Small businesses don’t fail because they lack passion or effort—they fail because they’re making decisions without clarity.

In this episode of The Winners Circle Podcast, host Jay Adewole sits down with Courtney De Ronde, CEO of Forge Financial & Management Consulting and creator of the Simple ScaleUp System™, for a practical, eye-opening conversation on how business intelligence can unlock massive growth for small businesses.

With over 20 years as a CPA and 15 years in business leadership, Courtney helps founders move beyond guesswork and intuition by using the right data to make smarter, more confident decisions. She breaks down business intelligence in a way that’s approachable, actionable, and immediately useful—no complex dashboards or corporate jargon required.

In this episode, you’ll learn:

• What business intelligence really means for small businesses
• The core data points every founder should be tracking from day one
• How to stop reacting to problems and start leading proactively
• How BI improves profitability, cash flow, and performance
• When a business is truly ready to scale—and how data reveals it
• How to build a data-driven culture without overwhelming your team

This conversation is for founders, CEOs, and leaders who want to scale with confidence, make better decisions, and turn insights into real business wins.

If you’re ready to replace guesswork with clarity and lead your business with intention, this episode will change how you see your numbers—and your growth potential.

🎧 Listen now on all Winners Circle Podcast platforms.

What if your creativity didn’t have to stay a passion—but could become a profitable, sustainable career?

In this episode of The Winners Circle Podcast, Jay Adewole sits down with Tim Packer, founder of Tim Packer Art Academy, to unpack what it truly takes to turn artistic talent into consistent income—without sacrificing authenticity or creative freedom.

Tim is an artist, educator, and entrepreneur who has helped countless creatives develop their skills, build strong personal brands, and create multiple income streams from their art. Blending real-world business strategy with deep respect for the creative process, Tim shows artists how to move beyond “hoping it works” and start building careers that last.

This conversation goes beyond inspiration. It’s a practical roadmap for artists who want to stop struggling financially and start treating their creativity like the business it deserves to be.

In this episode, you’ll learn:

• Why talent alone isn’t enough—and what artists must add to succeed
• The first steps to monetizing your art with confidence
• How to price your work without undervaluing yourself
• Ways artists can build multiple income streams beyond originals
• How to market your art without feeling “salesy”
• The mindset shifts required to thrive creatively and financially
• How to balance artistic integrity with smart business decisions
• What a truly sustainable art career looks like long-term

Tim also shares how artists can navigate fear, rejection, and overwhelm—while building systems that support growth, stability, and fulfillment.

Whether you’re a painter, illustrator, digital artist, creative entrepreneur, or someone sitting on untapped talent, this episode will challenge how you think about art, money, and success.

🎧 Listen now on all Winners Circle Podcast platforms and discover how creativity, strategy, and entrepreneurship intersect to turn talent into income—on your own terms.

What truly separates founders who struggle to raise capital from those who scale transformative companies? It’s not just the idea—it’s the connection between entrepreneurs and investors.

In this episode of The Winners Circle Podcast, Jay Adewole sits down with Scott Kelly, Founder & CEO of Black Dog Venture Partners, for a masterclass on how innovation, capital, and trust intersect.

With more than three decades of experience working on both sides of the table, Scott has helped founders refine their vision, sharpen their pitch, and access the right investors—while also guiding investors toward high-potential opportunities that sustain long-term innovation. His work bridges the gap between bold ideas and smart capital.

Scott is widely known as the organizer and MC of VC Fast Pitch, where entrepreneurs connect directly with some of the world’s top investors, and as the host of the Emerging Managers Podcast, a show exploring why new and emerging VC funds may represent the next great investment opportunity.

In this conversation, Scott shares deep insights from training thousands of salespeople, building investor networks, and watching firsthand what makes founder–investor relationships succeed—or fail.

In this episode, you’ll learn:

• Why the entrepreneur–investor relationship is the foundation of scalable innovation
• How founders can position themselves to attract the right investors—not just capital
• What investors actually look for beyond the pitch deck
• Common mistakes founders make when approaching investors
• How trust, alignment, and communication drive long-term success
• The evolving role of emerging fund managers in today’s VC landscape
• How platforms like VC Fast Pitch accelerate meaningful connections

This episode is a must-listen for founders raising capital, investors seeking differentiated deal flow, and entrepreneurs who want to understand how money, innovation, and execution truly work together.

🎧 Listen now on all Winners Circle Podcast platforms and discover how powerful connections—not just capital—build winning companies.