Most entrepreneurs think raising VC money means they've "made it."

But Tom Dillon learned something different during his years in investment banking and running a PE-backed company.
After analyzing countless deals and experiencing the pressure firsthand, he discovered that VC money comes with a specific expectation: IPO-level returns.

"For a lot of VCs, they kinda look at things in terms of roulette table. They really need one of those to hit big."
The problem? Most successful businesses exit through M&A, not IPOs.

So if you're building a profitable company that could sell for $20-50M in a few years, VC funding might actually work against you.

Tom now helps founders as a fractional CFO, matching funding strategies to realistic business goals rather than chasing the biggest check.

In this episode, we explore:
• Why thinking multiple rounds ahead is crucial for any capital raise
• Alternative funding sources that align with M&A exits
• The growing trend of buying your first business instead of starting one
• How to set realistic valuation expectations
• The mindset shifts that separate successful founders from those who struggle

Perfect for entrepreneurs evaluating funding options and business owners planning exit strategies.

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FOR MORE ON THIS EPISODE:
https://www.coreykupfer.com/blog/tomdillon

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FOR MORE ON TOM DILLON
https://www.linkedin.com/in/tomdilloncfa/
https://fracfinance.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!

Georgi Feidler shared some incredible stats with me... Over 50% of small businesses are owned by Baby Boomers. 60% of those have zero succession plan.

That's billions in wealth transfer happening right now and most of it is going to be messy.

Georgi has spent 20+ years helping founders navigate this transition. Her approach isn't just about finding buyers - it's about building businesses that can actually survive without their founders.

The brother/sister case study she shared shows how creative structuring can cut transition time from years to months.
Perfect for business owners planning exits or anyone working with Boomer-owned businesses.

Georgi is the founder of Hire, Train, Aspire and a seasoned leader with 20+ years of experience who's helped scale companies from small teams to organizations with over 68,000 employees through IPOs, mergers, acquisitions, and capital raises.

In this episode, she breaks down how to overcome the "tribal knowledge problem," build confidence in your team to run without you, and create succession plans that work for both internal and external transitions.

We talked about business exits, succession planning, and freedom, the kind that comes from building something bigger than yourself.

So if you're a business owner thinking about your exit strategy or a Baby Boomer founder wondering how to preserve your legacy, you'll want to hit play on this one.

• • •

FOR MORE ON THIS EPISODE:
https://www.coreykupfer.com/blog/georgifeidler

• • •

FOR MORE ON GEORGI FEIDLER
Georgi Feidler's LinkedIn
Hire, Train, Aspire

FOR MORE ON COREY KUPFER
Corey Kupfer's LinkedIn
Corey Kupfer's Website

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!

Attention entrepreneurs: If you think working 80+ hour weeks makes your business more valuable...
the data says otherwise.

This conversation will change how you think about business building forever.

James Brown didn't just sell his business for multiple cash offers he proved that less owner involvement equals higher business value.

James is the founder of BizTech Guru, a business consultant who transformed his own accommodation business over many years from requiring 120-hour work weeks to just 30 minutes of monthly involvement. After surviving multiple economic challenges including the Global Financial Crisis and COVID-19, he eventually sold the business with 7 offers, 3 of which were cash.

In this episode, he exposes the shocking truth about why 80% of businesses aren't sellable, reveals his exact automation playbook, and shares the mindset shifts that create truly passive income.

We talked about business automation, but not the tech-heavy complicated kind.

We talked about remote team management, but not the micromanagement nightmare kind.

And we talked about exit preparation, the kind that actually increases your quality of life WHILE building value.
This completely changed my perspective on what makes businesses valuable.

Perfect for: SaaS founders, service business owners, e-commerce entrepreneurs, and anyone building for eventual exit.

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FOR MORE ON THIS EPISODE:
https://www.coreykupfer.com/blog/jamesbrown

• • •

FOR MORE ON JAMES BROWN
James Brown's LinkedIn
BizTech Guru Website

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