Make MORE money in LESS time, and get off the treadmill with Chuck Blakeman who
bootstrapped thirteen businesses in ten industries on four continents, and now advises others from his decades of “misses” and “makes”.
What if you built a business that that supported your desire to live your version of a significant life, without being a hostage to that business? You might never want to sell it. These podcasts are focused on helping us all find freedom IN our business, not from it.
We’ll also work through the principles, practices and tools every business owner uses to
become wealthy (money plus time), not just rich (money). Everything here has helped thousands of business owners become their own version of successful.
Tune in to hone your own version of moving from Survival, right through Success, to a business and life of Significance.
Episodes
Wednesday Aug 20, 2025
Wednesday Aug 20, 2025
As entrepreneurs, we’d never dream of blowing off an appointment with a client—so why do we so often blow off the appointments we set with ourselves?
In this episode, Chuck sits down with Mark Bellestri—a seasoned entrepreneur, 3to5 Club facilitator, and Crankset leader—to explore why honoring your own calendar may be the most important discipline in business ownership.
With a diverse career spanning real estate, insurance, banking, consulting, and business ownership, Mark has successfully grown companies in the locksmith, healthcare, and education sectors. Drawing from his wide-ranging experience, he shares why keeping appointments with yourself isn’t just a productivity hack—it’s a long-term strategy for freedom, balance, and abundance.
Together, Chuck and Mark unpack:
- The difference between signal vs. noise and why most of us get stuck in the noise.
- How “playing office” keeps us busy but not productive.
- The one thing you can do each week to create permanent momentum in your business.
- Why your strategic work needs a different place than your tactical work.
- How keeping appointments with yourself leads to less stress, more impact, and lasting freedom.
If you feel trapped by the tyranny of the urgent, this conversation is for you. Learn why your own calendar is the first place to start—and how committing to yourself can change your entire business trajectory.
3 days ago
3 days ago
Sometimes, the biggest obstacle to success isn’t failure—it’s waiting for the “perfect” plan. In this milestone 50th episode, Chuck welcomes back Jennifer Stapleton to explore why having a bad plan is often far better than no plan at all.
Jennifer shares her insights from the FasTrak program, including how creating a simple “bad plan for success” helped her break through analysis paralysis, build consistency, and drive real results. Together, they unpack practical ways to design a plan you can actually execute, how accountability tools (like giant paperclips!) can keep you on track, and why movement—not endless planning—creates clarity.
Jennifer Stapleton is the founding partner of Fire & Bliss, a communications and marketing firm serving philanthropies and nonprofits. With decades of experience as a strategist, advocate, and senior communications executive, Jennifer has helped organizations achieve major legislative wins, secure funding, and land coverage in top publications. Her unique mix of creativity and strategy continues to empower mission-driven businesses and nonprofits to thrive.
If you’ve ever found yourself overthinking, stuck in planning mode, or waiting for the perfect conditions to start, this episode will help you take action—because even a bad plan can lead to great outcomes.
🔗 Learn more about Jennifer’s work at fireandbliss.com
🔗 Connect with Jennifer on LinkedIn
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