Brent Messenger | Crain's Pittsburgh

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Brent Messenger


Fiverr is a marketplace for digital entrepreneurs which enables freelancers to deliver millions of different types of gigs.

Fiverr opened a San Francisco office in August and named Brent Messenger as the global head of community. Messenger previously worked as a battleground state field director for the Obama campaign in 2008 and worked as a consultant during his 2012 re-election campaign. He worked at 270 Strategies where he consulted with brands including Airbnb, Lyft and SolarCity.

The Mistake

The mistake was my mindset and my perception.

During my first [political] campaign right out of college, we did door-to-door campaigns. We held events for the campaigns and we waited passively till people said yes.

We won that campaign. I don’t think we won because we were disciplined or how we were reaching out to voters. I think it was a good candidate.

But I thought, I was a big operator and I found my way into the Obama campaign.

I got in on a call with Mitch Stewart, the state director of Iowa in 2007. I’m on the call to observe and he’s taking reports on events from the night before with statewide kick-offs.

Mitch asks the first person how many people he had.

The first person says, “About 50.”

There’s a huge pause. “About 50?”

“Yeah, 50.”

“So you had 50 people confirmed to come and you got 50 to come in? The hard count is 50?”

It was this awkward moment, I had to think about what’s going on. This person was being called out.

I realized, there’s more involved in this than executing an event. They had like seven metrics. I was going to have to get more disciplined in thinking about growing campaigns and engaging with the community.

You can’t get relationships at scale without operational discipline.

The Lesson

At Fiverr, we have mass communities of people that we’re trying to organize into teams. We're trying to help and support each other. We can’t just start out by saying, “Hey everyone, go support each other!”

We have to create structure for them to engage, build them more towards enriching and beneficial activities. We’re moving towards deeper engagement. You need to think carefully about what it means to be scalable. There needs to be uniformity over what’s being asked and discipline that it’s being measured.

That’s the lesson embedded in the Iowa example. The reason why Mitch was calling him out, was not to be a jerk. He was being a funny guy actually.

We have language and a way of capturing data by doing things this way. Doing them in an ad-hoc, haphazard way is not sustainable, measurable or scalable.

What I do is wrap operational discipline around the soft art of community building. Things like having hard metrics around every activity, building an event, having one-on-ones with community members, even the way we’re sequencing things online, conversations on social media, we’re doing it for a purpose. We know how to measure the outcome. You can’t get relationships at scale without operational discipline.

Follow Brent Messenger on Twitter at @brentmessenger.

Photo courtesy of Brent Messenger.