Episode 781 | A Founder’s Regret List: 12 Mistakes I’ll Never Make Again

Rob Walling:
A book can help you learn more, can give you the knowledge to be more successful, but you still have to put in the work, develop your skills, and push things forward on your own, and you’re going to have to make a lot of hard decisions with incomplete information and ship, ship. Be right most of the time and get things out the door in order to be successful. At a certain point, you do have to stop reading business books and start shipping. 

Welcome back to another episode of Startups For the Rest Of Us. I’m your host, Rob Walling, and in this very personal episode, I walk through my founder regret list 12 mistakes that I will never make again. I say this is a personal episode because there are several stories that I’m going to share as I walk through this list that I don’t believe I’ve ever shared in public before, and it wasn’t out of any desire to shield these or somehow keep them hidden, just several of them hadn’t given the deep thought required to really dig in to the mistakes that I made. Over the years, over the last 20 plus years of my journey as a founder, I’ve been asked over the years what are the biggest mistakes that I’ve made as a founder, as an investor, as an entrepreneur, probably as a human. That’s a different list I’ll admit, and I always struggled to come up with a list that I felt was meaningful and genuinely things that I regretted, things that I wished I had done differently along the way. 

Sometimes I come up with one or two or three, but I sat down for an extended period of time and really thought this through and I came up with 12 mistakes that I’ll be running through in this episode. Before I dive into those, if you haven’t checked out the SaaS Institute, this is our premium coaching mentorship and mastermind community SaaS institute.com is where you can find the full info, but it’s for founders of SaaS companies doing at least a million in a RR who are looking for private coaching, private masterminding, and looking to find an incredibly ambitious community of other folks who are paying a good chunk of money to be a part of this community. The quality is extremely high, and we just started it a couple months ago, so it’s very small and very hands-on. You’re not joining a group of 50 or a hundred people. 

There are a couple handfuls of folks in the SaaS Institute and we have some amazing coaches including Jordan Gaal, Mark Thomas and Taylor Hendrickson. So if you feel like you could use someone to walk alongside you in your journey as well as be able to do a call or two with me, you should head to SaaS institute.com. In addition, if you’ve ever thought about sponsoring this podcast or any of our MicroConf events, we have in-person events, we have remote slash virtual events, you should email sponsors at MicroConf dot com and we have a rate card both for this podcast, our YouTube channel, and all of our events. We have some availability. Normally we’re booked out a quarter or two, but we do have some availability over the next few months. Sponsors at MicroConf dot com if you’re interested. And with that, let’s dive into my founder Regret List 12 mistakes I’ll never make again. 

I’ll admit I’m not nervous. That’s probably not the right phrase, but I’m a little feeling a little agitated thinking about walking through this list because there are some things in here that I really do regret and revisiting them and reliving them on this podcast is maybe not something I ever thought I would do, and I’ve done my best to keep these in chronological order, at least to the best of my memory. Number one is going to seem obvious in retrospect, I’m going to say it and I’m going to move through it quickly. So number one is believing I had to raise venture capital to start a software company. I know these days if you listen to this show, you’re like, obviously that’s not true. But in the early two thousands, I didn’t know there was another path and I was fully bought into the idea that funding and especially venture funding was a requirement to launch a software business that wasn’t true, and it delayed my path for years and years as I read all the magazines because this was really mostly before tech run, so it was reading the Fast Company and Red Herring, what that one was called. 

That’s an interesting name now that I think about Business 2.0. There were a bunch of.com magazines and it just made it seem like funding was the goal. In fact, funding was the finish line in a lot of these articles. And it’s funny, now that I’m in the know and I talk to founders, and I’m far from an insider for sure with Silicon Valley, no one knows who I am. They didn’t know when I started and they still don’t know who I am. But now that I know how these things work, and I know I’ll say the real stories of a lot of these startups, I realize that funding is far from the goal. And in fact, a lot of folks who take funding do it. They don’t know any better, not because they actually should. So that has become my mission in life, is to multiply the world’s population of independent self-sustaining startups. 

It’s through this podcast, my books, YouTube, MicroConf, TinySeed, and I’m doing that by trying to spread the word that you do not in fact need to raise venture capital, start a software company. But years and years, I wasted probably six or seven years thinking about funding and wondering how I could raise it and reading about how I could raise it and not actually acting, or I’ll say kind of half-ass acting, waiting for someone to give me permission, waiting for someone to anoint me and give me the money such that I could build a startup. And it was a huge mistake I’ll never make again. Mistake number two is launching many products hoping one would succeed Over the course of probably five years, in the early two thousands, I spent literally thousands of developer hours of my own time nights and weekends because I was working a full-time day job. 

Sherry and I were married, she was in grad school during this time, we had our first child, and during this time, I would not go out to happy hours. I mean I did sometimes, but for the most part I would say no and I would stay home and I spent thousands of hours creating products without doing any real validation because that wasn’t a thing. I didn’t even know that existed, didn’t know that you could potentially try to validate things and have conversations with customers, wait, you can do that, put up landing pages, wait, you can do that, right? This wasn’t an approach yet that people did. I didn’t know that it existed, and so I would build these products and launch one after the other hoping that one would magically luckily gain traction. I was basically throwing darts at a dartboard that might as well have been 30 meters away, and almost all those went nowhere. 

It was a huge waste of my time and effort, and it’s certainly something that these days I would do a little more validation. Even if you hear the story of Drip, how I sent out 17 emails and I got 11 yeses. If you hear the story of TinySeed, we didn’t just raise a fund, try to raise a fund and launch. I went to Twitter, went to my email list, said, Hey, we’re going to do this, and waited to see the response. That was a form of validation. I had the luxury at that point of having an audience. But if you go back to 2008 or 2009, I launched a paid membership community and I asked folks in advance of that, I had a survey on my blog, would you pay to be part of a community of bootstrapped founders and gain not only education, but gain some type of community? 

Before I launched my first book, start Small, stay Small, it had a landing page that I put up. This was me developing this approach, and I had heard of this approach from internet marketers, and then it was popularized by the success of the four Hour Workweek, but around 2004 or five six, I started reading several of the, like Dan Kennedys, and I don’t remember who else was in that space, Joe Polish, maybe there’s a bunch of names, and if I said ’em, you may or may not recognize ’em if you’re familiar with that era of internet marketing, but they talked about doing smoke tests. They talked about driving AdWords to landing pages to see how many people opted in. And that was a very interesting concept for me, and that’s why even these days, if I’m going to talk about or launch anything big, I’m going to get a landing page up, and I’m also going to try to have one-on-one conversations. 

I like to do both. Validation is never 100%, it doesn’t work all the time. It can be done poorly, it can be done, you can do validation and still have it not succeed, all these things, but it is so much better, so much better than the approach that we use to use. And I spent years of my nights and weekends, thousands of hours trying to launch a bunch of things hoping I’d get lucky and one would magically gain traction, and it’s a mistake I’ll never make again. Mistake number three is trying to bootstrap ideas that weren’t bootstrap. So at a certain point, I had a young child, my wife and I were living in, well, first it was Los Angeles and then it was New Haven, Connecticut, and then Boston, but I couldn’t move to a center where there was a bunch of venture capital and I ruled out doing Y Combinator. 

It was not the year I was in Boston. By that time, they had relocated to the Bay Area. So I effectively ruled out raising funds, and I realized I didn’t want to raise venture capital, that it wasn’t the choice for me, and I was going to grind it out and I was going to bootstrap. But the problem was is then I didn’t have a model because no one else was doing this again, this is 2004, 5, 6, 7. I mean, realistically, I started building and launching stuff in 2001, but as I really started getting some momentum and getting better at getting things live and even getting some users, there was something I launched, what was it called? It was Flo, it was feed shot.com that actually was making about a hundred, $200 a month and had several hundred users coming to submit their blog to these blog directories. 

It’s an old dated thing now, but it’s not that nothing went live and no one used it. I did use the social media of the day, or it was social news sites. Basically it was like a dig and the other, I don’t even remember what the others were. They’re all defunct now. But I did use those to drive people to check these things out. And what I learned is that all the ideas I came up with really only made sense at a massive scale. They either needed millions and venture funding, or they needed hundreds of thousands or millions of users because I was launching things with ad-based revenue models. I was launching things built for consumers, and I was copying the Silicon Valley model without the resources that they had, which inevitably led to a ton of dead ends. And I launched idea after idea that really didn’t solve a pain point for anyone, but it was, again, it’s like look at all the Silicon Valley, the new startups that come out that you hear about, and I would do a variation of that because I didn’t realize that you just can’t bootstrap that if you’re going to take a small percentage of GMV or you’re going to be ad based or you’re going to need a million users in order to be viable. 

These are just not easily bootstrap. I say in general, they aren’t bootstrap able, but I suppose one in a million, you could get lucky. And if you’re wondering, well, how do I know if an idea is bootstrap able? I could record obviously an entire podcast episode or a book chapter on that, but realistically, these days, I have my guidelines, right? It’s like solve a problem for someone and I recommend you solve a problem for businesses, but you could solve a problem for consumers as well. And that is one way to instantly at least have potential customers that have a desperate pain point that you can solve. That’s where I would start, and I didn’t start with problems with any of my old ideas. It was all about glitz and reach, and I thought to myself, would tech crunch right about that? I used to seriously ask myself that before I launched ideas, and that’s why this mistake of a believing I had to raise a venture to start a startup was not great, but then trying to bootstrap ideas that just weren’t bootstrap able is another thing that I wouldn’t do again. 

Mistake number four was believing that business books would give me the secret to success as an entrepreneur. And it wasn’t just business books, it was believing that one person out there had the answer that would help me succeed. Maybe it was courses, maybe it was info products that were being sold, but business books were certainly a part of this, especially in the early two thousands and the 2010s. Most business books lacked any tactical value. They were either glossy success stories or high level theory or both that were ghost written by someone who wanted their name on a book. So pretty much all the business books I read during this time were useless to someone like me trying to forge an unconventional path. I needed much more tactical approaches. I couldn’t rely on having Kid Rock at my launch party or having Tech Crunch right about my startup. 

I needed to generate actual traffic to a website. So how do you do that? How do you do that? In 2006, there’s no social media. There was SEO, I think AdWords was just coming about. I actually don’t recall. Certainly there’s banner ads, there’s web rings, there were things around, and there were social news sites like Dig Reddit. Again, there were a bunch of others that I don’t remember the names of. And so learning how to use those to market what I was building was a huge step in my career. Problem was there were exactly zero business books that talked about any of that because it was too new. It’s a little better now, but you still have to pick books that focus on what you want to do. So think about the SaaS playbook. There’s a reason that I write books. I’ve told people, have you ever heard the term hate watching, where you start watching a Netflix show and then you kind of hate it, but you keep watching it and you hate watching? 

I kind of hate write books. What I do is I go out looking for a book that has the information that I want, and when I don’t find it, I get mad and I write that book. That was a SaaS playbook. Ruben, founder of Sewell actually really encouraged me to write it, and he said, our space, the ambitious B2B SaaS founders really needs a book that covers not only high level thinking, but that digs in deep into the strategies and the tactics to actually build a SaaS company and not just tell the story, Hey, here’s a SaaS company and here’s all the behind the scenes, and that’s fun too. That’s fun, but that will not give you the secrets to succeeding as an entrepreneur. Zero to Sold by Harvard Call is another good book that you should read, especially if you’re bootstrapping like an indie hacker or lifestyle business. 

It’s great. Versus a book like Shoe Dog or Zero to One, I enjoy those books. I’ve read them both. They’re both entertaining. Neither of those will help you as a bootstrapper. You’ll probably take away almost nothing from them. And again, those books are fun and interesting, and I’ve read them, but they just won’t move you closer. But beyond that, I want to make the point that even with SaaS Playbook or at Traction by Gabriel Weinberg, zero to sold whatever book you’re going to read in our space, believing that that book will give you the answer and the true secret and will guarantee success, that’s a mistake as well. And I think when I was really young, I was naive enough to think that a book would make me successful. A book can help you learn more, can give you the knowledge to be more successful, but you still have to put in the work, develop your skills and push things forward on your own. 

And you’re going to have to make a lot of hard decisions with incomplete information and ship, ship be right most of the time and get things out the door in order to be successful. At a certain point, you do have to stop reading business books and start shipping, and that was something that I definitely struggled with early on in my entrepreneurial journey. Mistake number five was becoming hellbent on being a solopreneur, not just a single founder, but I didn’t want any full-time employees, anyone relying on me. And this came about because I worked at several corporate jobs where I didn’t really like my coworkers. Actually, there were some really cool coworkers that I got along with. They were always the a plus players, the really solid devs, the great managers, the people who cared. It was 60, 70% of the staff that just didn’t give a shit. 

And I was grinding. I was staying late. It was fun because I was writing code to ship and get things into production. I don’t know, I loved it. I wanted to build meaningful things, and I really cared, and I got so burned out on working with people that I just didn’t enjoy working with who kind of didn’t care that I said when I become an entrepreneur. And as I became an entrepreneur and started paying my full-time salary through products, I said, I’m not going to hire anyone ever. I want to do this all on my own. And that mindset worked for me for a time when my ambitions were small, when I wanted to make 120, 150, $200,000 a year, and this was in 2000, let’s say 6, 7, 8 money. So what is it? 40, 50% more than that now. So it’s not a bad living. 

We lived in California, we owned a home, and that mindset worked while my ambition stayed small, but then at a certain point I realized I want to build something meaningful as well. And at that point, it became painfully clear to me that I would want someone to collaborate with that I would want people I could rely on. This is where the idea of task level, project level and owner level thinkers came about, and I had a bunch of task level thinkers. That’s all I had. I didn’t even have project level thinkers in the early days. It was because I couldn’t afford them, but even once I could afford them, I didn’t realize it was a blind spot for me, didn’t realize that I needed to hire project and owner level thinkers or else I became not only a bottleneck, but a project manager and someone who was basically just managing a bunch of task level thinkers. 

And while I’m actually good at doing that, it’s a lot of my background as a developer, and even in construction, I did some project management, but I don’t love it. It’s not what I want to do day to day as an entrepreneur. And it took me years to realize and then to accept that I maybe the first person who did the hire, a bunch of contractors approach. I did this from 2006 until about 2012, and it worked well in the early days, and then there was a lot of turnover. There was no loyalty and there was no cohesion. The contractors didn’t even really know each other, so it was barely a team. And the approach wound up sucking because my entire job was managing contractors, managing projects, assigning things, checking on things, and it’s like it’s not fun. And in the early days, I was grinding because I was like, I want to quit my day job. 

I wound up quitting the day job. Well, by this time, I was actually, it was my first company and I was a consultant. I was a freelancer doing dev work, and then I had other consultants that I was contracting with to help me. So it’s kind of like a micro agency is how I’ve always phrased it. And I was doing that from, I believe it was like oh 5, 0 6 until oh eight. And in oh eight, I got rid of my last client. Basically that contract ended and I had complete product income by mid to late 2008, and I kept doing the solopreneur hire contractor approach after that, and it really wore out. Its welcome if I’m being honest. And it took me too long to see it. And then once I saw it, it took me too long to admit, you know what? I want to do something bigger. 

I don’t want to just be a paper pusher in essence or a project manager. I want to actually get shit done with ambitious people who really want to build something incredible. And that was around the time that this podcast came about, that MicroComp started, that I started Drip and I realized I was going to need to level up my game and just being a solopreneur and trying to be that island off on my own was not going to yield the results and bring me the impact that I wanted to have. Mistake number six was buying into the arrival fallacy. So the arrival fallacy is when you say things like, if I just had a SaaS app on the side that did $2,000 a month, then I’ll be happy. If I just had a product that made enough so I could quit my day job, then I’d be happy. 

If I just had one that did 20 or $30,000 of MRR, then I’ll be happy. And if I just sold a company for millions of dollars, then I’ll be happy. The problem with this is you need to be happy along the way. You are never going to have arrived. It’s a fallacy to believe that, and I know that now. And in fact, by the time I sold Drip in 2016, I knew that, but I had these dramatic ups and downs where I thought, I’ll be happy forever. I mean, even saying it out loud is so naive now, but I hear a lot of people talking about this, and when I say naive, I don’t mean like, oh, you’re dumb. I was there too. It’s easy to believe this, and that’s why I’m talking about this on the podcast. We are ambitious startup founders. We are entrepreneurs. 

We’re always going to seek stuff that is incredibly challenging. We want learning. We want to move things forward. We want to have some type of impact. We want to do interesting things. You’re never going to be happy for very long. This is the curse that we have as entrepreneur. It’s a blessing and a curse. It’s a blessing because it motivates us to do things to ship and to grind and to believe in the growth mindset that we’ll get better and that we’ll figure it out and that we can change our lives and the lives of those around us through entrepreneurship. But it’s a curse because it can mean that you’re never happy. And so the work that I’ve done on myself over the past 15 years, probably definitely more than 10, because it was in between 2010 and 2015 that I really started working on this, and I kind of admitted to myself, you know what? 

Just admit you’re never going to have arrived. How can you be happy along the way? And it wasn’t as simple as logically stating that there was a lot of inner work on my own and with a therapist, and you may not have this, and that’s great, but this was absolutely me chasing a finish line that didn’t exist year in, year out. And every victory I had was inevitably dashed because after 3, 6, 9 months, I became unhappy. I was chasing a finish line that didn’t exist, and I will never do that again. Mistake number seven is going to seem like an interesting left turn after a lot of these higher level or philosophical mistakes. But mistake number seven was not starting an email list sooner. So by the time 2008, nine rolled around, I had been blogging since 2005 and I was putting in several hundred hours a on it, and I would, from my day job as a developer during lunch, instead of going out with the other folks who went out, I packed a lunch and I would drive down the street and I would open up my laptop and I would write blog posts almost every day. 

And then I would do that nights and weekends when I ran out of steam coating stuff or if I was in between coating projects and I was completely disenfranchised and saying, none of this is ever going to work. That was a big thing. This just isn’t going to work. I would tell Sherry, no one’s ever done this, so I just dunno that I can do it. But I blogged a lot. I was writing, and around this time, 2008 or oh nine, I had 25,000 RSS subscribers, but I think I only had an email list of probably maybe a thousand tops. I knew the power of email with my software products and info products and other stuff that I had at the time, but I hadn’t prioritized building that list until about somewhere in that range, like oh nine, maybe 2010. And I feel like I lost quite a bit of time and opportunity because of that. 

Now, in retrospect, maybe what I’m saying is I’m really happy that I did start then because nowadays I don’t know that it matters. I don’t know if my list had been, because my list would not have been 25,000 emails. There’s no chance maybe at most it would’ve been 2,500 or 5,000. And these days, my lists are so much larger than that, that it’d basically be a rounding error. But much like most of these mistakes, I believe it cost me time because not having an email list meant I then had to go build one to launch my next thing. When we launched the podcast, when I launched my book, I didn’t have a big email list, and I had to kind of build those up. So it’s not a, oh, it cost me everything, but it is an, oh, it costs me months and maybe a year or two. 

I don’t know. It’s always hard to guess. But each of these things cost me time on my journey, even though I have obviously experienced quite a bit of success, at least in the way that I’ve defined it. Mistake number eight was taking random internet opinions too seriously. So early on I assumed, again, I say these things and I laugh because it’s like, this is so preposterous, but I assumed that someone with a confident opinion online was qualified to give that advice. Maybe it’s because how I was raised, maybe it’s because of going to school and university and there are always being someone there teaching who knew the stuff, but there were loud voices. And it took me years to realize that these folks, whether they’re on blogs, forums, social media, actually a lot of them knew far less than I did. And frankly, I gave these opinions too much weight. 

I think it sent me off track. And especially when people were negative about something that I was building, I took them way too seriously. So I would get emails about hit tail or emails about my book or emails about Drip once we were building it, and folks would’ve these really strong opinions about ux, like, you should definitely never do this in your user interface. I can’t believe you actually even thought that a button should be square or rectangle or round or just insert whatever shape here. Button should never be round or a top. NAB should never be this way. And it’s like, oh, wow. They must know if they’re this opinionated. This must be a law that we all ascribe to. And it took me way too long to realize a lot of these people don’t know what the fuck they’re talking about. A lot of these people want to hear themselves talk. 

They couch themselves as experts. They just want spout off on an internet form or via email to you or on a blog or social media. These days, it’s social media or via support requests. And so the danger in listening to these folks is, A, they can send you off course, and B, they can really be a detriment to your mental health if they say a lot of negative things and you take them to heart of like, oh, I’m screwing up. I am bad. I am dumb. I don’t know what I’m doing. And these days I know better to brush them off. And I’m glad I learned that at least a decade ago, but it took me at least a decade to learn it, and I wished that I had learned it much sooner. And I want to add a clarification to this. The solution is not to listen to no one. 

It’s to listen to people who you trust to give you honest feedback that comes from a genuine place, but also qualified feedback. So it’s folks in your mastermind if they’re ahead of you or you believe that they’re smart founders who are getting things done, it’s advisors, it’s investors, it’s your network. That’s why these days, I have a pretty tight network of folks that I can go to and say, how am I screwing up? Should I make this decision or this other decision? It’s a really big strategic whatever, and I can talk to people and try to get their input. So I do listen to people. I just don’t listen to randoms on the internet. Mistake number nine was overestimating my abilities after early successes. So after I’d had wins with an e-commerce website, just beach house.com folks, info products, a book, my blog, a SaaS app, downloadable software, another not downloadable software. 

There’s all kinds of stuff. I assumed that anything I started would be a hit. And even though I had done it before, I underestimated how hard it would be to find product-market fit again. And as we launched Drip, I overextended myself financially because I believed that I could find it just right off the bat. I was going to launch right into product-market fit. And the result of this over extension was I had a very hard 2014, and I think a little bit of 2015 too, where I was mentally exhausted. I was emotionally drained, stressed out all the time, and financially I was just wondering where the next five, 10, $20,000 was going to come from, where the next payroll was going to come from. My overconfidence in my ability to just find it magically led to honestly to burnout and strain on my marriage and some other relationships that I had, and definitely a lot of strain on my mental health. 

And it was all because I thought that my execution and my skillset at the time would guarantee success quickly. And that is a lesson that I learned, which was do not overestimate your abilities. Give yourself a little leeway. You are smart, you figured some things out, you have some skills, but you are not infallible just because you’ve had a few successes. Mistake number 10 was ignoring my anxiety and letting it control my outlook on the world and frankly, on my startups and my products. So naturally I run a bit anxious, not catastrophic, but I run a bit anxious. But it’s enough that if unchecked, my inner voice can blow up small issues into mental disasters. So I would let things that in retrospect were not that big of a deal, and I would let them just blow up on me and I’d perseverate on ’em and I would not sleep well, and I would think about them constantly and perseverate during the day and then in the evening, and I just couldn’t get away from them. 

The other thing I did was I rarely asked for help, and I lived in a constant state of stress even though things were actually going quite well, like the story, the story is true. Success was there. It was happening. We were growing two grand of MRR per month and then five grand of MRR per month and then 10 grand of MRR per month. And we hit seven figures and we were doing well, but the success didn’t feel good because I was always bracing for the next crisis. And frankly, I was letting my natural proclivities towards thinking about what could go wrong, which usually is kind of a good mindset or a good skill to have, but I was letting it run rampant. And that mindset of catastrophizing everything, it made the journey miserable, and it took me way too long to recognize and work on it. 

And it wasn’t really until after we sold Drip that I realized and acknowledged and then did the inner work. It took to not feel that way all the time. And I regret living those years in that constant anxiety. People have asked me, do you ever regret selling drip? And I’ve never had a day where I regretted, but I do regret the way that I operated during those years and the way I let my own mental health deteriorate. And this was one of the biggest reasons. Mistake number 11 is an interesting counterpoint to number nine. So nine was overestimating my abilities after early successes. Number 11 was not letting my wins build my confidence. So as the years ticked on and I had more success and more wins and more experience even after all those years of success, and this includes publishing books, building an audience, launching profitable products, growing them, I still struggled with imposter syndrome. 

I doubted myself quite a bit. I questioned at certain points, Hey, was it all just luck? I didn’t give myself enough credit for having built a skillset, a tool belt of skills, and having worked hard and probably getting a little lucky, of course we all do, but I failed to give myself the credit, and I worried that confidence would lead to ego. But the truth is, I could have allowed myself quite a bit more belief in my own abilities, especially as I executed. And over time, I wished that I had let my wins build my confidence because that self-doubt did hold me back at times. It took a toll emotionally and it held me back. I think from moving faster and from making bigger bets, and so much like many of these in the list, it’s not something that caused me to not be successful, but they are things that made the journey take a lot longer than it needed to for me. 

And the 12th and final mistake that I made was clinging to a scarcity mindset. Even after I had built quite a bit of wealth. I grew up solidly working class, a step above being poor, and we were never on food stamps or welfare, but there were certainly times where I was worried as a kid that we were going to be, we were a family of six with one working parent. My dad worked construction and they always made the house payment, but I didn’t know that they were always going to make the house payment. We definitely drank powdered milk. There were some tough times. And so I grew up with a scarcity mindset around money, and it took me way too long to shift my thinking. And even after earning amounts and putting ’em in the bank that I had never imagined I would have, I had a hard time spending rationally or adjusting my reality of financial abundance. 

What’s the harm in that? You might think, well, when you have millions of dollars in the bank, but you’re not willing to pay more than X amount per month in rent when you move to Minneapolis because your company just got acquired. And so you kind of live in a crappier house than you should, or you go to buy a house and you’re really not willing to spend what we could very much afford because you have this old script running, or you don’t want to buy an expensive car, expensive, a 40 or $50,000 car that actually runs really well in the winter, has all wheel drive, has heated seats, has remote start, has a heated steering wheel when it’s 20 or 30 below here in the winter. These are nice to haves, but they are nice to have. And I kept driving a salvage title car that I had paid $9,000 cash for 10, 12 years prior, which was fine. 

I don’t need the luxury. But at a certain point, it becomes miserly to have this money sitting there not giving you things that would help improve your quality of life. And I got in arguments with Sherry about this. I was kind of insufferable when we would go to book a vacation, I would say, oh, the budget’s this, and then wouldn’t want to budge on it, even though realistically there was plenty of room there. So I think any example I bring up, you’re going to think, oh, well, you don’t really need to do that. And you’re right, it’s not about the specifics. Each of us values things differently. Some people really want a fancy car. Some people want to fly first class or private the rest of their lives. Some people want to own really expensive comic books or Beatles gold album, and none of those are wrong. 

None of those are things that you shouldn’t ascribe to. The thing that I did poorly was maintaining this fear, this anxiety, this scarcity mindset around money and continuing not to spend it. Well, when we needed to hire help, because we had several kids who were struggling, and Sherry and I were struggling to do our day jobs and also homeschool a kid, and there’s a whole personal story around this that is, I’ll say, challenging to go into the details of, but I remember thinking, well, we just can’t afford it. And in fact, we could have, but I was clinging to that scarcity mindset even though we did in fact have the money to do it. So as you can tell, these regrets are a lot of them are mindset things, and a lot of them either cost me months or years, or they cost me my mental health. 

And I found that interesting as I walked through this list that mistakes in business bets that I made where it didn’t pan out. Oh, I remember I wrote someone a $2,000 check to buy a website or a product, and they basically scammed me. So would I think that that’s a big mistake? Well, it just wasn’t because I just rolled with it because I had a $2,000 at the time to spend. It was a bummer. But it’s not one of my biggest mistakes I’ll never make again because I was making a calculated risk at the time and it didn’t work out. But these mistakes I’m talking about are the ones that I have vowed that I will try to never make again. These are the ones that truly cost me the most over the last 20 years of being a founder. In my next episode, I’m going to talk about what I got, what I believe are my best entrepreneurial decisions, or really the reasons that I believe that in spite of these mistakes that I made along the way, I think by most measures, and certainly by the way that I personally measure success, I feel like I’ve achieved all the success that I could ever want. 

And everything from here on out is the whipped cream and the cherry on top of the sundae. I think the real reason that I have found this success is because of the list of 12 entrepreneurial decisions, so to speak, that I’m going to be talking about in next week’s episode. So tune in then to hear the upside and the positive. This episode, it feels a little bit like a downer, but I am really happy to have recorded this because I hope for me, this is an episode I will refer people to in the future of what are your biggest mistakes? What are the things you wish you’d done differently? And I think this is now the definitive version. So thanks for joining me today as I walk down memory lane and the pain and some of the decisions that obviously I regret. That’s the whole point of the episode, but I appreciate you being here to hear it. This is Rob Walling signing off from episode 781.