ike Gardon is no stranger to intense work hours.

He started his career as a prop futures trader, did content marketing for website conglomerate Soda.com, and more recently worked as a consultant, including to a Fortune 500 company.

The latter job was a means to an end: a better work/life balance built on acquiring small websites through his holding company Rejoin Media.

Mike started using strategic acquisitions to build a runway that would help him escape the corporate world and spend more time with his young children.

His previous experiences guided the types of businesses he wanted to acquire. Based on his SEO and content marketing work, he settled on websites that he could monetize leveraging these skills. And as a former trader, he understood the importance of a diverse portfolio. He wanted multiple websites that differed in content and business models.

“I'm a big believer in trying to do two or three things at the same time, because the reality is, you just don't know what's going to take off and what's not.”

Around 2016, Mike and his business partner bought a career website called CareerCloud for a price in the mid-five-figures range. He knew he’d have to redo all the content to optimize it for SEO, and that he’d have to change the site’s business model. But he could see that the basic framework had potential.

Mike started working on CareerCloud in earnest in 2019. Through affiliate marketing, he turned the site into a solid income generator. It now produces most of Rejoin Media’s $100,000 monthly revenue. In addition to CareerCloud, Rejoin Media owns websites about school exam prep, fitness, and solar power.

On this episode of Acquiring Minds, Mike explains how he made plans to transition from contractor to boss, how to decide what you want to acquire, and why interviews are so valuable that he’s willing to overcome his introverted tendencies to do them whenever he can.

Check out:

✳️ About Mike Gardon

✳️ Top takeaways from the episode

✳️ Episode highlights with timestamps

✳️ Links & mentions

Acquisition Entrepreneur: Mike Gardon

💵 What he acquired: Mike previously worked as a prop futures trader, and later as a content marketing manager for Soda.com. In 2015, he and his business partner started acquiring websites they believed had the potential to make money, through holding company Rejoin Media. The main moneymaker today is careers website CareerCloud, which contributes the majority of the business’s $100,000 of monthly revenue.

💡 Key quote: “I'm a financial guy, so I'm thinking in terms of, How do I build this blended portfolio that reduces risk across the board, so I don't have future headaches?

👋 Where to find him: Twitter | LinkedIn | Personal Website

Acquisition Tips From the Episode

Top takeaways from this conversation

📈 Plan your strategy before you make it your full-time job.

Once Mike was sure that he wanted to build his own business based on acquisitions, he started making long term plans.

At the time, he was working as a consultant to a Fortune 500 company. He switched to working for another large client, doing the same content marketing work he knew he would later be doing on the websites he bought. This allowed him to build a team and get them practiced without taking on as much personal risk.

When Rejoin Media first acquired CareerCloud, Mike and his business partner didn’t immediately quit their day jobs to do Rejoin Media full time. “I wanted to make sure the train tracks were set for the transition to happen,” Mike says. He waited until he was relatively secure financially and had a clear plan before moving over to working on his website acquisitions full time.

⚡ Stick with what you know and let the creativity come later.

The reason Mike decided to start acquiring websites was because of his content marketing experience. He knew how to take websites that weren’t making money, optimize them for Google, and monetize them through affiliate marketing. He recommends people looking into acquisitions make sure they know the area they’re getting into before jumping in.

“That's where our expertise was, and there are a lot of sites out there that fit that mold,” he says. “We were looking for something where we could do what we know, and grow.” That doesn’t mean you have to stick with the same old approach forever. In fact, mixing it up is good for business.

“Once you have enough revenue — once you have a big enough foundation — that opens up all these doorways to creativity,” Mike says.

🌈 A diverse portfolio makes it more likely that you’ll strike gold.

Mike’s time in finance taught him the value of portfolio strategy, or investing in a diversified array of assets and business models. “I'm a big believer in trying two or three things at the same time, because you don't know what's going to take off and what's not,” he says.

Even if you can’t afford three separate acquisitions in one go, Mike recommends keeping this portfolio strategy in mind long term. You could start with one, get it to a place where it’s generating enough revenue to sustain you without needing too much attention, and then find your next project.

 “If you want a good lifestyle out of this type of strategy, the end goal should be a portfolio,” he says. “It's difficult, given the changes that happen with Google, to say that one particular site is going to crush it forever.”

Episode Highlights

Inflection points from the show

[2:24] The backstory: Mike describes how his time as a prop futures trader introduced him to the world of investing and risk. He moved into content marketing and worked at a company called Soda (which was acquired in 2016), and then worked as a consultant at a large Fortune 500 company.

[7:23] A firm foundation: When you’re building a foundation based on acquisitions, start with what you know and grow from there. Diversify in terms of business model and content type.

[9:09] Finding CareerCloud: Mike found CareerCloud on business-selling site Flippa. Although it wasn’t making money, it had a good foundation SEO-wise because the previous owner had worked in media. Mike monetized by switching to an affiliate model.

[12:58] Package deal: Rejoin Media spent a sum in the mid-five-figures for every piece of content on CareerCloud, the domain name, and the podcast.

[14:27] Laying down the runway: Mike explains his slow and steady journey into acquiring and remodeling websites full time. After acquiring CareerCloud, he and his partner actually put the site on the backburner for a while before deciding to turn it into the company’s main income generator.

[17:43] Practice run: Before going full time with Rejoin Media, Mike started consulting for a company that needed him to do the same work he would eventually do for himself. So he still had steady income while making transitional steps towards his ultimate goal of living off revenue generated from websites that he owned.

[18:57] The numbers: Rejoin Media’s entire portfolio now generates $100,000 a month, mainly from CareerCloud, with a remote five-person team. The revenue is almost entirely from advertising and affiliate partnerships.

[21:55] The SEO-volution: SEO best practices change constantly, which makes it competitive. Everyone is jostling to rise in the Google rankings through backlinks. Prioritize quality over quantity in terms of the websites that are linking back to your website, and in the content you produce.

[25:15] Do your research: Find out what reporters at high authority sites want. Produce proprietary data with an angle that suits them. They’re more likely to link back to you if you give them content they’re actually interested in.

[26:39] Local news, big results: Local news organizations are always keen to find experts, and these interviews are a good way to get a high-quality backlink. Even if you’re an introvert like Mike.

[29:49] Buy over build: Mike says that even though he had to redo all the content on CareerCloud to bring it up to SEO standards, it was easier than building a brand new website. “There's a lot more moving pieces when you start from scratch,” he says.

[32:43] Always be buying: Mike is always on the lookout for new websites to acquire. Don’t put all your eggs in one basket. Even if you can’t afford to buy a diverse portfolio immediately, make that your ultimate aim. You never know for sure what will make money and what won’t.

[36:42] Follow your training: A good portfolio is diverse, but it should all be grounded in your expertise. For example, Rejoin Media has websites about solar power, exam prep and fitness, but they’re all connected, Mike says, by his expertise in “all phases of SEO, [especially] on the content ops side. Making good content and figuring out which pages matter.”

[41:43] What Mike really acquired: Now that Mike works 40 hours a week or less, he has more time to spend with his kids. His home office has an open door policy, and combining parenting with entrepreneurship is his favorite topic to write about on his LinkedIn page.

Links & Mentions


CareerCloud podcast

Quotebook - This wasn't mentioned in the episode, but is a side project Mike can pursue thanks to the freedom from his business

Mike’s recommended reading


Empire Flippers