This is MoneyWise, a podcast where host Sam Parr is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored f...
From Startup to $40M Exit – And We’re Still Just Brothers
Most founders feel isolated after selling their company. Chris and David Sinkinson didn’t—because they had each other.
The brothers built and sold their startup, AppArmor, for $40 million. But unlike many founders who struggle with identity and purpose post-exit, they had a built-in support system: each other. With a 10-year age gap and complementary skills, they navigated the highs and lows of entrepreneurship as a team. And when they suddenly found themselves financially free, their brotherhood kept them from making reckless decisions—or jumping into the next venture too soon.
In this episode, Chris and David share how selling their company impacted their relationship, their investments, and their sense of purpose. We dive into:
Why going through a major exit alone can feel isolating—but they never did.
How their brotherly dynamic kept them from making bad financial decisions.
The identity crisis that followed the sale—and how they leaned on each other to navigate it.
Why they’re already thinking about their next venture, but with new priorities.
🔗 Check out their book and podcast at startupdifferent.com.
This is Moneywise, a podcast where host Sam Parr is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits.
Who is Harry Morton?
Harry Morton is the CEO of Lower Street, a company specializing in premium podcast production that he founded to transform brand narratives through audio storytelling. His expertise has made Lower Street a leader in the podcast industry, working with diverse clients from startups to Fortune 500 companies to enhance their market presence and audience engagement.
Who is Sam Parr?
Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022.
Check out Sam’s Companies:
Hampton
Sam’s List
This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.
Chapters:
The Big Exit: Details and Figures (01:38)
Managing Wealth Post-Exit (04:17)
Life Changes and Big Purchases (08:15)
Reflecting on the Exit and Future Plans (14:05)
Early Days and Starting a Business (17:39)
The Beginning of a Partnership (18:57)
David's Early Business Ventures (19:37)
The Birth of AppArmor (22:05)
Bootstrapping and Side Hustles (22:27)
Financial Strategies and Dividends (24:16)
Balancing Business and Personal Life (28:42)
Future Plans and Reflections (32:16)
Final Thoughts and Takeaways (38:07)
This podcast was produced in partnership with Lower Street and distributed by Morning Brew.
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43:12
Elon Musk's Acquisition Made Me $50M, But Fatherhood Redefined My Life
What if the key to success wasn’t grinding harder—but learning to let go?
Chris Bakke made 10s of millions selling two companies, including one to Elon Musk’s Twitter. But after years of chasing big wins, something changed: he had kids. And suddenly, the drive that once defined him wasn’t as important as being present for his family.
Chris started as a scrappy startup founder, building and selling multiple companies for over $50 million each. He worked directly with Elon, made bold investments, and built a net worth of $25 million (or 50 depending on how you value Twitter stock). But fatherhood led him to reevaluate everything—including his ambition in the tech world.
In this episode, Chris opens up about how becoming a dad reshaped his perspective on work, money, and happiness. We dive into:
Why having kids made him rethink the endless pursuit of success.
How he balances financial security with personal fulfillment.
The trade-offs of working with Elon Musk—and why he ultimately walked away.
Why he believes the multiple cashflowing agencies he runs make him better off than a highly valued illiquid tech company anyway.
This is Moneywise, a podcast where host Sam Parr is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits.
Who is Sam Parr?
Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022.
Check out Sam’s Companies:
Hampton
Sam’s List
This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.
Chapters:
Chris Bakke's Financial Breakdown (02:18)
Early Career and First Startup (08:16)
The Success of Lasky and Acquisition by Elon Musk (13:43)
Working with Elon Musk (18:16)
Family Life and Career Transition (20:24)
Balancing Family and High-Stakes Career (20:52)
Shifting Focus to Smaller Projects (22:29)
The Trade-Offs of Ambition (23:34)
Finding Joy in Simple Ventures (26:26)
Parenthood and Professional Ambition (27:54)
Lessons from Working with Elon (29:58)
The Impact of Wealth and Parenthood (36:49)
This podcast was produced in partnership with Lower Street and distributed by Morning Brew.
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46:02
$500M and Still Asking "What’s Next?": Peter Wokwicz’s Guide to Curiosity-Driven Success
What if chasing curiosity, not cash, was the key to a richer, more fulfilling life?
Peter Wokwicz turned his relentless curiosity into a $500 million fortune—and found happiness along the way.
Peter didn’t build his wealth by following the typical playbook. Instead of just chasing cash, he let his curiosity lead the way—and it’s resulted in over 40 successful exits, groundbreaking innovations, and a life that’s anything but boring. Now, with a thriving family office and a long list of projects, Peter spends his time doing what excites him most and making an impact in the process.
In this episode, Peter reveals how leaning into curiosity can create more fulfillment than any paycheck. We dive into:
Why passion, not profit, is his ultimate driver—and why chasing money alone will leave you empty.
How he uses his wealth to create a playground for innovation and exploration.
Why staying curious has helped him avoid burnout and find happiness in both work and life.
His take on “failing fast,” embracing risk, and why speed is his secret weapon.
This is Moneywise, a podcast where host Sam Parr is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits.
This interview was done by show-correspondant Andrew Namanny. You can listen to his podcast Permission to Shine here.
Who is Sam Parr?
Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022.
Check out Sam’s Companies:
Hampton
Sam’s List
This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.
Chapters:
Peter's Financial Overview (03:16)
Peter's Early Curiosity and Career (05:04)
The Value of Equity Over Cash (07:33)
Peter's Investment Strategy (10:10)
The Role of Velocity in Success (13:21)
Peter's First Big Exit (14:50)
Creating a Playground for Innovation (16:38)
The Family Office and Its Philosophy (19:21)
Embracing Failure and Innovation (20:52)
AI and Music Preferences (22:19)
Venom Labs: Medical Breakthroughs (23:21)
Team Structure and Incentives (24:38)
Blending Business with Personal Life (26:36)
Philosophy on Inheritance and Happiness (31:29)
Final Thoughts and Encouragement (34:42)
This podcast was produced in partnership with Lower Street and distributed by Morning Brew.
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41:23
MiniWise: Why Checking Your Portfolio Every Day Might Be Ruining Your Life
Are you obsessively checking your portfolio—or avoiding it entirely? What’s the right approach to managing your money post-exit?
In this Mini-Wise episode, Sam Parr breaks down how three ultra-wealthy entrepreneurs—Chuck (net worth: hundreds of millions), Travis (net worth: $50M), and Anne Mahlum (net worth: $100M+)—handle the mental rollercoaster of market fluctuations. Each shares their unique strategy, from completely logging off to obsessively staying informed, and how these choices impact their peace of mind and financial outcomes.
Chuck sold his company for $2.5 billion but realized his daily portfolio check-ins were ruining his mood, so he outsourced entirely. Travis stopped compulsively tracking his investments and focused on growing his next business instead. Meanwhile, Anne Mahlum embraces daily oversight, crediting her disciplined research and comfort with market dips as key to her 20%+ portfolio growth.
In this episode:
The emotional toll of tracking massive portfolios.
Why "logging off" works for some investors—but not all.
Anne Mahlum’s take on how staying informed helps her make bigger, smarter bets.
Learn how to match your investing strategy with your personality—and find the tools and habits that bring you both peace and success.
This is Moneywise, a podcast where host Sam Parr is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits.
Who is Sam Parr?
Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022.
Check out Sam’s Companies:
Hampton
Sam’s List
This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.
Chapters:
Introduction to Mini Wise (0:00)
The Emotional Rollercoaster of Portfolio Tracking (00:33)
Chuck's Story: Emotional Detachment from Investments (01:11)
Travis's Approach: Logging Off for Peace of Mind (02:36)
Anne's Strategy: Daily Monitoring and Research (05:05)
Conclusion and Final Thoughts (08:29)
This podcast was produced in partnership with Lower Street and distributed by Morning Brew.
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12:42
The $300 Million Exit That’s Funding Humanity’s Future with Bryan Johnson
Most people think Bryan Johnson just wants to live forever.
They’re wrong.
Bryan’s real goal is to leave a legacy that will last centuries.
In this episode, we uncover the extraordinary vision of Bryan Johnson, an entrepreneur driven by the audacious mission to earn the respect of people living in the year 2500.
Bryan isn’t just the man who sold Braintree (the parent company of Venmo) for $300 million—he’s an innovator investing every resource he has into shaping humanity’s future. From building a brain-interface company to launching Blueprint, a scientific health initiative, Bryan’s focus isn’t on today’s accolades. It’s on creating a legacy that will stand the test of time.
In this episode:
Discover how Bryan’s financial success stemmed from his quest for eternal relevance.
Learn how he allocates his wealth, including the risks he’s taken and the investments he regrets.
Hear about his frugal lifestyle, his thoughts on the true purpose of money, and why his mission shapes every financial decision he makes.
This is Moneywise, a podcast where host Sam Parr is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits.
Who is Sam Parr?
Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022.
Check out Sam’s Companies:
Hampton
Sam’s List
This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.
Chapters:
The Genesis of Braintree and Its Success (02:19)
Brian's Post-Exit Life and Investments (06:48)
The Quest for a Lasting Legacy (13:13)
Reflections on Time, Legacy, and Impact (18:23)
The 'Don't Die' Philosophy (24:28)
Financial Priorities and Frugality (26:02)
Blueprint and Health Achievements (27:20)
Reflections on Investments (29:45)
Historical Inspirations and Philosophies (35:46)
Final Thoughts and Legacy (41:01)
This podcast was produced in partnership with Lower Street and distributed by Morning Brew.
This is MoneyWise, a podcast where host Sam Parr is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups.
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