I’m a Self-Made Millionaire With 3 Failed Startups: What I Learned the Hard Way
Written by
Kathryn Jackson
Edited by
Amen Oyiboke
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Self-made millionaire Shawn Brady spent years navigating the highs and lows of building businesses. He was just 15 years-old when he started his first business — a real estate sign company. He worked in the real estate industry selling a wide variety of properties including residential, development and investment. From real estate to bad investments, Brady had three failed startups.
Between 2009 and 2010 Brady had a serious change in his life after his second divorce. Finding himself in a position of having to start over with very little to his name, he decided to obtain a CDL at trucking school. In 2014, he co-founded a company called MIT45 — a major player in the kratom industry, now valued at nearly $300 million.
Today, self-made millionaire Brady is focused on his financial coaching business, which helps individuals achieve financial wellness and personal growth.
Here’s more about how he overcame three business failures and the hard lessons he learned on his climb to success.
Discipline Is More Important Than Motivation
“Early in my career, I built some businesses based on passion and excitement, thinking that was enough to sustain success. I learned the hard way that motivation is fleeting, but discipline in daily operations is what keeps things moving forward, especially during the tough times,” said Brady.
Clarity in Your Offering Is Non-Negotiable
Brady shared that he once launched a business that tried to serve too many audiences without a clear value proposition. He said he learned that without laser focus on who you are serving and what problem you solve, it’s easy to waste resources and confuse your customers — and yourself.
Your Personal Growth Matters as Much as Business Growth
According to Brady, one of the hardest lessons he learned came from realizing that unresolved personal issues can derail even the best business ideas. He believes financial success without personal alignment will leave you unfulfilled, and if you don’t work on yourself, your business will always feel incomplete.
“I’ve also become relentless about defining what success looks like upfront — whether it’s scaling revenue or creating impact,” he explained. “Finally, I’ve learned to balance ambition with self-awareness, making sure that I’m as focused on personal growth as I am on business results.”
Brady’s Advice for Aspiring Entrepreneurs
Brady offered the following pieces of advice for people who are starting up businesses.
Don’t Skip the Foundation
Brady explained that you need tomake sure you have the right systems, structures and routines in place before scaling. “It’s tempting to sprint at the beginning, but success is a marathon, not a sprint,” he said. “Get the basics right before you start chasing bigger goals.”
Test and Iterate Constantly
“Be willing to fail fast and pivot quickly,” he said. “The market will give you feedback — listen to it. Don’t cling to ideas that don’t resonate just because they were part of your original plan.”
Work on Yourself as Much as Your Business
“Your business will only grow to the extent that you do. A business is a reflection of the founder’s energy, and if you’re not in a good place, your venture won’t be either,” Brady explained. He recommends focusing on personal alignment and emotional wellness — whether through meditation, therapy or mentorship.
Success Can Come From Failure
“Failure can often be the beginning of someone’s greatest success story,” said Brady. “Through my journey of two divorces, failed real estate developments, some significant investment mistakes, and a landscaping business early in my career that was not successful, I have learned that firsthand.”
All of these experiences transformed how Brady built and operates his businesses today. He said he no longer jumps into ventures out of excitement alone. Every business decision he makes now comes with a clear plan, realistic timelines and a focus on sustainability.
Famous writer Dale Carnegie once said, “Develop success from failures. Discouragement and failure are two of the surest stepping stones to success.” This holds true for many entrepreneurs — through perseverance despite their failures, they climb the rocky road to success.
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