Investing in Startups

Dan Teran is a Cofounder and Managing Partner of Gutter Capital. Gutter is an early-stage firm based out of New York focused on founders tackling the world’s toughest problems. We talked about why Gutter invests with conviction, why they seek out founders with unique insights rather than Gutter trying to dream up their own, and how AI can solve problems in the real world, not just online. We also dug int...

Our guest this week is David Gardner, Cofounder of The Motley Fool. David is one of the best stock pickers of his generation. While for many investors a single 100X investment would be a career-defining win, David has earned a 100X return on 6 companies including Nvidia, Tesla, Amazon, and Netflix. We talked about breaking the rules of investing, optionality, valuation, letting winners run, and much more. Dav...

David Zhou is an investor in emerging managers, an angel investor, a blogger, and the host of the Superclusters podcast. We talked about how LPs can size up emerging managers, how VCs can stand out, portfolio construction, and which of sourcing, picking, and winning is the most important. We also explored:

+ Why David thinks that “access beats picking...

We're trying something new with our first roundtable! Our guests are Sonia Nagar from SNAK Venture Partners and Colin Gardiner from Yonder Ventures. Sonia and Colin are both early-stage investors, friends of mine, and experts on marketplaces and network effects. We talked about AI’s role in marketplaces, why network effects aren’t more popular (even though they should be), how to make your own luck, what it’s...

Our guest this week is Hunter Walk, Co-Founder of Homebrew and Screendoor. Hunter has a deep background in product, including from his time at Google and YouTube, but is best known for his investing. Homebrew’s big wins over the years include Chime, Plaid, Gusto, Cruise, and more. We talked about trust and context, product, funnel math, investing life after LPs, and why Hunter isn’t as fussy these days about ...

Joe Magyer is the host of Investing in Startups, but his real job is running his early-stage boutique, Seaplane Ventures. In this episode, Joe is interviewed by his friend Owen Raszkiewicz, Founder and CIO of Rask Group and host of the Australian Investors Podcast. Joe talked why he made the move from public to private markets, how small firms can compete with big firms, the current venture landscape, putting...

Jackie DiMonte is the Cofounder and General Partner of Grid Capital. We talked about power laws, investing with conviction, how to help founders in their earliest stages, small funds vs. big funds, and whether pre-seed valuations really are mental. We spoke in depth about:

 - Why Pre/Seed (not just “pre-seed”). Jackie sees pre/seed as a continuum...

Morgan Flager is the Managing Partner of Silverton Partners. Silverton is an early-stage firm that has had more than 30 companies IPO or get acquired. We talked about the art and science of portfolio construction, when to bend on price, and which of team, product, or market is most important. We also dove into:

Silverton’s “early PMF” lane. Sweet spot...

Rex Salisbury is the Founder and General Partner of fintech-focused Cambrian Ventures. We talked about how Rex built a big community and following in the fintech world, why fintech startups are on a roll, disruption versus partnership, and how the venture world is evolving.

Other topics include:

• The Bay Area fosters a unique culture of openness a...

Charles Hudson is the Managing Partner and Founder of Precursor Ventures. Precursor is a generalist pre-seed firm based in San Francisco that invests in startups from all over. We talked about the importance of founder-centric investing, portfolio construction, and the balancing act of taking money off the table with winners. Charles has made over 400 investments at Precursor and has a lot of insights to draw...

David Cohen is the CEO and Cofounder of Techstars. Techstars is one of the OGs of startup accelerators, investing in almost 5,000 startups since Techstars was founded in 2006. David himself is a serial entrepreneur who was the founding CEO at Techstars, later stepped back from that role, and then returned as CEO in 2024. We talked about the problems that Techstars solves for founders, how vibe-coding affects ...

Gigi Levy-Weiss is a serial founder and a Founding Partner at NFX. NFX is an early-stage firm that has established itself as one of leading experts in network effects. We talked about network effects, AI agents, the importance of speed of exectuion, why first-mover advantages are overrated, and how NFX has built its own brand, systems, and network effects. 

We also covered:

...

Josh Muccio is the Founder of Read more