Risky Business

Check out ShadyRays.com and use code SAMSTONE for 25% off! Sponsor Highlight: River City Mortgage LLC, NMLS 142954, https://rchomeloans.com/. Call or Text: Nick Hunter 513-490-4235. In this episode of The Risky Business Podcast, we sit down with Chris Ratterman, founder and CEO of Shady Rays, to explore how he turned a small business idea into a nationally recognized sunglasses brand. Timestamps: (01:07) Meet Chris Ratterman, Founder and CEO of Shady Rays, (01:59) What Is Shady Rays?, (02:57) The Idea Behind Starting a Sunglasses Brand, (03:23) Chris's First Business Idea in Grade School, (04:39) How Shady Rays Got Started, (05:59) Learning the Lean Startup Method, (06:57) Business Books That Inspired Chris, (07:31) River City Mortgage Sponsor Message, (08:21) Starting Shady Rays With $17,000, (08:54) Building a Business While Working Full-Time, (09:22) Reinvesting Everything Into Marketing, (10:42) The Day Shady Rays Overdrafted Its Bank Account, (11:26) Navigating Financial Challenges as an Entrepreneur, (12:22) Why Shady Rays Didn't Take Outside Investors, (13:41) Learning Every Part of the Business, (14:21) What Kept Chris Going Through Difficult Times, (15:11) The Twitter Marketing Strategy That Got Him Suspended, (17:19) The First Shady Rays Sale, (18:25) Advice for Young Entrepreneurs, (19:49) How to Start a Business From Nothing, (21:34) Why Entrepreneurs Need to Understand AI, (22:12) The Biggest Opportunities in AI, (23:07) How Business Owners Are Using AI, (25:03) Chris's Favorite AI Tools, (25:38) Practical Ways to Start Using AI, (27:39) How to Validate a Business Idea, (28:38) Finding the Gap in the Sunglasses Market, (29:33) Designing and Expanding the Shady Rays Product Line, (30:37) New Products, Collaborations, and Brand Partnerships, (32:01) Developing Performance Sunglasses, (32:49) Working With Professional Golfer Sahith Theegala, (33:37) How Big Has Shady Rays Become?, (34:01) Retail Stores, Employees, and Staying Independent, (35:49) Black Friday and Cyber Monday at Shady Rays, (37:06) The Charitable Mission Behind Shady Rays, (38:57) Lessons From St. Xavier High School, (40:14) What's Next for Shady Rays?

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

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 513-490-4235At 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 513-490-4235What 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.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

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 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