December 22nd, 2019

I don’t have any regrets about career choices as they were deliberate, well-intentioned, and rewarding. I think it’s been 6 hard years of risk-taking and independent thinking. That said, I haven’t accrued the professional momentum, benefit-of-the-doubt, and positive association that I largely think my fundamental bundle of skills, contributions, and inputs ultimately could warrant.

That’s just how the game is played. Brands matter. Momentum matters. Everyone has limited information. Everyone has limited time. Assumptions and associations have to be made from afar…hot take or resource constrained. Business is business.

I’ve had and tried to deal with that insecurity for the last few years. Why write in public, why have a rich digital surface area, why develop modern friends, why invest deeply in friendships, why ship side projects, why start angel investing, why travel to the west coast just to work remote…because no one really knows “Ryan” for being at X, having started Y, or joined Z early. People only know Ryan for what I’ve thought, written, and the time we’ve actually spent together (ketch/coffee/dm) .

I don’t blame them. 1st employee at Blank Label, 1st non-technical Wildcard, 1st-PM Clarifai, and co-founder at 2121/Jumbo were all great adventures that have made me the product-minded business athlete I am today. Just not adventures that you see in a bio, read about in a 30U30, or hear on a podcast and think ooo000 damn, :smash follow:

That’s all to say, I now am a small part of a larger company and brand that many people in my world know of, respect, and even rely on. It feels good, it really does. I feel like there’s tailwinds for every bit of energy and time I invest into my role and larger team’s success. It feels good to be part of something that’s working on a fundamental level…classic PMF, real biz, differentiated value, etc.

🏈

I am always puzzled when running backs don’t seem to remember who blocked for them. They’ll punch in a short TD run untouched a few yards out from the goal line and immediately start beating their chest in a fan-facing celebration.

They don’t seem to realize that five hundred other running backs across college, the League, or even in recent retirement could’ve made that same play and it was 95% determined by the fact that their right guard, right tackle, and tight end blocked the shit out of 3-5 defenders. Raw strength and tactical execution by their teammates created a hole for a small bus to fit through.

Yes, visually pump up the atmosphere and stadium to regain momentum back in the game. But just know, their work and sacrifice is the thing that got you 6. And maybe immediately go over to dap them up.

I’ve never felt more well-aware of those who block and have blocked for me at Segment. 7 years of risk-taking, hectic launches, long nights, crappy conference travel, lost deals, small wins, big wins, and stressful decisions give me and my other teammates a chance to win. To win in our role, team, company, and market.

Hug your blockers this holiday season.