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A Few Million, Some 'L's, and Some 'W's later.

April 17, 2021

Dear 29-year-old, no-experience-having aspiring entrepreneur,

This is your 39-year-old, slightly more successful, still-growing self who has 10 years’ worth of knowledge on your ass: Listen up.  

I feel blessed, and as my close friend, Keith Caraway replies every time I ask him, “how are you doing?”

He says, “I’m doing better than I deserve”.  And that’s how I feel.

I’ve been through more than most, and here are my lessons learned. **Spoiler alert** Most of these lessons come from an entrepreneurial perspective.  Maybe one or two of these will hit home with you.

Here is a brief (super-brief) history to give you a little insight into my past. I have truly traveled the world and experienced numerous cultures.  I’m on my  8th passport.  I had my 21st, 22nd, and 23rd birthdays in Iraq, conducting unconventional warfare. I launched a tech company / start up at age 27.  We reached a value of $2.1 Million, made headlines, then crashed and burned. I lost everything I owned and went dead broke while welcoming my one and only son into this world.


I changed industries, jumped into healthcare/employee benefits, launched a podcast out of nowhere that within 12 months has received national attention and is growing beyond what I ever expected.

Nobody gives a shit about that. Which is exactly one of my points below.        




Here are my lessons learned:


It is widely reported that in the 1995 and 1996 days of Amazon, a bell would ring every time a customer made a purchase.  Fast forward to the current day where, Inc. (NASDAQ; AMZN) has a market cap north of $1 Trillion.

QUESTION: Do you think for one second the extremely brilliant Jeff Bezos and his founding team had it all figured out day one?

ANSWER: Of Course Not.

Moral of the story? Start Now. Not soon, but RIGHT NOW. Have a plan, a dream, or an idea. Study your industry, listen to feedback from your customers if you have any. Make continuous adjustments and push the ball forward one step at a time with an end goal in mind. Nobody has it all figured out on day one.

Lesson 2 – The Team: A to B Life happens.

Personalities happen. Different skill sets develop or are required. Funding happens. Lack of funding happens. Emotions, success, failure all happen. If you’re lucky, Revenue happens.  SHIT HAPPENS. The team that gets you from A to B is most likely not the same team that gets you from B to C. The team will change, and that’s okay.

I’ve experienced it time and time again: Business needs change. A startup is different from a company trying to scale.  The startup team that burns the midnight oil scribbling notes on a white board, full of gunpowder and motivation is a unique breed.  They are the true believers; they were present “pre-revenue”. God bless those types. They start shit and make it happen.  The team that puts more “organization” and “structure” in place, well, God bless them too. Both are essential, and it’s usually not the same team. Don’t burn bridges. Be kind to everybody. Trust your gut and be smart enough to know when a different skill set needs to be brought in.

Lesson 3 – Nobody actually gives a shit about your idea

Okay, take it easy. I’m sure your mom cares. I’m sure your significant other says they care and maybe your next-door neighbor… well, actually, probably not.

Have you ever visited the home of brand-new parents? You walk in, the mom is sitting on the couch looking semi-dead but mostly alive. An 8-day-old baby lays powerless on her lap. You whisper sweet nothings like, “How cute!”. Of course, you truly mean it at the time, you are genuinely happy for this joyous occasion. And then, you leave. You get in your car and by the first stoplight you are back in your own world thinking about your own problems.

When I had my tech company, I was so excited. I shared (with enthusiasm) what we were doing with everybody I knew. I thought we had the greatest idea since sliced bread. I was under the impression everybody would come running to help and support.  But it’s rarely like that.

Whether they don’t care, don’t know how to help, or fear offending by offering help, it's surprising how few people will show up when it truly counts.

Lesson 4 – Reputation is everything. Your network is your golden ticket. Don’t be an asshole.

Reputation is one of the laws of power. A strong reputation can command respect, help win clients, open doors, and provide a little grace period when you mess up. Just like a solid relationship, building a strong reputation takes time and is not easy. Say what you mean and mean what you say. Don’t over commit, and always fulfill your end of the bargain.

Network.  "They" (whoever they is) always say, “it’s not what you know it’s who you know.” I could write for pages on the value of a strong network, but I won’t bore you. Bottom line is everybody knows somebody, and you never know when that somebody can help you. Don’t be an asshole – People want to do business with people they like. It’s that simple.

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