Over the last 23 years, I’ve started 5 SaaS businesses and successfully exited 3 of them, making me a millionaire at 27 years old. I could have retired and never worked another day in my life...

I love doing hard things. I learned early in life that the more difficult a challenge, the more rewarding. So, call me crazy, but I deliberately seek out difficult challenges. My family motto is “We do hard things”... And last year, I did one of the most crazy challenges yet.  I did #75Hard.

2020 sucked. Not only for businesses... but for families, communities and economies around the world. Working closely with SaaS founders means I’ve heard the pains, seen the panic and talked through the new reality of Covid 19 for many struggling startups. Some businesses have a model that lets them bend rather than break. Others… aren’t so fortunate.

Have you ever wanted to cut a toxic person out of your life before? It’s a more common feeling than you think. Maybe there’s an old high school friend, a buddy from college, a distant relative… Whoever it is, you know in your gut that this person is toxic and brings negative energy to most conversations. The question is: Is it ok to cut them out of your life?

Between 17 and 24 years old, I built 2 companies... that failed. Why did they fail? Fear. Fear can cripple entrepreneurs and businesses before they’ve even started. Fear of the unknown, fear of making a wrong decision, fear of embarrassment… It’s the internal battle and if you don’t think it’s happening, you’re lying to yourself. Every successful entrepreneur, from Jeff Bezos to Elon Musk to Richard Branson, was once a terrified young adult that no-one knew.

What does success mean? Get specific… what exactly does it look like to you? Is that word just a placeholder for some anonymous measure of public respect and acceptance? Is it about bank account zeros? My idea of success has changed… a lot. The answer I’d have given you when I was 21 is nothing like the answer I’d give you now. Why?

A few weeks ago, I owned up to the biggest mistakes I made in my 20s... mistakes that cost me literally millions. This video is the sequel. Believe it or not, when I turned 30 I didn’t magically become an angel, with a perfect track record of success.  (Shock! I can hear your gasps from here)

So here’s a crazy story.... In January, I started training for an Ironman 70.3 event.  I had never done anything like this before in my life… and I knew it was going to be f-ing hard. I’m 6’3” and weighed 235lbs... I looked more like a linebacker than a skinny triathlete. An Ironman 70.3 (aka: Half Ironman) consists of a 1900m swim, 90km bike ride and 21km run. This is how I broke down my goals:

I’ve got to come clean... I’m not a guru. I can’t read your future, don’t perform miracles, and I’m about as enlightened as a stick. I’m just a SaaS-obsessed business coach that has made WAY too many mistakes, enough to fill entire encyclopaedias of ‘what not to do’. But I did do something right: 

I have a confession... In my mid-20s, I was the worst leader. I was trying to run a team and was wildly out-of-touch with so-called “good leadership”. I just didn’t know it yet. I held a team offsite, a getaway with the executive team to reflect on the quarter, set goals and come away reinvigorated. It didn’t work. My fault. I tried to force passion on the team, crack the whip on our productivity and focus on project management. In