Tell us the story of how you got started. Take a moment to transport yourself back in time:
Having just left a busy business I’d been part of for 15 years—a place where phones never stopped ringing, and coworkers gathered around the water cooler sharing weekend stories—I suddenly found myself alone. It was the first day of my own entrepreneurial journey, over two and a half decades ago. No clients, no idea how to prospect or make a sale, no ringing phones, no water cooler chatter—just silence and uncertainty. I remember thinking, What have I done? Where do I go from here? By lunch, self-doubt had already settled in, making me question everything.
Then, unexpectedly, there was a knock at the office door. For a moment, it felt like I was back at my old job, surrounded by the familiar hustle and bustle. I opened the door, and there stood a delivery person with a large office plant. Surprised, I read the card: “We love you and hope nothing but success for you.” It was from two dear friends. Wow, I thought. Someone cares.
That small gesture—just a plant and a note—changed everything. In that instant, the self-doubt lifted, and a new determination took its place. I picked up the phone and began reaching out, ready to prospect and build. Looking back, I often wonder where I’d be today without that moment. Would I still be working for someone else? That simple gesture gave me the confidence I needed to keep moving forward.
What was your inspiration?
I believe that knowing your core values—your non-negotiables—is essential for paving your path forward. For me, those values are Faith, Family, and Freedom. After a difficult breakup, I found myself reflecting deeply on who I was and who I wanted to become. Growing up as an introvert with low self-esteem, partly due to a traumatic experience of being kidnapped at gunpoint by my biological father as a toddler, I had long struggled with self-worth.
But after the breakup, something shifted—a fire lit my soul. I decided to stop believing what everyone else thought of me and instead prove myself wrong. It wasn’t about anyone else’s expectations; it was about challenging my own doubts. So, I took a leap of faith and started my own business. In my family, there were no entrepreneurs—everyone was a college graduate, and I wasn’t. But I was tired of working for others, tired of living within the limitations I’d set for myself, and tired of the story I’d been telling myself about who I could be.
So, I made the jump, and I haven’t looked back several businesses later.
What did you do first? How did you make your idea real?
Like many, owning my own business was a pipe dream. I didn’t know where to start, but one day, I’d had enough. It was Thanksgiving week, and I was working for a small business with about 20 employees. Our production schedule was light, and the industry didn’t demand 24/7 operations, so I assumed we’d have the Friday after Thanksgiving off. But as we left on Wednesday, nothing was confirmed.
Finally, someone asked, and the owner said, “Yes, we’ll be open Friday at 8 a.m.” Everyone was frustrated, knowing the phones wouldn’t ring, no machines would run, and no clients would show up because they, too, were closed. Sure enough, Friday morning was as empty as expected, and by 9:15, the boss told everyone they could go home. Instead of feeling grateful, I was furious. Why bring us in for no reason, on a day meant for rest, just to send us back home?
That moment hit me hard. If I disliked the culture so much, why not create my own?
If I wanted control over my schedule and work environment, I realized I’d have to work for myself. That frustration turned into fuel, pushing me to make a plan, take action, and build something that aligned with my values.
Who did you seek out for help? How did you find the right people to work with?
This was the turning point where I went from being a business owner to a serial entrepreneur. My first business quickly grew from zero to just under seven figures, but after reaching that level, I got stuck. For five years, I couldn’t break through to the next stage. Realizing I needed more bandwidth, I decided to seek out business partners. I reached out to a few people in my industry, and we agreed to combine our strengths to expand operations.
While we successfully built a business that could run without us, I also started other ventures along the way. However, cultural and core value differences eventually strained the founding partnership, leading us to hire a business coach. The coaching helped temporarily, but the partnership had already eroded beyond repair. Eventually, the partners split, leaving me and one other partner to handle the fallout—which ultimately led to both business and personal bankruptcy.
In the midst of this journey, my original business coach encouraged me to explore coaching as a career. He noted my marketing and advertising background, my experience as a business owner, and my strong empathy—a key trait in DISC behavioral assessments. So, after closing the chapter on past ventures and recovering from bankruptcy, I set out to help other small business owners through the same quality coaching I’d benefited from myself.
Tell us the story of your first big break. How did you get your first customer, sale or partnership?
After closing the chapters on past ventures, I began business coaching for small business owners. However, I quickly realized that my impact wasn’t as big as I wanted it to be, and I was still trading time for money, which wasn’t scalable. So, I thought bigger and founded BOSS—Business Ownership Simplified for Success. While BOSS includes business coaching, that’s just one piece of the puzzle. The core concept of BOSS is to provide everything a business owner needs to succeed, following the same milestones that helped me scale a multi-million dollar business.
The first thing that moved the needle for me was coaching. With a solid strategy from my business coach, I realized I needed funding to grow. It took over two years to find a bank willing to lend me $50,000—just 20% of what I actually needed. So, one of the first products we introduced at BOSS was business loans. Our loans can be approved within 24-48 hours, and many are funded by the end of the week, removing a major barrier for entrepreneurs.
The next challenge I faced was attracting and retaining employees, so we added health insurance, then commercial insurance, and the list has only grown from there. Today, BOSS is a one-stop shop of products and services for small business success, continually expanding with each successful launch.
One key lesson I’ve learned is that too many business owners waste valuable time searching for solutions they’re not familiar with, uncertain if they’re even getting a good deal. At BOSS, we eliminate that hassle by simplifying the process, providing business owners with strategic products, services, and support. Ultimately, we help them build a business that can run without them.
So, how did we make our first sale? It was straightforward—we provide real solutions to our clients’ problems.
Bio:
Michael D. Morrison, Founder & CEO of BOSS, born-raised-resides in Oklahoma City, husband, and father. Before becoming a business coach, I spent years in marketing and advertising, specializing in database and client list management. That experience taught me the ins and outs of business growth and client relationships—lessons I now share through BOSS.
My values—faith, family, and freedom—shape both my life and work. I founded BOSS (Business Ownership Simplified for Success) to help small business owners build companies that can run without them being there 24/7. I know the struggle of feeling tied down by your business, and I’m passionate about helping others break free and find success through process-driven strategies.
Outside of work, you’ll usually find me outdoors with my family, whether we’re running, biking, or hiking. My mission? To empower business owners to build something lasting, to believe in “I am possible,” and to own a business that works for them—not the other way around.
