Want a quick estimate of how much your business is worth?
With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business.
You might be surprised by how much you can get for it: https://flippa.com/exit
--
Are you building a business to own a job, or are you building an asset to sell? In this episode, Steve McGarry sits down with Chris Hallberg, Founder of Business Sergeant and an expert EOS Implementer, to dismantle the complexities of exiting a business.
Chris shares his personal journey from law enforcement to entrepreneurship, revealing the expensive mistakes he made during his first "fast and furious" exit. We dive deep into tactical preparation for a sale, including how to remove the "owner dependency" trap, the importance of business operating systems in driving up multiples, and how to navigate the ruthless "Fish and Chip" negotiation tactics used by buyers.
Whether you are looking to sell in 12 months or 10 years, this episode provides the blueprint for building a company that attracts top-tier buyers and maximum valuation.
In this episode, we cover:
--
Chris Hallberg is a high-energy entrepreneurial coach, facilitator, and Founder of GoExpand, an officially licensed EOS execution platform, dedicated to helping leadership teams build clarity, accountability, and healthy growth. As a seasoned Certified EOS Implementer®, Chris brings over a decade of full-time EOS experience working with companies across industries to align vision with execution and drive transformative results. Known for his direct yet kind communication style and practical mindset, he has helped more than 100 leadership teams foster world-class cultures and achieve measurable success. Chris blends disciplined operating system implementation with a people-first approach that empowers leaders to get what they want from their business and have fun doing it.
Websites - https://bizsgt.com/
- https://goexpand.com/
LinkedIn - https://www.linkedin.com/in/chris-hallberg-01516315/
--
Timestamps:
(00:24) – From Uniform to Suit: Chris’s transition from Military Police and Sheriff Deputy to high-growth entrepreneur.
(01:42) – The "Expedient" Exit Mistake: Why selling too fast cost Chris a fortune (and how to avoid it).
(03:31) – Golden Handcuffs: How to structure your leadership team so the business survives without you.
(07:14) – The "Fish and Chip" Model: Understanding the brutal reality of due diligence and last-minute price chiseling.
(10:23) – Timing the Market: Assessing trends (like AI) to know when your industry valuation has peaked.
(14:19) – Leadership Red Flags: Why "warm and fuzzy" leadership fails during the cold scrutiny of investment bankers.
(20:49) – Driving Valuation with EOS: How installing a Business Operating System can double or triple your multiple.
25:28 – The Transparency Dilemma: How to tell your team you are selling without causing a panic (The "Growth Capital" script).
(29:08) – The Halo Effect: Why hiring veterans and Special Ops leaders can transform your civilian workforce.
--
The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/
All content for The Exit - Presented By Flippa is the property of The Exit - Presented By Flippa and is served directly from their servers
with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Want a quick estimate of how much your business is worth?
With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business.
You might be surprised by how much you can get for it: https://flippa.com/exit
--
Are you building a business to own a job, or are you building an asset to sell? In this episode, Steve McGarry sits down with Chris Hallberg, Founder of Business Sergeant and an expert EOS Implementer, to dismantle the complexities of exiting a business.
Chris shares his personal journey from law enforcement to entrepreneurship, revealing the expensive mistakes he made during his first "fast and furious" exit. We dive deep into tactical preparation for a sale, including how to remove the "owner dependency" trap, the importance of business operating systems in driving up multiples, and how to navigate the ruthless "Fish and Chip" negotiation tactics used by buyers.
Whether you are looking to sell in 12 months or 10 years, this episode provides the blueprint for building a company that attracts top-tier buyers and maximum valuation.
In this episode, we cover:
--
Chris Hallberg is a high-energy entrepreneurial coach, facilitator, and Founder of GoExpand, an officially licensed EOS execution platform, dedicated to helping leadership teams build clarity, accountability, and healthy growth. As a seasoned Certified EOS Implementer®, Chris brings over a decade of full-time EOS experience working with companies across industries to align vision with execution and drive transformative results. Known for his direct yet kind communication style and practical mindset, he has helped more than 100 leadership teams foster world-class cultures and achieve measurable success. Chris blends disciplined operating system implementation with a people-first approach that empowers leaders to get what they want from their business and have fun doing it.
Websites - https://bizsgt.com/
- https://goexpand.com/
LinkedIn - https://www.linkedin.com/in/chris-hallberg-01516315/
--
Timestamps:
(00:24) – From Uniform to Suit: Chris’s transition from Military Police and Sheriff Deputy to high-growth entrepreneur.
(01:42) – The "Expedient" Exit Mistake: Why selling too fast cost Chris a fortune (and how to avoid it).
(03:31) – Golden Handcuffs: How to structure your leadership team so the business survives without you.
(07:14) – The "Fish and Chip" Model: Understanding the brutal reality of due diligence and last-minute price chiseling.
(10:23) – Timing the Market: Assessing trends (like AI) to know when your industry valuation has peaked.
(14:19) – Leadership Red Flags: Why "warm and fuzzy" leadership fails during the cold scrutiny of investment bankers.
(20:49) – Driving Valuation with EOS: How installing a Business Operating System can double or triple your multiple.
25:28 – The Transparency Dilemma: How to tell your team you are selling without causing a panic (The "Growth Capital" script).
(29:08) – The Halo Effect: Why hiring veterans and Special Ops leaders can transform your civilian workforce.
--
The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/
Smart Scaling, M&A Strategy, and Why Most Founders Raise Money Too Early with James Rose
The Exit - Presented By Flippa
28 minutes 45 seconds
1 month ago
Smart Scaling, M&A Strategy, and Why Most Founders Raise Money Too Early with James Rose
Want a quick estimate of how much your business is worth?
With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business.
You might be surprised by how much you can get for it: https://flippa.com/exit
--
If you're an entrepreneur wondering when to raise capital, how to scale through acquisition, or what really drives valuation multiples, this conversation delivers tactical advice you can actually use.
In this episode of The Exit Podcast, James Rose, Founder and CEO of Inflective Group, unpacks the strategic decisions that determine whether a business exits successfully or stalls out. James shares hard-won lessons from his journey building and selling businesses across Eastern Europe, spending over a decade in the startup world, and now helping agency founders navigate their own exits.
What You'll Learn
On Common Founder Mistakes:
Why raising money too early can make your business less acquirable
The hidden execution risks that come with rapid scaling
How hiring the wrong people costs you 18 months and momentum
Why one A-player delivers what five B-players struggle to achieve
On Exit Timing and Preparation:
Why the best businesses get bought, not sold
The truth about "exit prep" and when it becomes a distraction
How to know if you're actually ready to scale or should stay focused
What life-changing money really means at different stages
On Scaling and Valuation:
Why small operational improvements won't significantly change your multiple
The three paths to scale: raising capital, acquiring competitors, or joining a larger group
How to think about EBITDA multiples and what actually moves the needle
Why scale is the ultimate multiplier, not process optimization
On M&A and Deal Structure:
How to create competitive tension in negotiations (and why you need it)
The "longest list" negotiation strategy that actually works
Why most founders focus on the wrong deal terms
Red flags to watch for in private equity deals and earnout structures
How minority investments can empower founders instead of limiting them
On Growing Through Acquisition:
The financial commitment calculation: when will you actually see ROI?
Managing the distraction of M&A while protecting your core business
Why leverage matters more than scale in acquisitions
How to ensure people stay and remain motivated post-acquisition
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James Rose is Founder & Director of Rose Equity Partners and also leads as Founder & Group CEO of Inflectiv Group, bringing over two decades of entrepreneurial leadership in launching, scaling and advising high-growth media, marketing and technology ventures. He has driven commercial strategies and go-to-market execution for private-equity-backed companies while taking revenues from early stage through to £7M+ outcomes. With a deep passion for partnering with ambitious entrepreneurs and creating sustainable value, James combines operational expertise, investor insight and strategic vision to help founder-led businesses navigate growth inflection points and deliver meaningful impact.
Website - https://www.inflectivgroup.com/
LinkedIn - https://www.linkedin.com/in/jamesroseequitypartners/
--
The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/
The Exit - Presented By Flippa
Want a quick estimate of how much your business is worth?
With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business.
You might be surprised by how much you can get for it: https://flippa.com/exit
--
Are you building a business to own a job, or are you building an asset to sell? In this episode, Steve McGarry sits down with Chris Hallberg, Founder of Business Sergeant and an expert EOS Implementer, to dismantle the complexities of exiting a business.
Chris shares his personal journey from law enforcement to entrepreneurship, revealing the expensive mistakes he made during his first "fast and furious" exit. We dive deep into tactical preparation for a sale, including how to remove the "owner dependency" trap, the importance of business operating systems in driving up multiples, and how to navigate the ruthless "Fish and Chip" negotiation tactics used by buyers.
Whether you are looking to sell in 12 months or 10 years, this episode provides the blueprint for building a company that attracts top-tier buyers and maximum valuation.
In this episode, we cover:
--
Chris Hallberg is a high-energy entrepreneurial coach, facilitator, and Founder of GoExpand, an officially licensed EOS execution platform, dedicated to helping leadership teams build clarity, accountability, and healthy growth. As a seasoned Certified EOS Implementer®, Chris brings over a decade of full-time EOS experience working with companies across industries to align vision with execution and drive transformative results. Known for his direct yet kind communication style and practical mindset, he has helped more than 100 leadership teams foster world-class cultures and achieve measurable success. Chris blends disciplined operating system implementation with a people-first approach that empowers leaders to get what they want from their business and have fun doing it.
Websites - https://bizsgt.com/
- https://goexpand.com/
LinkedIn - https://www.linkedin.com/in/chris-hallberg-01516315/
--
Timestamps:
(00:24) – From Uniform to Suit: Chris’s transition from Military Police and Sheriff Deputy to high-growth entrepreneur.
(01:42) – The "Expedient" Exit Mistake: Why selling too fast cost Chris a fortune (and how to avoid it).
(03:31) – Golden Handcuffs: How to structure your leadership team so the business survives without you.
(07:14) – The "Fish and Chip" Model: Understanding the brutal reality of due diligence and last-minute price chiseling.
(10:23) – Timing the Market: Assessing trends (like AI) to know when your industry valuation has peaked.
(14:19) – Leadership Red Flags: Why "warm and fuzzy" leadership fails during the cold scrutiny of investment bankers.
(20:49) – Driving Valuation with EOS: How installing a Business Operating System can double or triple your multiple.
25:28 – The Transparency Dilemma: How to tell your team you are selling without causing a panic (The "Growth Capital" script).
(29:08) – The Halo Effect: Why hiring veterans and Special Ops leaders can transform your civilian workforce.
--
The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/