Feel the Fear & Do It Anyway - Kaylin Roche on theSkimm, JIGGY Puzzles, Shark Tank and Building a Life Worth Investing In

The Squeeze: Building Businesses, Raising Families & Why Average Doesn’t Win

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.

Craftsmanship, Entrepreneurship & Building Something That Lasts with David Stine & Stephanie Abbajay

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.

The Paycheck Derby: How to Win Big

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.

Birkin > S&P 500? The Luxury Resale Game Explained

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.

Feel the Fear & Do It Anyway - Kaylin Roche on theSkimm, JIGGY Puzzles, Shark Tank and Building a Life Worth Investing In

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.