Venture capital in the heartland is transforming, opening up new avenues for tech entrepreneurs to thrive. Nevertheless, when it comes to early-stage investing, pedigree often acts as the gatekeeper.
ut Brett Calhoun, Co-founder and General Partner at Redbud VC, is rewriting the rules.
Based in Columbia, Missouri, far from the venture-saturated coasts, Brett isn’t just funding startups. He’s cultivating ecosystems, identifying overlooked talent, and helping founders in the Midwest and beyond turn gritty conviction into generational companies.
On this episode of SaaS That App: Building B2B Web Applications, Brett shares how Redbud VC finds billion-dollar founders in places others aren’t looking, and why domain expertise, grit, and customer obsession matter more than Ivy League CVs and buzzword-heavy decks.
From Founder to Fund Builder
Brett didn’t set out to become a VC. While in grad school at Mizzou, he got his first taste of investing by supporting local entrepreneurs. One thing led to another, co-founding a lending startup, setting up CapGains, and helping to launch a regional incubator. That hustle culminated in the birth of Redbud VC.
The motivation? Supporting more entrepreneurs and spreading risk across multiple high-potential companies, not just going all-in on one startup at a time. However, the results speak for themselves: Redbud has already invested in 30 companies, many as the first committed fund.
What Redbud Looks for in Founders
Redbud VC isn’t chasing hype cycles. It’s chasing people, those who’ve rolled up their sleeves and built something without waiting for permission or capital.
Brett says they invest in resilience and conviction. Many of their founders are bootstrappers who’ve sacrificed comfort for clarity, working nights and weekends, leaving stable jobs, and proving they believe in their vision without external validation.
Domain expertise is another differentiator. Brett favors founders who have lived the problems they’re solving, like salon owners building tools for other salon owners, or lawyers digitizing broken processes in their field. These people understand their markets deeply and often have a wedge that others can’t see.
VC in the Midwest
Redbud is headquartered in Missouri, a state rarely associated with cutting-edge tech. But that’s part of what gives them an edge. “In the Midwest, you look for traction. On the coasts, you look for pedigree. What happens when a founder has neither?” Brett asks. “That’s where we come in.”
Because capital is scarcer in the heartland, valuations tend to be more reasonable and expectations more grounded. Founders often stay in the region, which helps retain talent and knowledge. Redbud’s network includes universities, legacy corporations, and community programs like Missouri Startup Weekend, creating a fertile environment for new ventures.
Startups like Appreciate, Liquid, and Focus all emerged from these initiatives, each pairing local insight with strong execution and growth potential.
Building Billion-Dollar Businesses in “Boring” Sectors
Redbud’s secret? They love so-called “unsexy” sectors, places where incumbents move slowly and customers are underserved.
Think pharmacy software, title insurance document parsing, CRISPR-edited mosquito control, or B2B warranty fintech. These verticals are ripe for reinvention, especially with the rise of generative AI.
“You couldn’t have built some of these businesses even two years ago. Now, with AI, you can unlock opportunities in spaces that were previously off-limits.”
Redbud looks for founders who combine unique insight with access to distribution. In fintech, for example, one Redbud company secured massive growth by plugging into an existing partner’s customer base, scaling without spending a dime on marketing.
How to Pitch Brett
If you want to catch Brett’s attention, don’t lead with your valuation or your pitch deck. Lead with a story and your plan.
He’s looking for founders who:
- Show real conviction and long-term vision
- Know how they’ll use the capital and can budget accordingly
- Have a technical or operational skill set on the team
- Demonstrate obsession with solving their customers’ problems
And whatever you do, don’t show up raising $5M on a $15M valuation with no traction.
Final Thoughts
Redbud VC is betting on a different model of success, one where grit, insight, and underserved geographies drive returns. Brett Calhoun and his team are proving that billion-dollar businesses can grow far from Silicon Valley, especially when investors are willing to look beyond the usual signals.
Brett’s Background
Brett Calhoun is the Co-founder and General Partner at Redbud VC, a venture capital firm focused on early-stage technology companies across the United States with particular emphasis on the heartland region. As an innovator in venture capital and SaaS, Brett brings vast experience from both sides of the startup ecosystem as a founder with companies like Stealth and CapGains, and as an investor identifying and nurturing high-potential tech ventures. His unique approach combines hands-on operational experience with strategic investment expertise, particularly in vertical software solutions and B2B applications.
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