Timing the Exit with Doug Cole

Season 2 Lessons on Growth, EBITDA, and Leadership

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 [https://open.spotify.com/show/1gymVuZio3JiveegeNZ2RT?si=ea26bd704b8c4162] 🎧 Listen to MATCHplay on Apple- https://podcasts.apple.com/us/podcast/matchplay/id1843210078 [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 [https://www.youtube.com/@MATCHplaypod]

Timing the Exit with Doug Cole

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 [https://open.spotify.com/show/1gymVuZio3JiveegeNZ2RT?si=ea26bd704b8c4162] 🎧 Listen to MATCHplay on Apple- https://podcasts.apple.com/us/podcast/matchplay/id1843210078 [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 [https://www.youtube.com/@MATCHplaypod]

WTF is EBITDA - Matt Howard CPA, CVA

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 [https://open.spotify.com/show/1gymVuZio3JiveegeNZ2RT?si=ea26bd704b8c4162] Listen to MATCHplay on Apple- https://podcasts.apple.com/us/podcast/matchplay/id1843210078 [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 [https://www.youtube.com/@MATCHplaypod]

Tim Donnar on Selling Reindeer Logistics

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 [https://open.spotify.com/show/1gymVuZio3JiveegeNZ2RT?si=c1bb4ed2a1804751] 🍎 Listen on Apple Podcasts: https://podcasts.apple.com/us/podcast/matchplay/id1843210078 [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 [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/ [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== [https://www.instagram.com/matchplaypodcast?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==]

Building & Scaling an InsureTech Company

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.. [https://open.spotify.com/show/1gymVuZio3JiveegeNZ2RT?si=0ba4b9325abc48bf] Apple: https://podcasts.apple.com/us/ podcast/matc... [https://youtu.be/1Wn6vx_Rkks] 📺 Subscribe on YouTube for more conversations on entrepreneurship, leadership, and successful business exits. Youtube: https://www.youtube.com/@MATCHplaypod [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/ [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== [https://www.instagram.com/matchplaypodcast?utm_source=ig_web_button_share_sheet&igsh=ZDNlZDc0MzIxNw==]