Risky Business

Sam Stone

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

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20 episodes
Updated July 29

Episodes20

Newest first

July 29 · 47 min
GUDGROOVE - Jaden Wagner - Building a Brand, Making Music, and Sharing a Stage with DIPLO
Sponsor 1: Today’s episode is sponsored by LG&E and KU, who are helping local businesses save money through tailored business energy efficiency programs. From cash-back rebates for upgrading equipment to no-cost small business energy audits and customized demand response plans, LG&E and KU provides the smart solutions your business needs to save. Visit ⁠lge-ku.com/eebusiness (https://lge-ku.com/energy-efficiency-programs#c-tabs-horizontal-90151__panel-90146)to learn more. Sponsor 2: River City Mortgage LLC NMLS 142954 https://rchomeloans.com/Call or Text: Nick Hunter 513-490-4235 At 19 years old, Jaden Wagner, professionally known as GudGroove, is already building a growing career as a DJ, electronic music producer and creative entrepreneur.In this episode of The Risky Business Podcast, host Sam Stone talks with Jaden about leaving baseball behind, teaching himself music production and continuing to post his work even when people criticized him.Jaden shares how social media helped him build an audience, what he learned from performing with Diplo and why preparation matters when playing in front of thousands of people. They also discuss personal branding, creative direction, supportive friendships, learning through failure and taking risks before you feel completely ready. Timestamps:0:00 Episode Preview0:30 Welcome to The Risky Business Podcast0:42 Introducing Jaden Wagner and GudGroove1:16 Building a Music Career at 192:16 GudGroove’s Music and Kentucky Releases3:14 Why Sam Wanted to Share Jaden’s Story3:42 Choosing Music Over the Traditional Path3:52 Jaden’s Original Plan to Play College Baseball4:19 Discovering DJing at Western Kentucky University5:17 Falling in Love With Controlling the Energy of a Room5:35 Learning What Professional DJs Actually Do5:50 Practicing With His First DJ Controller6:36 Mixing Music in the School Parking Lot6:59 Performing at a High School Football Tailgate7:26 Posting His First Mashups on TikTok7:33 Getting Criticized by Other Students7:57 Continuing Even When People Made Fun of Him9:04 Why Embarrassment Should Not Stop You10:24 Ignoring Other People’s Opinions11:22 Taking Risks Before Others Understand the Vision12:32 When Music Became More Than a Hobby13:19 How DJ Vice Encouraged Jaden to Produce Music13:35 Teaching Himself Ableton14:06 Creating the “New Drop” Remix14:16 Receiving 40,000 Streams Overnight14:42 The Moment Jaden Chose Music Over Baseball15:52 Telling His Father About His Decision16:18 Meeting Shanks Through TikTok16:27 Producing a Dance Remix of “Luther”16:45 Getting Played on Radio and Diplo’s Revolution18:14 Why Repetition Is Necessary for Success18:53 What Goes Into Producing and Mixing Music20:28 Using Social Media to Build a Personal Brand21:16 Why Artists Need to Show Their Personality22:19 Performing at a Louisville Kings Game22:39 Playing in Front of 11,000 People23:06 Preparing for a 15-Minute Stadium Performance24:28 Hearing Fans Sing “Take Me Back to Kentucky”25:22 Lessons From Sharing the Stage With Major Artists25:35 Jaden’s First Performance With Diplo27:39 Meeting Olivia Dunne During the Show28:07 Getting Asked to Close for Diplo29:26 Performing Back-to-Back With Diplo31:15 Preparing to Perform With Diplo Again32:18 Jaden’s Five-Year Vision32:53 Taking Creative Risks With New Music34:10 Why Young People Should Start Taking Risks Today35:34 Learning Through Failure36:18 GudGroove’s Music and Social Media37:29 How “Louis Bag” Was Created38:54 Creative Direction and Building a Visual Brand40:31 Creating the “You Don’t Know My Name” Music Video43:23 The Importance of Supportive Friends44:00 Celebrating Career Milestones45:31 Finding GudGroove’s Signature Sound46:49 Closing Thoughts47:12 Take the Risk
July 7 · 39 min
The Secret to Social Media Isn't Talent. It's This. - w/ SAM STONE
What does it actually take to turn social media into real business?In this solo episode of the Risky Business Podcast, Sam Stone breaks down how he used social media to build his real estate brand, grow a large local audience, and turn attention into real clients.Sam shares why attention is the new currency, why people cannot buy from you if they do not know you exist, and why the goal is not just followers, but trust. He also explains how consistency, trial reels, storytelling, and documenting your life can create opportunities you cannot predict.This episode is a practical crash course for anyone building a business, personal brand, or audience online.If you are trying to grow on social media, build trust, and create real opportunities from your content, this one is for you. Sponsor 1: Today’s episode is sponsored by LG&E and KU, who are helping local businesses save money through tailored business energy efficiency programs. From cash-back rebates for upgrading equipment to no-cost small business energy audits and customized demand response plans, LG&E and KU provides the smart solutions your business needs to save. Visit ⁠lge-ku.com/eebusiness (https://lge-ku.com/energy-efficiency-programs#c-tabs-horizontal-90151__panel-90146)to learn more. Sponsor 2 Highlight: River City Mortgage LLCNMLS 142954https://rchomeloans.com/Call or Text: Nick Hunter 513-490-4235
June 2 · 45 min
Brice Herron: All in on Social Media - Is it Worth It
Sponsor Highlight: River City Mortgage LLCNMLS 142954https://rchomeloans.com/Call or Text: Nick Hunter 513-490-4235 What happens when you decide to challenge yourself publicly and build a business at the same time?In this episode of the Risky Business Podcast, Sam Stone sits down with Brice Herron to talk about the Run the Date Challenge, building Vail Nutrition, and what it looks like to start something while you are still in the middle of the climb.Brice shares why he started running every day, how his videos started gaining traction online, and how that audience has connected with the nutrition company he is building. He also talks about being a firefighter, learning through social media, creating content consistently, and developing a product he actually believes in.They dive into taking action before everything is perfect, building a network, producing more than you consume, and what it takes to keep moving when life gets difficult.This is a conversation about discipline, risk, content, business, and starting before you feel ready.Timestamps0:00 Introduction to Bryce Harren0:50 Starting the Run the Date Challenge2:12 What the challenge actually is3:26 Preparing for the running challenge4:08 Posting every day for accountability5:08 Growing on social media6:19 First video taking off7:53 Being nervous to post online9:06 How his content changed over time10:37 Starting Veil Nutrition11:15 Solving the fueling problem for runners12:44 Barriers to launching a nutrition product13:48 Taking longer than expected to launch14:27 Creating a product that stands out15:12 Combining content with business15:46 Why he stopped posting every day16:42 Inspiration from Casey Neistat17:29 The time commitment of editing videos19:13 Learning what works on social media20:41 Building an audience before launch22:03 Turning attention into opportunity23:51 Getting Veil Nutrition in front of people25:02 Starting before you know everything26:04 Funding and next steps27:22 Connecting with the running community28:13 Filming runs in public29:46 Building a network in Louisville33:14 Why people need to know you first37:01 Produce more than you consume39:18 Taking accountability and figuring it out40:27 Getting the product launched42:31 Final advice and where to follow Bryce43:23 The final run of the year44:08 Being in the middle of the climb
April 30 · 51 min
Ryan Richardson: From Real Estate to Scaling a 9-State Business
Sponsor Highlight: River City Mortgage LLC NMLS 142954 https://rchomeloans.com/ Call or Text: Nick Hunter 513-490-4235 What does it actually look like to bet on yourself and build something real? In this episode, Sam Stone sits down with Ryan Richardson to break down his journey from working at American Express to building multiple businesses, including scaling a mobile IV company across multiple states. Ryan shares how he took his first big risk leaving a stable job, why most people never make that jump, and what actually happens after you do. They dive into building systems, hiring your first employee, and why focusing on helping people always beats chasing money. They also talk about scaling, business mistakes, real estate, and how to identify opportunities most people overlook. If you’ve ever thought about starting something but haven’t taken the leap, this one will hit. Timestamps 0:00 Why taking risks matters 0:33 Introduction to Ryan Richardson 4:43 How the IV business started 6:16 The moment everything clicked 8:38 Moving states to build the business 10:10 Scaling and hiring the first team 11:46 Growing to hundreds of nurses 16:03 Selling part of the business and stepping back 17:07 Moving to Kentucky and starting over 19:07 Leaving a stable job at American Express 22:22 Fear and worst case scenario thinking 24:48 Why helping people matters more than money 27:07 Lessons from building multiple businesses 28:11 Finding opportunities others miss 29:04 Starting the sign company 31:03 Scaling vs doing everything yourself 33:50 Why presentation matters in business 36:25 Marketing lessons from real estate signs 39:30 The Cybertruck marketing strategy 42:57 Why most people never take the leap 45:24 Doubt, stress, and pushing through 46:30 Scalability and building systems 49:04 Hiring your first employee 49:59 Final advice on risk and business
March 27 · 39 min
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
March 2 · 54 min
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
February 10 · 45 min
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
January 29 · 45 min
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
January 4 · 35 min
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
Dec 23, 2025 · 1 hr
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 Stone Instagram: @LouisvilleKYRealEstate Follow Cameron Becht / Louisville Podcast Studio https://www.louisvillepodcast.studio/
Dec 3, 2025 · 1 hr 12 min
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
Nov 18, 2025 · 1 hr 7 min
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
Nov 6, 2025 · 54 min
Female Entrepenuers....This is the Podcast For You | The Top Photographer of 30A
Female founders, this one’s for you. 🎥💍 Meet Hannah Elise Photo — the Panhandle’s go-to wedding & family photographer (Destin, Seaside, 30A, Panama City, Pensacola) who turned a side hustle into a globe-trotting creative business. We cover: starting without resources, landing viral wedding videos (10M+ views), pricing & gear realities, client experience, taking a 100-day national parks RV road trip, and the mindset shifts it takes to bet on yourself.We also jam on productivity with Brick (the little magnet that locks you out of distracting apps) and why boundaries = more art, more revenue, more life.Listen for: how to start before you’re ready, what to buy (and NOT buy) as a beginner, social growth that actually books clients, and the courage it takes for women to choose the “risky” path.👇 Links & Resources• Hannah on IG: https://www.instagram.com/hannahelisephoto?igsh=c29mbWdyMThlamFj• Book Hannah for weddings/family sessions: • Brick productivity tool (affiliate): https://getbrick.app – code SAM47683 for ~20% off• Risky Business Podcast site: https://riskybusinesspodcast.com/If this gave you a nudge, subscribe, like, and share with a friend who needs to take that next step. Comment your #1 takeaway and I’ll reply.Female entrepreneur, wedding photographer Destin, 30A family photos, Florida Panhandle photographer, viral wedding video, photography gear list, how to price photography, client experience, Instagram growth for photographers, TikTok photography tips, Brick phone blocker, productivity for creators, national parks RV road trip, Bob Jones University, Liberty University, social media marketing, small business risk, start before you’re ready#FemaleEntrepreneur #WeddingPhotographer #30A #Destin #PhotographyBusiness #CreatorEconomy #SmallBusiness #ViralMarketing #Productivity #Brick #RVLife #NationalParks #RiskyBusinessPodcast
Oct 22, 2025 · 1 hr 4 min
THADDEUS VOSS - From Wall Street to $25M by 29: How he Built Bluegrass Lending
Risky Business Podcast 🎙️Today, Sam sits down with Thaddius “Thad”—Louisville native who went commission-only in NYC, survived the 2020 shutdown, and built Bluegrass Lending + Lionheart to manage $25M+ in assets by 29. We talk TikTok lead gen for real estate, alternative vs. traditional funding, SOPs, focus vs. shiny objects, lessons from an Alex Hormozi workshop, and why your 20s/30s should be a machine for mistakes.🔔 If this episode pushed you to take a (calculated) risk, rate, follow, and share—it’s the #1 way to grow this show.👥 GuestBluegrass Lending / Lionheart (brokerage + private funding)— Alternative & SBA loans, credit repair/bookkeeping support, high client return rate— Offices: Louisville KY • Wall Street NYC • Tempe AZ💬 Topics• Winning listings with TikTok reach• Alternative financing vs. SBA/asset-backed loans• Building returning clients by educating, not hard-selling• Systems, lead gen, and scaling a sales org• Focus, attention, and the “Brick” phone blocker• How to take risk without being reckless
Oct 13, 2025 · 50 min
BRAD DEVRIES - Walking Away from a Dream Job at 33 - Building a Life that Matters
At 33, Brad DeVries had it all lined up - a pilot job at UPS and the kind of career most people dream about. But just days before starting, he realized something: he didn’t want to fly airplanes. He wanted to build people.In this episode of Risky Business, Brad shares how that one moment of honesty changed everything - leading to a 30+ year career leading 3 of the largest real estate brokerages, and later, taking a massive risk again in his 60s to start not one but two new businesses.From leaving comfort behind to listening for God’s direction, this is a masterclass on calling, courage, and purpose. Whether you’re 25 or 65, this story proves it’s never too late to take a risk that matters.
Oct 2, 2025 · 45 min
SCOTT PANELLA - GIVE A GOAT
What does it take to turn an adoption journey into a movement that feeds families, creates jobs, and reshapes an entire community? Sam sits down with Scott Panella, Louisville real estate leader and founder of Give a Goat, to unpack how a mission trip and adoption experience in Uganda grew into a nonprofit that has provided thousands of goats, wells, and sustainable food sources for families in need.Scott shares the raw challenges of adopting internationally, balancing business while living abroad, and learning an entirely new world of goat farming and community development. They dive into fundraising highs and lows, building a 100% Ugandan-led team, and why small gifts can create generational impact.If you’ve ever wondered how to align faith, risk, and entrepreneurship to create lasting change, this episode is both inspiring and practical. https://www.giveagoat.org
Sep 24, 2025 · 47 min
DANIEL CAMERON – Risk, Faith & Running for U.S. Senate
What does it take to walk away from a secure legal career, withstand media firestorms, and jump headfirst into one of the toughest Senate races in the country? Sam sits down with Daniel Cameron, former Kentucky Attorney General and U.S. Senate candidate, to unpack the calling, conviction, and courage that fuel his run for public office.Daniel shares how losing the governor’s race reshaped his faith, why his identity must rest in Christ rather than titles, and the lessons he’s learned balancing bold truth-telling with grace in the political arena. They discuss raising a young family in the chaos of campaigns, Kentucky’s critical role in America’s energy future, and how to re-open meaningful dialog in an age of polarization.If you care about leadership, calling, and what it means to take risks that matter, this conversation is both challenging and deeply encouraging.
Sep 12, 2025 · 1 hr 5 min
Bryce Morrison - The Risk Behind “Mom Water”
What does it take to turn a summer vacation idea into a breakout beverage brand? Sam sits down with Bryce Morrison, co-founder of Mom Water and Dad Water, to unpack the scrappy beginnings, bold branding bets, and operational grit behind their fast-growing, better-for-you alcoholic beverages. Bryce shares the origin story, early scrapes with supply chains and distribution, how they built a community first brand without the usual clichés, and the lessons he’s learned about partnerships, pace, and making decisions under pressure. If your goal is to build anything this conversation is a masterclass in taking smart risks, staying relentlessly simple, and scaling without losing your brand.
Aug 27, 2025 · 33 min
Eric Wood - NFL Pro Bowler helping you find out “What’s Next” in your life
Sam Stone sits down with Eric Wood — former Pro Bowl center for the Buffalo Bills, longtime NFL veteran, broadcaster, podcast host, and fierce competitor in everything he does. Eric opens up about life in the trenches of the NFL, the mindset it takes to compete at the highest level, and how he transitioned from professional athlete to respected voice in broadcasting and podcasting. From leadership in the locker room to resilience off the field, Eric shares stories and lessons that go far beyond football. If you’re an athlete, entrepreneur, or anyone chasing a bigger life, this conversation is packed with wisdom on taking risks, finding purpose, and staying hungry no matter what comes next.
Jul 30, 2025 · 1 hr 5 min
Kendall Bailey - Risking the Algorithm with @Kendall_in_Kentucky
In this episode of the Risky Business Podcast, Sam sits down with Kendall Bailey, better known online as “Kendall in Kentucky.” With a social media following of nearing half a million people, Kendall has built a bold platform around being unapologetically pro-life, pro-family, and outspoken about her Christian faith. We talk about what it means to take risks in the digital age, how she handles backlash, and why standing firm on your convictions might be the riskiest and most rewarding thing you can do. https://www.instagram.com/kendall_in_kentucky?igsh=MTIxeHNiaTE1eXFz