Committing to Risk. Stop Being a Coward. Just Jump.

To read the Green Pants Chronicles from the beginning, click here.

Act 1: Inception

All You Do Is Talk. Stop Being a Coward.

At some level, I owe the entire entrepreneurial journey to friend and fellow entrepreneur Adam Covati. I’d worked with Adam and Eric Boggs at Bronto, and they’d decided to turn a URL shortener that Adam had built into a full fledged Social Media Management platform called Argyle Social (refer to #UNCArgyle… go Heels!), and they were living the dream. High growth, excited customers, venture capital, white-knuckled fear of the velocity they were traveling… the whole enchilada. I was so hungry to do what they were doing. (As an interesting aside, I said as much to them about joining their efforts, and they both thought I was kidding, so a follow up a conversation never happened. Ah, what might have been…).

At any rate, Scot Wingo had created a StartUp Showcase at the ChannelAdvisor Catalyst annual user conference, and Argyle Social was one of the young companies selected to showcase their solution. The conference was being hosted at the Washington Duke (pretty swanky, with a nice golf course), and Adam, Eric and I were enjoying a beer on the putting green just outside of the restaurant. I was headily discussing BuzzBox, RFMConnex and about six other ideas.

And then, Adam dropped a load of bricks on me. “Matt, you have a bunch of great ideas, but when are you going to actually quit your job and do something. Stop being a coward.” He actually used an unsavory word that I won’t repeat here, but man did it hit me hard. I laughed it off in the moment, but my head was reeling.

I’m Afraid That I’ll Wake Up One Day and Never Have Been More Than A VP for Someone Else

My wife Laurie will tell you that I’m one of the hardest and deepest sleepers around (don’t ask her about the snoring… sheesh). I’m out like a light the moment my head hits the pillow. But not this night. I tossed and turned, and finally she said “what’s going on?” I recounted the story for her, and then laying there in the darkness, said “I’m afraid I’m going to wake up one day when I’m 60, and never have done more than be a VP of Sales in someone else’s company.” There’s nothing wrong with that…. It’s just that I really, really wanted to be an entrepreneur, and unless I jumped in with both feet, I would always just be that guy with ideas.

Laurie, to her credit, whispered that if it was that important to me, that she’d go back to work so that I could quit my job and make a go at it. So that night, with Laurie’s support, I decided to leave the safety and security of Bronto and make a run at it.

At Some Point, You Have to Decide: Just Jump

I started this series with the goal of just capturing the story, and not boiling it down to platitudes. I’ll keep faith with that mission, but here’s something I learned that is probably worth passing along. There is some very finite point in every entrepreneur’s journey where there’s a seminal, terrifying, and wildly freeing moment in which you decide that you’re just going to jump, damn the consequences.

This was my moment. Laying on my back, in the darkness of the early morning hours, with my mind racing and my heart thumping…. I decided to just jump. It was different than planning, or contemplating, or considering. It felt like the same thing that happens when you jump off a cliff into the lake below… you fret, and think, and shuffle, and then suddenly, the moment of abandon hits you and off you go.

Actually Jumping

I don’t remember the exact timing, but having made the decision, I started to set my affairs in order to make this happen. I reframed our budget (which Laurie and I later called the year of boxed wine and beans and rice). I did an assessment of all things that would potentially throw me off. I set up every medical, dental and eye appointment I could think of so that I could square it all away while I was still insured (and “ensured” so to speak…. That if I discovered something, I’d be able to ride it out while I was still employed at Bronto). I’ll spare you the gory details, but let’s just say that if it could be poked, prodded, cleaned, updated, or examined, I had it done. I was all clear and ready to rock and roll.

In about mid-November, 2010, Chaz Felix (Bronto co-founder) and I went for a walk and talk (something that we did often and which I enjoyed doing with him) and I shared my decision to leave Bronto and start a company. He respected my need to try because he’d felt that call too, years before. With that conversation, I was committed. I would enter January 2010, recklessly unemployed, with a catastrophic insurance plan, no salary and no full commitments from my team to follow me off the cliff.

And I was as excited and free as I’d ever been in my professional career.

In my next post, I’m going to briefly discuss the rationalization of the risk, because it was an important part of the decision.