In the 53 episode of Simply Business, host John Jennings sits down with Shawn Herbig, founder of IQS Research and Bluegrass Bitters, to explore two very different entrepreneurial journeys—one rooted in analytics, and the other in artisanal flavor.

Shawn shares how he left a successful role at Ford Motor Company to chase a lifelong dream of business ownership. Over the past 25+ years, he’s built IQS Research into a respected data analytics firm—and more recently, decided to turn his hobby of crafting cocktail bitters into a second venture: Bluegrass Bitters.

This conversation dives into the reality of switching roles (sales, ops, management) within your own business, how AI is challenging the integrity of information, and why critical thinking has never been more important. Plus, hear how a research-minded entrepreneur builds a beverage brand from scratch—with obsessively detailed business planning, market insights, and just a splash of creative storytelling.

In this episode:

• Wearing all the hats (and which ones actually pay)
• The danger of scaling bad AI answers
• Why starting a second business is like starting over—with more wisdom
• Passion vs. execution: why you need both
• What every aspiring entrepreneur should do before launching

Whether you’re in data, drinks, or just dreaming of your next business move, Shawn’s insight is packed with practical wisdom.

In the 52nd episode of Simply Business, John Jennings sits down with Bill Reynolds, President of Element 502, to explore the raw and real journey of turning around a struggling marketing agency.

Bill opens up about how he went from a consultant to business owner overnight—after a leap of faith (and prayer) with his wife. He shares what happened when he lost his biggest client five days into ownership, how he led his team through some very challenging times, and why integrity, honesty, and relationship-first values have helped Element 502 thrive.

With a refreshingly transparent look at entrepreneurship, Bill explains what “Passengers, Not Hostages” really means, why marketing shouldn’t be the first budget cut, and how to navigate today's AI-influenced business world.

This episode is a masterclass in resilience, servant leadership, and staying true to your values in business.

👉 Tune in to learn:

• What makes a marketing agency really stand out
• How to lead a team through uncertainty
• The power of saying “no” to bad business
• Why entrepreneurs need accountability—even if they don’t like it

🎧 Listen now and be inspired by a story that proves heart, hustle, and humility still win.

In the 51 episode of Simply Business, host John Jennings sits down with Brady Jolly,

President and Owner of Jolly Plumbing Drains, Heating and Air.

Brady shares the remarkable story of taking over his family business, founded in 1979, and transforming it into a thriving, multi-service home solutions company in Northern Kentucky and Greater Cincinnati.

Brady discusses the challenges of leading a second-generation business, the bold transition from commercial to residential services, and navigating major industry shifts, including launching an HVAC division during the height of COVID-19.

He also provides key insights on leadership, company culture, and work-life alignment, including Jolly Plumbing’s groundbreaking decision to eliminate on-call work, prioritizing employee well-being.

This episode is packed with valuable lessons on scaling a business, leading through adversity, and building a company that prioritizes both employees and customers.

🎧 Listen now to hear:

✔️ The key to successfully transitioning a family business

✔️ Why company culture and employee happiness drive business success

✔️ How to embrace failure and pivot during uncertain times

✔️ The power of strategic growth and smart delegation

📢 Don’t miss this conversation filled with insights, inspiration, and practical takeaways for business owners and leaders alike!

In the 50th episode of Simply Business, host John Jennings sits down with Larry Baker, a real estate broker, investor, and entrepreneur who has built a thriving business across Kentucky, Indiana, and Florida. Larry shares his journey from sales—starting in the car industry—to becoming a top real estate agent, broker, and investor. He now leads a brokerage with over 40 agents and has built long-term wealth through smart real estate investing. In this episode, Larry breaks down:

The truth about being a real estate agent (vs. common myths) How he scaled his brokerage and built a multi-state real estate business The best strategies for investing in real estate—without making rookie mistakes The challenges of getting financing as a self-employed investor & how he worked around it His top advice for real estate agents looking to grow their business

Whether you’re considering a career in real estate or looking for smart ways to invest, Larry’s insights are packed with practical advice you can use today.

In this inspiring episode 49 of Simply

Business, host John Jennings welcomes Reverend Dr. Julie Hager

Love, the President & CEO of the Kentucky United Methodist

Children's Home.

With a background in theology, Christian education, and leadership

development, Dr. Love has dedicated her career to serving children and families

in need.

She shares insights on building trust in leadership, fostering

a strong workplace culture, and navigating the complexities of child

welfare.

Under her leadership, the Children’s Home has expanded its

services, providing residential care, support for foster youth aging out of the

system, and community-based programs to serve nearly 2,000 children and

families annually.

Key topics covered:

✅ Transitioning from clergy to CEO

✅ Creating a preferred workplace culture in a nonprofit setting

✅ The power of trust in leadership and team building

✅ Addressing child welfare challenges and shaping Kentucky’s future for

children

Dr. Love also shares a powerful personal story about making every

child feel like a “favorite” and ensuring they know they are loved, prayed for,

and valued.

Tune in for an inspiring conversation about servant leadership,

sustainable excellence, and making a difference in the lives of children.

In Episode 48 of Simply Business, host John Jennings sits down with Kyle Bush, Founder & CEO of Cumberland Creative, a 50+ award-winning video production and digital marketing agency.

Kyle shares his entrepreneurial journey, how he built a scalable storytelling business, and what it takes to create high-impact visual content that drives real revenue growth.

💡 Key Themes Discussed:

✅ The power of storytelling in branding & marketing

✅ Scaling a video production agency from the ground up

✅ The balance between creativity and business strategy

✅ How to make content that converts into business results

✅ Lessons on team leadership & entrepreneurship

From working with major brands to navigating the evolving digital landscape, Kyle breaks down what businesses need to know about effective video marketing and why great storytelling is at the heart of audience engagement.

In this episode of Simply Business, host John Jennings sits down with Clay Smith, a real estate investor and serial entrepreneur who has scaled multiple businesses from the ground up. Starting as a young entrepreneur selling candy bars and running a paper route, Clay evolved into a powerhouse in real estate, property management, and contracting.

He shares insights on:

✅ The key challenges of scaling multiple businesses while maintaining profitability

✅ Letting go of operations and empowering the right people to run the day-to-day

✅ The importance of KPIs in making business decisions and avoiding financial pitfalls

✅ How having an accountability partner (or business partner) can drive success

✅ Lessons learned from corporate IT to real estate – and how data-driven decision-making changed everything

Clay also dives into the myth of instant profitability—how explosive growth doesn’t always mean financial success and why business owners must keep a close eye on cash flow.

One of the biggest takeaways? “Keep your company as underfunded as you can. If there’s money sitting there, it will get used.”

Whether you're a real estate investor, a business owner, or an entrepreneur struggling to scale, this episode is packed with practical wisdom and hard-earned lessons that can help you grow smarter, not harder.

In this episode of Simply Business, host John Jennings sits down with Doug Lacy, Founder and President of Pivotal, a global IT field services company operating in 150+ countries. Doug shares the remarkable journey of scaling an IT services business, transitioning from a handful of clients to working with Fortune 500 companies worldwide.

Doug reveals key insights about:

• Overcoming the "founder’s trap" and navigating business plateaus
• The power of partnerships in scaling internationally
• Making the tough leap from low-margin to high-value clients
• Learning to ask for help and build a strong leadership team
• The relentless drive of entrepreneurship—why you’re never truly “done”

Doug’s story is a testament to the balance between strategy, patience, and execution. Whether you're a business owner, a startup leader, or scaling your operations, this episode is packed with wisdom on growth, resilience, and leadership.

🎧 Listen now! And don’t forget to subscribe, rate, and share with fellow entrepreneurs.

🔗 Visit pivital.com to learn more about Pivotal’s IT solutions.