NEVER Make These 6 Mistakes (Lessons from 20 Years in Business)

After two decades as an entrepreneur, After two decades as an entrepreneur, I've racked up my fair share of regrets. I've racked up my fair share of regrets. I've racked up my fair share of regrets. Some gave me massive headaches, others Some gave me massive headaches, others Some gave me massive headaches, others stole countless nights of sleep, and a stole countless nights of sleep, and a stole countless nights of sleep, and a few almost cost me my entire business. few almost cost me my entire business. few almost cost me my entire business. So many of these mistakes were So many of these mistakes were So many of these mistakes were avoidable, and in those cases, I wish avoidable, and in those cases, I wish avoidable, and in those cases, I wish I'd done things differently. After I'd done things differently. After I'd done things differently. After watching this video, you can avoid watching this video, you can avoid watching this video, you can avoid making the same mistakes I made. I'm Rob making the same mistakes I made. I'm Rob making the same mistakes I made. I'm Rob Walling, and over the years, I've Walling, and over the years, I've Walling, and over the years, I've written five books, started six written five books, started six written five books, started six companies, and invested in more than 220 companies, and invested in more than 220 companies, and invested in more than 220 startups. But that highlight reel startups. But that highlight reel startups. But that highlight reel doesn't show the full picture. In fact, doesn't show the full picture. In fact, doesn't show the full picture. In fact, it leads me in to my first mistake. I it leads me in to my first mistake. I it leads me in to my first mistake. I seriously overestimated my abilities seriously overestimated my abilities seriously overestimated my abilities after a few early wins. So, in the first after a few early wins. So, in the first after a few early wins. So, in the first 5 years of my entrepreneurial journey, I 5 years of my entrepreneurial journey, I 5 years of my entrepreneurial journey, I had a handful of successful software had a handful of successful software had a handful of successful software products. I had a successful blog and my products. I had a successful blog and my products. I had a successful blog and my podcast was just getting started. So, podcast was just getting started. So, podcast was just getting started. So, after some wins and writing my first after some wins and writing my first after some wins and writing my first book, I kind of assumed that anything I book, I kind of assumed that anything I book, I kind of assumed that anything I started would be a hit. But I started would be a hit. But I started would be a hit. But I underestimated how hard product market underestimated how hard product market underestimated how hard product market fit is to find, especially with SAS. And fit is to find, especially with SAS. And fit is to find, especially with SAS. And at a certain point, I overextended at a certain point, I overextended at a certain point, I overextended myself financially in the process. And myself financially in the process. And myself financially in the process. And the result was a really tough stretch.

the result was a really tough stretch. the result was a really tough stretch. This was around 2014, 2015, mentally, This was around 2014, 2015, mentally, This was around 2014, 2015, mentally, emotionally, and financially. It was a emotionally, and financially. It was a emotionally, and financially. It was a huge strain on me. My overconfidence led huge strain on me. My overconfidence led huge strain on me. My overconfidence led to burnout and strain in my marriage. to burnout and strain in my marriage. to burnout and strain in my marriage. And it was all because I thought And it was all because I thought And it was all because I thought execution alone would guarantee success. execution alone would guarantee success. execution alone would guarantee success. And the fact that I had a few wins under And the fact that I had a few wins under And the fact that I had a few wins under my belt would also guarantee success. my belt would also guarantee success. my belt would also guarantee success. It's easy to have one, two, three wins It's easy to have one, two, three wins It's easy to have one, two, three wins and feel like you're infallible. But the and feel like you're infallible. But the and feel like you're infallible. But the reality is that every new product is a reality is that every new product is a reality is that every new product is a new challenge. Product market fit is new challenge. Product market fit is new challenge. Product market fit is always, always hard. Whether it's your always, always hard. Whether it's your always, always hard. Whether it's your first time or your fifth time finding first time or your fifth time finding first time or your fifth time finding it, it's going to take longer than you it, it's going to take longer than you it, it's going to take longer than you want. More time, more money, and more want. More time, more money, and more want. More time, more money, and more effort. And overconfidence can lead you effort. And overconfidence can lead you effort. And overconfidence can lead you to make risky decisions, can lead to to make risky decisions, can lead to to make risky decisions, can lead to financial strain, can lead to burnout. financial strain, can lead to burnout. financial strain, can lead to burnout. as it did with me. So, the lesson here as it did with me. So, the lesson here as it did with me. So, the lesson here is don't assume that past successes is don't assume that past successes is don't assume that past successes guarantee future wins. Always give guarantee future wins. Always give guarantee future wins. Always give yourself the leeway and ample time to yourself the leeway and ample time to yourself the leeway and ample time to get that next company off the ground. get that next company off the ground. get that next company off the ground. So, that overconfidence set me up for So, that overconfidence set me up for So, that overconfidence set me up for disappointment. I thought hitting those disappointment. I thought hitting those disappointment. I thought hitting those milestones would finally make me happy, milestones would finally make me happy, milestones would finally make me happy, but it turns out the finish line always but it turns out the finish line always but it turns out the finish line always moves. And that's why regret number two moves. And that's why regret number two moves. And that's why regret number two is buying into the arrival fallacy. So, is buying into the arrival fallacy. So, is buying into the arrival fallacy. So, the arrival fallacy is believing that the arrival fallacy is believing that the arrival fallacy is believing that happiness is just over the next happiness is just over the next happiness is just over the next milestone. I kept telling myself once I milestone. I kept telling myself once I milestone. I kept telling myself once I make enough money to quit my day job make enough money to quit my day job make enough money to quit my day job then I'll be happy. Then it became once then I'll be happy. Then it became once then I'll be happy. Then it became once I hit 20,000 or 30,000 a month then I'll I hit 20,000 or 30,000 a month then I'll I hit 20,000 or 30,000 a month then I'll be happy. Every time I reach those be happy. Every time I reach those be happy. Every time I reach those milestones the happiness faded after a milestones the happiness faded after a milestones the happiness faded after a few months. I was effectively chasing a few months. I was effectively chasing a few months. I was effectively chasing a finish line that doesn't exist. Every finish line that doesn't exist. Every finish line that doesn't exist. Every new win you have in your career will new win you have in your career will new win you have in your career will bring a short-term high and you'll feel

bring a short-term high and you'll feel bring a short-term high and you'll feel like well finally I've arrived now I can like well finally I've arrived now I can like well finally I've arrived now I can be happy forever. But it does fade over be happy forever. But it does fade over be happy forever. But it does fade over time. Maybe it's a few weeks maybe it's time. Maybe it's a few weeks maybe it's time. Maybe it's a few weeks maybe it's a few months. The fact is a few months. The fact is a few months. The fact is entrepreneurship is a journey. A entrepreneurship is a journey. A entrepreneurship is a journey. A constant ongoing journey. There is no constant ongoing journey. There is no constant ongoing journey. There is no finish line. Even selling your company finish line. Even selling your company finish line. Even selling your company is just one more step in that journey. is just one more step in that journey. is just one more step in that journey. It's not the end. It took me probably It's not the end. It took me probably It's not the end. It took me probably 10, 15 years of inner work, of doing 10, 15 years of inner work, of doing 10, 15 years of inner work, of doing founder retreats, of doing therapy, of founder retreats, of doing therapy, of founder retreats, of doing therapy, of just really digging into why I was just really digging into why I was just really digging into why I was unhappy every 18 to 24 months. Why did I unhappy every 18 to 24 months. Why did I unhappy every 18 to 24 months. Why did I plummet into this pit of despair? Well, plummet into this pit of despair? Well, plummet into this pit of despair? Well, the reason was is that I kept basing my the reason was is that I kept basing my the reason was is that I kept basing my happiness on that next hill, on climbing happiness on that next hill, on climbing happiness on that next hill, on climbing the next peak, and I thought that that the next peak, and I thought that that the next peak, and I thought that that would bring me happiness, which was would bring me happiness, which was would bring me happiness, which was obviously a mistake. So, the lesson here obviously a mistake. So, the lesson here obviously a mistake. So, the lesson here is find ways to be happy along the way, is find ways to be happy along the way, is find ways to be happy along the way, not just at some end point or some fake not just at some end point or some fake not just at some end point or some fake finish line that you have in your head. finish line that you have in your head. finish line that you have in your head. Celebrate the wins that come, but Celebrate the wins that come, but Celebrate the wins that come, but realize that that happiness, especially realize that that happiness, especially realize that that happiness, especially if you're a driven entrepreneur who if you're a driven entrepreneur who if you're a driven entrepreneur who wants to learn and do interesting wants to learn and do interesting wants to learn and do interesting things, that happiness will fade. And things, that happiness will fade. And things, that happiness will fade. And even when I did reach those milestones, even when I did reach those milestones, even when I did reach those milestones, I found it hard to feel like I'd I found it hard to feel like I'd I found it hard to feel like I'd actually accomplished something. And actually accomplished something. And actually accomplished something. And that led me to my next mistake. Not that led me to my next mistake. Not that led me to my next mistake. Not letting my wins build my confidence.

letting my wins build my confidence. letting my wins build my confidence. Even after building a successful blog Even after building a successful blog Even after building a successful blog and a podcast, publishing several books, and a podcast, publishing several books, and a podcast, publishing several books, starting multiple successful companies, starting multiple successful companies, starting multiple successful companies, I struggled to feel legitimate. I felt I struggled to feel legitimate. I felt I struggled to feel legitimate. I felt imposttor syndrome most days. I doubted imposttor syndrome most days. I doubted imposttor syndrome most days. I doubted myself. I questioned at times if it was myself. I questioned at times if it was myself. I questioned at times if it was all luck. I failed to give myself the all luck. I failed to give myself the all luck. I failed to give myself the credit that I had actually built up an credit that I had actually built up an credit that I had actually built up an impressive skill set and I had put in impressive skill set and I had put in impressive skill set and I had put in the work to build these incredible the work to build these incredible the work to build these incredible businesses. I also worried that businesses. I also worried that businesses. I also worried that confidence would lead to ego. But the confidence would lead to ego. But the confidence would lead to ego. But the truth is I could have allowed myself a truth is I could have allowed myself a truth is I could have allowed myself a bit more belief in my own abilities. bit more belief in my own abilities. bit more belief in my own abilities. That self-doubt held me back and it took That self-doubt held me back and it took That self-doubt held me back and it took a toll emotionally. Realize that healthy a toll emotionally. Realize that healthy a toll emotionally. Realize that healthy confidence is not the same as ego. That confidence is not the same as ego. That confidence is not the same as ego. That starting to come into your own and starting to come into your own and starting to come into your own and realize, oh, I'm I'm good at this. To realize, oh, I'm I'm good at this. To realize, oh, I'm I'm good at this. To say I'm good at something, does not mean say I'm good at something, does not mean say I'm good at something, does not mean you're conceited or full of yourself. In you're conceited or full of yourself. In you're conceited or full of yourself. In addition, not recognizing your own addition, not recognizing your own addition, not recognizing your own progress can hold you back from making progress can hold you back from making progress can hold you back from making bigger bets. And if you're going to bigger bets. And if you're going to bigger bets. And if you're going to build an incredible entrepreneurial build an incredible entrepreneurial build an incredible entrepreneurial career, you want to make a series of career, you want to make a series of career, you want to make a series of everinccreasing but manageablysized bets everinccreasing but manageablysized bets everinccreasing but manageablysized bets or manageably sized mistakes. And if you or manageably sized mistakes. And if you or manageably sized mistakes. And if you don't internalize that you're actually don't internalize that you're actually don't internalize that you're actually getting better and turn down that getting better and turn down that getting better and turn down that imposttor syndrome, you won't make these imposttor syndrome, you won't make these imposttor syndrome, you won't make these bigger bets and you'll often be stuck bigger bets and you'll often be stuck bigger bets and you'll often be stuck just spinning at the same level. Having just spinning at the same level. Having just spinning at the same level. Having imposter syndrome and all these doubts imposter syndrome and all these doubts imposter syndrome and all these doubts can slow your growth and your can slow your growth and your can slow your growth and your decision-m. So the lesson here is let decision-m. So the lesson here is let decision-m. So the lesson here is let your wins build your confidence. Don't your wins build your confidence. Don't your wins build your confidence. Don't just see the flaws. And when you're just see the flaws. And when you're just see the flaws. And when you're always doubting yourself, it takes a always doubting yourself, it takes a always doubting yourself, it takes a toll on your mindset and even your toll on your mindset and even your toll on your mindset and even your mental health. For me, that meant mental health. For me, that meant mental health. For me, that meant dealing with anxiety that I wasn't even dealing with anxiety that I wasn't even dealing with anxiety that I wasn't even acknowledging. So, I'm naturally an acknowledging. So, I'm naturally an acknowledging. So, I'm naturally an anxious person. Not catastrophically so,

anxious person. Not catastrophically so, anxious person. Not catastrophically so, but enough that I let that anxious inner but enough that I let that anxious inner but enough that I let that anxious inner voice blow up small issues into mental voice blow up small issues into mental voice blow up small issues into mental disasters. I don't do this anymore. But disasters. I don't do this anymore. But disasters. I don't do this anymore. But 10, 15 years ago, it was a real problem. 10, 15 years ago, it was a real problem. 10, 15 years ago, it was a real problem. I rarely asked for help. I lived in a I rarely asked for help. I lived in a I rarely asked for help. I lived in a near constant state of stress. And even near constant state of stress. And even near constant state of stress. And even when things were going well, success when things were going well, success when things were going well, success didn't feel good because I was always didn't feel good because I was always didn't feel good because I was always bracing for the next crisis. That kind bracing for the next crisis. That kind bracing for the next crisis. That kind of mindset makes the journey miserable. of mindset makes the journey miserable. of mindset makes the journey miserable. You can't celebrate your wins and you You can't celebrate your wins and you You can't celebrate your wins and you always look at the negatives. It took me always look at the negatives. It took me always look at the negatives. It took me a long time to recognize that I was even a long time to recognize that I was even a long time to recognize that I was even feeling this and to work on it. This was feeling this and to work on it. This was feeling this and to work on it. This was another place where I had to do a bunch another place where I had to do a bunch another place where I had to do a bunch of inner work and go to therapy and just of inner work and go to therapy and just of inner work and go to therapy and just spend years kind of unpacking what I was spend years kind of unpacking what I was spend years kind of unpacking what I was feeling and why I was feeling that and feeling and why I was feeling that and feeling and why I was feeling that and the realities of the world and to look the realities of the world and to look the realities of the world and to look at the successes after I had sold Drip. at the successes after I had sold Drip. at the successes after I had sold Drip. I felt amazing, but inside I was still I felt amazing, but inside I was still I felt amazing, but inside I was still stressed and in this panic mode all the stressed and in this panic mode all the stressed and in this panic mode all the time. And it took me a while to time. And it took me a while to time. And it took me a while to recognize that the stuff inside of me recognize that the stuff inside of me recognize that the stuff inside of me was often different than the way other was often different than the way other was often different than the way other people saw me. And it was different than people saw me. And it was different than people saw me. And it was different than frankly the reality of the situation frankly the reality of the situation frankly the reality of the situation which was, hey, I'm a successful which was, hey, I'm a successful which was, hey, I'm a successful entrepreneur. Why don't I feel like one?

entrepreneur. Why don't I feel like one? entrepreneur. Why don't I feel like one? The lesson here is that mental health The lesson here is that mental health The lesson here is that mental health matters. Don't let anxiety run matters. Don't let anxiety run matters. Don't let anxiety run unchecked. Get help. Looking back, a lot unchecked. Get help. Looking back, a lot unchecked. Get help. Looking back, a lot of my anxiety came from trying to do of my anxiety came from trying to do of my anxiety came from trying to do everything myself all the time. And that everything myself all the time. And that everything myself all the time. And that brings me to my next mistake, which was brings me to my next mistake, which was brings me to my next mistake, which was becoming hellbent on being a soloreneur. becoming hellbent on being a soloreneur. becoming hellbent on being a soloreneur. So, I embraced the solarpreneur ideal So, I embraced the solarpreneur ideal So, I embraced the solarpreneur ideal and resisted hiring anyone for the first and resisted hiring anyone for the first and resisted hiring anyone for the first probably five, well, it wasn't quite 10, probably five, well, it wasn't quite 10, probably five, well, it wasn't quite 10, but 5 to seven years of my journey. That but 5 to seven years of my journey. That but 5 to seven years of my journey. That mindset can work if your ambitions are mindset can work if your ambitions are mindset can work if your ambitions are small or if you get really lucky. But if small or if you get really lucky. But if small or if you get really lucky. But if you want to build something meaningful, you want to build something meaningful, you want to build something meaningful, you'll almost always need to collaborate you'll almost always need to collaborate you'll almost always need to collaborate with smart, interesting, ambitious with smart, interesting, ambitious with smart, interesting, ambitious people. And it took me years to accept people. And it took me years to accept people. And it took me years to accept that. The hire a bunch of contractors that. The hire a bunch of contractors that. The hire a bunch of contractors approach sucks because then your entire approach sucks because then your entire approach sucks because then your entire job is managing contractors. really hard job is managing contractors. really hard job is managing contractors. really hard to build something interesting with that to build something interesting with that to build something interesting with that approach to not actually have a team. approach to not actually have a team. approach to not actually have a team. The challenge was I had worked corporate The challenge was I had worked corporate The challenge was I had worked corporate jobs for years and I didn't like my jobs for years and I didn't like my jobs for years and I didn't like my co-workers and so that experience made co-workers and so that experience made co-workers and so that experience made me want to avoid hiring cuz I wanted to me want to avoid hiring cuz I wanted to me want to avoid hiring cuz I wanted to control everything and that worked fine control everything and that worked fine control everything and that worked fine for small goals for these little apps for small goals for these little apps for small goals for these little apps doing 10 20 30 grand a month but it doing 10 20 30 grand a month but it doing 10 20 30 grand a month but it became a bottleneck when I wanted to became a bottleneck when I wanted to became a bottleneck when I wanted to build a seven or eight figure SAS build a seven or eight figure SAS build a seven or eight figure SAS company. You may have heard me talk company. You may have heard me talk company. You may have heard me talk about task level project level and owner about task level project level and owner about task level project level and owner level thinkers. I was dealing solely level thinkers. I was dealing solely level thinkers. I was dealing solely with task level contractors because I with task level contractors because I with task level contractors because I didn't want anyone to be relying on me didn't want anyone to be relying on me didn't want anyone to be relying on me and the more senior folks that I hired, and the more senior folks that I hired, and the more senior folks that I hired, not only were they more expensive, but not only were they more expensive, but not only were they more expensive, but it it felt like I would have to do it it felt like I would have to do it it felt like I would have to do career development and I was going to be career development and I was going to be career development and I was going to be managing a team. And realistically, managing a team. And realistically, managing a team. And realistically, that's probably true. But to do anything that's probably true. But to do anything that's probably true. But to do anything interesting and build great businesses,

interesting and build great businesses, interesting and build great businesses, you need project and owner level you need project and owner level you need project and owner level thinkers, not just task doers. So the thinkers, not just task doers. So the thinkers, not just task doers. So the lesson here is if your ambitions grow, lesson here is if your ambitions grow, lesson here is if your ambitions grow, so must your willingness to build a real so must your willingness to build a real so must your willingness to build a real team. I see it over and over and over team. I see it over and over and over team. I see it over and over and over across my 224 SAS investments and across across my 224 SAS investments and across across my 224 SAS investments and across the micro comp startups of the rest of the micro comp startups of the rest of the micro comp startups of the rest of us and this YouTube channel community. us and this YouTube channel community. us and this YouTube channel community. In just a moment, I'll share the final In just a moment, I'll share the final In just a moment, I'll share the final point on today's list. A lesson I still point on today's list. A lesson I still point on today's list. A lesson I still have to remind myself even here on have to remind myself even here on have to remind myself even here on YouTube. Before we get to that, if YouTube. Before we get to that, if YouTube. Before we get to that, if you're finding these insights useful, you're finding these insights useful, you're finding these insights useful, you'll probably enjoy the full Startup you'll probably enjoy the full Startup you'll probably enjoy the full Startup for the Rest of Us podcast episode where for the Rest of Us podcast episode where for the Rest of Us podcast episode where I dive even deeper into this list. Plus, I dive even deeper into this list. Plus, I dive even deeper into this list. Plus, I have an additional six of my biggest I have an additional six of my biggest I have an additional six of my biggest entrepreneurial regrets. I can go a lot entrepreneurial regrets. I can go a lot entrepreneurial regrets. I can go a lot deeper into these items on a podcast deeper into these items on a podcast deeper into these items on a podcast than I can in a YouTube video. So, if than I can in a YouTube video. So, if than I can in a YouTube video. So, if you want the extra stories and context you want the extra stories and context you want the extra stories and context that I couldn't fit here, head over to that I couldn't fit here, head over to that I couldn't fit here, head over to your favorite podcast app and search for your favorite podcast app and search for your favorite podcast app and search for Startups for the Rest of Us. You'll find Startups for the Rest of Us. You'll find Startups for the Rest of Us. You'll find the full episode linked in the the full episode linked in the the full episode linked in the description below as well. All right, description below as well. All right, description below as well. All right, let's get to the sixth and final lesson. let's get to the sixth and final lesson. let's get to the sixth and final lesson. It's that taking random internet It's that taking random internet It's that taking random internet opinions, including YouTube comments, opinions, including YouTube comments, opinions, including YouTube comments, too seriously, is probably a bad idea.

too seriously, is probably a bad idea. too seriously, is probably a bad idea. So early on, I assumed anyone with a So early on, I assumed anyone with a So early on, I assumed anyone with a confident opinion online was qualified confident opinion online was qualified confident opinion online was qualified to give advice. It sounds crazy, but 20 to give advice. It sounds crazy, but 20 to give advice. It sounds crazy, but 20 years ago, 15 years ago, it was my years ago, 15 years ago, it was my years ago, 15 years ago, it was my mindset. And it took me years to realize mindset. And it took me years to realize mindset. And it took me years to realize that many of the loud voices on blogs, that many of the loud voices on blogs, that many of the loud voices on blogs, forums, and social media actually knew forums, and social media actually knew forums, and social media actually knew far less than I did about the subject. I far less than I did about the subject. I far less than I did about the subject. I gave their opinions too much weight, gave their opinions too much weight, gave their opinions too much weight, especially when they were negative. especially when they were negative. especially when they were negative. These days, I know better and I brush These days, I know better and I brush These days, I know better and I brush them off. Just because someone is loud them off. Just because someone is loud them off. Just because someone is loud online does not make them correct. Many online does not make them correct. Many online does not make them correct. Many strong opinions online are deeply strong opinions online are deeply strong opinions online are deeply uninformed. And the challenge is that uninformed. And the challenge is that uninformed. And the challenge is that negative feedback can derail you negative feedback can derail you negative feedback can derail you mentally and strategically. So what I do mentally and strategically. So what I do mentally and strategically. So what I do now is I curate who I take feedback now is I curate who I take feedback now is I curate who I take feedback from. Folks in my mastermind, advisers, from. Folks in my mastermind, advisers, from. Folks in my mastermind, advisers, investors, close personal friends, but I investors, close personal friends, but I investors, close personal friends, but I don't let internet randos dictate my don't let internet randos dictate my don't let internet randos dictate my direction or my self-worth. And you direction or my self-worth. And you direction or my self-worth. And you shouldn't either. So the lesson is shouldn't either. So the lesson is shouldn't either. So the lesson is listen to trusted qualified sources and listen to trusted qualified sources and listen to trusted qualified sources and ignore the rest. If you're early in your ignore the rest. If you're early in your ignore the rest. If you're early in your entrepreneurial career and you're not entrepreneurial career and you're not entrepreneurial career and you're not sure where to get started, go watch this sure where to get started, go watch this sure where to get started, go watch this video where I lay out the eight steps to video where I lay out the eight steps to video where I lay out the eight steps to building a SAS from scratch. Thanks for building a SAS from scratch. Thanks for building a SAS from scratch. Thanks for watching. We'll see you next time.