What happens when you've already built a successful company, sold it for $20 million—and decide to start all over again?

For Nellie Akalp, the second time was much harder than the first.

In this episode of Simply Business, John Jennings sits down with Nellie, CEO of CorpNet, to talk about entrepreneurship, resilience, purpose, and what it really takes to build a business that lasts.

Nellie and her husband started their first company with just $100 from their Southern California apartment and eventually sold it to Intuit for $20 million. But retirement wasn't for her. She needed purpose, so they returned to entrepreneurship and built CorpNet.

This time, success didn't come easily.

Nellie shares what she learned from nearly a decade of struggle, why entrepreneurs have to become comfortable hearing "no," and why failure is very different from giving up. She also explains how CorpNet turned changing market conditions into opportunity, how the company is embracing AI without eliminating the human touch, and why great talent and culture remain critical as a business grows.

Perhaps the biggest lesson is also the simplest: you may not know what you're capable of until you're actually in it.

If you're building a business, struggling through a difficult season, or sitting on an idea you've been afraid to launch, this conversation is a reminder to keep testing, keep adapting, and keep knocking on doors.

Listen to the full episode, subscribe to Simply Business, and share it with an entrepreneur who needs to hear this message.

What happens when you leave the security of a large firm and decide to bet on yourself?

In this episode of Simply Business, John Jennings sits down with Steve Wallace, Managing Attorney and Founder of Wallace Law, a multi-state law firm serving clients across Florida, Texas, and New York. With more than 26 years of experience in bankruptcy, real estate, distressed assets, and business law, Steve brings both a legal perspective and the firsthand experience of a longtime small business owner.

Steve shares why he chose entrepreneurship over the traditional big-firm path, what it means to operate without a safety net, and why adaptability is essential to building a sustainable business. He and John also explore financial discipline, scaling responsibly, the challenges facing small businesses today, and the importance of knowing when to say no to the wrong client.

At the center of the conversation is one simple idea: believe in yourself enough to bet on yourself.

Steve also shares why he sees himself as a problem solver and deal-maker—not a deal breaker—and why serving the client's real goal matters more than simply generating billable hours.

If you're building a business, considering making the leap into entrepreneurship, or navigating uncertainty in your company, this conversation offers practical perspective from someone who has spent decades doing exactly that.

Listen to the full episode, subscribe to Simply Business, and share it with another business owner who needs the reminder that sometimes the best investment you can make is in yourself.

Is entrepreneurship the right next step—or is there a better path?

In this episode of the Simply Business Podcast, John Jennings welcomes Patrice Miles, Career Ownership Coach with The Entrepreneur's Source and host of the Journey to Business Ownership – Freedom Friday Podcast.

Patrice helps professionals navigate one of life's biggest career decisions by evaluating whether business ownership truly aligns with their goals, personality, financial objectives, and desired lifestyle. Whether someone wants to start a business, buy an existing company, or explore franchise ownership, her process is centered on education, clarity, and confidence.

In this conversation, you'll learn:

• How to know if business ownership is right for you
• The differences between starting, buying, and franchising a business
• Why due diligence matters more than excitement
• Common misconceptions about entrepreneurship
• How to build a career that creates freedom and purpose

If you're thinking about your next chapter—or simply want a realistic conversation about entrepreneurship—this episode offers practical wisdom that can help you make a better decision.

If you enjoyed this episode, subscribe, leave a review, and share it with someone who's considering becoming a business owner.

What does it really take to build a business from scratch?

In this episode of the Simply Business Podcast, John Jennings sits down with Ben Engel, owner of JBT Cleanout, to discuss the realities of entrepreneurship, building momentum, and creating opportunities through action.

Ben shares how he launched his company, the lessons he's learned along the way, and why networking, continuous learning, and surrounding yourself with the right people have become the foundation of his success.

They also discuss:

• Starting a business without waiting for perfect timing
• Building confidence through experience
• Marketing through relationships and social media
• Growing multiple businesses
• Leading people while continuing to learn yourself
• Developing the mindset to overcome criticism and setbacks

Whether you're launching your first company or looking to grow the one you already have, this conversation offers practical advice and genuine encouragement from someone building it in real time.

If you enjoyed this episode, be sure to subscribe, leave a review, and share it with another business owner who would benefit from the conversation.

In this episode of Simply Business, we sit down with Jesse Bray, CEO of Quantum Enterprises, to talk about what it really looks like to step into ownership of an existing business.

This isn’t a startup story — it’s something different.

Jesse shares his experience of acquiring a company he was already familiar with — and how quickly things change when the responsibility becomes yours.

We dive into the shift from employee to owner, the pressure of making decisions without a fallback, and the challenge of leading a business with its own history, team, and expectations.

This is a candid conversation about ownership — not in theory, but in practice — and what it demands from you as a leader.

👉 If you’re considering buying a business or stepping into a larger leadership role, this episode gives you a real-world perspective on what that transition requires.

What does it really take to leave corporate life and build something of your own?

In this episode of Simply Business, John Jennings sits down with Doug Gardner, owner of City Wide Facility Solutions of Louisville, to talk about entrepreneurship, calculated risk, and the realities of building a company over the long haul.

Doug shares his journey from finance and medical sales into business ownership, why he chose the franchise route, and what he learned after nearly 14 years of growth.

Inside this conversation:

✔ Taking the leap from employee to entrepreneur ✔ Why franchising isn’t the “easy button” ✔ The importance of capital planning ✔ Delayed gratification in business growth ✔ Building systems and strong teams ✔ Growing brand recognition and planning for the next decade

Doug’s message is refreshingly simple:

Business success isn’t instant.

It takes risk. Patience. Sweat. And the willingness to bet on yourself.

If you’re thinking about entrepreneurship—or already in the middle of the journey—this episode delivers practical wisdom and encouragement.

Subscribe, listen, and join us for more conversations that simplify business.

Have you ever looked up in June or July and thought, "We've been busy this year... but what have we actually accomplished?"

In this solo episode of Simply Business, John Jennings explores a challenge that many business owners and leadership teams face at the halfway point of the year: mistaking activity for momentum.

Most organizations begin the year with clear goals and a focused strategy. But as the months pass, new opportunities emerge, customer requests increase, priorities multiply, and urgent issues demand attention. Before long, teams are working hard, calendars are full, and everyone is busy—but meaningful progress can begin to stall.

John discusses what he calls the "illusion of momentum," the hidden dangers of overcommitting, and why leaders often struggle not with bad ideas, but with too many good ideas arriving at the wrong time.

He also explores how urgency can quietly take control of an organization, pulling attention away from strategic priorities and creating a cycle of constant reaction instead of intentional leadership.

As part of your own midyear review, John offers two powerful questions to consider:

• What are we doing today that seemed important three months ago, but no longer moves the business forward?

• If we could only accomplish three things between now and the end of the year, what would they be?

The businesses that finish the year strong aren't necessarily the busiest. They're the ones with the discipline to protect focus, align their teams, and make meaningful progress on what matters most.

Listen in for practical leadership insights that can help you regain clarity, sharpen priorities, and build momentum for a strong finish to the year.

Subscribe to Simply Business for more conversations and ideas that help business owners simplify leadership, strengthen strategy, and grow healthier businesses.

What happens when an entrepreneur leaves the corporate technology world and joins a family business dedicated to caring for seniors?

In this episode of Simply Business, John Jennings sits down with Marcus O'Malley, Owner and Director of Caring Excellence Northern Kentucky. Marcus shares his journey from software development and corporate leadership into the world of senior home care, where he now helps families navigate one of life's most important challenges—caring for aging loved ones.

Marcus discusses how personal experiences, including the loss of his mother, gave him a deeper appreciation for the needs of seniors and their families. He also explains how Caring Excellence has grown into a unique family-operated organization expanding across Kentucky while maintaining a commitment to personalized, compassionate care.

The conversation explores entrepreneurship, family business dynamics, leadership, AI in small businesses, and the importance of building trust through exceptional service.

In this episode, you'll learn:

• How personal experiences can shape meaningful business opportunities

• The realities of leaving corporate life to become an entrepreneur

• Why family businesses can be powerful growth platforms • How AI can improve operations without replacing human connection

• What it takes to build trust in a service-based business

• Why senior care remains one of the most important and resilient industries today

If you're an entrepreneur, business leader, caregiver, or someone considering a leap into business ownership, this conversation offers valuable insights and inspiration.

Be sure to subscribe, leave a review, and share this episode with someone who could benefit from Marcus's story.