Listen now: Spotify, Apple and YouTube

What does “AI-native” actually look like inside a company — not in theory, but in practice?In this episode of Supra Insider, Marc and Ben sit down with James Dillard, former YouTube and Stripe PM, who recently spent three months embedded at Roo Code, an AI-native startup building coding agents that can write and review production code.

James shares what it was like to join a 10-person team where everyone contributes to the codebase — from designers to community managers — and where the product process has been reimagined from the ground up.He walks through how discovery, design, and iteration actually work in an environment where code is the default language of collaboration — and what that means for the future of product management, engineering, and org design.

Whether you’re a product leader trying to make your org more AI-native, a founder exploring new operating models, or just curious about what “AI-native” means beyond the buzzwords — this episode offers a rare inside look at how the next generation of teams are really working.

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 👇

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:

* (02:12) What makes Roo Code different—minimal permission-seeking agents and rethinking team structure

* (04:34) How and why every team member ships code (even support and marketing)

* (08:33) Facing the fear of shipping your first PR as a non-engineer

* (12:30) How AI is breaking traditional GitHub PR flows with cheaper, more frequent pull requests

* (15:50) What a product development cycle looks like in an AI-native team

* (26:03) Design systems as strategic leverage—and who gets to shape them

* (35:59) Why defining the type of feedback matters more than ever

* (48:30) Guardrails and the need for new review patterns to handle contributor sprawl

* (52:27) Can non-AI-native companies adopt this way of working—or must they start from scratch? The 4-part framework.

* (58:55) Rethinking core PM values like “sell before you build” in a world where you can ship a prototype in minutes

* And more!

Links:

* James’s email: [email protected]

* James’s blog: https://www.jdilla.xyz/blog

* James’s YouTube Channel: https://www.youtube.com/@dangerously-skip-permissions

* James Dillard: https://www.linkedin.com/in/jamesdillard/

* 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

Listen now: Spotify, Apple and YouTube

If you’re a product leader wondering whether climbing the ladder is still the best path - or sensing a shift in where the real leverage is in the age of AI - this episode will change how you think about your role.

Gokul Rajaram (DoorDash board member, ex-Square, Google, Facebook) joins Marc and Ben for a powerful conversation about why many senior product leaders are stepping back into IC roles—and why that might be the smartest move you can make in today’s tech landscape. They unpack how the AI-native era has redefined leverage, why hands-on experience is critical to building credibility and staying relevant, and how the best PMs are evolving into multi-skilled builders who blend product, design, analytics, and engineering.

They also explore what great product execution looks like today, how to hire (or become) a truly modern product leader, and what to prioritize if you’re joining a breakout company in a fast-moving space.

Whether you’re a CPO, aspiring founder, or senior PM eyeing your next move, this conversation offers deep clarity on navigating your career in the AI era.

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 👇

Interviewing at Uber, Figma, or Stripe?

Exciting news! If you’re a PM preparing for interviews at Uber, Figma, or Stripe… 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:

* (01:22) Why many product leaders are returning to IC roles in AI-native companies

* (05:05) What founders get wrong when hiring Heads of Product too early

* (09:16) How product execution is evolving: prototypes over PRDs

* (22:15) Building features vs driving measurable customer outcomes

* (28:48) Why most CPO hires fail and how to promote from within instead

* (34:17) How to evaluate which company to join: mission, trajectory, talent density, founder courage

* (43:09) The importance of joining a company with high talent density and visionary leadership

* (51:47) Should you optimize for company moats early on? Gokul’s contrarian take

* (56:06) The power of low ego, high energy, and grabbing work no one else wants

* (1:03:22) Why gratitude fuels energy and career momentum

* And more!

Links:

* Gokul’s X: https://x.com/gokulr

* Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1/

* 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:

* 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 🔥

* 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.

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

Listen now: Spotify, Apple and YouTube

How do you disagree with your CEO, especially a visionary founder, without putting your job or credibility at risk?

In this episode of Supra Insider, Marc and Ben sit down with Elena Luneva (CPO, advisor, and executive coach) to unpack one of the most common, emotionally fraught challenges in product leadership: what to do when your CEO wants to change direction based on a gut instinct, and you disagree?

Drawing from Elena’s coaching experience and her own time leading product at high-growth companies, the conversation explores how to navigate power dynamics, set boundaries without losing trust, and protect team momentum amid constant change. They also share tactical frameworks for managing roadmap pivots, setting expectations with execs, and negotiating trade-offs when the team is already stretched thin.

Whether you’re a PM, product leader, or founder, you’ll walk away with practical strategies for navigating tough conversations, advocating for your team, and growing your influence, without losing your job or your sanity.

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 👇

Interviewing at Uber, Figma, or Stripe?

Exciting news! If you’re a PM preparing for interviews at Uber, Figma, or Stripe… 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:

* (00:35) Why this question resonates so deeply: “How do I manage a CEO who drives the roadmap by gut?”

* (05:20) The challenge of re-underwriting your mental narrative every time the CEO shifts direction

* (07:38) Why these moments can feel personal, even when they’re not?

* (12:28) Why your executive team, not just your builders, becomes your “first team” as a product leader

* (14:10) A playbook for responding to surprise roadmap changes: Listen, calibrate, and triage

* (19:54) Advice for CEOs: How to share ideas without shutting down your team

* (27:08) Using the Horizons framework to evaluate bets—and defuse emotional debates

* (34:31) The hidden costs of failed bets—and why many great PMs leave big companies to do risky work elsewhere

* (44:09) Giving CEOs the menu: options, trade-offs, and sunk costs

* (54:18) Why great product leaders should also validate gut instincts with market truths

* And more!

Links:

* Elena’s Course on AI Powered Executive Communication

* Elena’s Course on How to Develop CPO-Level Skills

* The Substack post that inspired this conversation: Your CEO Just Got Back From a Conference. Now What?

* Elena’s Letters: https://elenasletters.substack.com

* Elena’s LinkedIn: https://www.linkedin.com/in/elenaluneva/

* 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 get $100 off any of these handpicked selections with code SUPRAxMAVEN.

* Preparing for Meta-style PM interviews? Ben's course for Product Sense and Analytical Thinking PM interviews has been selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥. Enrollment for the 10th and final cohort of Ben’s course closes TONIGHT (Oct 13) and kicks of Oct 14. Ben’s popular AI Copilot for interview practice is available here.

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

Listen now: Spotify, Apple and YouTube

If you’ve ever considered turning your expertise into a scalable product—or wondered what it actually takes to build and sell a useful AI copilot—this episode is for you.

In this episode, Ben shares the full behind-the-scenes story of how he packaged his product management knowledge into a sellable, high-leverage AI Practice Copilot. From initial validation to prototyping in Claude to vibe coding in Cursor and shipping using various AI tools, he walks through every decision point in the journey. You’ll learn how to pick the right use case, what tools to use at each step, and the key insights that helped him turn his ideas into a real product in the market.

Whether you’re a founder, PM, coach, or subject matter expert, this conversation is packed with actionable tactics to help you create, position, and monetize your own AI-native product.

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 👇

Interviewing at Uber, Figma, or Stripe?

Exciting news! If you’re a PM preparing for interviews at Uber, Figma, or Stripe… 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:

* (02:28) Why Ben built his own AI copilot and the inspiration behind it

* (10:37) How Ben validated interest and clarified the user persona

* (16:40) Validation of the idea and selling via Payhip

* (20:26) The tools stack: from Claude, ChatGPT, Cursor and Vercel

* (27:11) How Ben used automations and AI to update the workflow and reduce manual overload

* (32:25) Why the copilot is built the way it is: AI acting as the “Interviewee”

* (46:10) An example of how the copilot responds

* (58:12) How the offering is packaged

* (1:06:09) The evolution of the copilot over time and why was it worth the effort

* (1:10:23) Final thoughts and advice for people building AI-native products

* And more!

Links:

* Ben’s AI Practice Copilot: https://www.benerez.com/copilot

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

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

* Ep 36 with Tal Raviv:

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:

* Preparing for Meta-style PM interviews? Ben's course for Product Sense and Analytical Thinking PM interviews has been selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥. Enrollment for the 10th and final cohort of Ben’s course starts October 14th! Ben’s popular AI Copilot for interview practice is available here, where you can also see a live demo.

* 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 get $100 off any 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

Listen now: Spotify, Apple and YouTube

What does it mean to truly be an “AI-native” company? And how are product roles evolving when PMs are expected to both execute faster and make sharper strategic decisions?

In this episode of Supra Insider, Marc and Ben sit down with Adam Fishman—host of the Startup Dad podcast and longtime product leader and advisor —to unpack the key themes from Reforge’s recent AI Product Summit in San Francisco. Adam shares insights from conversations with leaders at OpenAI, Anthropic, Shopify, Zapier, and LinkedIn on how organizations are tackling AI adoption, redefining PM expectations, and navigating cultural change.

The discussion ranges from Zapier’s live prototyping interviews for new hires, to LinkedIn’s shift from “product managers” to “product builders,” to the tension PMs face between increased executional leverage and the need for sharper strategic taste.

Whether you’re a PM figuring out how to stay relevant, a product leader navigating culture change, or just curious how AI is transforming product organizations, this episode is packed with lessons you can apply today.

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 👇

Interviewing at Uber, Figma, or Stripe?

Exciting news! If you’re a PM preparing for interviews at Uber, Figma, or Stripe… 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:

* (01:22) Adam’s reflections from Reforge’s AI Product Summit in San Francisco and the big themes leaders are wrestling with.

* (05:23) Zapier’s three levels of AI adoption—from ChatGPT tinkering to building workflows to submitting PRs in Cursor—and how they hire for it.

* (07:59) How Zapier reached 97% adoption by combining tools, leadership modeling, and performance management.

* (11:00) The risks of “shipping volume over quality” with AI, and why outcomes—not activity—must remain the north star.

* (14:25) Which PM responsibilities are fading (handoffs to analysts, UXR, or designers) and which are becoming core (strategy, judgment, taste).

* (22:50) The tension between increased execution leverage and rising expectations for strategic focus—why the PM role can feel “impossible.”

* (33:10) How cross-functional roles (support, design, marketing) are evolving when anyone can now build prototypes or tools with AI.

* (51:01) The future of specialization: why domain passion matters, but generalist builder skills may matter even more.

* And more!

Links:

* Fishman AF Newsletter: https://www.fishmanafnewsletter.com

* Startup Dad Podcast: https://www.startupdadpod.com/

* Adam Fishman: https://www.linkedin.com/in/adamjfishman/

* 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:

And here are some early favorites:

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 get $100 off any of these handpicked selections with code SUPRAxMAVEN.

* Preparing for Meta-style PM interviews? Ben's course for Product Sense and Analytical Thinking PM interviews has been selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥. Enrollment for the upcoming cohort starting October 14th is now open! Ben’s popular AI Copilot for interview practice is available here, where you can also see a live demo.

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

Listen now: Spotify, Apple and YouTube

What if interviewing for a PM job at Stripe, Uber, or Figma didn’t feel like walking into the unknown?

In this episode of Supra Insider, Marc and Ben take you behind the scenes of building Insider Loops—a new set of interview prep guides designed to give candidates the inside track at some of tech’s most competitive companies. They break down why they saw the opportunity, how they rapidly prototyped and shipped their first guides, and what they learned from dozens of conversations with PMs and hiring managers.

From uncovering hidden disconnects between great PMs and great interviewees, to the surprising differences in how Uber, Figma, and Stripe run their loops, this episode blends entrepreneurship, product thinking, and tactical job-search insights. Whether you’re preparing for your next role or just curious about how Marc and Ben collaborated async to launch a new product, you’ll walk away with practical takeaways and fresh perspective.

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 👇

Interviewing at Uber, Figma, or Stripe?

Exciting news! If you’re a PM preparing for interviews at Uber, Figma, or Stripe… 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:

* (04:11) The problem: talented PMs failing interviews not from lack of skill but lack of preparation.

* (11:18) The async workflow: GitHub repos, Cursor, and AI tools powering fast iteration.

* (30:29) How Marc & Ben priced the guides and why they offer lifetime updates.

* (40:50) The Uber guide: entropy in the jam, recruiter-as-Sherpa, and why overpreparing pays off.

* (52:23) The Figma guide: consensus culture, executive presence, storytelling, and collaboration signals.

* (58:40) The Stripe guide: product sense first, written culture, technical depth, and rigorous calibration.

* (1:08:15) Lessons learned, surprising insights, and admiration for PMs going through these loops.

* And more!

Links:

* Insider Loops: https://www.insiderloops.com/

* 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:

And here are some early favorites:

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

* Preparing for Meta-style PM interviews? Ben's course for Product Sense and Analytical Thinking PM interviews has been selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥. While the next cohort won’t be until mid-October, his popular AI Copilot for interview practice is available here, where you can also see a live demo.

* 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 get $100 off any 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

Listen now: Spotify, Apple and YouTube

What if personal finance wasn’t just about saving more or investing better—but about designing a life that feels meaningful, intentional, and aligned with your values?

In this episode of Supra Insider, Marc and Ben sit down with Zach Teutsch, founder of Values Added Financial, to explore a radically human approach to wealth management. Instead of fixating solely on net worth, Zach helps high earners and tech professionals reframe their relationship with money, starting with life satisfaction and working backwards from there.

They dive into the core questions that drive meaningful financial management, from how to balance ambition and family, to navigating equity compensation, sabbaticals, early-stage investing, and building a diversified “life portfolio.” Zach also shares tactical frameworks for spiky income years, Roth conversions, QSBS tax planning, and setting up estate plans that reflect your real priorities.

Whether you're in tech, product leadership, or just rethinking how you manage money, this conversation will shift how you think about personal finance—from accumulation to alignment.

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 👇

Interviewing at Uber, Figma, or Stripe?

Exciting news! If you’re a PM preparing for interviews at Uber, Figma, or Stripe… 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:

* (01:28) Why Zach’s framework for “values-aligned wealth” stood out from traditional financial advice

* (08:15) How fulfillment shows up through service, presence, relationships, and being “diversified” in life

* (17:11) The 3 life planning questions Zach asks every client—and how they unlock clarity

* (26:24) Why taking action now beats waiting for a million-dollar bank balance

* (33:42) Creating habits and systems to align your calendar with your values

* (41:12) Tactical financial “hacks” for tech folks: spiky income, Roth conversions, QSBS, and estate planning

* (49:03) What kind of professionals you really need in your corner as your wealth grows

* (56:30) Why everyone needs an estate plan—even if you don’t think you’re “rich enough” yet

* (1:07:50) Why the best advisors act more like therapists: it's not just finance, it's life design

* And more!

Links:

* Zach Teutsch: https://www.linkedin.com/in/zach-teutsch/

* Zach’s Email: [email protected]

* Zach on Bluesky: https://bsky.app/profile/zteutsch.bsky.social

* 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:

And here are some early favorites:

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 get $100 off any of these handpicked selections with code SUPRAxMAVEN.

* Preparing for Meta-style PM interviews? Ben's course for Product Sense and Analytical Thinking PM interviews has been selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥. While the next cohort won’t be until mid-October, his popular AI Copilot for interview practice is available here, where you can also see a live demo.

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

Listen now: Spotify, Apple and YouTube

If you’ve wondered how much AI is really helping engineers - or feared it might replace them - this episode is for you.

In this conversation, Marc and Ben sit down with Nick Meehan, a senior engineer and longtime collaborator, to explore how AI coding tools like Cursor, Claude, and Codex are reshaping day-to-day engineering work. Nick shares how his process evolved from copy-pasting into ChatGPT to using AI as a debugging partner, thought collaborator, and junior developer moving at superhuman speed.

They cover the productivity gains, the pitfalls of vibe coding entire products, the new skills engineers need (critical thinking, architecture, team coordination), and what might never be replaced by AI. Nick also reflects on job security, how satisfaction in engineering is shifting, and where he sees the field heading over the next five years.

Whether you’re an engineer experimenting with coding agents, a product leader trying to understand their impact, or simply curious about how AI is changing the craft of engineering, you’ll walk away with an insider’s perspective on what’s actually happening on the ground.

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 👇

✨ Special Surprise…

We have some exciting news to share! If you’re a PM preparing for interviews at Uber, Figma, or Stripe… 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:

* (03:40) Nick’s journey from copy-pasting into ChatGPT to discovering Cursor and pushing his team at Ontra to adopt it.

* (06:01) Defining pseudocoding vs. vibe coding—and where AI coding agents like Cursor, Claude, and Codex help or hurt.

* (11:40) The “magic moment” when AI solved frontend toil—and why backend work still demands human judgment.

* (15:31) Using AI as a thought partner and debugger: solving architecture problems and debugging in minutes instead of days.

* (20:00) Nick’s current workflow: step-by-step collaboration with AI, micromanaging it like a superfast intern.

* (30:19) Job security, critical thinking, and why learning to use AI is now a must-have engineering skill.

* (40:43) The enduring value of critical thinking, team coordination, and problem-solving that AI can’t replace.

* (58:35) Predictions: vibe-coded security disasters, a pendulum swing back to balance, and the rise of “cracked engineers.”

* And more!

Links:

* Nick Meehan: https://www.linkedin.com/in/nickmeehan/

* Nick’s zoom marketplace app: https://nextmeet.ing/

* 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:

And here are some early favorites:

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

* Preparing for Meta-style PM interviews? Ben's course for Product Sense and Analytical Thinking PM interviews has been selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥. While the next cohort won’t be until mid-October, his popular AI Copilot for interview practice is available here, where you can also see a live demo.

* 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 get $100 off any 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

Listen now: Spotify, Apple and YouTube

Think a “portfolio career” makes family life chaotic? Ben argues the opposite.

In this special episode of Supra Insider, Ben shares a more personal side of his journey in a conversation originally recorded on the Startup Dad podcast with Adam Fishman.

From raising his daughter Gaia (with help from George, the family’s golden retriever) to navigating solo parenting in New York without nearby family, Ben opens up about the joys and challenges of fatherhood. He reflects on why a portfolio career actually feels more stable than a full-time job, how intentional routines have transformed his days, and the lessons learned from mistakes, community, and the chaos of parenting.

If you’re a parent balancing an ambitious career, curious about the realities of raising kids in a big city, or simply want to hear a more personal side of Ben outside of product leadership, this episode offers candid stories, practical takeaways, and a heartfelt look at family life.

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 👇

In this episode, we covered the following topics:

* (01:47) George the golden retriever, Gaia’s favorite playmate, and the early days of parenting

* (05:01) “Children will destroy your life and replace it with a better one” — reframing priorities

* (08:30) How routines and compressed workdays reshape productivity as a parent

* (09:53) Building a portfolio career with multiple income streams and why it feels more stable than full-time work

* (22:25) Counterintuitive lessons from solo parenting and weekday vs. weekend dynamics

* (29:22) Surprising joys of fatherhood and the sense of belonging it brings

* (34:46) How structure and routines can be liberating rather than limiting

* (45:43) Dad groups, community, and why parenting overlaps with relationship growth

* (46:15) Technology, screens, and how the family navigates exposure for Gaia

* (51:16) Lightning round: indispensable products, funniest bribes, chaotic mornings, and signature dad superpowers

* And more!

Links:

* Startup Dad Episode with Ben:

* YouTube

* Spotify

* Substack

* Startup Dad Podcast: https://www.startupdadpod.com/

* Adam Fishman: https://www.linkedin.com/in/adamjfishman/

* 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:

And here are some early favorites:

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 get $100 off any of these handpicked selections with code SUPRAxMAVEN.

* Preparing for Meta-style PM interviews? Ben's course for Product Sense and Analytical Thinking PM interviews has been selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥. While the next cohort won’t be until mid-October, his popular AI Copilot for interview practice is available here, where you can also see a live demo.

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

Listen now: Spotify, Apple and YouTube

AI is transforming the way product teams approach customer research—but what should remain human, and what can be handed off to AI agents?

In this episode, Marc and Ben sit down with Aaron Cannon, co-founder of Outset, to explore the evolving role of AI in discovery and usability testing. Aaron unpacks how AI-moderated research enables unprecedented speed and scale while preserving depth, why intuition remains critical for building great products, and how research teams can shift from execution to framing the right questions and telling better stories. The conversation also dives into the future of PM and UXR roles, collective intuition at companies, and the career paths that might emerge as AI takes on more “entry-level” tasks.

Whether you’re a PM, designer, or researcher wondering how to integrate AI without losing the magic of human insight, this episode offers practical frameworks and a forward-looking perspective on what’s next.

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 👇

In this episode, we covered the following topics:

* (02:05) Why Aaron started Outset—and the research tradeoff between speed, scale, and depth

* (03:28) Two kinds of research: human-led improvisation vs. AI-led repeatable studies

* (07:34) How Outset keeps AI on-track with guardrails while still enabling deep exploration

* (12:14) The rise of iterative qualitative research—and how teams are testing and learning faster than ever

* (15:30) Why faster tools don’t mean you should ship more—just that you need stronger product judgment

* (19:13) How to structure product experiments as hypotheses to sharpen team intuition

* (29:40) The emerging role of UXR: from execution to storytelling, diplomacy, and company-wide insight building

* (42:46) What AI means for early-career UXR and PM roles—and how career ladders are being rewritten

* And more!

Links:

* Aaron Cannon: https://www.linkedin.com/in/a-a-ron-cannon/

* Outset: https://outset.ai/

* 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:

And here are some early favorites:

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

* Preparing for a PM interview with tech companies like Meta and Google? Ben's course for Product Sense and Analytical Thinking PM interviews has been selected by Lenny Rachitsky as a Top Course in Product on Maven 🔥. While the next cohort won’t be until October, his popular AI Copilot for interview practice is available here, where you can also see a live demo.

* 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 get $100 off any 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