How To Be Just Naive Enough To Make An Education Startup Work

Launching an education startup may seem like a fool’s errand. Treehouse founder Ryan Carson might have the secret.

How To Be Just Naive Enough To Make An Education Startup Work
[Image: Flickr user stevendepolo]

Trying to make education affordable seems impossible. In fact, you could argue that any kind of education startup seems nearly impossible: Technology’s short-term expectations aren’t typically conducive to the long-term quality education requires.


So it was with no small dose of foolishness that developer Ryan Carson set out building Treehouse, the new-tech-focused education platform, now 70,000 students strong. “I never think about how hard something is going to be,” he says. He just does it.

Early Ed-Tech

“Launching Treehouse was very naive,” he says. “It’s a very hard problem–teaching people online, getting them job-ready and then putting them in jobs. The challenges were and are still enormous.”

At the beginning of the ed-tech startup trend, when other coding schools like Codecademy were flashing shiny badges but failing to provide optimal educators and actionable results, Treehouse began offering tutorials from actual experts and teachers as well as training tech companies’ employees. “We’ve been doing it three years–which is kind of a long time for me—and we’re just now starting to crack it open,” he says.

The company now offers tutorials for programs including CSS, HTML, Ruby, JavaScript, iOS, and recently added WordPress. Results show that the average Treehouse education provides a $10,000 salary increase while it is used for employees of companies like Twitter, Square, and Aol.

Marketing ed-tech company Copyblogger was founded upon similar ideals to that of Carson’s. Cofounder Sonia Simone says naiveté helped her create the early-adopting marketing education platform back in 1998 with the idea of putting an educational platform online right away and figuring out the rest later. Now one of the most-used online marketing tools, it seems to be working out.


“I would have never expected this company to work,” Simone says of Copyblogger. “We’re a technology company, a marketing company, and an education company so it’s a constant challenge to mesh all of the components together.”

But Simone’s experimental ideas were once discouraged at her previous corporate job–something Ryan Carson hopes to avoid as Treehouse continues to grow.

Getting Rid of Management–Like, Tomorrow

Fearing that close-minded corporate structure that Simone experienced, Carson enacted a no-management workflow to his 70-person company last June. It was a move that came as a shock to his employees as it isn’t the typical move of a three-year old, growing company that has received upwards of $13M in funding.

Employees’ reactions were polar opposites and brought enough chaos to pause work production. “Some people were giving me high fives and some people were like, ‘This is fuckin’ crazy–you’re gonna destroy the company,” Carson says.

But a few halted business days and nearly one thousand thread comments later, Carson was relieved to find the majority of employees jumped on board with his quick decision. “I was actually afraid that people would say no because I thought to myself, ‘I don’t know if I want to run this company if they want the traditional management structure.'”


Inspired by the likes of Zappos and GitHub, Carson and cofounder Alan Johnson enacted the change within just a few days with hopes to figure it out along the way. “We did as much studies as we could within the week before announcing it, but the details were so obscure, we couldn’t figure it out,” Carson says. “So we had to kind of invent it from the ground up.”

Even thought Zappos CEO Tony Hsieh’s impulse decisions were not always approved by his employees, at the end of the day, the experiments–like the no-management rule–were the inspiration behind his multibillion dollar business which came from a typically mundane idea of selling shoes online.

A few months before removing management, Carson began a mandatory four-day workweek–an unheard of approach to a fast-growing company. “I was pretty naively optimistic in the beginning when I said, ‘I think we can get five days of work done in four,'” he says. “But, miraculously, people have figured it out and the amount of goodwill that is generated from that is worth a million times more than the eight hours that we could have got out of that day.”

Long term, Treehouse will have to figure out how to scale with more employees, which may bring about more as-yet-unforeseen changes. “Scaling the work structure with thousands of employees one day–I have no idea how that’s going to work,” he says. “But I’d much rather try and figure it out than die a slow corporate death.'”

Naivete Does Not Mean Mistake-Free

While it may work out well for Carson most of the time, off-the-cuff decisions don’t always produce good ideas. In fact, it can result in a big mistake–like the email he sent out last month.


Carson asked all 70,000 students to voluntarily download certain software, which came across as a prompt to install spyware, “It was a disaster,” he says. “Why in the world I thought it was okay for me to do that is beyond me.”

It was one of the few times Carson was really shaken by a naive decision he made. “Everyone in Treehouse was really angry at me and it was more painful than our students being angry at me,” he says “That was the first time I felt kind of afraid like ‘Oh, wow if I screw up again, I may permanently shake their trust.'”

After apologizing personally to customers through email and Twitter, Carson could see that people respond well to authenticity. “I got responses like, ‘No big deal, thanks for apologizing’ and ‘I like you even more for apologizing.'”

It also taught him a balanced use of cofounders’ powers. “I should have ran that by our cofounder so he could have told me, ‘Dude, that’s weird, don’t do that.’ But, I think it still needs to be balanced with being willing to pull the trigger on stuff even if someone doesn’t think it’s a good idea. But in this case, I think I just veered too far on the side of naive quickness.”

Think Like a Child

It’s Carson’s child-like outlook on life reflects Treehouse’s design and user experience with simple icons, rounded typefact and easy-to-follow video tutorials. “Learning new things really is amazing and I think especially the name Treehouse is a name that reminds people of that wondrous adventure,” he says.


“Now that I have kids, I’m reminded how serious adults get and mostly unnecessarily so,” he says. “They run around and they are smiling and laughing and life is just a big adventure,” Carson says.

Cofounder Alan Johnson says the whole idea of Treehouse started by recalling the wonder of when school used to be fun.

“In the beginning we were like, ‘Hey let’s shoot some video about web development and web design and people could watch it and learn–it’ll be fun,'” Johnson says. “I would say a lot of the risks we have taken have a lot to do with Ryan’s optimism and a lot of those risks had a big part of our success.”

Carson and team’s latest idea, Workspaces, is a built-in text editor which has set out to solve the problem of students’ inconsistent note-taking software, which they had to find and download themselves prior.

Coming up with an extremely secure, streamlined product for both students and professional developers to understand was a challenge. “We were several months into the build with multiple major design overhauls under our belt before we had a clear answer,” says Treehouse designer Matt Spiel.


After wrestling with several overall aesthetic concepts, they settled on a native desktop software. “The answer, in our minds, was to provide them with something native to the web that would allow them to follow along with the content, experiment, and create their own projects without having to worry about which operating system they were using,” Spiel says.

Students can now create and save HTML pages, JavaScript and others right from within the browser. “It turned out to be a huge technical and design challenge, and I’m extremely proud of the team for launching it,” Carson says.

Carson can add Workspaces to his resume and appropriately titled blog The Naive Optimist, where he details the thoughts behind his quick actions. But, why put it all out there for the world to see his tests and missteps?

“Because I firmly believe that nobody really knows what they are doing,” he says. “So it’s kind of a ruse to pretend that anyone has anything really figured out. I’ve sold a couple of companies so it seems to make more sense that instead of hiding my failures, I just talk about them.”

“It’s more a matter of saying, ‘Of course I don’t know what I’m doing and of course I’m naive,’ but that’s why I’m excited because reality is going to be whatever I make of it and it’s kind of fun,” he says. “I’d much rather try things and be wrong than not try them and be right all the time.”