Insights from a 25-year veteran angel who advises investors and governments across four continents while chairing Silicon Valley's oldest angel network and the ACA Board of Directors

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

1. Angels are insulated from market turbulence - Ron's data shows angels maintaining pre-2021 investment patterns despite market volatility in recent months.
2. First-time CEOs are getting MORE funding - Contrary to what you'd expect in uncertain times, angels are backing more first-timers than ever. This challenges the conventional "flight to safety" narrative.
3. Long-view investing as emotional discipline - Ron's emphasis on the reality of 5-8 year time horizons for angel investments is a psychological framework that helps investors avoid reactive decisions to monthly or quarterly fluctuations.

I explore these ideas and more with Ron Weissman, Chair of the Board of Directors at the ACA. He brings over 25 years in global venture capital and nearly two decades as an angel investor to his role. As Chairman of the Software Industry Group at Band of Angels, Silicon Valley's oldest angel network, Ron combines deep technical knowledge with historical perspective, having previously served as a CMO and Director under Steve Jobs at NeXT. His unique background as both a former Professor of History and technology executive made this a fascinating lesson in navigating uncertainty.

During our conversation, Ron shares:

• Evidence-based perspective on angel resilience backed by quantitative data showing investment patterns remain consistent despite economic turbulence.
• A counterintuitive insight that angels are funding more first-time CEOs than ever before, challenging the assumption that uncertain markets drive investors toward experienced founders.
• Historical patterns showing funds started after economic downturns "went higher, faster" and why this makes economic turbulence potentially advantageous for disciplined investors.

Connect with Ron

LinkedIn

Stuff We Reference

• Denominator Effect by Ron Weissman
• Mary Todd Lincoln
• ACA
• Band of Angels

Know someone who would enjoy this episode? Share it with them!

P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts.

Want more?

• Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter.
• Check out the entire show library and follow via Apple Podcasts, Spotify, and YouTube.

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.

Insights from a global ecosystem builder who's processed data on 108,000 startups while helping 240 investor communities across six continents manage their deal flow

GET FREE SOCKS: Seren will send the first 100 listeners that sign up for the AI Portfolio Monitoring waitlist a pair of Dealum’s signature red socks. What better way to impress your fellow angels at the next pitch event?!

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

1. A 30% spike in angel fundraising activity in Q4 2024 - Seren shared data showing a remarkable uptick in companies submitting fundraising applications, which could have a wide range of implications.
2. 2,000 new companies per month - That's 108,000 startups total with structured data! Such a value-add for the ecosystem.
3. The "pitch deck black hole" - Seren's firsthand experience as a failed founder gives her empathy for entrepreneurs who send applications “into the void.” This perspective is so important for investors to consider as we design and implement our processes.

I explore these ideas and more with Seren Rumjancevs, CEO of Dealum.

Seren brings a rare 360-degree perspective to early-stage investing as Dealum's CEO, having previously served as a founder, accelerator manager, and innovation consultant across Estonia and the UK. Since 2019, she's led the platform that now manages deal flow for over 240 investor communities worldwide with data on more than 108,000 startups. Her firsthand experience with the "pitch deck black hole" as a former founder drives her mission to create greater transparency and efficiency across the early-stage fundraising ecosystem.

During our conversation, Seren shares:

• How a perfect storm of platform failures created both opportunity and skepticism - revealing the challenges European startups face when trying to win trust from US angel communities during a crisis.
• Insights from tracking 108,000 startups globally, including recent data showing a 30% spike in fundraising activity starting in Q4 2023.
• Why portfolio tracking remains a major operational challenge for angel groups, detailing how Dealum’s newest AI solution will transform unstructured email updates into structured data visualizations.

Connect with Seren

LinkedIn | LinkedIn | X

Know someone who would enjoy this episode? Share it with them!

P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts.

Want more?

• Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter.
• Check out the entire show library and follow via Apple Podcasts, Spotify, and YouTube.

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.

Insights from a fund manager who has mobilized hundreds of women investors, championed gender-lens investing in the Southeast, and is now steering the ACA as its incoming Chair

Today's episode explores 3 ideas that caught my attention:

1. Women angels grew 8x in 10 years - Kristina shared that female angels increased from 5% to 40% of all angel investors since 2014.
2. "Get out of your sandbox" - Her advice to deliberately step into unfamiliar networks struck me as the simplest yet most overlooked strategy for finding opportunities others miss.
3. Let’s be honest: we make investment decisions from the heart - When she quoted Bill Payne that investing ultimately comes from the heart, it validated what I’ve observed again and again. At the end of the day, most angel investment decisions, no matter how well researched or diligenced, are made with our gut.

I explore these ideas and more with Kristina Montague, Managing Partner at JumpFund, which supports women-led ventures in the Southeast. As incoming Chair of the ACA and author of Jump In: Women Investing in Women, she brings over a decade of experience in gender-lens investing and building investor networks that drive returns and expand opportunities for overlooked founders.

During our conversation, Kristina shares:

• Her account of launching the first micro-venture fund in the Southeast focused entirely on women-led ventures, illuminating the unique challenges and opportunities of pioneering a gender-lens investment approach in a traditionally underserved region.
• Tactical approaches for overcoming bias in investor due diligence questioning, including awareness of "prevention vs. promotion" questioning patterns that can disadvantage certain founders.
• An insider's view of the ACA's strategic initiatives, including new individual membership programs and advanced AI tools to leverage 20 years of investor data.

Connect with Kristina

LinkedIn | Website | X

Stuff We Reference

• Angel Funders Report
• Ron Weissman
• Marcia Dawood

Know someone who would enjoy this episode? Share it with them!

P.S. Your feedback is important to me. Also, it tells the algorithms to pay more attention, which helps me out a lot. If you enjoyed this episode, hit the "like" button or leave a comment with your thoughts.

Want more?

• Get essential angel intel straight to your inbox every week with The Diligent Observer Newsletter.
• Check out the entire show library and follow via Apple Podcasts, Spotify, and YouTube.

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.