Business Spotlight with Tim Oleszczuk from TKO Miller

In this interview, Tim Oleszczuk, the managing director and co-founder of TKO Miller, provides valuable insights into his career journey and the work his company does in advising family- and founder-owned businesses during the sale process. TKO Miller specializes in helping business owners navigate the complexities of selling their companies, ensuring they capture the full value of their business rather than accepting lower offers due to lack of market insight or accurate information. With experience advising on transactions totaling billions of dollars, Tim emphasizes the importance of educating sellers to level the playing field and maximize the value of their businesses.

Tim also discusses his personal journey, from growing up on a farm in Wausau, Wisconsin, as the youngest of 18 children, to building TKO Miller into a successful firm. His leadership style focuses on empowering his team, teaching them to lead by example while allowing them the space to grow. Tim values trust, integrity, and communication, both in his personal life and business. He believes that fostering a strong team environment and encouraging young people to learn from their mistakes are key elements of success.

 

Podcast Transcript:

Kory Dogs: Hi everyone, this is Kory Dogs with ActionCOACH Business Coaching. I’m excited to have Tim Oleszczuk from TKO Miller with us today. Tim is the managing director at TKO Miller, specializing in middle-market mergers and acquisitions, with a focus on advising family- and founder-owned companies during the business sale process.

Tim brings exceptional leadership and extensive expertise to an underserved market, managing national and Midwestern middle-market transactions. Over his career, he has advised on deals totaling approximately $3 billion in aggregate value. Before co-founding TKO Miller, Tim was a managing director and general counsel at Grace Matthews, a Milwaukee-based boutique investment bank. There, he concentrated on the manufacturing and industrial services sectors, completing nearly 20 deals for Safway, one of the largest scaffolding companies in the U.S.

Prior to that, Tim was a shareholder at Godfrey & Kahn, focusing on mergers and acquisitions, corporate finance, and insurance law. He also founded Silicon Pastures, a network of Midwestern angel investors supporting early-stage companies with high growth potential. Tim earned his BBA and MBA in finance and risk management, both summa cum laude, from the University of Wisconsin-Madison, and his law degree from the University of Michigan.

We’ll learn more about TKO Miller shortly, but first, I’m happy to welcome Tim to the show. Hello, Tim!

Tim Oleszczuk: Hi, Kory. Thanks for having me. From that intro, it might sound like I was all about studying, but trust me, I had a lot of fun in college too!

Kory: That’s good to hear! Striking a balance is key, even in business—you’ve got to have some fun too.

Tim: Absolutely, 100%.

Kory: Before we dive into the questions, I want to share three fun facts about Tim. First, he’s the youngest of eighteen children.

Tim: That’s right.

Kory: How did you even fight for dinner?

Tim: Well, we only had 14 living at home at any given time, so that helped! But mealtime was competitive—if you paused, a fork might come over to take your food. It wasn’t a matter of whether you cleaned your plate—someone would do it for you. We didn’t have much money, but we raised beef cows, corn, and cucumbers. Let me tell you, the worst job in the world is picking cucumbers. You crawl in the dirt, pick these sharp things, and they stick to your fingers with sap. After a day of that, you’re determined to study hard so you don’t end up doing it again!

Kory: Tim’s favorite pastimes include traveling and attending Wisconsin Badgers and Michigan Wolverines football games. For those wondering, when the two teams play, he cheers for the Badgers! Finally, he’s most proud of founding TKO Miller and building it into what it is today.

Now, Tim, tell us more about your personal journey—where were you born and raised?

Tim: I grew up in Wausau, Wisconsin. It was a great place to grow up, but there’s a story behind the 18 kids. My dad passed away when I was seven, leaving five kids. My mom later remarried a man with 13 children of his own. While only 14 of us lived in the house at once, it was still a full house! We built a seven-bedroom home with two laundry rooms, and I’ve been doing my laundry since I was eight.

We lived on a farm, grew much of our food, and worked hard. My mom instilled in me the importance of studying so I wouldn’t have to do physically demanding jobs forever. I always wanted to be a lawyer, but I first earned a business degree because my mom encouraged me to have a fallback plan. I graduated with degrees in finance and insurance, got an MBA, worked for the insurance commissioner, taught a business school class, and even co-authored a paper with my professors. Afterward, I went to law school at the University of Michigan and joined Godfrey & Kahn, a top Milwaukee law firm, practicing there for 10 years before transitioning to investment banking.

Kory: Thanks for sharing, Tim. Let’s talk about TKO Miller. What inspired you to start it?

Tim: TKO Miller is a middle-market investment bank that helps people sell their businesses. In Wisconsin, investment banking services were scarce for founder- and family-owned businesses. Often, these business owners would receive unsolicited offers from buyers and sell for far less than their businesses were worth because they didn’t know any better.

Selling a business is a zero-sum game—if your business is worth $30 million and you sell it for $20 million, the buyer instantly gains $10 million at your expense. Our goal at TKO Miller is to educate sellers, ensuring they capture the full value of their businesses.

We focus on leveling the playing field. Buyers often have extensive experience, having acquired 100 businesses, while most sellers only sell once. We bring the expertise from the hundreds of deals we’ve completed to match the buyer’s knowledge and ensure sellers get what they deserve.

Ultimately, if a seller wants to give away money, they should choose to donate to a cause they care about—not unknowingly hand it over to a buyer. At TKO Miller, we emphasize education through speaking engagements and articles to empower sellers. It’s been incredibly rewarding to help so many businesses in Wisconsin and beyond.

Kory: That’s great. You only get one chance to sell a business, right? If the field’s tilted against you, like you’ve mentioned, there’s no going back. It’s a one-time opportunity.

Tim: Yeah, exactly. The challenge is there’s so much misinformation out there. People often get their information from friends at the club, their lawyer, or their accountant. But every situation is different.

Sometimes at a cocktail party, someone gives me two sentences of background and asks, “What’s my business worth?” There are so many factors involved, and hopefully, I’m not giving them an answer right then. But with some historical financial information and 10 to 15 minutes of Q&A, I can give them a pretty good estimate.

Most times, they’re surprised. Often, when someone shows me an unsolicited offer—what we call a “tap on the shoulder”—they can do better. That said, we’re not the kind of advisors who always claim we can beat the offer. Sometimes, it’s actually a good deal.

The issue is that many business owners don’t have the right information about how businesses are valued. They might think they’re getting a great deal when, in reality, they’re not.

Kory: Leadership is such a key part of our professional and personal lives. There are so many styles out there. How would you describe yours?

Tim: Great question. My leadership style is very much about leading by example. I make sure people can see how I lead, but I also believe in giving them space to learn.

It’s like taking them a little off the dock and tossing them into the water—not too far, though. I’m right there, letting them make mistakes and learn from them. Over time, I’ve realized that my team members don’t always do things my way, and that’s okay. They need to develop their own style, and if they try to copy mine, it usually doesn’t work.

Sometimes, their first attempts don’t succeed, and I don’t say, “I told you so.” Instead, I focus on teaching them. Sure, we might lose a bit here and there, but they grow into better leaders. The sooner I can teach them to lead, the sooner I can step aside. It’s also more fulfilling for them and makes this a better place to work.

I avoid being in the weeds. I often ask, “Do you need me at this meeting?” If the answer is no, I step back. If it’s yes, then I’m there. This approach benefits clients, too. They get a skilled team member and still have access to my experience when needed.

Kory: You mentioned a bit about what you do, but can you elaborate on your ideal client or target market?

Tim: We primarily work with founder- and family-owned businesses—typically those going through their first sale. We don’t do much with private equity or financial buyers.

Our focus is on situations where we can add value. For example, with metal vendors, no matter how well I run the process, the valuation range is usually tight. But in cases where a business could be worth 10 times earnings versus six times with a less skilled advisor, our value is clear. Those are the types of clients we seek—ones who recognize the difference we make.

The industries we work in are diverse: industrial services, scaffolding, manufacturing, packaging, software, value-added distribution, and more. On the flip side, we don’t serve sectors like construction, restaurants, and real estate, where valuations are tighter and buyers harder to find.

Our goal is to work in markets with a broad set of buyers to foster competition. More competition means better offers, and we can play bidders against each other to maximize value.

Kory: Do you also represent buyers, or is it mostly sellers?

Tim: Good question. While we primarily represent sellers—probably 90% of the time—we do occasionally represent buyers.

This year, it’s more balanced: 70% sell-side and 30% buy-side. That’s due to specific expertise in areas like industrial services and scaffolding. For example, we’re helping a scaffolding client in the Mid-Atlantic expand their footprint east of the Mississippi.

In another case, we’re working with an industrial services client specializing in painting, insulation, and coatings. They’ve got new ownership and are aggressively investing capital.

The approach differs on the buy side. When selling, we want lots of bidders and competition. For buyers, we aim to isolate the seller. It’s two sides of the same coin—just a shift in strategy.

Kory: Different hat.

Tim: Yeah, that’s right, it helps. When you’re helping someone buy, and you hear what the seller or the seller’s banker is saying, you understand the words and phrases and know what they really mean. That knowledge is helpful in those situations.

Kory: So, what’s the size range of deals you typically work with? Is there a minimum or maximum deal size you’d consider?

Tim: Usually, the high side is around $100 to $150 million, but it varies. On the low end, it’s typically $20 million, though that can change depending on the situation. If I can add value at $10 million, that’s fine too. For example, a couple of years ago, we worked with a business doing $5 million in revenue and making $3 million in profit. It was a unique business in the packaging space, and we did very well for them. So it’s hard to generalize. But if you’re making more than $2 million in EBITDA, it’s definitely worth having a conversation. If it’s not a good fit, I’ll still try to connect you with someone who can help. But generally, if you’re at $2 million in EBITDA or cash flow, it makes sense to talk.

Kory: That’s helpful. Looking back, we all like to reflect. If you could go back to the start of your career, is there anything you’d do differently?

Tim: Yeah, I probably would’ve started my own firm a little earlier. I’ve had great partners along the way, but the fear of losing that steady paycheck always held me back. However, now that I’m calling the shots and building things my way, I’ve had a lot of fun. I’m really enjoying it.

Kory: As the co-founder of TKO Miller, many people have myths or stereotypes about business owners. Is there anything you’d like to share to dispel those myths?

Tim: I’m not sure what the myths are, but one thing I’ll say is that it’s important to have a good business partner you get along with and can communicate well with. Tammie Miller, Joe Froehlich, and I have been together from the start. Tammie and I had even worked together for 15 years before this. We’ve had maybe three disagreements, and one of them was over a Christmas gift. The key is making sure there’s logic and reason behind your decisions. Not every call will work out, but if there’s logic behind it, that’s what matters. As long as you’re thoughtful and not reckless, it’s usually going to work out. Trustworthiness, good character, and integrity are key. If you have those, you’re in a good spot.

Kory: What’s one of the most interesting insights or pieces of advice you’ve received recently that’s worth sharing?

Tim: I think the biggest insight is to get young people to grow up quickly and trust them. It’s tough to watch them fail sometimes, but they’ll learn from it.

Kory: Have you always felt that way?

Tim: Yes, that’s how we were taught at Godfrey & Kahn. It was always about “institutionalizing the client.” It wasn’t about being Joe’s client, it was about being Godfrey & Kahn’s client. We try to do that here—it’s not just Tim’s client, it’s TKO Miller’s client. I’m always available if they need me, but if they can go to the next person in line and get their questions answered, great. They usually figure out quickly that the next person is doing most of the work anyway, so they just go directly to them. That’s always been one of our guiding principles. It’s not about one person; it’s about the team.

Kory: So it’s about the team, right?

Tim: Exactly. I make sure the team has all the input they need. I’ll walk next door and ask people at all levels of the organization for their input. Everyone has valuable insights. We don’t have “know-it-alls” here, and that’s something we really value.

Kory: Is there anything new you want to learn outside of work?

Tim: I’d like to improve my iron game. I seem to have forgotten how to hit that club properly, so I’m planning to work on it in the next few months. I’m heading to Florida soon to focus on that.

Kory: And I know you like to travel in your downtime. Where do you like to go?

Tim: Wherever I can! We’re going out to see the Badgers play USC, and we’ve got a fun house in Malibu right over the Pacific Ocean. It’s going to be amazing. We just got back from hiking in Bend, Oregon. I try to do whatever I can. Last summer, we hiked in the Italian Dolomites, where the 2026 Winter Olympics will be held. It’s a beautiful area. I believe in collecting experiences, so I’m always trying to explore new places. There’s some fun stuff coming up.

Kory: Thanks for sharing. So, moving back to TKO Miller, what’s next for growth? Where do you see things going in the next one to three years?

Tim: We’re focusing on bringing in younger people and giving them more ownership. We’ve been doing this for a while, gradually getting them to take on more responsibility and think like owners. I let them handle reviews, make decisions about bonuses, and get involved as much as they can. They always ask for help when needed, but the goal is to keep involving them in the business. I’m still very active in business generation. A lot of my peers are selling their businesses, but I’ve been their trusted advisor for 20 or 30 years. I think they still rely on me to help them with the sale, which is encouraging.

Kory: On the flip side, what do you think will be the biggest challenge in the next few years?

Tim: The challenge is finding a few more people at the mid-level, especially someone with 10 to 12 years of experience. We’re strong in that range with a few people already, but finding another person at that level would be a big step for us.

Kory: Before we wrap up, what advice would you give to business owners trying to do everything on their own?

Tim: I just had this conversation with a friend who’s trying to do it all. The key advice is: if you’ve hired talented people, let them do their thing. They won’t do it your way, and that’s okay. You can give them guidance, but don’t try to turn them into you. When they try to be you, it comes across as inauthentic. Let them be themselves. For example, we’ve lost a few pitches that I felt we should have won, and my ego took a hit. But it’s a learning experience for them, and they’ll win next time. You’ve got to let them lose some to win in the future. I can’t be at every pitch, so they need to step up. I have to let go a bit, but it’s tough. They’ll be successful in the end.

Kory: That’s great advice. Now, as we close, you’ve had an incredible journey, and the impact you’re having on family and founder-owned businesses is impressive. Do you want to give a shout-out to anyone who’s helped you along the way?

Tim: First, of course, is my wife. We just celebrated our 35th anniversary yesterday.

Kory: Congratulations!

Tim: You know, it’s pretty cool to think about anyone spending 35 years—let alone 35 minutes—with me! My partner, Tammie Miller, and Joe Froehlich have been great, and everyone in this office—they’re all superstars. So, thank you to all of them.

One thing I tell anyone who’s listening, or anyone I talk to, is this: there’s just too much anxiety out there today. Looking back, whenever I felt anxious—like in school, when you heard about some of my grades—I realized, it’s going to be okay. People tend to “die too many deaths,” as they say. It’s going to be okay—just relax.

I tell the guys here every day, when they come in saying, “This deal… this deal…” that every deal feels like that. Just relax. And later, they look back and say, “Yeah, it turned out fine.” I remind them that even if we lose a deal, it’s not the end of the world. We’re not going under. Just relax.

Kory: The sun will come out tomorrow.

Tim: Not only that, it’ll be bright and sunny. You’ll get a bonus, and everything will be fine. But it’s important to remember that life’s too short to stress. Easier said than done, but I try to remind everyone to relax and enjoy because you only get one shot here.

Kory: Great message. Thanks for sharing that. So, how can someone learn more about TKO Miller? When should they reach out if they’re thinking of selling?

Tim: You can always visit our website. I encourage people to reach out even if they’re not thinking about selling. We’re very educational. If you want to know what your business is worth, we don’t charge for that. We’re not here to pressure you to sell. If you’re curious, just call or email me. I’m happy to talk about your business, and if it’s too small, I’ll direct you to the right place. I’m not going to charge you for giving you an idea of your business’s value. My contact info is on the website, and you can text or call me anytime. 

Don’t wait until you’re ready to sell. The biggest mistake people often make is thinking they’ll sell their business when they turn 62. The market might tell you when it’s time, not you. If you think you’re close, talk to someone who can give you honest answers. The person might say, “not yet,” or “let’s go,” but find someone you trust in my space who will give you honest advice. 

Don’t wait until everything falls apart. Do some preparation ahead of time. No question is a dumb question, and we have a lot of resources available. Just reach out, and I’ll be happy to help.

Kory: Thanks again for sharing your experiences and advice. We’ll get this out there, and hopefully, people who want to learn more about selling their business will reach out to you.

Tim: I appreciate you taking the time to speak with me today.

Kory: Thanks, Tim.

Tim: You bet. Thanks.