Risky Business

Sam Stone
  • 5.0 (12)
  • ENTREPRENEURSHIP
  • UPDATED SEMIWEEKLY

Hearing from those who have taken BIG RISKS and finding out what they learned. Here to Encourage / Challenge / Push YOU to take that next RISK Hosted by: Sam Stone

  1. MAR 27

    Jason Black: He took the Risk... Now He Builds Some of he Most Luxurious Homes in Louisville

    Sponsor Highlight: River City Mortgage LLC NMLS 142954 https://rchomeloans.com/ Call or Text: Nick Hunter 513-490-4235What does it actually take to walk away from a stable corporate job and build a luxury business from scratch?In this episode of Risky Business, we sit down with Jason Black — Louisville’s premier luxury home builder and co-owner of Artisan Signature Homes.Jason shares how he went from working in corporate finance at companies like Humana to taking a massive leap of faith into home building… with ZERO experience.From building his first homes while still working full-time… to winning Homearama… to creating multi-million dollar custom estates — this episode breaks down what it really takes to bet on yourself and win.If you're thinking about starting something… this is the episode you need.⏱️ Timestamps00:00 – Why Jason Black’s name is everywhere in Louisville real estate01:04 – His corporate background (Humana, finance career)02:26 – The early interest in home building03:22 – Getting forced into a career decision04:42 – Building his first homes with zero experience06:17 – The moment he quit his corporate job07:54 – Building a Homearama house (and winning BEST OF SHOW)10:53 – Scaling a luxury home building business12:48 – Transitioning to Artisan Signature Homes15:45 – Building ultra-luxury homes and legacy properties17:16 – Advice for people stuck in a job they don’t love18:57 – Why you can’t wait for the “perfect moment”20:03 – Real estate investing and diversification22:03 – The importance of mentors and relationships24:45 – Expanding into luxury home renovations26:14 – Why execution beats overthinking28:57 – Final advice: Just take the leap👤 Guest InfoJason BlackLuxury Home Builder | Co-Owner of Artisan Signature Homes📍 Louisville, Kentucky🏡 Builds high-end custom homes in areas like Norton Commons, Prospect, and Anchorage

    39 min

  2. MAR 2

    Kyle Hume: How I Went Viral, Turned Down Labels, and Bet on Myself

    Sponsor Highlight: River City Mortgage LLC NMLS 142954 https://rchomeloans.com/ Call or Text: Nick Hunter 513-490-4235 SUBSCRIBE FOR MORE In this episode of the Risky Business Podcast, we sit down with Kyle Hume — singer, songwriter, and producer — to break down the real story from COVID era to now: how he used TikTok as a feedback loop, wrote songs from comments, went viral, and built a career without taking a traditional label path.Kyle talks through his background (Louisville → UK), his early days in computer science and internships at GE, the exact content experiments that worked, the moment a song blew up through other creators, and the business side of music — including why he turned down label deals and how he thinks about marketing music today.We also talk touring, album rollout, staying consistent, and what he’d tell a younger creator trying to make it right now.Kyle HumeSinger • Songwriter • Producer • Independent ArtistSpotify: https://open.spotify.com/artist/2XhX0GQkGHT8B4B5u8E5zZNew Album Release: March 27Louisville native now based in Nashville.Known for: “If I Would Have Known,” “Fine,” and viral songwriting from TikTok prompts.Timestamps0:00 Intro + meet Kyle Hume1:40 Louisville/UK background + early path3:00 Engineering → computer science + GE internships4:50 Getting into music (remixes, producing, learning fast)6:30 First song attempt + early momentum8:15 Turning down the “safe job” route10:00 Starting TikTok + testing content ideas12:00 The “write songs about people’s Instagrams” idea14:20 Turning it into an engagement machine16:00 Viral relationship/IG match videos + first big spikes18:00 Writing songs from comments (daily reps)21:00 First big “risk” move + grinding while still in school23:40 Flying to LA during dead week + learning the industry25:30 The comment that changed everything (“never getting to say goodbye”)26:50 Another creator blows it up + finishing the song fast28:20 Labels start calling + getting a manager29:45 Why Kyle turned down label deals (numbers, ownership, leverage)32:20 Content strategy shift: don’t chase followers, sell the song33:10 “Fine” blows up + going Gold36:00 Output cadence (5 videos/week) + tour promo37:30 Tour dates + Louisville show details + album release show41:10 Advice for young creators: start now, take shots, choose voices wisely45:10 Rapid fire: favorite song/video/restaurant48:00 “Holy cow this is working” moment + numbers mindset50:10 Perfect day in Nashville + wrap up

    54 min

  3. FEB 10

    AUSTIN SAUER: Scaling Louisville Real Estate Media to $1M

    Sponsor Highlight: River City Mortgage LLC NMLS 142954 https://rchomeloans.com/ Call or Text: Nick Hunter 513-490-4235 Welcome back to the Risky Business Podcast. Today I’m sitting down with my friend Austin Sauer — Louisville real estate media pro and a guy I genuinely believe is building one of the best service businesses in this city. Austin’s story hits hard because it’s not some overnight, highlight-reel success. He left medical sales in 2019, had zero book of business, built a studio, went months without shooting… and he’ll tell you straight up: the “if you build it, they will come” mentality is a lie. We talk about what actually grows a service business: why what you deliver isn’t the problem you solve how to scale something that isn’t scalable at the outset the “bucket method” for figuring out what’s working (and doubling down) building authority with content instead of posting the same stuff everyone else posts patience, infrastructure, and why most people quit right before it turns Austin also shares the reality of being years into business with $5 in the bank account, and why he still never considered going back. If you’re a service-based entrepreneur, a creative trying to build a real business, or you’re sitting on a risk you know you need to take… this episode is for you. Guest: Austin Sauer (Louisville Real Estate Media) 👇 Question for you: What are your 6 “buckets” — where did your best clients come from last year? Like, comment, subscribe, and share this with someone who needs a push. Chapters (timestamps) 0:00 Intro + why Austin’s story matters 0:45 Meet Austin Sauer (Louisville real estate media) 2:05 Snowmageddon + learning from every guest 3:10 Sponsor: River City Mortgage 4:35 Scaling a service business that “isn’t scalable” 6:10 Austin’s start: photo-first, adapting to video world 8:15 “Delivering media isn’t the problem we solve” 10:05 Going full-time in 2019 + the studio mistake 12:10 Creative world misconception: “pay me because I value my work” 14:30 Taking care of people = repeat business 17:15 The “5 D’s” (why sellers are stressed) 19:40 Long game mentality + patience 21:10 $5 in the bank with first kid — why he didn’t quit 23:45 1,200 homes shot (team total) + what success actually looks like 25:10 Sharing numbers + why transparency matters 27:40 Cameron’s “bucket method” (lead sources + doubling down) 31:00 Social media authority + standing out in a crowded market 34:10 “Most people don’t choose you because they don’t know you” 36:40 Best real estate media = adaptability, not perfection 39:30 Advice for 20–40 year olds taking risks 42:20 Give value first, don’t expect return

    46 min

  4. JAN 29

    PAT RIGSBY - Everything Is a Trade: What I Learned Building 40 Businesses

    Most people think success is about hitting milestones.Revenue numbers. Titles. Rankings. Wins. But what happens when you hit those milestones… and they feel empty? In this episode of Risky Business Podcast, I sit down with Pat Riggsby — former college baseball coach, multi-time founder, six-time bestselling author, and someone who’s owned or co-owned nearly 40 businesses, including scaling fitness and sports performance franchises to 275+ locations worldwide.What makes this conversation different isn’t the résumé — it’s the honesty. Pat started entrepreneurship around age 30, after spending a decade in college baseball. Like many people listening, he felt the pressure of “playing catch-up,” especially watching others online who seemed further ahead.This episode breaks down:Why everything in life is a trade Why social media makes entrepreneurs feel behind The danger of comparing your full movie to someone else’s trailerWhy your first business doesn’t need to succeedHow being bad is the price of eventually being goodWhy consistency beats talent, capital, and hypeThe real reason follow-up is a superpowerHow Pat differentiated by doing what others wouldn’tWhy he walked away from a growing empire to be present with his familyHow to define “enough” before success defines it for youThis episode is especially for:People in their 20s and 30s who feel lateEntrepreneurs stuck consuming instead of executingHigh performers questioning the cost of “more”Anyone afraid that one failure means they’re not cut out for businessIf you’ve ever thought:“Maybe I missed my window.”“Everyone else is ahead of me.”“What if my first business fails?”— this conversation will hit home.TIMESTAMPS: 00:00 – “Everything is a trade” (the mindset that changes everything) 02:15 – From college baseball coach to entrepreneur at 30 04:48 – Why success milestones can feel hollow 07:02 – Feeling behind in your 30s (and why it’s a myth) 10:45 – Consumption vs production (why most people stay stuck) 13:30 – You have to be bad before you can be good 17:00 – Social media is a highlight reel, not the real movie 21:50 – Why my first businesses weren’t all successful 24:04 – Doing what others won’t do (the real differentiator) 32:40 – Walking away from success to prioritize family. Sponsor Highlight: River City Mortgage LLCNMLS 142954 https://rchomeloans.com/ Call or Text: Nick Hunter 513-490-4235

    46 min

  5. JAN 4

    SAM REAGAN - KEEPING YOUR FAITH IN COLLEGE

    Welcome back to the Risky Business Podcast.Today’s episode is extra special — I sat down with my guy Sam Reagan to talk about a risk that doesn’t get enough attention: choosing faith in college when everything around you pulls the other direction.Sam was a freak athlete (state record long jump), went to the University of Kentucky for track, and he’s honest about what happened when he got there — the freedom, the pressure, the influence, the drift, and the weight of doing life without the right people around him.Then everything changed.He made a simple commitment — one hour a day locked in with God — and what started as a chore turned into a ripple effect: people knocking on his door for prayer, moments of real vulnerability, and a confidence that faith isn’t just something you inherit… it’s something you choose.Follow the Risky Biz Podcast on IG: https://www.instagram.com/riskybizpodcast/?hl=enFollow The Risky Biz Pod on TikTok:Want To Sponsor The Show? Click Here: https://riskybusinesspodcast.com/We also talk about:Why your friend group determines your futureHow to be a Christian on a secular campus without being weird or fakeThe difference between “legalism” and a real relationship with ChristWhy this generation can spot fake instantlyWhat it looks like to live your faith in the workforce (and in real estate)And what Sam’s doing now in Phoenix — including ministry connected to ASUIf you know a young person navigating college, identity, temptation, or purpose — send them this episode.And if you want to be on the show (or know someone who should), go to riskybusinesspodcast.com and submit them.This episode was shot, edited, and marketed by Louisville Podcast Studio in Louisville, Kentucky.0:00 – Choosing faith in college is a real risk0:28 – Meet Sam Reagan (UK → GCU junior year)1:40 – Growing up in church + the “fishbowl” effect2:13 – “When I got to Kentucky… I wasn’t that guy”2:21 – The freak athlete story (state record long jump)2:35 – Quick support message + share the show3:15 – How far is 24’5”? (crazy athletic comparison)4:30 – Track took him to UK… and the freedom to fall away5:17 – “These guys are cool… NIL money… and I drifted”6:12 – The turning point: “I’ve been made for more than this”6:33 – The 1-hour-a-day challenge with God7:28 – People start knocking: prayer requests + ripple effect8:36 – The soccer party moment: praying in the middle of chaos10:10 – Sponsor callout + why this message matters11:06 – Faith becomes yours when you leave home14:07 – Why he left UK: Camp Love + calling to ministry16:32 – Ministry at ASU: 2,000 students + “someone saved every week”18:02 – The friend filter: “Show me your friends, I’ll show you your future”20:18 – Biggest challenge for Christians going to secular school22:26 – “Christians should be the most fun people”23:33 – Real estate + integrity: being a Christian in the workforce28:12 – Legalism vs relationship: freedom + conviction30:12 – Our generation can spot fake fast (dopamine + consumption)31:02 – “Silent revival” + using TikTok/IG for theology33:42 – Final challenge: bold prayer life + bold faith + real love35:07 – Final sendoff + Sam Reagan’s IG

    35 min

  6. 12/23/2025

    SAM STONE: The Risk of Going All In: Real Estate

    Sam Stone interviews entrepreneurs about risk… but this time we flipped the script. In this episode of the Risky Business Podcast, Cameron Becht sits down with Sam Stone (yes—the host) to uncover the real risks Sam took to become one of the top-performing solo real estate agents in Kentucky. We get into: Why 99.7% of people won’t choose you (and why that’s freeing) How Sam built an audience before he even had his real estate license The “boring” daily habits that paid off years later The mindset shift that helped him stop caring what people think How social media + evergreen content became his biggest unfair advantage Reinvesting, integrity, and why reputation is worth more than quick cash If you’re building a business, trying to grow on social media, or you’ve been stuck hesitating on your next move—this episode will challenge you to take a calculated risk and actually commit. 👇 COMMENT: What’s the next risk you need to take in your life or business? Follow Sam StoneInstagram: @LouisvilleKYRealEstate Follow Cameron Becht / Louisville Podcast Studiohttps://www.louisvillepodcast.studio/

    1 hr

  7. 12/03/2025

    JORDAN POHN | He Walked Away From a $200K Career… Then Risked EVERYTHING

    JORDAN POHN | He Walked Away From a $200K Career… Then Risked EVERYTHINGFollow the Risky Biz Podcast on IG: https://www.instagram.com/riskybizpodcast/?hl=enIn this episode of Risky Business Podcast, Sam Stone sits down with entrepreneur and former attorney Jordan Pohn to break down one of the most INSANE career journeys you will ever hear — from quitting a safe corporate law career, to building a multi-state mortgage empire, to surviving the 2008 financial crash, to selling to LendingTree, and eventually building a thriving private lending company, SharePoint Equity.Jordan shares invaluable lessons on:• How to take massive risks in your 20s and 30s• Why lifestyle creep destroys opportunity• The REAL grind behind entrepreneurship• Building wealth through real estate & private lending• How company culture can create 10x ROI• Surviving the 2008 mortgage crisis• Writing a seven-figure check to save his business• Selling a national lending company• Creating SharePoint Equity and lending on flips• Expanding into new states & scaling smart• Why reputation is the most valuable asset you have• Compounding, investing, and long-term wealth building• The “whatever it takes” mindset successful entrepreneurs share0:45 — Why Jordan Walked Away From a $200K Law Career2:20 — Hitting Rock Bottom: Rehab, Homelessness & Recovery5:02 — The Peer-Driven Model That Saved His Life8:00 — The Single Biggest Mistake Young People Make10:32 — Why Waiting Too Long to Take Risks Locks You In13:45 — Building 13 Branches From Scratch Across Multiple States18:40 — The LendingTree Breakthrough No One Saw Coming20:00 — How Company Culture Produced Massive ROI28:50 — The 2008 Warning Call That Changed Everything30:45 — Signing a Seven-Figure Check to Save the Company33:50 — Cutting His Own Income to Protect His Employees38:40 — The Deal That Almost Collapsed at the Finish Line48:40 — Signing a $50M Credit Line: The Ultimate Risk50:10 — Why the Top 1% Win: The Extra 10% Effort58:00 — Reputation: The One Asset You Can Never RecoverThis is one of the most value-packed, raw, and motivational episodes to date.If you’re between 20–40 and trying to figure out your next move, THIS is your roadmap. #entrepreneurship #RealEstateInvesting #MortgageLending #RiskyBusinessPodcast#BusinessMotivation #SuccessMindset #FinancialFreedom #PrivateLending#RealEstatePodcast #WealthBuilding #2008FinancialCrisis #RealEstateFinance#InvestingMindset #BusinessRisk #entrepreneurlife

    1h 13m

  8. 11/18/2025

    JAY PITTS: HOW TO CRUSH YOUR SALES VOLUME??

    Welcome back to the Risky Business Podcast! I'm extra excited for today’s episode because I’m sitting down with Louisville real estate legend, Jay Pitts (Jay T Pitts & Associates). Jay isn't just a top-selling agent; he leads one of the most productive brokerages in Kentucky, pushing over $500M in sales volume yearly. This conversation goes deep into the risk and strategy behind scaling a top-tier real estate business. Jay shares his incredible journey from a self-proclaimed "Type A, first-born" mortgage originator to leading a mega-team. Key Takeaways: ​The Biggest Risk: Why quitting a 6-figure mortgage job at 24 to become self-employed was the logical choice.​The 2008 Crash Pivot: How Jay used bank foreclosure listings (REOs) to build his initial momentum.​The Tipping Point: The moment his team had to suddenly scale from 12 to 30+ agents after securing a major Zillow partnership.​The Snowball Analogy: How consistent, hard work eventually creates an unstoppable avalanche of business (and why he prioritizes agents who "give without expectation").​Training AI: Jay breaks down his AI-powered market update podcast strategy.​New Agent Advice: The number one piece of advice for new agents, and why you should never make a career decision based on money.Connect with Jay Pitts: ​Podcast: The Jay Pitts Show​Instagram: @thejaypittsteam

    1h 8m
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Ratings & Reviews

5
out of 5
12 Ratings

About

Hearing from those who have taken BIG RISKS and finding out what they learned. Here to Encourage / Challenge / Push YOU to take that next RISK Hosted by: Sam Stone

Information

  • Creator
    Sam Stone
  • Years Active
    2024 - 2026
  • Episodes
    30
  • Rating
    Clean
  • Copyright
    © Sam Stone
  • Show Website
    Risky Business

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