On Selling Your Website — It's OK to Be a Lifestyle Business

Thoughts on whether I should've sold ReadWriteWeb when I did, given what happened to the site over the next decade. Do I regret selling?

By Richard MacManus |

Ngake and Whātaitai the taniwha of Wellington harbour

Instead of the latest installment of my serialized Web 2.0 memoir, this week I want to talk about the experience of selling a tech blogging business — and the after-life this can have, which sometimes (maybe most of the time?) can be more hell than heaven.

Of course, I am referencing the blog post I put up yesterday about ReadWrite having been sold yet again — this time to a super-dubious gambling marketing company called ClickOut Media. This discovery comes at an awkward time in the chronology of my memoir project, because I’m midway through telling the story of how I nearly sold ReadWriteWeb in early 2008 to Ziff Davis Enterprise. The next installment, part 31, tells of my travel to New York in May 2008 to undergo due diligence with ZDE and its owner, the private equity firm Insight Partners.

Spoiler alert: I pulled out of that deal in mid-July for reasons I will get into in the next few installments. After that, I continued to run ReadWriteWeb as an indie company for a few more years. Successfully, too; so in hindsight I was very relieved I turned down the ZDE deal.

That said, post-July 2008 I also continued to struggle with scaling RWW, due to a variety of factors including my geography and my personal life. One example: I wasn’t able to hire my staff as full-time employees because of international taxation laws, which was a source of deep frustration for me — especially when TechCrunch began picking off my writers one by one!

Again, I will explain all of this in the remainder of my memoir. But in short, I felt that selling my company at the end of 2011, to SAY Media, was the right decision at that time. I was confident — or maybe just hopeful? — that SAY Media would follow through on their promises and help me scale RWW.

Well, there’s a saying: “history will be the judge of that.” And the past 11-12 years of RWW’s history has not been good. You can read my post about ClickOut for a summary of what I think of the various owners RWW has had during that time. But maybe you’re more interested in my answer to this question: do I regret selling RWW?

The honest answer is that as every year passes, the more I regret letting go of the tech blog I started in 2003 and grew into a thriving small business. The thing I most regret is not giving more consideration to turning RWW into a lifestyle business. I wish I hadn’t been drawn into the Silicon Valley mindset of ‘scale at all costs’. I address this in chapter 15 of my book; but we’re currently only in chapter 10, and I think I need to reveal my thoughts on it now, given this current ClickOut drama.

Here’s what I wrote in chapter 15, which is set in April 2010. At this point, RWW was still growing strongly.

Looking back on it as I write this, I regret not giving more consideration to the option of treating RWW as a lifestyle business. I was making an excellent personal income from the blog and providing employment to around twenty other people; there was no immediate danger of this changing. I recall discussing the lifestyle-business scenario with Sean several times back then—I think he felt a moral responsibility to remind me of it on occasion. But every time, I dismissed the option. Something was driving me to continue growing the business every year, and I couldn’t see past that as a goal.

I’m a quietly competitive person, and so I enjoyed measuring our success and influence against big hitters like TechCrunch, Mashable, and GigaOm. The prestige of running one of the top ten or fifteen blogs in the world was another driver—I didn’t want us to slip back down the Technorati charts. And growing by a factor of two or five every year was just what was expected of tech or media startups at this time. Related to that was my wish to hold onto Sean and Marshall, my two key employees. Both were ambitious people—Sean’s career goal was to become a VC, while Marshall keenly wanted to be part of a startup success story. I felt that neither would want to work for a lifestyle blog, so I’d most likely lose their services if I chose to go that route.

I had my own personal reasons to chase growth, too. To reach a divorce settlement with my ex-wife, I’d either need to sell the business or raise VC money to pay her out—and both relied on revenue growth. Her lawyers had specifically rejected the option of me giving her an ongoing equity stake in the business. It had been made clear that, one way or another, I’d have to give her a large sum of money.

So for all the above reasons, I didn’t view RWW as a lifestyle business. More’s the pity, as running a tech blog was a life I enjoyed. Despite the daily business pressures, I felt I was born to be a tech blogger, and I wanted to continue doing it.

Now, it took me another 18 months or so to make the decision to sell RWW, but the point of the above extract is that I had at least considered the lifestyle business option. But I chose to continue pursuing growth and scale. (And granted, we’re talking tech blog scale, not unicorn-level scale — but it was a growth mindset nonetheless.)

Given what ReadWriteWeb morphed into after I sold it and lost control of the site, I regret that I didn’t listen to that inner voice telling me it was ok not to pursue growth. I also regret letting down my RWW colleagues in 2011 — indeed, one emailed me yesterday to say they had misgivings at the time about what SAY Media would do with their jobs and to the business. So, I have to deeply apologize to my fellow RWWers back then. I honestly thought selling RWW to a US media company would give our staff more stability and help us keep up with the TechCrunchs and Mashables of the world. But that didn’t happen.

The obvious flipside is that I did get a nice chunk of money from the sale of RWW, which allowed me to buy a good home for my family, etc. It also allowed me the freedom to later pursue other types of writing that I’d always wanted to do (I’ve published two books since then and am serializing my third right now). So I don’t want to downplay the benefits of selling when I did.

Also, if I had chosen to make RWW into a lifestyle business, there’s no guarantee the business would’ve survived or that I would’ve been happy.

But if there is a lesson here for other entrepreneurs or media operators, I would just say this: don’t discount lifestyle business as an option. If you’re employing yourself and 15-20 other people, that’s more than enough for a successful, satisfying business — and life.

Lead image: Ngake and Whātaitai the taniwha of Wellington harbour; this is a photo I took in November 2010 on Petone harbour, near my home at the time in Lower Hutt, New Zealand.

Next up: back to my Web 2.0 memoir, with Part 031.

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