What Milestones Would Justify More Time?

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What happens when a creative side project starts to gain traction—but the founders have different ideas about how far to take it?

In this unusually raw episode of Supra Insider, Marc and Ben invite their longtime friend and coach Josh Herzig-Marx to facilitate a live coaching session—on the podcast. Together, they explore the tension between friendship and business, how to manage an unequal split in effort, and whether to go “all in” on Insider Loops or preserve what’s already working.

This episode is for anyone navigating high-stakes collaborations, co-founder relationships, or creative projects that start as fun, but might be worth so much more.

Expect vulnerability, laughter, some hard truths, and surprisingly actionable advice on alignment, contribution, and staying friends while building together.

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Interviewing at Uber, Figma, Stripe, or DoorDash?

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:

* (01:55) The intent behind recording a live coaching session

* (04:36) Marc & Ben’s backstory as friends and collaborators

* (09:32) Launching the podcast and Insider Loops

* (17:49) Debating monetization: values, brand integrity, and potential upside

* (22:28) The podcast as a stabilizing force—personally and professionally

* (30:01) The transitioning period in Ben’s life

* (43:44) The shared challenge with this personal and professional relationship

* (49:13) Unpacking fairness: hours spent vs impact made

* (56:26) Trust, tradeoffs, and marginal utility when lives are different

* (1:05:03) Should they try playing Insider Loops on “hard mode”?

* (1:09:31) Wrapping up with clarity, superpowers, and gratitude

* And more!

Links:

* Joshua Herzig-Marx Website: https://joshua.herzig-marx.com/

* Joshua Herizg-Marx: https://www.linkedin.com/in/joshuaherzigmarx/

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

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

If you’re a new subscriber, we encourage you to check out some of the recent episodes you might have missed:

To support the podcast, please check out the links below:

* Supra has teamed up with Maven to bring you something special – courses that our own community members have personally curated. And because you’re part of the Supra family, you can get up to 35% in some of these handpicked selections with code SUPRAxMAVEN.

* Preparing for Meta-style PM interviews? Check out Ben’s 🤖 AI Practice Copilot for Meta-Style PM Interviews. Get unlimited practice reps with calibrated feedback on Product Sense & Analytical Thinking questions. It’s like having an ex-Meta interview coach available 24/7. Featured in Lenny’s Newsletter 🔥

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit suprainsider.substack.com