We hosted a webcast conversation between Jensen Harris and Elliot Susel focused on taking the leap from a big company to launching a startup and the differences between those two company cultures.

Don’t have time for the full webcast now? Catch the webcast highlights and tips from their conversation in our companion blog below.

If you’d like to read the full transcript of Elliot Susel’s conversation with Jensen Harris, you may download it.

Making the Leap from Big Company to Small Startup

In 2014, Jensen Harris had a conversation with Kieran Snyder about their mutual dissatisfaction with writing software. “Here we are, 40 years into the post typewriter era, and still, all the software [we have] to write [does] the same thing a typewriter did,” he says. So, sixteen years into his career at Microsoft, Jensen Harris decided it was time to set out and try something new: launch his own startup. “Although I loved much of what I was doing. … I felt like it was time to make a change,” he says.

So Jensen and Kieran decided to go for it. They quit their big corporate jobs and set out to raise seed money for Textio — augmented writing software that uncovers meaningful patterns in language to help you know how your words are going to work and guides you to stronger communication in your writing. “It’s the biggest advance in writing since the computer,” Jensen says.

Now several years into their venture, Textio co-founder and CTO Jensen Harris spoke with Lean Startup Co. faculty member Elliot Susel about the differences between working for big companies and startups and taking chances to further your career.

Building Things the Right Way

Jensen admits that making the transition from working at a big corporation with great compensation to a small startup isn’t easy. It certainly wasn’t for him, especially since he and Kieran made the decision to leave their day jobs to completely focus on building their product.  “We watched our … bank accounts dwindle into a dangerous place,” he says. But, because Jensen and Kieran knew the product they wanted to build couldn’t be done justice at a big company, they figured out a period of time where they could make things work so they could create the best possible version of their product. “A big disadvantage that large companies have is that they already have a user base of hundreds of millions … with legacy code, legacy expectations, and features you can’t ever get rid of … so, keeping these users happy is very hard.”

So Jensen and Kieran started methodically building Textio and gathering — not just finding — data from potential customers to help them build a product that could actually power their business. From very early on, it was important to them to not only build a working product, but also perfecting elements of the user experience so they could measure the viability of Textio as a whole. Jensen likens it to building a little bit of the engine and a little bit of the frame of the car at the same time.

“[Overbuilding something] is a classic mistake that people who come from a big company [make],” Jensen points out, themselves included. “There were some places…where we built things out early that [we said] ‘man, I wish we could have those weeks and months back.’” But, he says it’s something you learn from, and you try to get better and better.

Ultimately, understanding the kind of product you have may rest on how people feel when they use it. “Actually building that holistic and emotional experience into the product sometimes takes a little bit of extra polish on the front end and the place where you can wait a little bit is sometimes on the backend. … Understanding that, I think, is key.”

The Freedom to Fail and Other Startup Advantages

Deciding to go the startup route was a risk, but one that Jensen was happy to take. Because when it comes to your career, Jensen is a big believer that every person should work at a big company, a medium-sized company and at a startup. “The best career path for almost everyone is going to be to try all of those things.”

And there are plenty of good reasons to take the leap to launching or working for a startup: you get to see a company built from the ground up, you’ll see how the work you do plays into the success of a company, and you’ll have an unparalleled ability to try new roles and take on leadership opportunities that you’d never have at a big company.

And there are less obvious advantages to moving to a startup that people don’t normally consider. Like, having the freedom to fail.

“In a big company, failure is often punished,” Jensen points out. Whereas at a startup, failure is part of the process and it happens a lot. But instead of being a negative thing, it’s perceived as an opportunity to learn something, to fix it, and to ultimately make it better.

Because “failure” is such a big element in any startup, it also gives you an excellent opportunity to learn from everyone in the company including the people at the very top. And part of the learning process gives you the freedom to ask any and all types of questions. “There are no dumb questions,” Jensen says, “we’ve all heard it a million times. It really has to be true in a startup.”

What’s more, the collaborative and loosely structured environment generates a culture where everyone has a helping mindset. “You’re not competing with your coworkers for a promotion,” Jensen points out, “you’re building something with them in a way that’s deeply collaborative and incredibly important.”

Don’t Just Work for Any Startup

That’s not to say that every startup is a startup worth working for. “All startups are not created equal,” Jensen warns, “you have to choose the right one, ask the right questions, and look for the signs that are successful.”

Jensen points out some warning signs to look out for:

• Vague answers. Great places to work are going to have clear answers about what they’re working on, what their product does, what their vision is and what their culture is like.
• People aren’t forthcoming. One of the things Jensen counsels people to ask in an interview is, “tell me about a time the founders disagreed.” How the question is answered — or not answered — can tell you a lot about the founders, the employees, and the company.
• No discernible changes. Jensen also recommends asking people how their work environment has changed in the last year. Any startup that’s on a successful path is going to have immense changes. “Everything’s growing, things are changing, everyone’s learning, you’re figuring out new things,” he points out, “it may mean that the company is on its way out, but at the very least it means that the employees aren’t as engaged as you may want.”
• Lack of employee engagement. Any employee at a startup should not only be able to tell you why a place is special, but their answer should come from a place of more than them just doing their job, it should come from a sense of pride and belonging within the company.
• Ego. Ego is kryptonite for a company. The best people can not only find the right idea or answer to a problem, but they’re also willing to let it go. “In the end,” Jensen says, “it doesn’t matter who comes up with the idea, it only matters that you find the best idea.”

But when you do find the right startup to work for, Jensen thinks you should go for it because it’s like rocket fuel for your career. “It is life affirming. … You can compress 10 years of what you would have to do in a big company [to advance your career] down to two years in a startup. Man, if you can do it, you should.”

And if working for a startup doesn’t work out? “The big company job [will always] be there.” The Googles, Microsofts, and Facebooks of the world will always have a need for people. And, if you do decide to go back, “you’re probably going to get a bump up because of the experience you’ve had outside.”

Thanks to Shannon Lorenzen for contributing this piece. If you seek to bring the entrepreneurial spirit to your organization, Lean Startup Co. can help.