Relentlessly resourceful = Outreach.io

Paul Graham is one of the best thinkers and writers there is on startups. One of his many superpowers is concision: boiling ideas down to their essence. My favorite example is his two-word definition of successful entrepreneurs: “relentlessly resourceful”. He concludes that same post by writing:

“If I were running a startup, this would be the phrase I’d tape to the mirror. ‘Make something people want’ is the destination, but ‘Be relentlessly resourceful’ is how you get there.”

Outreach.io just announced a new $2.3M fundraise, led by MHS Capital with additional participation from Floodgate, Founders’ Co-op and Version One Ventures. This isn’t a big raise by Valley standards, but it marks the end of one long journey and the beginning of another for four of the toughest founders I’ve ever had the pleasure to work with.

The story of Outreach begins long before today’s announcement, with a failed YC S08 company called Team Apart. Gordon Hempton and Wes Hather were that company’s  co-founders, and by 2011 they were living in Seattle and working on some new ideas. I got to know them and soon offered them a desk at Founders’ Co-op, where our second Techstars Seattle class was also in session.

Around the same time, one of our Techstars teams was coming apart due to founder conflict. Two of the three founders, Manny Medina and Andrew Kinzer, chose to stay on in the program while their third co-founder did not. I introduced Wes and Gordon to Manny and Andrew and something magical happened. These two teams fused together and became one, not because of a shared vision — they didn’t really have one — but because they just loved working and playing together.

By the end of Techstars this combined team had chosen to attack the technical talent market with an offering called GroupTalent. I led a convertible note round for the company on behalf of Founders’ Co-op, and a year later put together a priced seed raise for the company with my friend Boris Wertz of Version One.

The team hammered away ferociously at the technical recruiting market for over two years, trying dozens of different product and go-to-market approaches along the way. They were fearless in their attack, willing to junk their entire product and go back to first principles whenever they hit a real dead-end. And they stuck together as a team, grinding through the hard times without ever losing faith in each other, or blaming one another for their challenges in finding product-market fit.

Along the way, the team learned a huge amount about how professional recruiters sourced talent — from the tiniest boutique shops to the biggest national brands in technical staffing. And they more they learned, the more they saw how similar high-volume talent prospecting was to the much larger market for large-scale enterprise sales: once a prospect becomes a lead there are many tools for qualifying and tracking that lead to close. But higher in the funnel the process was almost entirely manual, cobbled together by individual salespeople using sticky notes and Excel tables. There had to be a better way, and they were just the guys to build it.

But after two-plus years of tireless effort (at ramen wages), money was running short, and the team could have been forgiven for deciding that a radical pivot to an entirely new industry segment — plus yet another from-scratch product rewrite — was more than they had in them.

No fucking way.

The proof is in today’s announcement, but — like the rest of the company’s history — the successful transition from GroupTalent to Outreach.io didn’t happen overnight, or in a straight line. A successful fundraise is just a milestone on a long journey, and the most exciting chapters of this company’s story are still to be written. But if there’s one team in our portfolio that embodies PG’s “relentlessly resourceful” description it’s this one, and I’m proud to have been a witness to their journey along the way.

Thanks you to Gordon, Wes, Manny and Andrew for your friendship, partnership and relentless resourcefulness — you are an inspiration.