Optimize for authentic relationships, not bluster

I'm sorry that I missed yesterday's Glamour Magazine panel on women in tech--if nothing else because it featured two of my favorite women in technology, Hilary Mason and Kara Swisher.  They're awesome and I'd show up to hear them speak anywhere.

More importantly, I know them both for a while--Hilary since August of 2007 through twitter and, of course, getting to work with her at Path 101, and Kara since I used to e-mail her about her Boomtown columns in the WSJ over ten years ago.  I even got her to come speak at Fordham while I was still in college. 

Both of these women had a significant impact on my career.  Kara helped foster my interest in the business of technology.  I followed her writing and bought her AOL book back in 1999.  She helped inspire me to start writing about business and form a business newspaper on my college campus.  My first article for the monthly edition was on AOL.  Ironically enough, the second nudge she gave my career also had to do with AOL--ten years later when in 2009, she introduced me to Jon Brod who was forming AOL Ventures.  I got to interview there and had a great conversation with Jon that inspired a post on the kind of venture firm NYC needed.  That's when I reemerged on Josh Kopelman's radar and he decided to offer me a job at First Round. 

Hilary has had both a major impact on my personally--by helping to push the envelope on the kind of data analysis work we were doing at Path 101.  When we hired her, we leveled up in terms of our technology and Big Data chops.  Just as importantly, she was an incredibly loyal and supportive friend and co-worker during really difficult times.  She also helped build up the ecosystem that I get to invest in through her work with hackNY and participation in NYC Resistor.  Yet, despite the impact she's had on my work, we met really non-chalontly through twitter.  I followed up with her on e-mail about her interest in coding up a little RSS related side project I was thinking about and we stayed in touch.  Six months later, she was accepting a job from me. 

The point I'm trying to make is the importance of building authentic relationships based around interests, not personal goals, over the long term.  That's how you win out in the venture and startup world.

It concerns me when I hear stuff like this:

"One of the audience members, Kathryn Minshew of the website The Daily Muse, raised a question about the amount of “bluster” among men in the industry. When she started to ask whether women need to “get more comfortable being . . . aggressive,” Swisher jumped in to finish the question with “liars, yes” (much to the amusement of the audience).

Kidding aside, Swisher said, “dudes in Silicon Valley” do seem to have no trouble playing the game and picking up the inside lingo of pumped-up valuations and venture capitalist name-dropping."

Don't get me wrong.  I get it. It may seem, in this environment, that the people who are successful get there by lining up as many big names as possible and having the "man parts" necessary to ask for utterly ridiculous valuations or to create slides with astronomical projections around taking over the world.

Are there examples of that?  Sure.  Does that make it a viable strategy for every new entrepreneur?  Not in the slightest.

When someone comes in to pitch me, I always ask them to tell me the "origin story".  How did this startup come to be?  Did you analyze the market and see an opening as if this was a management consulting exercise or are you passionate about it based on some impactful life experience?  I want to know who you were before you were an entreprenuer and how this new concept reflects and embodies that. 

Call it simplistic and naive, but being who you are, in my book, is always a winning strategy.  I was just some clueless kid when I asked Kara to come speak at my school and was even more clueless about data structures when I got Hilary to come work for me.  Both, I assume, recognized the authenticity around my interests and that's why they helped me out--not because I acted like some big swinging dick.

And that's not because they're women either.  Time after time, I've learned that the more I turn up the bluster machine, the more likely I am to rub someone the wrong way and have the friends that know me best say "You're better than that--that's not who you are."  My career has been driven forward by authentic relationships.  People I worked with and knew well funded my startup and the people that knew me best have always stuck up for me when my bluster got me in trouble.

Venture capital isn't a game or club any more than any other industry is.  If VC is a club--so is media, politics, the movie business--hell, any industry where the bets are on people, because people clearly work with others they like, have connections to and work well with.  Building up your network of trusted relationships with people willing to go to bat for you isn't a game--it's a way of living where you decide that community participation is better than trying to be some kind of solitary hero who doesn't need anyone.  You recognize the value in collaboration over selfishness.  You can call it a club when I share a deal with the last three people I worked with because I thought they did a lot for my companies, but I call it trust.

And trust doesn't come easy.  It takes time and authentic effort.  That's why when you've quit your job and you're trying to raise money in the next few weeks, it's going to feel like the odds are against you no matter who you are if you don't have a quality set of relationships.  Try getting married in the next few weeks if you aren't currently dating anyone--it's going to be equally as hard.  That's the kind of relationship you're signing up for. 

In fact, you can get out of a marriage.  You can't force an investor to sell, so you're kind of stuck with them. 

I don't think it's a good idea to tell any new entrepreneur that there's a wall between them and success and the answer is that they have to huff and puff and blow down the door by talking yourself up artifically. 

One, I honestly don't believe that to be true.  I know there are lots of good, honest people willing to take the time to get to know you, help you with your company, and do what they can to make you successful.  Even if I can't fund you, that's the kind of investor I try to be everyday.  It's the kind of person I try to be everyday. 

Two, it makes people feel like they have to be something they're not to be successful.  When I was in college, I helped organize a spiritual retreat for business students because I could see how draining they found the fall recruiting process to be--having to constantly try to figure out who they needed to be to succeed.  That's one of the reasons why I love venture capital--because I've gotten to work with a wide range of entrepreneurs taking their own unique paths to success--from a mom who spent 15 years in the jewelry industry to two hackathon winners trying to leverage community to break the yoke of costly legal overhead for small businesses.  They're all succeeding on their own terms--and they got there by building great relationships and participating in the professional communities around them.

To that end--to helping up and coming female entreprenuers build better relationships--I'll be holding a monthly lunch for a small group of women at the helm of promising young companies to get to know investors in a casual setting.  Later this month on the 28th, my co-hosts will be Marissa Campise and Sarah Tavel.  If you know of a newly minted founder whose network could use some additional investors, please make a suggestion in the comments.  We won't be able to accomodate everyone, but I hope to have 6-8 entrepreneurs join me and different investor co-hosts each month.