Unlock Baby Boomer Business Transitions with Georgi Feidler

In this episode of the DealQuest Podcast, I'm thrilled to welcome Georgi Feidler – a seasoned leader with 20+ years of experience spanning global multi-site and multi-state operations across Fortune 500, healthcare, CPG technology, SaaS, and startups. She's played a pivotal role in IPOs, mergers, acquisitions, capital raises, and scaling companies from small teams to organizations with over 68,000 employees with a strategic yet hands-on approach.

Georgi partners with founders, CEOs, COOs, and executive teams to align people, process and systems with the company's vision. She thrives in high growth environments, leveraging data driven decisions to fuel sustainable business success. What makes her work particularly fascinating is her specialization in helping Baby Boomers transition out of their companies with smooth succession plans that allow them to retire early while preserving their legacy and business continuity.

Whether you're a boomer founder planning your exit, a business owner thinking about succession, or someone interested in the massive wealth transfer happening over the next decade, this conversation provides actionable insights for creating businesses that can thrive beyond their founders.

FROM PEDIATRICIAN DREAMS TO DEAL REALITY

Georgi's journey to becoming a succession planning expert started with wanting to be a pediatrician at age 12. That dream ended abruptly when her nephew cracked his head open and there was blood everywhere and she started vomiting.

Sometimes our biggest career pivots come from the most unexpected moments. After ruling out medicine and then law (following a summer working in an attorney's office), Georgi took what she calls a "winding road" through recruiting, finance, sales, and marketing before finding her calling in operations and people strategy.

The lesson? Don't be afraid of a non-linear path, the diverse experience often becomes your greatest asset.

THE DEAL IS JUST THE BEGINNING

Georgi's first real deal experience came in senior living, where she worked as a major market manager during a period of explosive growth. Over just three years, the company grew from 4,800 to 68,000 employees through a series of mergers and acquisitions.

Her role was fascinating: turn competitors into collaborators. They helped senior living communities that used to compete against each other come together under a unified network. This involved launching new communities, redesigning go-to-market strategies, restructuring teams, and aligning referral and commission models to support shared success instead of competition.

But here's what stuck with her: "The deal is just the beginning. What really matters is what happens after the deal. How you integrate and operationalize it, that's what makes or breaks it."

SMALLER COMPANIES CAN ACQUIRE BIGGER ONES

One of the most interesting aspects of Georgi's M&A experience was seeing a smaller, more agile company acquire much larger competitors. This was during the mid-2000s recession when bigger senior living communities were over-invested and exposed, leading to Chapter 11 reorganizations.

The smaller company Georgi worked for had the right P&L, the right vision, and could pivot fast enough to make necessary changes. The larger companies couldn't turn fast enough to correct where the business was going given economic conditions.

This taught her that size isn't everything in acquisitions, agility and financial discipline often trump scale when market conditions shift.

WHY BABY BOOMERS NEED SUCCESSION HELP NOW

Over 50% of small businesses are owned by Baby Boomers right now. There are approximately 10 million boomers retiring every single day, and 60% of those have absolutely no succession plan. In the next decade, there are literally billions of dollars of wealth that have the opportunity to be transferred.

The problem? They know they want to transition, but they don't know how to do it. And by the time they reach the point where they're ready to leave, they're often so done that there's not enough fuel left in the tank to do what they need to do to help them transition without losing what they've built.

The window for effective succession planning is narrowing rapidly, making this one of the most critical business challenges of our time.

THE TRIBAL KNOWLEDGE PROBLEM

The first major roadblock Baby Boomers face when trying to make their businesses deal-ready is what Georgi calls "the tribal knowledge problem." The systems, processes, and customer relationships live in their heads.

What makes Baby Boomers unique compared to Gen X, Millennials, and Gen Z is that they spent their careers building mastery through tenure and loyalty. They stayed in positions long enough to develop incredible depth of knowledge that younger generations – who might only stay at a job for 18 months to five years – simply can't develop.

But the problem is this knowledge is undocumented, invisible, and critical. Buyers don't want key knowledge walking out post-close, and they don't want to buy a job – they want to buy a business.

The work to fix this isn't sexy: process documentation, transition plans, role shadowing, delegation timelines. But there's no way around it – they have to put on their big boy, big girl pants and do the work.

THEY'RE SO DONE BUT CAN'T TRUST ANYONE ELSE

The second roadblock is that Baby Boomers often hold on longer than they actually want to because they don't trust anyone else to run the business. And often, they're not wrong about that.

The solution is building confidence through clarity. They need to get clear first before they can help other people get clear. It's about testing and iterating – testing the transitions, testing what works and what doesn't.

Letting go isn't an all-at-once thing. It's a transformation requiring a phased exit approach.

NO ONE ELSE TO TAKE OVER

The third roadblock is simply that there's no one else to take over. Many boomer clients envisioned their kids would want the business, but the kids are off doing their own careers or being influencers – they don't want to run a pool business or a plumbing business.

This is where succession planning becomes critical. Successors aren't magically created or born – they're built over time. This involves developing internal talent, sourcing external operators, and putting in place advisory boards and fractional executives that can create stability within the business.

All of this takes years to develop properly.

INTERNAL SUCCESSION CREATIVE SOLUTIONS

Georgi shared a powerful case study of two second-generation business owners – a brother and sister who split their father's business into two locations after he ran it for 35 years. The brother had acquired additional companies and built infrastructure, while the sister had grown through "blood, sweat and tears" with her husband.

When Georgi started working with the brother about two years ago, he had infrastructure but was working 55 hours a week with no org structure and no leadership bench. About 14 months in, he said "I think this is the year" – his team didn't need him anymore, and he went from working 55 hours a week to being in the office but not really doing a lot.

Rather than having the sister spend years building up infrastructure, they created a shared services model. Anything that could be shared – ERP systems, HR, payroll, marketing, purchasing, account management for shared accounts, was combined between the two businesses. This allowed the sister to transition in about 10 months instead of requiring years of infrastructure development. They chose a Popeye plan, significantly changing the lives of employees who dedicated their lives to the company by making them owners over the course of 10 years.

WOMEN AND DEALS: A RELATIONSHIP ADVANTAGE

When discussing gender differences in deal-making, Georgi noted that while gender conditioning creates certain norms, women often have natural advantages in deals. Her psychology professor described men's brains as "a two-lane country road" while women's brains are "like a multi-ramp interstate hot freeway system."

This ability to see multiple dynamics and relationships simultaneously is actually a competitive advantage in deal-making. The best deals are relationships, and women are generally much more relational than men.

The challenge is breaking free from gender norms through choosing differently, mentorship, or experiences that expose them to the power of deals and how they can change things for people.

THE HIT BY THE BUS MENTALITY

Every business owner should ask themselves: "If I'm gone tomorrow, what happens? Does somebody else know the things that I know?" Even if knowledge is spread across the organization, somebody needs to know what the founder knows.

It's never too early to start thinking about this – even from the moment you start your business. Baby Boomers often relish being the backbone of their business, but this creates the ultimate succession challenge.

The freedom that comes from building a business that can run without you is transformative – not just for your exit strategy, but for your daily life and stress levels.

DEAL-READY CHECKLIST FOR ANY EXIT

Whether you're planning an external sale or internal succession, buyers and successors are looking for the same fundamentals: clean financials and unit economics, a team that can run without you, process automation and SOPs, transparent dashboards, a clear roadmap for what happens next, and proper governance structures.

The key question: Can your business run 90 days without you? If not, it's not deal-ready.

Tune in as Georgi Feidler reveals how Baby Boomer business owners can navigate the complex transition from founder-dependent businesses to sustainable enterprises. From tribal knowledge transfer to internal succession planning, this episode is a masterclass in creating businesses that can thrive beyond their founders.

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FOR MORE ON GEORGI FEIDLER

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FOR MORE ON COREY KUPFER

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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!