Ever feel like you’re hustling nonstop but still wondering, “Why isn’t this moving faster?” Or maybe you've hit that invisible wall where the business is growing… yet somehow you’re not growing with it?

In this episode of the Happy Hustle Podcast, I’m jammin’ with David Guttman, a serial entrepreneur, executive leader, and business strategist with over 35 years of building, scaling, and exiting multiple eight and nine-figure companies. This dude is a three-time Inc. 500 entrepreneur, has an undergrad in Computer Science from Brown University, an MBA from Wharton, and has led teams of hundreds while growing companies from near-bankruptcy to blockbuster exits. He’s lived the startup grind, the CEO pressure-cooker, the investor negotiations, the due diligence marathons — all of it.

But what makes David so special isn’t the titles. He’s lived real adversity, made real money, lost real sleep, and came out with clarity, humility, and wisdom worth borrowing.

In this episode, we dive into everything from raising capital to avoiding the trap of traditional education… from avoiding burnout to leveraging AI… from building healthier relationships to firing your worst customers. The breadth of knowledge he brings is crazy, but the heart behind it is even better.

David breaks down the single biggest mistake entrepreneurs make when trying to raise money or prepare for an exit, failing to budget and forecast. He explains why “dollar cost average into Bitcoin” may be smarter than chasing shiny objects, why AI will replace those who don’t use it, and why authenticity beats any degree, credential, or fancy LinkedIn headline.

Here are a few key takeaways from the episode:

Your business is blind without a budget. If you’re not forecasting, tracking, and adjusting, you’re not running a company — you’re gambling. A real financial model acts like a crystal ball and boosts your valuation instantly.
Mentorship beats an MBA every time. David explains why working for a powerhouse leader (even for free) will fast-track your growth more than any traditional education ever could.
Fire your worst customers. They drain 80% of your energy and slow your growth. Raise your price until they leave — or until they become worth it.
AI is the new calculator — ignore it and get left behind. Spend a couple hours a week learning and applying it, and you’ll leapfrog the competition. Avoid it, and you’ll get replaced.
Authenticity wins the long game. The world is noisy. People trust people — not institutions. Build a personal brand rooted in truth, service, and value.

David also breaks down the real reason businesses stall during acquisitions, how to build the right board of advisors, why fast “no’s” are better than slow “maybe’s,” and why success feels empty unless your relationships, health, and integrity stay intact along the way.

This episode is for every entrepreneur who wants to scale without losing themselves. For every hustler who wants to work smarter, earn more, and still be present for the people who matter. And for every dreamer who knows there’s more in the tank, more impact, more purpose, more joy.

If you’re ready to level up how you build, how you lead, and how you live, then you’ve gotta tune into this full conversation. David drops tactical wisdom, real-world stories, and mindset shifts you’ll want to revisit again and again.

What does Happy Hustlin mean to you?
David says it's like, if you can enjoy the journey, then what's it all for? And it's the same thing. you know, most of the people, it's why I found the conversation with you when we first, you know, interacted, refreshing.

Connect with David
https://www.facebook.com/drguttman
https://www.instagram.com/daverguttman/
https://x.com/daveguttman_
https://www.youtube.com/@OfficialDavidGuttman
https://www.tiktok.com/@davidguttman
https://www.linkedin.com/in/drguttman/

Find David on this website:
www.guttmanmedia.com

Connect with Cary!
https://www.instagram.com/caryjack/
https://www.facebook.com/SirCaryJack
https://www.linkedin.com/in/cary-jack-kendzior/
https://twitter.com/thehappyhustle
https://www.youtube.com/channel/UCFDNsD59tLxv2JfEuSsNMOQ/featured

Get a free copy of his new book, The Happy Hustle, 10 Alignments to Avoid Burnout & Achieve Blissful Balance https://www.thehappyhustle.com/book
Sign up for The Journey: 10 Days To Become a Happy Hustler Online Coursehttps://thehappyhustle.com/thejourney/
Apply to the Montana Mastermind Epic Camping Adventurehttps://thehappyhustle.com/mastermind/

“It’s time to Happy Hustle, a blissfully balanced life you love, full of passion, purpose, and positive impact!”

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