The Founders Hustle

Find Your Opposite - Kenny Leonard’s Best Advice for Entrepreneurs

What’s one piece of advice Kenny Leonard would give any entrepreneur? Find your opposite. In this episode of The Founders Hustle, Kenny shares how complementary strengths helped him and his business partner build Element 22 into a thriving commercial lending company. But that’s just one of many lessons packed into this conversation. Judy and Kenny dive into the realities of launching a business, including the financial risks, the early uncertainty, the importance of team trust, and why great leaders must be willing to make hard calls. This episode is especially valuable for founders, managers, and aspiring entrepreneurs who want honest insight into what sustainable growth actually looks like. You’ll hear: 1. how Kenny identified a gap in the market 2. why he bet everything on the business 3. what nearly caused them to quit 4. how to know when it’s time to let someone go 5. why relationships still matter more than technology A thoughtful, practical episode for anyone building a business with intention. Connect with Kenny on Linedin: https://www.linkedin.com/in/kenny-leonard-mba-4b884a6/ [https://www.linkedin.com/in/kenny-leonard-mba-4b884a6/] #EntrepreneurMindset #FounderAdvice #LeadershipPodcast #BusinessOwner #TheFoundersHustle #Element22 Support the show [https://buymeacoffee.com/thefoundershustle] If you’d like to toss a one-time “thank you” or grab a GRIT Happens sticker, you can do that by clicking the "Support The Show" link above or visit: https://buymeacoffee.com/thefoundershustle [https://buymeacoffee.com/thefoundershustle] * Watch & Subscribe on YouTube: https://www.youtube.com/@TheFoundersHustle [https://www.youtube.com/@TheFoundersHustle]   * Listen & Join our email community: https://www.thefoundershustle.com [https://www.thefoundershustle.com]   * Connect with the host, Judy Swafford, on LinkedIn: https://www.linkedin.com/in/judyswafford [https://www.linkedin.com/in/judyswafford]   * Get on the podcast: https://tinyurl.com/3fwb7bny [https://tinyurl.com/3fwb7bny]

How Cecily Built a Travel Business While Working Full-Time

Starting a business is hard. Building one while working full-time and raising a family takes another level of determination. In this episode of The Founders Hustle, Judy sits down with Cecily North-Rudow to talk about her entrepreneurial journey, from feeling stuck in her career to launching Traveling North Agency and creating a business around customized, high-touch travel planning. Cecily shares the real behind-the-scenes story: booking her first client, making mistakes, struggling to get traction, stepping away, and eventually coming back with more clarity about marketing, networking, and who she actually wanted to serve. This episode is a great listen for anyone who wants to start a business but feels like life is already full. Cecily’s story proves that growth does not have to look perfect to be real. You’ll hear about: *  Building a business alongside a full-time job  *  Why word of mouth alone was not enough  *  How content and local marketing helped her grow  *  The value of community and ongoing education  *  Why niche clarity can change everything   Every business has a backstory — and Cecily’s is full of lessons for entrepreneurs learning to build with patience and purpose. Visit: https://travelingnorthagency.com [https://travelingnorthagency.com] Support the show [https://buymeacoffee.com/thefoundershustle] * Watch & Subscribe on YouTube: https://www.youtube.com/@TheFoundersHustle [https://www.youtube.com/@TheFoundersHustle]   * Listen & Join our email community: https://www.thefoundershustle.com [https://www.thefoundershustle.com]   * Connect with the host, Judy Swafford, on LinkedIn: https://www.linkedin.com/in/judyswafford [https://www.linkedin.com/in/judyswafford]   * Get on the podcast: https://tinyurl.com/3fwb7bny [https://tinyurl.com/3fwb7bny]

The Cash Flow Mistake That Kills Small Businesses | Cherise Lloyd

What do you do when your business is growing, your bills are stacking up, and cash gets tight? In this episode of The Founders Hustle, Judy sits down with Cherise Lloyd, author of The Shortfall Solution and founder of a financial content and consulting agency, to talk about one of the biggest challenges business owners face: cash flow shortfalls. Cherise brings a rare perspective to the conversation. With experience at the Federal Reserve during the financial crisis and later managing a $1.5 billion leveraged finance portfolio, she now helps small business owners understand the financial blind spots that can quietly put their businesses at risk. This episode is packed with practical advice for entrepreneurs who want to build wisely, stay financially prepared, and avoid the mistakes that can turn a temporary gap into a serious crisis. In this episode, you’ll learn: *  The biggest mistake business owners make when cash gets tight  *  How to recognize the warning signs of a shortfall early  *  Why “information avoidance” can hurt your business  *  Cherise’s 7-day, 20-day, and 13-week framework for recovery  *  What every founder should understand about cash, credit, and business survival  This is a must-watch for entrepreneurs, small business owners, and leaders who want to grow with more confidence and fewer financial surprises. Connect with Cherise: https://www.linkedin.com/in/cherise-lloyd-w-2ls/ [https://www.linkedin.com/in/cherise-lloyd-w-2ls/] Support the show [https://buymeacoffee.com/thefoundershustle] * Watch & Subscribe on YouTube: https://www.youtube.com/@TheFoundersHustle [https://www.youtube.com/@TheFoundersHustle]   * Connect with the host, Judy Swafford, on LinkedIn: https://www.linkedin.com/in/judyswafford [https://www.linkedin.com/in/judyswafford]   * Get on the podcast: https://tinyurl.com/3fwb7bny [https://tinyurl.com/3fwb7bny]

From Living Room Startup to 135 Employees: A Father Daughter Business Story (Visiting Angels)

What does it really take to start a business from scratch — with no prior experience, plenty of uncertainty, and a whole lot of heart? In this episode of The Founders Hustle, Judy sits down with Denny and Ellen of Visiting Angels Southwest Michigan, a father-daughter team who built their business from one employee in a living room into a thriving company with 3 offices and 135 employees. This conversation is full of honest lessons for anyone who wants to start a business, grow through the hard seasons, and learn from founders who have actually lived it. From cash flow pressure and burnout to imposter syndrome, leadership growth, and building a company people trust, this episode is a real look at what entrepreneurship requires behind the scenes. If you’re dreaming about starting something of your own, this episode will remind you that you do not need to have it all figured out to begin — but you do need resilience, humility, and a willingness to grow. In this episode, you’ll learn: - How they started their business with no prior industry experience - What helped them grow from 1 employee to 135 - The hard lessons they learned in the first year - How Ellen overcame imposter syndrome to become an owner - Why support systems, community, and adaptability matter in business Every business has a backstory — and this one is packed with practical wisdom and inspiration for founders at every stage. Connect with Visiting Angels: https://www.visitingangels.com/southwestmichigan/home Support the show [https://buymeacoffee.com/thefoundershustle] If you’d like to toss a one-time “thank you” or grab a GRIT Happens sticker, you can do that by clicking the "Support The Show" link above or visit: https://buymeacoffee.com/thefoundershustle * Watch & Subscribe on YouTube: https://www.youtube.com/@TheFoundersHustle   * Listen & Join our email community: https://www.thefoundershustle.com   * Connect with the host, Judy Swafford, on LinkedIn: https://www.linkedin.com/in/judyswafford   * Get on the podcast: https://tinyurl.com/3fwb7bny

From Corporate to Entrepreneur: How Mark Stern Built a Million Dollar Business

What does it really take to leave corporate America and build a business of your own? In this episode of The Founders Hustle, Judy sits down with Mark Stern, founder and CEO of Custom Box Agency, to talk about the mindset shifts, hard lessons, and personal growth that helped him go from corporate high performer to successful entrepreneur. Mark shares how he built his business during COVID, why he had to stop thinking like an employee and start thinking like a founder, and how niching down helped his company grow from zero to one million dollars in its first year through word of mouth. This conversation is packed with wisdom for aspiring entrepreneurs who want to start a business, scale with intention, and learn from someone who has faced the fear, uncertainty, and pivots that come with building something from scratch. In this episode, you’ll learn: -Why corporate success does not automatically translate to entrepreneurship -The mindset shift founders need to make to grow -How niching down can unlock business growth -Why mentorship matters more than most entrepreneurs realize -How trusting your gut can protect your business and your team If you’ve been thinking about starting a business, this episode is a powerful reminder that success starts when you stop trying to play by someone else’s rules. Connect with Mark Stern: https://www.linkedin.com/in/marustern/ Visit Custom Box Agency: https://customboxagency.com/ Connect with your host, Judy Swafford: https://www.linkedin.com/in/judyswafford visit https://thefoundershustle.com for more founder stories. Support the show [https://buymeacoffee.com/thefoundershustle] If you’d like to toss a one-time “thank you” or grab a GRIT Happens sticker, you can do that by clicking the "Support The Show" link above or visit: https://buymeacoffee.com/thefoundershustle * Watch & Subscribe on YouTube: https://www.youtube.com/@TheFoundersHustle   * Listen & Join our email community: https://www.thefoundershustle.com   * Connect with the host, Judy Swafford, on LinkedIn: https://www.linkedin.com/in/judyswafford   * Get on the podcast: https://tinyurl.com/3fwb7bny