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.

• • •

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

• • •

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.

• • •

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!

If you think Shark Tank shows you how real investment deals work, it's time to look deeper.

After 35+ years of structuring actual deals, I have some thoughts.

Don't get me wrong. Shark Tank has done incredible things for entrepreneurship awareness. It's entertaining. It introduces people to concepts like customer acquisition costs and business valuations.

But as someone who negotiates real deals, the show misses so much of what actually happens.

Mark Cuban's "shot clock" negotiations? Not how real investors operate.

The focus on simple equity percentages? Real deals involve preferred shares, liquidation preferences, board seats, anti-dilution rights.

Those dramatic handshake commitments? Studies show 30-40% of Shark Tank "deals" never actually close.

And we rarely hear follow-up on companies that struggle or fail.

Compare this to The Pitch podcast, which features real investors evaluating real companies with full follow-up on what happens after the cameras stop rolling.

We'll dive deep into this (and so much more) in this episode of the DealQuest Podcast!

• What Shark Tank gets right about deal basics
• The crucial deal terms that never get discussed on TV
• Why most "Shark Tank deals" don't actually close
• How The Pitch provides authentic deal education
• And much more

So if you're an entrepreneur considering investment or anyone fascinated by how deals really work, you'll want to hit play on this one.

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

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!

If your definition of success still sounds like someone else’s dream… It’s time to rewrite it
⁠
I was deeply moved by this conversation with the incredible Rha Goddess. - CEO of Move The Crowd, the author of The Calling, and a cultural innovator who has helped hundreds of changemakers stay true to themselves while making bank.⁠

In this episode, she breaks down how to negotiate deals with soul, reclaim your worth in high-stakes rooms, and redefine success on your own terms.⁠

We talked about ambition, but not the hustle-till-you-drop kind.⁠
⁠
We talked about impact, but not the performative kind.⁠
⁠
And we talked about power, the kind that comes from knowing who you really are.⁠
⁠
I’ve never looked at ambition the same way since.⁠
⁠
What comes up for you in this conversation? I’d love to hear your thoughts in the comments below.
⁠
So if you’re building a business, legacy, or life that actually feels good...
⁠
You’ll want to hit play on this one.⁠

• • •

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

• • •

FOR MORE ON RHA GODDESS
https://www.movethecrowd.me/
https://www.linkedin.com/in/rhagoddess
https://www.facebook.com/RhaGoddess/
https://bit.ly/IntentionalAmbitionBook

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!

Feeling stuck inside someone else’s definition of success?

If you’re a financial advisor dreaming about building a business on your terms, this is for you.

Because here’s the thing…

The RIA model is one of the most powerful paths to real independence in the wealth management space.

And this DealQuest episode, we’re talking with Chuck Failla—founder of Sovereign Financial Group and a fierce advocate for advisor freedom.

He’s breaking down:
- Why so many advisors are finally making the leap
- What to know before going independent
- How to navigate the challenges that come with freedom (yes, they exist)
- And why values-based leadership is the future of wealth management

And much more

• • •

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

• • •

FOR MORE ON CHUCK FAILLA
https://www.linkedin.com/in/charlesfailla/
https://twitter.com/SF_Group_Inc
http://www.goria.com/

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!

Why REPORTERS might know more than the CEOs they cover…
⁠
Couldn’t agree more with the insights dropped by Diana Britton and Ian Wenik on this episode of DealQuest.⁠
⁠
In case you don’t already know Diana & Ian…⁠

• Ian is the Editor at Citywire RIA and host of This Week in Wealth⁠
• Diana is the Managing Editor at WealthManagement.com and host of The Healthy Advisor Podcast⁠

Together, they’ve interviewed just about everyone in the RIA space (yours truly included)⁠
⁠
They’ve spent years behind the mic asking the big questions...⁠
⁠
So this time, I flipped the script—⁠
⁠
And I asked them what’s really going on in wealth management.⁠
⁠
Here’s what we dug into:⁠
- The truth about RIA M&A and what’s happening behind the scenes
- The rising risks of private equity and over-leveraging⁠
- How politics and tax policy are shifting deal timing
- The massive talent and succession gaps too many firms are ignoring⁠

And much more ⁠

If you want the unfiltered take on where this industry is headed…⁠

• • •

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

• • •

FOR MORE ON DIANA BRITTON
WealthManagement.com

FOR MORE ON IAN WENIK
Citywire RIA

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!

For YEARS, business owners have been told to wait for the right time to make deals, especially when the economy feels uncertain.⁠
⁠
But… that strategy could be killing your momentum.
⁠
In this solocast episode of the DealQuest Podcast, I’ll break down…⁠
- Why fear-based decisions kill more deals than a downturn ever could
- How to shift your mindset from reactive to strategic
- What smart deal structures look like in a changing market
- How to stay confident (even when the headlines say panic)

And much more…
⁠
• • •

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

• • •

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!

If you’ve been hesitating to make a move or second-guessing your next step…⁠ You need to hear this.⁠