I’ve spent the last 12 years investing in category-defining companies. By “category-defining,” here’s what we mean: I’m talking about companies that are on track to reverse type 2 Diabetes in 100M people, companies that give database a new name, companies that empower consumers in their relationship with their credit and loan provider, and companies that give homeowners the freedom to move.
At Caffeinated, I’ve invested in exceptional entrepreneurs. But now, I want to invest in you, too. I’m excited to announce that Caffeinated is growing: I’m looking for two investors to join our early stage investment team — this is truly an investor role. You’ll make the calls, you’ll cut the checks, you won’t need permission. You’ll be my partner and I will work directly with you, and impart everything I’ve been fortunate to learn, as you will be responsible for investing $20M into 30-40 startups over the next two years. You’ll be carrying forward the legacy of Scout Funds I (2016) and II (2017), which are currently generating a blended net IRR of 55% and a gross MOIC of 3.7X. I don’t doubt for a second you’ll carry an even brighter torch with Fund III. The Scout Fund portfolio to date includes: Anchorage, Bitwise, Clubhouse, Culdesac, Deel, Divvy Homes, dYdX, Heracles, Highlighter, Homebound, Jobox, Lambda School, Loft, Lunchclub, Mercury, Notion, Pulley, Run the World, Runa, Spring Discovery, Swiftlane, Threads, and Whisper.
This role might be a good fit if you identify with Caffeinated’s core values: you hustle, move fast, have good taste, listen, and are humble. At Caffeinated, we’ve come a long way because we embody our values with rigor. At Caffeinated, we collaborate with founders from the very beginning, betting on them, standing by them, and supporting them intently through their journeys. Just like the flavor of every pour over is determined by subtle choices — the climate in which the beans are grown, the soil acidity, how the beans are roasted, ground, and served — so too do we distinguish ourselves by teaming with founders early and emphasizing the importance of every subtle choice in our craft.
You recognize that while it’s tempting to come up with new adjectives or descriptions to create novelty, or flair, around what you do — all that actually matters is how you do it. All that matters is the verbs. And while there are only a few verbs in this business — to hustle, to preempt, to endure, for instance — there’s a distinct way to do them.
At Caffeinated we have broad values, but a specific understanding of what they mean to us. When we say “we move fast,” we mean that we mentally committed to the founders of Loft within two blocks of a walk together, and verbally by the time our walk ended, not even an hour later. What “high integrity” means to Caffeinated is that a deck from a competitive company gets forwarded to the trash, not to our portfolio founder. “Hustle” is the word we use to describe the way we’ve raised debt capital for portfolio companies in less than a week, based on a single document, in a process that would’ve taken a bank/debt fund months. “High conviction” is the confidence with which we teamed with Howie Liu and Andrew Ofstad and invested in every round of Airtable since inception, stepping up to lead their Series B when no one else would.
As long as you embody, with distinction and vigor, the values we listed above — and have 2-4 years of experience working at a startup, tech company, or in finance — you could be a great fit. And if you work well independently, bring an original, existing network (e.g. ex-Shopify, ran the Georgia Tech ACM Programming Team), put people first, take care of others as well as yourself, are solutions-oriented, and kick your ego to the proverbial curb — then you could be exactly who we’re looking for. We’re not looking for a brand name school on your resume. We’re not looking for someone who synonymizes this opportunity with Twitter clout. We’re looking for someone who plays long-term games — meaning, you believe in an exceptional founder even if their first endeavor fails.
We’re looking for aggressively open-minded individuals. What does it mean to be aggressively open-minded? Well, have you ever put some real elbow grease into unscrewing a tight glass jar? Our minds are usually screwed shut the same way — but all the best ideas, and opportunities, are on the other side of the vacuum seal.
You will be Caffeinated’s newest investment partner. You will build unique deal flow, source startups, invest in startups, support the portfolio, and build your own investment track record. And in return, I promise to invest in you. I promise to help get you to where you want to be next, the way I do with the companies I invest in. After your 2 year run, I imagine your possibilities are limitless: you could run Caffeinated Scout Fund IV, start a startup, join a portfolio company, start your own venture fund, become a General Partner at another top-tier fund. You could do something else exceptional. Something category-defining, no matter what sort of category you choose.
I can’t wait to meet you. Fill out this form and we can start a conversation.