just watching that TikTok? Do you know specific individual people? Or are you just kind of flipping through it like it’s content? And blogging started to become that. And so I realized I wanted to start a podcast in 2010, and that’s when I grabbed my friend and fellow blogger, Mike Tabor, and we started this very show. 

So despite having really never put audio live on the internet, not knowing how to podcast, being terrified to do it, buying a headset, microphone, recording over Skype, I don’t even remember. Pamela was the plugin. I mean, this is old school. We did it. We shipped it. And don’t go back and listen to that. It’s really bad. It’s just so funny how you can feel how nervous I am and my voice. It’s like you don’t know how to talk yet. You don’t know how to talk on a microphone. It is slightly different, not projecting, and there’s so much wrong with it. But all that said, we shipped an episode, and then we shipped an episode the week after, and then the week after. And aside from there were a couple months in there where we dropped to twice a month, I think, or every other week. 

It was only for a few months. And then we were like, nah, we’re just going to go every week. But aside from that, I basically shipped 52 episodes a year since 2010. And after a year of the podcast, I think we had about five or 600 listeners, and that was painful. I had 25,000 blog subscribers. And I remember thinking like, oh, this is brutal. But we stuck with it. And frankly, that decision and that ability to pivot, as I said, because remember 0.9, is I learned when to persist, pivot, and when to quit. I kind of pivoted blogging into podcasting, right? Or you could say, I quit blogging and started podcasting. Either way, it definitely reshaped my trajectory as a founder and as someone who ultimately wanted to write books and be on YouTube, and it helped me stand out in a noisy space. And my 10th and final decision that I believe contributed to my success is that I didn’t make impulsive decisions when things got hard. 

There were absolutely times when I wanted to rage quit, whether it was shutting down MicroConf, walking away from the podcast, or honestly leaving startups altogether at one point. There were times when I was burned out, when I was frustrated, when I was over all of it, but I never made those decisions in the heat of the moment. I gave it time. I let emotions settle, especially really fiery emotions like anger, burnout, frustration, being ragged on social media and dragged through the mud and thinking, I just want to escape and leave it all behind. And every single one of those decisions had I acted on impulse, I think I would’ve regretted. But instead, I continued to build on what I had already created from the blog to the book, to the early membership website, to MicroConf, to the podcast, to TinySeed, YouTube channel, everything else. And these days, I’ve learned that when I feel burned out or when I feel low, it’s just not reality, right? 

It’s a temporary state. Waiting six months or two months and reevaluating when I’m in a clear headspace has saved me for making so many irreversible mistakes. It’s definitely an important discipline that I’ve developed to not let temporary emotions throw me for such a loop, which is something they definitely did in my earlier days. So there you have it. Why I succeeded my 10 best entrepreneurial decisions. Some of those are more attributes than decisions or just things I did, but I enjoyed putting this list together. It made me think really deeply, not just about, oh, you could say, well, one of my decisions was starting drip. And it’s like, yeah, obviously, but that’s not helpful. That’s just a moment. It’s a momentary decision. The things I wanted to pull into this episode are around mindset. They’re around deeper thoughts, around longer term thinking, around doing the hard things that get you there. 

These are things that I think any entrepreneur, not just SaaS entrepreneurs, any entrepreneur in any space can and should apply to their own journey. And I think almost without exception, the exception might be like the starting to write about what you’re doing or write a book or whatever. But almost without exception, I think all of these will help you have an easier journey and or help you get there faster. So thanks for hanging out again with me this week on Startups For the Rest Of Us. If you keep coming back and listening, I’ll keep recording. This is Rob Walling signing off from episode 782.