Reid Tileston

Reid trains the future entrepreneurial business owners of America. As an Adjunct Professor at Case Western Reserve University he teaches Entrepreneurship Through Acquisition, invests in entrepreneurial business owners, is a board member, and is an award winning paid keynote speaker. Reid co-created the curriculum for the Entrepreneurship Through Acquisition course at the University of Chicago Booth School of Business, lectures at leading academic institutions  such as Dartmouth, the University of Chicago, the University of California, and BYU and serves on the University of Chicago Entrepreneurship Through Acquisition Advisory Committee. His expertise is derived from 16 years of successful, on the ground entrepreneurial business ownership experience; acquiring, opening, growing and selling 4 companies in addition to his academic research. Reid achieved a return multiple of invested capital (MOIC) of over 10x on his most recent acquisition and was a top performing Anytime Fitness franchisee. Reid has been featured in publications including The Wall Street Journal and Crain’s Chicago. Reid is a graduate of the University of California at Berkeley (BA, Economics) 06’; the University of Chicago (Booth) School of Business (MBA, General Management, Entrepreneurship) 15’ and is a Doctoral Researcher  at Case Western (26’) doing a PHD dissertation on Entrepreneurship Through Acquisition where he presents his research at academic conferences. As an Eagle Scout, Ironman 140.6 distance triathlete, winning endurance athlete, and a graduate of the National Outdoors Leadership School (NOLS), Reid rejuvenates in the outdoors and is in a perpetual state of planning his next life adventure which recently entailed racing up the world's tallest staircase in Switzerland in addition an around the world trip. Reid is well positioned to help business owners in waiting experience the autonomy of entrepreneurial business ownership.

As an Entrepreneurial Business Owner (EBO), discipline is everything. But when you’re your own boss, how do you stay accountable? The answer is simple: the power of peer groups. Surround yourself with people who inspire you to level up. Your peer group directly impacts your discipline, success, and growth. Be intentional about who’s in your circle. If you want to be more effective, surround yourself with those who are focused, driven, and gritty. Remember, iron sharpens iron!

Life is all about serving others! That’s why I chose to join The Church of Jesus Christ of Latter-day Saints. The Church is built on the principle of service—it’s not about me, it’s about how I can make a difference for others. Whether you join the same church or another organization that values service, one thing is certain: true happiness and fulfillment come from lifting others up. Service is at the heart of a meaningful life!

People often ask me how I managed to write “Grit It Done” 📒🔗 in just one year. The key? Surrounding myself with mission-driven messengers, like the inspiring community at @brandbuildrsgrp. These folks were in the trenches with me—writing, learning, and pushing through challenges together. Being a part of a peer group that shares your passion and purpose changes the game. Writing a book doesn’t have to be lonely or stressful. You can choose to struggle solo, or you can find an empowering group like BBG and grit it done together. Your entrepreneurial journey shouldn’t feel like a solo mission. Like finding the right business partner, the right peer group will give you energy, drive, and, most importantly, accountability. Don’t settle for less than greatness—you’ll know when you’ve found your people.

“Leave it better than you found it.” This is the ethos of an Entrepreneurial Business Owner. When I bought an industrial services business, everything was still being scheduled out of a red book, written in pencil. Taking it from that red book to the cloud transformed our operations. We boosted profitability, improved efficiency, and—most importantly—enhanced the lives of our entire team. As you look at your next opportunity, ask yourself: What’s your red book? How will you leave it better than you found it?

The University of Chicago Booth School of Business holds a special place in my heart. While there, I had the honor of being the teaching assistant for Booth’s very first class on Entrepreneurship Through Acquisition. Working alongside two incredible adjuncts, we built the curriculum from the ground up, which laid the foundation for my next acquisition and a strong return on investment. Today, I’m thrilled to teach the same material that inspired me. Booth, thank you for the inspiration. The best is yet to come!

Not all revenue is created equal! The real key? Understanding three things: Is it cash-friendly? Is it recurring? Is it high margin? Businesses that hit all three criteria set you up for success and financial freedom. Remember, owning revenue streams that work for you is the path to true autonomy.

It’s easy for people to see you at the finish line. When you’ve conquered the world’s tallest staircase, finished an Ironman, or sold a business for millions, it looks like a quick success. But what people forget is the grit behind the scenes. I woke up at 4:45 AM every day, running up 77 flights of stairs in the morning and again at night. This wasn’t glamorous—it was doing the hard work when no one was watching, laying the groundwork for success when I didn’t feel like it. My advice? Go out there and do exactly what you don’t want to do. That’s where the real growth happens. #GritItDone

What gets measured gets done! Some say ignorance is bliss, but in business, ignorance is a luxury you can’t afford. To truly move the needle, you need to have your finger on the pulse of the numbers that matter. Identify the key metrics that drive value and growth for your business, and then relentlessly drill down on them. When you focus on what matters most, you’re not just tracking results—you’re steering your business towards success. Understand your metrics. Own your outcomes. Grit It Done.

People often ask me how I managed to enjoy doing tough, painful things. The answer? I surround myself with people who inspire me, and when the going gets tough, I choose to smile. That’s exactly what I did when I took on the world’s tallest staircase in Switzerland—every step was grueling, but I wore a grin the whole way. It’s not just about enduring the pain; it’s about embracing the journey and loving every second of the gunk. Elation always awaits those who “Grit It Done”!📒🔗

I spent six figures to learn this: your internal rate of return (IRR) must exceed 30%. A 30% IRR is the benchmark that serious investors aim for, and it’s the same standard you should apply as an Entrepreneurial Business Owner (EBO). Don’t settle for less! Understanding IRR might seem complex, but it’s essential for financial success. I’ve made the mistakes so you don’t have to. Click the link in my bio to access a free tool that simplifies this calculation. 💡

If reaching out to your network feels like a chore, you’re in the wrong circle. ❌🤷‍♂️ Surround yourself with people who elevate you—those who make you strive to be your best self. When you’re with the right people, you don’t need reminders to connect; it happens naturally because they add so much value to your life! With the right team, there’s no limit to what you can achieve. But beware of the bad apples—they can spoil the whole batch quickly. Cut them loose quickly because a leader’s job is to foster a positive culture, and that’s impossible if negativity is allowed to spread.

Hire slow and fire quickly! As an entrepreneurial business owner, your success often hinges on the team you build. While it’s easier said than done, cultivating and investing in entrepreneurial employees is key to driving your business forward. Remember, the culture you foster is a reflection of what you tolerate. Keeping unfit team members can push your best talent away. Protect your culture by being deliberate in your hiring and decisive in your firing. Your business deserves nothing less!👊

Can you explain what you do professionally to a six-year-old? 🤔 It’s crucial to keep things simple! Complexity doesn’t equate to value. Think of something as enduring and functional as a fork—simple, effective, and still relevant after thousands of years. Invest in what works. Prioritize clarity and efficiency in every transaction. The more straightforward the process, the more you’ll achieve—and the stronger our country will become. Keep it simple; Grit It Done.

What do Abraham Lincoln and I have in common? Probably not what you’re thinking! It’s the idea that failure is a building block of success! Lincoln faced countless setbacks in his life, yet he went on to become one of the most impactful leaders in the history of our great country!🇺🇸 As an entrepreneurial business owner, failure primes your future success. Don’t fear it—embrace it. Each failure sharpens your ability to “Grit It Done” 📒🔗 and come out stronger on the other side!

@RandBusiness Hit up @EntrepreneurOrg they have a robust chapter out there that I used to be a part of

Anyone have any good ideas on how I can get in front of more SMB owners in Chicago? I’d like to get ~50 people to our next event in September, but we’re currently at 17. Welcoming all ideas!

Are you sitting on a high margin cushion? That's your superpower! Mistakes won't sink you—they’re the stepping stones to your next big win as an EBO! Embrace the challenges, and let them fuel your journey to lasting success. Want to master the art of evaluating businesses and make smarter moves? 📈 Dive into my book “Grit It Done” for actionable strategies on how to own and operate your future. 📒🔗

True entrepreneurial business owners don’t just accept failure—they use it as fuel to power future success. My first fitness club wasn’t a huge success. It wasn’t even a great ROI. But I learned, adapted, and used those lessons to become a top performer in the Anytime Fitness ecosystem. Remember, setbacks are just setups for your next breakthrough. The question isn’t if you’ll fail—it’s how you’ll rise afterward. So, ask yourself: Do you accept failure, or do you strive for success?

The key to thriving as an entrepreneurial business owner is all about mindset. 🧠💪 You're either fully committed or you're holding yourself back. Half-hearted efforts won’t cut it—if you're not all in, you're just in the way. Challenges and hard work are part of the journey, but facing them head-on, with a smile and a readiness to get your hands dirty, leads to freedom, autonomy, and fulfillment. The rewards on the other side make it all worth it. Good things come to those who are all in!

What would Dancing Dan do?! Every time I'm tempted to hit snooze or skip the grind, I think of Dancing Dan—the legendary sign spinner in Sacramento. He shows up, rain or shine, ready to bring his A-game, every single day! When I need to "Grit It Done" 📒🔗, I channel that same unwavering commitment. Dan doesn’t just spin a sign; he spins motivation into every passerby’s day. His energy, regardless of the circumstances, reminds me that consistency and attitude are everything. It’s not about waiting for the right conditions; it’s about showing up with grit, every single day. Thank you, Dancing Dan, for being a beacon of dedication and for reminding me to level up my life!

Discipline is contagious! If you find yourself lacking it, look around – the people closest to you might be part of the reason. We inevitably mirror those we surround ourselves with. That’s why it's crucial to be thoughtful, strategic, and diligent about who you choose as your peers. Your group will define you! To be an effective entrepreneurial business owner, you need to align with the right peers. The right peer group doesn’t just support you – it empowers you to achieve greatness.