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REPLAY: How Circle City Capital Group Turns Overlooked Businesses Into Thriving Investments

Defenders of Business Value

Release Date: 12/24/2025

EP 148: What 4 Exits Taught TK Herman About Business show art EP 148: What 4 Exits Taught TK Herman About Business

Defenders of Business Value

Building a business is challenging, but truly understanding its value and how to maximize it is where many entrepreneurs fall short. , entrepreneur, four-time exit veteran, and Curator at , breaks down what it actually takes to build and sell a business at maximum value. Learn why most founders leave money on the table, what TK would do differently across his four exits, and why working on yourself may be the highest-return investment you make in your business.  If you're building to sell, this is a look at what separates the deals that close well from the ones that don't. In this...

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EP 147: How to Earn the Preferred Buyer Status show art EP 147: How to Earn the Preferred Buyer Status

Defenders of Business Value

Getting access to deals is one thing. Getting taken seriously is another. , Founder of , shares what it takes to get noticed by brokers and win deals. With hundreds of buyers competing for the same opportunities, the process has shifted. Systems, speed, and credibility now determine who moves forward and who gets ignored. Learn how preferred buyer status works, why most buyers fall short, and how technology is reshaping the way deals are sourced, screened, and closed. If you’re serious about buying a business, this is a look at how the process works behind the scenes. In this episode, you...

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REPLAY: The Next Generation of M&A: Trust, Tech, and the Human Side of Exits show art REPLAY: The Next Generation of M&A: Trust, Tech, and the Human Side of Exits

Defenders of Business Value

Most professionals in the M&A space have been closing deals for decades. But being young doesn’t mean you can’t bring value to the table. , founder of , has built a reputation as one of the younger voices in the industry. He has helped facilitate over $250 million worth of deals and is now using automation to make the process faster and more efficient. From the lessons learned in those transactions, he created the Breakwater Blueprint to keep deals from falling apart. Morgan offers a glimpse at the future of exits, where human connection and technology go hand in hand.   In this...

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EP 146: How to Overcome the Loneliness of Running a Small Business with Jared Luegers and Kevin King show art EP 146: How to Overcome the Loneliness of Running a Small Business with Jared Luegers and Kevin King

Defenders of Business Value

Owning a business can feel isolating. Entrepreneurs face daily challenges and tough decisions without others who truly understand their experience. A strong support network makes it easier to create long-term success and prepare for a smooth exit. In this episode, and , co-founders of , share how they’re helping business owners in Indiana create a supportive community and build lasting business value. They discuss the importance of overcoming the loneliness of entrepreneurship, the power of connecting with other operators, and how small businesses can leverage tools like AI to thrive....

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REPLAY: No One-Size-Fits-All: Amy Wirtz on Succession Without the Drama show art REPLAY: No One-Size-Fits-All: Amy Wirtz on Succession Without the Drama

Defenders of Business Value

Managing a business is tough enough on its own. But add family dynamics in the mix, and things get even more challenging. As a strategic advisor at , shares her expertise on navigating ownership transitions in multigenerational families. Amy discusses the challenges of balancing family relationships with business goals, offering insights on how to manage both for a successful transition. She also shares tips to help prepare the next generation for leadership to ensure that both the business legacy and family harmony are preserved. In this episode, you will: Learn how to create a clear...

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EP 145: Avoid Paying the Deal Distraction Tax show art EP 145: Avoid Paying the Deal Distraction Tax

Defenders of Business Value

Picture this: You’re a business owner ready to sell your company. Your focus starts to shift from running the business to managing the deal. Soon, your numbers start to dip. The buyer notices and begins to question the value of your business. In this episode, breaks down the concept of the "Deal Distraction Tax. Whether you're in the middle of a deal or preparing to sell in the future, Ed shares crucial strategies for protecting your business value during this critical time.   In this episode, you will: Find out how distractions during a sale can lead to a decline in business value ...

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REPLAY: The Story That Sells Your Business with Charlie Stanton show art REPLAY: The Story That Sells Your Business with Charlie Stanton

Defenders of Business Value

In a business appraisal, the numbers will always matter — but how they’re communicated can have just as much impact on value. , CFA and founder of , believes every valuation tells a story. Drawing from his work in estate planning, litigation, and succession, he explains how storytelling can transform the way a business’s worth is understood. This episode explores the eight elements every appraisal story should include, why owning your narrative builds buyer trust, and how a clear, consistent story can make your business more saleable. In this episode, you will: Learn how to communicate...

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EP 144:  Indiana Business Investor Edition show art EP 144:  Indiana Business Investor Edition

Defenders of Business Value

One of the best things about running my own podcast is the freedom to experiment. Over the years, I've been first on a few things — building our original website from scratch, launching our first newsletter, and starting the podcast. Today, I'm trying something new again. I loaded several of our current business teasers into AI, and it generated a podcast episode around them. But here's what makes this more than a novelty: in the show notes, you'll find a direct link to the full business profile and NDA. Why does that matter? Buyers tell me constantly that they hear about good opportunities...

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EP 143: Women Entrepreneurs Breaking the Mold with Gabrielle Rubenstein show art EP 143: Women Entrepreneurs Breaking the Mold with Gabrielle Rubenstein

Defenders of Business Value

Many people think that once you buy a business, you’re set for life. But the reality is, there’s a lot of hard work that comes before you can reap the rewards. In this episode, takes us through her first year as an entrepreneur after acquiring in 2024. From navigating the challenges of scaling to overcoming the growing pains that come with ownership, she shares the lessons learned, the surprises along the way, and how she’s turned her acquisition into a thriving, growing business. Tune in for an honest conversation about the ups, downs, and everything in between in that crucial first...

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EP 142: How Chris Fredericks is Reinventing Small Business Ownership show art EP 142: How Chris Fredericks is Reinventing Small Business Ownership

Defenders of Business Value

Selling your business to a new buyer isn’t the only way to exit. What if you could transition ownership to your employees, rewarding their hard work while securing your legacy?  In this episode, , CEO at , discusses Employee Stock Ownership Plans (ESOPs) and how they offer a powerful alternative to traditional exit strategies. Chris explores the advantages of ESOPs and other employee ownership models, such as co-ops and Employee Ownership Trusts (EOTs). He shares examples of how these models help businesses thrive and create lasting value for both owners and their teams. If you’re...

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More Episodes

What really makes a business attractive to buyers? Buyers weigh more than just financials. They consider risk, operations, and whether the business can run without you.

Colin King and Joe Van Deman, Principals at Circle City Capital Group, Inc., know this firsthand. They’ve built a portfolio of 15 companies by acquiring businesses that many others have overlooked. Colin, a CPA and CFA, and Joe, a former Google employee, bring complementary skills for buying and growing companies. Their perspective offers owners a rare look at how serious buyers evaluate opportunities and negotiate deals.

 

In this episode, you will:

  • Hear how buyers assess both financial and emotional factors in a deal

  • Learn what makes a business unappealing to buyers right away

  • Find out what makes a partnership last through tough deals

 

Highlights:

(00:00) Meet Colin King and Joe Van Deman

(02:29) How a Craigslist ad launched their partnership

(07:37) Lessons from their first chaotic acquisition

(11:32) What makes a business partnership work

(15:50) How Circle City Capital Group is different from private equity

(23:08) Turning risky businesses into profitable opportunities

(33:03) Favorite companies in their portfolio

(36:13) What instantly turns buyers off during negotiations

(44:20) The changes that make businesses more sellable

 

Resources:

For past guests, please visit https://www.defendersofbusinessvalue.com/

 

Follow Colin:

Connect on LinkedIn: https://www.linkedin.com/in/colin-king-cpa-cfa-37045a38/

 

Follow Joe: 

Connect on LinkedIn: https://www.linkedin.com/in/joevandeman/


Check out their portfolio of companies:
Circle City Capital Group: http://circlecitycapitalgroup.com

Profit Mastery: http://profitmastery.net

The Vermont Flannel Company: https://www.vermontflannel.com/

Vermont Teddy Bear: https://vermontteddybear.com/

All American Clothing Co.: https://www.allamericanclothing.com/

Gusset Brand: https://gusset.com/

Silk Flower Depot: https://e-silkflowerdepot.com/

Dried Decor: https://www.drieddecor.com/

Montessori 'n Such: https://www.montessori-n-such.com/

Follow Ed:

Connect on LinkedIn: https://www.linkedin.com/in/edmysogland/

Instagram: https://www.instagram.com/defendersofbusinessvalue/

Facebook: https://www.facebook.com/bvdefenders