🎥 Entrepreneurship Failure: How to Survive the Darkest Moments in Business | Michael Ritsema

email [email protected] with "Podcast freebie" to book a coveted FREE guest spot on the show. To book a PREMIUM spot on the Podcast: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.drchrisloomdphd.com/_paylink/AZpgR_7f⁠⁠⁠⁠⁠⁠⁠⁠⁠Book a 1-on-1 coaching call: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.drchrisloomdphd.com/booking-calendar/introductory-session⁠⁠⁠⁠⁠⁠⁠⁠⁠ Subscribe to our email list: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://financial-freedom-podcast-with-dr-loo.kit.com/⁠⁠⁠⁠⁠⁠⁠⁠⁠📄 Entrepreneurship failure is one of the biggest obstacles standing between entrepreneurs and financial freedom. In this episode of the Financial Freedom Podcast, entrepreneur Michael Ritsema shares the brutal realities of business, including the failures, risks, and mindset required to keep going when everything feels like it’s falling apart. On social media we often see the highlight reels of success—funding announcements, billion-dollar exits, and overnight success stories. But behind nearly every successful entrepreneur are moments of doubt, financial stress, and painful lessons learned through failure. Michael Ritsema shares his personal journey through the ups and downs of entrepreneurship, including real estate mistakes, near bankruptcy during the dot-com collapse, and the mindset that helped him keep pushing forward when most people would have quit. If you’re searching for answers about entrepreneurship failure, risk-taking, and how to keep going during difficult business seasons, this conversation explores the lessons entrepreneurs need to navigate uncertainty and continue building toward financial freedom. You’ll also learn about:• Why bold risk-taking often determines where people end up in life• The truth about entrepreneur mindset and why successful founders embrace challenges• How to stay motivated during business failure and financial stress• Why many startup founders quit too early• How AI in entrepreneurship and automation are shaping the future of business• The opportunities still available for young entrepreneurs in today’s economyWhether you’re launching a startup, building a business, or simply trying to understand the realities of entrepreneurship, Michael’s insights offer practical wisdom for navigating failure, risk, and opportunity in the modern economy. This episode explores the mindset shifts necessary to overcome setbacks and continue moving toward financial independence and long-term success.⏱️ Timestamps (17:21 Video)00:00 – Podcast Intro00:28 – Guest Introduction: Michael Ritsema01:10 – The Dark Side of Entrepreneurship Nobody Talks About02:05 – A Costly Real Estate Mistake and Entrepreneurial Lessons03:10 – Nearly Going Bankrupt During the Dot-Com Collapse04:10 – When Should Entrepreneurs Quit vs Keep Going?05:10 – Warren Buffett, Failure & Investment Reality06:05 – What Drives Entrepreneurs to Take Risks07:30 – How Successful Entrepreneurs Learn from Failure08:30 – Advice for Young Entrepreneurs in Today’s Economy10:00 – Celebrating Wins vs Chasing the Next Challenge11:05 – How AI & Automation Will Change Business12:45 – Should Entrepreneurs Fear the Economy?14:00 – Local Economy vs Media Narratives15:10 – Key Lessons from Entrepreneurship Failure16:20 – How to Connect with Michael Ritsema17:21 – Podcast Outro🏷️ Hashtags#EntrepreneurshipFailure#EntrepreneurMindset#StartupFailure#FinancialFreedomPodcast#MichaelRitsema#EntrepreneurMotivation#BusinessLessons#StartupAdvice#FounderMindsetThank you to all of our sponsors and advertisers that help support the show! Financial Freedom for Physicians, Copyright 2026

• 0:00Speaker 00

  Your sausage McMuffin with egg didn't change, your receipt did. The sausage McMuffin with egg extra value meal includes a hash brown and a small coffee for just $5. Only at McDonald's for a limited time.

• 0:12Speaker 01

  Price and participation may vary. Promotion pricing may be lower than meal pricing.

• 0:16Speaker 02

  This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required. Compatibility and availability varies 18 plus.

• 0:43Speaker 03

  Born from the intensity of a night in the Eternal City. Introducing Born in Roma Fragrances by Valentino. Feminine perfume Donna Born in Roma features juicy black currant, central jasmine, soft cashmerin and warm vanilla. Masculine leaning but unisex Womo has notes of fresh violet leaf, aromatic sage, green vetiver and mineral salt. Shop holiday gifts at Macy's.com.

• 1:14Speaker 04

  Cashmere, outerwear and boots are up to 60% off at Nordstrom Rack. Save on brands like Ugg, Vince and Kohan. Join the naughty club for free to unlock exclusive discounts. Great brands, great prices. That's why you rack.

• 1:30Speaker 05

  They're running a Cover 2 defense. But you're running to get game day deals on Uber Eats. Keep everyone at tonight's watch party fed with deals from your go-to restaurants. Or stock up with deals on your favorite snacks and groceries. Whatever the occasion, get game day deals on Uber Eats all season long. It's not football without food. Uber Eats. Order now. Terms apply. Product availability varies by region. See app for details.

• 2:02Speaker 06

  In this episode, most people see entrepreneurial success. They don't see the mortgage mistakes. They don't see the near bankruptcy. They don't see the depression after nine eleven. In this episode, we're not just telling stories. We're extracting frameworks because stories inspire. You'll hear how one bad real estate deal became entrepreneur legal survival checklist. Protect the downside before chasing the upside. Guest of the show, Mike Ritsema. How he almost lost everything and became the risk framework. Responsibility increases before income does. Uncertainty is unavoidable. Stress is the tuition. Knowledge comes after action.

• 2:44Speaker 06

  You'll learn the mental resilient stack entrepreneurs use to survive dark seasons. Daily learning, physical challenge, set a goal, celebrate briefly, reset. We break down the five types of risk, career, financial, reputation, comfort, opportunity cost, and why avoiding risk is often the biggest risk of all. We turn economics into a playbook, control what's within. And for young builders out there listening, we lay out a 10 year compounding strategy because entrepreneurship isn't height, it's structure. By the end, you'll be able to answer one powerful question. Are you built for this? Now let's get to the episode.

• 3:26Speaker 06

  Hey guys and welcome to another episode of the Financial Freedom Podcast. I'm delighted about today's guest, Mike Ritsema from Michigan. An entrepreneur has gone through the ups, downs of business. Here to talk to us about these dramatic stories, learning, especially today's time and age. How do you keep going? How do you fight through it? He's been through it and here to pass on words of wisdom. Mike, welcome.

• 3:52Speaker 05

  Chris, thank you. Glad to be here. Let's tell some stories of ups and downs in entrepreneurship.

• 3:58Speaker 06

  Briefly introduce yourself and we'll dive into the questions.

• 4:02Speaker 05

  Mike Ritsema here in Grand Rapids, Michigan with I3 Business Solutions. I'm a sales type who certainly understand that I'm an entrepreneur. That goes all the way back to shoveling snow a number of decades ago. Secondly, rental properties.

• 4:19Speaker 04

  I've worked two jobs most of my life. I came home at night, went and worked on my rental properties. The ups and downs of that. Eventually bought a technology company. Entrepreneurs were built for risk. Give me a risk, I need to take a run at it. That's what I believe about entrepreneurship.

• 4:37Speaker 06

  We were talking in the green room about on LinkedIn or Twitter and Instagram. You see all these success stories. They're raised, series A, IPO. We actually never hear about people's darkest moments or people's failures. I want this episode to highlight that we have this unrealistic expectation that Elon Musk and the billionaires, they've never struggled. Talk about the dramatic stories of downs.

• 5:06Speaker 04

  Entrepreneurship is that story. The journey of life is that story. I was buying rental properties. I bought one in not the best part of town. It was a four family. I got it really cheap. It needed a ton of work. An individual came up to me and said, hey, I heard you bought a rental property. Do you want a private mortgage? I'm like, that's cool. I have no idea where I'm getting the money to finance this thing. Put a private mortgage on it. And a few years later, I sold it. Would you let them assume the mortgage? Yeah, no problem. They assumed the mortgage. Like, cool. I made money. I'm out of this thing. Till I got a call and was sitting in one of the most expensive attorney's office in Grand Rapids because they had stopped paying a mortgage.

• 5:51Speaker 04

  And I learned a lesson that you need a release of mortgage, which I did not sign. I did not know about. But now I'm sitting there on the hook for a pile of money that was not paid because I didn't have the legal document. I didn't, you know, hire a lawyer. That's the journey of life. Entrepreneurs, we give it go. We make mistakes. We learn. It is a journey of life. We think we can go to college, have all the answers, build a business plan. It's perfect. No, we take blows. I'm reading Peter Thiel's book right now. About the Y-Take 2K bust. I had a good run through the nineties in technology in 2001, bought a company.

• 6:35Speaker 04

  Didn't fully understand that the internet was burning to the ground at that time. I went oh for nine months selling. I had mortgaged my house, put a home equity on the loan on the house, had a line of credit at the business. I was 100% into all of them. Had not taken a paycheck in three months. I was on the edge bankruptcy. That is entrepreneurship. I was mentally depressed in the summer of 2001. Right on the edge. What happened on September 11, 2001, Chris? Yeah, the twin towers were hit. I was driving down 44th Street in Grand Rapids, Michigan, pulled into my mom's house, sat on the couch with her and thought, it's over.

• 7:20Speaker 04

  I'm bankrupt. The whole economy is collapsing. It is over. That is the journey of entrepreneurship.

• 7:28Speaker 06

  How do you determine when to stop and go when everything is against you?

• 7:34Speaker 04

  I don't know. We're all different. I understand myself. That summer, when things were going really bad, I said to my wife, if I would have stayed at the company I was at, two or three salespeople left. I would have been the only one standing. Success would have been handed to me. She said, and you wouldn't have been happy. She's right. She understood me. I am built for the challenge. I'm built for risk. I don't care if it's ping pong. I don't care if it's golf, running, biking, or business. Somebody give me a risk. Now, that's the way I'm built. So, how do you know when it's time to say, okay, time to shut this one down and move on to the next one? I can't answer that question.

• 8:17Speaker 04

  I do know that the perseverance to keep swinging and pursuing is the answer for a lot of entrepreneurs, including Elon Musk. Read his book. That boy with Tesla was flat on his back, scraping for money to hold this thing together. No, it's never easy. I think we see the social media posts. It's all wonderful. No, read the books. It is.

• 8:45Speaker 00

  Your sausage McMuffin with egg didn't change, your receipt did. The sausage McMuffin with egg extra value meal includes a hash brown and a small coffee for just $5. Only at McDonald's for a limited time.

• 8:58Speaker 01

  Price and participation may vary. Promotion pricing may be lower than meal pricing.

• 9:02Speaker 02

  This episode is brought to you by Google Chrome. You think you know a browser, but Gemini and Chrome, that's new. It can help you with practically anything on the web, like restoring a vintage motorcycle from a 50-page restoration block, or finally break down that long article you've had open for weeks. Gemini and Chrome is here for it. Ready to make anything online make sense? There's no place like Chrome. Check responses set up required. Compatibility and availability varies 18 plus.

• 9:28Speaker 03

  Born from the intensity of a night in the Eternal City. Introducing Born in Roma Fragrances by Valentino. Feminine perfume Donna Born in Roma features juicy black currant, central jasmine, soft cashmerin, and warm vanilla. Masculine leaning but unisex Womo has notes of fresh violet leaf, aromatic sage, green vetiver, and mineral salt. Shop holiday gifts at Macy's.com.

• 9:59Speaker 07

  Stay cozy and look cool with up to 60% off cold weather gear at Nordstrom Rack. Save on cashmere, outerwear, boots, and more from brands like Ugg, Vince, Kohan, and Hunter. Join the Nordy Club for free to unlock exclusive discounts. Shop clearance and new arrivals first, and more. Plus, buy online and pick up at your favorite Rack store for free. Great brands, great prices. That's why you Rack.

• 10:25Speaker 05

  They're running a Cover 2 defense. But you're running to get game day deals on Uber Eats. Keep everyone at tonight's watch party fed with deals from your go-to restaurants. Or stock up with deals on your favorite snacks and groceries. Whatever the occasion, get game day deals on Uber Eats all season long. It's not football without food. Uber Eats, order now. Terms apply. Product availability varies by region. See app for details.

• 10:57Speaker 06

  A colleague of mine, we're reminiscing about some of the world's Warren Buffett. For example, you assume he's the world's richest investor. He's actually had a bad investments. So put that into perspective.

• 11:11Speaker 04

  Furthermore, Chris, I'm getting a little bit older and I love this stuff. If I retired, I'd be bored to tears. What do I do? I need another challenge. But look at somebody like Warren Buffett. Look at Bill Gates. Look at these people that can retire. They're still in the game. They enjoy it. They took the risk. They've done well, but they're still working. Why? Because they enjoy it.

• 11:37Speaker 06

  Next question is, what do you think drives an entrepreneur? What motivates you?

• 11:42Speaker 04

  I think that's different for everybody, but definitely for me. Number one, I believe that the single biggest trait that defines one's station in life, where you end up and where you're going is risk. That willingness to take a risk. I don't care if you're working on a factory production floor. When you get the opportunity to be a manager, that's a risk. You have more responsibility. Some say, I don't want that risk. That's okay. No matter what profession you're in, that willingness to take a risk defines one's station in life. Definitely for entrepreneurs, the willingness to take a risk.

• 12:26Speaker 04

  For me, the challenge is what gets me up in the morning. Others, it might be social status, doing good for the world. It might be a lot of different things, but for me, it is the challenge, the risk. Recently, two years ago, I bought a company and I got to a point in my life. I'm like, you don't need more risk. Six months later, I'm like, you need more risk. For me, it is risk and the challenge. For others, it could be something different.

• 12:56Speaker 06

  Quick pause here. If this episode is making you rethink how your income is structured, that's intentional. Information doesn't create freedom. Structure does. At the end of this episode, I'm going to show you how to diagnose whether you're building leverage or just scaling complexity. Let's get back into it.

• 13:16Speaker 06

  Going back to those times when, for example, the pain of real estate, assuming that mortgage, what are the thoughts, emotions, or for example, people that are in the stock market, they lost a lot of money, they're down and out, how do you keep going in those times?

• 13:35Speaker 04

  I will tell you that I'm a prolific reader. I'm a slow reader, but I read every day. I like learning. That's a trait of people that move forward in life. They enjoy learning a PhD, certifications, college degree, not so much. I have a tech company here and some of the smartest people I have here, no college whatsoever, if I asked them to get a cert test, they'd say, I'm quitting, I'm out of here. Brilliant minds don't always require a degree, but the willingness to learn, great entrepreneurs, business people, people that make it, they learn from their mistakes. If we can embrace that in the real estate transaction.

• 14:18Speaker 04

  You think I spent the rest of my life asking if we need a release for this document? Yes, I did. So we learn through these mistakes and that's how we reach higher. That's the journey of life.

• 14:32Speaker 06

  When you ask the younger generation, their vision of the future, a lot of them say, things are very bleak. People hate their jobs, AI is gonna take all their jobs and business entrepreneurship is harder than ever. What's your number one advice to a young person or startup entrepreneur?

• 14:51Speaker 04

  My father was a blue collar worker and wanted me to do exactly what he did. I chose to take a risk. I bumped into some people, young people, never seen anything like this. They said, you've had the opportunity, you're older, there's not much opportunity left in America. I said, talk to me in 50 years. Talk to me in 50 years after you've worked two jobs for much of your life, maybe six, seven days a week, keeping an eye on, working hard, investing, running a business, whatever it is, talk to me in 50 years. There's opportunity in America. Some are saying, Peter Thiel, a book I'm reading,

• 15:32Speaker 04

  the ability to innovate today with AI and the technology, the ideas that are popping up, the billionaires that are made, the opportunity is vast. I would say to young people that say, there's no opportunity in America. Yes, that's true for you. You choose to create opportunity and find that opportunity.

• 15:56Speaker 06

  We talked about using emotional mindset techniques.

• 16:01Speaker 06

  What is the highest point or peak of your entrepreneurial journey? How did it feel once you got out of those slumps?

• 16:09Speaker 04

  We're all different and I'm a goal person. I'm a guy built for a goal. When we hit a plateau, I say this to my children. I say this to the company, we will celebrate. Then guess what's going to happen? I'm setting a new goal. We are going there. I realize I have to work on the journey and others enjoy the journey and really need to work on setting a goal. So when I reach that pinnacle, when I reach that point, I'm celebrating. The problem with my personality is I'm bored. We need a new challenge. What happened two years ago is the company was going great. I'm getting a little older, like time to relax. Warren Buffett, 90 years old, he handed the company over. Why didn't he do that 25, 30 years ago? He loves it.

• 16:55Speaker 04

  I'm built for that. When I hit that point of, okay, time to relax. No, let's go. Let's reach for another challenge. We're all different in that way. I understand that's me. I'm going to celebrate for a day or two and then I'm going, I'm pushing.

• 17:12Speaker 06

  In this day and age, knowing that we have artificial intelligence as a tool.

• 17:19Speaker 06

  If you were to restart, build from scratch, how would you rebuild?

• 17:25Speaker 04

  At I3, we are a technology company and our theme this year is automation. 65% of the world does not like change. In small business, what you try to do is create repeatable processes. We build that repeatable process and people do it. Thank you. I love you for doing it. And then we say, change, we need to automate this. AI is nothing more than automation. What would I do differently? I would invest in the software earlier to automate and improve the process of the business. Every business goes from people excellence to process excellence. We hire smart people, say, do good stuff.

• 18:09Speaker 04

  And then we're like, you made a mistake. You made a second mistake. Time to automate, put a workflow in, put software in. I would invest in software, automation, workflow type tools to build processes. That's what I would do differently. Invest in software that aids in process and oftentimes looks like automation, which AI is going to continue to improve.

• 18:37Speaker 06

  The month of February was a month of chaos. As an entrepreneur, how do you see the future of the economy, given all of the negative headlines that we're seeing today?

• 18:50Speaker 04

  I've been attending the Economic Club here in Grand Rapids for decades. It is true that all economics are local. We look at the national economy, the world drama. Forget all that crap. Run your business right where you are in the economy that you have right here. Jobs report's down, the world's ending, isn't it? Look around you. How many people have been laid off right into your community? Are you still working? I'm unfazed by that. And some would say oblivious because I missed the great recession of 2007, 2008. I didn't know what was happening until it got to 08, 09. Then it's what is going on?

• 19:33Speaker 04

  Economics and finance are local. Live in your local community. Don't listen and read that stuff. Run your business, run your life, live your life right where you are.

• 19:46Speaker 06

  Wow, I love that. Powerful. How can people connect with you and reach out to you?

• 19:50Speaker 04

  I3 Business Solutions in Grand Rapids, Michigan. We are a technology services company. We either become the IT department, the help desk, and cybersecurity, or we assist the technology department. It's I3BusinessSolutions.com, the letter I, the number 3, Business Solutions, or I3B U S dot com.

• 20:16Speaker 06

  Thanks so much. Really appreciate you coming on and sharing your knowledge and expertise. Keep up the great work.

• 20:22Speaker 04

  Thank you, Chris.

• 20:26Speaker 06

  Let's zoom out. If you're a physician, founder, or high-income professional, and you feel like you're working harder every year but not structurally freer, you're not alone. The mistake is an effort. It's architecture. This show exists to help you convert expertise into scalable leverage faster and with fewer expensive missteps. Here's the diagnostic I mentioned before. If your income requires your constant presence, if your capital isn't compounding outside your profession, if your highest value talent is doing low-value tasks, you don't have a growth problem. You have a leverage design problem. And if you want to fix it with clarity instead of guesswork, I offer a limited number of one-on-one leverage strategy sessions each month.

• 21:11Speaker 06

  We audit your income model, capital deployment, authority positioning, and structural bottlenecks, and design your highest-return rule. If you're serious about compressing years into months, the link to apply is below.

• 21:31Speaker 00

  Your sausage McMuffin with egg didn't change. Your receipt did. The sausage McMuffin with egg extra value meal includes a hash brown and a small coffee for just $5. Only at McDonald's for a limited time.

• 21:43Speaker 01

  Price and participation may vary. Promotion pricing may be lower than meal pricing.

• 21:46Speaker 05

  They're running a cover-two defense. But you're running to get game day deals on Uber Eats. Keep everyone at tonight's watch party fed with deals from your go-to restaurants. Or stock up with deals on your favorite snacks and groceries. Whatever the occasion, get game day deals on Uber Eats all season long. It's not football without food. Uber Eats. Order now. Terms apply. Product availability varies by region. See app for details.

• 22:17Speaker 02

  This episode is brought to you by State Farm. Football has a play for just about everything. You can go deep, keep it on the ground, or draw up something nobody sees coming. And whether you want to run a flea flicker or the tush push, you need a plan to fit your unique situation. That's why State Farm takes the time to get to know you so they can help personalize coverage for your life and budget. Now that's a solid game plan. Like a good neighbor, State Farm is there.

• 22:45Speaker 07

  When everything feels nonstop, movement becomes the pause. So give Lululemon this holiday season. Smooth, seamless running gear builds momentum through every mile.

• 22:57Speaker 07

  Targeted support adds steadiness to every pulse and hold.

• 23:03Speaker 07

  And dynamic stretch expands presence through every pose.

• 23:09Speaker 07

  Give the feeling. Shop in-store and on lululemon.com.

• 23:15Speaker 05

  Sam's Club is the club for every holiday club. Guess who's joining the club this season? Walmart Plus. Yep, Sam's Club Plus membership now comes with Walmart Plus at no extra cost. Two memberships, one great price. Just $120 a year can save you time and over $700. Want to get in on the membership duo of the century? Visit sam'sclub.com. Come join us. Sam's Club.