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This podcast has
24 episodes
Language
EnglishPublisher
Henrique DubugrasExplicit
Yes
Date created
2024/12/06
Latest episode
2025/12/18
Average duration
102 min.
Release period
15 days
Description
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.
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How Prosus CEO Builds Winning Tech Culture | Fabricio Bloisi
2025/12/18
When most founders chase a single idea, Fabricio Bloisi built 120.
The Brazilian entrepreneur is the CEO of Prosus, the founder of Movile, and the Chairman of iFood, and has helped shape companies that now reach billions across continents.
And the spark for all of it began with a teenage ambition “to create a very big global tech company.”
We also get into:
• Movile’s rise from near bankrupt moments to a global tech giant
• how confronting brutal facts became the cultural backbone of his companies
• what the U.S. still underestimates about competition abroad
• where Prosus is heading next with its large commerce model
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. Fabricio Bloisi- https://x.com/fabloisi
2. Brex- https://x.com/brexHQ
3. Henrique Dubugras- https://x.com/hdubugras
00:00 Trailer
01:42 The Early Days
08:34 Scaling and Innovating: The Food Journey
11:28 Balancing Innovation and Execution
30:07 The Rise of iFood: Dominating the Market
33:37 Transition to Prosus: A New Chapter
35:58 Prosus' Global Strategy and Vision
45:16 Challenges and Opportunities in Emerging Markets
Why Airwallex Is Betting Against SWIFT and Stripe | CEO Jack Zhang
2025/12/08
Jack Zhang landed in Melbourne at 15 with no money, no English, and no one to lean on.
By 30, he was turning down a billion-dollar offer from Stripe.
In this episode of HD in HD, I sit down with the co-founder and CEO of Airwallex to trace his zero-to-borderless journey—from small-town China to building one of the biggest tech stories ever to come out of Australia.
We get into:
• What Airwallex did differently that Stripe couldn’t in APAC
• The $100,000 mistake that nearly derailed their first client
• How Jack handled 2022’s valuation reset (and why he didn’t panic)
• The AI opportunity he thinks everyone is sleeping on
• how Airwallex hit $1B in volume before raising a proper Series A
00:00 Trailer
00:46 Introduction
01:18 Airwallex
04:58 No English from China to Australia
15:15 My first business, no financial support
23:06 All work, no fun
31:03 Development and coffee
36:26 Nothing is that hard
40:05 Startups
45:40 Brex
46:29 Starting Airwallex
53:27 The whole thing fell apart
57:20 Sequoia Capital and Tencent
1:05:41 Billion-dollar acquisition offer
1:11:59 Managing globally
1:16:20 Motivation and efficiency
1:23:26 Worth billions, hard to turn
1:24:58 Lessons from China
1:29:38 Outro
From Iranian Refugee to Uber CEO | Dara Khosrowshahi
2025/11/24
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.
How Max Levchin Built the System Behind 90% of U.S. E-Commerce
2025/11/10
“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/
How Deliveroo Got Acquired by Doordash for $3.9B | Will Shu
2025/10/31
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
How Alex Bouaziz Built Deel Into a $17B Giant | Alex Bouaziz & Deel
2025/10/16
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
How Adversity Made Him Unstoppable | Barry Diller
2025/10/06
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
How Kalshi Sued the U.S. Government and Won | CEO Tarek Mansour
2025/09/25
When regulators tried to shut them down, Tarek Mansour took them to court, and made history.
This week on HD in HD we're joined by the co-founder and CEO of Kalshi, the first fully regulated financial exchange for trading on events. He’s redefining how markets work by building a platform where people can trade on everything from elections to the economy, and proving that prediction markets can be both legitimate and transformative.
In this episode, we also get into:
why entrepreneurship has no clear destination, so you might as well enjoy the journey
how trading shaped how he thinks about risk and decision-making
how Kalshi survived its showdown with regulators
the bet that event trading can make humanity more rational
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:
Tarek Mansour- https://x.com/mansourtarek_?lang=en
Brex- https://x.com/brexHQ
Henrique Dubugras- https://x.com/hdubugras
This episode was produced and distributed by our friends at Atomik Growth: https://atomikgrowth.com/
00:00:00 Intro
00:01:13 Brex Sponsorship
00:02:11 Early Years in Lebanon
00:08:41 Success and Stress
00:29:23 Expected Outcomes and Variance
00:41:43 MIT Experience
00:45:59 Goldman Sachs
00:53:08 Y Combinator
01:00:48 Legal Challenges
01:08:14 Raising Funds
01:14:02 The Election Market Challenge
01:35:45 Winning the Lawsuit
01:40:25 Mainstream Success
01:44:01 The Role of Support Systems
Sebastian's Journey From Flipping Burgers → $17B+ IPO
2025/09/15
How do you go from pitching Sequoia to ringing the bell on a US IPO?
Sebastian Siemiatkowski, co-founder and CEO of Klarna was raised in a home where ambition met accountability. Even as Klarna thrived in Sweden, his parents reminded him: “That’s fantastic. When are you going to get your degree?”
That grounding, paired with Sebastian’s own ambition to measure up to companies like Google and Facebook, pushed Klarna beyond local success to a global stage.
In this episode, we also get into:
• how sci-fi books inspired him to see entrepreneurship as an adventure
• how Klarna brought Sequoia on board
• how Klarna got ahead of Afterpay in the U.S market
• navigating co-founder tensions and pivoting leadership
• turning Sweden’s strict bill collection into Klarna’s advantage
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. Sebastian Siemiatkowski- https://x.com/klarnaseb
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/
Chapters:
00:00 Intro
05:03 Background and Immigration
12:59 University Life
23:55 Gap Year Adventures
37:57 Finding Multiple Jobs
41:57 The Birth of Klarna
53:42 The First Product
01:15:32 Sequoia's Investment
01:34:50 Entering the US Market
01:49:01 AI and the Future
The $2B AI Startup Changing Content Forever | Victor Riparbelli
2025/08/22
Before founding Synthesia, Victor Riparbelli grew up in Denmark with parents who struck a balance between ensuring his future security and giving him the freedom to pursue his passions, with his father steering him toward technology.
At Stanford, the intense academics and ambitious peers challenged him to question the status quo and honed his approach to creating helpful tools.
We also get into:
• why complex video games were his first playground for building business
• how Mark Cuban became their first investor without meeting them
• why the future of communication is video
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. Victor Riparbelli- https://x.com/vriparbelli
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
How Vercel Saves Dev Teams $10M+ in Time | Guillermo Rauch
2025/07/21
Before founding Vercel, Guillermo Rauch, was a self-taught teenager in Argentina earning his first dollars online to help his family.
From early open-source work to remote freelancing, this episode traces how his drive to figure things out led to solving web performance at scale.
We also get into:
• how his dad instilled a mindset of pushing tech boundaries
• what growing up during Argentina’s economic swings taught him
• why he sees Minecraft as a healthy game for his kids
• why he believes speed without direction is meaningless
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. Guillermo Rauch- https://www.linkedin.com/in/rauchg/
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 Intro
02:00 Early Years
04:50 Parenting, First Experiences with Computers
07:40 Screen Time Rules
11:40 Video Games & Developing Programming Skills
15:30 Freelance Coding & Earning in U.S. Dollars
19:40 High School
24:10 Startup Offer
30:30 Silicon Valley & First Acquisition
41:45 Founding Vercel
54:40 AI Wave: v0, Agents & “Token Factories”
01:14:28 Vercel's Success and Client Impact
01:20:58 The Role of AI in Development
01:40:49 Iterating Towards Greatness
01:52:27 Balancing Luck and Skill
Betting on the Cloud Before it was Cool: The Rise of Box w/ Aaron Levie
2025/07/07
With an insatiable appetite for “what’s the new model,” Aaron Levie, Co-founder and CEO of Box, grew up chasing ideas without hesitation: performing magic at birthday parties, building websites, and making short films.
In this episode of HD in HD, he shares how a curious mind from early ages became his greatest strength, and how staying slightly uncomfortable kept him ahead of the biggest tech shifts, from SaaS to AI.
Today, Box powers content for 100k+ organizations and 68% of the Fortune 500, and is still driven by the same restless energy Aaron had as a teenager, always chasing what’s next.
In this episode, we also get into:
overcoming critical challenges when scaling storage capacity
the move that set Box apart from Dropbox
how AI is becoming the next major accelerator for Box
00:00 Intro
00:57 Brex Sponsorship
01:44 Aaron Levy's Early Years
02:24 High School
13:04 College
17:29 The Early Days of Box
23:17 Technological Shifts and Challenges
29:39 Navigating Competition
30:00 Enterprise Differentiation
32:24 Brex Sponsorship
33:12 AI’s Impact on Software and Work
44:51 AI's Role in Enterprise Knowledge Management
48:07 Future of Organizational Design
55:50 AI's Influence on Sales and Marketing
01:03:50 Reflections on Luck, Strategy, and Mistakes
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. Aaron Levie- https://www.linkedin.com/in/boxaaron/
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/
From $300M to $1B in Revenue: How Navan Scaled Travel Tech to 50+ Countries (Ariel Cohen)
2025/06/30
When Ariel Cohen, co-founder and CEO of Navan, first set out to modernize corporate travel, he wasn’t an industry insider.
What he did bring was a relentless focus on fundamentals, constantly asking, “Is it a good business?”, an instinct that arose from his family’s financial struggles, working in cafés, and participating in virtual business competitions in Israel.
And that is exactly what led him to build a travel tech giant.
In this episode, we also get into:
• why building a startup while raising kids gave Ariel motivation to do better.
• the supply chain problem in the travel industry.
• will AI replace travel agents in the near future?
• how Navan’s chatbot helps reduce customers’ travel expenses.
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, click here.
Connect with us here:
Ariel Cohen
Brex
Henrique Dubugras
This episode was produced and distributed by our friends at Atomik Growth: https://atomikgrowth.com/
How This Dropout Built a $3B Fintech Giant | André Street
2025/06/10
Before co-founding StoneCo, a $3.67B fintech giant, André Street was already thinking like a founder at the age of 14, skipping school not to rebel, but to build.
His teacher was life itself, learning discipline from Jiu-Jitsu, gaining “environment intelligence” from being robbed on Rio’s streets, and maturity from an import-export class with 50 year olds.
In this episode he joins Henrique Dubugras to unpack:
- why he never wanted to be CEO
- the prediction he made five years ahead that made StoneCo Brazil’s first independent credit card acquirer
- why prioritizing customers early on became the foundation of StoneCo’s business model
- the hiring mantra that built one of fintech’s tightest cultures
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 here:
1. StoneCo- https://x.com/SejaStone
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
The 10% Bet That Built a $12B Company | Howie Liu (Airtable)
2025/05/26
Howie Liu built Airtable into one of the most powerful no-code platforms in the world—used by over 450,000 companies and backed by everyone from Benchmark to Thrive to YC.
In this episode of HD in HD, I was joined by the founder and CEO of Airtable as he reelected on the unexpected turns that shaped his entrepreneurial path—from cold-pitching algo trading models at a college career fair, to building software that powers teams at scale.
In our conversation, we get into:
why Airtable took 2.5 years to launch—and why it was worth it
how a CRM for his personal contacts became his first YC-backed startup
what Salesforce taught him about B2B scale (and what it didn’t)
how he talked his way into a quant internship that disappeared overnight
the $0-to-financial freedom moment that let him finally think big
We only scratched the surface on the Airtable chapter, so don’t be surprised if there’s a part two.
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.
Connect with us:
1. Howie Liu– https://x.com/howietl
2. Henrique Dubugras– https://x.com/hdubugras
This episode was produced and distributed by our friends at Atomik Growth: https://atomikgrowth.com
00:00 Intro
01:20 Introducing Howie and Airtable
02:10 Early life and family
07:33 Early tech
14:13 Building Websites
32:18 Dreaming big
34:07 Middle-Class Entrepreneur Theory
35:55 High school
44:57 College applications
56:40 Duke University
1:05:10 High-paying jobs
1:07:10 Internships and early career
1:09:23 Neural networks and quant trading
1:16:10 New internship
1:22:02 First startup and lessons learned
1:34:22 The birth of Airtable
1:38:27 Outro
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