S2 E33 From School Teacher to Multi-Millionaire: The Business Moves That Changed Everything with Jess Glazer ✏️

Pollen: For Creative Entrepreneurs with Diana Davis

🚀 Sign up for Jess's FREE DBE Live 3-day event happening March 20th, 25th, + 27th! In this episode. How do you build a thriving business that actually supports the life you want—without working yourself into the ground?

In this conversation, I sit down with my mentor, Jess Glazer DeRose, to unpack how she went from being a school teacher to running a multi-million dollar coaching business—and why she ultimately shut down a $400K revenue stream to prioritize what really matters.

We talk about:

• The mindset shifts that allowed Jess to scale a business that works for her
• The best and worst investments she’s made (and what she learned from them)
• How to navigate the coaching industry’s messy landscape with integrity
• Why investing in yourself isn’t just about ROI—it’s about who you become in the process

Plus, we dive into DBE Live, an event that changed my business forever. If you’re ready to step into bigger opportunities, this is where you need to be. (Get all the details inside the episode!)

Ways to plug in

🏕️ Camp Clarity is now open for enrollment ALWAYS! But we cap the number of spots to keep an intimate group. Feeling ready to finally have the business of your dreams? Hop on the waitlist here.

🛝 Recess is the best place on the internet. Try it out for 3 months for just $165.

☎️ Follow Diana on Instagram here.

Key Episode Takeaways

✅ Your business should support your life—not the other way around. ✅ Scaling isn’t about doing more, it’s about doing what actually matters. ✅ Investing in yourself is the fastest way to grow (but not every investment is a good one). ✅ The coaching industry is full of noise—learn how to see through it. ✅ Sometimes, letting go of a revenue stream creates more abundance. ✅ You don’t have to have a big team to build a thriving business. ✅ Integrity is the key to long-term success in coaching. ✅ The right community can change everything.

Episode Chapters

00:00 - Why This Episode is a Must-Listen 02:56 - From School Teacher to Multi-Million Dollar Business Owner 06:05 - The Mindset Shifts That Changed Everything 08:53 - Scaling a Business That Actually Feels Good 12:02 - The Best and Worst Investments Jess Ever Made 14:58 - The Coaching Industry: What You Need to Know Before You Invest 17:51 - Why We Shut Down a $400K Revenue Stream 21:01 - Business, Motherhood, and Finding Balance 24:03 - The Real Reason People Stay Stuck in Their Business 28:34 - The Power of Community in Coaching 29:35 - What to Look for (and Avoid) in a Mentor 31:40 - Marketing, Manipulation, and Selling with Integrity 34:37 - Entrepreneurship in 2024: What’s Working Now 37:52 - You Don’t Have to Work Harder to Make More Money 48:14 - The Free Event That Can Change Your Business Forever