Why This Is One of the Best Times in 20 Years to Build, Buy, or Scale a Company

By Kyle Henderson | Henderson & Co.

Every economic cycle creates winners and losers, but this moment in time is unusually special. We’re sitting at the intersection of technological acceleration, shifting capital markets, and a generational transition in business ownership — and the result is one of the strongest environments in decades for operators, investors, and entrepreneurs who know how to execute.

Below is my take on where the real opportunities are right now.

1. A Massive Transfer of Business Ownership Has Officially Begun

More than 2.7 million U.S. businesses are owned by aging founders who will sell, transition, or shut down within the next 10 years.
Not tech startups. Not speculative ideas.
Real businesses. Real revenue. Real cash flow.

This wave is creating a historic pipeline of:

• Profitable, stable companies

• Undercapitalized but high-potential operations

• Businesses lacking modern systems or leadership

• Owners eager for clean exits or partial liquidity

For smart operators, this is the opportunity of a generation.

2. Technology is Multiplying Operational Capacity Like Never Before

AI, automation, workflow platforms, and low-code tools are rewriting what a small or mid-size business can do with the same workforce.

This shift isn’t hype — it’s measurable:

• Faster sales cycles

• Smaller administrative teams

• Cheaper acquisition channels

• Better data, forecasting, and operating visibility

• Higher margins without adding headcount

It’s now possible to buy a company doing $3M EBITDA and modernize it into a $6M EBITDA business within 36 months — without reckless spending or over-engineering.

Operators who understand both business fundamentals and modern tooling have a structural advantage.

3. The Best Deals Are Happening Off-Market, Not in Auction Rooms

Everyone sees the big PE auctions.
Almost nobody sees the quiet deals happening between:

• Founder-led businesses

• Family offices

• Strategic buyers

• Operator-investors

• Industry insiders

These deals often close at extremely attractive multiples because they’re built on relationships, capability, and speed — not bidding wars.

At Henderson & Co., we’re seeing high-quality companies trading hands at values that would’ve been unthinkable five years ago.

4. Capital Is Selective — Which Makes It More Valuable

Yes, interest rates are higher.
Yes, underwriting is tighter.
But that’s not a negative for skilled operators — it’s a filter.

When capital becomes selective, the market cleans up:

• Weakly run businesses fall off

• Flawed strategies get exposed

• Undisciplined competition shrinks

For strong operators, this environment provides more space to build, acquire, and improve without competing against short-term speculators.

And when execution is strong, capital is available — often on better terms than expected.

5. Operational Excellence Is the New Alpha

For years, returns were driven by financial engineering and cheap leverage.
That era ended in 2022.

Today’s real alpha comes from:

• Better systems

• Better people

• Better data

• Better execution

In other words:
operators, not financiers, are creating the returns.

This reality heavily favors firms that bring more than money to the table — firms that understand how to build infrastructure, professionalize teams, install discipline, and transform “good businesses” into “great ones.”

6. The Companies Winning Today Have Three Things in Common

Across industries, the winners in this cycle share the same characteristics:

1. Clarity
   Clear strategy, clear metrics, clear culture.

2. Control
   Control of cash flow, customer acquisition, and operational levers.

3. Competence
   Execution at every level — not just ideas.

These fundamentals matter more than ever. Flashy stories don’t move markets anymore. Strong operators do.

Final Perspective

In a world full of noise, uncertainty, and rapid change, it’s easy to miss the bigger truth:

This is an extraordinary environment for entrepreneurs and operator-investors.

Opportunity is everywhere, especially for those willing to buy well, build well, and operate with discipline.

At Henderson & Co., our focus is simple:
identify exceptional companies, strengthen their foundations, and help them grow with intelligence, clarity, and long-term alignment.

The cycle favors operators.
The environment favors action.
And the next decade belongs to those who can execute.

The State of Investing and Growing Companies in Today’s Economy

By Kyle Henderson | Henderson & Co.

The economy is in one of the most interesting phases we’ve seen in decades — a blend of strong fundamentals, persistent volatility, and structural change that’s reshaping how capital is raised, deployed, and scaled.

1. The Shift from Cheap Capital to Smart Capital

For more than a decade, growth was fueled by low interest rates and easy money. Today, the cost of capital has reset — forcing founders and investors alike to think differently. The best opportunities no longer go to those who raise the most, but to those who deploy the smartest.

At Henderson & Co., we’re seeing disciplined capital allocation win out over momentum. Investors are favoring profitability, recurring revenue, and capital efficiency over pure growth stories.

2. Valuations Are Normalizing — and That’s Healthy

Private company valuations are recalibrating after years of inflated multiples. While this correction has been painful for some, it’s creating one of the best buying environments in years.

For those willing to step in with operational expertise and patient capital, value creation opportunities are everywhere — especially in founder-led companies with real revenue and untapped potential.

3. M&A Activity Is Quietly Accelerating

Behind the headlines of market uncertainty, strategic buyers and family offices are moving quickly. Many are acquiring profitable, steady-growth businesses at 5–7x EBITDA multiples that would have commanded 10–12x just a few years ago.

For entrepreneurs looking to exit or recapitalize, this is an ideal time to engage experienced partners who understand both sides of the table.

4. The Next Decade Belongs to Operators

The next wave of winners won’t be defined by those who can raise the most capital — but by those who can build, optimize, and sustain. Investors are placing higher value on operating partners who bring infrastructure, systems, and execution discipline.

That’s where firms like Henderson & Co. are thriving — pairing capital with operational guidance to help companies grow responsibly and scale profitably.

5. A Renewed Focus on Trust and Alignment

Markets have a way of humbling everyone. The current cycle is reminding both founders and investors that alignment matters — not just in equity structure, but in vision, ethics, and long-term stewardship.

In a world moving faster than ever, trust is the ultimate differentiator.

Final Thoughts

We’re entering a decade that rewards clarity, conviction, and competence. It’s a time for strategic partnerships, thoughtful capital, and disciplined execution.

At Henderson & Co., we remain focused on one thing — helping exceptional companies grow through intelligent investment and operational excellence.