Mark Cuban: Disrupting Industries, Finding Opportunities, and Navigating Your Twenties in an AI World
Meet Mark Cuban, owner of Dallas Mavericks, co-founder of Cost Plus Drugs, and an investor (or “shark”) on “Shark Tank,” an ABC television series featuring entrepreneurs pitching their companies to a panel of angel investors (“sharks”) in hopes of gaining investment.
SCET welcomed Mark Cuban as a guest speaker in the A. Richard Newton Lecture Series course. During the session, students asked him questions around entrepreneurship, post-graduation paths, navigating their early twenties, and their concerns on how AI will impact their futures. Mark responds with encouragement, explaining how he views both AI and their twenties as open doors full of exciting possibilities, and how they can make the most of them.
Table of Contents
I. Being an Entrepreneur ⤴
As a serial entrepreneur, Mark shared the lessons he’s learned from building ventures. Excited Berkeley students (🐻) ask Mark for his views on everything from being “all in” to taking risks early in their careers. Below are some of the students’ questions and Mark’s insights.
🐻: How should entrepreneurs approach competition?
Upon the recent announcement of TrumpRx (a government program that lowers the cost of drug prescriptions), Mark recognizes its similarity to his own company, Cost Plus Drugs, which shares the same goal of providing prescriptions at more accessible costs. Recognizing the potential competition, Mark describes his process when encountering new competition.
1. Do Your Homework.
Research the competition deeply. Use your network and industry contacts to get real insights. Mark’s first step was to reach out to contacts at the U.S. Department of Health and Human Services (HHS) to confirm whether TrumpRx would be entering the pharmacy business. He found that TrumpRx was not planning to sell medication, but rather connect patients with providers.
2. Know Your Differentiator.
Once you understand your competition, define what makes you different. Even if TrumpRx were a direct competitor, Mark explains that Cost Plus Drugs’ technology-driven model enables them to stay competitive on price. The company publishes their costs to be available to consumers and competitors, and Mark remains confident that the company is still in “really good shape” and “prepared to be able to continue to price at only a 15% markup.”
3. Lean Into Your Advantages.
Mark explains that his goal is not to maximize earnings or income, but impact.
“If the writing on the wall is Mark Cuban completely reimagined, redid, and disrupted healthcare, that’s going to be a whole lot more important to me than how much more or less did Mark Cuban [left] when he died.”
This clarity of mission gives Cost Plus Drugs their greatest advantage.
“The number one product that we all offer is trust.”
Mark noted, “trust equals a numerator of transparency and a denominator of self-interest.”
This equation is applicable to every business. Cost Plus Drugs has been in business for three and a half years, yet they’re still the only pharmaceutical that publishes their entire price list.
That transparency, along with their consistent 15% markup, builds trust. That trust is returned to them in business growth without marketing spend.
🐻: What’s the difference between a good vs a great company?
Here’s a list of questions Mark asks himself when testing business ideas:
- “Does it make me say ‘Why didn’t I think of that?’”
- “What about this is unique, differentiated, and sustainable?”
- “Where could I take this? What could I accomplish? How would I sell into this market?”
- “If I were a competitor, how would I put myself out of business?”
Acknowledging that mistakes are inevitable, Mark explains they often fall into two categories:
- Underestimating entrepreneurs who were able to outperform the capabilities of their business
- Overestimating entrepreneurs who couldn’t execute on the issues above
🐻: Advice for technical founders?
1. Learn the Industry and Where You Fit
“What is it about your product, service, or idea that’s going to be so compelling that people can’t say no?”
2. Validate
One of the big challenges that technical entrepreneurs have is overestimating ourselves and telling ourselves “This is the best idea ever. Nobody has done it.”
3. Study Failures
What entrepreneurs miss is that they don’t look at all the companies that went out of business. Do the research to make sure you’re not overselling yourself.
4. Seek Feedback
Who are your customers? Who will invest in your research?
Every idea creates value for someone. Figure out who that is and get their feedback early. When it comes to moving into new spaces, people in the industry want to hear new ideas.
Mark warns against staying quiet out of fear. “Don’t be one of those people who are afraid of sharing the idea because you’re afraid someone’s going to steal it. If it’s going to be stolen, if someone else could do it, they probably already would have.”
At the same time, Mark offers a qualifier: Be strategic about what you make public.
“The days of publish or perish are over,” he notes. “The minute you publish and it’s available to the public, it’s training a model.”
Mark’s advice: “In an era of AI where all the foundational models are training on everything on the internet, make sure to paywall or hide anything advanced that you’re putting out there.”
🐻: What do investors look for in entrepreneurs?
1. “Competitive analysis. Show me why you’re better.”
If an idea can’t be clearly explained in a way that’s easy to understand, “you probably don’t understand it. If you don’t understand it, you’re not going to succeed.”
2. “Can they sell?”
Particularly among tech and young entrepreneurs, Mark often hears the same sentence: “I’m not a salesperson.” This is often followed by plans to hire sales, consulting, or marketing teams.
Mark has seen how that story ends—often in failure. In the early stages, a founder must be their own best salesperson.
“Whatever your product or service is, if you aren’t happy and excited to tell everybody about it, and you don’t believe that everybody you talk to will benefit from it, then you’re not in the right business and you’re not the right person.”
3. “Can they take criticism?”
“The minute you’re telling an investor, ‘No, you’re wrong,’ there’s a 99% chance you’ve lost and you’re not going to get the investment.”
Instead, Mark suggests asking to hear more. This shows respect, self-awareness, and a willingness to grow. It also provides a glimpse of what working with you would look like.
4. “Are they curious?
“Even Mr. Wonderful likes to learn. Shocking to me, but he’s always learning and reading just like all of us.”
Every successful entrepreneur is curious enough to learn how to adapt and stay ahead.
🐻: How do you balance profit with impact?
In business, there’s an order of operations. “First get to profitability. Once you’re profitable you have all your options.”
Mark explains that when you lead with mission but lack the margins, you’re introducing cost structures which will limit real growth and impact. Profitability gives you the ability to scale impact. After a strong financial foundation has been built, you have the freedom to reinvest, experiment, and expand your impact.
🐻: All in… or not?
“If you’re starting a company and you’re hedging your bets, you’ve already lost.”
“You’ve got to always be all in.”
There will not be a perfect moment when everything suddenly makes sense and a path suddenly emerges. If there’s uncertainty, “you’re not ready.”
Mark shares a quote from basketball coach Bob Knight, “Everybody’s got the will to win. But it’s only those with the will to prepare that do win.”
Mark interprets this to do the work upfront, whether it is as an athlete in sports or business. As Mark puts it, “Business is the ultimate sport.”
To read more about training as an entrepreneur, read Mark’s 64-page book, “How to Win at the Sport of Business.”
II. Artificial Intelligence ⤴
AI is on the top of everyone’s minds, including Mark Cuban. Here’s how he views AI.
🐻: How do we navigate AI risk?
As AI becomes universal, what sets companies apart is how they’re using AI. Identifying ways to make systems more productive enables people to do higher-value work, which in turn fuels growth and opens up new kinds of jobs.
While “creative destruction” is inevitable, Mark isn’t worried about job loss. The productivity gains and new opportunities created by AI technologies will open new fields and jobs.
🐻: How will AI change the workforce?
Traditionally, people gravitate towards the biggest companies with the biggest paychecks. However, in this AI world, those same companies are using AI to become leaner and more efficient, requiring fewer people.
Mark explains that there are two types of companies:
- Those who are great at AI.
- Those who went out of business and who got acquired because they weren’t.
Mark’s recommendation is to flip the focus. Rather than seeking jobs at the biggest companies, look for those in small to medium-sized companies. That’s where you are needed the most, and where you can make the most impact.
Since 1995, small businesses have accounted for 62% of new job creation. This is where your opportunities are. At smaller companies, even basic Python skills can open major doors. Helping a business integrate AI tools, optimize processes, and reduce costs can put you in a position where you may negotiate your way into leadership roles or even equity.
🐻: Do you need a technical background to have these opportunities?
Mark says no. Models still need human-based training and reinforcement learning, which will require a variety of skills.
Whether your skills are technical or non-technical, what matters more is the curiosity and adaptability to apply your skills to train the models.
🐻: How will AI change entrepreneurship?
“Consider what type of impact you can have using your entrepreneurial skills.”
There are so many industries that are ripe for disruption, and with AI, they are now less expensive to disrupt.
Find a fresh approach to disrupt an industry. “There’s never been a better time.”
🐻: I think AI is scary…
“Why do you think AI is scary?”
Yes, AI brings uncertainty. It’s massive, changes quickly, and the stakes are high.
“But doesn’t that happen with all new technologies?”
“Every new technology scares someone.” Whether it’s the Internet, mobile phones, or the app store, every transformative technology seemed scary.
While Mark acknowledges AI will be the hardest technology to predict, Mark sees that uncertainty as an open lane.
“To be in my twenties, when everybody else is freaking out about AI… oh my god, that’s like a door to run through. They’re giving you the football, you got all the blockers, and there’s nobody in front of you. Because while it’s maybe a little bit scary to you, it’s terrifying to everybody else.”
“Whenever there’s change, that’s when the most opportunity occurs. And there’s going to be ongoing change with AI.”
If Mark were in his twenties today, he says he would dive into every opportunity he could. The advantage of being young and early in the AI wave is the ability to make mistakes.
“Okay, got that one wrong. Refresh.”
Don’t let fear make you retreat. “All this stuff is right in front of you.”
🐻: Advice to creatives?
AI is about “making creative people more creative. You can iterate so often and so quickly.”
With AI, artists, designers, writers, and marketers will be able to test and refine their ideas in ways that were previously too expensive or time consuming.
AI gives creatives more freedom to experiment. However, now that these tools are available to all, it also means there are more competitors. Creatives need to be willing to “zig and zag and go against the grain.”
🐻: How will social media change in an AI world?
Mark believes the next big shift won’t be a new algorithm, but returning to real life experiences. As AI-generated videos continue to flood social media platforms, the internet will become less social and personal.
We’ve seen the evolution of TikTok from dance trends to entertainment, to news, and direct product selling. Mark predicts the overwhelming waves of AI-generated content will drive people to crave genuine human connection.
Invest in real world experiences that bring people together. When AI can generate infinite content, authenticity and personal connection will become the greatest differentiators.
III. Your Early Twenties ⤴
Welcome to your twenties. The decisions you make in this decade will be transformative and foundational. Here’s Mark’s advice on navigating your twenties.
asks about choosing jobs.
🐻: How do you choose the right job?
The goal is to find a job that pays you to learn.
No matter what job you take, choose roles that teach you skills you can take to your next job or the next company you build.
Mark explains his worst jobs have taught him the most. They showed him what bad management looks like and habits to avoid.
“Just go in and learn.” Even if you’re not starting with your dream job, find ways to learn new skills, try new things, and make an impact.
“If something comes along that gets me going, let’s go.”
🐻: What’s a valuable skill as AI becomes increasingly prevalent?
“Critical thinking. 100%.”
On Shark Tank, the other “sharks” (investors) call Mark “the computer.” Within minutes of hearing a pitch, he can map out their business model, their roadblocks, and paths to profitability.
“The reason I’ve been able to be disruptive so many times is I can look at processes and figure out how to break them down to become more profitable and more economic.”
If you can walk into a business, talk to people, understand their workflows, and then use AI tools to make them better, you’ll always be valuable. Mark shares a story of someone he advised at a marketing agency who helped the company build AI agents. Realizing the company had become dependent on him, Mark told him to ask for a raise and equity. They agreed.
While coding skills may “wash out,” being able to critically think, understand processes, and create smarter systems will never become obsolete.
🐻: How can you develop different mental modes when you’re young?
Absorb as much as you can. Mark read every business book and talked to every business person he could find.
One particular topic Mark enjoys reading is scam businesses.
Scam businesses reveal mistakes and different processes. To Mark, it was “like reading murder mysteries, only business murders.”
🐻: Are there any risks you wish you avoided?
“Not really. All the risks added up.”
Mark made mistakes, heard “no” more times than he could count, and was called several names along the way. However, he kept telling himself, “Every no gets me closer to a yes.”
“All I had to do was get it right one time.”
Daymond John, a fellow Shark Tank investor, calls it “the power of broke.”
When he started his first company, Mark slept on the floor of a three-bedroom apartment he shared with five roommates. He explains, “I had nothing to lose. Nothing was a risk to me.”
“When you’re young, it’s not a risk.”
Take the opportunity and figure it out from there.
🐻: What’s the best advice you’ve received?
As Mark puts it, he likes to “go, go, go.” Early in his career, a mentor sat Mark down and told him, “Every time you’re in a meeting and taking notes, write in the upper right hand corner: ‘Listen.’”
To this day, Mark continues this habit as a reminder to slow down and stay present.
He’s since added another rule to be a better listener: remembering why he is in the room.
“I’m not here to waste time. If somebody’s adding value, I better pay attention. I don’t want to be in a position where I miss something.”
🐻: How much of success is hard work vs luck?
“I’m one of those guys who thinks life is half random.”
“There’s things that we can control: our effort, our approach, our curiosity, and how much we learn. But there’s certain things that’s just going to happen.”
Not everything can be optimized or predicted.
When things are good, Mark advises to “just say thank you.”
When things aren’t going so well, “that’s just the way it goes.”
“Recognize your circumstances and adapt accordingly.” Rather than focusing on controlling the event, focus on your response.
🐻: How did you learn to communicate effectively?
Mark’s “first real company” was MicroSolutions, which initially operated as a systems integrator.
Whether it was a shoe store, a bank, a law firm, or a jewelry store, “I had to be able to walk into a company and put myself in their shoes.”
Before the conversation, Mark goes through his list of questions:
- “If I were running this business, how would I implement technology to their benefit?”
- “How can I make them more profitable?”
- “How can I make them more productive?”
asks about effective communication.
This reflection allowed him to understand their pain points so he can tailor his responses accordingly.
With Cost Plus Drugs, Mark engages in the same practice. He asks questions to understand their perspective.
- “What is it about a person that can’t afford their medications? What are they going through?”
- “Why is it that there are some people that end up in line at a pharmacy and then have to turn away when they find out they can’t afford the price or they misunderstood what was going on? What led to that?”
- “If I were them, what got me to that point? How can I correct that? How can I undo it?”
To communicate in ways that reach your audience, really understand your audience’s world and their pain points. This allows you to directly see them and talk to them.
Mark’s Advice to Gen Z
Mark explains there isn’t a difference being one generation or another.
“Now I’m the oldest walking into the room, but I used to be the youngest walking in the room.”
“That was my superpower, because the expectations weren’t high. The fact that I knew what I was talking about and I was prepared to knock them over made them want to help me more.”
Your priority is to develop strong relationships and earn their trust.
Mark’s Message to College Students and Recent Grads
“Look around you. Every single thing in the room you’re in right now is not organic; It was somebody’s idea. One day, it didn’t exist, and the next day someone had this idea and turned it into the product that you see right now.”
“Don’t let anything stop you. There’s always room for new ideas. There’s always room to be an entrepreneur, and this country depends on it.”
Mark closes, encouraging everyone to pay attention to their ideas and the opportunities around them, especially now as AI opens new frontiers.
“Don’t be afraid. It doesn’t matter how many times you fail. You only got to be right one time, and then everybody can tell you how lucky you are.”
Meet Mark Cuban, owner of Dallas Mavericks, co-founder of Cost Plus Drugs, and an investor (or “shark”) on “Shark Tank,” an ABC television series featuring entrepreneurs pitching their companies to a panel of angel investors (“sharks”) in hopes of gaining investment.
SCET welcomed Mark Cuban as a guest speaker in the A. Richard Newton Lecture Series course. During the session, students asked him questions around entrepreneurship, post-graduation paths, navigating their early twenties, and their concerns on how AI will impact their futures. Mark responds with encouragement, explaining how he views both AI and their twenties as open doors full of exciting possibilities, and how they can make the most of them.
Table of Contents
I. Being an Entrepreneur ⤴
As a serial entrepreneur, Mark shared the lessons he’s learned from building ventures. Excited Berkeley students (🐻) ask Mark for his views on everything from being “all in” to taking risks early in their careers. Below are some of the students’ questions and Mark’s insights.
🐻: How should entrepreneurs approach competition?
Upon the recent announcement of TrumpRx (a government program that lowers the cost of drug prescriptions), Mark recognizes its similarity to his own company, Cost Plus Drugs, which shares the same goal of providing prescriptions at more accessible costs. Recognizing the potential competition, Mark describes his process when encountering new competition.
1. Do Your Homework.
Research the competition deeply. Use your network and industry contacts to get real insights. Mark’s first step was to reach out to contacts at the U.S. Department of Health and Human Services (HHS) to confirm whether TrumpRx would be entering the pharmacy business. He found that TrumpRx was not planning to sell medication, but rather connect patients with providers.
2. Know Your Differentiator.
Once you understand your competition, define what makes you different. Even if TrumpRx were a direct competitor, Mark explains that Cost Plus Drugs’ technology-driven model enables them to stay competitive on price. The company publishes their costs to be available to consumers and competitors, and Mark remains confident that the company is still in “really good shape” and “prepared to be able to continue to price at only a 15% markup.”
3. Lean Into Your Advantages.
Mark explains that his goal is not to maximize earnings or income, but impact.
“If the writing on the wall is Mark Cuban completely reimagined, redid, and disrupted healthcare, that’s going to be a whole lot more important to me than how much more or less did Mark Cuban [left] when he died.”
This clarity of mission gives Cost Plus Drugs their greatest advantage.
“The number one product that we all offer is trust.”
Mark noted, “trust equals a numerator of transparency and a denominator of self-interest.”
This equation is applicable to every business. Cost Plus Drugs has been in business for three and a half years, yet they’re still the only pharmaceutical that publishes their entire price list.
That transparency, along with their consistent 15% markup, builds trust. That trust is returned to them in business growth without marketing spend.
🐻: What’s the difference between a good vs a great company?
Here’s a list of questions Mark asks himself when testing business ideas:
- “Does it make me say ‘Why didn’t I think of that?’”
- “What about this is unique, differentiated, and sustainable?”
- “Where could I take this? What could I accomplish? How would I sell into this market?”
- “If I were a competitor, how would I put myself out of business?”
Acknowledging that mistakes are inevitable, Mark explains they often fall into two categories:
- Underestimating entrepreneurs who were able to outperform the capabilities of their business
- Overestimating entrepreneurs who couldn’t execute on the issues above
🐻: Advice for technical founders?
1. Learn the Industry and Where You Fit
“What is it about your product, service, or idea that’s going to be so compelling that people can’t say no?”
2. Validate
One of the big challenges that technical entrepreneurs have is overestimating ourselves and telling ourselves “This is the best idea ever. Nobody has done it.”
3. Study Failures
What entrepreneurs miss is that they don’t look at all the companies that went out of business. Do the research to make sure you’re not overselling yourself.
4. Seek Feedback
Who are your customers? Who will invest in your research?
Every idea creates value for someone. Figure out who that is and get their feedback early. When it comes to moving into new spaces, people in the industry want to hear new ideas.
Mark warns against staying quiet out of fear. “Don’t be one of those people who are afraid of sharing the idea because you’re afraid someone’s going to steal it. If it’s going to be stolen, if someone else could do it, they probably already would have.”
At the same time, Mark offers a qualifier: Be strategic about what you make public.
“The days of publish or perish are over,” he notes. “The minute you publish and it’s available to the public, it’s training a model.”
Mark’s advice: “In an era of AI where all the foundational models are training on everything on the internet, make sure to paywall or hide anything advanced that you’re putting out there.”
🐻: What do investors look for in entrepreneurs?
1. “Competitive analysis. Show me why you’re better.”
If an idea can’t be clearly explained in a way that’s easy to understand, “you probably don’t understand it. If you don’t understand it, you’re not going to succeed.”
2. “Can they sell?”
Particularly among tech and young entrepreneurs, Mark often hears the same sentence: “I’m not a salesperson.” This is often followed by plans to hire sales, consulting, or marketing teams.
Mark has seen how that story ends—often in failure. In the early stages, a founder must be their own best salesperson.
“Whatever your product or service is, if you aren’t happy and excited to tell everybody about it, and you don’t believe that everybody you talk to will benefit from it, then you’re not in the right business and you’re not the right person.”
3. “Can they take criticism?”
“The minute you’re telling an investor, ‘No, you’re wrong,’ there’s a 99% chance you’ve lost and you’re not going to get the investment.”
Instead, Mark suggests asking to hear more. This shows respect, self-awareness, and a willingness to grow. It also provides a glimpse of what working with you would look like.
4. “Are they curious?
“Even Mr. Wonderful likes to learn. Shocking to me, but he’s always learning and reading just like all of us.”
Every successful entrepreneur is curious enough to learn how to adapt and stay ahead.
🐻: How do you balance profit with impact?
In business, there’s an order of operations. “First get to profitability. Once you’re profitable you have all your options.”
Mark explains that when you lead with mission but lack the margins, you’re introducing cost structures which will limit real growth and impact. Profitability gives you the ability to scale impact. After a strong financial foundation has been built, you have the freedom to reinvest, experiment, and expand your impact.
🐻: All in… or not?
“If you’re starting a company and you’re hedging your bets, you’ve already lost.”
“You’ve got to always be all in.”
There will not be a perfect moment when everything suddenly makes sense and a path suddenly emerges. If there’s uncertainty, “you’re not ready.”
Mark shares a quote from basketball coach Bob Knight, “Everybody’s got the will to win. But it’s only those with the will to prepare that do win.”
Mark interprets this to do the work upfront, whether it is as an athlete in sports or business. As Mark puts it, “Business is the ultimate sport.”
To read more about training as an entrepreneur, read Mark’s 64-page book, “How to Win at the Sport of Business.”
II. Artificial Intelligence ⤴
AI is on the top of everyone’s minds, including Mark Cuban. Here’s how he views AI.
🐻: How do we navigate AI risk?
As AI becomes universal, what sets companies apart is how they’re using AI. Identifying ways to make systems more productive enables people to do higher-value work, which in turn fuels growth and opens up new kinds of jobs.
While “creative destruction” is inevitable, Mark isn’t worried about job loss. The productivity gains and new opportunities created by AI technologies will open new fields and jobs.
🐻: How will AI change the workforce?
Traditionally, people gravitate towards the biggest companies with the biggest paychecks. However, in this AI world, those same companies are using AI to become leaner and more efficient, requiring fewer people.
Mark explains that there are two types of companies:
- Those who are great at AI.
- Those who went out of business and who got acquired because they weren’t.
Mark’s recommendation is to flip the focus. Rather than seeking jobs at the biggest companies, look for those in small to medium-sized companies. That’s where you are needed the most, and where you can make the most impact.
Since 1995, small businesses have accounted for 62% of new job creation. This is where your opportunities are. At smaller companies, even basic Python skills can open major doors. Helping a business integrate AI tools, optimize processes, and reduce costs can put you in a position where you may negotiate your way into leadership roles or even equity.
🐻: Do you need a technical background to have these opportunities?
Mark says no. Models still need human-based training and reinforcement learning, which will require a variety of skills.
Whether your skills are technical or non-technical, what matters more is the curiosity and adaptability to apply your skills to train the models.
🐻: How will AI change entrepreneurship?
“Consider what type of impact you can have using your entrepreneurial skills.”
There are so many industries that are ripe for disruption, and with AI, they are now less expensive to disrupt.
Find a fresh approach to disrupt an industry. “There’s never been a better time.”
🐻: I think AI is scary…
“Why do you think AI is scary?”
Yes, AI brings uncertainty. It’s massive, changes quickly, and the stakes are high.
“But doesn’t that happen with all new technologies?”
“Every new technology scares someone.” Whether it’s the Internet, mobile phones, or the app store, every transformative technology seemed scary.
While Mark acknowledges AI will be the hardest technology to predict, Mark sees that uncertainty as an open lane.
“To be in my twenties, when everybody else is freaking out about AI… oh my god, that’s like a door to run through. They’re giving you the football, you got all the blockers, and there’s nobody in front of you. Because while it’s maybe a little bit scary to you, it’s terrifying to everybody else.”
“Whenever there’s change, that’s when the most opportunity occurs. And there’s going to be ongoing change with AI.”
If Mark were in his twenties today, he says he would dive into every opportunity he could. The advantage of being young and early in the AI wave is the ability to make mistakes.
“Okay, got that one wrong. Refresh.”
Don’t let fear make you retreat. “All this stuff is right in front of you.”
🐻: Advice to creatives?
AI is about “making creative people more creative. You can iterate so often and so quickly.”
With AI, artists, designers, writers, and marketers will be able to test and refine their ideas in ways that were previously too expensive or time consuming.
AI gives creatives more freedom to experiment. However, now that these tools are available to all, it also means there are more competitors. Creatives need to be willing to “zig and zag and go against the grain.”
🐻: How will social media change in an AI world?
Mark believes the next big shift won’t be a new algorithm, but returning to real life experiences. As AI-generated videos continue to flood social media platforms, the internet will become less social and personal.
We’ve seen the evolution of TikTok from dance trends to entertainment, to news, and direct product selling. Mark predicts the overwhelming waves of AI-generated content will drive people to crave genuine human connection.
Invest in real world experiences that bring people together. When AI can generate infinite content, authenticity and personal connection will become the greatest differentiators.
III. Your Early Twenties ⤴
Welcome to your twenties. The decisions you make in this decade will be transformative and foundational. Here’s Mark’s advice on navigating your twenties.
asks about choosing jobs.
🐻: How do you choose the right job?
The goal is to find a job that pays you to learn.
No matter what job you take, choose roles that teach you skills you can take to your next job or the next company you build.
Mark explains his worst jobs have taught him the most. They showed him what bad management looks like and habits to avoid.
“Just go in and learn.” Even if you’re not starting with your dream job, find ways to learn new skills, try new things, and make an impact.
“If something comes along that gets me going, let’s go.”
🐻: What’s a valuable skill as AI becomes increasingly prevalent?
“Critical thinking. 100%.”
On Shark Tank, the other “sharks” (investors) call Mark “the computer.” Within minutes of hearing a pitch, he can map out their business model, their roadblocks, and paths to profitability.
“The reason I’ve been able to be disruptive so many times is I can look at processes and figure out how to break them down to become more profitable and more economic.”
If you can walk into a business, talk to people, understand their workflows, and then use AI tools to make them better, you’ll always be valuable. Mark shares a story of someone he advised at a marketing agency who helped the company build AI agents. Realizing the company had become dependent on him, Mark told him to ask for a raise and equity. They agreed.
While coding skills may “wash out,” being able to critically think, understand processes, and create smarter systems will never become obsolete.
🐻: How can you develop different mental modes when you’re young?
Absorb as much as you can. Mark read every business book and talked to every business person he could find.
One particular topic Mark enjoys reading is scam businesses.
Scam businesses reveal mistakes and different processes. To Mark, it was “like reading murder mysteries, only business murders.”
🐻: Are there any risks you wish you avoided?
“Not really. All the risks added up.”
Mark made mistakes, heard “no” more times than he could count, and was called several names along the way. However, he kept telling himself, “Every no gets me closer to a yes.”
“All I had to do was get it right one time.”
Daymond John, a fellow Shark Tank investor, calls it “the power of broke.”
When he started his first company, Mark slept on the floor of a three-bedroom apartment he shared with five roommates. He explains, “I had nothing to lose. Nothing was a risk to me.”
“When you’re young, it’s not a risk.”
Take the opportunity and figure it out from there.
🐻: What’s the best advice you’ve received?
As Mark puts it, he likes to “go, go, go.” Early in his career, a mentor sat Mark down and told him, “Every time you’re in a meeting and taking notes, write in the upper right hand corner: ‘Listen.’”
To this day, Mark continues this habit as a reminder to slow down and stay present.
He’s since added another rule to be a better listener: remembering why he is in the room.
“I’m not here to waste time. If somebody’s adding value, I better pay attention. I don’t want to be in a position where I miss something.”
🐻: How much of success is hard work vs luck?
“I’m one of those guys who thinks life is half random.”
“There’s things that we can control: our effort, our approach, our curiosity, and how much we learn. But there’s certain things that’s just going to happen.”
Not everything can be optimized or predicted.
When things are good, Mark advises to “just say thank you.”
When things aren’t going so well, “that’s just the way it goes.”
“Recognize your circumstances and adapt accordingly.” Rather than focusing on controlling the event, focus on your response.
🐻: How did you learn to communicate effectively?
Mark’s “first real company” was MicroSolutions, which initially operated as a systems integrator.
Whether it was a shoe store, a bank, a law firm, or a jewelry store, “I had to be able to walk into a company and put myself in their shoes.”
Before the conversation, Mark goes through his list of questions:
- “If I were running this business, how would I implement technology to their benefit?”
- “How can I make them more profitable?”
- “How can I make them more productive?”
asks about effective communication.
This reflection allowed him to understand their pain points so he can tailor his responses accordingly.
With Cost Plus Drugs, Mark engages in the same practice. He asks questions to understand their perspective.
- “What is it about a person that can’t afford their medications? What are they going through?”
- “Why is it that there are some people that end up in line at a pharmacy and then have to turn away when they find out they can’t afford the price or they misunderstood what was going on? What led to that?”
- “If I were them, what got me to that point? How can I correct that? How can I undo it?”
To communicate in ways that reach your audience, really understand your audience’s world and their pain points. This allows you to directly see them and talk to them.
Mark’s Advice to Gen Z
Mark explains there isn’t a difference being one generation or another.
“Now I’m the oldest walking into the room, but I used to be the youngest walking in the room.”
“That was my superpower, because the expectations weren’t high. The fact that I knew what I was talking about and I was prepared to knock them over made them want to help me more.”
Your priority is to develop strong relationships and earn their trust.
Mark’s Message to College Students and Recent Grads
“Look around you. Every single thing in the room you’re in right now is not organic; It was somebody’s idea. One day, it didn’t exist, and the next day someone had this idea and turned it into the product that you see right now.”
“Don’t let anything stop you. There’s always room for new ideas. There’s always room to be an entrepreneur, and this country depends on it.”
Mark closes, encouraging everyone to pay attention to their ideas and the opportunities around them, especially now as AI opens new frontiers.
“Don’t be afraid. It doesn’t matter how many times you fail. You only got to be right one time, and then everybody can tell you how lucky you are.”