How I Built A $100K/Month Portfolio Of Web-Based Businesses

Published: July 19th, 2021
Michael Gardon
Founder, Rejoin Media
Rejoin Media
from Madison, WI, USA
started July 2019
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Hello! Who are you and what business did you start?

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 that I choose.

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.

Two of my sites are in the education and career spaces. helps people pursue more resilient careers by helping 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 helps young people navigate their choices to level up their skills and excel on standardized tests.

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 really 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.

So, we are working towards building Rejoin into a $15 million company we can run with 5-8 close contacts - giving us all the flexibility and life we want. Right now, we are running about $100,000 per month in revenue and growing at about 20% per month.


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

I remember my dad asking me what I was going to do after college. I had no idea, so I said, “I’m not sure, but I know I’m going to be doing lots of different things!”

Not having a “career track” was always something I looked at as a problem. I felt like I never really could fit my experience on a resume - I tried resume writing services, but a resume could never capture what I was about or where I was going.

Fast forward a few years and I started my career as a banker, then a derivatives trader in Chicago started a company where we sent our technology up into space on satellites, then learned SEO and got into content marketing where I helped build a major venture-backed online review site -

I still didn’t know what I was doing, but what I said to my dad turned out to be right - I was doing lots of different things. The rat race of building a company using venture capital had got to me, plus I was starting to build a family.

I knew I absolutely did not want to take venture money again. Been there. Done that. Good result, but I learned that control means more to me than growing fast.

I needed a break so I took a corporate consulting job trying to help a large Fortune 300 insurance company build new businesses. The plan was either I would exit by running one of the startups we spun out, or I would start something else when the time was right. My team built and launched the first non-insurance business in the company’s 100+ year history. That company, Moonrise, is a short-term staffing company aimed at helping financially vulnerable people make ends meet.

After a year and a half, and the birth of my 3rd child, the corporate bureaucracy was getting to me, and I started plotting my exit for what would become Rejoin.

Describe the process of launching the business.

I knew I wanted to get back into content marketing - it’s sort of the perfect lifestyle business, but I wasn’t sure where to start.

I launched this business by the process of elimination. Since I had started several companies, I had some experience in what works and what doesn’t - for me. So, I designed the business around what would work well for my life - getting extremely intentional about what I would not compromise on.

What I Didn’t Want

  • I knew I absolutely did not want to take venture money again. Been there. Done that. Good result, but I learned that control means more to me than growing fast.
  • I did not want to be in the client service business long-term.
  • Did not want the headcount to be too big, as that creates management headaches.
  • I didn’t want to travel much.

What I Had

  • Capital to acquire sites
  • SEO and content marketing operations expertise and credibility
  • Patience

Charting A Path With Patience

I used some capital to acquire a couple of sites and started working on them as a side hustle while still corporate consulting. To break the corporate shackles, AND if I wanted to stay away from raising money, I would need clients to bring in money that I could apply towards the growth of my sites. However, becoming an agency was off the table. There are some great agencies out there, but that is not a model that fits well within my life.

So, I needed to find one big client, where I could fund and build a team that I could also use to grow my business. I networked and took pitch meetings off and on for the better part of a year trying to find the right fit. Just before Christmas, 2018 I signed a deal that allowed me to leave my job and invest in my portfolio businesses.

Fast forward to May 2021, my portfolio businesses are growing rapidly enough that I no longer need client revenue for working capital. We have parted ways with our client, and are looking forward to continued growth.

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

Because of my background, almost all of our revenue is affiliate marketing and advertising. This game has gotten very competitive, but the formula is still the same: great content on the right topics plus high-quality links equals traffic and conversions.

Traditional link outreach is very tough because everyone understands it now, so I have done a lot more PR and media intending to drive links to our site. For PR, we have created our own studies around competitive careers and remote work, which was a huge topic during the pandemic.

Here’s me on ABC news in Tampa, FL

And here’s a screenshot of our link growth on You can see it had really stagnated for several years before we started working

Going forward, I’m investing heavily in other marketing channels. We have done some Google and social ads, but have not found much success.

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

Today, our core portfolio businesses are thriving as we have successfully applied our organic traffic strategies and have the right advertising partnerships in place. This necessary step will allow us to invest cash into the next phase of Rejoin, which will be a very creative one.

True to form when I told my dad all those years ago that I would be doing many different things - I’m now focusing on diversifying my business away from affiliate marketing and looking to build more products and marketing channels.

We are developing career courses, books and I am looking to grow my Careercloud Radio podcast, which I have never done before.

I have also launched Rejoin Capital where I make cash-only investments in new businesses, but do not take on an operating role.

CareerCloud’s traffic value

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

Psychology is such a big part of being able to start, grow and stick with a new business. And the best way to succeed is simply through adherence. The best investments, plans, diets, and habits are all the ones that are easiest to stick with.

Resiliency is brilliancy. Realize that things change fast. Build multiple income streams into your life. Build multiple areas where you derive satisfaction. Build your network even when you don’t think you need to. Things change, and a great plan always has backup.

You can engineer more adherence to your plans by being extremely honest with yourself about what you can handle. The way I do this is by asking “What must be true (for X, Y, or Z) to happen?”

The Rejoin story might not be a sexy one, but I’m proud that, every step of the way, I was in line with what I needed to move to the next phase, and that helped me just keep putting one foot in front of the other slowly and patiently.

What platform/tools do you use for your business?

We are a completely remote team, so we use collaboration tools like Slack, Google docs, Asana and Zoom. Our sites are all on WordPress or Squarespace, which are handy.

Of all our collaboration tools, I think Loom is the best! This tool allows me to create instructions and explain details then create a library for training. The best feature (in my opinion) is that it cuts down on meetings!

On the personal front, I use Evernote exclusively for dumping my brain into it. I journal build-out business ideas and save reading materials for later.

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

I used to be a voracious reader before I had kids. Now, I primarily use audible and listen to podcasts as my “free” time is taken up with coaching kids, going to their events, or just messing around in the yard.

I would say the book that has had the most impact on me is The Art of Learning by Josh Waizken. In particular, there is a chapter entitled “Investment In Loss.” This chapter is about the concept that sometimes you need to take one step back to make a giant leap forward. I read this chapter, reframed a struggle that I was having as an investment in my future, and quit my trading career next week. My life would not be the same if I hadn’t permitted myself to go “backward” to move forward.

The investment in loss concept has wide-ranging implications for how we look at risk and reframe it from something scary to something that can bring growth.

The next book is Principles by Ray Dalio. I’ve always followed Ray, and I read this when it was just a pdf many years before he eventually turned it into a book. It’s timeless.

Finally, I’m a huge fan of the Farnam Street Blog and Shane’s insights on decision making and mental models.

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

If you’re young, there are a couple of things to realize that will accelerate your journey:

  1. There will never be a better time to take risks. You should take as much risk as you can - your youth and few commitments will allow you to bounce back more quickly.
  2. Just start. You’ll learn more by doing than you will by reading, and you’ll do it faster.
  3. Resiliency is brilliancy. Realize that things change fast. Build multiple income streams into your life. Build multiple areas where you derive satisfaction. Build your network even when you don’t think you need to. Things change, and a great plan always has backup.
  4. Get a coach or a mentor. Learn from their mistakes and use their wisdom as a guide.

Are you looking to hire for certain positions right now?

Yes! We’re always looking for great writers, particularly in the career space. In addition, I would love to work with experts in podcast growth and eCommerce to help us launch a new book product!

Where can we go to learn more?

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