Holding Company Blog

Here at the holding company blog, we discuss all insights and opportunities for your entrepreneur journey

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How We Think About Legacy

AI’s Role in Scaling Portfolio Company Growth & Efficiency

In Praise of Unsexy Businesses

Why Profitability Matters More Than Hype

Legacy Planning: Pairing CRTs With Life Insurance to Benefit Your Heirs

Holding Companies Are the Future of Entrepreneurship

The Power of Boring Businesses in a Holding Portfolio

Can a Holding Company Be Remote-First?

Independent Sponsors vs. Search Funders: Capital, Control & Culture Differences

Should a Holding Company Have a Central HQ?

Hiring for a Company That Doesn’t “Operate”

What Culture Looks Like Across Multiple Subsidiaries

Moving from Operator to Allocator: A Mental Shift

How Holding Companies Can Foster Startup Culture

Strip the Assets, Keep the Brand: PE’s Favorite Magic Trick

Holding Period Arbitrage: The Exit Trick You Forgot

Cap Rate Compression and Other Bad Vibes

Why We Chose to Be a Holding Company

The Identity Puzzle: Does a Holding Company Need a Personality?

Thinking in Decades: The Holding Company Mindset

Lessons From the Most Successful Holding Companies in History

Independent Sponsors vs. Search Funders: What’s the Difference?

How Holding Companies Can Revive Struggling Businesses

How Blockchain Technology Could Impact Holding Companies

Digital Transformation Strategies for Holding Companies

Building a Portfolio Without Building a Brand

Zero-Cash-Flow Properties: Yes, That’s a Thing

Tax Credit Syndication: Bureaucracy With a Bonus

Institutional Buyers Are Coming—Time to Sell or Scale?

Real Estate Sale Leasebacks: Monetize Your Building Without Moving

Real Estate Investing KPIs That Actually Matter (Spoiler: Not Occupancy Rate)

Pros & Cons of Vertical Integration

How Holding Companies Use Shared Services to Reduce Costs

Cash Flow Management for Holding Companies

The Pros and Cons of Historic Tax Credits

Green Leases: ESG Commitment or Just Another Line Item?

Co-Investment Illusions: More Risk, Same Drama

“Passive” Doesn’t Mean “Risk‑Free” in Triple Net Leases

Pros and Cons of Zoning Arbitrage in Real Estate Investing

Pros and Cons of Anchor Tenants in Real Estate Investing

How Holding Companies Manage Multiple Subsidiaries Effectively

Common Legal Mistakes Holding Companies Should Avoid

Building a Strong Leadership Team in a Holding Company

Shadow CapEx: The Ugly Line Item in Every Model

Rent Rolls and Red Flags in Real Estate Investing

Real Estate Debt Funds: Quietly Eating Your Equity

PropTech Promises vs. Real-World Payoffs

Land Banking: When Holding Dirt Is the Smartest Move

Ground Leases: The “Nuclear Option” for Structuring Reliable Cash Flow

CRE Tokenization: Hype, Hoopla, or the Future?

Why Most Founders Should Fear (Not Chase) Venture Capital

SAFE Notes: The VC Equivalent of a Participation Trophy

Exit Strategies in VC: IPO, Acquisition, or Just a Slow, Quiet Death?

How To Set Up a Holding Company for Maximum Tax Efficiency

LLC vs. Corporation: Choosing the Right Setup for Your Holding Company

Why Your Startup’s Valuation Is a Lie (And Why That’s a Good Thing)

The VC Portfolio Math No One Talks About: It’s All About That One Unicorn

Burn Rate vs. Runway: When "Move Fast" Turns Into "Crash Hard"

Tax Benefits of Running a Holding Company

How Holding Companies Can Leverage Debt for Growth

Mergers and Acquisitions: Best Practices for Holding Companies

Private Equity vs. Holding Companies: Which Is Better for Your Business Growth?

How To Evaluate Businesses for Acquisition as a Holding Company

Industries That Perform Well Under a Holding Company Model

What is the Difference Between a Holding Company and an Operating Company?

How Holding Companies Acquire and Scale Businesses

The Truth About Private Equity Fund Structures

The “Dry Powder” Illusion: Why Too Much Capital Is a Bad Thing

Secrets of Beating Vanguard Index Funds: What Wealthy Investors Know

LBOs: Leveraged to the Hilt or Just Smart Capital Allocation?

How PE Firms Engineer Returns (Hint: It’s Not Magic, It’s Debt)

Distressed Asset Investing: Buying Chaos at a Discount

Why EBITDA Lies: A Deep Dive Into PE’s Favorite Fairy Tale

Roll-Ups: The PE Strategy That Works Until It Doesn’t

Debt vs. Equity in Real Estate: The Difference Between Getting Paid and Getting Played

The Role of a Holding Company in Business Expansion

What Is a Holding Company and How Does It Work?

Should You Exit Your Business by Selling or Hiring a CEO?

The Benefits of Structuring Your Business as a Holding Company

How Holding Companies Minimize Risk and Maximize Profits

Asset Protection Strategies for Holding Companies

Why "Hassle-Free" Is Often a Lie in Turnkey Real Estate

The Capital Stack in Real Estate Deals: Where You Sit Determines How Much You Eat

Real Estate Syndication vs. Direct Ownership: Do You Really Want That GP Carry?

Introducing the Multipreneur Operating System: The Ultimate in Holdco Management

The Myth of “Passive” Real Estate Investing Income

Cap Rate vs. IRR: Because Basic Metrics Are for Beginners

1031 Exchanges: How the IRS Lets You Legally Kick the Tax Can Down the Road

How to Fund Independent Sponsor Deals with Private Equity and Family Offices

How Holding Companies Acquire and Scale Subsidiaries

The Pros and Cons of Incubating, Investing in, and Acquiring Companies

The End of Venture Capital as We Know It: How AI and SPVs Are Eating the VC Model for Breakfast

How We're Scaling Our Holding Company with AI Agents

Holding Company Structural Subordination

Holding Company Capital Allocation

What Is Stale Real Estate and Why Is It Problematic?

Real Estate Investor Insurance: Everything You Need to Know

The Democratization of General Partners

How to Invest in Private Equity with Your IRA

Why Should Business Owners Invest in Whole Life Insurance?

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