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

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In this episode of The Exit, we sit down with Joshua Gould, CEO of thebigword, who shares his journey from joining a small family business to scaling it into a $100 million company and ultimately selling a majority stake. Joshua breaks down the realities of bootstrapped growth, the sacrifices required to reinvest every dollar back into the business, and the turning point where he shifted from chasing revenue at all costs to building a company that could actually be sold.

We dive into what it really means to “run your business like a private equity firm,” including why most founders leave millions on the table by not preparing early enough, how to think about every expense as a multiple of your eventual exit value, and the critical importance of having the right financial leadership in place. Joshua also shares hard-earned lessons on timing your exit, avoiding common deal mistakes, and why selling when you don’t have to is often the smartest move. Whether you are scaling toward your first exit or optimizing for long term value, this episode is packed with practical insights on building a business that buyers actually want.

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Joshua Gould is a seasoned executive with over two decades of C-level leadership experience across the technology, defense, consumer packaged goods, and healthcare sectors. Currently as the CEO of thebigword, he has built a reputation for driving strategic growth, operational excellence, and innovation within complex organizations. Known for his ability to scale businesses and lead cross-functional teams, Gould brings a global perspective to leadership, combining commercial insight with a strong focus on delivering measurable results.

LinkedIn - https://www.linkedin.com/in/joshuadgould/

The Exec Craft Podcast - https://www.youtube.com/@exec_craft

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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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In this episode of The Exit, we sit down with Jeremy Harbour, a legendary dealmaker who has mastered the art of small-business M&A. Jeremy has spent decades building, buying, and selling businesses across the globe, and today, he’s sharing his unconventional wisdom on how to scale through acquisition—without the traditional "grind" of organic growth.



We explore why starting a business is often a "broken" model and why buying an existing, cash-flowing company is the ultimate shortcut to wealth. Jeremy breaks down his famous "no-money-down" deal structures, the importance of creating win-win scenarios for sellers, and how his Agglomeration strategy allows small businesses to play in the big leagues of public markets.



Whether you're looking to make your first acquisition or planning your ultimate exit, Jeremy’s practical, no-nonsense approach to deal-making is a masterclass in financial engineering and entrepreneurship.



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Jeremy Harbour is an entrepreneur and dealmaker, based in Dubai, who has built, bought, fixed, and sold numerous small and mid‐sized businesses over several decades. As founder of the Harbour Club and CEO and founder at Unity Group, he specialises in small‐business M&A and acquisition, entrepreneurship, and helping business owners grow through buying companies rather than starting from scratch. Jeremy is known for his practical no‐nonsense approach to doing deals, structuring win‐wins, and helping entrepreneurs create real wealth through private company ownership and public listings.




LinkedIn - https://www.linkedin.com/in/jeremyharbour/ 



Website - https://www.harbourclubevents.com/

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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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Have you ever wondered why two identical businesses can sell for vastly different prices? One owner walks away with generational wealth, while the other settles for a steep discount and "unattractive" terms.

In this episode of The Exit, Steve McGarry sits down with Cameron Bishop, the Managing Director at Raincatcher, to pull back the curtain on the high-stakes world of M&A. From his humble beginnings as an advertising copywriter to scaling a company to $400 million with 2,000 employees, Cameron has been in the driver’s seat of over 90 buy-side and sell-side deals.

Today, he’s sharing the tactical "cheat sheet" every founder needs to maximize their valuation and avoid the mistakes that kill deals in diligence.


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Cameron Bishop is an experienced executive and entrepreneur known for driving growth and transformation across media and education businesses. He began as a copywriter and rose to CEO of Intertec Publishing, scaling it into a $400 million global enterprise, and later co-founded Ascend Media, growing it into a $120 million company backed by JP Morgan Chase. Cameron has also advised private business owners on exit strategies through Capitus and served as CEO of SkillPath Seminars, where he led a successful turnaround through rebranding, operational improvements, and digital innovation. Today, he works with entrepreneurs to navigate challenges, maximize value, and unlock new growth opportunities.

LinkedIn - https://www.linkedin.com/in/cameron-bishop-19b6804/

Website - https://raincatcher.com/

[00:20] – Cameron’s "unusual" journey: From advertising copywriter to Managing Director.


[01:10] – Scaling a $7M business to a $400M powerhouse with 2,000 employees.


[02:44] – The Essential Question: What are the common mistakes that kill deals in diligence?


[05:37] – The 95/5 Rule: Why working on your business is more important than working in it.


[09:00] – The "Accounting Horror Stories" and why GAAP accrual is a non-negotiable for buyers.


[10:45] – The Owner Dependency Trap: Passing the "Vacation Test".


[14:00] – The "Fish and Chip" Method: How to protect your valuation from "retrading".


[15:30] – The power of Sell-Side Diligence and why it's a "full-time job on top of a full-time job".


[22:00] – Case Study: How a competitive bidding environment turned a $19M valuation into a $28M exit.


[24:43] – How to connect with Cameron and the team at Raincatcher.


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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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Blake Hutchison, CEO of Flippa, the world's largest marketplace for buying and selling digital businesses, joins Steve McGarry to unveil Broker AI: a suite of AI-powered tools that's set to transform how small business M&A gets done. From AI agents that source deals and qualify buyers, to automated P&L builders and multilingual deal rooms, this episode breaks down how Flippa is democratising business brokerage for entrepreneurs around the world.


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Blake Hutchison is the Chief Executive Officer of Flippa, the online marketplace that enables buying and selling of websites, apps, stores, and digital businesses. Since taking the helm in late 2018 as a turnaround CEO, Blake has driven Flippa’s growth and led a global team focused on empowering entrepreneurs and small business owners to exit on their terms and own their future.


LinkedIn - https://www.linkedin.com/in/blakehutchison/ 

Check Out Flippa’s Partner Program - https://flippapartners.com/ 



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Key Moments:
00:00 - Introduction — Blake Hutchison returns to The Exit
00:55 - Why business brokers are the heart of small business M&A
02:30 - Introducing Broker AI and the Certified Flipper Broker Partner Program
04:30 - Who should apply — the ideal broker partner profile
07:43 - Inside the brokerage process: deal sourcing, Lauren AI, and how leads work
09:00 - The P&L Builder: building SDE-adjusted financials for M&A
10:30 - The IM Generator and the 7 agents running on the platform
12:14 - Meet Brian and Lauren — the AI agents with names
14:28 - Going global: why the program is open worldwide
18:00 - Real-world example: Brokerall in Rome and the Italian Amazon FBA community
21:03 - Multilingual deal rooms in action
24:00 - Which asset types are hottest right now: Ecom, YouTube, and what's cooling
25:19 - The state of AI: fear, opportunity, and what Blake built himself this week
31:45 - Where to learn more and how to apply

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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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In this episode, Steve McGarry sits down with Tyson Ray, CEO of Form Wealth Advisors and a certified exit planner. With over 27 years in the financial services industry, Tyson shares his journey from a childhood shaped by financial hardship to becoming a guide for business owners facing their inevitable "exit."


Whether you plan to sell next year or die at your desk, Tyson explains why every entrepreneur needs a succession plan. He introduces his signature SPACE framework and discusses the critical psychological shifts required to successfully transition away from a business you've spent a lifetime building.



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After nearly 30 years building a successful financial advisory practice, Tyson Ray realized his assumed succession plan was actually built on unchecked assumptions that could put everything at risk. That moment of reflection inspired his book Total Succession, the SPACE™ framework (See, Prepare, Act, Commit, Exit), and The Total Succession Show podcast, where he helps financial advisors exit their businesses with clarity and confidence. Tyson encourages advisors to confront difficult questions about leadership, client protection, and letting go, with one clear message: it is never too late to get succession planning right.

LinkedIn - https://www.linkedin.com/in/tysonray/ 

Website - https://formwealth.com/ 



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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/