From Iranian Refugee to Uber CEO | Dara Khosrowshahi
When Uber needed a reset, only a disciplined leader could see the path forward.
Raised in one of Iran’s leading industrial families, Dara Khosrowshahi watched everything disappear during the revolution as his family rebuilt their lives in the U.S.
In this episode, he shares how, with education as the only constant, he rose to become the youngest VP at Allen & Co., played a defining role across IAC and Expedia, and ultimately led Uber from deep losses to a profitable business.
We also get into:
the immigrant childhood that trained him to adapt faster
why betting on people, not models, became the most important lesson of his career
the early failures at Expedia that hardened his decision making and leadership style
how he rebuilt culture at Uber while operating under intense public scrutiny
the long term vision of turning Uber from a rides company into a real time logistics network
ABOUT US:
We’re proudly sponsored by Brex—a brand I co-founded, now supporting over 30,000 businesses like Anthropic, DoorDash, and Scale AI, helping them make every dollar count.
I’m grateful for their continued support as I bring you all conversations with some of the most exceptional founders of our generation. For more information, please go to: https://www.brex.com/?ref_code=bmk_audio_HDinHD
Connect with us here:
1. Dara Khosrowshahi- https://x.com/dkhos
2. Brex- https://x.com/brexHQ
3. Henrique Dubugras- https://x.com/hdubugras
This episode was produced and distributed by our friends at Atomik Growth.
--------
1:29:11
--------
1:29:11
How Max Levchin Built the System Behind 90% of U.S. E-Commerce
“Don’t just believe that things work, actually find out how they work and ask the question, can they work better?”
This has been Max Levchin’s constant pursuit since childhood, leading him to build PayPal, HVF, and Affirm, a perfect example of where engineering meets entrepreneurship.
In this episode, we explore what it takes to begin again after success and how Max Levchin’s relentless pursuit of optimization has defined two decades of fintech innovation.
We also get into:
• how a cryptography thesis became a fintech revolution, PayPal
• the psychology of merging with Elon Musk’s X.com
• why founders are idealists and investors are cynics
• how Max measures success in human lives improved
• and how America’s entrepreneurial DNA became its greatest competitive advantage
This episode was recorded on October 24th, 2025.
00:00 Intro
12:28 The PayPal Story
32:30 Founder CEOs vs. Hired CEOs
43:49 Entrepreneurship
48:47 The Media Industry
55:53 Credit Card Debt in the US
01:06:03 Affirm's Business Model
01:09:01 Challenges and Ethics in Lending
01:24:31 AI and Underwriting Models
01:32:51 Crypto and Stablecoins
01:46:26 Closing Remarks
ABOUT US:
We’re proudly sponsored by Brex—a brand I co-founded, now supporting over 30,000 businesses like Anthropic, DoorDash, and Scale AI, helping them make every dollar count.
I’m grateful for their continued support as I bring you all conversations with some of the most exceptional founders of our generation. For more information, please go to: https://www.brex.com/?ref_code=bmk_audio_HDinHD
Connect with us here:
1. Max Levchin- https://x.com/mlevchin
2. Brex- https://x.com/brexHQ
3. Henrique Dubugras- https://x.com/hdubugrasThis episode was produced and distributed by our friends at Atomik Growth: https://atomikgrowth.com/
--------
1:46:56
--------
1:46:56
How Deliveroo Got Acquired by Doordash for $3.9B | Will Shu
In a city built on great food, workers were still eating whatever was quickest.
When Will Shu moved to London, he felt that disconnect firsthand and built Deliveroo to bridge it, transforming a local gap into a network spanning 10 markets.
On this episode of HD in HD, Will shares how his belief in hard work and delayed reward helped him build Deliveroo into a global logistics leader, acquired by DoorDash for $3.9B.
We also get into:
• how they learned to manage riders, restaurants, and regulations
• how Deliveroo stood apart from competitors like Uber
• what Will believes DoorDash and Deliveroo can learn from each other post-acquisition
ABOUT US:
We’re proudly sponsored by Brex—a brand I co-founded, now supporting over 30,000 businesses like Anthropic, DoorDash, and Scale AI, helping them make every dollar count.
I’m grateful for their continued support as I bring you all conversations with some of the most exceptional founders of our generation. For more information, please go to: https://www.brex.com/?ref_code=bmk_audio_HDinHD
Connect with us here:
1. Will Shu- https://x.com/WillShuRoo
2. Brex- https://x.com/brexHQ
3. Henrique Dubugras- https://x.com/hdubugras
This episode was produced and distributed by our friends at Atomik Growth.
00:00 Intro
25:43 Will Shu's Early Life and Education
32:15 College Life and Career Beginnings
39:26 Wall Street Culture
46:15 The Birth of Deliveroo
01:04:58 Raising Funds
01:16:49 COVID-19
01:23:01 IPO and Market Reactions
01:36:54 AI and Future of Delivery
--------
1:48:38
--------
1:48:38
How Alex Bouaziz Built Deel Into a $17B Giant | Alex Bouaziz & Deel
Global payroll is a maze most companies dread navigating.
Deel turned it into their MOAT by streamlining HR across borders, powering remote work, and hitting a $1B+ run rate with over 5,000 employees.
Alex Bouaziz, Deel’s CEO and co-founder, grew up nerding out on Nintendo and hunted perfection from Paris to MIT. His relentless curiosity built a platform that’s rewriting how the world hires.
In this episode, we explore:
• why he wakes up obsessed with your problems, not his product
• how a Disneyland obsession shaped his entrepreneurial spark
• why he’s doubling down on AI and stablecoins
ABOUT US:
We’re proudly sponsored by Brex—a brand I co-founded, now supporting over 30,000 businesses like Anthropic, DoorDash, and Scale AI, helping them make every dollar count.
I’m grateful for their continued support as I bring you all conversations with some of the most exceptional founders of our generation. Onward and upward, together.
Connect with us:
1. Deel - https://x.com/deel
2. Brex - https://x.com/brexHQ
3. Henrique Dubugras- https://x.com/hdubugras
This episode was produced and distributed by our friends at Atomik Growth: https://atomikgrowth.com/
00:00 Introduction
01:35 Being happy
02:50 Big family
11:56 Video games and math
14:59 Confidence
16:12 College and older people
23:47 America, Nintendo, Disney
26:08 MIT
26:59 Helping yourself, cold emails
31:51 PhDs are super lonely
34:38 Trying to impress
39:16 Brex
40:06 Deel
45:05 Gaming forums and money struggles
49:49 San Francisco, Tel Aviv, Paris
52:26 Remote work
54:32 Growth and value
1:00:42 Marketing and getting old
1:02:09 Next decade
1:04:07 Crypto
1:08:42 AI and payroll
1:12:00 Outro
--------
1:12:49
--------
1:12:49
How Adversity Made Him Unstoppable | Barry Diller
How does someone with zero ambition rise to the top of Hollywood?
Barry Diller started out as a ‘wayward’ kid with no plan, then took his first big risk in television by producing original TV movies, a gamble no one in Hollywood thought would work.
In this episode, he shares how trusting his instincts and defying convention guided his journey from transforming Paramount to launching Fox Broadcasting Company and building IAC, now home to 10 publicly traded companies, leaving a lasting legacy.
We also get into:
• why adversity is the greatest training ground for instinct
• what it took to launch Fox Broadcasting against three dominant networks
• why sequels ruined Hollywood’s creative edge
• spotting screen interactivity before the internet took over
ABOUT US:
We’re proudly sponsored by Brex—a brand I co-founded, now supporting over 30,000 businesses like Anthropic, DoorDash, and Scale AI, helping them make every dollar count.
I’m grateful for their continued support as I bring you all conversations with some of the most exceptional founders of our generation. For more information, please go to: https://www.brex.com/?ref_code=bmk_audio_HDinHD
Connect with us here:
1. Brex- https://x.com/brexHQ
2. Henrique Dubugras- https://x.com/hdubugras
This episode was produced and distributed by our friends at Atomik Growth.
00:00 Intro
02:12 Barry Diller's Early Life
15:12 The ABC Network
25:30 Charles Bluhdorn
33:26 From TV to Paramount
42:34 Fox Broadcasting and Media Ventures
48:53 E-Commerce and Building IAC
59:07 Expedia
Henrique Dubugras founded fintech giant Brex when he was twenty-one years old. In his journey from São Paulo to Stanford to the heights of Silicon Valley he made connections with some of the biggest names in the ecosystem. Now, they’re not just business connections, but friends.