
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.

Tuesday Sep 02, 2025
Tuesday Sep 02, 2025
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
Read the rest of this entry »

Tuesday Sep 16, 2025
Episode #51: How To Change Things Permanently
Tuesday Sep 16, 2025
Tuesday Sep 16, 2025
In this solo episode, Chuck Blakeman dives deep into the art and science of lasting personal change and why it’s fundamental for business owners who want to keep growing.
Chuck unpacks the four essential questions we all face around change:
- Can we change?
- Should we change?
- Will we change?
- And if so, how?
Along the way, he explores how our nervous system is wired for transformation, why knowledge alone won’t move the needle, and why true change comes from identity shifts, community, and attachment.
You’ll also hear practical insights about learning agility, reframing stress as growth, and the simple but profound truth: “If you want something to change, you have to change something.”
If you’ve ever struggled to make change stick or wondered how to grow without burning out, this episode will give you the mindset and tools to create permanent transformation in both life and business.

Tuesday Sep 23, 2025
Episode #52: Getting Rid the Whole Idea of Selling with Carey Lindeman
Tuesday Sep 23, 2025
Tuesday Sep 23, 2025
What if you could grow your business without “selling” at all? In this episode, Chuck sits down with Carey Lindeman to unpack the radical (and freeing) idea of Serve, Don’t Sell.
Carey shares how shifting from transactional sales to relational service has transformed her business and how principles like finding “lumberjacks,” hosting catalyst events, and asking the right questions can help you build trust, attract clients, and enjoy the process instead of dreading it.
Together, they explore practical strategies from the FasTrak framework that show why focusing on relationships, not transactions, is the path to sustainable growth.
If you’ve ever hated the idea of selling, this conversation will give you a fresh mindset and real-world steps to build your business in a way that feels natural, fulfilling, and effective.
🔗 Carey also joined Chuck earlier in Episode 28 – The Power of Moving From Rugged Individualism to Living in Business Community. Don’t miss that one for even more insights into building community in business!
Read the rest of this entry »

Tuesday Sep 30, 2025
Episode #53: Drip Systems
Tuesday Sep 30, 2025
Tuesday Sep 30, 2025
How do you stay top-of-mind with the people who matter most to your business without feeling like you’re “selling” to them?
In this solo episode, Chuck Blakeman dives into the power of a Drip System, a relationship-driven approach to marketing that keeps you consistently connected with potential clients and your key referral partners (what Chuck calls “Lumberjacks”).
Chuck lays out practical principles for creating a drip system you’ll actually enjoy doing for years, focusing on serving, not selling, while building the trust that fuels long-term success.
Whether you’re a solo entrepreneur or running a team, this episode will help you:
- Design consistent, energizing touchpoints with your audience
- Use recency and frequency the right way, without being pushy
- Pace yourself for long-term success instead of short-term sprints
- Build relationships that naturally turn into clients and referrals
🔗 New to the term “Lumberjacks”? Go back to Episode 27: Stop Networking – And Start Building a Network Instead! for the full backstory.
This is the roadmap to growing your business through authentic, relationship-based marketing, one steady drip at a time.

Tuesday Oct 14, 2025
Tuesday Oct 14, 2025
How can small business owners grow faster without chasing one client at a time? In this inspiring conversation, Chuck Blakeman sits down with Valerie Reid to unpack a powerful mindset shift — stop hunting trees, and start finding lumberjacks.
Valerie shares how the concept of “lumberjacks”; strategic partners who already have trusted relationships with your ideal clients, has transformed her approach to marketing, partnerships, and growth. Together, they explore what happens when you stop competing and start collaborating, and how to build win-win relationships that multiply opportunity for everyone involved.
You’ll learn:
✅ The difference between “hunting trees” and “finding lumberjacks”
✅ Why trust, not money, is your greatest business asset
✅ How collaboration with competitors can actually scale your business
✅ Practical ways to identify and nurture your own network of lumberjacks
If you’ve ever felt exhausted by chasing leads, this episode offers a smarter, more sustainable way to build your business through authentic relationships and mutual growth.
🔗 Want to go deeper into the concept of Lumberjacks?
Check out Episode 27 – Stop Networking and Start Building a Network Instead!
Read the rest of this entry »

4 days ago
4 days ago
Why does selling feel so uncomfortable—for both sides?
In this solo episode, Chuck Blakeman flips the script on traditional sales thinking and reveals why nobody wants to be sold, but everybody wants to buy.
Chuck unpacks four timeless principles that help you stop pushing products and start building relationships that naturally lead to business. You’ll learn how to move from transactional to relational selling and create conversations that make people say, “Oh, you get me.”
Here’s what you’ll discover in this episode:
✅ The four core principles that transform selling into serving
✅ Why consistency builds trust—and how to make it practical
✅ How to “meet people where they are,” not where you wish they were
✅ Why listening (not pitching) is your greatest business development tool
✅ How to create real connections that make people want to buy
If you’ve ever dreaded “selling,” this episode will help you rethink everything you know about business development—so you can stop selling and start serving.
💡 Listen now and learn how to flip the script for good.
