#135: Inside a live co-founder money therapy session | Jeff Greenberg (Executive & Founder Coach)
What happens when two co-founders sit down and talk honestly about money, not as a spreadsheet, but as fear, desire, and freedom?In this episode of Supra Insider, Marc Baselga and Ben Erez sit down with Jeff Greenberg, an executive coach and therapist who spent a decade on Wall Street as a macroeconomist, for a live co-founder coaching session on their relationship with money. Jeff guides them through a short mindfulness practice and a structured exercise adapted from couples work. Marc and Ben ask each other what they fear when it comes to money, what they really want, and what they love about working together.They explore Jeff’s three pillars of financial lineage, intimacy, and agency, why both of them rank freedom above everything else, and how each of them slips into scarcity mode when things get hard. The conversation turns practical as they unpack why they’re comfortable betting their time but cautious with cash, and what it means to grow without hiring or raising money. They close with the agreements they want to write down together, from an “enough” number to a plan for hard months.If you’re a co-founder who’s never had a direct conversation about money with your partner, a bootstrapped founder wrestling with when to spend to grow, or curious what coaching looks like for a business partnership- this episode is for you.All episodes of the podcast are also available on Spotify, Apple and YouTube.New to the pod? Subscribe below to get the next episode in your inbox 👇Want company-specific interview intel?If you’re preparing for PM interviews at Meta, Netflix, 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.Supra Insider listeners get $50 off all interview guides with promo code SUPRAINSIDER50In this episode, we covered the following topics:* (01:40) Jeff opens with a short mindfulness practice and a felt sense of “enoughness” around money* (08:16) The exercise: three questions on fear, desire, and love, and why co-founder and couples counseling are so similar* (10:29) Ben’s answers: his money fears, the image of always having a ticket on the train, and what he loves about Marc* (19:13) Marc’s answers: freedom, regret, the flexibility he wants money to buy, and what he loves about Ben* (30:44) Jeff’s three pillars: financial lineage, financial intimacy, and financial agency* (35:16) Where each co-founder could express more freedom, from fully disconnecting to creative work without a clear ROI* (47:43) Ben’s “high wire” feeling and how both founders slip into scarcity mode under stress* (56:45) Growing without hiring, raising, or compromising quality, plus Small Is Beautiful and the fisherman parable* (01:11:56) Entrepreneurship as betting: why they underprice their time, overprice cash, and need an experimentation budget* (01:26:47) What to codify in their partnership: an “enough” number, a “break the glass” plan for hard months, and scheduled appreciation* (01:32:36) Where to find Jeff: LinkedIn, jeffgreenberg.co, coaching, men’s groups, and financial therapy workshops* (01:34:08) Gratitude Corner: Jeff thanks three people:* his wife, Alessandra, for backing his move off Wall Street* his friends in Brooklyn* Seth, a mentor who also left Wall Street and started the weekly men’s group Jeff is part of* And more!Links: * Small Is Beautiful (E.F. Schumacher): https://www.goodreads.com/book/show/1117634.Small_Is_Beautiful* Alessandra Simone (Jeff’s wife): https://alessandrasimone.co* Jeff Greenberg (website): https://jeffgreenberg.co* Jeff Greenberg: https://www.linkedin.com/in/jeffdgreenberg/* Marc Baselga: https://www.linkedin.com/in/marcbaselga/* Ben Erez: 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:* Check out Ben’s AI Practice Copilot and top-rated Maven course: Self-Paced PM Interview Bootcamp: Product Sense & Analytical Thinking (selected by Lenny Rachitsky as a top course 🔥). Get 25% off the course with promo code suprainsider (auto-applied here).* 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% off some of these handpicked selections with code SUPRAxMAVEN. 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