The Diligent Observer Podcast

Episode 49: "It's a Volume Game" | Redbud VC's Brett Calhoun on Generalist Investing Philosophy, the Missouri Startup Ecosystem, and Why Gritty Industry Veterans Make Compelling Founders

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Today's episode explores three ideas that caught my attention:

  1. The Missouri ecosystem is wild - I’ve 100% been sleeping on it. Names like Zapier, Equipment Share, Veterans United, and so many more all started there. It’s so easy to miss entire innovation hubs outside the usual suspects.
  2. Volume as competitive advantage - 300 LinkedIn messages weekly for five years straight. Sustaining this hustle is simple but NOT easy, and inevitably becomes a sourcing moat through sheer persistence.
  3. VCs pivot too - After launching an accelerator, Brett discovered the most valuable thing they did was make introductions to customers and investors, not programming. So they pivoted their strategy.

I explore these ideas and more with Brett Calhoun, General Partner at Redbud VC,  a top-decile early-stage venture fund that has carved out a unique positioning in America's heartland. A former entrepreneur who co-founded three fintech startups and was named to Forbes 30 Under 30 in Venture Capital in 2024, Brett brings both operational experience and financial expertise to his role. His firm's counter-positioning strategy - focusing on gritty founders with industry experience rather than traditional pedigree - has begun to generate outsized returns while building a distinctive brand amidst Missouri's robust startup ecosystem.

During our conversation, Brett shares:

  • The Missouri market inefficiency - explaining how 20% of Forbes 300 companies are concentrated in the region, but only 6% of venture-backed startups.
  • The counterintuitive insight that “forcing your framework” might not be such a good idea - learned through experience that pushing a playbook onto entrepreneurs can actually kill their trajectory.
  • Why volume trumps thesis - detailing how conducting 1,500 annual first calls and reviewing thousands of deals creates a sustainable competitive advantage over pure thematic approaches.

Connect with Brett 

LinkedIn | X

Stuff We Reference

  • Redbud VC
  • Forbes 30 Under 30
  • Synvect
  • Scale Accelerator
  • EquipmentShare
  • Veterans United Home Loans
  • Carfax

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All opinions are personal and may not reflect the views of The Diligent Observer. Not investment advice.

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The Diligent Observer PodcastBy Andrew Kazlow