Podcast Summary: "The Future of Venture: Ryan Hoover on Productizing VC"

Podcast: How I Invest with David Weisburd
Host: David Weisburd
Guest: Ryan Hoover (Founder, Product Hunt & GP, Weekend Fund)
Episode: #227
Date: October 17, 2025

Overview

In this engaging episode, David Weisburd interviews Ryan Hoover, founder of Product Hunt and General Partner at Weekend Fund, to explore the future of venture capital, the concept of “productizing VC,” and Ryan’s evolution from product builder to investor. Ryan candidly discusses the process of scaling a venture fund, strategies behind building and managing a large LP base, product- and system-based approaches to investing, and lessons learned from both successes and failures. Listeners are treated to practical insights on super-connecting, portfolio construction, alpha generation, and the role of lived experience in venture returns.

Key Discussion Points and Insights

1. Productizing Venture Capital

Timestamps: 00:14, 06:48, 07:06

• Hoover's Product Mindset:
  Ryan describes his passion for building products that “can scale infinitely, that can provide value or help people while I'm sleeping.” (00:14, 06:48)
• Experimentation in VC:
  Many of Weekend Fund’s experiments around productizing VC have failed, but key learnings have emerged.
  • Weekend Build: An 8-week, mini-accelerator for side project builders. The expectation was to surface high-conviction founders, but the selection bias toward those unwilling to quit jobs led to its shelving. “We selected incorrectly...It does require massive scale, and a lot of that is very difficult to productize.” (07:06)
  • Rolodexer:
    A tool that searches Ryan’s Twitter followers to generate high-conversion introductions for founders, demonstrating scalable, automated value-add. “Conversion rate, I'd say, 30 to 50% of people accept an introduction from those outbound requests.” (10:29)

2. Fundraising and Managing a Large LP Base

Timestamps: 01:51, 02:01, 03:18, 05:03

• 360 LPs Strategy:
  Weekend Fund intentionally built a diverse LP base of operators, founders, and institutions through public applications and selective processes, not just for capital but for community and value-add.
  “It wasn't about the money...It was really about bringing them on board and getting hopefully support with the portfolio.” (02:01)
• Risks and Lessons:
  The key risk was LPs not understanding fund commitments, but issues were minimal. Selectivity and education upfront helped.
  Notable story: One LP became a monk, requiring a capital return. (03:18)
• Future Adjustments:
  “We didn't have protections in our LPA...so in the future we'll...provide some protections for ourselves.” (05:36)

3. First Principles of Super-Connecting

Timestamps: 10:29–15:49

• Ryan’s Approach:
  As an introvert, Ryan prefers scaling through digital products, rapid Zooms, and systematization instead of high-touch, in-person networking. (10:40)
• Connection Best Practices:
  David outlines principles: Every introduction is additive or destructive, double opt-in is crucial, and empathy plus pickiness is the mark of the best super-connectors. (11:43)
• Giving Without Immediate Return:
  Ryan shares, “I think it lowers the pressure of someone feeling like, oh, I gotta...respond. If I give them permission to just hit instant archive, it's fine for me, it's fine for them.” (13:04)
• Infinite Value Creation:
  “As they give more value, they get reciprocity back and they have more value to give—non zero sum perspective...” – David (14:19)

4. Winning Deals and Value-Add

Timestamps: 16:04–19:03

• Access and Founder Rapport:
  Product Hunt’s network gives strong inbound access; Weekend Fund’s small checks make them easy to include in tight rounds. “In many cases we're a small enough check where even if they're, you know, tighten allocations, they can make room.” (16:09)
• Sampling Value-Add:
  Sometimes, tools like Rolodexer are offered before getting allocation, but usually post-investment for efficiency. (18:35)

5. Portfolio Construction Insights

Timestamps: 19:03–21:34, 43:10–45:00

• High Volume, Large Outcomes:
  The goal is 2–3% ownership, with decacorn (>$10B) outcomes as the target. Ryan cites investments like Deel ($10M cap to $12B value) as illustrative.
• Adjusting to Market Realities:
  “We're seeing the scale of companies, revenue growth like scale tremendously...AI is going to eat more into the services side of GDP.” (19:11)
• Fund Construction:
  About 50 companies per fund, staying responsive without being on boards: “We are very responsive and in some cases, proactive, but we're not on boards. We're not pinging the founder every week, so we're able to scale ourselves.” (43:10)

6. Scaling as an Investor

Timestamps: 27:10–30:16

• Weekend Partners (Scout Program):
  Non-exclusive scouts (25% of fund carry) source deals, providing hands-on, real-time market insight.
  “I do which is it's changing so quickly, tech is changing so fast...” (27:22) “Connor, for example, is a weekend partner...He's in the current YC batch with an AI company...he's on the floor speaking with other founders building in this kind of emerging tech ecosystem.” (28:08)
• Transparency for Scale:
  Slack channels, not DMs, foster an open, collaborative, and learn-by-watching environment. (31:26)

7. Embracing Weird and Non-Consensus Ideas

Timestamps: 32:33–35:25

• Weirdness as Alpha:
  “If you're only looking at hot deals, then you're only playing the consensus game...you're going to miss some of those weird companies...helping a founder when no one else would is, I think, meaningful and important.” (32:58)
• Lived Experience as Edge:
  “Life experience...is like the best alpha that you can get...Product Hunt was a fully distributed team...that was the reason why we invested in Deel.” (35:25)

8. LP Investing and SPVs

Timestamps: 23:22–26:23

• Ryan as an LP:
  Over 30 fund investments, mainly for network effects, perspective, and learning—not just financial returns.
  • Focus on small, specialized, or highly connected funds.
• SPVs:
  Opportunistically pursued, but early stage remains primary focus. LPs are given first dibs; strategic angels are then invited.
  • On winning highly competitive follow-ons: “A lot of venture is relationship driven. As much as I love to productize things...it is very much relationship driven.” (26:42)

9. Information Diet and Learning

Timestamps: 38:41–40:17

• Conversational Alpha:
  While Twitter is a useful firehose, Ryan values private and contextual conversations as the ultimate “information alpha.”
  “A lot of my blog posts were inspired by just conversations with smart people...conversations is in some ways maybe the ultimate alpha in terms of information diet.” (38:59)
• David's Take:
  “It’s like a podcast made just for you on exactly what you're thinking about.” (40:01)

10. Advice for Early Self & Common VC Pitfalls

Timestamps: 40:25–42:32

• Early Mistakes:
  Over-indexed on the coolness of products instead of evaluating founders' plans and business models.
  • “It’s very different when you're thinking about it from ‘here’s a cool product’ versus ‘here’s a great business.’ It's a very different muscle.” (40:40)
• Founder Self-Drive:
  Prefer founders who “need you the least.” Don’t be flattered just by being heard; invest in self-motivated, independent thinkers. (42:03)

Notable Quotes & Memorable Moments

• On Productizing VC:
  “I love building products that can scale infinitely, that can provide value or help people while I'm sleeping.” – Ryan (00:14, 06:48)
• On Finding Alpha:
  “If you want non-consensus returns, you truly need to do something that is seen as non-consensus by extremely smart people.” – David (34:21)
• On Reputation and Value Add:
  “The worst thing you could do as a founder is bring on an investor who is net negative and word gets around. Reputation matters.” – Ryan (00:41, 13:39)
• On Venture as Relationships:
  “A lot of venture is relationship driven. As much as I love to productize things...it is very much relationship driven.” – Ryan (26:42)
• On Infinite Value Creation:
  “There's an infinite amount of innovation. You could always make something better, you could always improve something...Paradoxically, as they give more value, they get reciprocity back.” – David (14:19)

Timestamps for Key Segments

• Productizing LP Intros & Fundraising: 00:49–03:18
• Managing 360 LPs—Upsides and Downsides: 03:07–05:36
• Experiments in Productizing VC: 06:48–09:07
• Becoming a Super-Connector & First Principles: 10:29–15:49
• Winning Deals and Value-Add: 16:04–19:03
• Portfolio Construction and Chasing Decacorns: 19:03–21:34, 43:10–45:00
• Scaling Yourself Through Scouts/Partners: 27:10–30:16
• Embracing Weird, Non-Consensus Investing: 32:33–35:25
• Advice for Early-Career VCs: 40:25–42:32

Tone and Language

The discussion blends candid, practical advice with thoughtful reflections and a humble, open tone. Ryan is forthright about experimentation, failure, and the iterative nature of both product and fund building. Both speakers avoid VC jargon, are direct about the challenges and joys of the work, and repeatedly stress the importance of “earned secrets” and lived experience in venture success.

Conclusion

Ryan Hoover’s journey underscores the importance of thinking of venture capital as a product—one that can be continually improved, partially automated, and scaled, but which still relies on human relationships and unique insights. His hybrid approach—driven by tech tools, a diverse LP community, and a “give-first” mindset—offers a roadmap for GPs looking to scale their impact in early-stage investing.