How to Earn $200k/Year in Semi-Passive Income Through Small Business Acquisitions

Why go through the trouble of building your own cash flow when, with a little determination and a little hustle, you can insert yourself into income streams that are already happening?

That’s what Link Moser from linkmoser.com and his web design agency windhill.com have done, not once, not twice, but 5 different times, generating $200k a year in semi-passive income.

He was on the show in 2022, where he explained how he makes money with a real estate lead generation site, NHFineHomes.com, where a single referral can be worth tens of thousands of dollars.

But today, we’re diving into a different strategy: business acquisitions.

Tune in to Episode 655 of the Side Hustle Show:

specific types of businesses to acquire
how to negotiate with owners
time and logistics involved in managing his expanding portfolio

Table of Contents show

What Inspired Link to Start?

So many things in life are accidental. A local competitor — a husband-and-wife team — shut down their web design and hosting company unexpectedly.

Link, who had always competed against them for clients, only learned about it after the fact.

The business had been handed off to another company further away, and Link was left wondering, “Why didn’t they reach out to me?”

So he realized, if businesses like this were closing, why not proactively reach out and see if anyone was interested in selling?

Step 1: Sending Letters

Link began reaching out to similar businesses in his local area in New Hampshire.

He sends out a simple one-page letter introducing himself and expressing interest in acquiring their business if they were ever considering an exit.

The response wasn’t immediate, but it planted seeds. In 2014, a year or two after sending one of these letters, Link received a call.

This deal was to take over 20-30 customers with no money down. Link would pay the seller half of what he collected for 12 months, making the deal based on retention.

The seller ensured their clients had a trusted home, and Link acquired a new revenue stream with minimal risk.

Step 2: Scaling With Upwork and Virtual Assistants

Link doubled down. He hired a virtual assistant on Upwork to research local web design and hosting companies and send him potential leads at $0.25 per lead. His filtering criteria:

Less than 5 employees (too big, and it’s out of his league)
No video production work (not his thing)
Recurring revenue model (hosting, maintenance, etc.)

He tracked everything in a spreadsheet and followed up every few years. Some sellers weren’t ready then, but a future “yes” was always a possibility.

Step 3: Maximizing Responses

Link achieved a response rate of 10-12%—an incredibly high number for direct mail. He wasn’t pushing a hard sell — he was simply making a connection and positioning himself as a future buyer.

He asks questions like, “Why are you reaching out?” And that helped him gauge motivation and frame his offer.

Some owners were retiring, others were shifting careers, and some simply wanted to offload the responsibility of managing clients while still ensuring they had a good home.

Due Diligence: Making Sure It’s Worth It

Turns out, sellers are surprisingly open about their financials. People were often willing to share the number of clients they had, their recurring revenue, and what they were looking for in a sale.

Then, he would send a two-page questionnaire to collect more details and follow it up with a Non-Disclosure Agreement (NDA) to make them comfortable sharing sensitive financials.

Valuing Recurring vs. One-Time Revenue

Not all revenue is equal. Link’s rule of thumb:

Recurring revenue (hosting, subscriptions) – 1.5x annual revenue
One-time revenue (web design projects) – 0.8-1x annual revenue

He also factored in client retention rates (at least 80% of acquired clients) and structured his deals accordingly to reduce risk if attrition occurred. If clients leave, the deal needs to still make sense.

Example Deal: 2017 Acquisition

By 2017, Link had sent thousands of letters. One particularly great deal came from a small business owner who was ready to step away.

He structured the deal with a $4,000 down payment and an 18-month earn-out to acquire $32,000 in recurring annual revenue.

Minimal risk, steady income.

Tools and Tech

Acquiring is one thing. Keeping things smooth is another. Link uses:

Zoho Desk – for customer support
Virtual assistants – to handle admin work
Clear transition plan – to keep churn low

Beyond Buying: Staying Competitive

Link didn’t just buy businesses and let them sit—he kept refining and improving them.

He constantly watched what competitors were charging, what clients actually valued, and what he could do to improve retention.

You don’t want to just buy a business and hope it works out.

Day in the Life

So what does his day-to-day actually look like? Surprisingly, not much work.

Link spends his mornings checking customer support tickets, making sure freelancers are handling projects, and looking for the next acquisition.

Lessons Learned: The Surprises and Setbacks

Not every deal worked out. Some clients left immediately after an acquisition.

Even with the best research, some loss is inevitable, but structuring deals with performance-based payments can help offset the risk.

Also, relationships matter. Many sellers didn’t just want a high bid—they wanted to make sure their clients would be taken care of. Trust was often more important than money.

What’s Next?

Link isn’t slowing down. He’s looking at bigger acquisitions, possibly branching into brick-and-mortar businesses, and always keeping an eye out for more passive income streams.

Diversification is key—one income stream could dry up, but with multiple sources, financial stability remains strong.

Link’s #1 Tip for Side Hustle Nation

2025: “Get out there and do it.”

2022: “Don’t look at failure as a bad word.”

Related Episodes

For more strategies like this, check out:

Big thanks to Link for sharing his insights! If you found value in this, share it with a friend who’s looking to build semi-passive income.

Episode Links

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