CapLander

What does it actually take to stand out—in your career, in relationships, and in everyday life? In this episode of CapLander, Jody and Morgan have a wide-ranging conversation about effort, independence, and the increasingly underrated skill of knowing how to deal with people. They dig into a recent discussion about employers struggling with young workers entering the workforce without some of the...

What does it take to build a new home for the Buffalo Bills? ARC co-owner Cynthia Ciminelli joins Jody and Morgan to share the pride, teamwork, and community spirit behind the new stadium—and why its opening feels bittersweet for lifelong fans. Cynthia also talks about starting a business with her husband, finding her voice after a career in Washington, and what she looks for when hiring young pro...

Jody and Morgan sit down with Haley Schaffer, Founder and Managing Partner of Waypoint West, to discuss the financial and emotional complexities that come with building, managing, and transferring wealth. Haley explains why her firm acts as the “CFO of a client’s life,” helping families navigate investments, taxes, trusts, estate planning, and major liquidity events. They explore the explosion of...

The standards we set in one part of our lives tend to show up everywhere else. Jody and Morgan discuss adjusting to life with a newborn, learning when to offer advice (and when to let it go) and creating routines that make new chapters manageable. They discuss AI's growing role in privately held companies, the importance of having trustworthy data, and where Thelander comes in. This episode to...

Morgan is back—just three weeks after welcoming her daughter! She and Jody share the emotional story of her breech delivery, unexpected C-section, early motherhood, and the family support that carried her through it.

This episode originally aired on March 17, 2026, and is being re-released as part of our Best of CapLander series, highlighting some of our most popular and impactful conversations. What does real wealth actually look like when you strip away the buzzwords? In this episode, Morgan and Jody sit down with longtime friend and finance powerhouse Christine Leong Connors, co-founder and CEO of Verita St...

This episode originally aired on Apr 21, 2026, and is being re-released as part of our Best of CapLander series, highlighting some of our most popular and impactful conversations. What does it take to go from first employee at a hyper-growth media startup to founding a consumer brand, landing a deal on Shark Tank with Mark Cuban, and pivoting into angel investing and real estate development — all...

This episode originally aired on February 2, 2026, and is being re-released as part of our Best of CapLander series, highlighting some of our most popular and impactful conversations. In this episode of the CapLander podcast, hosts Jody and Morgan Thelander sit down with Alessandro Chesser, founder & CEO of GetDynasty to discuss how they help startup founders pay zero taxes through Qualified S...

This episode originally aired on October 27, 2025, and is being re-released as part of our Best of CapLander series, highlighting some of our most popular and impactful conversations. In this episode, Jody and Morgan Thelander are joined by the one and only, Julie Wainwright, founder & former CEO of The RealReal. From navigating the challenges of the dot-com bubble with pets.com to revolutioni...

This episode originally aired on January 12, 2026, and is being re-released as part of our Best of CapLander series, highlighting some of our most popular and impactful conversations. Join Jody and Morgan as they are joined by Ali Murata, compensation and benefits partner at Cooley. Ali shares her insights on the evolving compensation landscape, the strategic role of legal advice in business, and...

What does it really take to turn a side hustle into a thriving consumer company?  Lindsay Droz , Co-Founder at  L'AVANT Collective , joins Jody and Morgan to share the story behind building a premium, plant-based home cleaning product company from the ground up. From bootstrapping the business while working full-time careers to scaling a brand with a cult-following, Lindsay shares an honest an...

What really goes into executive compensation at one of the world's largest financial institutions? John Trentacoste shares his journey from advising corporate boards to leading executive compensation initiatives at Goldman Sachs, offering a behind-the-scenes look at how incentive plans, equity, and carried interest shape leadership decisions. But this conversation goes beyond spreadsheets. Joh...

What does it really mean to be an entrepreneur in today's economy? In this episode, Jody and Morgan explore how entrepreneurship has evolved—from side hustles and online businesses to venture-backed startups—and why more people than ever are looking beyond the traditional 9-to-5. They discuss the mindset successful founders share, the realities of raising venture capital, how equity and founde...

What separates good CEOs from truly exceptional ones? Executive coach and CEO advisor  Julie Jackle  has spent 17 years helping founders and executives navigate the toughest stages of growth—from building their first leadership team to leading billion-dollar public companies. In this episode, she shares the leadership habits that consistently separate successful CEOs from those who get stuck. Juli...

What do startup equity, social media influencers, luxury brands, and handwritten thank-you notes have in common? More than you might think. Jody and Morgan begin by unpacking the latest conversation around QSBS trust stacking and why founders need to ensure they're earning the right equity before they start planning how to preserve wealth. From there, they explore why entrepreneurs like Bethen...

Irish-born entrepreneur Margaret O’Leary joins CapLander to share the story behind the knitwear company that bears her name. From arriving in San Francisco with a deep knowledge of sweaters to growing a beloved retail brand with 14 stores, Margaret reflects on entrepreneurship, fashion, motherhood, and staying true to her vision. Jody and Morgan discuss the evolution of retail, the balance between...

Troy Alexander's life changed forever after a college fight landed him in prison. What could have become the defining mistake of his life instead became the foundation for everything that followed. In this episode, Troy shares how two years of incarceration taught him resilience, discipline, and the power of mindset. He opens up about rebuilding his life from scratch, breaking into the worlds...

In this episode of CapLander, Morgan and Jody discuss the realities of entering today’s competitive job market—and why some of the simplest professional habits still make the biggest difference. From showing up on time and learning from demanding mentors to networking in unexpected places and pursuing opportunities in the startup world, they explore the mindset that helps young professionals stand...

Venture capital has evolved from a cottage industry into a global ecosystem—and the next generation of investors is reshaping what comes next. Chris Harvey, founder of Harvey Esquire, joins Jody and Morgan to discuss the rise of emerging fund managers, why firms like Andreessen Horowitz changed the venture landscape, and how AI is influencing everything from investment decisions to firm operations...

This week on CapLander, Jody and Morgan sit down with EO Products co-founder and co-CEO Susan Griffin-Black to talk about building one of the original natural personal care brands decades before “clean beauty” became mainstream. From launching EO in Marin County in 1995 to creating the massively successful Everyone line, Susan shares how intuition, authenticity, and long-term thinking helped grow...

Morgan and Jody check in from the Blue Ridge Mountains and cover everything from airport travel and luxury stroller shopping to the changing future of startups, venture capital, and leadership. Along the way, they unpack why smaller companies are becoming more powerful, how AI is reshaping entrepreneurship, and why the next generation of founders will need grit, adaptability, and relentless focus...

In this episode of CapLander, Jody and Morgan discuss the spirit of entrepreneurship and leadership with David Stine and Stephanie Abbajay - while digging into the realities of what it's like working with your spouse. David shares how he left a successful law career and turned his woodworking hobby into a pursuit of excellence, becoming a featured exhibitor at the Architectural Digest Design S...

Morgan and Jody recap a work trip to Austin, Kentucky Derby upsets,  The Devil Wears Prada , a The Wall Street Journal breakdown of high-earning women, and Belle Burden's memoir—on the surface, they don’t seem connected. But together, they point to one idea: the top 1% is built through accumulated steps, not isolated wins. We talk through how careers actually compound over time, and how the de...

From a small-town gas station to the front lines of luxury resale, Ashley Maurice’s journey into fashion is anything but typical—and that’s exactly why her perspective cuts through the noise. In this CapLander episode, Ashley (Manager of Buying at The Vault Luxury Resale) breaks down what actually holds value in today’s resale market—and what doesn’t. From Hermès Birkins outperforming traditional...

What does it take to go from first employee at a hyper-growth media startup to founding a consumer brand, landing a deal on Shark Tank with Mark Cuban, and pivoting into angel investing and real estate development — all while raising two kids under two? Kaylin Roche has done exactly that, with intention every step of the way. Jody and Morgan sit down with Kaylin to trace the through-line of a care...