Holding Company Blog

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

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Growth at All Costs? No Thanks

Ryan Schwab

Burnout Is a Sign of a Bad Business Model

Ryan Schwab

Business Planning: Ultimate Guide to Writing a Business Plan for Investors

nate-nead

Why We’re Skeptical of “Founder-Friendly” Deals

Ryan Schwab

Our Favorite Questions to Ask Founders

Ryan Schwab

What We Look for in SMB Acquisitions

Ryan Schwab

The First 100 Days After an Acquisition

Nate Nead

How We Think About Legacy

Nate Nead

AI’s Role in Scaling Portfolio Company Growth & Efficiency

Nate Nead

In Praise of Unsexy Businesses

Ryan Schwab

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

ryan-schwab

Tax Credit Syndication: Bureaucracy With a Bonus

nate-nead

Institutional Buyers Are Coming—Time to Sell or Scale?

nate-nead

Real Estate Sale Leasebacks: Monetize Your Building Without Moving

nate-nead

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

ryan-schwab

Pros & Cons of Vertical Integration

nate-nead

How Holding Companies Use Shared Services to Reduce Costs

Cash Flow Management for Holding Companies

The Pros and Cons of Historic Tax Credits

nate-nead

Green Leases: ESG Commitment or Just Another Line Item?

nate-nead

Co-Investment Illusions: More Risk, Same Drama

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

ryan-schwab

Pros and Cons of Zoning Arbitrage in Real Estate Investing

ryan-schwab

Pros and Cons of Anchor Tenants in Real Estate Investing

nate-nead

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

nate-nead

Rent Rolls and Red Flags in Real Estate Investing

ryan-schwab

Real Estate Debt Funds: Quietly Eating Your Equity

nate-nead

PropTech Promises vs. Real-World Payoffs

nate-nead

Land Banking: When Holding Dirt Is the Smartest Move

nate-nead

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

nate-nead

SAFE Notes: The VC Equivalent of a Participation Trophy

nate-nead

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)

nate-nead

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

nate-nead

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

nate-nead

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

nate-nead

Secrets of Beating Vanguard Index Funds: What Wealthy Investors Know

nate-nead

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

ryan-schwab

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

nate-nead

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

nate-nead

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

nate-nead

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

nate-nead

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

nate-nead

Introducing the Multipreneur Operating System: The Ultimate in Holdco Management

The Myth of “Passive” Real Estate Investing Income

nate-nead

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

nate-nead

How We're Scaling Our Holding Company with AI Agents

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