Why Early Investing Requires Embracing Big Misses

What happens when one of tech’s best community builders turns his playbook on venture capital itself? Ryan Hoover — the founder of Product Hunt and Investor at Weekend Fund — joins me to unpack how he’s reinventing early-stage investing. From building one of the internet’s biggest startup communities to managing a fund with 360+ LPs, Ryan shares the hard-won lessons on productizing VC, scaling systems as an introvert, and finding founders who hold true “earned secrets.” We dive into his journey from launching Product Hunt to building Weekend Fund’s third vehicle, how he thinks about portfolio construction, why weird ideas often win, and what it really takes to back the next generation of breakout founders. Whether you’re a founder, operator, or investor — this episode is packed with insights on scaling yourself, spotting alpha before it’s obvious, and turning community into competitive advantage.

Highlights:

• How Ryan built Product Hunt into a launchpad for over 100,000 startups.
• The story behind raising from 360+ LPs — and why one investor literally became a monk.
• Why Weekend Fund prefers staying small to keep conviction high.
• The psychology of “weird” investing — and why strange ideas often outperform.
• How Ryan productized LP intros and scaled value-add through software.
• Why the best investors give without expecting anything in return
• How to build a scout network that multiplies your reach without adding complexity.
• The key traits of elite super connectors (and why Ryan doesn’t see himself as one).
• Why founders with “earned secrets” beat consensus every time.
• Ryan’s one piece of advice to his younger self before launching his first fund.

Guest Bio:

Ryan Hoover is the Founder and Investor at Weekend Fund, an early-stage venture capital firm investing in founders with earned secrets—deep insights derived from firsthand experience. Weekend Fund has raised three funds and invested in over 100 startups globally, including Deel, Replicate, and Rally, backed by a diverse community of more than 360 limited partners. Before founding Weekend Fund, Ryan founded Product Hunt, the platform that helped launch tens of thousands of startups and shaped how the tech world discovers new products. He has since focused full-time on building a new venture model centered around community, transparency, and product thinking.

Stay Connected:

X / Twitter: David Weisburd: @dweisburd Ryan Hoover: @rrhoover

LinkedIn: David Weisburd: https://www.linkedin.com/in/dweisburd/ Ryan Hoover: https://www.linkedin.com/in/ryanrhoover/

Links Weekend Fund: https://www.weekend.fund/

Questions or topics you want us to discuss on How I Invest? Email us at david@weisburdcapital.com.

(0:00) Preview (0:14) Secrets, lived experience, and productizing LP intros (1:51) Fundraising challenges and LP base management (3:07) Downsides and expectations with 360 LPs (6:31) Venture capital as a product and Weekend Build experiment (9:10) Rolodexer success and becoming an elite super connector (14:18) Using value add to win deals and portfolio construction strategies (22:10) Ryan Hoover's LP activities, SPVs, and strategic investments (26:11) Scaling productivity and weekend partners program (29:17) Transparency and investing in non-consensus companies (37:42) Information diet, advice to younger self, and early strategies (42:00) Best product importance vs. portfolio construction and market changes (43:32) Managing a large portfolio and scaling support with tools (44:14) Closing remarks