Why and How I Sold a Content Company, The Write Life

September 19, 2021

Eight years ago, I launched a website for writers called The Write Life.

Early this year, I sold the business. It felt like a beautiful milestone! It was satisfying to achieve an acquisition after working on the site for years, rewarding to put some money in the bank, and freeing to make space for a new project.

The Write Life community

I decided to sell the brand for one simple reason: I want to create room in my brain to build something new.

More than a decade into my entrepreneurship journey, I was ready for a new challenge. And because it’s a seller’s market — online content companies in particular are in demand — the timing felt right.

My husband asked me recently, “Do you miss it?” And the answer surprised me: “Actually,” I said, “I don’t.” I thoroughly enjoyed building this brand and community, but my tendency is to look forward, not back, and I’m excited for my next company.

When you work for yourself, it’s easy to let milestones pass without celebrating them. That has felt especially true during these pandemic years, when the ways we might have previously celebrated — with a dinner out or a trip — aren’t as appealing.

I see documenting what happened and sharing it with you as a way to celebrate. I always enjoy looking back on these posts years later and reliving details I would’ve otherwise forgotten about.

In this post I’ll share some of the background of how I launched and grew The Write Life, then dive into an FAQ about how I sold the business. In addition to marking this milestone for myself, I hope this piece is helpful to others who want to sell their business or dream of building a business that could sell one day.

The story of The Write Life

I launched The Write Life in 2013, when I was operating a small agency that ran blogs for businesses, as a way to apply the systems we used for our clients to an asset we owned. 

I considered the site a fun challenge, a place to experiment with new content strategies and learn about audience growth. It also helped me attract freelance writers and editors, whom we funneled towards our agency work. 

By launching the site, I bet on myself. An acquisition was not on my radar in the early days.

The years following were busy, and there was more than one occasion where I almost wound down the site because I didn’t have the brain space or energy to run it. 

In 2015, I sold my blog-management agency through an acqui-hire to a media company called The Penny Hoarder, then went in-house to grow the content team there. I had two babies while in a leadership role at that fast-growth startup, which left zero time for side projects. Rather than let The Write Life die, I minimized expenses, beefed up the systems documentation we’d developed over time, and asked an editor I’d worked with previously to run daily operations, setting the expectation that most decisions would have to be made without me.

When I left The Penny Hoarder in 2019, it was nice to have The Write Life waiting for me, a place to put my creative and business energy while I pondered what to build next. I used the site to practice my SEO skills and developed a plan to significantly increase revenue from the business. 

Yet something interesting happened when I looked hard at that plan: I realized I didn’t want to execute it. The topic of freelance writing felt aligned with who I was a decade ago, not who I was then. So many other business ideas excited me, and I did not want to continue to put time and effort into this one just because it was already on my plate.

At the same time, I felt called to simplify my life, to do less.

With a family that requires a decent chunk of my brain, I no longer had the capacity to juggle lots of revenue streams, at least not in a way that felt good to me. I knew that if I wanted to start something new, I should let go of other responsibilities.

In that way, deciding to sell the business felt like a relief: It opened up bandwidth for new, exciting opportunities that would stretch me in different ways.

If you want to understand more about how I grew The Write Life, here are some posts I’ve written about it (I cringe at some of the posts I wrote years ago, but they offer insight into my thinking):

FAQ: How I sold this online business

Now that you understand how I grew this company, here’s a run-down of how I sold it.

The sale included a confidentiality clause, which is typical in private deals and means I can only share certain details. I believe transparency helps others, so I’ll share what I can, but I’m limited by my agreement.

Q: Did you work with a broker or list the business on a marketplace?

A: No. Brokers are more typical for deals of this size when the seller can’t find a buyer on their own. I had several interested buyers, so I didn’t need to go through a broker or list the business on a marketplace.

Q: How did you find a buyer?

A: Quite a few interested buyers have approached me over the last couple of years about buying the site. They were interested in an acquisition for two reasons: 1) the brand’s reputation in the writing space and 2) the brand’s competitiveness in search. Because The Write Life gets a lot of search traffic, anyone who’s trying to rank their own website for writing terms would likely notice it during competitive analysis.

Several times in the months leading up to the sale, I mentioned casually to an acquaintance or partner in the writing space that I was planning to sell, and they’d surprise me by saying they wanted to throw their hat in the ring.

Some of those offers didn’t end up being competitive, but it was nice to know I had options, and in the end it was a word-of-mouth introduction that led me to the winning bidder.

Q: How did you choose a buyer?

A: I ran a bidding process in which I asked all of the companies that had expressed interest in the site to submit a private bid. 

By this point I’d had multiple conversations with each interested party to review the site’s assets, and they knew the price range in which I expected to sell. Out of the submitted bids, I chose a winner based on price, payment structure (i.e., cash vs. stock, or cash up front vs. an earn-out), which company I thought would best serve our writing community going forward, and which company I expected would make the transfer process least stressful for me.

Another seller might have chosen or prioritized different factors. But since this was my sale, I got to base the decision on what mattered to me.

Q: Who bought the site?

A: A publisher that owns several writing sites. (I’m not allowed to disclose the name of the company.)

Two months after the sale, the company that purchased The Write Life resold it to a different company. I was surprised by the subsequent sale, but once I had handed over the company, I was no longer involved and all decisions were out of my control.

Q: What information did you share with potential buyers ahead of bidding?

A: I created a spec sheet, basically a marketing document, and shared it with each company that expressed interest in purchasing the site. It wasn’t fancy, a simple Google Doc, but it was comprehensive. It covered everything from web traffic to revenue and profit to why I wanted to sell the site and how I thought the right buyer might monetize it. 

I took extra care to flesh out details around our search traffic, since search rankings were a big piece of what made the asset valuable. Before offering this document to potential buyers, I shared it with a few friends I consider knowledgeable about online business, and they provided feedback that helped strengthen it. I got some great ideas for what to include from a free webinar from Flippa, a marketplace that connects sellers and buyers.

My goal with this spec sheet was to be as transparent as possible. I wanted potential buyers to have a complete picture of the site and understand its strengths and weaknesses before making a bid, to avoid surprises later. I think bidders appreciated this approach, and it helped establish an initial relationship of trust.

Q: Was the sale process stressful?

A: Only a little. I really enjoyed it as a chance to learn.

There were a few twists along the way, but overall it went smoothly. One factor that helped is that I’m fairly organized, so all of our financials and process documents were in good shape and easy to pass along. That also helped prevent surprises during due diligence.

The post-sale period was challenging emotionally when my buyer resold the site, but I felt good about reframing that as a learning experience. It served as a reminder not to get too passionate about any business if there’s potential to sell it, because once money’s been exchanged, the new owner has full reign. I appreciate this lesson as I begin building my next company.

Q: How did you know how to sell the company?

A: I knew some ahead of time and learned the rest along the way. I’d sold a business before; my content agency was acqui-hired in 2015. While I could apply some learnings from that previous acquisition, an acqui-hire works differently than an asset sale, which is how I wanted to sell The Write Life.

I found these people and resources helpful:

  • Bryan O’Neil, an online business acquisitions expert who has experience with this size of deal: I found Bryan on Clarity.fm and paid him to answer my questions for an hour. He was super knowledgeable and helpful about specifics, including how to structure the bidding process.
  • Andrew Ritter, an M&A lawyer with Wiggin & Dana: In addition to helping with legal documents, he answered a lot of my questions about what’s typical for these types of asset sales.
  • Flippa, a marketplace that connects buyers and sellers for online businesses: I attended its free webinar that outlined how to maximize value as a seller. I considered listing the business on this platform, but in the end decided to connect with buyers independently.
  • John Warrillow’s books: Built to Sell and The Art of Selling Your Business are both good reads. I used Built to Sell years ago when I systemized a business for the first time. The Art of Selling Your Business is better suited to $1M+ sales, but I still took away insights I was able to apply to this deal.
  • Podcasts: I got lots of ideas from… 

In some cases, I simply followed my gut.

When you’re selling a business, at least one of this size, it makes sense to follow some best practices, but in the end you get to make the rules. It’s your asset to sell, so you get to decide how to go about it. 

Q: Did you use a lawyer?

A: Yes, I worked with Andrew Ritter of Wiggin & Dana. He was an excellent advocate and took the time to teach me along the way. A NY-based M&A lawyer isn’t cheap, but it was well worth $10,000 to do this deal properly.

Q: How much did you sell the business for?

A: Mid-six figures. (I’m not allowed to be more specific.) 

I thought about sharing this information at the top of the piece or even in the headline since it’s often the first piece of information readers look for after a sale. But the truth is, transitions like this are about more than money.

I also considered not sharing this information at all, and keeping it private. But I think it’s helpful for those of you who have built or want to build similar businesses to know how much a content site can sell for. 

Q: What did you learn throughout the process?

A: One of my biggest takeaways, both from this sale and my previous acqui-hire experience, is that multiples are useless for valuations

Yes, they provide insight into industry trends and can help set some expectations on both sides. But when it comes to sale price, the only things that really matter are how much your buyer is willing to pay and how much you’re willing to sell for. 

Another good tip: Hire a lawyer before you sign an LOI, or Letter of Intent. First-time sellers often make the mistake of signing this initial document and then seeking legal representation. But that letter can limit your options in a final agreement. I was fortunate to have Andrew help me with this piece early on.

Big picture, this felt like a validation that investing in yourself is worth it. In the early days, it felt self-indulgent to put revenue from my agency into growing this site until it could pay for itself. But that urge to put our processes and network to work for an asset I owned (rather than only building client assets) was spot on, and it paid off over time.

Q: What business will you build next?

A: While going through this process, I was struck by just how little helpful information I could find online that’s relevant for six- and seven-figure acquisitions. Most of the media’s emphasis is on much bigger deals that are venture-backed.

I see this as a huge hole in the market. Six- and seven-figure deals are more common and more attainable for entrepreneurs, and arguably more enjoyable to aim for, as they don’t require the “grow at all costs” mindset. A mid-six-figure acquisition might not mean you’re set for life financially, but it can provide life-changing freedom and position founders to create another business that has a meaningful impact in the world.

I’m using this personal pain point as a leaping off point for my next business venture: They Got Acquired, a media company that covers deals between $100K-$50M and shares details that are helpful for everyday entrepreneurs, not just unicorn-hopefuls.

Landing page for They Got Acquired

We’re working toward a launch in late 2021.

To be notified when They Got Acquired goes live, add your email:

Got other questions about the sale? Feel free to ask here in the comments or on Twitter.

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    9 Replies to “Why and How I Sold a Content Company, The Write Life”

    • Thanks Lexi, for this clear & authentic description of your most recent career pivot. As always, your self-awareness & creativity shine through. And now I can’t wait to watch your next moves.

    • Hayden says:

      Really enjoyed this, thanks for sharing!

    • A great read! I’m excited about your new venture, too! Feels like a very natural transition, and a great jumping off point.

      Building a site like The Write Life is a remarkable achievement, and I’m glad you found a reasonable exit!

      As an idea for your new venture, I’ve personally been approached with surprisingly high offers for paid subscription newsletters (both on platforms like Substack and custom built ones on Ghost).

      This may be a perfect segment to interview. Especially because unlike website creators, the burnout rate and content demands are considerably higher and an acquisition is their only real option.

      Just a thought. Best wishes!


    • Gina Horkey says:

      Cheers Lexi on a job well done – both in building/selling TWL, but also in this writeup!

    • Tomas says:

      Congrats Alexis!

      Thank you for being transparent and sharing your thinking and details. I can highly identify with the need for mental space for new projects. I feel like I have 3-4 years on a single project until I get bored and tired.

      Best of luck with your new venture!

    • Hey Alexis,

      Been following you on Twitter for quite sometime and loved the way you document your journey (work life) on it.

      This acquisition case study is clear, precise and inspiring.

      I am too connected with my web assets and that refrains me from selling them. I wish I don’t get too emotional with these because as a media company these web assets are just products of ours.


    • Affan Khan says:

      Great read!
      Keep up the work, Alexis!

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