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What to believe in as a founder?
Understanding my role was more than believing a new idea could be a new company
As a founder, I know I am betting on myself over anyone else. It is a fact that is self-evident. However, it took me a long time, about a decade as a serial entrepreneur, to realize that was not something I needed to prove. What I needed to prove was something deeper and more intrinsic, that I needed to believe in myself. It’s a subtle distinction, and I will break down these distinctions.
For the last more or less decade, I shifted my career from management consultant to more or less founder: founding team on two companies and founder of two companies. When I read Bo Peabody’s Lucky or Smart at the age of twelve, I knew all I wanted to be was a founder. However, I also found myself in a position where it took a long time to get there and start understanding what it took.
It’s not about the idea
It took a lot for me to jump to being a founder. I went to a good college with a strong record of sending students to Wall Street (notably Lehman Brothers, as Dick Fuld was a trustee). There were no jobs for my college’s graduates when I graduated. Luckily, my Computer Science lab partner’s older sister was a Senior Manager at Accenture, and months after I graduated, I found myself in Accenture’s IT Strategy practice. I was not the most successful consultant, but I did carve a niche that positioned me to work on the projects I wanted with people I admired. While it never felt like it, my career looked like a 10 out of 10 on the generic, unsolicited advice given to undergrads.
For me to do my own thing and leave the confines of a respected, comfortable firm, I thought I needed to jump to something that would be an instant success. Everyone thought of my career as a success. So, whatever I did next had to be better than everyone else thought. This was a trap! It led me to join and start companies that applied the Internet to a clever industry use case. It was what I thought I needed to be successful as a founder.
The reality was it created two problems. First, being a clever solution meant it was not intuitive and thus harder to market and sell. When people more experienced than me foresaw this challenge, their questions felt like they were questioning me. The idea became wrapped in my identity. It made feedback too personal and made me, at best, defensive and a jerk at worst. While my intellect and tenaciousness kept me from losing everything, it was not what I set out to do in the first place. Instead, I should have realized that I had an idea and some facts that led me to the idea. Then, whether or not the idea was accepted or rejected was simply a question of having enough information presented compellingly.
During last week’s Denver Startup Week and the weeks prior, I made a point to find more peers and talk with more founders. So many first-time founders fall into the same trap. I get it. My favorite part of starting a company is believing there is an opportunity that other people overlook. Finding such an opportunity takes creativity, intelligence, and courage. However, it is not the role of the founder. The founder’s role and value is communicating that idea with others in a way that compels them to change. Founders become more persuasive when they can collaboratively understand, address, and respond to feedback. For me, that is the forward-thinking that is compelling. The idea is just the start.
Validation (and the lack of it)
When I left my last company, it was the first validation that I was doing the right thing for my career over the last decade. My modus operandi is that I am all-in or not in at all. So when I left consulting, I invested the small fortune I made trading in the markets (i.e., my life savings) into learning what it took to become a successful startup founder. While I still have a lot to learn, the fact that the last exit was an exit showed me that I was on the right path.
Coincidentally, the financial aspect was not part of the validation I sought. My parents never understood my career because their careers were much more linear. One day after my exit from my firm, they invited me to lunch out of concern. We talked about the numbers of what I was negotiating in my buy-out, and it was the first time they realized, “Oh, good. Our kid was not wasting away pursuing fanciful ideas.”
This epiphany reflected my concern for myself. Hearing my parents’ relief validated my relief. Taking the risk to be a founder takes a lot of self-confidence, often founded in knowing that earnings could be made up later. However, I started to get to a point where making it up later felt less and less of an option: all my friends were married and started having kids. It was one thing to know that the externalities of being a founder (i.e., the experience with a lot of responsibility) would lead to more, better opportunities faster. Living and capitalizing on it felt completely different because it still meant getting a new, highly competitive job.
These doubts drive the loneliness as a founder. These doubts can only be divulged with the correct audience in the proper context. One of the best things I did when I pulled out of my driveway in the morning was to tell myself, “Get these thoughts out of your head. Put your head down, do your job, and build trust.” Believing it would work out if I just worked was the only thing that made this exit possible.
Growing to believe in yourself
There were a lot of chips on my shoulder when I moved back to Colorado from the Bay Area. My move was catalyzed by a friend dying in a speed-riding accident and seeing what an adventurous life he lived compared to my 100+ hour weeks at an autonomous car startup. However, there was a point in my last company where life became comfortable again, and I could reflect on what I wanted to do next.
At that point, I achieved all the goals I sought for myself. The company had 20 employees, and we were oversubscribed on a large round for the stage. I spent more time in the mountains and skied a ton! My volunteer work creating and running a novel backcountry skiing course allowed me to live out a childhood dream of being sponsored for skiing (Thank you, Arc’teryx). It also made me realize that I sacrificed so much to get to that point.
Coincidentally, it was also the first time I realized what I missed out on since I started this journey. It took even more reflection to admit that I would not have wanted to live differently. I had to accept that this was who I was and how I chose to live my life. Once I realized this, I knew, for the first time in my life, that the consequence was that I had to wholeheartedly believe in myself and be the person that I idolized.
Consequences that I am learning
Another way to describe the job of the founder is that they are the person who will make the company happen. This is why it is important for the founder to strive to be the person they idolize the most. In the end, it comes down to them.
In the past, as I described, I relied on being smart, chasing a big market, etc. Those external factors motivated me to work hard. The problem was that those external factors varied greatly and seeking them became distracting. Everyone will respond differently to the goal of a startup. This is normal because it is a new thing that has not been done before. The lack of historical data and the inability to predict the future means no one knows or could even guess the outcome. However, if the founder is looking for external validation, the response to negative feedback becomes reactive. Mentally, the thought becomes, “How can I convince this person that I am right?”
The problem with this tenacity is that it is very stressful and exhausting. It put me in the position, “Do I want to keep on grinding tonight? Or do I want to have a beer, watch a show, and hope I am refreshed in the morning?” The longer that stress was endured, the more frequent the latter was the choice.
Rather, owning the role and just trying to be the person who will move people changes the whole dynamic. The motivation becomes more curious and objective because it now says, “I want to work in this space. What do you think?” Feedback becomes data rather than criticism. It turns the ocean from something to boil to something to explore. There are countless clichés that preach this mindset. However, few, if any, are blunt enough to say it all comes down to whether or not the founder believes in themself over anyone else.
For me to own this now, means that I have something to hold myself accountable. From personal things like fluctuating weight and going on and off diets to just losing it because I want to be the guy who looks slim and fit. When leading a team, it’s having the mindfulness to think from the third-person perspective, and not giving in to the emotions of a situation. Then, when a deadline looms, it becomes easier to turn down other social engagements and work late. There is no secret to owning this responsibility to be that person, but it does take an uncomfortable amount of confidence and belief in yourself.
I became a founder because I wanted to build something new and impactful. In my journey so far, I learned that it is not my ideas or will that are impactful but who I am. Faking it until I make it is not about faking being the CEO of a new idea-turned-company until the company is successful. This is too hard and subject to failure: too many variables and inconsistencies exist. Instead, as I started my next venture, I shifted my mindset from trying to make a success to just trying to be the person I believe in the most until I am that person.