Khary Penebaker on Losing Everything and Finding Joy at Home – Episode 89

In today’s episode, we are joined by our good friend Khary Penebaker. Khary puts it all out on the table in this conversation, it’s hard not to feel gripped with fear as you’re listening to him recount his defining shut up moments. He talks to us about being ill-prepared for success when it came early on in life and how believing he was invincible impacted many poor decisions ultimately leading to major back injuries and losing a multi-million dollar company. This is a deep conversation about losing everything that never really mattered and finding joy right at home.

Watch the show (uncensored & unedited)

Share Some Shut Up Love –> I was making statements. I kept doing. But the problem is I don’t know who I was making them to or why. – @KPenebaker #shutupshow (click to tweet)

Fun Facts:

  • Khary went from laborer to sales and part-owner of a roofing company at age 18.
  • Khary owned one of the 10 largest roofing companies in WI from 2002 – 2011.
  • Khary’s failures led him to lose a multi-million dollar company, foreclosures, and federal bankruptcy court.
  • Khary was a scholarship track athlete in college who had four spinal surgeries in his lifetime.
  • Khary was the original Joy Champion featured in MeiMei Fox’s #40DaysOfJoy project, which Berni joined during the second round.

Defining Shut Up Moment:

ON BECOMING AN ENTREPRENEUR AT 18:  I went to an all boy’s Catholic High School, which gave me the drive want more than just a job. They taught us, don’t look forward to getting a job, look forward to being the job. I learned to be the person other people want to be around. I was a scholarship track athlete at UWM, which some of the records I broke still stand. In the student union there were post cards advertising “Do you wanna get high legally?” and the guy’s phone number. It was 1996. I was 18 years old. I was already hooked so I called him. I got hired right away making $10 an hour. Within three months, I came from being the laborer to selling for the company. Another three months later, I became part-owner of a roofing company. I was 18-1/2 years old. That is how I became an entrepreneur. I may not know everything but I believe I can do everything. Just wanting to “do” is the thesis of everything in my life.

ON PREMATURELY REACHING SUCCESS AND FAILING HARD:  I’ve been a roofer my entire adult life. The successes I had only led to a lot more consequences in the future because I was so young and so ill-prepared mentally to deal with the success that was coming towards me whether it was the notoriety, fame or money. There’s no “being successful for dummies.” People always tell you to be successful but they don’t tell you what that means. The first chink in my armor came in 1999 when I had my first back surgery. It was probably one of the worst moments physically I can remember. I’ve had four spinal surgeries. I was bed ridden and had a hard time working. Having to be a roofer at the same time did not help me. Within 6 to 8 weeks after my surgery, I was competing again. That is the dumbest thing you can do. But you watch Sports Center enough and you assume this is just how things go. I believed I was invincible. Once I got into the blocks the first time again, I got scared shitless. I wasn’t scared I was going to get hurt again. I was afraid I was going to lose. Once you take confidence away from an athlete, talent means nothing. I was so terrified of losing so much that I lost before I even got off the blocks.

Shut Up Tips:

Once you take confidence away from an athlete, talent means nothing. – Khary Penebaker

Being a young successful athlete, they don’t teach you how to deal with failure at all. Either you are a mediocre athlete and you get some support and attention or you’re a really good athlete and they don’t tell you the dark side of the competition. – Khary Penebaker

The whole time I was trying to prove a point to myself. It’s almost like you could divide me in two. The one side was doing. The other side was waiting to be proved to that I could do the thing I’m already doing. – Khary Penebaker

What hurt me professionally is I didn’t listen. – Khary Penebaker

It took being unemployed again for me to realize you can’t keep blaming everyone else. This is your shit. I’ve got to stop being afraid of being me. I’m good at what I am for a reason. That also means not everyone is gonna take me in full doses either. – Khary Penebaker

I’m not as awesome as I dreamed I once was. I don’t have six-pack abs anymore, I have a one-pack. I don’t have all the answers but beyond all that I have to accept the fact that I’m a young man. I’ve got a wife and three kids who all care about me. They still love me so I can’t be all that bad. – Khary Penebaker 

Khary Recommends:

40 Days of Joy helped me get out of the funk I was in. Doing that exercise (“40 Ways to Find Joy in Your Everyday Life”) helped me realize the smaller things in life matter more than buying a dumb ass car. It helped me simplify things to put family first and business second. It helped me refocus everything. I don’t know where I’d be if I didn’t find MeiMei Fox‘s happiness practice.

Find Khary:

Tweet with Khary at @kpenebaker