How to Navigate Deals in Economic Uncertainty & Keep Closing

In this solo episode of the DealQuest Podcast, I’m addressing a crucial topic that resurfaces every time economic uncertainty strikes: how shifting market conditions impact deals. Whether it’s the fallout from COVID, the global financial crisis, or today’s 2025 concerns over tariffs, rising interest rates, inflation, and stock market volatility, entrepreneurs and dealmakers alike often react with unnecessary fear and hesitation.

When uncertainty hits, many business owners and investors assume it’s time to pull back or pause deal activity. But are those assumptions accurate? And could stepping back actually mean missing out on valuable opportunities? The truth is, deals don’t just stop because the economy feels shaky, but the way we approach them should adjust.

In this episode, I’ll unpack the common misconceptions that surface during turbulent times and share strategies for staying level-headed, assessing risk wisely, and continuing to move forward when others retreat. Tune in to learn how to separate fact from fear and position yourself to make smarter deals, even when the headlines look grim.

UNCERTAINTY IS MORE PARALYZING THAN BAD NEWS

When the economy hits a rough patch, it’s not just bad news that disrupts entrepreneurs. It’s the uncertainty about what’s coming next. Not knowing whether tariffs will rise, interest rates will increase, or inflation will spike leaves you stuck, unsure whether to move forward, hold back, or pivot.

Here’s the reality: entrepreneurs prefer clear bad news over uncertainty. For example, if the Fed cuts interest rates, great. If they don’t, at least you know where you stand and can adjust. The worst? When the decision is dragged out, leaving everyone guessing.

That’s when businesses freeze. Deals get delayed, and entrepreneurs hesitate to act. Without clarity, it’s harder to make smart decisions, and inaction can be riskier than making the wrong move.

ADAPTABILITY IS KEY IN SHIFTING MARKETS

The one trait that sets successful entrepreneurs apart is adaptability. Economic conditions, policies, and market trends constantly change, and those who succeed are the ones who can quickly assess the situation and adjust their strategies.

Take this example: You were planning to raise capital through equity, but investor interest wanes or regulations shift. Instead of giving up, you pivot to debt financing. If that gets too expensive, you get creative and consider a friends-and-family round.

Understanding the market, even if it’s not ideal, lets you make smarter decisions and stay flexible. Being adaptable doesn’t mean settling; it means being smart enough to change course when needed. Entrepreneurs who can pivot quickly, rather than waiting for perfect conditions, are the ones who keep moving forward while others stall.

DON’T FREEZE! ADJUST YOUR DEALS TO KEEP MOVING FORWARD

Uncertainty is a part of business, whether it’s due to rising interest rates, inflation, or unexpected events. The biggest mistake is freezing up in fear and doing nothing. This can cause you to miss opportunities. Instead of freezing, take a step back, evaluate the situation, and adjust your deal structures to account for the uncertainty.

For example, if the market dips or clients pull back, you don’t have to walk away from deals, just adjust the terms. You could:

• Add earnouts, where part of the payment is based on future performance.
• Use contingent payments that depend on client retention or goals.
• Set retention requirements to ensure key clients or employees stay on board.
• Adjust valuations to reflect increased risk.

The goal is to create a deal that protects both parties, so if things go well, the seller benefits, but if things don’t, the buyer isn’t overpaying. Inaction is riskier than adapting. Flexible deal structures let you manage risk and keep moving forward when others freeze.

NOT ALL MARKETS REACT THE SAME, KNOW YOURS

When the economy takes a hit—whether from a recession, inflation, or policy shifts, it’s easy to get swept up in doom-and-gloom talk like “everything’s slowing down” or “nobody’s doing deals.” But the reality is, different industries respond in different ways. Some stall, others stay steady, and a few even thrive.

In some sectors, deal activity barely misses a beat. Valuations hold strong, capital keeps flowing, and growth continues, especially when fundamentals are solid and investor interest remains high. So don’t assume the worst just because headlines say so. Take a step back, look closely at how your market is actually reacting, and make moves based on facts, not fear. That’s how smart dealmakers spot the openings others miss.

TOUGH TIMES CAN BE GOLDMINES, IF YOU’RE READY TO MOVE

There’s truth to the saying, “Fortunes are made during recessions.” Some of the most successful businesses launched when others were too hesitant to take action. Certain investors stay active even when the economy cools. They’ve raised capital they’re committed to using—and that momentum doesn’t stop overnight. Some industries continue to attract investment because their fundamentals remain solid, regardless of broader uncertainty.

Don’t assume slowdowns mean it’s time to sit still. Look for sectors that are still moving, stay steady while others panic, and be ready to make smart moves when opportunity shows up. That’s often where the biggest wins happen.

MARKETS AND DEAL ACTIVITY ARE COMPLEX AND NUANCED

It’s easy to fall into the trap of thinking: “The market’s down because of X” or “Deals have dried up because of Y.” But in reality, markets and deal flows are complex systems with many moving parts — and rarely is there just one simple reason behind changes. The financial media loves clean narratives (e.g., “Markets dropped today because of tariffs”), but those stories often oversimplify a very tangled reality.

The same is true in M&A and private equity:

• Deals don’t stop or start because of one single factor
• Money moves in ways that aren’t always obvious
• There are many segments, sectors, players, and strategies all reacting differently

Avoid making blanket assumptions. Instead, dig into how your specific sector, business, and market conditions are affected. Look behind the headlines, analyze multiple factors, and make decisions based on a detailed, nuanced understanding — not just surface-level explanations.

PE MOVES ON A DIFFERENT TIMELINE

Private equity (PE) investment doesn’t move in lockstep with the general economy. Here’s what the data shows:

• When downturns hit, PE activity typically lags — it slows down later than the broader economy
• When recoveries happen, PE activity usually rebounds earlier than the general market

Why does this matter? Because if you’re looking to raise PE capital, exit to a larger PE firm, or plan your next move, understanding this timing lag can give you an edge. You might have more leeway now than you think if downturn impacts are delayed. You may want to accelerate fundraising or exits if a longer downturn is coming. Knowing that PE bounces back sooner could shape how you prepare for recovery

Strategic timing - based on real PE cycle patterns - is crucial. Use historical patterns and data to guide your business decisions. Don’t try to perfectly predict the market, but use these insights as tools to plan smarter.

DON’T LET EMOTIONS OR POLITICS CLOUD YOUR BUSINESS JUDGMENT

It’s easy to get swept up when economic policies become political battlegrounds. Whether you strongly support or oppose a new regulation, letting those feelings dictate your business strategy can lead to costly missteps. The truth is, your emotional reaction, no matter how justified, won’t change how a policy actually impacts your business on the ground.

Maybe you feel compelled to take a stand. That’s valid, especially if you’re the sole decision-maker and your values are central to your brand. But if you’re going to make a move that could impact profits, do it with intention, not out of impulse or frustration. Avoid knee-jerk reactions that are fueled by fear, anger, or political bias.

Instead, pause and evaluate: How does this change directly affect your operations, your clients, your cash flow? What are the actual implications, not just what’s being said in the headlines? Get clear on the facts, separate emotion from analysis, and then decide what action makes the most sense for your business.

LASTING ENTREPRENEURS STAY CALM AND KEEP MOVING

Tough times make everyone nervous - that’s human. But the business owners who go the distance aren’t the ones who freeze or wait for things to magically improve. They’re the ones who pause, take a breath, and keep making smart, steady moves, even if they have to slow down.

Some people thrive when the economy is strong and everything feels easy. But as soon as things shift, like a recession or policy change, they panic. Either they make no moves at all or they act out of fear and make costly mistakes. The entrepreneurs who last? They stay calm under pressure, adapt as needed, and keep making informed decisions. Their mindset is: “This will pass, and if I stay clear and flexible, I’ll come out stronger.”

Don’t freeze. Don’t flail. Stay grounded, stay strategic, and keep moving forward, even when the path gets bumpy.


Tune in to this episode to hear my insights on how to adapt your strategy, structure smarter deals, and stay confident in uncertain economic times, without letting fear or market noise derail your momentum.
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Corey Kupfer is an expert strategist, negotiator, and dealmaker. He has more than 35 years of professional deal-making and negotiating experience. Corey is a successful entrepreneur, attorney, consultant, author, and professional speaker. He is deeply passionate about deal-driven growth. He is also the creator and host of the DealQuest Podcast.

Get deal-ready with the DealQuest Podcast with Corey Kupfer, where like-minded entrepreneurs and business leaders converge, share insights and challenges, and success stories. Equip yourself with the tools, resources, and support necessary to navigate the complex yet rewarding world of dealmaking. Dive into the world of deal-driven growth today!