Podcast Summary: How I Invest with David Weisburd

Episode 264: The Asymmetric Edge: Generating Alpha in Venture
Date: December 17, 2025
Host: David Weisburd
Guest: Jamie (VC, Tamarack, ex-Goldman Sachs and CO2)

Overview

This episode explores the sources of “asymmetric edge” in early-stage venture investing, with a spotlight on how foundational networks, hard-nosed diligence, intuition, and smart risk-taking drive consistent outperformance. Jamie, whose seed-stage unicorn hit rate leads industry rankings, shares in-depth lessons on sourcing, picking, and winning competitive deals. The discussion ranges from tactical sourcing techniques and diligence process, to thoughts on labor automation and reflections from his hedge fund and venture career.

Key Discussion Points & Insights

1. Sourcing Asymmetric Deal Flow

• Strongest Signal:
  • Founder referrals—especially from “5 out of 5” founders, often unicorn builders—outperform all other deal sources.
    • “When I get a phone call from that 5 out of 5 founder, often they may already be a multi-billion dollar company and they say, ‘Hey Jamie, I just met this kid ... you need to go down and meet with him or her tomorrow.’ Those are the strongest signals.” (B, 00:33)
  • Deep domain knowledge and personal experience of unicorn founders enable uniquely informed recommendations.
    • Example: Tom Mueller (early SpaceX) referencing engineers he’s worked with as high-potential founders.
      “Every single one of these companies or funds has worked for Tom in the past. He knows every single one.” (B, 01:29)
• Super-angel Alpha:
  • Top-performing ‘angel’ portfolios outperform many venture funds due to access to proprietary, trusted networks (e.g., Marc Andreessen, David Sacks).
    • “They had this asymmetric information where they were investing in friends ... engineers that worked for them. They had the benefit of knowing how effective these employees were over years.” (A, 02:56)
• Information Asymmetry = Outperformance:
  • Getting information not broadly available is key for “venture alpha” vs. “venture beta.”
    • “If you want to be truly excellent, you need asymmetric information. ... There has to be something out there, some kernel of truth or information that you’re getting that not everyone else has.” (B, 03:38)

2. Winning Competitive Rounds

• Diligence as Differentiator:
  • Outworking larger funds by applying hedge-fund-style, deep research at seed stage.
    • “We have to out hustle them as a smaller fund ... When you bring that level of homework to a founder at the earliest stage and you say, ‘Hey listen, I have a 50-page memo on your company ... I am going deep, almost private equity deep at the seed stage...’ Oftentimes you can beat people with the research that you do.” (B, 04:54)
• Challenging Lazy Industry Norms:
  • Calling out common pre-seed/seed investor laziness (“it’s unknowable”) as an excuse to avoid the hard work of diligence.
    • “[A lot of] people in pre-seed and seed ... throw their hands up and say, ‘It’s unknowable.’ ... To me, that’s also an excuse or a form of laziness to not do as much as you can...” (A, 06:19)
  • Jamie: Supports the thesis, encouraging creativity and “investigative journalist” mindset for uncovering differentiators. (B, 07:07)

3. Assessing and Attracting Founder Talent

• Critical Diligence: Motivations for Leaving Elite Orgs
  • Understanding why top engineers leave iconic companies (SpaceX, Anduril, etc.) is crucial. Are they truly top-talent seeking new frontiers, or did they burn out?
    • “Zeroing in on that diligence, on just how quality of an engineer that first one or two employees are at a company, I think is one of the things that goes under-diligenced.” (A, 07:58)
• SpaceX as Training Ground:
  • “I started my career at Goldman Sachs ... I sort of view SpaceX as, as the new [version]. Their star is so bright ... these tend to be very ambitious young people.” (B, 08:44)
• Three Archetypes (from Jamie Go, Wave Function):
  • (10:07)
    1. Burn out in six months (can’t handle “responsible engineer” culture)
    2. SpaceX lifers (deep belief in mission)
    3. People who build a skillset/network, then launch new ventures—which are prime startup talent

4. The Humanoid Robot Space & Macro Bets

• Market Overview:
  • The global labor market is ~$42T; automation of repetitive labor has massive potential and inevitability.
    • “The labor market ... is about $42 trillion a year. So we’ve got a big sandbox to play in.” (B, 11:54)
• Industrial vs. Residential:
  • The humanoid robotics opportunity is both industrial (warehouse, logistics, hotels) and residential—but immediate traction seems to favor industrial.
    • “A big 3PL (third-party logistics) player has expressed interest for 85,000 humanoids from Figure. At $100,000 a robot per year, that’s $8.5 billion in ARR right there. So that’s from one customer.” (B, 14:45)

5. Evolution as a Fund Manager

• Fund 1→2:
  • Became more concentrated; proactively offered capital at inflection points (pre-emptive rounds) to double down on breakout winners.
    • “We started to get a little more aggressive ... identify those companies that are ... hitting just one, a few big contracts ... call them up ... [ask] will they take a little more money now ... More often than not, people come to, yeah, a little extra capital right now would be nice ... and then that Series A happens and we’ve already added more to our breakout winners.” (B, 16:58)
• “Play offense as opposed to defense.”

6. Lessons from Philippe Laffont (CO2/Hedge Fund Mentality in Venture)

• Simplifying Complexity:
  • Focus on the two or three true drivers of an outcome vs. 45 checklist items.
    • “Philippe ... is a true savant in terms of boiling down very complicated things into the two or three things that really, really matter.” (B, 19:16)
• Long Time Horizons:
  • Don’t measure company value on quarters or even 1–2 years; think 5–9 years out, then backsolve to current value—applicable in both public and private markets.
    • “He always thought it was crazy that sell-side analysts ... measured companies on quarters ... think about it on a five-, seven-, or nine-year time horizon ...” (B, 20:10)
• “Gut Score”:
  • Every deal scored 1-5 on pure intuition. Real “5s” are rare and highly correlated with success.
    • “We’ve taken the same thing to Tamarack ... if you’re debating whether it’s a four or a five ... most of the time it doesn’t work out. But when you see a five ... every fiber of your being, you know ... and you take a look at that data ... it’s pretty striking.” (B, 22:34)
  • Notable quote from Josh Kushner echoed: “My deepest insecurity is that I will oftentimes have intuitions about a certain thing ... that I cannot explain to anybody else, but I just have to invest.” (B, 24:35)

7. The Power and Limits of Intuition

• Intuition is Data Integration:
  • “The gut is the synthesis of all the information that you have as investor ... you could articulate it, but step two is not necessary ... you just have to trust your gut.” (A, 26:20)
• Social Psychology & Micro-signals:
  • Micro-expressions (e.g., too much smiling) and subtle cues can be accurate—part of a learned but hard-to-articulate skillset.
    • “If somebody’s watching somebody speak at a panel ... they make their decision on if they’re going to listen to the person or not within the first three to eight seconds.” (B, 27:49)
    • “Being a better investor ... some of it is also learning to trust your instincts ... These absurd kind of reasons for why you trust or distrust someone is actually wired in millions of years of evolutionary psychology...” (A, 28:57)
• Importance of Reference Checks:
  • Reference calls and high-skill interviewing are a serious “source of alpha.” (A, 31:09)
  • “If you are in symphony and in orchestra with the other person ... you might create something interesting. ... It’s pattern matching ... it’s being able to read between the lines and it’s intuition and it’s gut, it’s all these things kind of put together.” (B, 32:25)

8. Career Advice

• Take Big Risks Early:
  • Back conviction over caution, especially early in your career; “weird and wonderful” investments are often where outlier returns are found.
    • “Take a big swing and take a big stance and prioritize conviction over caution ... If you can find something, something that’s weird and wonderful ... don’t be afraid to take huge risks early in your career.” (B, 34:35)
• Stan Druckenmiller Quote:
  • “Put all your eggs in one basket and then watch that basket carefully.” (B, 34:40)

9. Predicting Unicorns—How Confident Was the Intuition?

• Jamie’s Track Record:
  • Could not be “100% certain,” but was highly confident in the key breakouts becoming unicorns/decacorns because they involved world-class operators with unfair advantages.
    • “I could say with a hundred percent degree of certainty that I felt pretty damn good about those ones being winning outcomes ... When I went into these, people said these were not cheap ... but it’s like drafting like an all-star NBA player.” (B, 36:39)
    • “Tom Mueller ... one phone call away from Elon and he’s building in space ... I think about Chaos Industries ... John Tennant ... do I want to go up against John Tenet? No ... Do I think he’s going to win? Yes, I do.” (B, 36:50)

Notable Quotes & Memorable Moments

• On Founder Referrals:

  • “When they say you need to meet this person, I’m going to see them in the next 24 hours, most likely.” (B, 00:58)

• On Super Angel Alpha:

  • “If you want to be truly excellent, you need asymmetric information ... that’s part of the secret sauce.” (B, 03:29)

• On Deep Diligence:

  • “I have a 50-page memo on your company and I am going deep, almost private equity deep on your company at the seed stage.” (B, 05:17)

• On Investing Gut:

  • “When you see a five and you know a five, it’s like every fiber of your being, you know ... and you just know it’s a 5.” (B, 24:10)

• On Pattern Matching:

  • “It’s just pattern matching and it’s being able to read between the lines and it’s intuition and it’s gut, it’s all these things kind of put together.” (B, 33:28)

• On Early-Career Risks:

  • “Take big risks and put yourself out there ... prioritize conviction over caution.” (B, 34:39)

Timestamps for Key Segments

• [00:11] Top signal for unicorns: founder referrals
• [03:28] Asymmetric information in venture/angel investing
• [04:42] Outworking bigger funds via deep diligence
• [07:58] Diligencing why a top engineer leaves elite companies
• [10:07] SpaceX “three camps” talent breakdown (Jamie Go)
• [11:31] Humanoid robots: market size, economics, industrial vs. residential
• [16:58] Fund 1 vs. Fund 2: learning to “play offense,” preempt rounds
• [19:13] Lessons from hedge fund legend Philippe Laffont
• [22:34] Scoring investments on gut; intuition vs. rationality
• [26:20] Limitations and value of intuition in investing, micro-expressions
• [34:35] Career advice: conviction, risk-taking, “weird and wonderful”
• [36:39] How confident was the intuition in hit unicorns/decacorns

Conclusion

Jamie’s process and outperformance are deeply rooted in trusted relationships, exhaustive diligence, and unique behavioral insights—augmented by risk-taking and refined intuition. Sourcing emerges as the key, especially when drawing on the networks of all-star founders, while winning highly competitive deals relies on outworking—and outthinking—larger competitors. Intuition, data integration, and pattern recognition are identified as core tools for venture alpha, alongside the courage to bet big and trust your singular edge.

Listen for a masterclass in the art and science of early-stage venture, from someone who has demonstrably generated outsized alpha.