Welcome to Rooted In, the Roots newsletter 🏡

In most editions, we'll spotlight people, cities, and companies building outside the usual coastal hubs. But Edition #1 is about us. Why we built Roots in the first place, and the opportunity to accelerate network effects for outlier entrepreneurs.

Join the waitlist today.

Event Recaps:

Upcoming Events:

Over the last five years, I've met with more than 5,000 entrepreneurs while building Redbud VC from mid-Missouri into a nationally known fund. One conclusion: talent is everywhere. Network connectivity is not.

Great entrepreneurs find a way, whether that means moving to San Francisco or staying home. The largest companies in the world were built by people from under-the-radar places. Some moved to connectivity. Some stayed. Where you start doesn't cap what you build. But those roots and affinities are the guiding point to deepening connections and a sense of community.

We saw it firsthand. I posted an Outsider Roots NYC event on X and got over 100 DMs, each a paragraph on why someone was an outsider. In San Francisco, we packed a room with top AI talent with Midwest roots.

That's why we built Roots: a social platform connecting founders, talent, investors, and enterprises through shared roots. Import your network and Roots enriches it with AI. As you connect with members and join communities, their networks layer into yours. Query the graph in plain English and find the right co-founder, customer, hire, or investor through the warmest path that already connects you.

The product runs on a few pieces: a network graph that visualizes your connections and the warmest path to anyone in it, AI search that surfaces the right person through someone who already knows you both, and communities organized around industry, geography, and shared background, where the people you meet already have a reason to trust you. 

AI matching tells you who to meet but it doesn't replace the room. That's why we pair it with curated dinners and happy hours, and why each community on Roots can run its own events, own its own member data, and communicate on its own terms, instead of the connections living in a group chat that dies in six months. 

We're starting with Missouri and the Midwest, where talent and company density is high but startup connectivity is not, and we host curated dinners and happy hours in New York, San Francisco, Chicago, Atlanta, Miami, and across a Missouri Roadshow through St. Louis, Kansas City, Columbia, and Springfield. No panels or pitches. This year we're launching the Roots Weekend, formerly Missouri Startup Weekend.

THE PROBLEM ISN'T TALENT

Paul Graham wrote in 2008 that great cities send you a message in a hundred subtle ways: you could do more, you should try harder. He's right. The problem is that most of the world's most ambitious people aren't in those cities.

After 5,000 conversations, I'm confident the biggest problem for most founders isn't capital. It's network connectivity with customers and talent. Not just getting someone to take a meeting. Founders need a critical mass of early believers who give honest feedback, sit through a rough MVP, and become actual pilot customers. In dense ecosystems, founders find them fast through overlapping networks. Everywhere else it takes longer, not because the people aren't there, but because the infrastructure to surface them hasn't existed.

If you grew up in San Francisco or went to Stanford, some of this gets solved before you start. A professor makes an intro. Your roommate's dad is at the firm you're pitching. In Columbia, Missouri, Wichita, or Pittsburgh, you have to manufacture that same warm intro density from scratch.

Stanley Milgram's small-world experiments in the 1960s found that any two Americans were connected by five or six intermediaries. The paths were always there. People find them through roots. What never existed was the instrument that shows you the warmest one.

The misconception is that places like the Midwest don't have enough people. The data doesn't support that. What's missing is connection density: how quickly the right people find each other and build something together.

PROOF

Columbia, Missouri, has a population of 126,000. When a tier-one VC invested in EquipmentShare, they told the Schlacks brothers they couldn't succeed if they weren't by water. The brothers stayed in Columbia anyway. EquipmentShare is now one of the largest YC-backed companies in history. They didn't build it because they had the right connections. They had deep domain knowledge of their customer, the kind that only comes from growing up around that industry. The network would have compressed the timeline. The roots made it defensible.

Columbia is also home to Zapier, raised $1.4M to hit a $5B market cap, and Sam Walton went to school there before building the world's largest company by revenue. Marc Andreessen grew up in a Wisconsin town of 2,500. Jack Dorsey and Sam Altman both grew up in St. Louis. Eric Yuan was denied a US visa eight times before building Zoom. The Collison brothers came from a town of a hundred people in rural Ireland and rebuilt the internet's payment infrastructure. Brett Adcock grew up in a town of 1,800 in Illinois and is now building Figure AI.

Stanford professor Ilya Strebulaev's 2025 Unicorn Report found that 44% of US unicorn founders were born outside the United States, and 78% had never been a CEO before. Silicon Valley Bank found that 59 of the top 100 US unicorns have at least one foreign-born founder, representing roughly $1.5 trillion in combined valuation. The ecosystem doesn't produce these founders. They carried something with them, and the place they landed got the credit.

At Redbud, 65% of our portfolio is immigrants or founders with Midwest roots. We didn't set out to build a geographically-themed fund. When we stopped filtering for familiar credentials and started underwriting resilience, resourcefulness, and customer insight built from proximity to the problem, that's who remained.

MINDSET

Parts of the Midwest carry a cultural default toward stability that conflicts with what venture-scale building requires. Bootstrapping a profitable company and living well are legitimate outcomes, but the same environment that celebrates them can convince founders capable of more that the ceiling is lower than it is.

Outside the main hubs, the stage also fills with people who want to help but haven't raised institutional capital or sat across from a Series B investor. The founders who break through figure out early whose input actually counts, and build their networks around people who've played the specific game they're trying to play. That's what Roots is for. Not to make company building easier. Constraints drive outlier returns, and that shouldn't change. It's to make sure the right founders are in the right rooms, getting counsel from people who've actually done it.

RECEIPTS

We hosted a Midwest Roots event in San Francisco. The room was packed. Founders and investors who'd spent years in the most connected city in the world had never once had a room where being from somewhere else was the whole point.

One person who'd been in the Bay Area for over a decade told me the closest thing they'd had to this feeling was discovering a founder they admired had gone to the same small school back home. Two years of professional acquaintance turned into a real friendship over one dinner. It happens constantly, whenever people find out they share something real. It's almost always accidental. Roots makes it intentional.

ACCESS SHOULDN'T BE A BIRTHRIGHT

You have to earn the right to win in the market. Network access is a different thing entirely. Right now it gets allocated by zip code and alma mater far more than by the quality of what someone is building. That's backward. The founder in Nebraska or Tennessee with a unique insight and outlier resilience deserves the same shot at finding the right people as someone who grew up with a network.

We’re leveling that playing field. That’s why we built Roots.

Join the waitlist today.

Brett Calhoun 

GP, Redbud VC 

Founder, Roots

Sources: Ilya Strebulaev et al., Unicorn Report, Stanford Venture Capital Initiative, April 2025. Silicon Valley Bank, State of the Markets: H2 2025. Paul Graham, Cities and Ambition, paulgraham.com, May 2008. Travers and Milgram, An Experimental Study of the Small World Problem, Sociometry, 1969.