MATCHplay

Most owners think their business is worth what they've decided it's worth. Then they try to sell it and find out the hard way that dependency, the thing that made the business run smoothly for years, is the same thing that's now scaring buyers off. On this episode of MATCHplay, Thad Miller sits down with Ed Mysogland, Managing Partner of Indiana Business Advisors and author of the upcoming book Done Deal, to break down two of the most overlooked realities of selling a business: owner dependency and the real structure behind the number on a term sheet. Ed has closed nearly 2,400 transactions over three decades, all from the seller's side. He's seen every version of the deal that looked great on paper and fell apart in diligence, and every owner who thought the sale price was the whole story until they got to the fine print.

This episode is for any business owner who's thought about selling, is getting ready to sell, or just wants to understand what buyers are really evaluating.

What You'll Learn: • Why dependency on the owner is one of the fastest ways to kill a deal, regardless of industry • How to spot dependency risk in your own business before a buyer does • Why the headline price on a term sheet is only one line of the actual deal • What earnouts, employment agreements, and staff outcomes really mean for your bottom line • How to think about a sale from the seller's side, not just the buyer's

About the Guest: Ed Mysogland is the Managing Partner of Indiana Business Advisors, an Indiana business brokerage and M&A advisory firm with nearly 2,400 transactions closed. He is the author of Done Deal (releasing September 2026), a guide to the exit process written entirely from the seller's perspective, and the host of Defenders of Business Value, a podcast for advisors and owners who take business value and future business sales seriously. He lives in Carmel, Indiana with his wife and two daughters.

🎧 Listen to MATCHplay on Spotify- https://open.spotify.com/show/1gymVuZio3JiveegeNZ2RT?si=ea26bd704b8c4162

🎧 Listen to MATCHplay on Apple- https://podcasts.apple.com/us/podcast/matchplay/id1843210078

📺 Subscribe on YouTube for more conversations on entrepreneurship, leadership, and successful business exits - https://www.youtube.com/@MATCHplaypod

What does it actually feel like to sell a business you've spent decades building, and then stay?

In this episode of MATCHplay, Thad Miller sits down with Michael Bosway, longtime leader of City Securities Corporation, a firm with nearly a century of history and a reputation built on generations of relationships. After more than 30 years with the company, including serving as CEO, Mike led City Securities through its sale to Stifel Financial Corp., one of the fastest-growing national brokerages in the country.

But Mike didn't walk away. He stayed. And so did much of his leadership team. This conversation goes beyond the transaction. It's about how a business earns its reputation over time, how you know when selling is the right move even when you're not forced to, and what it means to choose a buyer you're willing to build with long after the deal closes.

If you're a business owner thinking about a future sale, or trying to understand what life on the other side of a transaction actually looks like, this episode is worth the full round.

What You'll Learn:

-What made City Securities a durable, respected firm across nearly 100 years

-How industry changes like regulation, scale, and competition shift the case for selling

-How to evaluate buyers when you plan to stay on after the acquisition

-Why cultural alignment can matter as much as financial terms

-What owners misunderstand about life after the deal, especially if they remain involved

-How to know whether selling is a proactive decision or a reactive one

About the Guest:

Michael Bosway served as CEO of City Securities Corporation, an Indiana-based financial services firm with nearly a century of history. He led the company's sale to Stifel Financial Corp. and continued in a leadership role following the acquisition, giving him a rare perspective on what it means to sell a business and remain accountable for what comes next.

🎧 Listen to MATCHplay on Spotify- https://open.spotify.com/show/1gymVuZio3Ji...

🎧 Listen to MATCHplay on Apple- https://podcasts.apple.com/us/podcast/matc...

📺 Subscribe on YouTube for more conversations on entrepreneurship, leadership, and successful business exits.

What does private equity actually look for when they buy a business?

In this episode of MATCHplay, Thad Miller sits down with Pete Munson, an operator and advisor who has spent years working alongside private equity groups on acquisitions, growth, and value creation.

Pete has seen deals from the inside. What gets attention, what gets passed on, and what ultimately determines whether a business becomes a success story or a missed opportunity. He breaks down the real evaluation process, what separates a business that gets serious offers from one that gets overlooked, and where most founders misread the game before they even sit down at the table.

This conversation is for any business owner who has ever wondered how private equity actually thinks, or who wants to build something worth buying one day.

What You'll Learn:

-What private equity looks for the moment they see a business for the first time

-The non-negotiables that have to be present for a deal to move forward

-How buyers weigh the numbers against the people running the business

-What separates businesses that get strong offers from those that get passed on

-Why deals that look good on paper sometimes fall apart, and where the breakdown usually happens

-What founders misunderstand about the ultimate goal of private equity after a deal closes

-What to think through before entering any PE process, and who is a good fit versus who probably isn't

About the Guest:

Pete Munson is the Managing Director at Cardinal Equity Partners, where he works closely with private equity groups on acquisitions, growth strategy, and value creation. He brings a practitioner's perspective to how deals are evaluated, structured, and ultimately won or lost, and what business owners need to understand long before the process begins.

🎧 Listen to MATCHplay on Spotify- https://open.spotify.com/show/1gymVuZio3JiveegeNZ2RT?si=ea26bd704b8c4162

🎧 Listen to MATCHplay on Apple- https://podcasts.apple.com/us/podcast/matchplay/id1843210078

📺 Subscribe on YouTube for more conversations on entrepreneurship, leadership, and successful business exits - https://www.youtube.com/@MATCHplaypod

What does it really take to know when it is time to walk off the course?

In the Season 3 premiere of MATCHplay, Thad Miller sits down with Dr. David Cohen, who recently sold Glenview Animal Hospital with the help of DVMmatch, for an honest conversation about one of the biggest decisions a practice owner can make.

Dr. Cohen shares what it felt like to hand over something built on decades of relationships, why trust and transparency matter, and how he knew it was time to make the call, even without a formal exit plan in place.

He reflects on what it takes to become a trusted pillar in your community, how to lead and grow a practice you have acquired, the moment he picked up the phone and knew exactly who to call, and more.

If you are a practice owner thinking about your next chapter, this one is worth the full round.

🎧 Listen to MATCHplay on Spotify- https://open.spotify.com/show/1gymVuZio3JiveegeNZ2RT?si=ea26bd704b8c4162

🎧 Listen to MATCHplay on Apple- https://podcasts.apple.com/us/podcast/matchplay/id1843210078

📺 Subscribe on YouTube for more conversations on entrepreneurship, leadership, and successful business exits - https://www.youtube.com/@MATCHplaypod

What does it really take to prepare your business for a successful sale?

In this MATCHplay Season 2 wrap, Thad Miller breaks down key insights from top guests on business growth, EBITDA, leadership, and transition planning.

Learn why companies stall, how to overcome growth valleys, what buyers actually look for, and why financial transparency, strong balance sheets, and early preparation are critical.

This episode features highlights from leading voices in business, healthcare, and entrepreneurship, all focused on helping owners build stronger, more valuable companies.

Plus, a closing lesson from golf pro Tony Pancake on why success comes from mastering the fundamentals, both on the course and in business.

🎧 Listen to MATCHplay on Spotify- https://open.spotify.com/show/1gymVuZio3JiveegeNZ2RT?si=ea26bd704b8c4162

🎧 Listen to MATCHplay on Apple- https://podcasts.apple.com/us/podcast/matchplay/id1843210078

📺 Subscribe on YouTube for more conversations on entrepreneurship, leadership, and successful business exits - https://www.youtube.com/@MATCHplaypod

When is the right time to sell your business?

In this episode of MATCHplay, Thad Miller sits down with Doug Cole, co-founder of Performance Assessment Network, to talk about building fast, selling at the right moment, and what happens after the deal closes.

Doug helped grow Performance Assessment Network into one of the fastest-growing companies in the region before it was acquired for $75 million in just over five years. But the real story isn't just the number. It's how the decision to sell was made while the business still had momentum, and how he evaluated the right partner to carry it forward.

This conversation breaks down the tension every founder faces. Do you keep building and see how far it can go, or do you take the opportunity in front of you?

If you're building a business, thinking about an exit, or wondering how to time a sale, this episode will give you a real perspective from someone who's been through it.

What You'll Learn:

• How to know when it's the right time to sell your business
• The pros and cons of selling early vs. holding longer
• How to evaluate buyers beyond just price
• What it feels like to sell while the business is still growing
• What changes when you stay on after an acquisition
• How founders should think about timing, risk, and opportunity

About the Guest:

Doug Cole is the co-founder of Performance Assessment Network (PAN), a technology company focused on online hiring and assessment tools. Under his leadership, the company scaled rapidly and was acquired for $75 million. He remained involved following the acquisition, helping guide the company through its next phase of growth.

🎧 Listen to MATCHplay on Spotify- https://open.spotify.com/show/1gymVuZio3JiveegeNZ2RT?si=ea26bd704b8c4162

🎧 Listen to MATCHplay on Apple- https://podcasts.apple.com/us/podcast/matchplay/id1843210078

📺 Subscribe on YouTube for more conversations on entrepreneurship, leadership, and successful business exits - https://www.youtube.com/@MATCHplaypod

What is EBITDA, and why does it matter when selling a business? If you don't understand EBITDA and quality of earnings, you don't understand what your business is actually worth.

In this episode of MATCHplay, Thad Miller sits down with Matt Howard, Director at Blue & Co. LLC, to break down the language every business owner hears during a sale but few actually understand. Matt specializes in business valuation, transaction advisory, and quality of earnings, working on hundreds of deals across dental, veterinary, and small business markets each year. He lives inside the numbers that determine what a business is really worth and what actually holds up when buyers take a closer look. This conversation cuts through the noise and explains, in plain English, the terms that can make or break a deal. If you're planning to sell your business, thinking about valuation, or just want to understand how deals actually work, this episode is for you.

What You'll Learn:

• What EBITDA really means (and why it's often misunderstood)
• How "add-backs" work and where owners get it wrong
• What a Quality of Earnings (QoE) report is and why buyers require it
• The difference between headline valuation and real deal value
• What terms like JV and HoldCo actually mean in a transaction
• How deal structure impacts what you walk away with

About the Guest:

Matt Howard is a CPA, Accredited in Business Valuation (ABV), and Certified Valuation Analyst (CVA). As a Director in the Transaction Advisory Services Group at Blue & Co., he provides valuation, due diligence, and consulting services for businesses across the United States.

Listen to MATCHplay on Spotify- https://open.spotify.com/show/1gymVuZio3JiveegeNZ2RT?si=ea26bd704b8c4162

Listen to MATCHplay on Apple- https://podcasts.apple.com/us/podcast/matchplay/id1843210078

Subscribe on YouTube for more conversations on entrepreneurship, leadership, and successful business exits - https://www.youtube.com/@MATCHplaypod

What does it take to build a company someone else wants to buy?

In this episode of MATCHplay, Thad Miller sits down with Tim Donnar, founder of Reindeer Logistics, to talk about entrepreneurship, long-term business building, and the moment every founder eventually faces — deciding whether it's time to sell.

Tim started Reindeer Logistics in 1997 from his basement after working in the moving industry with Mayflower. What began as a small third-party logistics service grew into a company with more than 90 employees and a strong reputation across the industry.

After nearly two decades of steady growth, private equity firms began approaching Tim with acquisition offers. He turned down several before ultimately deciding the timing and partnership were right to sell in 2016.

Today, Tim serves on the board and watches the company continue into its next chapter. This conversation explores what founders should focus on if they want to build a business with real long-term value — and how to recognize the moment when it's time to let the company move forward without you.

In this episode, we discuss: • Starting a logistics company from a basement in 1997 • Identifying opportunity in the moving and relocation industry • Building reputation, relationships, and operational strength • Growing Reindeer Logistics to more than 90 employees • The first time a private equity firm approached to buy the company • Why Tim turned down multiple acquisition offers • How founders evaluate when the right deal finally appears • What it feels like to sell the company you built • The transition from founder to board member • What makes a company attractive to buyers • Advice for entrepreneurs hoping to build a sellable business

🎧 Listen on Spotify: https://open.spotify.com/show/1gymVuZio3JiveegeNZ2RT?si=c1bb4ed2a1804751

🍎 Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/matchplay/id1843210078

📺 Subscribe on YouTube for more conversations on entrepreneurship, leadership, and successful business exits: https://www.youtube.com/@MATCHplaypod

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What separates companies that stall from those that accelerate?

In this episode of MATCHplay, Thad Miller sits down with Sohrab Motaghedi, Co-founder and Vice President of Operations at ClarionDoor, to explore the moments in business when momentum shifts — and what it takes to recognize opportunity early and act with conviction.

Rob has spent more than 20 years working in the InsureTech space, helping insurance companies distribute and manage their products through technology. Over the course of his career, he has helped build two successful startups from the ground up — guiding them through growth, scale, and ultimately acquisition.

This conversation dives into entrepreneurship, operational leadership, startup growth, and the real moments when preparation, timing, and opportunity collide.

For founders, operators, and business leaders looking to scale companies or navigate growth stages, Rob shares practical lessons on building teams, capitalizing on inflection points, and sustaining momentum in competitive industries.

In this episode, we discuss: • What draws entrepreneurs into the startup world • Early lessons from working inside fast-growing tech companies • The realities of scaling a software business • Why operational strength determines whether companies grow or stall • "Lightning in a bottle" moments that accelerated ClarionDoor's growth • How LinkedIn networking helped spark unexpected business opportunities • The role of cloud technology and timing in InsureTech expansion • Building teams that can execute under pressure • Transitioning from hands-on operator to strategic leader • The systems founders need before growth hits • Common mistakes entrepreneurs make during expansion • Advice for founders waiting for their own inflection point

🎧 Listen to MATCHplay on Spotify, Apple Podcasts, and wherever you get your podcasts.

Spotify: https://open.spotify.com/show/ 1gymVuZio3Ji..

Apple: https://podcasts.apple.com/us/ podcast/matc...

📺 Subscribe on YouTube for more conversations on entrepreneurship, leadership, and successful business exits.

Youtube: https://www.youtube.com/@MATCHplaypod

📲 Follow MATCHplay for episode clips, leadership insights, and updates.

LinkedIn: https://www.linkedin.com/posts/matchplay-podcast_matchplay-activity-7384933454620127232-omt3/

Instagram: https://www.instagram.com/matchplaypodcast?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==

What does it take to build a healthcare practice that actually reflects your values — and could one day become a sellable asset?

In this episode of MATCHplay, Thad Miller sits down with Dr. Tanya Lawson, licensed naturopathic doctor, functional medicine expert, and founder of In Bloom Health in New Hampshire, to talk about redefining patient care — and what it takes to build a modern, purpose-driven healthcare business.

Dr. Lawson shares her journey from conventional clinical settings to launching a root-cause, functional medicine practice designed around personalization, prevention, and long-term patient relationships.

But this conversation goes beyond medicine.

It's about: • Stepping outside traditional systems • Building a differentiated healthcare model • Creating brand trust in a niche market • And developing a practice that isn't just fulfilling — but valuable.

For healthcare entrepreneurs, practice owners, and founders thinking about growth, scalability, or eventual transition, this episode offers powerful perspective.