How To Make It as a
First-Time Entrepreneur

No One Wants To Play With Me

Vinicius Vacanti is co-founder and CEO of Yipit. Next posts on how to acquire users for free and how to raise a Series A. Don’t miss them by subscribing via email or via twitter.

I remember walking into my first NY Tech Meetup almost two years ago. I looked around and didn’t know anyone in the 120-person crowd.  After watching the demos a safe two seats away from the closest attendee, I approached someone and introduced myself.  They didn’t seem interested in talking to me and walked away a few minutes later.  After standing around for a few more minutes acting like I was looking for someone, I just walked out.  Ouch.

Two years later, that’s all changed.  I’m now a member of the tech community.  Don’t get me wrong, I get left out of all sorts of tech events (a painful experience of seeing the event get announced on Plancast weeks before and then getting reminded the day of, courtesy of Foursquare checkins).  But, more often then not, I make the cut and, when I go, I’m greeted by many friendly faces. I even get emails from people wanting advice on how to break into the NY tech community which is why I’m publishing this post.

Here’s what I did (like everything else in my life, it’s a logical series of steps):

1.  I realized it’s really important. I didn’t think it was till I had a couple of lunches where people completely changed how I was approaching my work (both on the product side and the entrepreneurial side).  I also read this crazy but brilliant book: Never Eat Alone.

2.  I set up social media profiles. LinkedIn is good and easy but Twitter is the really important one.  After meeting with people, Twitter was a great way to keep the connection alive as most people (including me) are thrilled and flattered whenever anyone responds to their tweets.  The other thing to do is set up a blog.  If you can do it, that’s awesome and it will be really helpful.  I never was able to keep up with it till more recently.

3.  I reached out to my existing network. I found all my existing friends who were in tech and met up with them.  I also asked them to introduce me to other people they knew.  This got the ball rolling.

4. I cold emailed / got intros to prominent young members of the community.  I met with community organizers (Charlie O’Donnell with nextny and Nate Westheimer with the Tech Meetup).  I also met with anyone who was seriously working on a startup.  Out of every five meetings, one will go nowhere, three will be good and one will be amazing.  I had amazing meetings with: Tobin Schwaiger-Hastanan, Fraser Kelton, Jonathan Wegener, Jon Steinberg, Jason Schwartz, Andrew Kortina, Nathan Folkman, Mark Davis, Eric Friedman, Bryan Birsic, Dave Ambrose, Justin Tsang, Greg Galant and a bunch more I know I’m forgetting).  They gave me advice that would have a profound impact on what I was working on.

5. I went to tech events.  The NY Tech Meetup is a great way to support your community and meet new people; but, if you’re not good at going up to people, you’re going to struggle.  I had more success at the smaller meetups like the NYC Lean Startup Meetup.  You should try to form a quick connection with someone and email them afterwards to set up a breakfast or lunch.

6.  I helped organize an event for founders.  This may have been the most helpful of all.  Jim Moran, my co-founder at Yipit, and I organized an “Entrepreneur’s Brown Bag” with DFJ Gotham.  Every month, 12 different entrepreneurs would get together at DFJ Gotham’s offices for a pizza lunch and we would talk about our challenges.  We no longer do it but, over a seven month period, we met so many awesome founders that turned into great friends.

7.  I joined Soccer 2.0.  I played a ton of soccer growing up and I found out about a tech team that played soccer (you wouldn’t think that’s the best way to put together a sports team but we actually ended up winning our division). Whatever your non-tech related hobby is, I’m sure there are other members of tech community who share it.

8.  I didn’t keep score. My goal with everyone I meet with is to be more helpful to them than they are to me.  I try to spend more of the meeting talking about their stuff than mine.  I try to give them advice / ideas and come up with introductions that might be helpful to them.  Trust me, it all comes back and way more than you would expect.  After I met with Chris Dixon, who was obviously way more helpful to me than I could be to him, I got back to my office and spent four hours going through his site Hunch and sent him a hundred points of feedback.

While it took a serious commitment, becoming a member of the tech community has been crucial for me.  I can honestly say that much of the success that we’ve had at Yipit (funding, product improvement, PR) can be attributed to someone in the tech community who was kind enough to help us out.

(Photo courtesy of Larry)

Vinicius Vacanti is co-founder and CEO of Yipit. Next posts on how to acquire users for free and how to raise a Series A. Don’t miss them by subscribing via email or via twitter.

Vinicius Vacanti is co-founder and CEO of Yipit. Next posts on how to acquire users for free and how to raise a Series A. Don’t miss them by subscribing via email or via twitter.

As a former i-banker, I struggle to overcome each of the following five shortcomings. I’ll write about how I’m dealing with them in future posts. But, the first step is recognizing you have a problem.

1. You have no useful start-up skills. You certainly didn’t learn how to program (cheap excel macros don’t count). But, it turns out that i-banking didn’t teach you essential non-technical skills either including product management, marketing or fundraising skills. You’ll need those skills, not just an idea, to attract a technical co-founder.
2. You hesitate to make uninformed decisions. In the i-banking world, you were taught to never make decisions without fully investigating the issue. In the start-up world, you are better off making 100 decisions with a bunch being wrong than 10 well-researched decisions.
3. You’re a perfectionist. When I joined The Blackstone Group, Steve Schwarzman, the company’s CEO, told us:  “99% right is 100% wrong”. In the i-banking world, you had to be perfect — the numbers had to tie, the formatting had to be consistent, and, above all else, no extra spaces. In the start-up world, you can’t afford to be perfect. You can only spend 20% of the time to get 80% done.  You don’t have time for the last 20%. As Reid Hoffman, CEO of Linkedin, said:  “If you review your first site version and don’t feel embarrassment, you spent too much time on it.“
4. You don’t network. In the start-up world, you’re told to never eat alone. But, in i-banking, you always ate alone at your cubicle. If you were lucky, you got to eat dinner with some of the other analysts in the conference room.  In the start-up world, you need to become a member of the tech community. You need to meet everyone because those people can help make or break your start-up with their support and ideas.
5. You’re too private. You spend hours adjusting your Facebook profile privacy preferences to make sure you couldn’t be searched. You never tell you friends about what you’re working on — you weren’t allowed to. You’re not a self-promoter.  In the start-up world, you can’t be secretive. You have to talk to you friends about what you are working on without making them sign an NDA (sorry to the people I did this to). They’ll completely change the way you are thinking about your project; they’ll make valuable introductions.  You need to start a twitter account and a blog. You need to become a self-promoter.

Fortunately, what you did learn on Wall Street was how to work incredibly hard and do 30 things at once. You just need to be aware that you have some new habits to pick-up and a few habits to lose. I’ll continue writing about what I did to overcome each of these limitations here and you can follow me on twitter. (see #5 for self-promotion).

Update:  Interesting post by Kate Huyett on 5 Things I Learned in Finance That Are (So Far) Helpful at a Startup

Vinicius Vacanti is co-founder and CEO of Yipit. Next posts on how to acquire users for free and how to raise a Series A. Don’t miss them by subscribing via email or via twitter.