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

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.

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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