Mark Cuban on Success and Motivation

Startup Library
3 min readOct 24, 2022

I recently came across this tweet from Mark Cuban referring to two blog posts he wrote in 2004. In it, he describes his starting point at 24 years old. I made a 500-word summary from the 2200-word blog post highlighting the key takeaways. You can read the original post here and part 2 here.

In short; Mark Cuban had dreams like all of us, he educated himself on topics he was insecure about. He had doubts, a lot of jobs, and no idea what he wanted when he was young. Reading this will show you how the mindset of a future Billionaire works and how similar his challenges were compared to any of us. Or as he states: If I can become successful anyone can.

Keep dreaming: Mark Cuban dreamt of success too. Driving by big houses wondering who lived there and what they did.

Educate yourself: Mark’s mindset regarding every book he read: If I can get 1 good idea out of it, it would pay for the book.

Your mindset regarding jobs: Mark had lots of different jobs. Some he liked but didn’t contribute to a career. And some he hated.

Whatever the job and how I felt about it, I was getting paid to learn and every experience would be of value when I figured out what I wanted.

On confidence & doubt: I wanted to run my own business but I had as much doubt as I had confidence. I just hoped the confidence would beat the doubt.

On spending: I lived very basically. Not a nice place, my closet was a pile of clothes.

On living: I didn’t live my best life but I did have fun. Don’t confuse the road to success with removing fun (and occasional stupidity) from your life.

On deciding what you want: I wasn’t sure what I wanted to do. I made a list of different jobs I would love to do. But I wasn’t qualified for any of them. So I took a job as a bartender to pay the bills and kept looking for my next opportunity during the day.

I found an ad for a job that was on my list. I got an opportunity for an interview because not many people applied. I didn’t care.

On experience: My basic interview skills didn’t impress them, and I obviously didn’t have the right experience. Still, I landed the job because I answered 1 question right.

The question:

What do you do if a customer has a question about a software package and you don’t know the answer?

My answer:

I blurted out that “I would look it up in the manual and find the answer for them.”

How to beat imposter syndrome: I was fired up about the opportunity but I was scared. Because I knew nothing about software. The key to overcoming was rationalizing. Everyone walking through that door knows as little as you. So if I would just do what I told my boss during the interview I would be ahead of the curve. Reading the manuals.

It turns out that really no one reads the manuals. So educating yourself puts you in a position of preeminence. People think you know your stuff.

Because I knew my stuff I soon got consulting gigs on the side. This brought in some extra money.

How did I celebrate this success? Not by buying expensive champagne but by investing in a little more comfort at home. I bought better towels.

About decisions: 9 months into my career I got a call from a prospect asking me to come to his office to close a deal. Not a problem for me but one for my boss. My task was to open the store, not to handle outbound sales.

It’s always the little decisions that have the biggest impact. We all have to make that “make or break” call to follow orders or do what we know is right.

I followed my first instinct: close the sale. I rationalized that you never turn your back on a closed deal. So I called one of my coworkers to come in and open the store. I closed the deal.

The next day I came in, check in hand from a new customer, and got fired.

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