An Update On My $1.2M/Year Portfolio Of Side Hustles

Published: September 5th, 2022
Michael Gardon
Founder, Rejoin Media
Rejoin Media
from Madison, WI, USA
started July 2019
market size
starting costs
gross margin
time to build
150 days
average product price
growth channels
Organic social media
business model
time investment
Full time
pros & cons
39 Pros & Cons
2 Tips
Discover what tools Michael recommends to grow your business!
Discover what books Michael recommends to grow your business!
Want more updates on Rejoin Media? Check out these stories:

Hello again! Remind us who you are and what business you started.

Hi, I am Michael Gardon, CEO of Rejoin Media, which owns and operates a portfolio of web-based businesses. I operate this side of the business on a private equity model, where I acquire businesses and invest working capital into them for growth. Rejoin also provides digital marketing services for a small number of select clients if and when I choose - for instance we were integral in setting up the first reviews-based content and marketing teams for when it was acquired in late 2019.

The main site I operate is, which helps people pursue more resilient careers by assisting people through the job search process, but also by breaking down preconceived notions of what a career is supposed to be. I spend most of my time on where I serve as editor and host of our acclaimed Careercloud Radio Podcast, which has been ranked best job search podcast by

The essence of ‘Rejoin’ is that many of our team members have worked together in the past. Our team is getting back, or ‘rejoining’ our roots and reconnecting to what is most important. As we have all pushed hard for success in many different ways, we have grown, matured, and added other elements to our lives besides work. When we came together around doing another company, we were very intentional about designing our business around our lives and making sure we took the long view of engineering resilient, life balance into our work.

Right now, growth has slowed a bit given the online advertising climate, but we are still working towards building Rejoin into a $15 million company we can run with 5-8 close contacts with a small team. We have also made some divestments which have decreased our top line revenue growth since the last year.

(original starter story)

Tell us about what you’ve been up to. Has the business been growing?

Rejoin is a great side hustle to a full-time business story, and I love sharing our story and approach with people who dream of breaking out of their 9-5 job. However, it's very multi-faceted because I always envisioned the business as a portfolio and a launchpad for doing many different types of products and services.

So let's go one by one!

Since I was last on Starter Story, we divested one of our portfolio businesses, This was done to free up some capital and invest in other portfolio companies, mainly has continued to grow traffic and traffic value. However, we’ve experienced a pullback recently. The content we do is aimed at helping career professionals progress from job search to resume help to helping small businesses hire.


The SEO game is hard because your business is at the mercy of Google, and there has been a big shift toward larger, higher DA sites for certain keywords, which hurts a smaller site like ours.

Being easy on yourself in your headspace.

So, diversification has always been the game for me - how do we diversify away from advertising and reliance solely on search traffic? My answer is to create other distribution channels. I launched a weekly newsletter called The Break where I built an audience of over 13,500 readers by talking about the concept of breaking work. Breaking work means consciously reinventing yourself, re-orienting your concept of work, and intentionally creating a better work-life. None of us need a job, we need a revenue source. Thinking about breaking work is a passionate topic of mine since my career has taken so many twists and turns (and probably will continue to long into old age!). I cover the changer’s mindset, how to break into a new job, start a side hustle, and take it to a full-time job.

The Careercloud Radio Podcast is another avenue where I talk about breaking work and interview leaders with amazing career pivot stories. All of our conversations and other videos are on our youtube channel as well. The key to all of this is a repurposing of content across channels.

The goal is to build a tighter community around career pivots and the tools necessary to pull them off.

Finally, I launched my first physical product called Quotebook, which is something I’ve never done before and is more of a passion project. My family built a habit of writing down all the very funny things we have said to each other in a quotable journal as a way of remembering the small things in our lives. We’ve recently been picked up on and will be in shortly, brought on our first retail stores, and so things are progressing nicely at a few thousand dollars per month in sales.

My day-to-day focus is really on leveraging my brand to communicate across all the things that I do in a cohesive narrative to build an audience. I believe the audience that my message resonates with the most is aspiring entrepreneurs and solopreneurs who want to take back sovereignty over their lives. So a lot of my content is focused on the time I get to spend with my family because of how I took control of my work-life.

What have been your biggest challenges in the last year?

The idea that this entire business is organic search driven is a very big challenge that I’ve been working to diversify, but building an audience from scratch is not that easy.

For one, it means that I have to take a more active role in being the “face” of the business everywhere. I’m an introvert and I’ve traditionally had operations roles behind the scenes where I could let other people get the publicity. But now it’s me having public conversations on my podcast, doing interviews on the news, creating more content on Linkedin or Twitter, etc. This isn’t natural for me so it’s a learning experience that I must be patient with.

I have to get better at selling as well. One great channel for Quotebook is small retailers and gift shops. It’s not natural for me to just walk into a store and pitch a product, even though I think our story is amazing. So I procrastinate on it. Thankfully, since we’ve gotten some online press, it made it a bit easier to walk into physical places and talk about the product.

This evolution is all necessary to diversify income away from a 100% organic traffic, and ad-driven revenue mix. I think building a direct audience is key to this shift.

What have been your biggest lessons learned in the last year?

Building an audience is hard. I’ve taken a couple of very good audience-building courses, but it easily feels like I could be on social media 20 hours a day building content, engaging, and promoting it. I definitely wish I started years ago.

However, on the flip side, I’ve learned that my message of an intentionally built life based on work-life harmony resonates loudly, so I just need to keep at it. There are millions of people dreaming about breaking out of their work to do something they love, and I can help them.

Also, Facebook ads don’t work to drive sales for small brands. I’m sure someone will disagree with me, but I hired two different “experts” and nothing. I believe if we were to ramp up spending we would see some lift, but not enough to make it worth while. On top of that, Facebook is just weird about displaying your content to people who actually like your page! It’s the strangest thing, but they just want you to spend ad dollars.

I sound salty, but I can only go off my experience.

What’s in the plans for the upcoming year, and the next 5 years?

For the next year, I am really focusing on building the retail sales channel for Quotebook. When we have that established I have plenty more product ideas where I think we could expand in this line of business, but we need the recurring sales.

I’m also focused on building my own course for Careercloud on how to start working for yourself incrementally.

The next 5 years is really all about diversified growth, so we will be pushing initiatives in several areas at the same time because we never truly know what will work. I will continue to invest and acquire businesses to build diversified wealth far into the future.

What’s the best thing you read in the last year?

I recently read The Lion Tracker’s Guide To Life by Boyd Varty and was blown away. Boyd is literally a lion tracker in Africa and he’s a professional life coach. The book is short, filled with some amazing stories, and is a metaphor for finding your path in life.

The entire story takes place as Varty and his two mentors track a lion in the wilderness which is unbelievable, but what resonated with me the most was the parallels between tracking to wayfinding in life. As a person who never felt like I had a particular path, I’ve been on a discovery journey all along.

A couple of good quotes:

“I don’t know where we are going, but I know exactly how to get there”

“Attention shapes the direction of the tracker’s life.”

Obsessed with perfection and doing it right, we want to go straight to the “lion.” We don’t realize the significance of the path of first tracks and how to be invested in discovery, rather than an outcome.

“If you can see your whole life’s path laid out then it’s not your life’s path.”

Advice for other entrepreneurs who might be struggling to grow their business?

There is no “playbook” that works for everyone. You can learn from those who have made mistakes before you, but you have to give yourself room to make your own mistakes and learn.

Giving yourself room means:

  • Being easy on yourself in your own headspace
  • Having patience
  • Not expecting perfection
  • Giving yourself enough runway to succeed (time and money)

Are you looking to hire for certain positions right now?

We are not hiring at this time, but we need to solve challenges with email marketing and audience building, so if you have expertise in these areas and want to build a relationship with me, please reach out via LinkedIn or Twitter!

Where can we go to learn more?

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

Want to start a career advice business? Learn more ➜