The Coastal Collective Podcast
Stagione 1
Building Coastal: Sean Casper on Leadership, Private Investing & Long-Term Growth
di Coastal Investment Company
What does it take to transform a small investment operation into a growing private investment firm while maintaining the relationships and culture that helped build it? In Episode 2 of The Coastal Collective, host Carey Sobel welcomes longtime friend and Coastal Managing Partner Sean Casper for a conversation about entrepreneurship, organizational growth, investor relationships, and the evolution of Coastal Investment Co. Sean reflects on his professional journey, beginning in residential real estate and eventually moving into a regional leadership position at Compass. He discusses his early investments with Coastal, his decision to join the company in 2022, and the opportunity to help build something alongside people he had known for decades. The conversation provides an inside look at Coastal's expanding business, from real estate development and venture investments to tax strategies, mergers and acquisitions, and the creation of a dedicated investor relations department. Carey and Sean also explore how Coastal evaluates investment opportunities, why communication matters during multiyear investment projects, and how patience and discipline influence the firm's approach to changing market conditions. Beyond investing, the episode examines the personal side of building a company: recognizing talent, encouraging innovation, mentoring others, and developing a legacy that extends beyond financial success. 🎙Featured Guest: Sean Casper, Managing Partner, Coastal Investment Co. 🎙Host: Carey Sobel, Chief Acquisition Officer, Coastal Investment Co. 👉🏻Learn More: https://investwithcoastal.com 00:00 Cold Open: Building a Value-Driven Team 00:20 Welcome to The Coastal Collective 00:34 Introducing Sean Casper, Coastal Managing Partner 03:33 How Sean Got Started in Real Estate 04:51 Scaling a Business and Leading at Compass 05:32 Sean's First Investments with Coastal 06:34 The Opportunity to Help Build Coastal 07:27 The Phone Call That Changed Everything 09:48 How Sean's Previous Leadership Experience Translated to Coastal 11:16 Building Something of Your Own 12:33 Making Private Investment Opportunities More Accessible 14:53 Coastal's Early Days and Evolution 15:43 Turning Greg's Vision Into Execution 16:32 Building Coastal's Company Culture 18:29 Innovation, Accountability and Moving Fast 20:42 Building Coastal's Brand, Mission and Vision 21:04 What Is Coastal Investment Co.? 21:27 Coastal's Investment Divisions and Alternative Assets 23:14 Defining Success and the Coastal Investor 26:19 Sean's Role in Investor Relations, Marketing and Operations 27:34 The Work Behind Launching an Investment Opportunity 30:17 Scaling the Investor Relations Department 32:40 Coastal's South Florida Expansion 33:58 What Makes a Great Investor Experience? 35:32 Diversification and Long-Term Investor Communication 36:48 Capital Patience vs. Capital Urgency 38:04 Navigating Interest Rates and Real Estate Market Cycles 40:11 Ground-Up Development vs. Value-Add Investing 42:06 Building Investment Platforms Like Links Car Wash 42:49 How Coastal Selects Investment Opportunities 45:19 Risk Mitigation and Investment Due Diligence 48:15 Sean's Five-Year Vision for Coastal 50:18 The Future of Private Markets and Alternative Investments 51:45 The Most Rewarding Part of Sean's Journey 53:10 Leadership, Mentorship and Building a Legacy 54:46 How Lifelong Friendship Shapes Their Partnership 59:14 One Word That Describes Coastal 59:31 Final Reflections on Friendship and Building Coastal 01:00:05 Closing Remarks and Outro
What does it really take to build wealth beyond simply making money? In the inaugural episode of The Coastal Collective Podcast, host Carey Sobel, Chief M&A Officer, sits down with Greg Meerbaum, Co-Founder and CEO of Coastal, to unpack the story behind Coastal, his unconventional path from college dropout and entrepreneur to investor and company builder, and the philosophy that ultimately shaped the firm. Greg shares how his early business experience taught him that there are three distinct stages of money: making it, managing it, and learning how to duplicate it. From there, the conversation explores why relationships matter as much as individual deals, how access changes as investment scale grows, and why Coastal was built around connecting investors with experienced operators and individual private-market opportunities. Carey and Greg also dig into Coastal’s approach to evaluating sponsors, the importance of skin in the game, why getting closer to the actual operator matters, and the difference between capital urgency and patient capital. Along the way, Greg explains why he believes successful investing requires realistic expectations, disciplined due diligence, aligned incentives, and the willingness to think beyond the next quarter—or even the next few years. The episode closes with a more personal look at leadership, culture, legacy, and what Greg considers one of Coastal’s greatest accomplishments: creating an environment where the people around the company can grow personally, professionally, and financially. In this episode: • The three stages of money: make it, manage it, duplicate it • How Greg Meerbaum’s entrepreneurial career led to the creation of Coastal • Why relationships can be more valuable than a single transaction • How larger investment scale can create greater access and opportunity • What Coastal looks for in operators and investment partners • Why skin in the game and incentive alignment matter • Deal-by-deal investing versus blind-pool structures • Capital patience versus capital urgency • Why due diligence is central to Coastal’s investment philosophy • Building company culture while continuing to grow • Greg’s perspective on leadership, legacy, and building something that lasts This is the story behind Coastal—and the people, principles, and investment philosophy that helped build it. ______________ 00:00 — Welcome to The Coastal Collective 01:22 — Greg’s Story Before Coastal 06:49 — The Three Stages of Money 09:54 — Why Business Is About More Than the Deal 11:32 — Discovering Institutional Real Estate 14:05 — Building the Investment Platform He Wanted for Himself 17:19 — Skin in the Game and Betting on Operators 21:03 — Investor Education, Alternatives, and Access 24:19 — The Early Days of Coastal 26:30 — The First Deal That Proved the Concept 30:09 — What Investors Don’t See: The Due Diligence Machine 31:13 — Deal-by-Deal Investing vs. Blind-Pool Funds 35:44 — The Kentucky Derby Approach to Picking Investments 37:29 — Why Vertically Integrated Operators Matter 40:05 — Capital Patience vs. Capital Urgency 42:08 — The Danger of Chasing Unrealistic Returns 43:35 — Getting Closer to the Source 45:20 — Greg’s View of the Current Investment Environment 46:50 — The Biggest Mistake Greg Sees Investors Make 48:29 — Alignment: Why Coastal Gets Paid on the Back End 49:15 — What Does Coastal Look Like Five Years From Now? 50:36 — The One Thing Greg Never Wants Coastal to Lose 53:03 — Greg’s Proudest Accomplishment 54:32 — Legacy, Family, and Building Something That Lasts 56:33 — Lightning Round 57:28 — The “Problems in a Bucket” Philosophy