But what happens when your identity becomes your company?

In this episode, Chip Conley, founder of a hotel hospitality group and mentor to Airbnb’s CEO, shares the realities most founders don’t talk about.

We cover:

• Why tying your identity to your start-up can be dangerous
• The emotional toll of building, and what happens when things fall apart
• Lessons from mentoring Brian Chesky at Airbnb
• How to lead without ego and empower your team
• What comes after success, burnout, or exit

This is a candid conversation about leadership, resilience, and building a life beyond your company.

In this episode, Eric Berry, founder of TripleLift and co-founder of Averin, shares the unfiltered story behind one of ad tech's most unlikely exits. From pivoting seven times in an accelerator to building a $1.4B company with just $17M raised, Eric breaks down what it actually takes to back yourself when the people funding you disagree.

In this episode:

• How TripleLift grew at 200%+ year over year while staying capital efficient
• The "right to play, right to win" framework Eric now uses to evaluate healthcare investments
• What early stage investors are actually betting on, and it's not your idea
• Why AI is a tailwind for some companies and a headwind for others

Eric Berry is the co-founder and former CEO of TripleLift, acquired by Vista Equity Partners for $1.4B in 2021. He is now co-founder of Averin, a venture firm investing in AI-driven healthcare technology.

Learn more about Founders Network at foundersnetwork.com

In this episode, Guy Nirpaz, the creator of Totango, the company that invented the customer success category, shares why he started a new company after raising $149M and scaling to 20 million users, and what he believes the industry still hasn't solved.

In this episode:

• The Customer Momentum Loop, Guy's new framework for staying aligned with customers at AI speed
• Why "forward deployed engineers" are really plumbers connecting companies to the token pipeline
• What Guy told his daughter when she asked how he keeps going without knowing if it'll work
• Why every AI agent needs to operate in "founder mode"
• Guy's honest take on where AI hype ends and real defensibility begins

Guy Nirpaz founded Totango, and scaled it to 20 million users across 2 million businesses. He is now founder and CEO of Perspective AI, building AI-powered CX agents. Get started at getperspective.ai.

Learn more about Founders Network at foundersnetwork.com

So what actually matters now?

In this episode, Guy Yalif, co-founder of Intellimize (acquired by Webflow) and former marketing leader at Twitter and Yahoo, breaks down what really drives durable growth in today’s environment.

We cover:

• Why product is no longer a sustainable moat
• What actually is defensible: brand, distribution, data, and switching costs
• The “15 conversations” framework for validating ideas
• How founders fall into the trap of false validation
• Why listening to customers beats moving fast

This is a practical conversation about building, validating, and growing a start-up when the rules are changing, but the fundamentals still matter.

We talk about what it actually took to get momentum (credibility, distribution, and relentless customer feedback), why Zapier leaned into an integration flywheel, and how building relationships created “surface area” for unexpected breakthroughs—like discovering your biggest customer is in Austria.

Then we zoom out: what generative AI changes (and doesn’t), why the next era may be more about context + judgment than raw code output, and how founders can stay grounded while the tools get wildly more powerful.

Show Notes

What we cover

• A Midwest upbringing, engineering school, and the post-2008 job market reality
• The “magic moment” of the internet: realizing your customers can be anywhere
• Where the Zapier idea came from: forum threads full of “plus one” requests
• Early product-building: nights/weekends, staying skeptical, and watching real usage
• Credibility and distribution: why being vouched for matters with bigger partners
• The mindset shift: actively seeking real negative feedback (instead of polite nods)
• The integration growth loop: why “more integrations → more growth” became the model
• Remote hiring lessons and building culture outside Silicon Valley defaults
• AI and the future: vibe coding, judgment, and the “context engine” problem

In this episode, Barbara, co-founder and COO of SafetyPay (acquired by PaySafe for $441M) and Managing Partner at Seedfunders, shares the unfiltered story of what it actually takes to build and survive a decade-long startup journey.

We cover:

• How SafetyPay nearly died seven times and what kept the team going
• Building a company with your spouse: what works, what doesn't, and why complementary skills matter
• Why drip funding kept them on the edge and how they finally broke through
• The PR and go-to-market tactics that built credibility with no budget
• What Barbara now looks for in early-stage founders as an investor
• Why skin in the game matters more than the size of your salary

This is a raw and honest conversation about endurance, commitment, and what never giving up actually looks like in practice.