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The Diary Of A CEO · 3 min · Oct 26, 2026

Learning software faster gave Cuban an edge

After getting fired, Mark Cuban taught himself unfamiliar PC software by studying manuals after hours. He aimed to be second only to the person who created each program, a strategy he later applied to new technology.

Mark Cuban

Mark Cuban is an entrepreneur and investor.

Led Dallas Mavericks to 2011 NBA title; built Cost Plus Drugs, the transparent online pharmacy, and Broadcast.com.

About this segment

After getting fired, Mark Cuban taught himself unfamiliar PC software by studying manuals after hours. He aimed to be second only to the person who created each program, a strategy he later applied to new technology.

From “Mark Cuban: The Brutal Truth About The Next Market Crash!”, Oct 26, 2026. Watch the full episode

“In my mind, when it came to software, there was only going to be one person who understood any given software better than me”
Mark Cubanat 23:59 · The Diary Of A CEO23:59

Takeaways

  1. Cuban treated getting fired as the push to start his own company.
  2. He learned software by studying manuals and practicing after hours.
  3. His goal was to learn faster than nearly everyone else.

In this episode

Full episode
  1. 39:52AI agents can expand output and create new work5:34
  2. 31:09AI predicts patterns but lacks human understanding6:43
  3. 51:34AI infrastructure debt could intensify a market downturn4:38
  4. 8:25Profitability kept MicroSolutions alive for eight years2:51
  5. 22:06Learning software faster gave Cuban an edge3:11

Up next · The Builders with Walter IsaacsonMusk says he stayed in government too long5:22

Transcript

From the transcript The Diary Of A CEO publishes with the episode.

  1. 22:16

    One of the things that a lot of people who feel stuck are probably thinking about is they're probably trying to weight mentally the amount of sacrifice it's going to take. And when I've heard you talk about hard work and the sacrifices that you had to take to build yourself from this sort of 22-year-old who... is in Pittsburgh, I believe at the time, to starting your first business, which ended up being acquired, Micro Solutions.

  2. 22:38

    What does the sacrifice look like? If I was a fly on the wall, when you were, presumably you had a job at that time, and then you started building the business, what would I have seen in terms of your, how did your life look? So when I got to Dallas, Moved in with, like I said, five roommates. Didn't have a bed. I just slept on the floor. I mean, that's an example of sacrifice, living in a shithole.

  3. 22:59

    Got a job working at night as a bartender, but then almost immediately got a job working at a software store. And that was going to be, for me, my first step into a real job, right, where I could have a future. But I got fired nine months later. Cool. Yeah. I wanted to move out of the shithole I lived in, and I was going to be looking at a $1,500 commission, which would have done it for me. So I called my boss, and I'm like, I need to go pick up this check.

  4. 23:22

    You'll make money. I'll make money. And I have somebody to cover opening up the retail store that I worked in. And he was like, no, I need you in the store. And I made the executive decision to go pick up the check, thinking when I brought it in, everything would be well. He fired me on the spot. fired me, and I'm like, okay, you know, I suck as an employee. This is not what I want. I'm going to start my own company.

  5. 23:45

    And I don't know if I'd call it sacrifice, but I'd call it deferring immediate gratification. You know, I knew that it was going to take time for me to get any level of success to move out of that apartment. I was going to have to sell hard, learn stuff I didn't understand. This was the early days of the PC revolution when PCs were starting to happen. I don't know this shit, but either does anybody else.

  6. 24:08

    In my mind, when it came to software, there was only going to be one person who understood any given software better than me, and that would be the person who wrote it. And that if I busted my ass, I was tied for second, right? When that's new program like Lotus 1-2-3, if you remember that one kid, no, shut up. It was the second spreadsheet that was a big spreadsheet. And so anyways, my idea was I was going to put in the time to learn that software, however many software packages that is, more than everybody.

  7. 24:39

    And I literally would stay in that retail store overnight or I'd take the computer back to the shithole apartment and just sit there and teach myself and teach myself. Read the manuals over and over because if I can get ahead of everybody else to be in second by myself... I would have a huge edge over everybody else in my, you know, for micro solutions. It's the same with AI. New AI comes out, new model comes out, new software comes out.

  8. 25:05

    There's the creator and everybody else is tied for second. And I'm going to kick their ass by learning it faster, better.