Flipping Sites vs Holding Sites: What's The Best Option For You? | Skipblast

Flipping Sites vs Holding Sites: What’s The Best Option For You?

Recently I was asked about flipping vs holding sites. And if you spend any time in SEO groups or forums, then you know that this is a common topic of discussion.

Often, some self-righteous asshole pops up in the comments and declares that there MUST be something wrong with a site for it to be sold, cause only an idiot would sell a site that’s a regular earner.

But the truth is that only an idiot would make that declaration.

So, let’s dig into this a bit more, shall we?

**And as always, I’m an affiliate marketer and this post probably contains affiliate links, meaning I will be compensated if you make a purchase after clicking on my links

Why Sell A Successful Site?

I think there are a lot of people who just can’t wrap their mind around the thought of selling something that’s making you regular money. After all, if you had a cow that regularly produced milk that you sold at the farmer’s market, then why would you sell that cow?

Now, I don’t fault people for this line of thought.

But at the same time, I feel like this way of thinking is how people end up stuck in the same desk job for 40+ years of their life.

It’s comfortable and safe to have that regular income, right? But is it really the right move for most people?

So, let’s get back to this hypothetical cow. Now, why would I sell this milk-producing money cow?

  • I know that this cow isn’t gonna make milk forever, and when that happens the value of the cow declines
  • I know that this cow could die at any time for no real discernible reason, and then I’d be left with nothing
  • I know my limitations, and I don’t have the skills/money/interest in breeding this cow to make more milk or turning that milk into cheese so that it becomes a more valuable asset
  • I know that this cow is very valuable right now because it makes money, and I can make the same amount selling the cow now that I can make in three years of selling it’s milk
  • I know that if I sell this cow for 36x the monthly milk income, then I can live comfortably for a time while using some of that money to buy some chickens, maybe a pig or a goat and by the time my cow selling money dries up I’ll have a new income stream. Or, I could even buy a tractor and some seeds and have a totally new income stream.

If you can’t tell, I’ve been playing a lot of Stardew Valley again.

Anyways, you probably already know that I build and flip sites as a business model (and recently released a course on this topic.) So, let me talk about some of my motivations.

First things first, flipping sites is a great way to build wealth since they sell for such high multiples. But that’s not the only reason I do it.

The very first site that I sold back in 2014 was a growing site, but I really wanted to take a RTW trip and not have to dip into my savings for it. So, I flipped the site.

One of the sites I sold was a multi-niche site, and I just didn’t know how I was going to level up the monetization of a multi-niche site, so I flipped it.

A few years ago, I started a golf site as a live case study for students. And I fucking hate golf. After a while, competition was on my heels and my interest was zero, so I flipped it.

I had a very successful site in the paddleboard niche a few years ago, that I considered hanging onto for the long haul. I knew that to scale it up required either adding an ecommerce component to the site, making my own boards/gear, or starting a rental company at the beach (or other waterfront).

I contacted the companies making the boards that I wanted to sell (or rent out)…and they would only let me do it if I had a physical location with a storefront. After I couldn’t find any commercial storefront real estate to rent within my budget I decided to flip it (and the new owner tanked the site, for shame).

I once had a water softener site that repeatedly got hit by negative SEO that I sold simply because it just wasn’t worth the hassle of dealing with the negative SEO attacks.

And I’ve sold several sites just due to growing bored with the niche.


Because I know that when I get tired of a site, then I won’t be motivated to work on it, which means that it will die a slow death if I don’t sell it.

Currently, I have 14 sites on my list to grow and flip. I have one site on my ‘maybe I’ll flip it, or maybe I’ll keep it’ list. And I have 5 sites on my grow and hold for the long term list.

So, why do I have these 14 sites that I already know that I’m going to sell?

Because when I grow a site and flip it, then I get that bulk payout of 3 years of monthly income in one balloon payment.

Sometimes those sales give you ‘fuck you’ money and sometimes it gives you a nice amount to invest in other sites or other income producing streams.

I always save a little from a sale and then I invest the rest in other projects (unless I’m doing it for a big trip, like the RTW trip).

But here’s the thing about flipping sites that are bringing in steady money – I don’t fear the regular income loss.

In fact, in 2016 I sold almost all of my sites just cause I thought it would be a fun challenge to try to build everything back up from almost nothing.

So, I guess those of us who flip sites that have steady income are just less risk averse than most people.

Why Keep A Successful Site?

If you’ve got a site that is regularly bringing in good money, then you get in this really comfortable place.

You may really enjoy the site, or you may just really enjoy the security its steady income brings. Or it may be both.

I mean, doesn’t it sound great to have a site bringing in good money every month that’s on a topic you enjoy and that likely requires little upkeep.

And ideally, if you keep adding content to the site, then it just grows more and more right?

It’s a nice gig, if you can get it.

But, in my opinion, this house of cards is too risky.

Why I Don’t Hold Sites For The Long Haul

If you have a standard affiliate site or content site, then I see holding onto a site as a non-safe option for the long term.

I mean, I guess it’s as safe as when you dedicate your life to “the man” and work at the same company …. until you’re surprised when they lay you off outta the blue.

Nothing is certain or secure when it comes to those cookie cutter affiliate and content sites.

Your white hat site where you’re a world-renowned expert can get taken out in a Google update for no fucking legit reason. And then what?

You’re fucked, that’s what.

You also never know when a big brand is going to decide to enter your niche and just dominate the SERPs and destroy your rankings.

This is why I don’t tend to hold sites for a long period of time.

Why I Might Hold A Site For The Long Haul

So, I told you above that I sold almost all of my portfolio in 2016. But I do have some older sites in my current portfolio.

Why have I kept those?

Because they’re not your cookie cutter affiliate and content sites.

I keep sites with the potential to go big – and when I’m up to that challenge.

Remember the paddleboard site I told you about above?

That was a long term hold for me until I hit that wall of needing a storefront but not finding one in the price range I was comfortable with at the time.

So long holds for me are when it’s a niche that I won’t grow bored in and when I can cultivate multiple traffic streams and income streams.

And, most importantly, when the site has the ability to support a real world business. I was all in on selling paddleboards direct or having a rental company, but only if I could make it fit within my target budget.

When you see a site has a real business potential and not just a site potential, that’s when I think you should want to hold onto sites.

6 thoughts on “Flipping Sites vs Holding Sites: What’s The Best Option For You?”

  1. Hey Shawna,

    14 sites seems like a lot to manage. Curious to know if you outsource the mundane tasks or if you manage it all independently?

    Also, when you do decide to sell do you try to build the revenue up to a certain walk away amount where you have the multiplier x ( monthly revenue target )?

    I currently have 5 in my portfolio and one I might sell this year once I drive the revenue up a little more.

    • Hey Samuel,
      Sorry I missed this comment until now.

      I do manage it all independently. I have a lot of spreadsheets to track everything. Content and some links are really the only things I outsource.

      I always have income goals when I start a site to flip. Sometimes I have to adjust those goals, but for the most part I calculate it out based on a 30x multiple.

  2. Have you ever been interested in building a marketplace to sell your sites? 10 to 15 percent commissions to brokerages that take money off the top of your hard work is ridiculous. Even brokerages selling brick-and-mortar businesses that take months to transfer and much more due diligence only charge 10% commissions. Between the brokerage and the government, online marketers take home about 60% of the sale price. I’m considering selling two sites worth a combined $1.8M, and I’m seriously considering building a new platform that charges less than 10%. Fuck EmpireFlippers, FEI and the rest.

    • Yeah, that commission is pretty high. I actually did have something like this going several years ago but it wasn’t really worth the time it took me. I ended up closing it down after like a year.

    • It really just depends on your budget. I build most of my sites just cause that’s the system that I’m comfortable with, but when I find an undervalued site then I’ll buy it if I think I can boost the income for a flip. So I think at the end of the day it’s whatever your budget allows for and what you’re most comfortable doing.


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