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For the Weekend: 3 Takeaways from Startup Grind with Matt Gillin

Startup Grind quickly became, and continues to be, one of the staple events at Benjamin’s Desk. Dozens of founders and leaders have come through the space at 1608, each one bringing a unique perspective and many valuable takeaways. The Mahers, Jennifer, Mike, and Anthony, keep the interviews conversational but certainly don’t shy away from the more difficult angles of startups. This past week, Matt Gillin had some great stories about his current startup, Relay Network, but also some hard earned wisdom from his last startup eCount.

“Be Right 51% of the time and be right on important ones. Who to hire, when to sell...”

Matt didn’t shy away from the mistakes they made when building eCount but made sure to point out that being right all the time isn’t required. It’s more important to be right more than wrong, otherwise you probably have some learning to do, and above all being right on key decisions is what matters.

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“[A startup] is about dumping out the pieces and putting them together as quickly and efficiently as possible.”

Every startup is looking to solve a problem and, at times, founders can go into development think they A to B path ahead. This is rarely, if ever, true of course but Matt’s comment captures how we have everything we need at the outset. To capture the first version of any idea, any first product, a prototype or event pretotype is always possible. The hardest part is staying out of your own way. Don’t overthink or over complicate. Take the pieces you have and arrange them the best you can for the next step.

A good follow up to this is “Between a bag of innovation and a bag of efficiency [I’ll take efficiency] it won’t happen without efficiency.”


“Cold Calling is Dead” and “You have to go in warm in some way.”

Our favorite as it follow’s HubSpots own anti-cold methodology. Matt talked about calling and emailing CEOs from Yahoo to Microsoft during the the DotCom era. Back then, it worked, at least a little. With far fewer internet denizens and a far lower likelihood of getting random calls, directly contacting CEOs with a pitch might work. But now, just getting contact information is far more difficult and they are much less likely to take in a pitch if you randomly contact someone.

Your best bet, of course, is to find some way to warm up your introductions and for that, stay tuned!

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