Reflections on Overnight Success

Today Seattle fintech unicorn Remitly (NASDAQ:RELY) begins its journey as a public company. This is obviously a huge milestone for the founders, not to mention the 1,600+ employees who have joined them along the way. It’s a different kind of milestone for me as an investor: 10 years ago I led the company’s Seed round and joined the board, where I served until the Series C. Today marks the first time in my investing life that an investment I led at Seed has made it all the way to its Wall Street debut.

I know this is a familiar experience for many of my peers in Venture Capital. And 10 years is a long time to wait in any career before achieving an important milestone. But for me, and for the investment partnership I co-founded, it still feels like a moment worth celebrating.

Today I’m feeling both lucky and grateful to have met the founders of Remitly when I did. Matt, Josh and Shivaas helped me learn early in my VC career what good really looked like. Not for their feats of “blitzscaling” or similar startup hype-factory nonsense, but for exactly the opposite: for methodically building a product and a culture that delivers real value to real people, with genuine care for the humans involved, fused with a relentless desire to get better every day, no matter how many days it takes.

Every founding team is unique, but my journey with Remitly, beginning as early as it did, helped me to see the raw excellence hidden in those that came later, from Outreach and Auth0, to Bluecore and Amperity, Ally and Level Ten Energy, Shelf Engine, Routable, Comet ML and a dozen others whose names you haven’t heard yet (but I expect you will). Along the way, I had the incredible good fortune to team up with a founder from our first fund — Aviel Ginzburg — as my investing partner. Our shared decade-plus as investors in over 250 companies — both as VC partners and in our roles leading Seattle’s Techstars programs — has built a foundation of trust, experience and craft that makes even our bad days good, and our best days better than “work” has any right to be.

The world of software investing has changed dramatically since we started Founders’ Co-op back in 2008. Things that seem obvious now — the collapsing cost of starting a software company, the corresponding ascendance of Seed (and now Pre-Seed) as the first institutional funding stage, the steady erosion of Bay Area dominance in company formation and the related rise of new centers of excellence in Seattle, Austin, New York, LA and beyond — all of these were unknowns when I began my journey as a venture investor.

I fell in love with the Internet back in 1993 and spent my first 15 years as a founder/operator, creating and launching Patagonia’s first online store, bootstrapping an ecommerce software startup to $15M in revenue before selling it to a public acquirer, co-founding — and failing at — a venture-backed startup, before switching roles to help other founders as an investor at the earliest stage.

The ‘aha’ moment for me came after moving back to my hometown of Seattle after many years in California. Founding a company here, even with the support of local and Bay Area VCs, was ten times harder than bootstrapping my first company in San Francisco had been. From raising money, to attracting great talent, to finding a local peer group of high-performing founders, building a startup in Seattle was frustratingly, unnecessarily hard. In a market so rich in engineering talent and an incredible — if concentrated — history of tech wealth creation, that seemed like a problem worth solving.

Like any startup journey, the years have been short but the days long. As a self-taught VC I learned my most important lessons the hard way. And the most enduring lesson of all is how long it takes to build anything of real value, whether it’s a company, a venture firm, or a startup ecosystem.

The venture industry values speed above all else, but today I know that every story of overnight success you read in the trades has been carefully pruned and compressed to create the illusion that the journey was both short and wildly successful from the beginning. Not only is that a misleading and disheartening lie to first-time founders, it dishonors the grit, craft and resilience of those few founding teams who do make it all the way to the public markets.

Ten years later, Seattle is still mostly a company town, where big employers like Amazon and Microsoft dominate the talent market and founders have to be twice as capable, persistent and resilient to raise their first institutional round. I still feel like an outsider in the very insider-y business of Venture Capital. And I still have so much to learn. But today I’m feeling grateful for my amazing investing partner, the extraordinary founders we’ve backed along the way, and all we’ve learned and done together that has brought us to this point. Go Remitly, and thank you Matt, Josh and Shivaas.