10 Lessons Learned from Multiple Six-Figure Exits

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When I sold my first website in 2010, I had no idea what I was doing. I sold the site for $50,000, but the lessons I learned were much more valuable than the money.

My first six-figure exit came in 2013 when I sold a blog for $500,000. Since then, I’ve sold five other online businesses for six-figure sums.

Over the years I’ve learned a lot of valuable lessons that helped with other businesses and exits. This article shares a random collection of those lessons. Hopefully, they’re relevant and applicable to your situation.

1. It Only Takes One

Valuations of websites and online businesses can range drastically. Sure, there are some standard factors that influence valuations, but everyone has their own opinion. At the end of the day, a website or business is worth whatever someone is willing to pay for it.

When you’re selling a website or online business, it only takes one buyer.

In the spring of 2023, I sold a personal finance blog I’d worked on for several years. Personal finance blogs tend to generate a lot of interest from buyers, and the broker I was working with (Brad Wayland from Quiet Light) felt it made sense to go with a higher asking price because of the niche.

With the higher valuation, the listing generated less interest than other content sites priced at lower multiples. But in just a few weeks, I received a strong offer close to the list price.

Despite less interest overall, the listing generated enough interest from qualified buyers that it sold for more than I expected. Most potential buyers thought the valuation was too high, but it doesn’t really matter what the people who didn’t buy the business thought.

Of course, having more interest creates competition and may lead to higher offers (in my case, there were two offers, and I accepted the higher one). But the point is that a single buyer can drastically impact valuations and selling prices.

2. There’s Plenty of Room for Small Players

Many bloggers and online marketers look for small niches with low competition. Succeeding in these niches is easier than competing for attention by focusing on more popular topics.

That approach can work, but there’s plenty of room in crowded industries and niches for small players like myself to succeed.

All of my successful websites and online businesses have focused on popular topics like web & graphic design, photography, travel, and personal finance. I’ve tried creating sites on low-competition niche topics, but none amounted to anything significant.

My sites in the popular niches were very small compared to the leading sites. However, popular topics offer so much potential that it’s possible to have a lot of success even as a minor player.

💡 You don’t have to control a major part of the market. You can do very well by having a small piece of a much bigger market.

These popular niches/topics are also ideal when selling your site. There are more buyers interested in these types of sites than there are for sites that focus on very tight niches without much room for growth.

3. Leverage Your Platform Before You Sell

If you have a successful website or email newsletter, you should consider using it as a springboard to your next project selling.

For example, my first site was a web/graphic design blog. During the last year I owned the site, I started a new site on photography. Design and photography somewhat overlap, so I was able to leverage my existing audience and network connections to get the new site off the ground pretty quickly.

By the time I sold the design blog, the photography site had a growing email list and was making money every month. I wouldn’t have had the same quick success with the photography site if I had started from scratch.

Then, during the last year I owned the photography site, I used it to launch a new blog focusing specifically on landscape photography. Since many people on my photography email list were interested in landscapes, cross-promotion was easy and effective.

At the other end of the spectrum, I didn’t decide to launch Flip My Site until after I’d sold my finance blog. If I had planned things out better, building the initial audience at Flip My Site would have been easier because I might have been able to leverage that audience.

Before you sell an online business, I’d strongly encourage you to think about any future projects you’re interested in and see if there’s a way to leverage your existing platform for faster growth.

4. A Good Broker is Worth The Fee

Many people who sell websites or online businesses avoid sellers because they don’t want to pay fees or commissions to the broker. I think that’s usually a mistake.

While broker fees can be significant, the amount you take home after the fees is what really matters. A good broker may be able to sell your online business for a price that more than covers their fees.

I’ve sold websites privately through my own network, on Flippa, and through a broker. The two deals that have gone through Brad Wayland and Quiet Light brought the highest multiples of any of my sales. In both cases, the higher sale price more than justified the broker fees.

I’m 100% confident that I wouldn’t have been able to sell either site on my own and walked away with more money. In fact, I had private offers for both sites before listing them with Brad, and those offers were much lower than what Brad was able to get.

It makes sense to sell your site without a broker if you have an ideal buyer in mind and are confident you’re getting a good price. Otherwise, you’re probably better off going with a broker.

5. Your Network Matters

My two biggest sales (in terms of the sale price) were to people in my professional network. The stronger the network you have, the more likely you are to find a qualified buyer without needing a broker or marketplace.

In the situations when I listed sites for sale with Quiet Light, I didn’t have anyone in my network who would be an ideal buyer at the price I wanted.

If you want to buy or sell online businesses, building your network should be a priority.

6. Trust is Essential

The acquisition process requires trust from both sides. And when trust is present, you never know what it will lead to.

In 2010, when I sold my first website, I didn’t know the buyer before the sale. But we had a good experience working together and stayed in touch.

In 2013, I sold another site to the same buyer (he had a partner for this purchase) for $500,000. In 2016, I sold another site to the same buyer (without a partner) for another $500,000.

He’s told me several times over the years that he liked working with me because he trusts me, and I feel the same way about him.

If I had tried to pull something over on him during the first sale, or if I hadn’t been good to deal with after the sale, he wouldn’t have bought from me again.

💡 People choose to do business with others that they like and trust. If you’re trustworthy and good to work with, doors may continue to open in the future.

7. When in Doubt, Disclose Upfront

Buyers have a lot of concerns when they’re evaluating potential acquisitions. Red flags can kill the deal. It can be tempting to try to hide your business’s flaws, but they’re likely to come out during due diligence.

It’s better to disclose any issues to potential buyers upfront rather than waiting for them to find the issues on their own. Has your site experienced a significant drop in traffic? Conversions dropped? Been hacked?

Disclosing potential issues upfront shows that you’re honest and trustworthy. Plus, you can control the messaging and also share how these issues may already be resolved or what you’ve done in response to them.

This also applies to terms of the agreement, like non-competes and other details that could be a sticking point. Most buyers are willing to work with you if you discuss these issues upfront, but it could blow the deal if you don’t bring it up until just before the closing.

8. Timing is Critical

It’s much easier to sell a site that’s growing (in terms of traffic and revenue) than one that’s declining. Sites that are trending up are likely to sell for higher multiples, and sites that are trending down are likely to sell for lower multiples. With that in mind, you want to sell while your site is trending up.

If you’re considering selling your online business at some point in the near future, look at the year-over-year trends. Are traffic and revenue going up or down?

If they’re trending up, you may want to think about selling while things are going well. If they’re trending down, you should work on reversing those trends before trying to sell.

Aside from your business’s trends, timing is also important for industry trends and economic factors. For example, Amazon FBA businesses were selling for higher valuations a few years ago when aggregators bought up everything they could find, and the economic trends were more favorable.

The second half of 2023 has turned into a buyer’s market with businesses taking longer to sell and valuations decreasing slightly.

Of course, you don’t have control over industry or economic trends, but it’s helpful to remain flexible and adapt to them. If the current timing isn’t favorable for selling, hopefully, you can wait until the timing is more advantageous.

9. It’s Important to Consider Taxes

Talk to an accountant or tax professional before selling a business. The larger the sale, the more important this is. You don’t want any unpleasant surprises related to taxes.

It’s helpful to run a simulation or estimation of your taxes to see what you should expect to owe.

It’s also worth considering the impact of being paid in one lump sum at the time of the sale vs. being paid over several years. Most sellers want all the money upfront, but there may be tax advantages to spreading it out.

Of course, taxes are just one factor to consider when negotiating the terms of a sale, but without a professional’s insight into your situation, it’s hard to know what scenario is best for your taxes.

10. Starting Over is Hard

What are your plans for after the sale? If you’re like most online entrepreneurs, you’ll start something new.

If you’ve been running your existing business for a while, you may have forgotten how challenging it can be to start a new online business from scratch. Most online businesses, but not all, require a lot of work before they pay off.

I’ve started over several times after exits, and each time, I’m reminded how much work it takes to build a new business from the ground up.

As an alternative, you could take some of the money from your exit and use it to buy an existing website rather than starting from scratch. This allows you to skip ahead and start generating revenue immediately.

Final Thoughts

Growing and selling an online business provides plenty of excellent learning opportunities. Thankfully, these lessons can be helpful in future ventures (although I admit that sometimes I’ve made the same mistakes multiple times). Hopefully, the lessons covered in this article can be helpful for you as you grow and sell your business.