How Startups Move from Pioneering to City Planning

When Brendan and I launched Wistia in 2006, we had no money and no venture backing, but we had a few secret weapons. We had the newly-released Amazon Web Services — with its dirt-cheap cloud storage option, S3 — and the Panther Express content delivery network.

A few years earlier, we would have spent $500 on the bandwidth for serving up even a small number of videos. With AWS and Panther, our first month cost just $2.30.

Founders don’t always talk about being in the right place at the right time or about the massive platform shifts that made their companies viable. For Brendan and I, we saw a promising opportunity in online video, but if we hadn’t had the ability to use AWS and all the other cloud providers, it would have been impossible for us to build Wistia.

Seeing technology change so fast was inspiring. Things that were impossible 5 years before were now easy to do. This made us look at every part of building a company in a new light. We decided that we weren’t just going to build a better video platform, we were going to build a whole new kind of company, full-stop. Little did we know that in doing so, we were falling into one of the most common early-startup traps.

“We decided that we weren’t just going to build a better video platform, we were going to build a whole new kind of company, full-stop.”

In trying to build everything from scratch, we wasted lots of time reinventing the wheel and waiting for things to be perfect. To grow Wistia while staying true to our values, we didn’t always need to be pioneering — we had to figure out where we needed to pioneer and where doing so was a dangerous waste of time.

Go West, young startup!

Being on the lucky end of a tech revolution made us infectiously optimistic about process. As we looked at what other companies were doing, all we saw was outdated and inefficient systems, dinosaurs ripe for disruption.

These dinos didn’t even see it coming.

From top-down management to yearly performance reviews to one-on-ones, we made a pact that Wistia would always find a “Wistia” way of doing things.

Gradually, though, we fell into a pattern of reinventing the wheel. We started to see that we needed to focus on just differentiating the core parts of our business. Everywhere else, we needed to apply time-tested techniques.

Today we see every project we do as belonging in one of three stages:

1. Pioneering is the groundbreaking work you do as a company. You take an established practice like sales or support and focus your efforts on differentiating how you do the last 10%. When you start getting customers and finding product/market fit, you know you’ve struck gold.

2. Settling is the work you do to turn your early pioneering into a sustainable process. You’ve struck gold, and now you build encampments and make it easier for your team to mine it with tools and infrastructure. Reinventing the wheel is what happens when you think you should build the tools and infrastructure from scratch, too — you’re wasting time pioneering when you need to be supporting the pioneering that’s already been done.

3. City planning comes when a startup truly starts looking to the future. They train or find experienced company-builders who know how to implement time-tested models and best practices. Very little about city planning looks original on the surface, but when done correctly it becomes the way you continue to live out your company’s values in the long-term.

Startups are usually pioneering, settling, city planning, and reinventing the wheel all at the same time across different parts of their business. That’s normal — the big challenge is identifying when and where you should be doing what.

Pioneering: From survival tactic to core value

Wistia’s obsessive focus on making customers happy has always been one of our most defining aspects, but it didn’t come about by chance.

Bobby loves making customers’ days. Just loves it.

A year into the business, we were still acquiring customers slowly — so slowly we knew that retaining the ones we had was life or death. Other video hosting companies were out there now, and if we frustrated our customers, they would have no qualms about jumping ship.

We did know, however, that most of them weren’t able to provide the same level of personal support we could. We put a phone in the office, made it our support line, and put the number on our website. We made up a rule: every time that phone rang, whoever was closest had to pick it up.

It wasn’t something we did because we thought it was how legitimate, growing companies did support. We did it because we had no other choice — we needed to keep every single customer we acquired. As we grew, however, we realized that customer happiness had become the foundation of our business.

Where most companies saw support as a cost center, we saw it as a delight center. Every time someone called in, it was an opportunity to learn more about the problems our customers had, to find out how we could make them more successful.

“Where most companies saw support as a cost center, we saw it as a delight center.”

That customer-first thinking spread across every part of the business, from product to marketing, until we realized that what had once been a way to stay alive had become the most important thing that set Wistia apart.

Settling: Rediscovering the ancient art of organization

The problem with pioneering is that once you’ve successfully pulled it off, you can often get overconfident in your ability to invent from scratch, and subsequently mismanage the next stage. You find gold in the hills and immediately think you should reinvent everything from pickaxes to huts to road construction.

We know how tempting it is to keep pioneering. We spent five years reinventing the basic technique that’s been used to organize teams for a millennia.

Back then, when Brendan and I gave thought to the kinds of workplaces we liked, the only thing we could agree on was that we didn’t want dedicated management. The whole team should be fundamentally autonomous, and we assumed everyone on the team wanted this too — who could possibly be against autonomy?

This idea that having a flat team was core to our identity held strong even as we grew to 30 people, and the cracks started to show. In the absence of real structure, we’d started to develop an implicit hierarchy, we moved slower because responsibilities were so ambiguous, and no one knew who they could go to for help.

We knew we couldn’t keep on the way we were. But as we started mapping out our organization, we realized that structure could actually help us do more than fix the problems we had — it could help us become an even stronger team than we were while flat:

• We could use structure to spread authority evenly throughout teams, not centralize it
• We could use structure to help people make decisions faster and without the CEO being involved
• We could use structure to open up different possibilities for advancement, not make up a rigid career ladder

This was a wake-up call for a company that considered flatness central to its identity. It was the moment we realized that best practices were best practices for a reason — and that not everything was worth trying to pioneer. Organizational charts were the oldest trick in the book, and in “rediscovering” them we finally gave Wistia the structure it needed for sustainable growth.

“It was the moment we realized that best practices were best practices for a reason — and that not everything was worth trying to pioneer.”

We’d settled the hills. Now it was time to start mining.

City planning: Bringing it all back home

Once you’ve started building the infrastructure that keeps your pioneering alive, it’s time to start thinking long-term. City planning is about the time-tested techniques that companies use to get to scale and keep the business from falling apart as it grows. It’s the polar opposite of pioneering, originality-wise. And it will test your values.

City planning really tested our cultural opposition to sales. Bigger customers had started calling, saying they wanted to use Wistia but needed a salesperson to get their major stakeholders on board. We refused every time. Sales, to us, was:

• Aggressive & bro-y in temperament
• Not done in pursuit of the potential customer’s success — just their money
• Antithetical to the entire culture we’d cultivated at Wistia

Whatever we did, we were not going to call it sales. We drew up all kinds of crazy plans for a “Wistia” sales team, one that would be fundamentally different from every sales team that came before.

Then we stopped. We decided to just give it a try. Four people from our Customer Happiness team migrated over and started working with our bigger customers, and we immediately saw how wrong we’d been to fear sales. They didn’t push Wistia on anyone. They just helped customers be successful, the same way they always had.

The Wistia sales team. Look at these helpful folks!

As we’ve matured as a company, we’ve found that replicating people processes that work, rather than trying to invent them wholesale helps us move much faster. We talk to people, find out how they’ve been successful, and then replicate their methods.

“We’ve found that replicating people processes that work, rather than trying to invent them wholesale helps us move much faster.”

Wistia is a company built on its product, its customer support, and its marketing. We don’t need sales to set us apart. Nor do we need to worry about it changing our culture, because we’ve pioneered and reinvented the wheel enough to make our values clear.

The westward expansion of growth

The progression from pioneering to settling to city planning isn’t a chronology of time. It’s a series of stages, and every growing company is practicing all three of them at this very moment. The tricky part is keeping track of where (and why) you’re doing each one.

Reinventing the wheel, though it’s something you want to avoid, isn’t ultimately the worst thing you can do. When you find yourself doing it, you know it’s time to pull out the blueprints and start planning your future city. You know your core, differentiating values. And you have the hard-fought conviction of someone who knows exactly what needs to be done and how.