What does it actually mean to bet on yourself, and how do you know if the game you’re playing is really the one you want to be in?

In this special episode of Supra Insider, Marc Baselga and Ben Erez record together in person for the first time, sitting down at a studio in New York to have an honest, unscripted conversation about optionality, partnership, and what they’ve learned from building Insider Loops over the last seven months. They open with the question hanging over a lot of high-agency people right now: with AI making it easier than ever to go from idea to product, should you leave your job and bet on yourself? Marc names the only full-time role that genuinely tempts him, Anthropic, and then explains exactly why he still wouldn’t take it. Ben unpacks why he accomplished 20% of what he was capable of during his full-time years, and what changed.

They go deep on why bootstrapping is harder than raising VC money, but why the constraints force the kind of market discipline that most funded companies never develop. They map out their complementary skill sets, how they’ve shifted from long-term planning to weekly cadence, and why they now think planning more than a week ahead is mostly a waste of time. The conversation closes on the role of the podcast itself, why it has to stay separate from the business, why fun is an emergent property and not a frivolous goal, and why the relationship comes first.

If you’re weighing whether to leave a stable job and go off on your own, curious about what a bootstrapped partnership actually looks like day to day and what makes it work, or just want a rare honest conversation between two builders about what they’d do differently and what they wouldn’t change, this episode is for you.

A special thanks Alex Pavlou and the team at 28th & Park for the recording space!

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Want company-specific interview intel?

If you’re preparing for PM interviews at Meta, Anthropic, OpenAI, Google, Stripe, DoorDash, Uber, or Figma… 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:

* (04:30) The optionality question: what paths are Marc and Ben actually considering?

* (09:20) Marc’s three paths: full-time job, venture-backed, bootstrapped, and why Anthropic is the only real temptation

* (12:04) Full agency over your environment: the real reason the bootstrapped path feels different

* (15:54) Ben: “I accomplished 20% of what I was capable of during full-time employment”

* (20:00) Playing the same game: why co-founder alignment is everything and corporate environments make it hard

* (26:00) Bootstrapping is harder than raising VC, and why that’s actually the advantage

* (32:32) Constraints lead to creativity: time as the most precious resource

* (36:00) Fun is an emergent property, why finding work that feels fun is harder than it sounds

* (44:30) Opportunity-founder fit: how Marc and Ben’s complementary skill sets became clear through action

* (01:00:00) The Insider Loops story: from Gamma presentations to a native code base in a week

* (01:04:40) Why they stopped planning more than a week out, and why it works

* (01:13:00) A year from now: what they each hope to be feeling

* (01:22:20) The role of the podcast vs. Insider Loops, and why they have to stay separate

* (01:28:28) Thanks to the studio: 28th and Park, NYC (Alex Pavlou and team)

* And more!

Links:

* Alex Pavlou: https://www.linkedin.com/in/alexpavlou/

* 28th & Park: https://28thandpark.podyx.com/

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

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

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