In this episode, I’m joined by Jon Callaghan, co-founder and managing partner at True Ventures, and Julie Bornstein — CEO and co-founder of Daydream, founder of The Yes, and former COO of Stitch Fix — to break down what investors really evaluate in the first 18 months of a company’s life.

Drawing from their shared history as investor and founder, we talk candidly about runway, hiring before certainty exists, conviction versus ego, and how trust between founders and investors gets tested when plans change.

Julie explains how she approached budgeting and milestones for The Yes as a non-technical founder, while Jon shares how early-stage investors assess learning, decision-making, and leadership long after the pitch meeting ends.

RUNTIME 50:28 EPISODE BREAKDOWN

(2:43) Jon: “Julie and I met in graduate school.”

(4:24) Julie chose a different VC firm for her first seed round at The Yes

(10:33) How would Jon have assessed The Yes if he didn’t know Julie?

(13:14) Julie: “Runway is your best friend and your biggest gift.”

(14:59) How non-technical founders can sketch out a financial model

(22:37) Jon: “There’s an immense river of goodness that flows underneath Silicon Valley.”

(25:30) How did True Ventures size up SAM for The Yes?

(29:00) Only work with engineers who understand your problem

(31:25) Some of Jon’s post-check expectations for founders

(41:44) What are some questions founders should ask VCs in their first meeting?

(45:42) One experiment a pre-seed/seed-stage founder can try next week

(48:14) The final question

LINKS

Julie Bornstein
Jon Callaghan
True Ventures
Daydream
Top e-commerce veteran Julie Bornstein unveils Daydream—an AI-powered shopping agent that’s 25 years in the making, Forbes, 6/25/2025
Pinterest to Acquire THE YES, an AI Powered Shopping Platform for Fashion, press release, 6/2/2022
StitchFix

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Thanks for listening!

– Walter