The Fortunate FISHES Podcast

Surviving the Odds & Reinventing the Orthodontic Industry | Dr. Jason Gladwell

Dr. Jason Gladwell mailed Glock 19 handguns to a gun-club list as a promotional offer for clear aligners. CNN ran it. Invisalign pulled him off their site. His own PE group scrubbed him. The schedule sold out anyway — and the gun store had its best month ever. The stunt is the hook. The operator underneath it is the story: dirt-poor North Omaha to the #2 Invisalign provider in the U.S., 15,000 cases, a 9x single-day world record, and a 2021 exit to LightWave he rolled 30% back into. Jason's story is one of self-invention: a single mom, a brother sliding into gang life, a move to North Carolina to escape it, and a degree he designed himself because a mentor told him biology was worthless.  No money, no network, no study habits — just a kid who got into NC State off the waitlist, looked around the room, decided he was outgunned, and built the discipline to win anyway. He left the herd on every decision that mattered, and absorbed the arrows each time. The Outgunned Operating System: → Set rules your peers won't follow — "never miss a class" was the entire edge at NC State → Disagree and commit: pitch the idea, let the team object, then own 100% of the downside if it breaks → Build the contingency plan before you fly close to the sun, not after The financing reinvention is the quieter masterclass. The industry wanted 20% down and full payment before treatment ended. Gladwell read that the average person carries $300–400 in disposable income, so the math didn't math. He flipped it: low down, 0% financing, direct deposit, and he'd stretch a 24-month case to 28 months. Soccer moms talked. The referral engine paid for everything. On forgiveness, compounding, and the exit: → A grudge is "drinking poison and waiting for someone else to die" — he forgives fast, but if you screw him, he's coming → He sold to LightWave in 2021, kept full control of his people and systems, bought himself a gold watch — then worked harder than ever After the liquidity event the real questions surface: are your kids competitive when they've never known adversity, and are you saying yes to others more than to your own family? For operators past their exit, that's the actual game. Books Mentioned: The 7 Habits of Highly Effective People (Stephen Covey) Making Money Is Killing Your Business (Chuck Blakeman) A Message from Garcia (Charles Patrick Garcia) It Works (R.H. Jarrett) Through My Eyes: Eye Surgeon (the surgeon's memoir Charlie references) The Yes! Attitude (Jeffrey Gitomer) Blink (Malcolm Gladwell — no relation) Unreasonable Hospitality (Will Guidara) The Little Red Book of Selling (Jeffrey Gitomer) The Structure of Scientific Revolutions (Thomas Kuhn) For the founder who already exited and is deciding what the next 30 years are actually for. Subscribe for more insights from leaders redefining what it means to be truly wealthy.   Interested in becoming a member of R360 Global? Visit our website: https://www.r360global.com/   Charlie's LinkedIn: https://www.linkedin.com/in/charlespgarcia/ Charlie’s Substack: https://substack.com/@cpgarcia?  Instagram: https://www.instagram.com/fortunatefishes/  X: https://x.com/R360FISHES #FortunateFishes #JasonGladwell #CharlieGarcia #UHNW #UltraHighNetWorth #EntrepreneurMindset #FounderToExit #PrivateEquity #DentalDSO #Invisalign #BusinessAcquisition #SPAC #FamilyOffice #WealthBuilding #ExitStrategy #FounderStories #ContrarianThinking #LegacyWealth #R360 #DisagreeAndCommit "Message us" [https://www.buzzsprout.com/2460893/fan_mail/new]

Soldier of the Year, Space Force Tech & the Future of Venture | Chris Shonk

Chris Shonk has lived four lives most people would not survive. One of eight children, Army Special Operations Soldier of the Year, Merrill Lynch analyst, private equity founder, pawn shop operator, public-company builder, and now venture investor in AI, space, and defense. The contrarian lesson is not "move faster." It's know what is real, know what is coming, and build where they collide. Shonk calls this living between history and sci-fi — the place where serious capital, national security, and family legacy now meet. The History / Sci-Fi Barbell: → Study what actually happened, not consensus narratives. → Track the choke points: power, compute, data privacy, orbital awareness. → Invest where old-world friction meets new-world capability. He learned the pattern in Special Operations, where the edge was not shooting or fitness — everyone had that. It was digesting imperfect information, finding the gaps, building a plan, and acting under pressure.  Later, in pawn shops, the same playbook turned a gritty business into tech arbitrage: centralized inventory, CRM, online distribution, and KPIs 10x better than public competitors. The Hispanic-growth thesis he found inside those stores led to a first check into Siete Foods at 152x. The Shonk Operating System: → PACE planning: primary, alternate, contingency, emergency. → "We" over "me": gratitude, family, service, shared mission. → Capability timing: early, late, or just right. He now sits on the board of Slingshot Aerospace — the company the US Space Force uses to track every object in orbit — and tells Charlie, on the record, that the B-2 strike on Iran's nuclear facilities and the Venezuela radar blackouts were "coordinated efforts, and Space Force is a material part." For UHNW families and entrepreneurs, this is the real conversation: not how to make money, but where power is moving, what your children must learn, and how to stay useful when AI, space, defense, and energy redraw the map. Books mentioned: Atlas Shrugged — Ayn Rand Against the Gods — Peter L. Bernstein The Richest Man in Babylon — George S. Clason Boy Scout Handbook — Boy Scouts of America U.S. Army Infantry Field Manual Dune — Frank Herbert Starship Troopers — Robert A. Heinlein Journey to the Center of the Earth — Jules Verne Twenty Thousand Leagues Under the Sea — Jules Verne Replay — Ken Grimwood Ready Player One — Ernest Cline For founders, family offices, investors, and builders who know the next frontier will not be polite. Subscribe for more insights from leaders redefining what it means to be truly wealthy.   Interested in becoming a member of R360 Global? Visit our website: https://www.r360global.com/   Charlie's LinkedIn: https://www.linkedin.com/in/charlespgarcia/ Charlie’s Substack: https://substack.com/@cpgarcia?  Instagram: https://www.instagram.com/fortunatefishes/  X: https://x.com/R360FISHES #ChrisShonk #CharlieGarcia #FortunateFISHES #UltraHighNetWorth #FamilyOffice #PrivateWealth #VentureCapital #DefenseTech #ArtificialIntelligence #SpaceEconomy #NationalSecurity #AIInfrastructure #DataPrivacy #PowerInfrastructure #LegacyBuilding "Message us" [https://www.buzzsprout.com/2460893/fan_mail/new]

"Your Legacy Isn't Your Money" | Behind R360's Most Iconic Documentary Storyteller | Silvia Costa

Silvia Costa has sat in the living rooms of 31 ultra-high-net-worth families — worth an average of $600M — and asked them one question no financial advisor ever will: "What do you want to tell the great-grandchildren you'll never meet?" What comes out is not investment philosophy. It's something far more valuable. She spent two decades producing "The Business Profile" for CNBC Europe, BBC America, and Financial Times TV across 72 countries. Then she walked away to document the human side of dynastic wealth — what it's built on, and what destroys it by the third generation. The Art With Truth Framework: → Never arrive with a script. The story tells you what it is. → The ending is almost always connected to the beginning — find the thread first. → Contradictions aren't problems to resolve. They're the truth. One member in California said at the end of his filming session: "No more therapy for a month — this was enough." Another member filmed hers while receiving chemotherapy for pancreatic cancer. Her family now visits her gravesite in Miami and scans a QR code on her headstone to watch her speak directly to generations she would never meet. That is what a legacy film actually does. What thriving multi-generational families share: → Family unity held as non-negotiable — not agreement, unity. → Emotional capital: the ability to process love across generations. → Values transmitted alongside wealth, not after it disappears. 80% of R360's membership are first-generation wealth creators. The research is clear: without the story behind the money, the money is gone by generation three. Silvia Costa has built the system that changes that. Books mentioned: Love Work:Live Life — David Oliver Good to Great — Jim Collins For founders, wealth creators, and family office principals who understand that capital without context is just a countdown. Subscribe for more insights from leaders redefining what it means to be truly wealthy.   Interested in becoming a member of R360 Global? Visit our website: https://www.r360global.com/   Charlie's LinkedIn: https://www.linkedin.com/in/charlespgarcia/ Charlie’s Substack: https://substack.com/@cpgarcia?  Instagram: https://www.instagram.com/fortunatefishes/  X: https://x.com/R360FISHES #UHNW #FamilyOffice #LegacyPlanning #WealthManagement #MultiGenerationalWealth #FamilyWealth #PrivateWealth #WealthCreators #Entrepreneurship #LegacyFilms #DocumentaryFilm #FortunateFishes #R360 #FamilyGovernance #WealthPreservation #UltraHighNetWorth #FounderStory #BusinessLegacy #WealthTransfer #FamilyBusiness "Message us" [https://www.buzzsprout.com/2460893/fan_mail/new]

14 Years on the Equities Desk: The Truth About Big Money Trading | Luis d'Amato

Most advice on wealth is written by people who've never traded through hyperinflation, been on a trading floor on 9/11, or built a firm after being legally barred from their industry for eight years. This conversation is different. Luis D'Amato spent 20 years inside Hedging Griffo — Brazil's legendary trading house acquired by Credit Suisse — then walked away with an eight-year non-compete to build Aston Capital Management from zero in Miami. He now manages $700M across US taxpayers and international families. The Aston 7-Asset Endowment Allocation: → 25% equities (low end of range — valuations stretched after three strong years) → 5% hedge funds (discretionary macro for negative correlation) → 10% cash (tight credit spreads don't pay you to take risk) → 25% public credit → 10% private equity / venture → 10% private real estate (tax-advantaged for US payers) → 15% private credit — never sponsor-backed direct lending On 9/11, Luis was on the phone with his Bear Stearns counterpart when the second plane hit. A director on his desk said it was impossible — it couldn't be a second plane. Brazil's exchange closed within the hour. The lesson wasn't about markets. It was that the people closest to the information are often the last to believe what's actually happening. Three red flags when hiring a wealth advisor: → They work at a bank (not a fiduciary — shareholders come first) → They earn on trading commissions (incentive to churn your account) → You can't see the fees (rebates and spreads buried in products) Why this matters past $10M: The real alpha isn't in stock picking. It's rebalancing discipline, tax-aware allocation across liquid and illiquid buckets, and access to niche managers too small for the big bank platforms. Luis runs the same allocation for a $100K Aston Fund investor that he runs for $10M+ wealth clients. That's what fiduciary actually looks like. Books Mentioned: Do Nothing! Discover the Power of Hands-Off Leadership (Keith Murnighan) Die With Zero: Getting All You Can from Your Money and Your Life (Bill Perkins) The Psychology of Money: Timeless Lessons on Wealth, Greed, and Happiness (Morgan Housel) The Good Life: Lessons from the World's Longest Scientific Study of Happiness (Robert Waldinger & Marc Schulz) Que Bobagem! (Natalia Pasternak & Carlos Orsi) — Portuguese only Scientific American — Magazine The Great Partnership: Science, Religion, and the Search for Meaning (Rabbi Jonathan Sacks) Late Admissions: Confessions of a Black Conservative (Glenn C. Loury) For founders post-exit, family office principals, and anyone whose private banker has never said the word "rebalance." Subscribe for more insights from leaders redefining what it means to be truly wealthy.   Interested in becoming a member of R360 Global? Visit our website: https://www.r360global.com/   Charlie's LinkedIn: https://www.linkedin.com/in/charlespgarcia/ Charlie’s Substack: https://substack.com/@cpgarcia?  Instagram: https://www.instagram.com/fortunatefishes/  X: https://x.com/R360FISHES #UltraHighNetWorth #FamilyOffice #WealthManagement #PrivateCredit #PortfolioAllocation #Endowment #HedgeFunds #PrivateEquity #FiduciaryAdvisor #AssetAllocation #PostExitPlanning #FortunateFISHES #CharlieGarcia #LuisDAmato #AstonCapital #HedgingGriffo #CreditSuisse #EmergingMarkets #BrazilInvesting #MiamiWealth #IronmanMindset #DieWithZero #MorganHousel #KelloggMBA #CFA #AlternativeInvestments #RIA #OffshoreInvesting #WealthTransfer #LegacyPlanning "Message us" [https://www.buzzsprout.com/2460893/fan_mail/new]

Built a Global Retail Empire at 21, Then Sold It for 8 Figures | Anthony Ng Monica

Anthony Ng Monica from London refused to fail in both business and life. He built a company called Swogo with no co-founders, no venture capital, and no connections. Then sold it for eight figures, all cash. Anthony did it by understanding something most founders never figure out: enterprise sales is not about selling. It's about helping someone buy, protect their job, hit their targets, and make their team look good. He doesn't talk about hustle. He talks about systems — for decisions, for exits, for the body — and why founders who skip the last one eventually pay for it. What makes this conversation different is the specificity. No motivation, no frameworks dressed up as insight. Just a 12-year-old scraping Yellow Pages, a 21-year-old cold-emailing VCs for intern jobs he never intended to keep, and today a founder who built inside Walmart, Best Buy and Sephora one audacious cold outreach at a time — including Brazilian beer sent to a Walmart executive that got destroyed by security. He still got the meeting. The Competitor Sacrifice Framework — closing 8 of the 10 largest consumer electronics retailers globally: → Identify the conglomerate with the most subsidiaries — your real prize → Offer the competitor a free trial to generate leverage, not revenue → Walk into your target and say "their competitor is already live" — urgency manufactured, deal closed The Information Asymmetry Exit: → Read every quarterly earnings report of your top customers — know their business better than they do. → When Best Buy signaled category slowdown internally while analysts called e-commerce unstoppable, he sold. → The buyer never saw it coming. He did. That's the exit. The Decision Probability Framework: → Assign every major decision a probability: 10%, 50%, or 90%. → When uncertain, always round down. → Take the highest-probability path, commit fully, and accept the outcome — it's a numbers game, not a talent game. After the exit, Anthony didn't retire. He noticed what most founders miss until it's too late — a decade of peak performance quietly degrades the moment the motivation disappears. The machine that generates the exit is the founder's body, mind, and decision-making clarity. So he built Daily Body Coach (dailybodycoach.com): high-touch health optimization for executives and entrepreneurs who travel, eat out, and want to perform at the highest level without living like an athlete. Each client gets a dedicated team — trainer, nutritionist, and PhD-level psychologist — matched using a proprietary profiling system built around one insight: 30% of outcomes come purely from the coach-client relationship. The plan adapts to your lifestyle and predicts when you're about to go off track and course-correct before it happens.  The goal is simple: make high performance your permanent identity, not your next 90-day project. Books Mentioned: The Secret —  Rhonda Byrne Pitch Anything — Oren Klaff The Catalyst — Jonah Berger For the founder who has already won once and is building the next thing with more intention, more leverage, and far less patience for anything that doesn't compound. Subscribe for more insights from leaders redefining what it means to be truly wealthy.   Interested in becoming a member of R360 Global? Visit our website: https://www.r360global.com/   Charlie's LinkedIn: https://www.linkedin.com/in/charlespgarcia/ Charlie’s Substack: https://substack.com/@cpgarcia?  Instagram: https://www.instagram.com/fortunatefishes/  X: https://x.com/R360FISHES #EnterpriseGrowth #EightFigureExit #BootstrappedToExit #UltraHighNetWorth #ExitStrategy #B2BSales #EnterpriseSales #ConsumerElectronics #RetailTech #WealthCreation #FounderStory #FortunateFishes #DailyBodyCoach #HighPerformance #OperatorMindset #SelfFunded #InformationAsymmetry #Health #EliteWellness "Message us" [https://www.buzzsprout.com/2460893/fan_mail/new]