How a make or break business bet gave me new perspective on my entrepreneurial life

I see your bet and I raise you!” I almost laughed as I said it, but I was supremely confident even though my buddy’s jaw practically hit the ground. And, of course, I had no idea that bet was about to cost my company $1.3 million and slash $9 million more off our revenue over the next year. But we had been drinking and had had some fun betting on other stuff throughout the night. Nothing seemed real.

That’s Vegas for you.

welcome to las vegas

We were in the Playboy Club. The whole place is designed to mess with your mind. I mean, seriously, they have psychology experts plan the layouts, the music, the surroundings and how everything works. The result? Your poor brain is hammered with so many inputs you’re pretty much guaranteed to make bad decisions—like betting $1.3 million on something you really shouldn’t.


This bet involved a business deal that looked like it would take my already successful business and skyrocket the profits through the roof. However, you also need to know that if I had done my due diligence—even a tiny bit—I would have quickly seen this deal was doomed from the start. But I didn’t. I had no idea the epic journey my decision would take me on.


So what happened? Well, aside from causing financial devastation within the company (you try keeping things rolling when your revenue plummets from $10 million a year to $1 million a year), negative effects cascaded between my team and myself in nearly every way. It all compounded to bring my company to its knees.


Just a year after that crazy night in Vegas, I found myself phoning dozens of lawyers to see if anybody would take my case (what had happened was borderline illegal, and I thought the right lawyer could help me get things back on track). The good news was yes, several lawyers swore they could help, but they all wanted a $100,000 retainer. Sure, one hundred grand doesn’t seem like a lot of money for a company that generates $10 million a year, but when your revenue drops by 90 percent and you continue to hemorrhage money while trying to stay afloat, spare cash is suddenly hard to come by.

empty wallet

I endured many sleepless nights trying to figure out what to do. Should I bust my ass and do everything in my power to raise the $100,000? I knew I could get the money together if I put my mind to it and hustled, but I also knew it would take complete focus. If I went down that rabbit hole, I would be making the business worse before it got better because I wouldn’t be able to devote the time it required.

In the end, I dropped the whole legal situation, took my lumps, and simply concentrated on rebuilding the business. It took a lot of back and forth to get to that point, and it was emotionally exhausting.

As I look back now, I see so many little decisions I made that led up to that moment. I could have avoided the whole situation, or even turned it into a huge positive, just by doing one or two things differently. I have truly learned from that crippling event. You could say it’s what led to me becoming the person I am today—much more centered, and not only more financially successful, but more successful in every aspect of life.

With the benefit of a few more years’ experience, both in life and business, I came to realize that painful moment was a tipping point for me, like the first domino to fall. I needed to get my entire life together, not just my business life. I had to make upgrades in every area if I was to have the life I wanted.

I tell you this story because I think it has some shock value. I also want to set the tone that I’ll always be open with you about the mistakes I’ve made so you can learn from them. To paraphrase Warren Buffett, mistakes are the best way to learn, especially when you learn from the mistakes of others. You’ll still make your own mistakes, but I hope learning from mine will make your mistakes smaller, your recovery faster and without all the turmoil.

    warren buffet quote

    That event, as horrifying and traumatic as it was, became a seed in my mind and would later become what I call the Integrated Life Formula. I believe in the Integrated Life Formula of true prosperity: vision, health, relationships, and then business, but that’s a story for another time.

    Mark Your Calendars

    How to Use Social Audio to Grow Your Brand -March 24th | 2pmCST
    For years now video has been the biggest trend in digital marketing across all channels, but that’s about to change.

    What’s going to take its place?

    The once and future king… audio. (insert record scratch here.)


    The resurgence of audio as a tool, as a method of reaching your audience and as the main means of communicating with your market – is back in a big way.

    From podcasts to Clubhouse and now LinkedIn Audio – the landscape is changing rapidly.

    And with social audio, we have a two- way conversation with people you’d never imagine talking to. It’s the best of all worlds, where you’re not just listening but being heard…Because people want to NOT JUST BE SEEN, BUT BE HEARD. That’s what the human revolution is about.

    If you’re not doing audio on a regular basis – you’re missing out on a HUGE opportunity to connect. Plus, really… as opposed to video – when it’s audio, it’s “Pants Optional”

    We’ll talk about:

    ???? What social audio is

    ???? Which platforms you can use

    ???? How to build your personal brand and grow a following

    ???? Best practices to creating your own rooms and promoting it

    Register here:


    how to use social audio to grow your brand