Risky Business

Sam Stone
  • 5.0 (12)
  • Entrepreneurship
  • 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. Oct 5

    CRESTWOOD MERCANTILE - From Day Jobs to Dream Jobs w/ Karen Delaney & Lindsay Stivers

    Sponsor Highlight: River City Mortgage LLC, NMLS 142954, https://rchomeloans.com/. Call or Text: Nick Hunter 513-490-4235. 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. Timestamps: (0:49) Meet Karen Delaney & Lindsay Stivers, (1:15) Karen’s Career Before Crestwood Mercantile, (2:32) How COVID Changed Karen’s Career Perspective, (3:20) How Karen & Lindsay Met, (4:44) Lindsay’s 15-Year Career as a Speech Therapist, (5:39) How Lindsay Got Into Antiques & Vintage, (7:23) How Crestwood Mercantile Started, (8:37) The Original Business Idea, (9:50) Finding the Crestwood Building, (10:49) Seeing the Potential in the Space, (11:45) Going From One Floor to Three, (12:38) Opening Day: November 18, 2023, (12:51) Learning Commercial Real Estate the Hard Way, (13:23) The Contract That Almost Stopped the Business, (14:12) Months of Trying to Solve the Problem, (14:35) Lindsay Takes Matters Into Her Own Hands, (16:41) Building a Store With 70+ Vendors, (17:30) Creating a Curated Shopping Experience, (18:13) Getting 160 Vendor Applications, (19:42) How the Community Supported the Business20:48 How Sourcing Works, (23:43) Vintage, Antiques, New & Handmade Products, (25:04) How Social Media Drives Business, (27:02) The Most Rewarding Part of Owning the Store, (27:40) Building a Community, Not Just a Store, (33:46) Advice for Women Who Want to Take a Risk, (34:39) Why Passion Alone Isn’t Enough, (35:20) Leaving a Six-Figure Career, (36:05) Why You Need a Strong Business Plan, (37:09) Why Karen & Lindsay Work Well Together, (37:40) Don’t Take No for an Answer, (38:10) Surround Yourself With the Right People, (39:13) The Fear Behind Opening Day, (39:55) Customers Lined Up Around the Building, (40:57) What’s the Next Risk?, (43:05) Could Crestwood Mercantile Expand?, (44:12) Karen’s Cozy Cottage Business, (46:04) Growing Crestwood Mercantile on Social Media, (46:41) Why Unexpected Content Performs Better, (49:52) Final Advice for Future Entrepreneurs, (50:00) Don’t Be Afraid to Pivot, (50:26) You Can Restart Your Career, (51:48) Lindsay Lets Her Speech Therapy License Go

  2. Sep 28

    ROGER SHORT - From Phone Books to 2,000+ Agents: A Journey of Risk

    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

  3. Jul 29

    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

  4. Jul 7

    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

  5. Jun 2

    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

  6. Apr 30

    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. Timestamps0:00 Why taking risks matters0:33 Introduction to Ryan Richardson4:43 How the IV business started6:16 The moment everything clicked8:38 Moving states to build the business10:10 Scaling and hiring the first team11:46 Growing to hundreds of nurses16:03 Selling part of the business and stepping back17:07 Moving to Kentucky and starting over19:07 Leaving a stable job at American Express22:22 Fear and worst case scenario thinking24:48 Why helping people matters more than money27:07 Lessons from building multiple businesses28:11 Finding opportunities others miss29:04 Starting the sign company31:03 Scaling vs doing everything yourself33:50 Why presentation matters in business36:25 Marketing lessons from real estate signs39:30 The Cybertruck marketing strategy42:57 Why most people never take the leap45:24 Doubt, stress, and pushing through46:30 Scalability and building systems49:04 Hiring your first employee49:59 Final advice on risk and business

  7. 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

  8. 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

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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
    36
  • Rating
    Clean
  • Copyright
    © Sam Stone
  • Show Website
    Risky Business

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