Stop making million dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems: https://joinhampton.com/

Kass and Mike Lazerow built two companies together, sold one for $25M… and the next for $745M. Along the way, they went bankrupt, survived dot-com busts and Facebook booms, and figured out how to build a business without destroying their marriage.

Here’s what we talk about:

• What it’s actually like to sell your company for $745 million
• The early Golf.com bankruptcy scare, and how Tiger Woods saved the business
• Why their co-founder relationship works (and where it almost blew up entirely)
• Mixing work and love: the brutal fights, trust, and one-liners from the delivery room
• Full breakdown of their first splurge, and what “enough” money really means
• Raising $50M without meaning to sell, and getting a surprise offer from Salesforce
• The $12M flop that reminded Mike why Kass is the only co-founder he needs
• Co-founder red flags, communication rules, and how they manage disagreements
• Living rich vs. feeling rich: the moment they finally felt secure

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Kass and Mike https://kassandmike.com/
• Kass and Mike's book: Shoveling $h!t: A Love Story https://www.amazon.co.uk/Shoveling-Story-about-Entrepreneurs-Success/dp/B0DY21NS7W

Sponsors:

• The modern way to run your business phone is https://www.quo.com/perks/moneywise
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Chapters:

• (1:26) The $745M Buddy Media exit
• (4:29) What people get wrong about working with a spouse
• (6:22) How Kass and Mike met
• (8:44) The Golf.com story
• (15:33) Managing team dynamics as married co-founders
• (23:17) Handling finances as a married couple
• (28:18) What they did with the money after the exit
• (32:33) Lessons learned and what they'd do differently
• (36:58) Closing thoughts on finding the right co-founder

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Harry Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — http://www.joinhampton.com/exit-report

Jaclyn Johnson sold Create & Cultivate for $22 million. Then she hit pause – burned out, got divorced, and took a year off to figure out what she actually wanted. Now? She’s back, running the same company she sold, after buying it back for less.

Here’s what we talk about:

• Flipping real estate, investing in 25 startups, and turning $10K into $1.2M
• Spending $17K/month on rent – and not caring
• The number where she actually felt rich: $4–5M liquid
• Her full wealth breakdown: real estate, stocks, startups, and “a little” crypto
• Why angel investing works for her, and the returns that keep her going
• How burnout and divorce forced her to take a full year off
• What it’s like buying back the company you sold – for less
• Why she’ll never run day-to-day again (and how operators changed everything)
• Female founder scrutiny, and why being the face of the brand gets brutal
• Why she’s done chasing status, and how FOMO just disappeared

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Jaclyn Johnson https://jaclynrjohnson.com/

Sponsors:

• Get US caliber talent at offshore prices with https://www.oceanstalent.com/
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Chapters:

• (0:25) How Jacqueline Johnson built and sold businesses for millions
• (1:43) The three kinds of success every founder chases
• (7:04) What it actually feels like to have $15M in the bank
• (15:29) How Create & Cultivate became a brand women rally behind
• (18:37) The double standard: What it’s really like being a female CEO
• (23:18) The moments that made Jacqueline feel like she’d “made it”
• (25:37) What happens after you stop chasing FOMO
• (29:38) The money mistakes founders make after a big exit
• (32:04) What Jacqueline wishes every founder knew before selling

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Harry Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — https://www.joinhampton.com/exit-report

Jordan Schlipf spent a decade building companies optimized for fun, freedom, and friendships. But with years of hindsight, he wonders if he left too much money on the table.

Here’s what we talk about:

• Why Jordan left a lucrative investment banking path to chase startups
• How the Rainmaking model let him share risk (and reward) with fellow founders
• The downside of passion-led business: no investment thesis, millions wasted
• Why he believes he could’ve made way more money doing less exciting work
• What he thinks about his $4M liquid net worth — and why it doesn’t feel like enough
• The moment he realized private equity is a better game than startups
• How he’s now trying to turn around a $10M beauty business without raising capital
• What it really costs to live well in London as a founder with a family
• Why he regrets chasing the “cool” startup dream instead of playing it safe
• What true wealth means to him today: help, time, and optionality

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Jordan Schlipf https://www.linkedin.com/in/jordan-schlipf-0b855174

Sponsors:

• Tam your taxes today at https://olarry.com/
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Chapters:

• (0:49) Breaking Down the Rainmaking Model
• (2:08) Jordan’s Pivot from Investment Banking to Startups
• (4:15) Why He Couldn’t Stay Away from Startups
• (5:43) The Origins & Vision Behind Rainmaking
• (8:48) Biggest Challenges in the Rainmaking Model
• (10:57) Costly Mistakes & Lessons Learned Along the Way
• (13:00) Why Jordan Stepped Away from VC
• (17:05) Taking Over as CEO of a Beauty Brand
• (18:23) Jordan’s Current Finances & Where He Stands Today
• (20:23) Lifestyle Adjustments & Financial Struggles
• (24:32) Life Before Family vs. Life After
• (29:04) What He Wishes He’d Done Differently

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Harry Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — https://joinhampton.com/exit-report

Donald Spann built a multi-million dollar call center from scratch — with no outside capital, no technical background, and no safety net. Even crazier? He sold it for $12M to the first person who ever signed up.

Here’s what we talk about:

• Dropping out of college because he knew he’d never work for anyone else
• Building a cleaning business off a Reddit thread… then using it to launch something way bigger
• Accidentally going viral and getting 65,000 applications on a mom blog
• Why he’s never raised a dollar of capital — and never plans to
• His $12M exit from a bootstrapped call center (and how the buyer was his first-ever customer)
• Breaking down his finances: no real estate, no advisor, just stocks and angel bets
• Growing up Black in a private school bubble and how that shaped everything
• Living on $10K/month in Mexico and self-funding a new mezcal brand

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/

Sponsors:

• Tam your taxes today at https://olarry.com/
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Chapters:

• (1:26) Donald’s Net Worth & Current Ventures
• (3:57) Early Life, Education, and First Lessons
• (7:40) First Businesses & Getting Into Y Combinator
• (10:49) Building and Selling the Cleaning Business
• (14:02) The Successful Exit of Vicki Virtual
• (18:54) Personality, Confidence, and Entrepreneurial Edge
• (22:41) Meritocracy, Hard Work, and the Role of Luck
• (25:40) Reflections on Success & Personal Growth
• (29:02) Race, Identity, and the Entrepreneurial Journey

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Harry Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-report

Rajiv Khaneja made tens of millions running an ad tech company, but still lives in the same city he grew up in, wears the same clothes, and told friends he rented his house—even though he owned it. Here’s why.

Here’s what we talk about:

• How Rajiv built a profitable tech business as a teenager (and hired adults while still in high school)
• Turning down a $2.5M acquisition offer... then heading back to chemistry class
• What 25 years of “anti-lifestyle inflation” looks like
• The impact of immigrant parents and a “worst-case-scenario” money mindset
• Why he lived undercover for years, and how finding a peer group unlocked everything
• How he built AdButler into an 8-figure, bootstrapped business
• Rajiv’s idea of a lifestyle upgrade: attentional freedom > private jets
• Happiness optimization: spending $7M on a home to be closer to friends
• His new obsession: using AI to help cure cancer
• Co-founding Arvita Therapeutics — and why he’s still building, even with $50M+ in net worth

Sponsors:

• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• AdButler https://www.adbutler.com/index.html
• Arvita Therapeutics https://www.arvita.co/
  
  

Chapters:

• (0:00) Teen Millionaire: How Rajiv Made His First Money
• (0:45) Living Cheap on Purpose: Why He Drives a Prius
• (1:59) Managing Wealth & Long-Term Investing Strategy
• (3:36) Monthly Spending Breakdown & Frugal Habits
• (9:02) The Origin Story: From Web Polls to Ad Butler
• (19:16) Family, Upbringing & Money Values
• (24:49) Social Life, Hiding Wealth & Finding Founder Friends
• (31:56) Resisting Lifestyle Upgrades After a Big Exit
• (35:40) Choosing the Right Life & Business Partner
• (41:29) Future Bets: Biotech, Longevity & Playing the Long Game

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Harry Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-report

Ali Abdaal didn’t sell a startup. He didn’t raise money. He didn’t even plan to leave medicine. He just turned himself into the business, and ended up happier, wealthier, and more free than he ever expected.

Here’s what we talk about:

• Why Ali says money hasn’t made him more happy, just removed the stuff that made him unhappy
• His net worth (between $1M and $10M) and how it breaks down
• How a scammed MacBook deal sparked a business that made £1M+
• What he learned after hitting $6M/year in revenue, and why he stopped trying to scale further
• How flying business class and skipping trash day became his personal luxuries
• Why “$100M in the bank” wouldn’t change how he spends his time
• How coaching, meditation, and philosophy reshaped his relationship with money
• The moment Lewis Howes helped him break his identity as a doctor
• His rule of thumb: “Freedom comes from leaving money on the table”
• Why he's building software to reduce his dependence on content
• His real goal: $2M/year profit so he can work when he wants, on what he wants

Sponsors:

• Get US caliber talent at offshore prices with https://www.oceanstalent.com/
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Ali’s stuff: https://aliabdaal.com/

Chapters:

• (0:00) Introduction & Ali's Philosophy on Wealth
• (1:48) Net Worth Breakdown & Investing
• (3:17) Life in Hong Kong: Renting vs. Owning
• (4:54) From Medicine to Entrepreneurship
• (6:09) Early Business Lessons & Getting Scammed
• (7:44) Building and Selling the First Business
• (9:02) YouTube Journey & Passive Income
• (12:00) Revenue Growth, Plateau, and Lifestyle Design
• (16:01) Money, Happiness, and Scarcity Mindset
• (24:00) Motivation, Fulfillment, and Final Thoughts

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Harry Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-report

Rob Townsend says you’re wrong about financial advisors… mostly. And he’s built an 8-figure firm to prove it.

Here’s what we talk about:

• Why $3M liquid is Rob’s version of “f*** you money”
• How he went from $0 to 8 figures by modernizing financial planning
• Why the old guard of wealth management is failing founders
• What most people get wrong about index funds
• The simple investing mistake that wipes out 44% of stocks
• Why the happiest clients aren’t the richest ones
• How sabbaticals change Rob’s life (and business) every time
• His full portfolio: Dimensional Funds + a little Bitcoin
• The real reason private deals feel better than they perform
• The toxic mindset that plagues people with $25M+ net worth

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
  
  

Sponsors:

• The best phone system for teams at http://www.openphone.com/moneywise
• Achieve your dream body with https://www.dailybodycoach.com/moneywise

Chapters:

• The Financial Advisor Debate (00:00)
• Rob’s Personal Money Story (00:43)
• Growing Up & Early Influences (01:53)
• Lessons from Rob’s Uncle (05:39)
• Breaking into Wealth Management (06:31)
• Mistakes in Investing & Learning the Basics (09:01)
• The Case for Financial Planning (14:15)
• Building a Modern Wealth Firm (15:26)
• The Defense of Financial Advisors (19:14)
• Psychology of Wealth & Happiness (37:53)
• Final Thoughts: Money as a Tool for Life (45:53)

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

Your Host: Harry Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-report

Everything you need to know about turning art into a real (and risky) investment strategy.

Carlos Cardenas is a Private Wealth Advisor at Austin Wealth Management, bringing over 20 years of experience in alternative asset management. His background spans commercial real estate, technology, and healthcare ... but with a particular passion and expertise for the most alternative of asset classes: the fine art market.

Carlos spent nearly two decades in Paris, where he worked as a private art dealer and advisor, collaborating with leading institutions like Christie’s,

Sotheby’s, and the Picasso Family Office. His rare blend of financial acumen and art world savvy allows him to help clients navigate both traditional and nontraditional investments with insight and creativity.

Here’s what we talk about:

• What makes a banana duct-taped to a wall worth $6 million — and what it says about the art market.
• Carlos Cardenas shares how he went from private art dealer in Paris to advising wealthy clients on fine art investing.
• Why art can offer 8–12% returns — but only in a narrow slice of the market.
• How to start investing in art (even with less than $10K) — and when it becomes a serious wealth play.
• The real reason most people lose money in art — and how to avoid rookie mistakes.
• Passion, status, and profit: the three reasons people buy art (and why you need all three to succeed).
• Inside the elite world of art fairs, private dinners, and collector circles — and why art collecting is a powerful networking tool.
• Fractional ownership, tax loopholes, art-backed loans, and other financial hacks of the ultra-wealthy.
• How NFTs and digital authentication could transform the future of art investing.
• Why collecting art might just be the emotional outlet you didn’t know your money needed.

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Austin Wealth Management https://austinwealthmgmt.com/
• Carlos's LinkedIn https://www.linkedin.com/in/carloscardenastx/
• Carlos's Instagram https://www.instagram.com/chicobeef/?hl=en

Sponsors:

• Get US caliber talent at offshore prices with https://www.oceanstalent.com/
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Thinking of selling your company? Don’t leave millions on the table check out https://www.promissory.com/moneywise

Chapters:

• The $6.2 Million Banana & Art Market Hype (00:00)
• The Story of Art Collector Eli Saka (01:27)
• Meet Carlos Cardenas: Art, Wealth, and Passion (03:22)
• Art as an Investment: Returns & Blue Chip Art (04:44)
• Building an Art Collection & Diversification (07:06)
• Why Most Art Investments Don’t Pay Off (09:36)
• Reducing Risk & The Importance of Provenance (12:15)
• Big Wins, Big Losses, and Market Speculation (18:19)
• Fractional Ownership, Masterworks, and Modern Strategies (22:44)
• The Emotional Value of Art & Is It Worth It? (30:23)

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

This podcast is for educational purposes only and do not constitute financial advice.

You Host - Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.