Navigating Entrepreneurial Challenges: A Guide on Turning Sh*t Moments to Success

These 3 words cost my company $1.3M and slashed $9M more off our revenue: “I RAISE YOU”. What happens when you’re in Vegas, coupled with a ton of drinks at the Playboy Club? DISASTER. Yes, that was me, thinking I was invincible and about to win a bet—and of course, life being funny that way threw me a curve ball—$1.3M worth, at that.

Back when this happened, it felt like the end of the world, and all I could blame was myself. In hindsight, I knew this was the kick in the butt I needed to get my sh*t sorted, and boy, it was a good, hard kick indeed.

In this edition of Dopamine Dose, I’m going to dive into the biggest mistakes most entrepreneurs make and how to avoid exactly what I did in the past—so you don’t end up getting sh*t faced drunk, betting $1.3M, and almost losing your company.

Mistake #1: Lack of Clear Vision

Finding your vision can be tough, but it’s your north star. I remember when I met Sir Richard Branson on Necker Island. It was a trip with my peer group, Maverick1000, an invite-only network of entrepreneurs. Our flight there was nerve-wracking—imagine a tiny plane with a door that wouldn’t close! But the real lesson came from watching Richard in action.

Richard’s approach to vision was eye-opening. We first met him on Mosquito Island, where he casually pitched his vision for the island’s future. His clarity and ability to see opportunities were incredible.

It wasn’t just about making money; it was about creating something bigger—a community.

Richard Branson & Joshua B. Lee

Richard Branson and I

This experience made me realize the power of having a clear vision. Before this, I was just going through the motions in my business. I was focused on daily operations and profits but lacked a clear direction. This is a common mistake many entrepreneurs make—not having a clear vision. Without it, you’re just spinning your wheels without a real sense of purpose or direction.

🔵 Start by understanding your pain and your “why.”

🔵 Journal your thoughts, answer key questions about your goals, and regularly revisit your answers. Key questions to get you started: What do you want to create in your life? When you visualize the future, what do you feel? What results will you achieve? How will you bring your vision to life?

Remember, a clear vision is the foundation of achieving fulfillment and leaving a legacy. It’s what separates merely running a business for profit from building something meaningful and impactful.

Mistake #2: Neglecting Personal Health and Well-being

Obesity and weight issues are prevalent in the United States, where almost 41.9% of U.S. adults are obese. Beyond vanity and looking good, it’s important to stay healthy because your physical health can relate to your mental health. Running a successful business means being able to take care of yourself AND the people who rely on you; the only way to do so is by being holistically healthy in mind and body.

Entrepreneurs often push their health aside, focusing solely on business. I learned this the hard way. I was conducting business as usual, but my health had plummeted, and I didn’t even realize how far I’d fallen. My energy was low, and I felt lazy. Back then, I believed I needed to support my family 100% no matter the cost, looking back, I regret not prioritizing my health and energy.

Joshua B. Lee & his son

First time Dad and stuck in the mindset that I needed to handle it all

Joshua B. Lee circa 2009

2009 and thinking I had it under control

I remember looking at old photos and wondering, “Why didn’t I maintain my health?” I had let my business drive my life, a trap many entrepreneurs fall into. It’s like running a car on one wheel—you need all four cylinders to move forward. The turning point came when I started taking Pilates classes. It slimmed me down and reignited my energy. I realized that staying physically active was one of the pieces of the success puzzle. Competing in races like Spartans and Tough Mudders fueled my competitive spirit and kept me healthy.

Today, I enjoy working out outdoors, using Peloton, or hitting the gym with my son Jayden. Remember, physical energy boosts creative energy, which is essential for any entrepreneur. Don’t make the mistake of neglecting your health. Balance your work with physical activities and set realistic fitness goals. Incorporate short, daily workouts to stay energized and productive.

💥 A healthy body supports a healthy business.

Joshua B. Lee & son

Happy, healthy and much smarter as a Dad of 3. Ava is 9 months old now, I want to be around for all 3 of my kids for a long time.

Mistake #3: Financial Mismanagement

I save this story for last, because I think, as shocking as it was—it was one of the most pivotal moments in my life that I’ll never forget. Once in Vegas, I bet $1.3 million on a business deal after some drinks. It looked like a sure win that would skyrocket my profits, but I hadn’t done my homework. That deal ended up nearly ruining my business, dropping our revenue from $10 million a year to just $1 million. The financial fallout was brutal, leading to sleepless nights and legal battles.

I had to decide whether to chase the $100,000 needed for legal fees or focus on rebuilding. Ultimately, I chose to rebuild, learning a hard lesson about the importance of due diligence and sound financial decisions. As I reflect on that experience, I realize it was a tipping point that led me to become more centered and successful in all aspects of life. To paraphrase Warren Buffett, mistakes are the best way to learn, especially when you learn from the mistakes of others.

Warren Buffett quote

Awesome quote from Warren Buffett

This experience taught me that, as entrepreneurs, no matter what, you’ve got to keep your finances in check, even if you’re at the height of your career and business. 82% of small businesses fail because of cash flow issues, every business decision has an impact on your finances. After all, cash is the bloodline of any business, and without it? You’re running a hobby—not a company.

There Is a Light at the End of the Tunnel

Rash decisions can have a devastating impact on YOU and your team/employees. If there’s one thing, I’d like for you to take away from this, it is that mistakes are our best teachers. Yep, it’s a cliché and it’s overused: but with good reason.

This whole journey of running a business isn’t linear, and it sure as hell isn’t black and white.

But it’s in these moments where we make mistakes that we can either give up and throw in the towel or look at life from a different lens. Surprise yourself with how much resilience and problem-solving you’re capable of. Rising above is when you get to learn about yourself the most! What are some of your biggest mistakes as an entrepreneur and what did you learn from it? Share your experiences in the comments, you never know who you’re going to help 👇

💡 Want to humanize your brand and build real relationships on LinkedIn? I shared some valuable insights on the How to Sell More podcast with Mark Drager.

Joshua B. Lee on how to sell more

The Secret to LinkedIn Leads

Top 3 Reasons to Listen:

🔵 Discover how to build relationships, not just connections

🔵 Understand the role of personal branding on LinkedIn

🔵 Learn how to empower your team on LinkedIn

I also shared my #1 strategy to sell more on LinkedIn, tune in to the podcast for more insights. Thank you Mark for such a great experience, and I can’t wait to chat again.