Founder Regret, Exit Clarity & What Money Can't Buy with Jodi Hume

When most people think about evaluating a deal, they focus on the numbers, the legal terms, and the financial projections. But what if the most critical work happens before you ever see a term sheet? Jodi Hume has spent years working with founders and CEOs through acquisitions, mergers, and strategic exits, and she's discovered something that rarely makes it into mainstream deal advice: people regret the deals they do far more often than they regret the money they leave on the table.

In this episode, Jodi shares how she went from a government shutdown forcing her into an architecture firm to becoming a trusted advisor guiding executives through some of the most consequential moments of their businesses. Her journey reveals how the most valuable skill in dealmaking isn't financial engineering or negotiation tactics—it's the ability to help leaders understand what they actually care about before they sign away their company.

The Accidental Path to Deal Expertise

Jodi's entry into the professional world was shaped by a single unexpected event. In October 1995, while working at the National Institute of Health doing psychological research, the government shut down. Because she was paid hourly on a grant, she couldn't afford to go without pay for even a week. She took a job answering phones at an architecture firm, expecting to stay six months before returning to graduate school. She stayed for 16 years.

What made those 16 years transformative wasn't just her technical growth. As the firm expanded from eight people to 10 million in revenue, Jodi found herself in leadership meetings that shaped her understanding of how organizations actually work. She sat in weekly two to three-hour sessions where every major decision was made, watching leaders navigate competing priorities, revisit decisions that didn't work, and course-correct in real time. "It was a better education that I could have ever gone to school for," she reflects.

Finding Your Highest and Best Use

Throughout her career, Jodi discovered something crucial about herself: she's exceptionally good at making things better, but once they're fixed and systematized, she loses interest. This self-awareness became the foundation for how she structures her work and advises others.

She introduced me to a concept I use constantly in my own practice, borrowed from architecture: "highest and best use." This principle guides everything from how leaders spend their time to what roles they should actually occupy. For Jodi, knowing that scheduling meetings drains her mental capacity while facilitating strategy energizes her meant delegating scheduling to someone else, even when she was barely profitable. "It doesn't matter," she says simply. The highest use of your time and attention is too valuable to waste on tasks that don't leverage your unique strengths.

I've applied this framework to help my clients think about their own businesses. I have my team track their time for a full week and then calculate what percentage actually falls into their highest and best use areas. The results are often sobering—most executives discover they're spending only a fraction of their time on work that actually moves the needle. Once you identify what drains your energy versus what builds you up, the next step is simple: systemize, delegate, outsource, or eliminate everything else.

The Real Work Before the Deal

Jodi's most important contribution to founders and CEOs isn't about M&A mechanics. It's about something almost nobody talks about: clarity around what actually matters to you in an exit.

She shared a story that illustrates this perfectly. A client called her months after they'd stopped working together. The deal on the table looked flawless on paper. His wife was confused about why he was hesitating. Every rational metric pointed to yes. Yet something was clearly wrong.

As they talked through it, Jodi asked a simple question: "What does your next year look like?" He described being in Arizona for six-week stretches to manage integration, returning home for a week, then heading back out again. Then Jodi reminded him of something he'd told her months earlier, before this deal appeared: his youngest son's senior year of high school was coming up, and he'd committed to being present for it.

The moment he recognized the conflict, everything clicked. He didn't kill the deal. Instead, he negotiated a different structure that allowed him to prioritize both the acquisition and his son's final year at home. The key wasn't the deal structure itself—it was naming what mattered before emotion and momentum took over.

Energy Management in the Midst of Chaos

Acquisitions and exits create their own unique pressure. Due diligence, information requests, constant surprises—it's exhausting. Meanwhile, your company still needs to run. Many founders make decisions they later regret simply because they're too depleted to think clearly, or they accept a deal they don't actually want just to end the process.

Jodi focuses on two critical elements most advisors overlook. First, she manages the founder's emotional and physical energy throughout the process. If you're raising capital as part of a larger exit, you might not be able to share details with your leadership team for weeks. That secrecy creates its own burden. She helps clients navigate that reality so they don't make decisions from a place of exhaustion or desperation.

Second, and more importantly, she helps founders articulate and protect what Jodi calls "regret management." What are you willing to compromise on, and what would you still regret months or years later if it changed? She often creates a matrix with clients: what matters to you, what are the nuances of those things, and in what order do they rank? Because the deal process creates its own momentum. Everything feels rushed. Suddenly everything seems like it hinges on making this particular deal go through. And that's often just not true.

When Founders Get Lost in the Forest

One of Jodi's most powerful observations comes from a poem she references: "If you're lost in the forest, the trees know where you are." Early in her deal experience, she noticed that when acquisitions were brewing, she could provide something other advisors couldn't. She was able to orient people to what was actually happening, rather than getting lost with them.

During due diligence, anxiety spikes. People interpret normal scrutiny as threats. They read motives into routine questions. I see this with my clients on the sell side—the due diligence team often comes in after the CEO has green-lit the deal, and their job is to find problems. They have more downside risk if something goes wrong than if the deal falls through. So they're inherently more skeptical. Understanding that dynamic matters.

Jodi adds another layer: she listens for what's driving people's actual concerns. Is it genuine risk, or is it anxiety born from uncertainty? When a CEO told her "the wheels are coming off the car" because someone reacted emotionally to a simple question, Jodi could reframe it: this is normal. People get worried because everything feels uncertain. That's predictable. That's manageable.

The Harder Conversation Nobody Wants to Have

There's a narrative in entrepreneurship that you should always be scaling, always be optimizing for a bigger exit, always be maximizing value. But Jodi raises something that almost never gets discussed: sometimes the right deal is the one that acknowledges reality.

She's worked with founders who are simply done. Not tired in a way that a vacation fixes, but fundamentally depleted. When advisors tell these leaders they could wait another year or two and get significantly more money, Jodi pushes back. If a founder doesn't have it in them anymore, the business will likely be worth less in two years, not more. Their absence will show. Their energy will dissipate through the organization.

The uncomfortable truth: sometimes a good deal is one where you're honest about what you have left to give. That's not failure. It's wisdom.

Building the Right Deal Team

Conventional wisdom says your deal team should include lawyers, accountants, and maybe a financial advisor. But I've consistently found that advisors who can help you get crystal clear on what matters are worth more than specialists who only optimize for price and terms.

Jodi describes her approach as understanding three intersecting dimensions of a person: what's going on in their business, what's happening in their life (family, health, outside commitments), and their own particular quirks and what drives them. You can't strategize effectively if you're only looking at one dimension. A perfect deal on paper can destroy someone's life if you didn't understand their personal reality.

When you're only examining the numbers and legal strategy, you're missing crucial variables. The best deal isn't always the biggest offer or the most favorable terms. It's the one that aligns with what you're actually trying to accomplish.

The Overlooked Trend: Rethinking Fundraising

As we wrapped our conversation, Jodi highlighted something she's seeing shift in the founder world: more and more entrepreneurs are questioning whether raising capital is actually necessary for their business. This isn't about going back to bootstrapping everything. It's about being more discerning.

She's had clients who've contemplated how they'd have grown differently if they'd invested the energy they poured into fundraising and managing board relationships into sales instead. Sometimes the trade-offs of venture capital aren't worth the growth it produces. That's a conversation that rarely happens because raising money is treated as a foregone conclusion, not a strategic choice.

The Systemic Depletion Nobody's Talking About

Beyond specific strategies, Jodi identified something more ambient affecting founders right now: a pervasive sense of depletion that goes beyond normal stress. It's not just about daily exhaustion. It's a depletion of reserves.

She compared it to living paycheck to paycheck. When you're just meeting your month-to-month obligations, one unexpected expense can send you into crisis. For founders, something similar is happening emotionally and mentally. The pandemic and the divisiveness that followed created a kind of ongoing uncertainty that's made everything feel harder than it was five or ten years ago. It's not that there's one solution, but recognizing it matters. Because when you understand that the challenge isn't just your company or your deal but something in the broader environment, it changes how you approach your own wellbeing.

Connecting Personal Ambition to Deal Strategy

One insight that stayed with me: there's a difference between ambition that comes from you and ambition that's been handed to you by external expectations. Jodi talks about listening for when someone's describing something that clearly energizes them versus when they're describing what they think they're supposed to want.

My wife recently published a book called Intentional Ambition that dives into this exact space. She distinguishes between healthy drivers of ambition and what she calls wounded drivers. The work Jodi does with founders is essentially helping them identify which is which before they commit to a deal. Because the wrong ambition—the kind driven by other people's expectations or reactive desperation—will make you regret almost any deal, no matter how good it looks on paper.

Jodi's Perspective on Freedom

When I asked Jodi about her highest value, she pointed to options. Not freedom in the abstract sense, but the concrete ability to choose. She acknowledges that fewer options make her panicky, which is why she's thoughtful about what she commits to, even as far out as booking her band for 2026. That need to preserve optionality shapes everything she does.

Related Episodes

If you're exploring deal strategy, the perspective Richard Manders shares on navigating the transition after a major exit directly complements what Jodi raises here about identity and what comes next. He faced similar questions about who he was after his company sold, and what he discovered fundamentally shaped how he now works with other founders.

For a deeper look at the post-exit landscape and what founders actually experience after a sale, Tom Dillon has addressed this terrain as well—particularly around what founders don't expect when they reach the finish line.

And if you're thinking about whether you even need to build toward an exit in the first place, there are conversations about lifestyle business and why scaling isn't mandatory that challenge the default narrative Jodi references here.

Listen to the full episode of DealQuest Podcast Episode 366 with Jodi Hume: Available on all major podcast platforms

FOR MORE ON JODI HUME:
https://www.linkedin.com/in/joditurnerhume/
https://atthecore.com/

FOR MORE ON COREY KUPFER
https://www.linkedin.com/in/coreykupfer/
https://www.coreykupfer.com/

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!