Stashing Acorns: Building & Managing Wealth with Haley Schaffer

What happens when Target asks for half a million pizzas in 90 days?Katie Lee joins Jody and Morgan in St. Louis to share the story behind Katie’s Pizza & Pasta and its expansion into 8,000 retail locations. From rebuilding her life in recovery to crowdfunding her restaurant and pivoting to frozen pizza during COVID, Katie discusses the resourcefulness, discipline, and risk-taking behind her growth.They dig into the realities of scaling a food business, rewarding a talented team, negotiating with major retailers, and weighing outside capital against independence. Plus, Katie shares how gratitude, creativity, personal style, and time in nature keep her grounded through it all.

Motivation comes and goes. Discipline is what gets you back in the pool—and keeps you moving forward in business.In this episode of CapLander, Jody and Morgan welcome Holly Welch, a former collegiate swimmer, swim coach, and Marin County real estate professional. Holly shares how training alongside elite athletes shaped her approach to competition, setbacks, and starting a new career at 47 after more than a decade as a stay-at-home mom.From putting her ego aside to learn the business to turning years of community involvement into lasting client relationships, Holly offers a practical look at building a career from the ground up. They discuss why discipline beats motivation, how to learn from failure, and why you’re rarely starting with as little experience as you think.They also explore how AI wealth is influencing Marin County’s housing market, the value of local expertise, and making room for family—and a victory lap—along the way. Holly’s guiding reminder ties it all together: “I can do hard things.”00:00 Welcome and Why Marin County06:34 Holly’s Background08:38 Building Discipline Through Sports13:16 From Athlete to Professional16:47 Learning from Failure and Setting Goals21:21 Building a Real Estate Career25:41 Career Lessons and Partnerships26:50 Navigating Marin Real Estate30:29 What Makes Marin Unique32:21 How the AI Boom Affects Real Estate36:52 Looking Ahead

What does it take to build a successful career, a thriving business, and a marriage that lasts nearly 50 years?Jody and Morgan Thelander welcome James S. Cassel, Chairman and Co-Founder of Cassel Salpeter, a Miami-based investment banking firm, for a wide-ranging conversation about business, relationships, and the lessons learned along the way.James shares his unconventional journey from practicing law for 17 years to leading an investment banking firm, why relationships and networking remain essential to business success, and the emotional complexities of selling a family-owned company.The conversation also gets personal as James reflects on nearly five decades with his wife, raising four children while building his career, and why helping others without expecting anything in return can pay dividends for years to come.Plus, they explore the value of traditional education in the age of AI, the outlook for mergers and acquisitions, and whether the current AI boom might be getting ahead of itself.From billion-dollar ideas to grocery-store introductions and the great carry-on luggage debate, this episode is a reminder that business is ultimately about people.

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, three generations of women explore the lessons, values, and experiences that have shaped their family—from building a career at a time when few women worked outside the home to navigating marriage, motherhood, financial independence, and the sometimes complicated dynamics of working with family.Gail reflects on her 66-year marriage, her lifelong love of travel, and the importance of saving, investing, and living within your means. Along the way, the conversation takes plenty of hilarious detours through family disagreements, forgotten birthdays, and the unmistakable personality traits passed down through generations.With the recent arrival of Morgan’s daughter Peyton bringing a fourth generation into the family, the conversation ultimately turns to legacy: what we inherit, what we choose to carry forward, and what really matters in the end.Funny, candid, heartfelt, and full of hard-earned wisdom, this episode is a celebration of strong women, family bonds, and the lessons that connect generations.

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 as much as the introduction.Back in St. Louis, life is changing, too: Morgan is navigating her first business trip since becoming a mom, and Jody is setting up a home base around the corner. Along the way, they debate sandwiches at cocktail hour, compare perfectionism with living comfortably at 80%, and reflect on how they keep their mother-daughter relationship strong while running a business together.It’s a candid, funny conversation about showing up, letting go, and making room for what matters—in your suitcase, your career, and your family.

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.