There are so many different types of ittybiz owners in the world, but so often only the biggest or flashiest ones get represented in the media we consume.

To counter this, I've been interviewing real IttyBiz customers and clients so that you can see the variety and diversity of solo businesses out there – and the different ways that people run their business and manage their work.

So without further ado, I'd love to introduce you to IttyBiz customer…

Gregory Anne Cox

Hey Greg! What do you & your ittybiz do?

I coach women over 50 to “age better”. Better as in without the average 5 prescription meds by the time they are 65. Better as in knowing what tests to get and not taking “this is what happens at your age” as the truth.

I write, I have a podcast, and I publish the kind of “outside the mainstream” health information you don’t find on the major sites – habits of longevity that I want people to know about.

How long have you been running this business?

You can find me at

(I also have a copywriting biz at

What was the hardest part of getting started / the early years?

I ran this business as Rebellious Wellness for 8 years until 3 years ago when I walked away from health coaching to write copy and help wellness coaches with their marketing.

I did this because the health coaching industry was filling up with “coach in a weekend” types and people who didn’t honor science over their MLM. (Even ancient science counts when it comes to things like Ayurveda, acupuncture, energy work, etc.)

Why did you start this business? What was the catalyst or “reason why”?

I came into the world wanting to help. As a kid I wanted to be a doctor. A chem teacher in high school told me I wasn’t good enough with science to be a doctor, that I was better with language. So I pursued psychology and writing.

When I was 18, my mother was diagnosed with pancreatic cancer, and I read every book on natural healing I could, thinking I could make a difference. I couldn’t – but I never stopped wanting to help.

I became a chef and eventually ended up cooking healthy food, and I was hired by a well known heart surgeon to create a menu for the first heart healthy fast food restaurant chain.

During that time he allowed me to be in the operating room with him while he performed an open heart surgery. He told me that if we could change people’s habits, 60% of those having the surgery would not need it. He showed me the damage the woman’s lifestyle had on the heart and it changed me forever.

Once I left cooking I got certified as a life coach and it led to health coaching. Too many women (as well as kids and men) are suffering with symptoms of diseases that are caused by Big Food, Big Pharma, Big Ag, and misinformation. It breaks my heart and I want to do my part to change this.

What was the hardest part of getting started / the early years?

I started an online gift business before the coaching biz. And since I’d already had a personal chef and catering business, I thought I knew what I was doing.

I made all the classic mistakes like paying for a logo, stickers, buying a ton of products so I’d have them on hand for the rush of orders. But I had no idea how to market the business besides calling people and letting them know.

I paid for a website, did projections, wrote a marketing plan, but I lacked the basic skills needed to “make it” and ran through a bunch of money. (Although everyone got lots of great organic self care products for Christmas that year!)

When I started my coaching biz I’d learned enough to know that I had to get experience coaching that paid me before hanging out my shingle so I did. But I still had a hard time marketing. I hated selling, didn’t understand the higher level concept of giving people something of value that they wanted so I limped along.

So I started writing an ezine weekly and started showing up at networking events. I usually had to drive 2 hours to NYC because I lived in a resort town and there wasn’t much business networking outside of the hospitality industry groups. And I built a list.

And, I had so much passion for it that I stuck it out. I wish I’d had a mentor or someone with business skills who could have guided me. Also wish I’d had blinders because I took a ton of courses and hired coaches for things I wasn’t ready for. Nothing wrong with what I paid for – just that I wasn’t at a level where it made sense to implement.

What’s easier for you now than it was in the beginning of your business?

Selling! And speaking as a lead gen activity and soul-satisfying way to get the word out (at least before Covid!).

Years into the business I still wasn’t great at selling but I managed. One day I decided to apply for a sales position on a team that does sales for the personal development gurus. I told them my track record wasn’t great but they said they’d train me. They were great trainers and there’s nothing like doing 20-30 one on one calls a week and or chat sales during a big campaign – and know that I had to make a certain % of sales – to get me to improve.

How many hours a week do you work on average?

20 during the summer, 25 – 30 the rest of the year.

How much time do you spend per week on social media?

I’m lousy at social media but working on improving, so right now I’d say I spend an hour or 2. I’ve spent more of my time learning IG and Clubhouse lately.

Do you answer your own email, or does someone else do it?

I answer some of my own email because at this moment (Since RWO50 is pretty new) I don’t get many generic ones. I answer Qs about coaching for RWO and request forms that come in looking for a bid for my other business, Be More Marketable.

The things I answer are because I’m the one who’s going to do the work and I want to be sure I can help the person and that they are a fit energetically.

My VA answers Qs about podcast interviews and handles correspondence with guests.

How frequently do you produce content?

About once a month during the summer.

How frequently do you email your list?

1 – 2 times per month now, and that will go back up to 4 – 6  after Labor Day.

Do you do everything yourself, or do you hire others to manage parts of your business?

I have had the same VA for 11 years! She handles all of my back end tech stuff and some design work. I hire out editing my podcast, graphic design, and had hoped to hire someone to help with social media but the company I tried for one month wasn’t a fit. I’ll try again.

What’s the best purchase / investment you’ve ever made for your business?

The ongoing best investment has always been good coaching/mentoring where I know I could up my game. Also having a VA (long before I could really afford one) has been key to me getting out there.

What’s your favorite product in the Karma Store?

I’m new to the Karma Store but damn, there’s a shit ton of great tools and resources in there (like The 1-Hour Content Plan, which I recently bought and liked!).

The UX is awesome and the graphics make me want to peek inside. (Maybe from my chef days but I still believe people eat with their eyes first so I appreciate and have always strived, to put things out there that are well designed.)

I hope to eventually get through all of the products in the Karma Store because the couple of things I’ve purchased have been high value already – and not a recycled version of what everyone else is teaching!

More customer profiles are coming – maybe one will be yours?

Kris FaraldoIf you're an IttyBiz customer and would like to be featured in an upcoming customer profile, get in touch!

And if you're not a customer yet, consider Gregory’s favorite product, The 1-Hour Content Plan – or any of the pay-what-you-want products in the Karma Store.

100% of store profits go to help ittybiz owners around the world through Kiva, in over 60 countries so far!

Take care!

Kris Faraldo

Unlock the IttyBiz Freebie Vault – 15 premium resources you can use to instantly get your ittybiz growing!

Unlock the IttyBiz Freebie Vault!