Risky Business

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

https://lastingmark.com/

Life Insurance Academy

https://youtube.com/@lifeinsuranceacademy?si=gRxpBV7EEW4rwBIf

Follow Roger on Instagram

https://www.instagram.com/rogershort/

From a 9 year old knocking doors with his brother to cut lawns to a 7 figure business - 20 years of experience in lawn care - and now a successful podcast host, Scotty Scearce’s story is the perfect reminder that YOU ARE NEVER TOO YOUNG TO TAKE A RISK!

Scearce Lawncare

https://www.scearcelawncare.com/

The Life In Stride Podcast

https://open.spotify.com/show/3hAyALRNhRA7UfKPVpX2IU?si=iAmmSuZVT2KtpyxjBTj5Hw