In this episode, Jeff sits down with four-time entrepreneur Manny Menendez to talk about the choices that shape a career and the moments when you have to leap without perfect information.

Manny's path moves from the structure of large consulting firms to the chaos of early-stage startups. Along the way, he learned what changes when the infrastructure disappears, how to listen your way to product-market fit, and why belief, both in the mission and the team, can be the difference between a stagnant business and a breakout one.

This is a conversation about growth mindsets, scrappy beginnings, and the decisions that don't come with a clear answer.

Connect with Manny:

LinkedIn: Manny Menendez

In this episode, Jeff sits down with Ronald Diamond, founder and chairman of Diamond Wealth, to unpack the pivotal choices that shaped his journey from the fall of Drexel to building a $250 million hedge fund and a syndicate of over 100 family offices.

Ronald opens up about the tough decision to sell at the top, why most family offices fail, and why being a successful entrepreneur is more about emotional stamina than intelligence. He also shares hard-earned lessons about ego, purpose, and why money alone doesn't create a meaningful life.

If you've ever wondered when to stay the course, when to walk away, or what success really means, this conversation will give you a lot to think about.

Connect with Ronald:

LinkedIn: Ronald Diamond

Website: familyofficeworldmedia.com

This week, Jeff sits down with Marc Cabrera to unpack a career journey that spans Wall Street, burnout, entrepreneurship, and ultimately, a more intentional way of living and working. They explore the hidden tradeoffs of traditional success, the generational shift in how people think about careers, and why many high achievers feel stuck even after they've "made it."

This conversation is about more than career pivots. It's about redefining success, questioning inherited scripts, and learning how to make decisions that actually support the life you want to live.

Connect with Marc:

LinkedIn: Marc Cabrera

What started as a one-way ticket to Oaxaca turned into a global business built on trust, curiosity, and human connection.

This week, Jeff sits down with Zach Smith, founder of Anywhere, to unpack how a passion for immersive travel evolved into a purpose-driven company operating across more than 25 countries.

Jeff and Zach explore what it really means to build something slowly and intentionally, why authenticity beats scale-for-scale's-sake, and how patience, trust, and values-based decisions have guided Zach through nearly two decades of entrepreneurship.

Connect with Zach:

Website: anywhere.com

LinkedIn: Zachary B. Smith

Ashok Subramanian shares the real story behind leaving McKinsey, building Liazon from nothing, nearly running out of payroll multiple times, and ultimately selling the company in a lightning-fast acquisition that changed everything. Along the way, he reveals how founders misjudge risk, why most "great ideas" are actually wrong, and what it really takes to build something that lasts inside a broken healthcare system.

In this episode, Jeff Munn and Ashok unpack:

• Why the scariest part of entrepreneurship isn't failing — it's succeeding
• How Liazon pivoted from a dead-end pilot into a billion-dollar acquisition
• What founders get wrong about exits, risk, and building inside big companies

Whether you're starting your first company or scaling your fifth, this conversation will challenge how you think about risk, leadership, and what it means to truly build something.

The stakes only go up — but so does what you're capable of.

Guest: Ashok Subramanian
🔗 Centivo: centivo.com

Host: Jeff Munn
🎙 Pick Now Podcast
🔗 LinkedIn: jeffmunn

What if the biggest thing holding your business back… is you?

This week, Jeff sits down with Michael Pickel for a candid coaching conversation about leadership, control, and learning to get out of your own way. Michael reflects on overthinking decisions, being too hard on himself, and how unintentionally holding on too tightly can limit a team's growth.

Together, they unpack the difference between expectations and agreements, why control and growth can't coexist, and how real leadership often means creating space—for your team and for yourself.

What if the only thing standing between you and the opportunity of a lifetime is the belief that you belong there?
Norm Volsky shares how a career in recruiting turned into an entrepreneurial engine—helping scale category-defining healthcare companies like Livongo and Hinge Health, and eventually launching his own investment platform. Along the way, Norm reveals how conviction, timing, and relentless value creation compound into outsized impact.

In this episode, you'll learn:

• Why progress isn't linear—and why that's a good thing
• How betting on people early can change everything
• The mindset shift that turns "Why me?" into momentum
  
  

If you've ever felt on the edge of something bigger, this conversation might be the push you need.

What if the biggest career risk isn't starting a company—but never betting on yourself?

Matt Kuta shares why most people wildly overestimate the danger of entrepreneurship while ignoring the hidden instability of corporate life. Drawing from his journey as a fighter pilot, private equity investor, and founder who took a defense and space company public, Matt reframes risk, failure, and what it really means to live without regret.

In this conversation, Jeff and Matt explore why clarity beats comfort, how public failure is less dangerous than people think, and why building something uncertain can actually be the safest move of all.

Key takeaways include:

• Why staying at a "secure" company may be riskier than starting a business
• How entrepreneurs often have more clarity and control than corporate employees
• Why fear of public failure keeps talented people from ever starting
  
  

If you've ever felt stuck choosing safety over purpose—or wondered what future you might regret—this episode will challenge how you think about risk, courage, and career decisions.