How Experiencing Burnout Led Me To Start One Of The Most Popular Podcasts In The World

Published: October 14th, 2022
Cary Jack - The H...
from Bozeman, MT, USA
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Hello! Who are you and what business did you start?

My name is Cary Jack and I’m a lifestyle entrepreneur, founder & author of The Happy Hustle, top .5% globally ranked podcast host, international keynote speaker, professional actor/model, biohacker, eco-outdoorsman, and humanitarian striving to make a positive impact on this planet.

As founder of The Happy Hustle, my mission is to help fellow purpose-driven entrepreneurs avoid burnout and achieve blissful balance in their personal and professional life while putting the Happy in their everyday Hustle!


What's your backstory and how did you come up with the idea?

You see… I WAS WORKING 100+ HOUR WEEKS, getting roughly 5 hours of sleep, and grindin’ my face off -- all for profit and success. My brother and I were sharing a queen bed in a shithole apartment in Queens, New York, hustlin’ every day for our innovative tech startup. We built an algorithm on how to quantify feedback and were soliciting seed funding to get it mainstream.

But after my brother and I landed the 7-figure VC funding deal and major partnerships with Microsoft and IBM, I felt completely unfulfilled.

So, after many tears and a gut-wrenching conversation, we made a massive pivot. We said no to the funding deal, scrapped a year and a half of hard work, and folded the company. I then moved to Bangkok, Thailand for 10 months. It was there where I figured out a better way to work and live in alignment. A way to find happiness within the hustle. A way to not just make money but an impact. And that is how The Happy Hustle™ was born.

Go a mile deep and an inch wide at first, solving a niche problem. Do it for free or break even initially, get testimonials, build trust and credibility, then increase prices, iterate, and evolve.

After I experienced entrepreneurial burnout, I knew there had to be a better way. So I made it my mission to help other entrepreneurs avoid burnout and achieve blissful balance both personally and professionally. I truly believe BALANCE = Happiness and the Happy Hustle was created to help busy entrepreneurs and professionals solve the infamous work/life balance problem.

I created the proprietary S.O.U.L.M.A.P.P.I.N.™ system which is made up of 10 Alignments and how to measure yourself in each:

  1. Selfless service
  2. Optimized health
  3. Unplug digitally
  4. Loving relationships
  5. Mindful spirituality
  6. Abundance financially
  7. Personal development
  8. Passionate hobbies
  9. Impactful work
  10. Nature connection

This system represents the replicable journey that just about anyone (but especially entrepreneurs) who struggles with imbalance, disengagement, and unhappiness can emulate to transform their reality into a blissfully balanced life they love.

Take us through the process of designing, prototyping, and manufacturing your first product.

The Happy Hustle is an online business with multiple revenue streams. We have free content, paid sponsorship/affiliate deals, The Happy Hustle Podcast, The Happy Hustle Book, The Journey Online Course, The Blissful Balancer (whiteboard fridge magnet) The Happy Hustle Club Membership Community, and The Montana Mastermind Epic Camping Adventure.

We initially started with an online course, then created a mastermind, then wrote a book, and the rest is history! The name of the game is continuing to create unique ways to serve our tribe.

One of the most important parts, when you’re creating a business, is understanding your value ladder and how you ascend and nurture customers through your pipeline. This has been a work in progress for the past 3 years, but currently, the Happy Hustle offers multiple ways to help mission-driven entrepreneurs achieve that blissful balance.



Describe the process of launching the business.

We started initially with the launch of the Happy Hustle Podcast back in Nov 2019. Our first guest was my friend and the legendary lifestyle entrepreneur, John Lee Dumas of Entrepreneurs of Fire. We built a friendship from working together in my former biohacking company and helped support one another as friends ever since.

Since then, we have been growing the podcast week over week, and are currently ranked .5% globally based on downloads (roughly 50k + downloads/views per episode at the time of this writing).

In my opinion, the biggest thing with a podcast is consistency. We have consistently put out 2 episodes a week ever since our inception. One interview episode on Tuesdays and one solo episode on Fridays. We send out promo assets to every guest who then in turn helps promote our show. We then send out emails and repurpose content across the various social media platforms to promote the podcast.

Our Youtube has also been growing rapidly, now approaching 100k+ subscribers and garnishing over 2 million views. This has also been a great way to grow the podcast (and bring in revenue) while also driving traffic back to our products and services.

Youtube tip: put your CTA link not only inside your video but also add it to the top of the show notes so viewers can easily click if interested.

In addition to the podcast, we created an e-book, then an online video course, then a digital mastermind, and finally our staple book, The Happy Hustle: 10 Alignments to Avoid Burnout & Achieve Blissful Balance. We financed the business by selling various consulting and coaching packages initially.

Now we don’t trade time for money but rather focus on creating D.A.R.E.S. like my friends at Brand Builders Group say, which are Digital, Automated, Recurring, Evergreen, and Scalable. The company is debt free and positive in cash flow each month.

Since launch, what has worked to attract and retain customers?

The best thing we’ve done in the business to retain customers and create true transformation is our Montana Mastermind Epic Camping Adventures. These are specifically for high-performing entrepreneurs making over 6 figures annually minimum (most 7,8, & 9) who want to digitally detox, tap into their primal nature, enjoy the great outdoors, and want to mix business with pleasure in the beautiful backcountry Montana wilderness with other rockstars like-minded Happy Hustlin’ entrepreneurs.

These trips have been a smashing success and have led to repeat clients, tons of referrals, and now more demand than supply. You can apply here if you’re feeling froggy!

The Happy Hustle Club has also proven to be an amazing way to consistently serve our tribe of entrepreneurs in a bi-weekly online mastermind. We bring in Guest Gurus who train on specific topics, have gamified cash accountability system to help keep us accountable for the things we say we're going to do, and also have a new Selfless Service cause brought to light each month in which we donate time, money, and expertise to helping.

The lesson here is that people are craving connection more than ever, especially after the pandemic and COVID. Now is a great time to bring people together both online and offline!

How are you doing today and what does the future look like?

Currently, the Happy Hustle is made up of an amazing team of 1 executive virtual assistant, 1 video/podcast editor, 1 website developer, 1 personal assistant, and multiple outsourced talent and freelancers.

My days typically consist of Zoom meetings, podcast recordings, writing, content creation, keynote speaking, and facilitating events. I honestly don't work that hard, generally averaging around 20 hours per week. But when I am working, I'm focused on flow. The future looks like more of the same but also starting a non-profit and working more in my other business with my brother and company CEO Grant. The company is focused on fighting plastic pollution, combating global warming, and creating earth-saving eco-solutions.

Through starting the business, have you learned anything particularly helpful or advantageous?

Learn how to sell with integrity. The art of pressure-free persuasion is imperative.

Also, understand that business is all about solving people’s problems at a profit.

Get crystal clear on what problem you solve, who you solve it for, and your uniqueness around it. Create systems and build a team to support you. Connect with like-minded fellow entrepreneurs and foster mutually beneficial relationships. Those are a couple.

What platform/tools do you use for your business?

What have been the most influential books, podcasts, or other resources?

Advice for other entrepreneurs who want to get started or are just starting out?

Go a mile deep and an inch wide at first, solving a niche problem. Do it for free or break even initially, get testimonials, build trust and credibility, then increase prices, iterate, and evolve.

Also, don’t just focus on your business but your character. Be a great person. Be a great partner/lover, father/mother, son/daughter, and friend.

Take care of your health, and don’t slack in this department as your business requires energy, and to produce energy to optimally execute your mission, you need to be in optimal health!

Are you looking to hire for certain positions right now?

Looking for a COO currently. Someone to run the business and be my #2 right hand so I can stay more in my zone of genius. Send an email with your resume and a less than 60-second video as to why you want to work with us to [email protected].

Where can we go to learn more?

Thanks so much for your time! Here’s to Happy Hustlin’ your dream reality full of passion, purpose, and positive impact!

Peace & love y’all!

If you have any questions or comments, drop a line below!