
The Elite Entrepreneurs Podcast
If you’re one of the 3-5% of entrepreneurs that’s grown their business to seven figures in revenue, congratulations! You are an ELITE entrepreneur. Few people can say they’ve accomplished what you have. I’m sure that success hasn’t stopped you from wondering: What’s the next step?
Getting from six to seven figures is a commendable and extremely difficult feat, but it’s not smooth sailing after you clear the $1 million mark. If you’re like a lot of entrepreneurs, you’re probably encountering a host of new problems you’ve never fought through before. Leadership changes, vision changes, and you might find yourself wearing ten hats in a given day. That climb up to $10 million seems insurmountable, right?
Welcome Brett Gilliland, your host of the Elite Entrepreneurs podcast. Brett Gilliland is Founder and CEO of Elite Entrepreneurs, a company that specializes in giving $1M+ business owners the knowledge, processes and tools to grow to $10M and beyond. Brett is an expert in organization development, leadership and strategy and spent 10 years helping Infusionsoft grow from $7M in revenue to over $100M. Brett was involved in the foundational work of Purpose, Values and Mission at Infusionsoft and facilitated the strategic planning process for many years.
Latest episodes

Oct 16, 2024 • 32min
Empowering Your Innovative Business Strategies with Rania Ajami
Welcome to this week’s episode of Seven Figure Journey, featuring Rania Ajami, the visionary founder of Metropolis. Discover how she turned the closure of a beloved children's entertainment venue into a thriving virtual ecosystem.

Oct 10, 2024 • 30min
Lynx Hawthorne's Legacy in Craft Brewing
Welcome to this week’s episode of the Seven Figure Journey podcast, featuring Lynx Hawthorne, the visionary co-founder of Best Craft and Grimm Brothers. Discover how Lynx turned struggling craft beer brands into an award-winning success story.

Oct 10, 2024 • 38min
Rachel Foy’s Entrepreneurial Journey: Overcoming Challenges and Building Hillman Homes
Welcome to this week’s episode of Seven Figure Journey, featuring Rachel Foy, the visionary founder of Hillman Homes. Discover how she turned the challenge of navigating Boston’s tough real estate market into a success story.In this episode, we dive deep into Rachel’s strategic approach to overcoming team motivation hurdles in a remote work environment, highlighting innovative solutions and key business strategies.Rachel shares personal anecdotes, including how her difficult experience as a first-time homebuyer shaped her entrepreneurial journey and her perspective on maintaining a boutique firm culture.Enjoyed the episode? Like, comment, and subscribe to our channel for more inspiring content. Connect with Rachel Foy via hillmanfoy.com and learn more about her journey.

Oct 9, 2024 • 36min
Doug Meadows' Entrepreneurial Journey: From Family Legacy to Innovation at David Douglas Diamonds
Welcome to this week’s episode of The Seven Figure Journey, featuring Doug Meadows, the visionary founder of David Douglas Diamonds. Discover how he turned a family legacy and business challenges into a success story.In this episode, we dive deep into Doug’s strategic approach to overcoming setbacks, including how he recovered from bankruptcy and refined his business processes to thrive in the jewelry industry. He highlights innovative solutions such as leveraging mentorship and hiring a virtual assistant to scale his business effectively.Doug shares personal anecdotes, including how a fire nearly destroyed his family’s business and how a mentorship with a Chick-fil-A business coach shaped his approach to entrepreneurship.Enjoyed the episode? Like, comment, and subscribe to our channel for more inspiring content. Connect with Doug Meadows via DavidDouglas.com and learn more about his journey.

Oct 8, 2024 • 39min
How to Delegate Effectively with Wes Hackett
Welcome to this week’s episode of Seven Figure Journey, featuring Wes Hackett, the visionary founder of Cloud5 Accounting. Discover how he turned multiple business failures into a success story.In this episode, we dive deep into Wes Hackett’s strategic approach to overcoming entrepreneurial setbacks, highlighting innovative solutions and key business strategies that helped him scale his company.Wes shares personal anecdotes, including how a failed retail venture shaped his entrepreneurial journey and his perspective on financial clarity for small businesses.Enjoyed the episode? Like, comment, and subscribe to our channel for more inspiring content. Connect with Wes Hackett via LinkedIn and learn more about his journey.

Oct 8, 2024 • 40min
How to Keep Productivity High During Employee Absences with Kristen Graham Brown
Welcome to this week’s episode of Seven Figure Journey, featuring Kristen Graham Brown, the visionary founder of Hoop Design Company. In this episode, Kristen shares how she turned the challenge of managing maternity leave in a small team into a success story by implementing innovative solutions and business strategies. We also explore her journey, including a pivotal moment when she transitioned from retail to branding, and how that decision shaped her perspective on building a culture-driven business. If you enjoyed the episode, don’t forget to like, comment, and subscribe for more inspiring content. Connect with Kristen via hootdesigncompany.com to learn more about her journey.4o

Oct 8, 2024 • 38min
How to Pivot Your Business in a Crisis and Still Thrive: Lessons from Rebel Cheese's Founder
Welcome to this week’s episode of The Seven Figure Journey, featuring Kirsten Maitland, the visionary founder of Rebel Cheese. Discover how she turned the unexpected challenge of scaling her business during COVID-19 into a success story.In this episode, we dive deep into Kirsten’s strategic approach to overcoming operational bottlenecks and explosive e-commerce growth, highlighting innovative solutions and key business strategies.Kirsten shares personal anecdotes, including how her appearance on Shark Tank shaped her entrepreneurial journey and her perspective on pivoting in the face of uncertainty.Enjoyed the episode? Like, comment, and subscribe to our channel for more inspiring content. Connect with Kirsten via kirsten@rebelcheese.com and learn more about her journey.

Oct 8, 2024 • 34min
Bryan Driscoll’s Proven Strategy for Real Estate and Lead Generation Success
Welcome to this week’s episode of Seven Figure Journey, featuring Bryan Driscoll, the visionary co-founder of Motivated Leads, LLC. Discover how Bryan turned early failures in real estate into a thriving lead-generation business for investors.In this episode, we dive deep into Bryan’s strategic approach to overcoming business challenges, highlighting his innovative solutions and key strategies for success.Bryan shares personal anecdotes, including how his experience with digital marketing and real estate shaped his entrepreneurial journey and his unique perspective on scaling a business through bootstrapping.Enjoyed the episode? Follow, rate, and subscribe to our podcast for more inspiring content. Connect with Bryan via LinkedIn or visit Motivated Leads to learn more about his journey.

Oct 7, 2024 • 45min
Marc Sampogna's Intersection of Creativity and Entrepreneurship
Welcome to this week’s episode of the Seven Figure Journey Podcast, featuring Marc Sampogna, the visionary founder of Canopy Brand Group. Discover how he turned the challenges of launching a business during a recession into a remarkable success story.

Oct 7, 2024 • 39min
Ozzy and Zachary: From Napkin Ideas to a Thriving Agency
Welcome to this week’s episode of the Seven Figure Journey podcast, featuring Ozzy Garner and Zachary Conover, the visionary founders of Advertis. Discover how they turned the complexity of marketing agency partnerships into a success story.
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