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 practical and interpersonal skills they expect. But rather than simply blaming a generation, Jody and Morgan look at the bigger picture: Are schools preparing young people for the real world? Are parents giving their kids enough opportunities to become independent? And how much of professional success comes from skills you can only learn by actually working?

From customer-service jobs and difficult conversations to taking initiative when nobody asks you to, they explore the experiences that teach you how to solve problems, communicate with people, and become someone others can rely on.

Morgan also shares an update on life as a new mom—including the realities of breastfeeding, sleepless nights, and a dog adjusting to no longer being the center of attention—and somehow the conversation even finds its way to personal style, hobbies, networking, and why getting away from a screen and interacting with actual humans still matters.

It’s a conversation about growing up, standing out, and why getting where you want to go usually requires more than simply doing what’s expected of you.

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 conversation about partnership, believing in your work, and the people who make Buffalo feel like home. Go Bills!

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 San Francisco, the danger of treating paper wealth like real money, and why diversification can be psychologically difficult after one investment has created enormous success. Haley also pushes back against social media’s side-hustle culture, sharing how disciplined, passive investing can quietly compound into meaningful generational wealth.

The conversation also gets personal as Haley discusses founding Waypoint West with her brother, the boundaries and honest communication required to make a family business work, and why relationships, integrity, and purpose—not a balance sheet—ultimately create a rich life.

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 areas, including what they're shopping for. 

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 Strategic Wealth Partners, for a conversation that goes far beyond money management. Christine breaks down what a modern multifamily office really does, why so many high-achieving individuals still lack a clear picture of their financial lives, and how strategy, technology, and trust come together to create real clarity.

But this episode is about more than balance sheets. Christine also talks about building a company from the ground up, leading with culture, navigating motherhood and marriage while running a fast-growing business, and why confidence, purpose, and self-love may be the most important forms of wealth of all.

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 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 career built on timing, brand instinct, and a willingness to walk through the door even when you're scared. From scaling theSkimm from 100,000 to 8 million subscribers, to launching JIGGY Puzzles four months before COVID accidentally made it a cultural moment, to revitalizing Buffalo's historic Allentown neighborhood — Kaylin brings the kind of founder clarity that only comes from having actually done it. The conversation gets real on bootstrapping vs. raising capital, knowing when to sell, why brand identity isn't something you can fully outsource, and the "founder mom pilot era." If luck is just what happens when experience meets opportunity, Kaylin has put herself in position for a lot of it.

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). 

Discover how Alessandro's journey from banking to tech led to the creation of a full-stack trust company aimed at reducing taxes for entrepreneurs. Learn about the pivotal moments that shaped his career, the challenges of balancing family and business, and the future of wealth management in the startup ecosystem. Whether you're a seasoned founder or just starting out, this episode offers valuable insights into maximizing your financial potential.

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, Julie shares her insights on resilience, innovation, and the power of grit. Discover how she turned setbacks into stepping stones and built a billion-dollar business, all while staying true to her entrepreneurial spirit.

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 to becoming a trusted advisor in Silicon Valley. Join us for an engaging discussion on the challenges and opportunities in today's corporate world - and why the short game matters so much more than one good drive.