CapLander

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 to survive.

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 Show for 13 years straight. From balancing risk and family to supporting each other through growth and uncertainty, this episode explores the human side of entrepreneurship - and what it really takes to build a business, one bench at a time. 

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 decisions you make along the way matter more than any single outcome. Outcomes are visible—but accumulation is what drives them. 

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 investments to why Chanel’s black-and-gold classics dominate, this conversation goes beyond hype and into real-world buying behavior.

The group digs into the surprising resurgence of brands like Coach, the rise of “dopamine dressing,” and the ongoing battle between quiet luxury and bold monograms. They also unpack the psychology behind why some items get flipped while others are held for years—and how trends cycle faster than ever.

If you’ve ever wondered whether luxury goods are truly an investment—or just really expensive taste—this episode gives you the framework to think about it smarter.

Because in resale, timing matters… but knowing what to buy matters more.

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.

Geoff Meyerson didn’t just choose a career—he built one. From investment banking and venture capital to launching Locust Walk the day Lehman Brothers collapsed, Geoff shares how betting on himself led to a 17-year nonlinear journey at the center of biotech dealmaking. This episode dives into what it really means to “zig when others zag,” why Boston still matters (but isn’t untouchable), and how China has become impossible to ignore in global biotech.

Along the way, Geoff breaks down the evolving role of AI in life sciences, what actually matters when hiring (hint: it’s not your degree), and why showing up—physically and consistently—is still the ultimate competitive advantage. The conversation weaves between business, family, and the realities of building something from scratch, with plenty of humor about everything from packing strategies to performance reviews…including giving one to your own mom.

This week on CapLander, Jody and Morgan kick things off with a brutally honest look at accountability—why a simple “I screwed up” is so hard to say, and why it matters more than ever. From there, they dive into a provocative Wall Street Journal piece on AI founders dropping out of elite schools while venture capitalists foot the bill. Is this the ultimate fast track—or a shortcut with long-term consequences?

The conversation expands into the real cost of skipping traditional paths: missed structure, underdeveloped social skills, and the question no one wants to answer—what happens if it doesn’t work? Drawing from personal experience, parenting philosophy, and years in business, Jody and Morgan unpack the trade-offs between speed and stability, independence and guidance, risk and responsibility.

They round things out with a rapid-fire take on current trends—from controversial car tech to spring fashion and the evolving definition of value (yes, including diamonds). It’s a wide-ranging, sharp-edged conversation about ownership, boundaries, and the reality that every decision—whether in business or life—comes with a price.

Nate DaPore, founder and managing partner of Roo Capital, joins Jody and Morgan to share how he built a venture firm centered on talent, conviction, and a “who not how” mindset. He explains how his firm blends investing with in-house recruiting to create real value for founders, and why surrounding yourself with the right people is the ultimate advantage in today’s market.

The conversation also explores how AI is reshaping venture and why proprietary data and strong teams still win. On a personal level, Nate opens up about the systems he and his husband use to stay grounded—like annual themes and solo retreats—while managing a demanding travel schedule and building a life together.

It’s a candid look at scaling a firm, building a life, and staying anchored in what matters most.

What happens when biotech, spirituality, and real life collide? You get Rabbi Brian.

In this episode, Morgan and Jody sit down with Brian Denker—conference leader at BioCentury and a rabbi serving interfaith and modern families—for a conversation that goes well beyond a typical career path. After a deeply personal rejection when trying to get married, Brian made an unexpected decision: he became the rabbi he couldn’t find.

Now, he operates in two worlds—helping build global biotech communities focused on advancing patient care, while also guiding people through some of life’s most meaningful and vulnerable moments. At the center of both is the same idea: showing up for people in a real, human way.

The conversation touches on interfaith families, the evolving role of religion, leadership through humility, and why relationships—not transactions—are what actually move things forward. It’s thoughtful, funny, and grounded, with a few unexpected moments along the way… including one very memorable sandwich story.

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.