I studied liberal arts in college, and was never much of a student. I didn’t apply myself, and I wasn’t passionate about or interested in the things that I was learning (or not learning). I was filled with pent up ambition and nowhere to channel it, and found myself partying in a futile search for excitement and fulfillment.
As I neared graduation, I had increasing thoughts of becoming an entrepreneur. I had business ideas racing through my head and was constantly coming up with the next one. Yet a fundamental problem existed - I bounced from idea to idea and I never tried any of them.
Fast forward ten years, and all of my experience since college was working in small, fast growing VC-backed startups: first in recruiting, then in sales, then in business development, then as a headhunter, helping VCs hire CEOs to run their technology portfolio companies. It was all great experience, and I always viewed it as ‘practice before the big game.’ I ALWAYS planned on being an entrepreneur. But my ideas were never ‘good enough’ and I never though I ‘was ready’. As I liked to say at the time, I was a serial entrepreneur who was batting O for O, since I had yet to have a single at-bat.
Finally, the stars aligned for me. I found an idea that I couldn’t stop thinking about, in an area that I was very passionate about and had a lot of experience (and frustration) with as a user. It was also a large market that I believed was ripe for innovation in the years to come. So I went for it 2.5 years ago and started my first company. It has been hands down the best professional decision I have ever made, and I’ve never looked back.
As I sat (on this 7 hour flight with no wi-fi) and reflected on the last 2.5 years (and the last 34 years), I found myself thinking about what advice I would give to a 21 year-old me if I could go back in time. Here is what I’ve come up with so far:
Do what you love
Life is too short to toil away doing things that you don’t love and aren’t passionate about. If you aren’t feeling it, stop trying to force yourself to fit into a mold that clearly doesn’t fit. Instead, focus on putting yourself in a situation where you can be more excited and fulfilled. What are you most passionate about? What aspects of your experience around that thing you are so passionate about are frustrating to you as a user, and how could your experience be improved? I spent a lot of time focused on market opportunities rather than passion. While market opportunities and timing are important, there is nothing more important than passion.
Once you have figured out what you are most passionate about, don’t wait, do something! I spent years bouncing through idea after idea, and operationalized none of them. In hindsight, the most important learning doesn’t come from waiting for the perfect idea, it comes from the entrepreneurial process of taking an idea and working towards making it a reality. And the only way it will ever become a reality is if you try! As Wayne Gretzky likes to say, you miss 100% of the shots that you don’t take. Plus, even if you fail, you will learn more from the process of trying than you ever would from a ‘job’.
When you find an idea, your instinct may be to keep it under wraps so other people don’t copy it. I fell victim to this along the way, partially since I didn’t want people to copy my ideas, but more so because I wasn’t confident enough about them or about myself as an entrepreneur to share them with the world. When I look back, I realize that the difference between the one that caused me to ultimately take the leap and the others is that I flipped a switch; for the first time, I told EVERYONE what I was planning to do. Just the act of sharing it served as a powerful form of accountability, since now other people were watching. Plus, the day I started talking about it was the day it started transforming from ‘idea’ to something more. As I look back, if I had talked about more of my ideas along the way, real traction would have materialized more quickly, as would my skillset and confidence as an entrepreneur.
Listen to your gut
Along the way you will come across a tremendous amount of skeptics, who will insist that your idea is doomed. This will be true of any idea that you ever have, no matter how compelling it is. My advice is to listen to everyone, as feedback can provide powerful learning, but make sure to trust your gut. As long as your gut tells you that you are heading down the right path, then block out the noise and persevere. If along the way your gut starts telling you otherwise, only then is it time to take action. Just remember that every single billion dollar plus company that has EVER been built had just as many skeptics as you when they were starting out. The bigger the idea, the less people are going to get it during the early phases of development.
It’s OK to fail
I mostly covered this in the ‘get moving’ section above, but needed to re-emphasize again. IT IS OK TO FAIL. In fact, the faster you fail, the faster you will learn how to ultimately succeed. You can take all of the learnings from your failed venture and apply them to the next one. That doesn’t mean you shouldn’t try with all of your might to succeed, but you better not let fear of failure stand in the way of going for it. For me, not going for it would have been a massive failure, so I knew there was no other way.
Don’t go it alone
Birthing a company from nothing is really freaking hard. If you can avoid it, don’t try to go it alone. That being said, be extra careful about who you select for partners, as your team is a hugely important success criteria. When I quit my job I didn’t yet have a team, but my #1 priority once I left (and the reason I did so) was to focus full-time on finding the right team, since I knew how important it was to do so.
I will leave you with one final quote that I had hanging on my wall for many years before I finally quit my job to start a company:
“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood, who strives valiantly; who errs and comes short again and again; because there is not effort without error and shortcomings; but who does actually strive to do the deed; who knows the great enthusiasm, the great devotion, who spends himself in a worthy cause, who at the best knows in the end the triumph of high achievement and who at the worst, if he fails, at least he fails while daring greatly. So that his place shall never be with those cold and timid souls who know neither victory nor defeat.” – Theodore Roosevelt
I think that is all for now, young Jason. Now go out and get in the arena! And if you can avoid it, don’t wait ten more years to get started.