Choosing first investors heuristics

What actually makes a startup defensible anymore, especially when anyone can build a product overnight with AI?

In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Itamar Novick, founder of Recursive Ventures and longtime operator-turned-investor, to unpack how moats are changing in the AI era and what founders (and senior product leaders) need to internalize if they want to build enduring companies.

Itamar draws from over 25 years across product leadership, company-building, and early-stage investing to explain why defensibility matters earlier than most founders think, how traditional moats (marketplaces, SaaS velocity, network effects) still apply, and why AI radically compresses time-to-competition. He breaks down how Recursive Ventures evaluates teams, TAM, and moats at the pre-seed stage, why velocity has become a core signal, and how the venture model itself is being reshaped by smaller teams, faster execution, and lower capital requirements.

The conversation also goes deep on founder decision-making: how to choose early investors, why community itself can be a moat, what good vs bad VCs look like when companies fail, and why product leaders should seriously consider jumping into AI-native environments, even if it means a short-term step down.

If you’re a product leader thinking about founding a company, advising startups, or staying relevant in the next decade, this episode offers a clear, opinionated framework for navigating what’s changed and what still matters.

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If you’re a PM preparing for interviews at Uber, Figma, Stripe, and DoorDash… we think you’re going to love Insider Loops. You can read about it in Ben’s LI post, Marc’s LI post or check out the site directly below.

In this episode, we covered the following topics:

* (05:34) Itamar’s path from VC to operator and back, and why credibility matters in early-stage investing

* (09:45) Why Itamar looks for moats even at pre-seed

* (12:50) Classic pre-AI moats: marketplaces, SaaS velocity, and network effects

* (19:21) How Recursive Ventures evaluates Team, TAM, and Moat at inception

* (21:44) Vibe coding and the collapse of traditional barriers to entry

* (26:38) How AI breaks traditional venture math, and why seed investing benefits

* (30:07) How founders should choose their first investors

* (34:49) Three types of VCs: helpers, neutral capital, and destructive investors

* (44:13) How much to raise at pre-seed and what that capital is actually for

* (51:10) Hiring for leverage: why AI-native mindset matters more than tenure

* (54:27) Why working at AI-native companies compounds long-term career value

* (57:23) Sales, distribution, and personal brand as differentiators

* (1:00:25) How PMs can build sales and founder muscles intentionally

* And more!

Links:

* Startup Anti-patterns by Itamar Novick: https://www.itamarnovick.com/category/anti-patterns/

* Itamar Novick: https://www.linkedin.com/in/itamarnovick/

* Itamar’s X: https://x.com/Itamar_Novick

* Recursive Ventures: https://www.recursiveventures.com/

* Marc: https://www.linkedin.com/in/marcbaselga/

* Ben: https://www.linkedin.com/in/benerez/

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