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The Ultimate Failures that Killed My Last Startup

6 min read

This is a story that has never been shared in its entirety. Despite a successful sale of our startup, ParentsClick, to Lifetime Television in 2008, eventually it became a massive failure that very few people know about. I was a co-founder and CTO of ParentsClick, starting in 2006.

It was July 2008. We had just signed all the docs to close the sale of ParentsClick to Lifetime Television, their first digital acquisition. Our flagship products, MothersClick (a social network for moms) and Mom Blog Network (the largest mom blogger network at the time), along with FathersClick, and our nationwide network of parenting sites, were now part of the largest TV network for women, Lifetime Television.

To us, this acquisition was a match made in heaven. With our technology and online network for moms, combined with Lifetime’s massive TV reach, we thought we had an unstoppable, winning combination.

Little did I know, we were completely wrong.

We didn’t know it, but at the time of our acquisition, in 2008, Lifetime Television was simultaneously in the process of acquiring Project Runway from Bravo TV. Our acquirers had a different end game in mind for us. They knew Bravo TV didn’t leverage their website for the TV show, and Lifetime figured they could crush it connecting Project Runway with an engaging online social network for Project Runway fans.

During the fall of 2008, we opened Lifetime’s new office in San Francisco. We found a wonderful space in Potrero Hill, with huge windows, opening up to a beautiful view of the Bay Bridge in the distance.

The following year, Zynga would open a small office, across the hall from us, around the corner from Zynga’s first office. By 2010, they would lease almost the entirety of our building and would make numerous offers for our space—the most premier space in the entire building.

It was during the opening of our new office in 2008 that Lifetime told us about our first project post acquisition: the Project Runway community website, to be powered by our infrastructure.

This was awesome. Being the CTO, and now a Director of Technology for Lifetime Television, I was stoked to put our infrastructure to the works. 100,000s of page views an hour we had to be ready for, being able to withstand super-spiky TV traffic. A tech guy’s dream come true.

And then, on a beautiful day in late November, an email came across our inboxes: Stop. Change of plans.

Huh? We were full steam ahead, contractors and developers hired, and now a change of plans?

We didn’t know, but a legal battle was ensuing over the rights of Project Runway between NBC Universal, Bravo, and Lifetime.

So, we stopped the work we were doing. We were told we now needed to build a different community site, one that could unify every Lifetime TV show, not just Project Runway.

But something about the change didn’t feel right. It felt like we were trying to jam a square peg into a round hole. It wasn’t made to fit like that. Or rather, we hadn’t planned that. We couldn’t turn on a dime and deliver something in 6 weeks, could we?

Turns out, it didn’t have to make sense. Our acquisition contract and earnout stipulated that we repurpose our infrastructure for any and all of Lifetime’s needs. It never said it had to make sense.

That Christmas, we still weren’t done pivoting all of the Project Runway work for the generic Lifetime community. I still remember working on Christmas day through New Years. It was a miserable holiday to say the least.

I was working even harder than when we were a startup. I didn’t know that was possible. But this time, I couldn’t see the results or understand Lifetime’s strategy. This was crazy.

Finally, in Feb of 2009 we launched the new Lifetime community website.

And it fell flat on its face. It barely moved the needle. Users barely noticed.

The first failure.

But hey, we finished the project, all to Lifetime’s spec. I knew it didn’t feel right but that didn’t matter. It is what Lifetime had wanted.

And what about MothersClick and Mom Blog Network that Lifetime had acquired 8 months prior? They sat dormant. 8 months after our acquisition and our flagship products were left largely untouched. 8 months. That’s an eternity in the online world.

We were so busy attending to Lifetime’s own community needs, our communities were languishing.

Luckily, with Project Runway still up held up in courts, and our Lifetime community project finished, we now had the bandwidth to focus on finally combining Lifetime’s forces with ParentsClick.

We knew what needed to be done.

We had no idea that Lifetime thought they knew too.

Lifetime didn’t like our plans to improve the branding of MothersClick.

I remember them distinctly saying “can we do less pink and blue? Maybe appeal to a wider audience than moms, like women in general?”

Our site was built for moms. Our network, for parents. Wasn’t that large and focused enough?

We would kill our brand. Our messaging would be mixed. A site for moms, but also women?

So we kicked off numerous brainstorm sessions with the team at Lifetime. In San Francisco, in NYC, and weekly over the phone.

So much planning. Brainstorming. Back and forth. It was wearing me out.

And why? I never really understood.

Eventually I did. Lifetime was afraid of failure. No one wanted to take responsibility. How do you solve that? Hold meetings. Lots of them. Then there is no one to blame.

Halfway through 2009, we launched the new MothersClick. From a technical standpoint, it was faster and leaner than ever. We were finally running Drupal 6 and editing and managing content was a breeze.

But from a consumer point of view, it was a complete mess. It looked and navigated like a magazine for women. But it didn’t speak to the true nature of the content: a site for moms, by moms.

It didn’t feel right.

We had alienated our users for months working on other projects, and now we spring on them a completely redesigned site that takes away the very essence of what was working, to appeal to a larger audience of women?

An overnight success? How about an overnight failure that was a year in the making.

The second failure.

But that was only the beginning.

Soon after that launch, Project Runway came to Lifetime TV. And Lifetime TV merged with A&E Television.

It was late summer 2009, more than a year after our acquistion. And we were to start once again on the Project Runway community site. We finished it later that fall and launched it to mediocre fanfare at best. Not the smashing success like everyone hoped for.

Design by committee failure at its best.

The third failure.

From late 2009 to early 2010, we again focused 100% on MothersClick and Mom Blog Network. For the former, we simplified the site, improved the messaging, and made it feel more like a mom-site again.

It helped a little, but it was too late.

The damage was done.

This 2nd redesign of a site didn’t do anything to move the needle. Our community was gone. The internet had shifted: Facebook and mobile were booming and our approach was antiquated. We were too busy with our heads down on other projects to notice the trend.

The fourth failure.

Hundreds of thousands dollars, gone. Numerous contracting agencies fired and bridges burned. Developers quit.

My pride and joy for nearly 5 years was now a hunk of junk.

To top it off, our earnout and bonuses were tied to successful product launches for our flagship products, successful communities built, and a flourishing team.

We had none of that. And it wasn’t because we couldn’t. It’s because we listened all too closely to our bosses at Lifetime and didn’t stand ground on what we believed.

So we lost nearly all of our earnout.

The fifth failure.

We fought it. But after 2.5 years since our acquisition, the fight was weak. We were worn down.

We had built a wonderful company, small, but wonderful. Sold it to a billion dollar company. And then, watched it crumbled, failure after failure, from within.

So I quit my role as Director of Technology in 2011 and moved to Detroit and I’ve never looked back.

The burning lessons learned from this acquistion are still fresh in my memory. These are the keepsakes I’m passing on to the startup companies I’ve invested in and mentor.

And the words fail faster hang above my desk, reminding me daily of the failures endured over 3 years after what was such a smashing successful and promising exit.

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