Asking Millionaire Homeowners How They Got Rich

SUMMARY

James Jani of School of Hard Knocks interviews millionaire homeowners in Long Island, New York, uncovering their entrepreneurial journeys, business strategies, and advice for building wealth from humble beginnings.

STATEMENTS

Sergio started his internet advertising company from his basement with no money, as a typical immigrant story from Spanish parents.
Sergio sold his company to Blackstone twice, first for around $200 million, and bought it back to continue growing it.
Sergio's company is now worth $300 to $500 million, and he remains motivated at age 53 to scale it further.
The driving factor for Sergio was seeing a company collect $100 million from a program he helped build but only receiving a $10,000 check, prompting him to start his own venture.
Internet advertising appealed to Sergio because it leveled the playing field, similar to AI today where early adopters gain an advantage.
Sergio uses AI every day for productivity, insights, and data collection, predicting major world changes in three years.
For business owners, Sergio advises using AI to automate repetitive tasks, freeing time for critical thinking.
Sergio faced doubt from his father during the 2008 crash, who suggested quitting, but persevered by competing against big companies through responsiveness.
Private equity often ruins acquired companies by forgetting the employees and founder's mentality, according to Sergio.
Sergio emphasizes running any company like a startup, maintaining founder spirit regardless of size.
Sergio's final message to the younger generation is to believe in yourself and break down big goals into small steps.
Entity structure like an LLC is crucial for protection and legal compliance, as Sergio learned after starting without one.
Teddy Hagerty sells humanoid robots and has sold more than anyone worldwide, on track for $100 million this year at age 30.
Teddy started with a drone photography business in high school, transitioning to robotics four years ago.
Not everyone is built for entrepreneurship; it requires patience and longevity, as fast money doesn't last, per Teddy.
Teddy's secret to scaling from $1 million to nearly $100 million involved leveraging AI trends in robotics without chasing fads.
Teddy blew money early on by building a fast life at 24 as a millionaire, learning patience is key.
Investing in yourself means trying, failing, and learning more from real business than school, says Teddy.
Teddy's life-changing book is "Ego is the Enemy" by Ryan Holiday, which helped neutralize his ego after early successes.
Ego can mislead young successes into thinking they're invincible, but reality shows many levels to achievement, as Teddy experienced.
Teddy's message: Don't give up, as business has ups and downs, and persistence keeps you in the game.
Joe DiRenzo built a $300-500 million swimwear company over 60 years, starting with $12,500 from his savings as an Italian immigrant.
Joe's parents were not wealthy; he grew up in Brooklyn and faced ridicule for starting his business with a wife and child.
Focus on a niche need in the industry, like high-end swimwear and competitive gear, was key to Joe's success.
Joe never feared big competitors, even losing money in the first year, and believed they wouldn't go out of business.
To preserve generational wealth, Joe uses trusts and teaches his family to manage money, live within means, care for employees, and control costs.
Joe's core principle: Keep your word with a handshake, being honest and truthful in all deals, as with his Asian partners.
Scott Baron started his construction business in 1999 with a borrowed $30,000 pickup truck and tools, from Queens with no family money.
During the 2008 crisis, Scott gambled everything to acquire property, leading to his first big win in hotels and then charter schools.
Scott's business now does $100-150 million annually, owning 3 million square feet of real estate worth $600-700 million with partners.
Scott wakes up laughing at his unexpected success, then employs "Viking brain" to hustle daily, loving what he does.
Entering the charter school market by chance with an empty building led to 21 schools and 10,000 students.
Reputation and keeping your word are paramount; one bad deal makes you a "sucker" forever, per Scott's father's advice.
Scott verifies trust through homework, never screwing others over, even if they've tried with him.
Scott's real estate scaling secret: Sense of urgency—constant action without delay.
Young hustle is returning in America after a lost generation, as Scott observes in his kids and their peers.
Patience and method: Like the old bull story, walk down the hill to achieve more sustainably.
Scott's message: Don't sell assets; hold and stay in the game for long-term gains.

IDEAS

Wealthy individuals seek privacy in gated Long Island enclaves, abandoning Manhattan penthouses for land and seclusion once fortunes hit eight figures.
Starting a business without knowing basics like LLCs is possible, but proper entity structure protects personal assets and enables scaling.
Immigrant backgrounds often fuel relentless drive, turning zero capital into multi-hundred-million-dollar empires through sheer perseverance.
Early exposure to industry giants' profits can ignite entrepreneurship, as seeing $100 million collected but earning only $10,000 prompted independence.
Emerging tech like the internet or AI creates equal-opportunity fields where savvy early users outpace incumbents without advantages.
AI will revolutionize productivity and data insights within three years, but its true power lies in automating monotony to amplify human creativity.
During economic crashes, doubters like family may push quitting, yet responsive, hands-on service against bloated competitors wins big contracts.
Buying back a sold company restores founder energy, preventing private equity's dilution of employee-driven innovation.
Motivation persists post-$200 million exit because stopping feels premature; dissatisfaction drives tempered ambition without losing spark.
Robotics as AI hardware allows riding tech waves without inventing trends, scaling from niche drones to global humanoid leadership in four years.
Patience defines true entrepreneurship over rushed "fast money" schemes, which collapse; longevity builds enduring brands from small scales.
Early millionaire status tempts lavish lifestyles, but building sustainably reveals life's longer timeline, avoiding Mike Tyson-like blowouts.
Failing fast in small ventures teaches more than formal education, turning "wasted" money into invaluable lessons on business realities.
Ego inflates young successes, blinding to higher achievement levels; books like "Ego is the Enemy" restore neutral, realistic headspace.
Business volatility means down days precede breakthroughs; persistence ensures you're positioned for life-changing ups.
Niche mastery in overlooked industries like swimwear yields half-billion-dollar valuations, even against giants, through unwavering belief.
Generational wealth endures via trusts, frugal management, employee loyalty, and crisis control, balancing enjoyment with protection.
Handshake deals with global partners thrive on unyielding honesty, outlasting contracts in trust-based production.
Crises like 2008 reward bold gambles on undervalued assets, pivoting from contracting to owning hotels and schools for nine-figure revenues.
Daily "Viking brain" mindset—hustling like survival depends on it—turns work into passion, even after financial independence.
Charter school voids offer scalable impact, housing 10,000 kids in 21 buildings from one serendipitous empty property.
One ethical lapse defines a reputation forever; building thousands of bridges means nothing if you "suck" even once.
Real estate empires grow through relentless urgency, amassing 3 million square feet by never postponing action.
America's youth are reclaiming hunger post-lost decade, signaling a hustle renaissance observable in personal circles.
Methodical patience scales impact: Walk to conquer all, rather than sprinting for one quick win.
Holding assets long-term trumps cashing out; patience in real estate and business keeps compounding wealth.

INSIGHTS

True wealth begins with identifying unmet needs in any industry and dominating niches through focused, fearless execution, regardless of starting capital.
Technology waves like AI and the internet democratize opportunity, rewarding those who automate routines to focus on strategic human ingenuity.
Perseverance amid doubt and crises defines entrepreneurs, as family skepticism and economic downturns test but ultimately forge resilient empires.
Maintaining founder mentality post-growth or acquisition preserves innovation, avoiding the pitfalls of bureaucratic private equity takeovers.
Ambition's dissatisfaction is a double-edged drive: It fuels endless scaling but requires balance to sustain personal fulfillment without burnout.
Longevity in business stems from patient brand-building over quick flips, leveraging trends sustainably for exponential, lasting growth.
Early financial windfalls demand disciplined patience; rushing lavish lives erodes fortunes, while measured investing in self compounds wisdom.
Ego unchecked derails young achievers, but reflective tools like philosophy books recalibrate perspective, revealing deeper success layers.
Volatility is entrepreneurship's norm—enduring lows positions for highs, turning persistence into inevitable breakthroughs.
Generational wealth safeguards through structured trusts and instilled frugality ensure legacy, prioritizing protection over unchecked indulgence.
Integrity as currency: Handshakes and reputation build unbreakable networks, far outlasting formal agreements in global dealings.
Bold risks in undervalued markets during turmoil create pivots to high-impact sectors, like from construction to education infrastructure.
Urgency without procrastination accelerates portfolios, but methodical planning ensures sustainable conquests over impulsive gains.
Societal hunger cycles evolve; recognizing resurgent youth drive signals prime times for mentorship and collaborative ventures.
Asset retention embodies patience's power: Holding through fluctuations maximizes compounding, keeping players in wealth's long game.
Serendipity meets preparation in market voids, where empty assets spark scalable, purpose-driven expansions like educational networks.
Ethical consistency defines legacy: One betrayal overshadows volumes of excellence, making trustworthiness the ultimate business moat.
Daily survival mindset transforms obligation into obsession, fueling passion that outlives necessity in high-stakes pursuits.

QUOTES

"I'm doing this on my own."
"AI should be used for every single thing that requires monotonous work, things that you're doing all the time that are repetitive."
"Fast money never lasts. And if you keep building and be patient, that's what a real entrepreneur is, is it's longevity and endurance."
"Invest in yourself. And that means even just like trying and failing. Like start a business, fail cuz you're going to learn so much about it."
"Ego is the Enemy... was a great way to start pushing my head space to a much more like neutral space."
"You can go out in the world, be a great builder, build a thousand bridges known far and wide everywhere in the world. You suck one, you be a sucker for the rest of your life."
"Sense of urgency. Constant pedal to the metal no matter what. Don't ever put off to tomorrow what you can do today."
"Young bull turns to the old bull and goes, 'Let's run down there. Screw one of those cows.' Old bull goes, 'Let's walk down. Screw them all.'"
"Don't sell. Hold. When it comes to real estate, when it comes to anything else, hold. Be patient."
"Hunger is back in America."

HABITS

Wake up every morning and go to work daily, even at 81, treating business as a non-negotiable routine.
Use AI every waking moment for productivity, automating repetitive tasks to focus on critical thinking.
Listen to audiobooks constantly, prioritizing personal development through audible resources like philosophy texts.
Maintain a "Viking brain" mindset: Start each day with urgency, hustling as if survival depends on it.
Verify all partnerships through thorough homework, building trust methodically without blind faith.
Manage money frugally: Live within means, vacation responsibly, and protect assets via trusts.
Keep your word with handshakes, fostering honest dealings in all professional interactions.

FACTS

Long Island hosts some of America's richest in private, gated communities, where billionaires seek seclusion from urban visibility.
Blackstone acquired Sergio's internet advertising firm twice, valuing it at $200 million initially, now $300-500 million.
Teddy's robotics company sold more humanoid robots worldwide than any competitor, scaling to $100 million revenue in four years from drones.
Joe's swimwear empire, started 60 years ago with $12,500, generates $30-50 million annually and is worth $300-500 million.
Scott's firm builds 21 charter schools for 10,000 students, owning 3 million square feet of real estate valued at $600-700 million.
During 2008 crisis, Scott gambled all on one property acquisition, pivoting to hotels and then education for $100-150 million yearly.

REFERENCES

Blackstone (investment firm that acquired Sergio's company).
Bizee (platform for starting LLCs, used by James and entrepreneurs).
Yellow Pages (early sales job inspiring Sergio's independence).
AI tools (daily use for automation and insights).
Humanoid robots (silver models sold by Teddy's company).
Drones (Teddy's high school photography business start).
"Ego is the Enemy" by Ryan Holiday (book impacting Teddy's mindset).
Audible (platform for Teddy's book listening).
Swimwear, goggles, paddles, shoes (Joe's product lines, including high-end designer and competitive brands).
Trusts (financial structures for generational wealth preservation).
Pickup truck and tools (Scott's 1999 startup equipment).
Charter schools (Scott's pivot market, starting with Jamaica, Queens building).
Real estate portfolio (Scott's 3 million square feet with partners).

HOW TO APPLY

Identify a repetitive business task and integrate AI to automate it, freeing hours weekly for strategic planning like Sergio does daily.
When facing doubt from family during a startup, document small wins like email responses to prove traction and build perseverance.
After an initial business exit, evaluate buyback opportunities to reclaim control and inject founder energy, as Sergio did post-Blackstone.
Start small in emerging tech niches, like drones to robotics, scaling patiently by leveraging trends without chasing hype, mirroring Teddy's path.
Invest early earnings in self-education via audiobooks on mindset, applying lessons to neutralize ego during rapid growth phases.
Focus on one industry need, such as niche swimwear, investing all savings despite risks, and compete fearlessly against giants like Joe.
Use trusts and frugal budgeting to structure wealth, teaching family to balance luxuries with asset protection for longevity.
During economic dips, gamble on undervalued assets boldly but verify partners thoroughly, pivoting to high-demand sectors like Scott in 2008.
Cultivate urgency by tackling one postponable action daily, expanding real estate or business holdings methodically.
Hold assets long-term, resisting sales temptations, and mentor youth on returning hustle to sustain generational momentum.

ONE-SENTENCE TAKEAWAY

Persist through doubts, automate with AI, and build patiently in niches to amass enduring wealth like these Long Island moguls.

RECOMMENDATIONS

Form an LLC immediately using simple platforms to protect assets, avoiding Sergio's early ignorance of entity basics.
Automate monotonous tasks with AI daily to boost productivity and focus on high-value critical thinking.
Persevere past family doubts and crises by showcasing responsiveness to outmaneuver larger competitors.
Maintain startup mentality post-growth, prioritizing employees to sustain innovation after any acquisition.
Embrace measured dissatisfaction as motivation, tempering it to avoid burnout while chasing bigger goals.
Build brands slowly in emerging tech, leveraging AI trends for exponential scaling without fad-chasing.
Fail fast in small ventures to learn more than school, investing early profits in personal development books.
Neutralize ego with philosophical reads during successes, recognizing multiple achievement levels ahead.
Endure business volatility daily, as persistence turns inevitable downs into life-changing ups.
Use trusts and frugal habits to preserve generational wealth, caring for teams while controlling costs.
Honor handshakes with unyielding honesty to forge lasting global partnerships over contracts.
Seize undervalued opportunities in turmoil, verifying trusts to pivot into scalable impact areas.
Adopt constant urgency in actions, holding assets patiently for compounding long-term gains.
Mentor emerging youth hunger, sharing methodical patience stories to fuel collective hustle.

MEMO

In the shadowed enclaves of Long Island, New York, where manicured hedges conceal estates worth tens of millions, a new generation of wealth hides from the city's glare. James Jani, host of the School of Hard Knocks, ventures beyond gated drives to interview reclusive millionaires, revealing how they transformed humble starts into fortunes. These aren't flashy Manhattan tycoons but deliberate escapees seeking land, privacy, and control—hallmarks of eight-figure success. Jani's raw encounters, often met with suspicion or outright rejection, underscore the guarded world of the ultra-rich, yet yield profound lessons on grit and innovation.

Sergio, a 53-year-old entrepreneur born to Spanish immigrants, embodies the immigrant hustle. Starting in his Brooklyn basement with zero capital during the 2008 crash, he built an internet advertising firm sold twice to Blackstone for $200 million. Bought back to reclaim its soul, the company now valuations at $300-500 million. Sergio credits an early epiphany—watching Yellow Pages reap $100 million from his code while pocketing just $10,000—for his leap. He warns private equity often erodes founder spirit, urging eternal startup vibes. On AI, he predicts a three-year upheaval, advocating its use for drudgery so humans tackle ingenuity. His mantra: Believe in yourself, dissecting grand visions into actionable steps.

At 30, Teddy Hagerty defies the overnight myth with patient robotics ascent. From high school drone photography to leading global humanoid sales, his firm eyes $100 million this year— a 100x leap in four years. "Get rich slow," he insists, scorning fast-money traps that crumble. Early millionaire at 24, Teddy squandered on haste before learning life's timeline allows deliberate building. "Ego is the Enemy" by Ryan Holiday recalibrated his hubris, reminding that Lamborghinis don't equate mastery. He champions failing fast over formal education, investing in self through trials. For the young: Persist; down days precede breakthroughs.

Joe DiRenzo, 81 and still rising at dawn for work, turned $12,500 savings into a $300-500 million swimwear empire. An Italian immigrant from Brooklyn's tenements, he ignored naysayers launching amid family needs. Niche dominance in high-end gear and competitive lines beat giants unafraid. Losing money year one? No deterrent. For legacy, trusts shield wealth while frugality tempers indulgence—vacations yes, but means-respecting. Handshakes seal his Asian deals on trust alone. His ethic: Honesty over exploitation; one's word is business's bedrock.

Scott Baron, 50, gambled a $30,000 loan into a $150 million construction behemoth. From Queens' modest roots, his 1999 pickup-truck start pivoted in 2008's chaos to hotels, then charter schools—now 21 buildings for 10,000 kids. Owning 3 million square feet worth $600-700 million, he scales via "sense of urgency": Pedal down, no delays. A father's warning lingers—one ethical slip brands you forever. Ronald Reagan's "trust but verify" guides partnerships. Yet, he sees America's youth reclaiming hunger, a lost generation stirring. Parable wisdom: Walk methodically to conquer all, not sprint for one.

These moguls converge on patience's power: Hold assets, endure volatility, automate wisely. Jani's cold Long Island treks highlight accessible paths—LLCs via Bizee, AI leverage, niche focus—demystifying wealth. In a world craving quick wins, their stories affirm: Slow, honest builds endure, turning immigrants' basements into gated legacies.