All Episodes

November 11, 2025 38 mins

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

  1. Angel investment dollar-cost averaging - The vintage year matters, and Amy's comments got me thinking about how traditional finance concepts like DCA can be applied effectively in the angel investing world.
  2. Curation creates commitment - Amy's insight that showing fewer, highly-vetted deals can increase member engagement challenges a common assumption I see in the angel space that more deal flow equals more value.
  3. The founder is everything - Amy's collaboration with clinical psychologist Marty Dubin to systematically assess founder DNA made me think about how tempting (at least, at the pre-seed and seed stage) it is to focus on evaluate a business when we really should be evaluating the person.

I explore these ideas and more with Amy Brandenburg, Co-Founder and Managing Partner of Denver Ventures Seed Fund, which has grown from an informal angel group to managing $65M+ AUM in just five years. Amy brings an iterative mindset thanks to her time at GitLab, as well as a distinctive focus on "founder DNA", collaborating with clinical psychologist and serial entrepreneur Marty Dubin to develop proprietary psychological evaluation methods that go beyond traditional due diligence in early-stage investing.

During our conversation, Amy shares:

  • Member activation strategies that helped Denver Ventures grow from informal group to 850+ investors including why partner skin-in-the-game was crucial for credibility.
  • Lessons from GitLab's asynchronous culture including the "no agenda, no meeting" rule and iteration-over-perfection mindset that shaped her leadership approach.
  • Why Colorado's 20-year ecosystem building strategy succeeded where others failed and how coastal capital migration during COVID accelerated regional growth opportunities.

Connect with Amy

LinkedIn | X

Stuff We Reference 

Register for the ACA Summit and use code DO200 at registration to save $200!

Want more? 

Connect with Andrew 

LinkedIn | X | Angel Ops E-Book

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

Listen
Watch
Mark as Played

Advertise With Us

Popular Podcasts

Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

The Breakfast Club

The Breakfast Club

The World's Most Dangerous Morning Show, The Breakfast Club, With DJ Envy, Jess Hilarious, And Charlamagne Tha God!

Stuff You Should Know

Stuff You Should Know

If you've ever wanted to know about champagne, satanism, the Stonewall Uprising, chaos theory, LSD, El Nino, true crime and Rosa Parks, then look no further. Josh and Chuck have you covered.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2026 iHeartMedia, Inc.

  • Help
  • Privacy Policy
  • Terms of Use
  • AdChoicesAd Choices