The Fifth Quarter Show

How This Founder Made and Lost $1.2M By His 21st Birthday, Jeremy Newsome, RealLife Trading

Jeremy Newsome is the founder of RealLife Trading, one of the largest trading education platforms in the world, teaching hundreds of thousands of people how to trade safely. At age seven, he watched Forrest Gump, sold blackberries door to door, saved $1,300, convinced his dad to match it, and bought Apple stock. That investment would be worth $40 million today. He turned $400K into $1.2M trading silver by age 20 — then lost it all on his 21st birthday. He's completed three Ironmans, co-hosts the Broke to Awoke podcast, and sits on the board of Aerial Recovery, the world's largest anti-human trafficking organization, which has saved over 8,500 children. In this episode, we get into: - How a seven-year-old watched Forrest Gump and saw a roadmap to financial freedom — "we don't have to worry about money no more" - The blackberry hustle: shirtless, no shoes, Georgia summer, $1,300 in Ziploc bags sold door to door - His dad's investing lesson that still holds: "If revenue is increasing, the stock price will go higher over time" - The $40 million mistake — selling Apple in 2000 and never reinvesting - Turning $400K of other people's money into $1.2M trading silver at age 20 - Buying silver at the highest price in human history with leveraged money — and losing $1.2M on his 21st birthday - "I didn't want to lose my dad's approval" — the spiritual root of why he held instead of cutting losses at $500K - "Financial freedom is second grade math repeated consistently" — 300 people x $167/month = $50K/month - Why triple partnerships never work — the math of two ganging up on one - "Don't give equity away" — the most expensive lesson entrepreneurs keep repeating - Paying $1,000/hour for a business coach when he was broke — and why it changed everything - "Money cannot buy a finish line" — why physical discipline is the key to trading discipline - 14,200 jump ropes in 14 hours straight — the migraine, the puke, and why he'd do it again - "The brokenness of any country is in direct proportion to the brokenness of its men" - Aerial Recovery: repurposing special forces veterans to save children from sex trafficking across 16 countries - 8,500+ children saved — the largest anti-human trafficking organization in the world - "There's no one else saving kids with their trading profits" — why he's playing a different game Jeremy gets raw about the father wound that caused his biggest financial loss, the business partner divorces that ripped out his heart, and why he believes most men are broken and settling. We go deep on the spirituality of money, why your happiness is a non-negotiable business strategy, and how he went from a kid who didn't want to worry about money to a man who uses trading profits to save children from trafficking. Move with clarity. Build with soul.

Elk Ridge CEO, Lame Kinikini: The Creative Finance Playbook That Built a $75M Portfolio

Lame Kinikini is the founder and CEO of Elk Ridge Investments, an alternative investment firm managing over $75 million across real estate, short-term rentals, creative finance, and asset-backed lending. He's closed more than 200 creative finance deals, built Elk Ridge into an eight-figure company in under five years, and now mentors over 100 students through his Fearless Investors community. But he didn't start with money — he started knocking doors. In this episode, we get into: - From $40K summers to six-figure seasons — how door-to-door sales at Vivint built the mental fortitude behind everything - "Tell me I can't" — the Michael Jordan quote on his wall and the mindset that let him close his first creative deal with zero experience - 50 properties in 5 months — the hockey stick that started with one bad deal he still holds today - Why his first creative finance deal lost him money — and why he calls it tuition, not failure - The 2023 crash: 48% supply influx, rates through the roof, burning cash month to month — and the pivot that saved everything - Creative finance as the cheat code — how a blended 4% rate across his portfolio made him profitable when everyone else was drowning - $1.4 million in quantifiable losses — and the unquantifiable cost of depression, firing people, and sleepless nights - "I've never been a depressed person" — the Thanksgiving he woke up and regretted it, and why he'll never dismiss mental health again - The wrong partner who almost derailed everything — and the right one who helped them pass last year's numbers by midsummer - "The cheapest you'll ever get great talent is today" — why tripling payroll doubled revenue - His dad's line: "When you don't give when you have nothing, you'll never give when you have everything" - Date nights as competitive advantage — why Tuesday and Thursday with his wife is his most dangerous business habit - "Money increases your capacity to serve" — the spiritual operating system behind the portfolio - Why enough stopped being about material things and became about legacy that never runs out Lame gets raw about hitting rock bottom in 2023, the depression he never thought he'd experience, and the business partner betrayal that almost broke him. We go deep on creative finance mechanics, why your spouse is your greatest business asset, and the moment he realized wealth was never about the portfolio — it was about how many people he could serve. Follow Lame: @lame.kinikini Move with clarity. Build with soul.

"Once You Do This, You Become Unstoppable": Jess Mah, 9-Figure Founder & Venture Studio CEO

Jess Mah built a six-figure business in middle school, dropped out of high school at 15, and at 19 became one of the youngest women accepted into Y Combinator. On paper, she was a Silicon Valley prodigy — Forbes and Inc 30 Under 30, venture-backed, scaling fast. But in 2012, the bank balance was heading toward zero, the product wasn't working, and she fired her team just to survive. She rebuilt inDinero into a hundreds-of-employees company at a nine-figure valuation, stepped out of the CEO seat on her own terms, and now runs a venture studio building companies across AI, fintech, and bioelectrical therapies targeting cancer. She's also the youngest graduate of the Harvard President's Program. In this episode, we get into: - Forbes 30 Under 30 while burning cash — the gap between perception and reality in 2012 "- I was bottom quartile intelligence, but the most creative and hardest working" — leaning into what you're actually good at - The Steve Blank advice that changed everything: people don't buy tools, they buy outcomes - Firing friends — why she's done it dozens of times across multiple companies and how she structures it differently now - "Even Fortune 50 CEOs tell me they should have fired that person a year earlier" — why no one outgrows this mistake - Stepping out of the CEO seat during COVID — and why she didn't lose her identity doing it - EMDR therapy as an entrepreneur's secret weapon — "You would be unstoppable" - Building from desire vs. brute force — how her approach to starting companies has fundamentally changed - The apprentice model: what she would have done if she couldn't start a company — work for Richard Branson for free - Why short-term relationships are like day trading stocks — you don't get compounding returns - Twice-a-week check-ins with every team member for the first 30 days — her highest-leverage use of time - Playing the long game: the people who look wrong on paper but work with you for 25 years Jess gets raw about the loneliness of being a kid programmer before coding was cool, the weight of public accolades when your company is dying, and the psychological game that separates builders who last from those who don't. We go deep on inner game — meditation, somatic therapy, EMDR — and why she believes 50% of entrepreneurship is working on yourself. She makes a compelling case that the founders who win aren't the smartest, they're the ones who build environments where everyone around them gets to create something awesome. Follow Jess: @jessmahofficial Move with clarity. Build with soul.

Building The First AI Native Holding Company: Infinity Constellation CEO, Brennan Pothetes

Brennan Pothetes is a fintech operator who built and sold Butter Insurance to Odeko, then got tapped to create something that's never been done before — the first AI native holding company. Infinity Constellation launched in May 2025 with $17 million, eight AI companies already post-revenue, and a thesis that the entire venture model is broken. He calls it Y Combinator meets Berkshire Hathaway. In this episode, we get into: - Why he believes too much capital has killed more companies than it's helped - "Headcount kills" — the core pillar that makes his CEOs solve with technology before people - One engineer built a marketplace system in 28 days that used to take 18 months and $20M - Y Combinator meets Berkshire Hathaway — why he took pieces of both and rejected the rest - Starting companies for $250K–$500K and getting to $1M ARR before deploying real capital - The biggest company in the portfolio: $300K invested, almost $6M in contracted ARR - 25% equity guaranteed at $1B EV — the incentive structure that aligns founders, investors, and LPs all the way down - Why he doesn't do one-on-ones — and what Jensen at NVIDIA taught him about information flow - The burnout story: 70+ cold calls a day for 8 months, couldn't get off the couch, and his wife asked "Do you want to be the CEO of an insurance company?" - "If you're burnt out, you're not loving what you do" — the controversial take on founder burnout - Speed is the ultimate moat — why he'd 100x his pace if he could - The $2 trillion service economy reshuffling for the first time in 200 years - Autonomous CEOs — the experiment he's already running - Planning for IPO, not exit — why Constellation Software and Berkshire are the models Brennan gets raw about selling a company he'd fallen out of love with, the identity shift from first-time founder to holdco CEO, and why the founders who win aren't the ones with the most capital — they're the ones who love the game. We go deep on incentive design, the trust curve of AI adoption, and why the tech moat every VC is chasing might not exist in 5 years. Follow Brennan: @brennanpothetes Move with clarity. Build with soul.

From Broke BMX Rider to a Fortune 100 Exit: Ross Hamilton, Founder of Saving Homes

Ross Hamilton is a former semi-pro BMX rider who turned a career-ending injury into a real estate empire — 50 rental properties by 24, all through creative financing with no money. He then built Connected Investors, the world's largest network of real estate investors processing $3B in monthly lending requests, and sold it to a Fortune 100 company. Now he's dedicating the next 20 years to Saving Homes — a nonprofit that provides interest-free grants to families facing foreclosure. In this episode, we get into: - How riding with Dave Mirra taught him the power of proximity before he ever made a dollar - Knocking on foreclosure doors at 19 looking like a 12-year-old — and why he kept going back - The fake business partner "Dr. Elliott" he invented to buy time on deals he didn't know how to structure - "Just get to the next telephone pole" — why knowing the next step beats knowing all the steps - No internet, no YouTube, no podcasts — learning real estate from Barnes & Noble books he couldn't afford to buy - Subject to deals and creative financing: how he controlled 30-40x his capital with almost nothing down - The nightmare tenant who faked a seizure in court, sued him for a dead body, and burned the house down - Building Connected Investors by solving his own bottleneck — buyer's list to tech platform - "Flip a property, add a feature" — bootstrapping a tech company with real estate profits - The B2B/B2C model that let him spend $1M/month in ads profitably from day one - Culture is not a buzzword — the moment he realized it after selling to a Fortune 100 company - Immediate commissions, $20K bonuses, and why 2.4% raises don't motivate anyone - The identity death of selling your company — and why he calls himself a "recovering capitalist" - Saving Homes: the self-sustaining nonprofit model that returns capital to save the next family Ross gets raw about building his fortune on other people's misfortune — the tension most real estate investors never talk about. We go deep on the promise he made to himself a decade before launching Saving Homes, the culture clash of integrating into corporate after an exit, and why real success came down to one word: gratitude. Follow Ross: https://www.linkedin.com/in/cirosshamilton/ Move with clarity. Build with soul.