I’ve started a company company!

Frustration is the better mother of invention so 18 months ago I backed Ben to start Union. Mostly it was to shut him up. Ben is Thinkful’s former Head of People where he scaled us from 30 to 130 FTEs and played a critical role in our acquisition. But he spent 2020 complaining that the companies he was excited to work for were headed toward avoidable mistakes without the will to avoid them. For my part I had just left Chegg and was heading for some lived-through-M&A-and-integration-worked-full-time-since-2004-about-to-turn-40 time off.

My time off really was mostly time off: building a woodshop, traveling, all that good stuff. But backing Ben was so rewarding I found myself repeating it two more times with two other underappreciated founders, supporting two non-profits (Donate to Child Advocacy! Donate to freeCodeCamp!), advising and/or investing in 20 Seed to D-stage companies, and trying but failing to get excited about crypto.

Union is a recruiting firm that gets companies to hire better, retain longer, and manage performance without bias. Because of Ben in 10 years no one will hire in-house HR. I’ve backed him with early customer intros, a budget in case it wasn’t quickly profitable, and a promise to collaborate on how to grow.

The last 18 months taught me something stupidly unexpected: There’s boundless fulfillment in helping someone else succeed. That’s weird, right? Have I mentioned I was the CEO of Thinkful, an entire school based on mentoring? Yes, well, perhaps Ben, Blake, Parniyan, and Arlyss have just shown me how to mix co-founding (which I’ve loved since 2009!) and mentoring (which I fell in love with thanks to Dan in 2012!) and investing (which is nearly criminally not time consuming…).

Which brings us to starting a company company. Three days a week I’m now working as a co-founder on three companies under the arbitrarily named holding company “503 Corp”. Union is profitable, growing 10% monthly, isn’t saas (yet) and as a result can’t yet be a monopoly (and so isn’t yet raising money). The others are earlier, but like Union, need to exist. Aside from their great co-founders, each share a belief that companies and careers will be better with fewer cost centers. Instead of reluctantly hiring cost center FTEs then slowly integrating software together, companies by 2030 will hire great experts that come bundled with best in class software that can be piloted cheaply, turned on quickly, and scaled endlessly. 503 is testing where that thesis proves most true. Put another way, 503 is creating companies like Pilot, which already bundles bookkeeping with QuickBooks. Union is Pilot for HR, the second company is Pilot for FP&A, and the third, GoodGig, is Pilot for subcontracting.

My other days are spent researching, maybe another company, we’ll see.

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Darrell Silver

Launching companies with undiscovered founders for 503 Corp. Co-founded+CEO’d+sold Thinkful (acquired by Chegg) & Perpetually (acquired by Dell).