Habits and Hustle – Episode 483

“Mark Cuban's Cold Email Empire: How $750K Investments Turn Into Billion-Dollar Returns”
Host: Jennifer Cohen
Guest: Mark Cuban
Date: September 12, 2025

Episode Overview

In this highly engaging episode, Jennifer Cohen sits down with legendary entrepreneur and investor Mark Cuban to dissect the principles, mindset, and stories behind his investment successes—including multi-million-dollar deals sparked by cold emails. Cuban reveals the habits driving his legendary hustle, his no-nonsense approach to mentorship, and why curiosity is his business superpower. Special focus is given to his transformative investments in Alyssa’s Healthy Cookies, Relativity Space, and especially Cost Plus Drugs, a company aiming to massively disrupt the healthcare space.

Key Discussion Points & Insights

Mark Cuban’s Lean Team and Breakfast Rituals

(01:58) Cuban operates with a surprisingly small core group, even with TV and investment obligations—just 12 people help manage all his Shark Tank and other deals.
- “Just in dealing with the Shark Tank and other deals? Probably 12.” — Mark Cuban [01:58]
Alyssa’s Healthy Cookies: Cuban and Cohen bond over their love for Alyssa’s Healthy Cookies, a Shark Tank investment.
- Backstory: The founder, Doug, went from being homeless to running a $20 million revenue business—all kickstarted by a cold sample to Cuban.
- Cuban’s insight: The initial product was good but impractical (“the cookie would fall apart”), so he suggested rebranding into “Healthy Bites.”
Nutrition Focus: Cuban eats Alyssa’s Healthy Cookies every morning for breakfast—8 bites for just 360 calories.
- “It’s like eating healthy cereal, only it tastes better.” — Mark Cuban [04:13]
No Ads, Just Repeat Customers: The brand spends “not a penny” on advertising, thriving strictly on product quality and consumer loyalty.
- “We’ll make $10 million in profits.” — Mark Cuban [05:13]

Investment Philosophy: Product First, People Second

(06:41–07:14):
- Product is Cuban’s #1 criterion. Then he evaluates the entrepreneur’s execution ability.
- “Product first, because you can have great people, but if it’s not going to sell, it’s not going to work.” — Mark Cuban [06:47]
- “Is this something where I say to myself, why didn’t I think of that?” — Mark Cuban [06:52]
People Matter—But Only If Product Passes:
- Once the product convinces him, then he “looks at the entrepreneur and says, ‘can these people do it?’”

Shark Tank Realities and Due Diligence

(07:42–09:03):
- Pitches on Shark Tank are much longer than what viewers see: “Intense ones, 90 minutes to two hours; medium ones, an hour.” [07:52]
- Sharks know nothing about contestants beforehand—they’re only vetted by producers.
  - “We know nothing about them when they walk into the room.” — Mark Cuban [08:00]
- Due diligence happens after an on-air handshake. 75% of Cuban’s early deals went through, but more are “ghosted” now as contestants use the exposure as a commercial.

Team Dynamics Among Sharks

(09:07–09:55):
- Cuban enjoys partnering with Barbara Corcoran, because she’s people-first while he’s product-first.
  - “We complement each other really well.” — Mark Cuban [09:12]
- Insights into other sharks:
  - Kevin O’Leary “doesn’t do a lot of deals,” Robert is “too nice,” and Lori excels in QVC-friendly products.

Cuban’s Personal Backstory: From Underdog to Billionaire

(10:07–12:13):
- Childhood hustle: selling baseball cards, garbage bags, etc.
- Humble beginnings: Grew up with little money, had steel caps on teeth as a teen because they were cheaper—“Every time I smiled...there would be these two teeth at the bottom that were steel colored.” — Mark Cuban [10:52]
- “Picture me at 16.” (Cuban shows a photo: 5'8", 30 pounds heavier than now.) [11:32]
On Self-Confidence and Work Ethic:
- “The one thing in life you can control is your effort. And so that’s just my style.” — Mark Cuban [12:44]
- “Most people don’t do the work. And so that's what gave me confidence because I knew I do the work prepared and that set me apart always.” — Mark Cuban [13:14]

The Power of Curiosity and Learning

(13:21–15:29):
- “Curiosity is one of the greatest business skills anybody can have.” — Mark Cuban [13:21]
- Cuban spends hours daily learning about new things (“four hours a day”).
- Journey into tech: Landed at a software store in Dallas, learned by reading manuals, taught himself to code and sell.
- No mentors: Cuban never had a mentor. Prefers learning by figuring things out himself.
  - “[Mentorship is] not that I don’t believe in them. To each their own. But...going through the process of figuring things out is a skill.” — Mark Cuban [15:40]

Access and Cold Emails: Mark Cuban’s Open Inbox

(16:21–18:38):
- He gets inundated with email requests—“my email is public.” — Mark Cuban [17:45]
- Instead of mentorship, he answers single, well-asked questions—otherwise, “I just hit the delete key. It takes me two seconds.” [18:11]
- “I’ve literally gotten emails where I’ve invested probably over a hundred million dollars from people I don’t know.” — Mark Cuban [18:21]
  - Notable Deals from Cold Emails:
    - Relativity Space: 3D printed rockets, now worth billions. Cuban gave $750K for ~20% (heavily diluted, “now worth...a whole lot of money”). [18:44–19:17]
    - Cost Plus Drugs: Co-founded after Dr. Ash Mayansko cold-emailed him.

Cost Plus Drugs: Disrupting Big Pharma

(19:19–26:00):
- Origin Story: Dr. Ash Mayansko, a radiologist and mathematician, cold-emailed Cuban with the idea for a compounding pharmacy to lower generic drug costs.
  - “He sends me an email...wanted to create a compounding pharmacy to make generic drugs that are often out of supply...I’m like well that's pretty cool, but that's too short sighted. We gotta do it for all generics.” — Mark Cuban [19:46]
- How It Works:
  - Full price transparency (“we tell you exactly what our cost is for any drug we sell”), only mark up is 15%, plus $3 pharmacy handling and $5 shipping.
  - Recent metrics: nearly 1,000 generic drugs, aiming for close to 2,000 by year-end.
  - Cost Plus Drugs now often beats not just full retail prices, but people’s insurance co-pays.
    - “We thought we were going to mainly deal with people without insurance, but...people with insurance, we’re more often than not cheaper than people’s co-pays.” — Mark Cuban [22:08]
- Broader Impact:
  - Study found just 77 drugs on Cost Plus could save Medicare $3.6 billion/year.
  - Commitment to sell all legally prescribable drugs, including those controversial in some states post-Roe v. Wade like certain birth control and mifepristone generics. [24:08]
- Business Model:
  - No ads, no membership, no hidden fees.
    - “You don’t have to pay a monthly fee, none of that stuff...just straight up. We take our cost plus 15%.” — Mark Cuban [25:33]
  - Exponential growth: “We’re way past what we thought would be two years in.” — Mark Cuban [25:53]

Notable Quotes & Memorable Moments

On Effort and Self-Improvement:
- “The one thing in life you can control is your effort.” — Mark Cuban [12:44]
On Learning:
- “Curiosity is one of the greatest business skills anybody can have.” — Mark Cuban [13:21]
On Investment Philosophy:
- “Product first, because you can have great people, but if it’s not going to sell, it’s not going to work.” — Mark Cuban [06:47]
On Cold Emails:
- “I’ve literally gotten emails where I’ve invested probably over a hundred million dollars from people I don’t know.” — Mark Cuban [18:21]
On Pharmaceutical Disruption:
- “In this country in 2022, we should never be in a position where you have to choose between your rent, your food and your medication.” — Mark Cuban [22:08]
On Cost Plus Drugs’ Promise:
- “You don’t have to pay a monthly fee, none of that stuff. You don’t need a card. It’s just straight up. We take our cost plus 15%.” — Mark Cuban [25:33]
On Business’s Rapid Growth:
- “We’re way past what we thought would be two years in.” — Mark Cuban [25:53]

Timestamps for Major Segments

01:58 — Mark’s core team size; Alyssa’s Healthy Cookies deep dive
06:41 — Cuban’s investment criteria
07:42-08:14 — Shark Tank pitch realities and deals
10:07-12:13 — Childhood hustling and self-confidence
13:14-15:29 — Curiosity, learning, and no mentors
16:21-18:38 — Cold emails and discovering game-changing investments
19:19-22:29 — The founding and model of Cost Plus Drugs
24:19-26:00 — Growth, expanded access, and still disrupting

Conclusion

This episode highlights why Mark Cuban stands out—not only for his sharp business instincts, but for his hands-on, unfiltered approach. From revolutionizing breakfast with simple, nutritious habits, to reading and responding personally to cold emails, to launching companies disrupting entire industries, Cuban shows the raw, daily habits and beliefs that fuel billion-dollar outcomes. Whether you’re a founder, a hustler, or an everyday listener, his advice remains actionable: put in the work, never stop learning, and never underestimate the power of a single email.

Habits and Hustle – Episode 483

“Mark Cuban's Cold Email Empire: How $750K Investments Turn Into Billion-Dollar Returns”
Host: Jennifer Cohen
Guest: Mark Cuban
Date: September 12, 2025

Episode Overview

Key Discussion Points & Insights

Mark Cuban’s Lean Team and Breakfast Rituals

(01:58) Cuban operates with a surprisingly small core group, even with TV and investment obligations—just 12 people help manage all his Shark Tank and other deals.
- “Just in dealing with the Shark Tank and other deals? Probably 12.” — Mark Cuban [01:58]
Alyssa’s Healthy Cookies: Cuban and Cohen bond over their love for Alyssa’s Healthy Cookies, a Shark Tank investment.
- Backstory: The founder, Doug, went from being homeless to running a $20 million revenue business—all kickstarted by a cold sample to Cuban.
- Cuban’s insight: The initial product was good but impractical (“the cookie would fall apart”), so he suggested rebranding into “Healthy Bites.”
Nutrition Focus: Cuban eats Alyssa’s Healthy Cookies every morning for breakfast—8 bites for just 360 calories.
- “It’s like eating healthy cereal, only it tastes better.” — Mark Cuban [04:13]
No Ads, Just Repeat Customers: The brand spends “not a penny” on advertising, thriving strictly on product quality and consumer loyalty.
- “We’ll make $10 million in profits.” — Mark Cuban [05:13]

Investment Philosophy: Product First, People Second

(06:41–07:14):
- Product is Cuban’s #1 criterion. Then he evaluates the entrepreneur’s execution ability.
- “Product first, because you can have great people, but if it’s not going to sell, it’s not going to work.” — Mark Cuban [06:47]
- “Is this something where I say to myself, why didn’t I think of that?” — Mark Cuban [06:52]
People Matter—But Only If Product Passes:
- Once the product convinces him, then he “looks at the entrepreneur and says, ‘can these people do it?’”

Shark Tank Realities and Due Diligence

(07:42–09:03):
- Pitches on Shark Tank are much longer than what viewers see: “Intense ones, 90 minutes to two hours; medium ones, an hour.” [07:52]
- Sharks know nothing about contestants beforehand—they’re only vetted by producers.
  - “We know nothing about them when they walk into the room.” — Mark Cuban [08:00]
- Due diligence happens after an on-air handshake. 75% of Cuban’s early deals went through, but more are “ghosted” now as contestants use the exposure as a commercial.

Team Dynamics Among Sharks

(09:07–09:55):
- Cuban enjoys partnering with Barbara Corcoran, because she’s people-first while he’s product-first.
  - “We complement each other really well.” — Mark Cuban [09:12]
- Insights into other sharks:
  - Kevin O’Leary “doesn’t do a lot of deals,” Robert is “too nice,” and Lori excels in QVC-friendly products.

Cuban’s Personal Backstory: From Underdog to Billionaire

(10:07–12:13):
- Childhood hustle: selling baseball cards, garbage bags, etc.
- Humble beginnings: Grew up with little money, had steel caps on teeth as a teen because they were cheaper—“Every time I smiled...there would be these two teeth at the bottom that were steel colored.” — Mark Cuban [10:52]
- “Picture me at 16.” (Cuban shows a photo: 5'8", 30 pounds heavier than now.) [11:32]
On Self-Confidence and Work Ethic:
- “The one thing in life you can control is your effort. And so that’s just my style.” — Mark Cuban [12:44]
- “Most people don’t do the work. And so that's what gave me confidence because I knew I do the work prepared and that set me apart always.” — Mark Cuban [13:14]

The Power of Curiosity and Learning

(13:21–15:29):
- “Curiosity is one of the greatest business skills anybody can have.” — Mark Cuban [13:21]
- Cuban spends hours daily learning about new things (“four hours a day”).
- Journey into tech: Landed at a software store in Dallas, learned by reading manuals, taught himself to code and sell.
- No mentors: Cuban never had a mentor. Prefers learning by figuring things out himself.
  - “[Mentorship is] not that I don’t believe in them. To each their own. But...going through the process of figuring things out is a skill.” — Mark Cuban [15:40]

Access and Cold Emails: Mark Cuban’s Open Inbox

(16:21–18:38):
- He gets inundated with email requests—“my email is public.” — Mark Cuban [17:45]
- Instead of mentorship, he answers single, well-asked questions—otherwise, “I just hit the delete key. It takes me two seconds.” [18:11]
- “I’ve literally gotten emails where I’ve invested probably over a hundred million dollars from people I don’t know.” — Mark Cuban [18:21]
  - Notable Deals from Cold Emails:
    - Relativity Space: 3D printed rockets, now worth billions. Cuban gave $750K for ~20% (heavily diluted, “now worth...a whole lot of money”). [18:44–19:17]
    - Cost Plus Drugs: Co-founded after Dr. Ash Mayansko cold-emailed him.

Cost Plus Drugs: Disrupting Big Pharma

(19:19–26:00):
- Origin Story: Dr. Ash Mayansko, a radiologist and mathematician, cold-emailed Cuban with the idea for a compounding pharmacy to lower generic drug costs.
  - “He sends me an email...wanted to create a compounding pharmacy to make generic drugs that are often out of supply...I’m like well that's pretty cool, but that's too short sighted. We gotta do it for all generics.” — Mark Cuban [19:46]
- How It Works:
  - Full price transparency (“we tell you exactly what our cost is for any drug we sell”), only mark up is 15%, plus $3 pharmacy handling and $5 shipping.
  - Recent metrics: nearly 1,000 generic drugs, aiming for close to 2,000 by year-end.
  - Cost Plus Drugs now often beats not just full retail prices, but people’s insurance co-pays.
    - “We thought we were going to mainly deal with people without insurance, but...people with insurance, we’re more often than not cheaper than people’s co-pays.” — Mark Cuban [22:08]
- Broader Impact:
  - Study found just 77 drugs on Cost Plus could save Medicare $3.6 billion/year.
  - Commitment to sell all legally prescribable drugs, including those controversial in some states post-Roe v. Wade like certain birth control and mifepristone generics. [24:08]
- Business Model:
  - No ads, no membership, no hidden fees.
    - “You don’t have to pay a monthly fee, none of that stuff...just straight up. We take our cost plus 15%.” — Mark Cuban [25:33]
  - Exponential growth: “We’re way past what we thought would be two years in.” — Mark Cuban [25:53]

Notable Quotes & Memorable Moments

On Effort and Self-Improvement:
- “The one thing in life you can control is your effort.” — Mark Cuban [12:44]
On Learning:
- “Curiosity is one of the greatest business skills anybody can have.” — Mark Cuban [13:21]
On Investment Philosophy:
- “Product first, because you can have great people, but if it’s not going to sell, it’s not going to work.” — Mark Cuban [06:47]
On Cold Emails:
- “I’ve literally gotten emails where I’ve invested probably over a hundred million dollars from people I don’t know.” — Mark Cuban [18:21]
On Pharmaceutical Disruption:
- “In this country in 2022, we should never be in a position where you have to choose between your rent, your food and your medication.” — Mark Cuban [22:08]
On Cost Plus Drugs’ Promise:
- “You don’t have to pay a monthly fee, none of that stuff. You don’t need a card. It’s just straight up. We take our cost plus 15%.” — Mark Cuban [25:33]
On Business’s Rapid Growth:
- “We’re way past what we thought would be two years in.” — Mark Cuban [25:53]

Timestamps for Major Segments

01:58 — Mark’s core team size; Alyssa’s Healthy Cookies deep dive
06:41 — Cuban’s investment criteria
07:42-08:14 — Shark Tank pitch realities and deals
10:07-12:13 — Childhood hustling and self-confidence
13:14-15:29 — Curiosity, learning, and no mentors
16:21-18:38 — Cold emails and discovering game-changing investments
19:19-22:29 — The founding and model of Cost Plus Drugs
24:19-26:00 — Growth, expanded access, and still disrupting

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Episode 483: Mark Cuban's Cold Email Empire: How $750K Investments Turn Into Billion-Dollar Returns

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Summary

Habits and Hustle – Episode 483

Episode Overview

Key Discussion Points & Insights

Mark Cuban’s Lean Team and Breakfast Rituals

Investment Philosophy: Product First, People Second

Shark Tank Realities and Due Diligence

Team Dynamics Among Sharks

Cuban’s Personal Backstory: From Underdog to Billionaire

The Power of Curiosity and Learning

Access and Cold Emails: Mark Cuban’s Open Inbox

Cost Plus Drugs: Disrupting Big Pharma

Notable Quotes & Memorable Moments

Timestamps for Major Segments

Conclusion

Summary

Habits and Hustle – Episode 483

Episode Overview

Key Discussion Points & Insights

Mark Cuban’s Lean Team and Breakfast Rituals

Investment Philosophy: Product First, People Second

Shark Tank Realities and Due Diligence

Team Dynamics Among Sharks

Cuban’s Personal Backstory: From Underdog to Billionaire

The Power of Curiosity and Learning

Access and Cold Emails: Mark Cuban’s Open Inbox

Cost Plus Drugs: Disrupting Big Pharma

Notable Quotes & Memorable Moments

Timestamps for Major Segments

Conclusion