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
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?
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Instagram: @LouisvilleKYRealEstate
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https://www.louisvillepodcast.studio/
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
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:
Connect with Jay Pitts:
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
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
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.
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.
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.
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.
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.
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
On this episode of Risky Business, Sam Stone sit down with Clark Burckle: Clark is a former NCAA national champion and represented Team USA in the 2012 Summer Olympics. After competing at the highest level, he took his drive and discipline to Stanford, earning an MBA before returning home to Louisville to pursue entrepreneurship.Now, he's the owner of Different Strokes Golf Center,a cutting-edge golf facility that’s expanded to multiple locations. Clark’s story is a masterclass in reinvention, grit, and what happens when you take the leap from elite athlete to visionary business owner. This episode will challenge you to think bigger and take the risks you've been putting off.
Come behind the scenes of Crestwood Mercantile with co-founders Karen Delaney and Lindsay Stivers. After more than 15 years in their careers, they made the bold decision to walk away and chase a dream. What began as a side hustle has now grown into a 15,000 sq. ft. store packed with over 75 vendors, offering everything from thrifted gems to brand-new finds.
Their journey is a powerful reminder that big risks can lead to even bigger rewards. This episode is packed full of never before heard stories about the origin of Crestwood Mercantile and how Karen and Lindsay brought their vision to life. Thanks for listening and check them out on Instagram @CrestwoodMercantile
Host Sam Stone sits down with Ryan Cornell, Louisville native and founder of Handsome Fellows—widely recognized as the number one rated barbershop in the city, with multiple thriving locations.
Ryan and his barbers aren’t just cutting hair—they are redefining the experience. With a deep respect for both clients’ and barbers’ time, he’s built a culture of high-level service where a haircut becomes something you plan your day around. It’s not just grooming—it’s an experience.
Ryan shares how his journey—from a background in sales to building a standout brand—was shaped not just by ambition, but by hard-earned life lessons. He opens up about using personal setbacks as fuel, and how embracing your past can be the foundation for starting something meaningful.
This conversation dives into taking risks early, the power of supportive family and friends, and the importance of choosing the right people to surround yourself with in business. Whether you’re an aspiring entrepreneur or simply navigating your own leap of faith, this episode is full of candid wisdom and real-world encouragement.
Listen, share, and tag someone who needs that extra push to take the risk.
On this episode of The Risky Business Podcast, Sam Stone interviews serial entrepreneur and investor Todd Earwood, a man who treats business like a sport—testing over 150 ideas, launching 18 companies, and selling three, including a major exit in 2023. From founding a web video company before YouTube to co-launching a VC fund with over 100 AI investments, Todd shares the bold bets, brutal lessons, and surprising wins from a life spent chasing innovation. He opens up about the time he nearly lost his house while self-funding a startup—only to secure millions in investment just 12 days after receiving a foreclosure letter. This episode is packed with real talk about risk, resilience, and the relentless pursuit of building something meaningful.
In this episode of The Risky Business Podcast, host Sam Stone sits down with his father, Dave Stone—former Senior Pastor of Southeast Christian Church, one of the largest churches in America. With over 30 years of ministry experience, Dave opens up about the risks and leadership challenges of guiding a massive organization through seasons of change. Together, Sam and Dave also explore what it means to live generously, even when it feels uncertain or costly.
This conversation is raw, inspiring, and deeply personal. You’ll leave encouraged, challenged, and maybe even a little emotional.
Going All In with Peyton Siva: From Player to Coach to Entrepreneur
In this episode of Risky Business, Sam Stone sits down with Louisville basketball legend Peyton Siva to talk about what it really means to go all in. From winning at the highest level as a player to taking the leap into coaching under Pat Kelsey at the University of Louisville, to launching his own basketball training facility — Shoot 360 — Peyton shares the mindset, struggles, and risks behind betting on yourself.
With 10 years of pro ball under his belt, including time in the NBA and overseas, Peyton brings a rare perspective on pushing through doubt, staying the course, and turning passion into purpose. Whether you're chasing a dream in sports, business, or life — this episode will challenge you to take the risk, go all in, and believe that you're worth the investment.
Brad Pierce is the Founder - Loudlux (2018-today) which is a well recognized film production company serving clients like Celsius, Michelob Ultra, Anheuser-Busch, Toyota, AirBnB.
He is also the Co founder - Human sync (2022-today) which focuses on longevity medicine. Building the first all in one preventive healthcare model.
Sam Stone and Brad Pierce spend this episode discussing how Brad has achieve so much at the age of 26 (Hint: he’s taken a few risks)
Roger Short sits down with Sam Stone to discuss the Risk of moving to America to start a phone book company. After building a successful brand and company he saw the change IPhones and Google were going to be to the Phone Book industry and took a risk again, jumping into Insurance sales. Roger has grown that to now having 2000+ agents at his company (Lasting Mark) and host a podcast for insurance agents with over 100K listeners a month. (Life Insurance Academy)
Roger’s story of Risk/Faith will encourage you, but his love for his family and clients will challenge you to be better in whatever field you’re in.
Lasting Mark
Life Insurance Academy
https://youtube.com/@lifeinsuranceacademy?si=gRxpBV7EEW4rwBIf
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