The Happy Hustle

Companies built: 0
Global podcast rank: Top 0.5%
VC raised in NYC: 7-figure
Continents on stage: 0

The origin

Surf town and a
cowboy town.

Cary grew up splitting time surfing the beaches of Sarasota, Florida and playing cowboy in the mountains of Red Lodge, Montana — where he first learned the art of a balanced lifestyle.

01 — 03

The operator

Three companies,
one hard lesson.

He has run three profitable, location-independent businesses and launched multiple start-ups. One NYC tech venture closed a 7-figure VC round and partnerships with Microsoft and IBM — and taught him what the grind really costs.

02 — 03

The stage

From boardrooms
to base camps.

From corporate conferences to multi-million-dollar retreats to US Navy, Army and Marine bases and school auditoriums across Guatemala, Spain, Brazil and beyond — he tailors Happy Hustlin' to every room he steps into.

03 — 03

— Bozeman, Montana

The long version

Ambition doesn’t require self-destruction.

Cary Jack is a lifestyle entrepreneur, author, and humanitarian. He grew up splitting time between surfing the beaches of Sarasota, Florida and playing cowboy in the mountains of Red Lodge, Montana — where he first learned the art of a balanced lifestyle.

As an entrepreneur, he has run three profitable, location-independent online businesses and launched multiple start-ups. One of his NYC tech companies secured a 7-figure VC round and partnerships with both Microsoft and IBM — and showed him, the hard way, what the grind really costs.

Today he hosts a top 0.5% globally-ranked podcast, runs exclusive entrepreneurial wilderness masterminds, and leads a monthly membership community — all built around one idea: you can harmonize ambition and well-being instead of trading one for the other.

His mission is simple — to educate, inspire, and entertain, while reminding you to enjoy the journey, not just the destination, as you Happy Hustle for a life of passion, purpose, and positive impact.

Podcast rank: Top 0.5%
Companies: 0
VC raised: 7-fig

Keynote highlights

Three talks, tailored to your room.

From corporate conferences to multi-million-dollar retreats to US Navy, Army and Marine bases and school auditoriums across Guatemala, Spain, Brazil and beyond — Cary custom-fits the message of Happy Hustlin’ to each audience so a lasting, impactful lesson on balance is left behind.

The Happy Hustle: 10 Alignments to avoid burnout & achieve blissful balance

When people are disengaged at work, revenue and productivity suffer. Cary's proprietary S.O.U.L. M.A.P.P.I.N.™ system puts the Happy back in the everyday Hustle.

The 10 Alignments of a Happy Hustler
Why balance equals happiness
How to give every area of life equal weight — one at a time

The unhappiness factor costing you and your company millions

Disengaged employees cost the US workplace billions every year, and two in three are checked out. Cary systematically lifts engagement and motivation with the Happy Hustle strategies.

Build a Happy Hustle culture of productivity
Install the 10 Alignments framework inside your company
Raise engagement, happiness and revenue together

Ninja sales secrets

Most people sell with sleazy tactics that leave prospects with a bad taste. The 7 Steps to Selling use pressure-free persuasion — the exact framework Cary used to sell millions of dollars over Zoom.