Coming of Age as an Entrepreneur

Well it was just a dream
Just a moment ago

I think back to the Winter of 2008-2009. SpeakerText was a few months old. I was still living in New York. The city was cold at night. It snowed like 2 feet in one day.

Back then, for all intents and purposes, SpeakerText was just me, just my dream. We had no hustler on staff. No hacker. No money.

I remember one night in particular. I had left a small meetup organized by what was then called the Blue Venture Community (aka BVC), Columbia’s entrepreneur group. Goddamn it was cold. I was cranking Biggie on the iPod, walking down 53rd St in midtown, huddling in my wool coat. The Bloomberg sign hung in the air above. One day, I told myself, there’d be a SpeakerText sign. One day.

Well, we ain’t there yet.

But we’ve come a long way. On February 1, 2011, we got our first office (see photo above). And then, about two weeks ago, I found myself at The Rosewood, a posh restaurant on Sand Hill Road. Swanson and I were there meeting Mikael Berner, one of SpeakerText’s investors. It was a strange, fantastic feeling. I wasn’t there to beg for money; I wasn’t there as “the help,” picking someone up in the ambulance; I was there as a CEO meeting an investor––not a prospect, but an honest-to-god man that had written us a check.

For the first time in my life as an entrepreneur, I felt like I’d arrived, like I was equal and not just another outsider trying like fuck to break in. It felt awesome.


Over Christmas, I shaved my mohawk. It started off as an accident. Normally, I would cut the sides myself, then let Swanson clean up the edges. But it was December 23rd and he had already left to see family. I was about to turn 30 and fly down to LA. Over Christmas, I was expecting to see a woman that, well… let’s just say I wanted to look good for her. I wanted to cut the edges as close as possible, and ended up creating a bald spot in the back o’ the hawk. This led to me shaving my head entirely.

I ended up letting my hair grow out. I even got it cut at an actual barber.

As it turns out, I’m not an outsider anymore.

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31 Replies to “Coming of Age as an Entrepreneur”

  1. “For the first time in my life as an entrepreneur, I felt like I’d arrived, like I was equal and not just another outsider trying like fuck to break in”

    Ha! What an unbelievable douche! No wonder you’re single. Tee hee! News Flash: New study finds women aren’t attracted to status-hungry blowhards. Relax homeboy, stop desperately trying to prove something, you’ll get a lot more dates!

    1. Honey, thanks for the feedback, but dates are not something I have hard time finding.

      Having something to prove is what makes you endure the shit it takes to be an entrepreneur.

      Besides, it’s DB’s like me that build the companies that give jobs to people like you…unless you’re in the non-profit sector, in which case it’s DB’s like me who create the wealth that you leech off of.

      1. agree with you re: the entrepreneurship part Matt, but be careful when it comes to bashing non-profits. Even though I’m not in one – they can (not all, mind you) create a tremendous impact on the world. If you haven’t yet – study Pierre Omidyar’s Venture Philanthropy. Money is very very important, but money without impact is useless. There is room for both sides.

        Anyways, congrats on your success, your story is one of pure hustle. Keep it up.

  2. Congrats dude! Sounds like SpeakerText has upgraded from scrappy to lean. Sad to hear that mohawk is gone!

    Now that you’re funded, do you have any golden nuggets to share about the solo-founder, scrappy startup phase? Did you spend time on things that were a waste in hindsight?

  3. If you’re an entrepreneur and you’re not feeling this post, then you’re doing it wrong. Part of becoming a successful entrepreneur is transforming from an outsider to an insider. That transformation is validation for all of the hard work put in, self-doubts, and outright defiance of the dream-killers and detractors you met along the way.

    Good work Mark…

  4. Dude we met at one of those tiny BVC/CVC events! Even earlier than you are talking about, must have been early 09… Todd Spitz and Lauren Gilchrist and I think Dave Whittemore were there and somebody named Zeke was talking about starting a specialty chocolate company and we shot the shit over beers and burgers after and then everybody walked home having exactly the same experience you did. Love this post.

    1. I remember that night well. We bummed around until we could find an open bar in midtown to keep the startup chat going. Congrats Matt! Though I’m pretty bummed to hear the hawk is gone.

      1. Christian, I think that’s the exact night he was referring to. It was an incubation event, the one with that Lady Charmaine Day woman who talked forever about starting what was basically a religious cult. It was my first or second BVC/CVC events ever and one of the first times I felt like I was really connecting with others in the startup community—it’s all still surprisingly vivid in my mind.

        After the bar, I remember talking with Matt all the way back to my apt. on 53rd st.—we were both still very much high on “startup dreaming”-inspired adrenaline. It took us a long while talking before we finally decided to part ways. Makes me wonder if this immediately preceded Matt’s “Bloomberg Sign Sighting” while walking across 53rd st.

        Matt — glad to hear your doing well and currently on a high note. I’m sorry to hear that the hawk is gone, but I hope that good impressions were made with that lady-friend! 🙂

      1. Knew it! Memorable times and fun that you all remember too.

        Keep killing it buddy, it is awesome to hear. Next time I get to Cali I will hit you up to see the office and get a beer.

  5. lol “For the first time in my life as an entrepreneur, I felt like I’d arrived, like I was equal and not just another outsider trying like fuck to break in.”

    inspiring shit, and your email to CVC yesterday says it all !

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