Risky Business

Sponsor Highlight: River City Mortgage LLC, NMLS 142954, https://rchomeloans.com/. Call or Text: Nick Hunter 513-490-4235. In this episode, Sam Stone sits down with Roger Short to discuss the risk of moving to America to start a phone book company. After building a successful brand and company, Roger saw the change iPhone and Google were going to be on the Phone Book industry and took a risk again, jumping into insurance sales. Roger has grown to now having 2000+ agents at his company, Lasting Mark, and hosts his own podcast for insurance agents with over 100K listeners a month. Roger’s story of risk and faith will encourage you, but his love for his family and clients will challenge you to be better in whatever field you’re in. Roger's Company: Lasting Mark: https://lastingmark.com/. Roger's Podcast: Life Insurance Academy: https://youtube.com/@LifeInsuranceAcademy?si=gRxpBV7EEW4rwBIf. Follow Roger on Instagram: https://www.instagram.com/rogershort/. Timestamps: (0:28) Meet Roger Short, (1:41) Building a Successful Insurance Podcast, (4:20) Roger’s Entrepreneurial Background, (6:25) Studying Theology & Finding Sales, (8:00) His First Steps Into Business, (8:38) Selling Yellow Pages Advertising, (10:40) The Opportunity That Changed Everything, (12:01) Moving to America With Less Than $7,000, (14:01) Starting a Phone Book Company, (16:11) Selling a Product That Didn’t Exist Yet, (16:49) Bartering for Hotels & Food, (18:22) Growing the Business to $62 Million, (19:05) The Recession, iPhone & Google Change Everything, (20:09) Knowing It Was Time to Pivot, (21:50) Walking Away From the Company, (22:38) Discovering the Life Insurance Business, (23:55) The Client Meeting That Changed Roger’s Direction, (27:12) Building a Business That Makes a Difference, (29:10) Starting Over in Insurance, (30:44) Betting on Himself Again, (31:41) Building Lasting Mark, (33:39) Why Roger Takes Calculated Risks, (35:47) Understanding What Customers Really Need, (36:35) Ethos, Pathos & Logos in Sales, (39:11) Roger’s Personal Motivation for Taking Risks, (39:56) Advice From His Father-in-Law That Changed His Life, (40:43) Starting From Scratch in Insurance, (43:17) Why Life Insurance Became Personal, (45:09) The Meaning Behind Lasting Mark, (45:46) Christian Values in Business, (47:05) Managing a National Organization, (48:14) Building a Global Team, (50:18) Helping Agents Build Their Own Businesses, (53:00) How New Agents Can Get Started, (55:34) Roger’s Speaking Events & Leadership, (58:36) Roger’s Advice for Young Risk-Takers, (59:20) Take a Chance on Yourself, (1:01:13) Surround Yourself With the Right People, (1:02:18) What’s the Worst That Can Happen?, (1:03:08) Why Sam Needs to Keep Going, (1:04:18) The Commitment to 100 Episodes

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

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

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

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

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

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

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

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

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