Today marks exactly a year since the first time I ever pitched a VC in my life. How do I remember? It also happens to be my Birthday. The victim was Bryce Roberts, and to this day, I still apologize to him for having to deal with my shitty pitch.
What a difference a year makes. It feels just like yesterday I finished up that informal meeting. Its one of my most vivid memories from the past year. We finished talking, I helped hail a cab for Bryce, and then rushed to grab a cab for myself so I could trek uptown to a special dinner date my wife had planned for my Birthday.
It turned out to be a surprise birthday party with some of my closest friends…. what an amazing night it turned out to be.
Fast forward one year to today. Once again, it was my birthday, and as with birthdays go, you can’t help but pause and reflect on what has changed over your lifetime and most importantly, what has changed in just one year. 365 days later, countless investment pitches later, after raising a round, building a team, growing a product, losing a team, rebuilding a team, and keeping on keeping on, here are my reflections from 2011.
Looking back on 2011
These days, I have a tough time remembering the actual year we’re in. It still feels like last year was 2009, except its 2012, and 2011 was probably one of the most transformative years in my life — even though when I reflected on 2010, I said the same thing.
In 2011, I stopped doing a whole bunch of things:
- Stopped working on Braintrust, the group collaboration tool that was supposed to kill email.
- Stopped working on Main Street, the instant web site builder for small businesses.
- Stopped my consulting business and all projects that came long with it.
- Stopped doing my weekly podcast.
- Doubled down on Tout and decided to put all my heart, soul and sweat into making it a real business.
- Wrote a blog entry about how Tout came to be and won a whole bunch of stuff.
- Joined the 500 Family.
- Raised $350k from Esther Dyson, Dave McClure, Eric Ries, Venture51 and some more seriously awesome angels most of whom have proved to be seriously awesome mentors.
- Built a team around Tout, lost the whole team, and then started to rebuild the team once again.
In 2011, I also truly learned what it means to be completely consumed by ONE thing: I kissed my wife goodbye, said goodbye to my friends and moved from New York to Mountain View for the summer accelerator program. I was even able to convince a friend to move for the summer and join Tout. It was an amazing and intense few months and it followed a few months of being completely burnt out which made me question whether it was worth it in the end.
Ah and also, In 2011, my wife and I made the decision to pack up our lives and move to San Francisco. Therefore, I moved Tout and the entire business to San Francisco as well. And with that, I moved to rebuild the entire Tout team in San Francisco as well.
And finally, in 2011, I took something that started off as a simple weekend project to solve my own problem and turned it into a real product that thousands of people use to run and grow their businesses in amazing ways.
Lessons Learned from 2011
2011 was an intense year of growth, learning, joy, thrill, FUN, and pain.
Everything they say about Entrepreneurship is true. It takes you through the highest of highs, the lowest of lows, and tests your courage and challenges you at every single moment. If you’re going to do this, think twice, and then grab on to something that can ground you — because it is going to be an intense ride.
If you aren’t having days where you start off with “What am I doing with my life?!” peak the day with “Holy shit, we’re going to be a billion dollar company” and go to bed with “God, there’s so much to do, please help me” — then you’re probably doing it wrong.
With that said, I think the single biggest lesson learned from 2011 for me is to learn to be more self-aware: As you take on bigger challenges, and bigger goals, and grow your team, it always becomes inevitable that your own voice, your own gut, and your own instincts start to get drowned out compared to all the other (sometimes more experienced) voices. Don’t let it. The biggest mistakes I made in 2011 stemmed from my failure to stop and hear my own voice. If you feel pain, figure out why. If you feel overwhelmed, hit the Pause button (force it).
Figuring out the perfect balance between being open minded, self-reflective, and confident is the secret to being a great Entrepreneur. And its one balance that I plan on continuing to perfect in 2012.
Looking Forward to 2012
It takes 3 years for a startup to become an overnight success. Each year brings its own set of challenges but the goal stays the same. So unlike previous years when I had a full on game plan on how the coming year would be different, this time around, its really more of the same.
I plan to continue to focus on two key things in 2012:
- First and foremost, continue to grow ToutApp into a truly awesome business, and,
- secondly, continue to contribute and advance the art of Entrepreneurship by sharing my learnings.