The first time(s) I ever bought and sold a business

Hey folks, in case you missed my recent blog post, we’re on the topic of buying and selling businesses.

I’m very bullish on buying and selling businesses as a solopreneur, and have actually had two experiences of my own.

My first experience was with an online business.

This was a few years ago – I can’t even remember exactly when, probably 5 years back – when I was building my law firm and getting bored of it (because it was largely filling out the same paperwork over and over again).

I was spending my extra time learning about online businesses, digital marketing, etc., and since my firm was doing well at the time, had some extra cash to play around with.

I’d also become familiar with Flippa, one of the more popular places to buy and sell online businesses (not necessarily the best, but lots of volume on the site), and decided I wanted to dip my toes in.

So I purchased a website/blog that was getting a decent amount of organic traffic to see if I could increase traffic and start monetizing it.

To make a long story short, it didn’t work out that great because:

  • my law firm kept getting busier and making me real money, so I focused less and less on the website
  • I realized I wasn’t overly passionate about the main topic of the blog, and so my motivation decreased
  • back then I was very much a digital marketing noob, and probably just didn’t do a good enough job

So I ended up putting it for sale again on Flippa, and sold it for a bit less than what I bought it for. But learned some valuable lessons, like:

  • the process of buying and selling an online business
  • what it takes to manage/grow a content website
  • some things that worked and didn’t work
  • it’s easier to work on a business and topic you enjoy – while this isn’t a requirement, it certainly helps

These are just a few of the important takeaways from that experience, and it ended up being a relatively cheap bunch of lessons learned.

That being said, I would’ve been better off if I had some of these tips and key lessons BEFORE buying that business…

If you want to learn even more tips on how to buy/sell businesses, especially online businesses, I recently spoke to an online business M&A expert on the latest episode of the Solopreneur Grind podcast. My guest on episode 115, Yury, has been working in the buying/selling/digital marketing space for years, and shared some amazing tips on the best types of businesses to buy as a solopreneur, how to grow them, mistakes to avoid and more.

Side note: I don’t regret my experience and actually think that buying a small, cheap website/business is one of the best ways to learn as a solopreneur! Just make sure to get some tips before giving it a try and your results will probably be better than mine.

I also had one other experience, this time as a pure seller – I sold my “book of business” for my first law firm, a few years back.

Story time:

As many of you know, I started out in solopreneurship by starting my own law firm about 6 years ago (can check out the About Me page on my site here for more of a history of my career).

After a few years, I got bored and decided to start an immigration tech company to automate all of the boring parts of the business (

Initially I tried doing both – continuing to run my immigration practice and try to grow the tech company – but quickly realized it had to be one or the other.

Looking back I’m not sure I would have taken the same approach (that’s a blog post for another day), but I decided I wanted to move on from practicing law as a solopreneur and focus just on the tech.

Because I still had a good amount of recurring business and new clients coming in, I decided to try and sell it.

Note: as a service provider with no real assets, I was basically just selling my current and future clients, or what I like to call a “book of business.”

I ended up finding another lawyer to sell my book of business to, and it was a pretty good experience. There are many steps to the process, and maybe I’ll go into some detail on the different steps in another post, but buying and selling businesses is a great opportunity for solopreneurs to:

  • get out of a current business
  • fund another business or lifestyle
  • “start” a new business but skipping the first few steps
  • grow a current business by adding another one to the mix

And more.

That’s why you should definitely listen to episode 115 of the SG Podcast where I interviewed an online business buying/selling expert, and learn some tips I wish I knew before selling my first business – head over here to check it out.

Have a great day and keep grinding.

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