316 episodes
Know When to Walk Away: Elliot Omanson on Exit Timing, Tax Strategy, and Keeping What You’ve Earned
05/10/2026 | 34 mins.On this episode of The Exit, presented by Flippa, Steve McGarry sits down with Elliot Omanson, CEO of OWLFI, to discuss the decisions that determine whether an owner walks away from an exit with wealth preserved—or leaves money on the table.
Elliot explains how to know when to walk away, how to think about exit timing, and why tax strategy should be part of the plan well before a transaction closes. They also discuss Elliot’s book, Keep What You’ve Earned, and practical ways business owners can protect the wealth they’ve built.
Learn more:
OWLFI: https://owlfi.com
Elliot Omanson: https://elliotomanson.com
Connect with Elliot on LinkedIn: https://www.linkedin.com/in/elliot-omanson/
Get your Flippa business valuation: https://flippa.com/exit
The Exit is 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
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What does it take to build a company around your personal brand, then make yourself unnecessary to its success? On this episode of The Exit, Steve McGarry sits down with Heath Adams, founder of TCM Security and co-founder of Breach Point, to unpack his journey from ethical hacker and content creator to building, scaling, and ultimately selling a cybersecurity company. Heath shares how a penetration testing consultancy unexpectedly evolved into an education business after his first Udemy course generated $100,000 in its first week, and how content, community, and word of mouth became powerful engines for the company’s growth.
Heath also breaks down the work that went into preparing TCM Security for an eventual exit, including delegating responsibilities, reducing founder dependency, and building a company that could operate without him. He walks Steve through the sale process, from taking acquisition conversations seriously and hiring an M&A firm to receiving multiple offers and choosing strategic fit over the highest bid. They also discuss keeping the deal confidential while running the business, rewarding the team after the acquisition, and why founders should never assume a deal is done until the money is in the bank. Finally, Heath opens up about the unexpected loss of identity that can follow an exit and how that experience is shaping his next chapter as co-founder of Breach Point and Insight Recon.
Key Takeaways:
Reduce founder dependency before you plan to sell.
Delegate early and build a team that can operate without you.
Never say no to an acquisition conversation.
Multiple offers can create leverage during negotiations.
Strategic fit can matter more than the highest offer.
A deal is not done until the money is in the bank.
Plan for your purpose and identity after the exit.
Personal &/or Company Bio:
Heath Adams, known online as The Cyber Mentor, is an ethical hacker, educator, and entrepreneur. An Army veteran, he founded and served as CEO of TCM Security, a cybersecurity services and training company he bootstrapped from nothing to an eight-figure exit with no outside capital. Heath has taught cybersecurity to more than a million students across YouTube, Udemy, and TCM Security Academy. He holds an MBA and recently appeared in the documentary Midnight in the War Room. Today he builds software at Breach Point and writes The Heath Adams Letter weekly for more than 34,000 subscribers.
LinkedIn - https://www.linkedin.com/in/heathadams/
Websites - https://breachpoint.com/
- https://insightrecon.com/
- https://heathadams.com/
Key Chapters:
00:01 Welcome and Episode Previ03:20 Introduction and Heath's background in ethical hacking
05:28 Starting a pen testing consultancy and initial sales process
06:50 Transition from service to educational business model
08:17 Scaling the business and reducing founder dependency
09:46 Timing and reasons for exit
12:30 Approaching buyers and valuation negotiations
14:18 The sale process timeline and due diligence
18:22 Bidding, LOIs, and final negotiations
21:27 Post-sale team and brand management
22:38 Mistakes and lessons learned in building and selling a business
24:24 Advice to his past self and future entrepreneurs
25:55 Current projects: Breach Point and cybersecurity software
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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 Trend Is Your Friend: Selling at the Right Time and Avoiding the Wrong Buyer with Matt Bradbury
21/09/2026 | 28 mins.This episode was recorded prior to the passing of our guest, Matt Bradbury. We are honored to share this conversation and extend our heartfelt condolences to Matt’s family, friends, colleagues, and all those who knew him.
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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
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When is the right time to sell your business, and how do you know when the right buyer comes along? In this episode of The Exit, Steve McGarry sits down with Matt Bradbury, Founder and Managing Director of BAMA (Business Acquisition and Merger Associates), to discuss what business owners need to know before entering the M&A process. Matt explains why “the trend is your friend” when deciding when to sell, how consistent growth and strong margins can lead to a premium valuation, and why building a company that can operate without its owner makes for a much stronger exit.
Matt also shares what sellers should do to prepare their financials, why too many add backs can become a red flag, and how transparency can build trust before and during due diligence. He and Steve dig into buyer retrades, the tactics some firms use to chip away at a deal after the LOI, and why the highest offer is not always the best transaction. Matt also explains why having experienced M&A attorneys and advisors on your side can make the difference between protecting the deal you negotiated and watching it unravel before closing.
Personal &/or Company Bio:
Matt Bradbury is the Founder and Managing Director of Business Acquisition & Merger Associates (BAMA), a lower middle market M&A firm specializing in buy side, sell side, and management buyout transactions. With more than 35 years of experience supporting acquisitions and business sales, Matt began his career in the fitness industry, where he held leadership roles and worked on numerous acquisitions before founding BAMA. Today, he works with business owners and buyers across industries including manufacturing, distribution, industrial and environmental services, and health and fitness, helping clients navigate transactions and find the right partners for long term success.
LinkedIn - https://www.linkedin.com/in/bradburymatt/
BAMA Website - https://www.buysellyourbusiness.com/
Key Chapters:
00:01 Welcome and Episode Preview
02:14 Meet Matt Bradbury and His Unorthodox Career Path
04:15 From the Fitness Industry to M&A
05:53 The Businesses Matt Helps Buy and Sell
06:21 What Makes an Ideal Seller
09:33 Why Humility Matters in M&A
11:25 Knowing When It’s Time to Sell
14:06 Preparing Your Business for an Exit
16:32 Building Trust Through Transparency
21:05 Common Mistakes and Buyer Retrades
26:03 Lessons Matt Wishes He Knew Earlier
30:01 Matt’s Current Projects and Where to Connect
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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/- 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
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What does it take to build a business that buyers are willing to pay a premium for? On this episode of The Exit, Steve McGarry sits down with entrepreneur and exit expert Mark Mills OBE DL to unpack the strategies that helped him build and scale Cardpoint into a business generating nearly £100 million in annual revenue. Mark shares how an unexpected trip to New York sparked the idea for bringing independently operated ATMs to the UK, why he reverse engineered a 36 month growth plan down to a handful of critical KPIs, and how that disciplined approach helped the company come remarkably close to the ambitious targets he set.
Mark also breaks down what founders can start doing today to prepare for a successful exit, from building a repeatable customer acquisition engine to creating a clear growth plan that gives potential buyers confidence in the future of the business. He explains why founders should avoid appearing eager to sell, how continued growth can create leverage at the negotiating table, and why competition between buyers can increase both deal certainty and valuation. Plus, Mark shares a memorable story about literally walking away from a deal to protect its value and reveals the lesson he wishes he had learned earlier in his entrepreneurial career: refine your business model, stay focused, and do one thing exceptionally well.
Key Takeaways:
Reverse engineer your growth goals
Track the KPIs that actually matter
Build a repeatable sales engine
Prepare for an exit early
Don’t BE for sale
Grow from a position of strength
Create competition between buyers
Know when to walk away
Own your market
Focus on doing one thing exceptionally well
Personal &/or Company Bio:
Mark Mills OBE DL is an entrepreneur, business advisor, and exit expert who has spent decades building, scaling, and selling businesses. He founded Cardpoint plc in 2000 and grew the company to approximately £100 million in annual revenue and £19.8 million in EBITDA by 2006. Since 2007, Mark has used his firsthand experience to help other business owners prepare for and navigate successful exits, with a focus on accelerating growth, maximizing value, and negotiating from a position of strength. In 2022, he was appointed a Deputy Lieutenant of Lancashire, and in 2025, he was awarded an OBE for services to business and charity.
LinkedIn - https://www.linkedin.com/in/markrichardmills/
Website - https://mark.co.uk/
Key Chapters:
[00:01] Welcome and Episode Preview
[02:02] Introduction to Mark Mills OBE DL and His Entrepreneurial Journey
[03:59] The Story Behind Cardpoint and Finding the ATM Opportunity
[08:34] Scaling Cardpoint and Tracking the Right KPIs
[10:43] Reverse Engineering £100 Million in Revenue
[16:48] How to Prepare Your Business for an Exit
[21:29] Knowing the Right Time to Sell
[25:52] How to Increase Your Business Valuation
[29:26] Negotiating From Strength and Knowing When to Walk Away
[31:47] Mark’s Advice to His Younger Self
[33:02] What Mark Is Working on Now
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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 Charisma Trap: Charles Lee on Bad Investments, Founder Red Flags, and Building Toward an Exit
07/09/2026 | 30 mins.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
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What makes a business attractive to investors, and how do you know when it is truly ready to scale or sell? On this episode of The Exit, Steve McGarry sits down with Charles Lee, Founder and CEO of Ideation, to explore the lessons Charles has learned from nearly two decades of building his own company and investing in startups across multiple industries. Charles shares why valuations are often more subjective than founders realize, what he looks for during due diligence, and why the strength and honesty of the founding team can matter just as much as the numbers. He also explains why he has become cautious about investing in solo founders and why communication with investors can be an important indicator of how a company is being run.
Charles and Steve also discuss the pressures that come with building a venture backed company, the difference between growing and truly scaling a business, and why burnout is rarely the ideal reason to pursue an exit. Charles shares some of the investment mistakes that shaped his approach today, including rushing into opportunities and getting caught up in founder charisma. He also breaks down a company he has advised and invested in for nearly a decade, showing how patience, consistent innovation, profitability, and strong operations can ultimately put a business in a much stronger position for acquisition. His biggest lesson for founders and investors alike is simple: take your time, understand your risk, and do not let urgency make the decision for you.
Key Takeaways:
Don’t Rush the Deal
Founder Charisma Can Mislead
Valuation Is Subjective
Strong Teams Reduce Risk
Growth Isn’t Scale
Don’t Sell From Burnout
Sell With Momentum
Patience Creates Better Opportunities
Personal &/or Company Bio:
Charles Lee is the Founder and CEO of Ideation, a firm that helps brands scale their vision through strategic clarity and smart brand execution. He has worked with clients across industries including technology, financial services, venture capital, sports and entertainment, healthcare, nonprofits, and public institutions, serving as a trusted advisor to executives navigating innovation, brand building, and sustainable impact. Charles is also the author of two books with Wiley Publishing, Design Your Good Life and Good Idea. Now What?
LinkedIn - https://www.linkedin.com/in/charlestlee/
Ideation Website - https://theideation.com/
Check out his latest book Design Your Good Life - https://a.co/d/0iufNbAT
Key Chapters:
[00:01] Welcome and Episode Preview
[02:31] Charles Lee’s Background
[04:05] How Social Media Marketing Has Changed
[05:14] Creating Content People Actually Care About
[06:07] Charles Lee’s Business and Investment Journey
[08:24] Understanding Valuation and Its Subjective Side
[11:10] What Investors Look for in a Business
[16:14] Common Startup Investment Mistakes
[20:52] Exit Timing and Founder Burnout
[24:02] Charles Lee’s Advice to His Younger Self
[25:48] Current Projects and a Business Built for Acquisition
[28:58] Why Continuous Innovation Matters
[29:15] Where to Find Charles Lee and His Books
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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/
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About The Exit - Presented By Flippa
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 https://flippa.com/the-exit-podcast/
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