My First Million — $50M Poker Pro Shares His Best Advice for Founders

Podcast: My First Million
Host: Sam Parr & Sean Ogle (standing in for regular cohost Shaan Puri), Hubspot Media
Guest: Daniel Negreanu
Date: October 6, 2025

Episode Overview

In this episode, famed poker player Daniel Negreanu — with over $50 million in tournament earnings — unpacks the deep parallels between professional poker and entrepreneurship. The conversation, led by Sam Parr and Sean Ogle, explores topics like bankroll management, risk-taking, emotional intelligence, reading people, recovering from setbacks, and how to handle life’s winning and losing streaks. The episode is a blend of poker stories, personal anecdotes, and tactical advice for founders and ambitious professionals, focusing on mindset and psychology more than technical business or poker strategy.

Key Discussion Points & Insights

1. Why Poker and Business Are Deeply Connected

Poker is akin to running a small business: self-employed, self-motivated, and reliant on smart decision-making and investment.
- “You have to register as a small business anyway, right? You're just self-employed… you still have to make smart decisions, invest and look for plus EV situations.” (Daniel, 01:21)

2. How Poker Has Changed — Old School vs. New School

Poker personalities have shifted from charismatic, “gunslinger” types to data-driven, math-oriented players.
- “It used to be, I'd look at Sam and I'm like, yeah, Sam's full of it… Now people are doing what’s called… counting combinations.” (Daniel, 02:28)
- Reference to the legendary players like Doyle Brunson’s pre-computer days versus today’s methodical, technical analysis.

3. Early Inspirations & Defining Poker Moments

The guest discusses the “Chris Moneymaker effect” and the Rounders movie as watershed moments.
- “That’s a watershed moment in poker, right? Because it was the first time where some amateur guy… he ends up winning.” (Daniel, 05:28-05:57)

4. The Art & Science of Reading People

Everyone is born with natural instincts for reading others, but most stop trusting them as they grow up.
- “A little baby can look at their mother and get a sense when mama is happy or sad… We all born with that. What happens is, as we get older, we trust it less and less.” (Daniel, 08:18)
Daniel’s practice: Mall-watching and profiling strangers to hone his observations—applied both to poker and business.
- “I'd go to the mall… and I'd watch people walk by, and I'd get a sense of: who is this person?” (Daniel, 08:43)
Approach for catching liars: Look for patterns from previous lies, focus on body language (e.g., chewing gum), and be aware of overconfidence as a red flag for deception.
- “An over exuberance of confidence… is problematic… If you actually acknowledge both good and bad… that shows some honesty.” (Daniel, 11:17)
A useful negotiation tactic: Don’t appear desperate. Let the other person approach you first.
- “Desperate people, they front load the pitch too much… the best way is to play the long game. Don’t even make an ask.” (Daniel, 13:26)

5. Learning by Imitation—Building a “Superplayer”

Daniel’s unique approach: Each week, pick a winning player, try to emulate their style, and harvest their best traits for his own toolkit.
- “I would play with people and I'd see… the same guys are winning… I'm gonna sit like him. I'm going to put my chips like him… create this super player.” (Daniel, 14:46)

6. Body Language, Zoom Negotiations, and Social Reading

Body posture, eye contact, and “real” vs. “fake” smiles all matter. Awareness is highest when people are relaxed and outside rigid business contexts.
- “Best way to get reads on people is when they are relaxed… not during a business call… but at dinner, over drinks.” (Daniel, 16:49)
- “The eyes are very, very telling… And then, a smile… If you looked at 10 smiles… you’d be surprised how good you are at telling which are fake and which are real.” (Daniel, 18:52)

7. Foundation Stories — Building, Failing, and Risk Appetite

Early days as a pool player and reckless teenage gambler in Toronto evolved into disciplined risk management.
- “I was building up money… but I'm a teenager and I'm reckless… You got money, you lose it. The good news was… when I would go broke… I could borrow money from people…” (Daniel, 22:44)
As you succeed, risk management needs to become more conservative.
- “When you're taking risk, you take risk when you're on the low end of the totem pole… Once you've established, you should be way more risk averse.” (Daniel, 24:44)

Powerful Analogy

“If I had $500, I could go for broke. But once you have $2 million, you can’t risk that to go back to $500.” (Daniel, 24:44)

Similar business advice: Take your biggest swings early in your career/life when you can recover quickest.
- “When you have a small bankroll is when you want to take the most risk… you don’t actually have that much to lose.” (Sam, 25:25)

8. Persistence and Learning From Losses

Daniel hit rock bottom multiple times before succeeding. Poker, like business, is about endlessly refining yourself in response to setbacks.
- “I went to Vegas. I had $3,000… 24 hours later, I did not… It was a trial and error thing… But I had persistence… I understood that…” (Daniel, 27:56)
Memorable Quote:

“I was the sucker. They were only playing because of me. I was their EV… I remembered every one of their faces with vengeance, right? And I said, I'm gonna get you one day.” (Daniel, 27:56)

9. Danger of Chasing and Losing It All

Illustrative stories (e.g., Archie Karas): No matter how much you win, some lose it all through self-sabotage or lack of purpose.
- “He had $45 million, lost it all. Then he built up $17-18 million, lost it all.” (Daniel, 33:36)
Founder’s Note: Don’t let success breed complacency, and realize the “why” matters.
- “If you have a billion dollars… why do you care so much about a deal that made you $20 million…money is just a tool for…happiness. And what is happiness? It's not a bigger yacht… It's experiences.” (Daniel, 33:36)

10. What Motivates a Champion?

Money alone doesn’t drive Daniel; it’s about loving the game and striving for mastery.
- “I love competing… And when I started playing, I wasn’t playing for money. Money was a tool…” (Daniel, 36:22)
- “The truth is, my bank account, if it was 10x what it is now, my life wouldn't change much at all.” (Daniel, 36:22)

11. Degeneracy, Thrill-Seeking, and Managing Instincts

“All really just degenerate gamblers—we just found something we could beat.” (Quote of Doyle Brunson by Daniel, 38:37)
Daniel distinguishes himself from thrill-seekers: “I’m not really a thrill seeker... people say, ‘you should bungee jump.’ I have zero interest in that. Zero.” (Daniel, 39:35)

12. Respect for New Generation and Constantly Updating Skills

Daniel refuses to be the old guard who criticizes new poker styles; instead, he updates his “mental software” every 3–4 years.
- “The day you stop learning is the day everyone else starts to surpass you because they're going to continue to learn, and you're stuck here.” (Daniel, 75:39)

13. Coaching, Downswings, and Resilience

Common leaks for poker players—and business people—are psychological: quitting when winning, chasing when losing, getting stuck on a loss rather than process.
- “When they're losing, they're there for days… The biggest leak people make is they chase losses in the short run.” (Daniel, 45:31)
Best poker advice translates to entrepreneurship: handle adversity, focus on process, accept breakdowns as opportunities for breakthroughs.
- “The downswings are probably the most important part of…becoming a professional poker player. They call them a breakdown… Typically with a breakdown, things are going badly. That's an opportunity for a breakthrough.” (Daniel, 66:37)
Emotional resilience: “You’re not responsible for the weather… but you’re responsible for your response to it. The word 'responsible' is response able.” (Daniel, 54:29)

Relatable Story

“I get annoyed by the dumbest things… But I’ve learned to just, sort of, respond to positive, ignore the negative. But… it's silly, like you said, because why am I allowing this?” (Daniel, 59:35)

JK Rowling’s Quote on Rock Bottom

“Rock bottom became the solid foundation on which I rebuilt my life.” (Sam quoting Rowling, 68:06)

Notable Quotes & Moments

On Reading People:

“What you do with people is when they're lying, you want to remember what they look like when they're lying and look for that pattern again.” (Daniel, 08:43)
On Motivation:

“Money wasn't the end goal. Ultimately… what money provided me was… the freedom to be able to do whatever I want.” (Daniel, 36:22)
On Failure and Growth:

“Typically with a breakdown, things are going badly. That's an opportunity for a breakthrough… When things are going fine, right? You're probably not really delving that much into your strategy…” (Daniel, 66:37)
On Emotional Control:

“The difference between those that succeed and those that fail often are how they respond to things…” (Daniel, 54:29)
On Humility:

“It requires humility… Every three to four years, I'll update my own software, my mental software, by learning the things that they're learning…” (Daniel, 75:39)

Practical Founders’ Takeaways

Skill Acquisition: Steal like an artist—profile, observe, and imitate the best in your field. (14:46)
Negotiation & Pitching: Play the long game and avoid desperation; let the other side show interest first. (13:26)
Handling Loss: Treat downswings/breakdowns as learning moments for a breakthrough. Don’t chase losses physically or emotionally. (66:37)
Emotional Intelligence: Your response, not circumstances, determines your fate. Cultivate an internal locus of control. (54:29)
Stay Humble, Stay Curious: Regularly update your skills; never scoff at new approaches or youth. (75:39)
Define Your Motivations: Know your “why”—money is a tool, not the goal. (36:22)
Build Fortresses of Solitude: When winning big, lock in your base security; don’t gamble it all. (30:14)
Lead Yourself: If you constantly break promises to yourself, your confidence and self-image erode. (72:05)
Focus on Input, Not Outcome: Make good decisions; luck will even out. (43:54)

Timestamps for Key Segments

| Segment | Topic | Timestamp | |---------|-------------------------------|----------| | Intro | Why poker matters for business | 00:00–01:21 | | Poker’s evolution, “old school” vs “new school” | 01:39–04:56 | | Reading people—nature and nurture | 08:18–11:02 | | Tips for pitching and negotiation psychology | 13:26–14:30 | | On learning and copying from others | 14:46–16:13 | | Body language and social dynamics | 16:49–19:55 | | Early career, risk, and bankroll management | 22:44–25:25 | | Lessons from going broke & resilience | 27:56–30:14 | | Dangers of chasing and self-sabotage | 32:57–36:06 | | Motivation—what drives Daniel (not money) | 36:22 | | Humility & continued learning | 75:39 | | On emotional intelligence & coaching | 54:29–61:28 | | Handling adversity & downswings | 66:37–69:37 | | Content diet and "The Four Agreements" | 70:45–72:05 |

Conclusion

Daniel Negreanu goes far beyond poker strategy, offering listeners a masterclass in observation, emotional intelligence, resilience, and humility. His stories and frameworks are directly relatable to entrepreneurship and self-development: focus on the long game, handle downswings with introspection and growth, stay humble and update your mental “software,” and, most importantly, truly define what you seek in life—because “money is just a tool.” While poker is his vehicle, the principles resonate for anyone navigating the high-stakes tables of business or life.

My First Million — $50M Poker Pro Shares His Best Advice for Founders

Podcast: My First Million
Host: Sam Parr & Sean Ogle (standing in for regular cohost Shaan Puri), Hubspot Media
Guest: Daniel Negreanu
Date: October 6, 2025

Episode Overview

Key Discussion Points & Insights

1. Why Poker and Business Are Deeply Connected

Poker is akin to running a small business: self-employed, self-motivated, and reliant on smart decision-making and investment.
- “You have to register as a small business anyway, right? You're just self-employed… you still have to make smart decisions, invest and look for plus EV situations.” (Daniel, 01:21)

2. How Poker Has Changed — Old School vs. New School

Poker personalities have shifted from charismatic, “gunslinger” types to data-driven, math-oriented players.
- “It used to be, I'd look at Sam and I'm like, yeah, Sam's full of it… Now people are doing what’s called… counting combinations.” (Daniel, 02:28)
- Reference to the legendary players like Doyle Brunson’s pre-computer days versus today’s methodical, technical analysis.

3. Early Inspirations & Defining Poker Moments

The guest discusses the “Chris Moneymaker effect” and the Rounders movie as watershed moments.
- “That’s a watershed moment in poker, right? Because it was the first time where some amateur guy… he ends up winning.” (Daniel, 05:28-05:57)

4. The Art & Science of Reading People

Everyone is born with natural instincts for reading others, but most stop trusting them as they grow up.
- “A little baby can look at their mother and get a sense when mama is happy or sad… We all born with that. What happens is, as we get older, we trust it less and less.” (Daniel, 08:18)
Daniel’s practice: Mall-watching and profiling strangers to hone his observations—applied both to poker and business.
- “I'd go to the mall… and I'd watch people walk by, and I'd get a sense of: who is this person?” (Daniel, 08:43)
Approach for catching liars: Look for patterns from previous lies, focus on body language (e.g., chewing gum), and be aware of overconfidence as a red flag for deception.
- “An over exuberance of confidence… is problematic… If you actually acknowledge both good and bad… that shows some honesty.” (Daniel, 11:17)
A useful negotiation tactic: Don’t appear desperate. Let the other person approach you first.
- “Desperate people, they front load the pitch too much… the best way is to play the long game. Don’t even make an ask.” (Daniel, 13:26)

5. Learning by Imitation—Building a “Superplayer”

Daniel’s unique approach: Each week, pick a winning player, try to emulate their style, and harvest their best traits for his own toolkit.
- “I would play with people and I'd see… the same guys are winning… I'm gonna sit like him. I'm going to put my chips like him… create this super player.” (Daniel, 14:46)

6. Body Language, Zoom Negotiations, and Social Reading

Body posture, eye contact, and “real” vs. “fake” smiles all matter. Awareness is highest when people are relaxed and outside rigid business contexts.
- “Best way to get reads on people is when they are relaxed… not during a business call… but at dinner, over drinks.” (Daniel, 16:49)
- “The eyes are very, very telling… And then, a smile… If you looked at 10 smiles… you’d be surprised how good you are at telling which are fake and which are real.” (Daniel, 18:52)

7. Foundation Stories — Building, Failing, and Risk Appetite

Early days as a pool player and reckless teenage gambler in Toronto evolved into disciplined risk management.
- “I was building up money… but I'm a teenager and I'm reckless… You got money, you lose it. The good news was… when I would go broke… I could borrow money from people…” (Daniel, 22:44)
As you succeed, risk management needs to become more conservative.
- “When you're taking risk, you take risk when you're on the low end of the totem pole… Once you've established, you should be way more risk averse.” (Daniel, 24:44)

Powerful Analogy

“If I had $500, I could go for broke. But once you have $2 million, you can’t risk that to go back to $500.” (Daniel, 24:44)

Similar business advice: Take your biggest swings early in your career/life when you can recover quickest.
- “When you have a small bankroll is when you want to take the most risk… you don’t actually have that much to lose.” (Sam, 25:25)

8. Persistence and Learning From Losses

Daniel hit rock bottom multiple times before succeeding. Poker, like business, is about endlessly refining yourself in response to setbacks.
- “I went to Vegas. I had $3,000… 24 hours later, I did not… It was a trial and error thing… But I had persistence… I understood that…” (Daniel, 27:56)
Memorable Quote:

“I was the sucker. They were only playing because of me. I was their EV… I remembered every one of their faces with vengeance, right? And I said, I'm gonna get you one day.” (Daniel, 27:56)

9. Danger of Chasing and Losing It All

Illustrative stories (e.g., Archie Karas): No matter how much you win, some lose it all through self-sabotage or lack of purpose.
- “He had $45 million, lost it all. Then he built up $17-18 million, lost it all.” (Daniel, 33:36)
Founder’s Note: Don’t let success breed complacency, and realize the “why” matters.
- “If you have a billion dollars… why do you care so much about a deal that made you $20 million…money is just a tool for…happiness. And what is happiness? It's not a bigger yacht… It's experiences.” (Daniel, 33:36)

10. What Motivates a Champion?

Money alone doesn’t drive Daniel; it’s about loving the game and striving for mastery.
- “I love competing… And when I started playing, I wasn’t playing for money. Money was a tool…” (Daniel, 36:22)
- “The truth is, my bank account, if it was 10x what it is now, my life wouldn't change much at all.” (Daniel, 36:22)

11. Degeneracy, Thrill-Seeking, and Managing Instincts

“All really just degenerate gamblers—we just found something we could beat.” (Quote of Doyle Brunson by Daniel, 38:37)
Daniel distinguishes himself from thrill-seekers: “I’m not really a thrill seeker... people say, ‘you should bungee jump.’ I have zero interest in that. Zero.” (Daniel, 39:35)

12. Respect for New Generation and Constantly Updating Skills

Daniel refuses to be the old guard who criticizes new poker styles; instead, he updates his “mental software” every 3–4 years.
- “The day you stop learning is the day everyone else starts to surpass you because they're going to continue to learn, and you're stuck here.” (Daniel, 75:39)

13. Coaching, Downswings, and Resilience

Common leaks for poker players—and business people—are psychological: quitting when winning, chasing when losing, getting stuck on a loss rather than process.
- “When they're losing, they're there for days… The biggest leak people make is they chase losses in the short run.” (Daniel, 45:31)
Best poker advice translates to entrepreneurship: handle adversity, focus on process, accept breakdowns as opportunities for breakthroughs.
- “The downswings are probably the most important part of…becoming a professional poker player. They call them a breakdown… Typically with a breakdown, things are going badly. That's an opportunity for a breakthrough.” (Daniel, 66:37)
Emotional resilience: “You’re not responsible for the weather… but you’re responsible for your response to it. The word 'responsible' is response able.” (Daniel, 54:29)

Relatable Story

“I get annoyed by the dumbest things… But I’ve learned to just, sort of, respond to positive, ignore the negative. But… it's silly, like you said, because why am I allowing this?” (Daniel, 59:35)

JK Rowling’s Quote on Rock Bottom

“Rock bottom became the solid foundation on which I rebuilt my life.” (Sam quoting Rowling, 68:06)

Notable Quotes & Moments

On Reading People:

“What you do with people is when they're lying, you want to remember what they look like when they're lying and look for that pattern again.” (Daniel, 08:43)
On Motivation:

“Money wasn't the end goal. Ultimately… what money provided me was… the freedom to be able to do whatever I want.” (Daniel, 36:22)
On Failure and Growth:

“Typically with a breakdown, things are going badly. That's an opportunity for a breakthrough… When things are going fine, right? You're probably not really delving that much into your strategy…” (Daniel, 66:37)
On Emotional Control:

“The difference between those that succeed and those that fail often are how they respond to things…” (Daniel, 54:29)
On Humility:

“It requires humility… Every three to four years, I'll update my own software, my mental software, by learning the things that they're learning…” (Daniel, 75:39)

Practical Founders’ Takeaways

Skill Acquisition: Steal like an artist—profile, observe, and imitate the best in your field. (14:46)
Negotiation & Pitching: Play the long game and avoid desperation; let the other side show interest first. (13:26)
Handling Loss: Treat downswings/breakdowns as learning moments for a breakthrough. Don’t chase losses physically or emotionally. (66:37)
Emotional Intelligence: Your response, not circumstances, determines your fate. Cultivate an internal locus of control. (54:29)
Stay Humble, Stay Curious: Regularly update your skills; never scoff at new approaches or youth. (75:39)
Define Your Motivations: Know your “why”—money is a tool, not the goal. (36:22)
Build Fortresses of Solitude: When winning big, lock in your base security; don’t gamble it all. (30:14)
Lead Yourself: If you constantly break promises to yourself, your confidence and self-image erode. (72:05)
Focus on Input, Not Outcome: Make good decisions; luck will even out. (43:54)

$50M Poker Pro Shares His Best Advice For Founders

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Summary

My First Million — $50M Poker Pro Shares His Best Advice for Founders

Episode Overview

Key Discussion Points & Insights

1. Why Poker and Business Are Deeply Connected

2. How Poker Has Changed — Old School vs. New School

3. Early Inspirations & Defining Poker Moments

4. The Art & Science of Reading People

5. Learning by Imitation—Building a “Superplayer”

6. Body Language, Zoom Negotiations, and Social Reading

7. Foundation Stories — Building, Failing, and Risk Appetite

Powerful Analogy

8. Persistence and Learning From Losses

9. Danger of Chasing and Losing It All

10. What Motivates a Champion?

11. Degeneracy, Thrill-Seeking, and Managing Instincts

12. Respect for New Generation and Constantly Updating Skills

13. Coaching, Downswings, and Resilience

Relatable Story

JK Rowling’s Quote on Rock Bottom

Notable Quotes & Moments

Practical Founders’ Takeaways

Recommended Reading

Timestamps for Key Segments

Conclusion

Summary

My First Million — $50M Poker Pro Shares His Best Advice for Founders

Episode Overview

Key Discussion Points & Insights

1. Why Poker and Business Are Deeply Connected

2. How Poker Has Changed — Old School vs. New School

3. Early Inspirations & Defining Poker Moments

4. The Art & Science of Reading People

5. Learning by Imitation—Building a “Superplayer”

6. Body Language, Zoom Negotiations, and Social Reading

7. Foundation Stories — Building, Failing, and Risk Appetite

Powerful Analogy

8. Persistence and Learning From Losses

9. Danger of Chasing and Losing It All

10. What Motivates a Champion?

11. Degeneracy, Thrill-Seeking, and Managing Instincts

12. Respect for New Generation and Constantly Updating Skills

13. Coaching, Downswings, and Resilience

Relatable Story

JK Rowling’s Quote on Rock Bottom

Notable Quotes & Moments

Practical Founders’ Takeaways

Recommended Reading

Timestamps for Key Segments

Conclusion