CapLander

Four generations. Three strong women. One unforgettable conversation.

In this special episode of CapLander, Jody and Morgan welcome a very personal guest: Gail Kaplan, Jody’s mother, Morgan’s grandmother, and the outspoken matriarch of their family.

At 86 years young, Gail has a lifetime of wisdom, a remarkable perspective on how the world has changed, and absolutely no hesitation about sharing her opinions.

Together, thre...

What do you pack for a business trip—and what do you bring to the room once you get there?

Fresh from San Francisco and Palo Alto, Jody and Morgan Thelander unpack everything from repeat-worthy blazers and Silicon Valley style to the personal connections that keep business moving. They share why a genuine conversation can open doors, why successful founders keep building long after an exit, and why the follow-up matters just a...

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 practical and interpersonal ski...

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 professionals. It’s a conve...

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 new AI wealth in S...

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 touches on all the Thelander's favorite a...

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 Strategic Wealth Partners, for a conver...

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 while raising two kids under t...

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 Small Business Stock (QSBS). 

Dis...

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 revolutionizing the luxury consignment market, ...

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 her unique journey from law school t...

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 and insightful look at the entrepre...

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. John explains why emotional intelligence of...

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 founder dilution actually work, an...

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.

Julie discusses why giving ...

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 Bethenny Frankel and Dave Portnoy have built s...

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 brick-and-mortar and e-commer...

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 of fashion, luxury brands, and media, an...