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

Category: Entrepreneurship

Tags: confidenceentrepreneurshipfeedbackmistakesteamwork

Entities: Dripmicro compRob WallingSASStartups for the Rest of Us

Transcript

00:00

After two decades as an entrepreneur, I've racked up my fair share of regrets. Some gave me massive headaches, others stole countless nights of sleep, and a few almost cost me my entire business.

So many of these mistakes were avoidable, and in those cases, I wish

00:15

I'd done things differently. After watching this video, you can avoid making the same mistakes I made.

I'm Rob Walling, and over the years, I've written five books, started six companies, and invested in more than 220 startups. But that highlight reel

00:30

doesn't show the full picture. In fact, it leads me in to my first mistake.

I seriously overestimated my abilities after a few early wins. So, in the first 5 years of my entrepreneurial journey, I had a handful of successful software products.

I had a successful blog and my

00:45

podcast was just getting started. So, after some wins and writing my first book, I kind of assumed that anything I started would be a hit.

But I underestimated how hard product market fit is to find, especially with SAS. And at a certain point, I overextended myself financially in the process.

And

01:02

the result was a really tough stretch. This was around 2014, 2015, mentally, emotionally, and financially.

It was a huge strain on me. My overconfidence led to burnout and strain in my marriage.

And it was all because I thought execution alone would guarantee success.

01:18

And the fact that I had a few wins under my belt would also guarantee success. It's easy to have one, two, three wins and feel like you're infallible.

But the reality is that every new product is a new challenge. Product market fit is always, always hard.

Whether it's your

01:33

first time or your fifth time finding it, it's going to take longer than you want. More time, more money, and more effort.

And overconfidence can lead you to make risky decisions, can lead to financial strain, can lead to burnout. as it did with me.

So, the lesson here

01:49

is don't assume that past successes guarantee future wins. Always give yourself the leeway and ample time to get that next company off the ground.

So, that overconfidence set me up for disappointment. I thought hitting those milestones would finally make me happy, but it turns out the finish line always

02:05

moves. And that's why regret number two is buying into the arrival fallacy.

So, the arrival fallacy is believing that happiness is just over the next milestone. I kept telling myself once I make enough money to quit my day job then I'll be happy.

Then it became once I hit 20,000 or 30,000 a month then I'll

02:23

be happy. Every time I reach those milestones the happiness faded after a few months.

I was effectively chasing a finish line that doesn't exist. Every new win you have in your career will bring a short-term high and you'll feel like well finally I've arrived now I can

02:38

be happy forever. But it does fade over time.

Maybe it's a few weeks maybe it's a few months. The fact is entrepreneurship is a journey.

A constant ongoing journey. There is no finish line.

Even selling your company is just one more step in that journey.

02:54

It's not the end. It took me probably 10, 15 years of inner work, of doing founder retreats, of doing therapy, of just really digging into why I was unhappy every 18 to 24 months.

Why did I plummet into this pit of despair? Well,

03:10

the reason was is that I kept basing my happiness on that next hill, on climbing the next peak, and I thought that that would bring me happiness, which was obviously a mistake. So, the lesson here is find ways to be happy along the way, not just at some end point or some fake

03:27

finish line that you have in your head. Celebrate the wins that come, but realize that that happiness, especially if you're a driven entrepreneur who wants to learn and do interesting things, that happiness will fade.

And even when I did reach those milestones, I found it hard to feel like I'd

03:42

actually accomplished something. And that led me to my next mistake.

Not letting my wins build my confidence. Even after building a successful blog and a podcast, publishing several books, starting multiple successful companies, I struggled to feel legitimate.

I felt

03:58

imposttor syndrome most days. I doubted myself.

I questioned at times if it was all luck. I failed to give myself the credit that I had actually built up an impressive skill set and I had put in the work to build these incredible businesses.

I also worried that confidence would lead to ego. But the

04:14

truth is I could have allowed myself a bit more belief in my own abilities. That self-doubt held me back and it took a toll emotionally.

Realize that healthy confidence is not the same as ego. That starting to come into your own and realize, oh, I'm I'm good at this.

To

04:30

say I'm good at something, does not mean you're conceited or full of yourself. In addition, not recognizing your own progress can hold you back from making bigger bets.

And if you're going to build an incredible entrepreneurial career, you want to make a series of everinccreasing but manageablysized bets

04:47

or manageably sized mistakes. And if you don't internalize that you're actually getting better and turn down that imposttor syndrome, you won't make these bigger bets and you'll often be stuck just spinning at the same level.

Having imposter syndrome and all these doubts can slow your growth and your

05:03

decision-m. So the lesson here is let your wins build your confidence.

Don't just see the flaws. And when you're always doubting yourself, it takes a toll on your mindset and even your mental health.

For me, that meant dealing with anxiety that I wasn't even acknowledging. So, I'm naturally an

05:18

anxious person. Not catastrophically so, but enough that I let that anxious inner voice blow up small issues into mental disasters.

I don't do this anymore. But 10, 15 years ago, it was a real problem.

I rarely asked for help. I lived in a near constant state of stress.

And even

05:35

when things were going well, success didn't feel good because I was always bracing for the next crisis. That kind of mindset makes the journey miserable.

You can't celebrate your wins and you always look at the negatives. It took me a long time to recognize that I was even feeling this and to work on it.

This was

05:52

another place where I had to do a bunch of inner work and go to therapy and just spend years kind of unpacking what I was feeling and why I was feeling that and the realities of the world and to look at the successes after I had sold Drip. I felt amazing, but inside I was still

06:07

stressed and in this panic mode all the time. And it took me a while to recognize that the stuff inside of me was often different than the way other people saw me.

And it was different than frankly the reality of the situation which was, hey, I'm a successful entrepreneur. Why don't I feel like one?

06:23

The lesson here is that mental health matters. Don't let anxiety run unchecked.

Get help. Looking back, a lot of my anxiety came from trying to do everything myself all the time.

And that brings me to my next mistake, which was becoming hellbent on being a soloreneur. So, I embraced the solarpreneur ideal

06:39

and resisted hiring anyone for the first probably five, well, it wasn't quite 10, but 5 to seven years of my journey. That mindset can work if your ambitions are small or if you get really lucky.

But if you want to build something meaningful, you'll almost always need to collaborate

06:55

with smart, interesting, ambitious people. And it took me years to accept that.

The hire a bunch of contractors approach sucks because then your entire job is managing contractors. really hard to build something interesting with that approach to not actually have a team.

07:10

The challenge was I had worked corporate jobs for years and I didn't like my co-workers and so that experience made me want to avoid hiring cuz I wanted to control everything and that worked fine for small goals for these little apps doing 10 20 30 grand a month but it became a bottleneck when I wanted to

07:26

build a seven or eight figure SAS company. You may have heard me talk about task level project level and owner level thinkers.

I was dealing solely with task level contractors because I didn't want anyone to be relying on me and the more senior folks that I hired,

07:41

not only were they more expensive, but it it felt like I would have to do career development and I was going to be managing a team. And realistically, that's probably true.

But to do anything interesting and build great businesses, you need project and owner level thinkers, not just task doers. So the

07:58

lesson here is if your ambitions grow, so must your willingness to build a real team. I see it over and over and over across my 224 SAS investments and across the micro comp startups of the rest of us and this YouTube channel community.

08:13

In just a moment, I'll share the final point on today's list. A lesson I still have to remind myself even here on YouTube.

Before we get to that, if you're finding these insights useful, you'll probably enjoy the full Startup for the Rest of Us podcast episode where I dive even deeper into this list. Plus,

08:30

I have an additional six of my biggest entrepreneurial regrets. I can go a lot deeper into these items on a podcast than I can in a YouTube video.

So, if you want the extra stories and context that I couldn't fit here, head over to your favorite podcast app and search for Startups for the Rest of Us. You'll find

08:45

the full episode linked in the description below as well. All right, let's get to the sixth and final lesson.

It's that taking random internet opinions, including YouTube comments, too seriously, is probably a bad idea. So early on, I assumed anyone with a confident opinion online was qualified

09:02

to give advice. It sounds crazy, but 20 years ago, 15 years ago, it was my mindset.

And it took me years to realize that many of the loud voices on blogs, forums, and social media actually knew far less than I did about the subject. I gave their opinions too much weight,

09:17

especially when they were negative. These days, I know better and I brush them off.

Just because someone is loud online does not make them correct. Many strong opinions online are deeply uninformed.

And the challenge is that negative feedback can derail you mentally and strategically. So what I do

09:33

now is I curate who I take feedback from. Folks in my mastermind, advisers, investors, close personal friends, but I don't let internet randos dictate my direction or my self-worth.

And you shouldn't either. So the lesson is listen to trusted qualified sources and

09:49

ignore the rest. If you're early in your entrepreneurial career and you're not sure where to get started, go watch this video where I lay out the eight steps to building a SAS from scratch.

Thanks for watching. We'll see you next time.