Emerging Manager Q&A: Brett Calhoun about $25M Redbud Fund II
Redbud VC bet the best founders aren't where VCs are looking and raised an oversubscribed $25M fund to prove it. We asked Brett 10 questions about how they did it
Hey folks,
This is Pavel, welcome to a new edition of our Emerging Manager Q&A where we ask recently-closed fund managers 10 rapid-fire questions about their fundraising journey.
Today’s guest: Brett Calhoun, General Partner of Redbud VC.
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About the firm
Redbud VC Fund II is a $25M pre-seed fund focused on “outsider founders” strengthened by struggle, led by Willy Schlacks, Brett Calhoun, and Jabbok Schlacks. Based in Columbia, Missouri, the firm writes $250K–$500K checks into resilient founders building technology companies across North America, with no bias toward pedigree, coastal networks, or traditional backgrounds.
The team’s conviction comes from operating experience. Willy and Jabbok co-founded EquipmentShare, a construction equipment platform they scaled from Missouri to a multi‑billion‑dollar business and took public on Nasdaq in January 2026, proving that category-defining companies can be built far from the coasts. Redbud is that experience made institutional – a dedicated vehicle for the kind of overlooked talent they’ve watched grind in Middle America.
Fund II is five times larger than Redbud’s $5M debut fund raised in 2023 and was oversubscribed versus its initial target. The vehicle is anchored by the University of Missouri System Endowment, Jim McKelvey (co‑founder of Square), and AngelList Fund of Funds, alongside dozens of operators who have built substantial companies in construction, manufacturing, payments, healthcare, and tech.
Since 2023, Redbud has backed more than 40 teams across 20+ North American cities, often as one of the first institutional checks. Fund II is already active with investments in AI, software, and vertical tech, and the firm continues to hunt for generational founders in geographies and sectors where other funds simply aren’t looking.
Here is our fireside chat:
What is your fund’s superpower in one sentence?
Redbud's superpower is that it's run by operators who've actually built a unicorn in the middle of nowhere, giving them both the credibility to attract outsider founders and the pattern recognition to back them before anyone else will.
How long did the active fundraising process take?
8 months.
Did anybody help you during fundraising: existing LPs, fellow GPs, placement agents?
No.
How many LPs are in the final cap table, and what’s their breakdown?
66 LPs: 14% institutional, 3% FoF, 83% High Net Worth / Family Offices.
What was the fastest check – time from first call to signed subscription?
Immediately after the first call.
What were the top 3 reasons LPs said “NO”?
Bad timing, not a fit (liquidity, no depreciation, too risky, etc.), wanting more of a specialist.
What were the top 3 signals that an LP was truly interested in your fund?
Offering to make intros to friends/colleagues
Asking – who else is invested, capital call schedule, minimum, how they can get involved
Schedule a follow up that also includes my partner
What did LPs actually pay close attention to during fundraising?
Progression of Fund I and who else committed.
What’s the biggest mistake fund managers make when fundraising?
Not getting super focused/granular with their initial prospect list.
What advice would you give to your future self and to other emerging managers about fundraising?
You have to build multiple points of momentum, which should start months before fundraising.
Learn more about Redbud VC: Fund II Announcement
Who do you want me to interview in the next episode?
We’d love to hear your ideas – hit reply below.
love the outsider founders thesis. congrats on the close!