How I Learned To Stop Viewing Myself As A Hero
A Tale of Two Companies
I was talking with my brother over lunch the other day about how different my new company feels from our previous one. At the old company, where I was a founder and he was an employee, everything felt like we were “clawing up from the bottom.” Our larger competitors were so well funded and had such great industry contacts that their success seemed inevitable; ours not so much.
But I told him that I was happy that at this new company it didn’t feel that way. I feel like we are the big, well funded company that is destined to succeed1.
At the old company I so felt like we were an underdog that it became a stated company value that we always wanted to “punch above our weight”. At this company I told him it felt nice to not have that weight attached to us.
Even on a personal level I just felt like, as an entrepreneur, I just didn’t belong in the room with some of the guys I was competing with. Not so much now.
The Hunger That Drove Us
He shared one viewpoint on this series of events, which was that the success of that company was born out of this kind of pain and desire to accomplish something, that there was a relationship between the two. And that maybe that type of pain would appear here at this company again and it would be interesting to see what growth that would bring.
I paused and thought about this for a bit. He acknowledged that this was just what occurred to him and I, of course, understood that.
Finally I responded and told him that I don’t think that’s the case. It wasn’t about the pain driving success – it was about how that pain had shaped my view of myself and what I thought was possible.
I realized that really something fundamental had changed in the way I viewed myself; or more importantly felt about myself.
Breaking the Solo Founder’s Curse
When I was starting the previous company, I remember talking to my colleagues at work about these tech startup books we were all reading. I had been so excited to have people who seemed to share a vision with me. But then I remember the day I actually decided to take action and how apparent it became that, while they really liked the ideas, they really just liked talking about the ideas, and weren’t going to do anything to bring those ideas into reality.
In a way that made me feel unique; but it also made me feel alone. I was starting out to do something nobody else I knew had done.
At this company, by contrast, though, as I started to get the entrepreneurial bug again, I did what I often do; I did some research, decided what I wanted to build, built it, and before long it was time to turn that product into a company (which is really just code for it was time to pick up the phone and get some sales). As I approached that threshold, though, instead of just doing everything myself because I didn’t know what else to do; I saw the decision before me and considered it.
I could take one of two paths:
Path 1 would be to do what I knew and was comfortable to me; but also really sucked. That was to start another business as both the product owner and sales person (and tax person and on and on and on2). I knew where that led.
Path 2 was what I chose instead. In that moment, I recognized a belief that I subconsciously held which was that I was the only person who was going to work as hard as me (and was therefore deserving of ownership in the business). As soon as I recognized that thought, though, this time I recognized how short sighted it really was. There’s no doubt that I work hard; last week alone I put in four or five 12 hour days and the week before I definitely put in an 18 hour day as we launched our new website. But just because I don’t see someone in my immediate environment that has that same entrepreneurial hunger that I have doesn’t mean they don’t exist. I just needed to open my mind up to the possibility of finding that person.
The moment I made that decision something magical happened; a name popped into my head. And even though I barely knew him at the time, fast forward six months and we’ve just launched a company together.
That change in attitude and thinking, I explained, represented a movement within myself.
Patterns of the Past
Further, I reflected in real time that this idea and belief that had so driven me before; that I was a perpetual underdog, clawing my way to the top (and particularly the idea that I had to drag others up with me), was a belief that had actually been with me for a long time. And this pattern of seeing myself as the isolated underdog wasn’t limited to my business life.
The story I’ve sometimes told myself about my high school basketball career was that I, the unsupported leader, amidst a barrage of hapless teammates, led our team to our first two wins in 4 years. Looking back now, I see the parallel clearly – just as in business, I was trapped in the mindset of the unheralded hero. What a good leader would have done, I explained, is seen the unique qualities of each individual teammate and then worked like hell to make them successful and build a system that utilized all of us to our fullest.
To be fair, I did try to do this at my first company, IDR, and to some degree we found success, but really was still limited by my mindset about what was actually possible.
As I shared this reflection with my brother, it helped me crystallize how my perspective on leadership and collaboration had evolved. While his observation about pain driving growth had sparked this deeper reflection, I realized the transformation wasn’t about the struggle itself – it was about outgrowing the need to struggle alone.
Beyond the Underdog Mentality
My brother then reframed this in a different way again for me. He pointed out that rather than looking back at these experiences as bad things or bad leadership, I should recognize the fact that some of the pressure I felt was that I wasn’t meeting my own standards. I wasn’t at the level I wanted to be. And now that I’ve come out the other side of those experiences; I feel this sense of empowerment and that I can move from a different place because I’ve earned it. I’ve earned the feeling that I deserve to be at the big boy entrepreneur table every bit as much as the next guy.
At the end of the day, I’m grateful that in this new company we don’t have to operate out of a place of feeling like we need to earn our place at the table. We’re here and we’re going to make an impact. Something about that frees us to create a vision of what’s truly possible, rather than just fighting for scraps off the table. My brother helped me see that this isn’t about leaving behind the hunger that drove me before – it’s about channeling it from a place of earned confidence rather than desperate determination.
- You’ll forgive the language and understand that I use that phrase in full awareness that we’re not in fact destined to succeed, have many challenges in front of us, and face a very real chance of failure. ↩︎
- When I’m talking about wearing all the hats, etc, what I’m really talking about is how I viewed things at the inception of the company, which is where the seeds for the rest of the company’s future were sewn. I ended up with a co-founder in my other brother Jonathan and a team, which lightened my load considerably, but the seeds I planted at the outset were still with us. ↩︎
