What does it look like to build a business—and an investment strategy—designed to weather the storm?

In this episode of At Depth, Ben Rodgers sits down with Stephen Lowry, founder of Redbeard Capital, to unpack the lessons behind a career in entrepreneurship, family offices, alternative investments, and building alongside the right people. From selling cassette tapes in grade school to running a gopher-killing business and eventually investing in businesses and real estate, Stephen shares how starting small, proving a concept, and creating real value shaped his approach.

The conversation goes deeper into Stephen's philosophy on growth, partnership, profit, and risk. Why does he believe businesses are either growing or dying? Why does Redbeard prioritize all-cash investments and start with the worst-case scenario? And how do you balance financial performance with building a business where people can actually thrive?

It's a candid conversation about entrepreneurship, investing, relationships, and the long game—and why sometimes the smartest move is to slow down, de-risk, and give yourself room to win.

What if the biggest obstacle to your leadership isn't your strategy—it's the story you're telling yourself?

Executive coach Greg Taylor has spent decades helping leaders, entrepreneurs, and high-performing teams operate closer to their potential. In this conversation with Ben Rodgers, he shares the hard-earned lessons that transformed him from a leader driven by proving himself into one committed to serving others.

Together, they explore why success and fulfillment aren't the same thing, how self-awareness changes the way we lead, and why the best coaches don't hand out answers—they help people discover their own. Greg opens up about business failure, identity, family, and the moments that reshaped how he approaches leadership, relationships, and purpose.

This episode is a conversation about becoming the kind of leader people want to follow: someone who listens before speaking, builds trust before demanding results, and understands that lasting growth starts from the inside out. As Greg puts it, fulfillment comes when what's been placed inside you finds its way into the world.

In this episode:

• Why success without purpose eventually feels empty

• The difference between coaching, mentoring, and fixing people

• How self-awareness unlocks better leadership

• Building trust through questions instead of answers

• The "one domino" philosophy for creating lasting change

If you're building a business, leading a team, or simply trying to become a better version of yourself, this conversation offers practical wisdom for the journey.

Financial planning isn't really about spreadsheets. It's about creating the space to ask a deeper question: How do you want to live your life?

In this episode of At Depth, Ben sits down with Jenn Lane, founder of Compass Planning and one of the early pioneers of fee-only financial planning. Jenn's path—from flight instructor to financial planner—reveals a simple but powerful philosophy: the best financial advice starts by understanding the person, not the portfolio.

Together, they explore why most people don't actually need better financial products—they need time to think, honest conversations with the people they love, and someone who can hold the bigger picture when life gets noisy.

Along the way, they discuss:

• Why our biggest financial challenge isn't investing—it's talking about money.

• How financial planning creates space for couples to discover what they really want.

• The surprising freedom that comes from simply knowing where your money goes.

• Why truth—not sales—is the foundation of good advice.

• What it feels like to walk alongside clients through decades of life's biggest milestones.

This is a conversation about money, but even more, it's a conversation about clarity, trust, and building a life that aligns with what matters most.

If you've ever felt overwhelmed by financial advice—or wondered whether your money is actually serving the life you want—this episode is for you.

What separates high performers from everyone else? According to Paige Good, it isn't a better script, more leads, or another productivity hack.

As Learning Advisor for Sotheby's International Realty, Paige has spent nearly three decades helping agents build businesses that last. In this conversation, she and Ben explore why sustainable performance starts long before the transaction—with mindset, intentional habits, authentic relationships, and the courage to build a framework instead of simply staying busy.

They discuss:

• Why relationship-building still outperforms transaction-chasing

• The hidden cost of operating without a personal framework

• How fear, imposter syndrome, and negativity quietly limit growth

• The discipline of protecting your time while serving clients well

• Why integrity, kindness, and authentic connection remain enduring competitive advantages

Whether you work in real estate, investing, sales, or any business built on trust, this episode offers a practical conversation about what it takes to perform consistently without losing the human side of your work.

At Depth explores the ideas, values, and relationships that shape how leaders, entrepreneurs, and investors build businesses—and lives—that endure.

What if the most valuable asset you own isn't your money—it's your attention?

In this episode of At Depth, Ben Rogers sits down with entrepreneur, investor, educator, and family office advisor Alex Felman to explore the intersection of relationships, business, personal growth, and human connection.

Together, they unpack the challenge of maintaining meaningful relationships in a world built for scale, diving into concepts like Dunbar's Number, parasocial relationships, and how podcasts can strengthen connections across distance and time. They also examine the modern attention economy, why intentionality matters more than ever, and how investing your attention in the people closest to you may be one of the highest-return decisions you can make.

The conversation then shifts to entrepreneurship—not as a path to unicorn valuations, but as a vehicle for creativity, freedom, experimentation, and personal agency. Alex shares his framework for becoming the "1% version of yourself" by combining unique skills, embracing iteration, and focusing on the intersection of your strengths rather than chasing perfection in a single domain.

Whether you're building a business, cultivating deeper friendships, or searching for greater clarity in your work and life, this episode offers practical wisdom and thought-provoking ideas that challenge conventional definitions of success.

In this episode:

• Why meaningful relationships don't have to disappear at scale

• Dunbar's Number and the limits of human connection

• The hidden cost of the attention economy

• How podcasts create and maintain relationships

• Entrepreneurship as a sandbox for creativity and growth

• The power of skill stacking and becoming the "1% version" of yourself

• Why focus—not talent—is often the greatest challenge

A conversation about connection, contribution, and building a life that aligns with what matters most.

What separates founders who build extraordinary companies from those who don't?

In this episode of At Depth, Ben Rodgers sits down with venture investor and entrepreneur Nadav Eylath to explore the mindset behind identifying opportunity before it's obvious. Drawing on decades of experience as a founder, operator, and investor across Silicon Valley and Israel, Nadav shares what he's learned about recognizing exceptional people, navigating uncertainty, and creating the conditions for outsized outcomes.

Their conversation moves from surfing in Tel Aviv and California to venture capital, startup culture, and the surprisingly human skills that drive long-term success. Nadav explains why great founders learn and adapt faster than everyone else, why focus remains a competitive advantage in an age of distraction, and why some of the most important breakthroughs happen in the unplanned moments between meetings.

Along the way, they discuss failure, delegation, building trust, the unique culture of Israeli entrepreneurship, and the importance of staying open to possibilities others can't yet see.

In this episode:

• Why venture capital is really about "seeing what's possible"

• What surfing taught Nadav about risk, patience, and pattern recognition

• The founder trait most correlated with long-term success

• Why focus is becoming more valuable, not less

• The hidden advantages of working together in person

• Lessons from investing in companies that became category leaders

• How investors and founders can think differently about opportunity

This is a conversation about vision, execution, and the courage to pursue possibilities before the rest of the world believes they're real.

What actually makes someone trustworthy in business?

In this episode of At Depth, Ben Rodgers and Danny Burbeck explore the tension between professionalism and authenticity — and why the people we trust most are often the ones willing to admit failure, share disappointment, and stay human in the middle of pressure.

The conversation moves through investing, leadership, entrepreneurship, listening, and the quiet loneliness that often comes with responsibility. Ben and Danny unpack why depth feels so rare in modern work culture, why most conversations stay on the surface, and what changes when leaders genuinely give their attention to the people around them.

They discuss:

• why success without people to share it with feels empty

• how failure reveals character faster than success

• the hidden cost of “professionalism”

• why listening is one of the most undervalued leadership skills

• how great leaders create teams people actually want to belong to

• why curiosity sits at the center of meaningful relationships

This is a conversation about more than business. It’s about what happens when people stop performing and start showing up honestly — for their teams, their partners, and themselves.

If you’ve ever felt exhausted by surface-level networking, scripted conversations, or transactional leadership, this episode will feel like fresh air.

What does it actually mean to build a life—not just a portfolio?

In this conversation, Ben sits down with his dad, Ray Rodgers—investor, operator, and founding member of CovePilot—to explore the ideas that have quietly shaped decades of investing, decision-making, and life in a small Texas town.

From early days structuring real estate deals across the country… to building a life rooted in simplicity, stewardship, and long-term thinking… this is a conversation about the tension between sophistication and simplicity—and why the two aren’t opposed.

They unpack the philosophy behind CovePilot: investing in real assets, keeping things intentionally small, and operating away from the noise— not as a strategy for optimization, but as a way to stay grounded in what actually matters.

Along the way, they explore:

• Why “simplicity is the highest form of sophistication”

• The difference between ownership and stewardship

• How small, steady decisions compound over time

• The hidden cost of complexity and the pull of the crowd

• What it looks like to build wealth and a meaningful life

This isn’t a conversation about chasing returns.

It’s about building something that lasts— and knowing why you’re building it in the first place.

[email protected]

What if the most important signals in life — and business — aren’t found on spreadsheets, dashboards, or market reports… but in the body, in nature, and in the patterns we’ve stopped paying attention to?

In this episode of At Depth, Ben Rodgers sits down with Natalya Wallin — founder of Vitality Venture Fund, systems thinker, ultra-runner, and former global fund builder — for a conversation about intuition, resilience, biomimicry, and the hidden architecture behind meaningful work.

Natalya shares the story of a single sentence from a mentor that completely changed the trajectory of her life, taking her from molecular genetics into global policy, venture investing, and building solutions inspired by nature itself. Together, Ben and Natalya explore what it means to think in systems, how great teams function like orchestras, why ambiguity is necessary for innovation, and how our bodies often recognize truth before our minds can explain it.

This conversation moves from the bottom of the Grand Canyon to the future of regenerative investing — touching on entrepreneurship, leadership, intuition, founder psychology, human connection, and the cost of ignoring the signals trying to guide us.

Topics include:

• Systems thinking and “mutant generalists”

• Biomimicry and nature-inspired investing

• Building Vitality Venture Fund

• Intuition, somatic awareness, and decision-making

• Why in-person relationships still matter

• Founder conviction and recognizing authentic vision

• Endurance training as preparation for life

• The hidden cost of clarity, ambition, and misalignment

This isn’t just a conversation about investing. It’s about learning how to pay attention.

What happens when success on paper no longer matches the life you want to live? In this conversation, Morgan Keim shares his shift from venture-backed scale to a more intentional path—what he calls “quiet wealth.” We explore discernment, identity, family, investing with conviction, and how to align your work, capital, and life without losing yourself along the way.