Why People Make The Crazy Choice To Go From Megacorp To Startup
“I didn’t know what it meant to be an entrepreneur,” says Walter Chen, founder of IDoneThis., “I guess if you go to Stanford, everyone starts their own thing, but that wasn’t a normal part of my experience. I just wanted to do something different. I wanted to do something more creative and expressive.”
Lately, the air is thick with startup mythos and the streets are paved with convertible notes, so it might seem easy to leave a steady job for a startup. But it’s still a big decision with lifelong implications.
So why do it? For some people, startups are a great way to find their voice, be creative, and feel like they’re making an impact. Of course, there are plenty of stereotypes about startups — but there’s truth behind the stereotypes. Here are the in-depth reasons that Quibb members described when we asked why they dropped out of Big Companyland and moved to Startupland.
#1. The Chance To Be Creative
Walter Chen had a strong desire to express himself, which was not being satisfied when he worked at a big law firm in New York. “It was fine. It was totally fine,” he says, “but there was a desire to build and create something. In a law firm you’re arguing on behalf of large corporations, whereas when you start your own company, you can speak in your own voice.”
A lot of other startup founders described similar feelings — and employees, too. For many people, the transition is all about the opportunity to do creative and concrete work, even if they aren’t building their own thing.
#2. It’s Really Hard
Early in his career — back in the 1990s — Frankie Loscavio started an ecommerce business for skating equipment. Loscavio was a professional skater himself, so he was well qualified to address that audience, but there weren’t yet any guidelines for building an Internet store. His small business came up in the same era as larger ones like eBay and Amazon.
“I think I underestimated how hard it was, because there’s no guide or map to a successful startup,” says Loscavio today. “I expected a guide or a pattern. I wanted ‘how to be a startup owner in 24 hours,’ but that doesn’t exist. It takes so much hard work and so much thought.”
It can be quite painful at first to adapt to the startup mentality. But you have to understand that it won’t be easy. Once you know it’s going to be really hard, you’ll be okay.
Ultimately, Loscavio thrived on the difficulty. His first business went under, yet his hard work paid off because it was visible to the next person who hired him. “My first startup tried to do too much too fast,” he says. “We undercut our bread and butter revenue by quickly jumping into the manufacturing business. We ultimately diluted our time and money so much that we lost focus of the core competency that our e-commerce business had thrived on, and thus we inevitably went out of business. But my next employer was AT&T — my recruiter had been an investor at my company, and he knew directly all the work it had taken me to build my startup, and that’s why he recommended me.”
Walter Chen of IDoneThis remembers being impressed by startup founders, because it sounded so difficult. “When I was a lawyer, I was doing my summer internship, and I was sitting next to this associate, and I asked him what he did,” says Chen. “He told me he was an entrepreneur and talked about how he was raising money from investors, and I was so impressed. He was my age, and I couldn’t imagine doing that at the time.”
#3. A Real Chance For Impact
Even though Frankie Loscavio enjoyed his work at AT&T, he eventually went back to startups, and is currently working for MedTech Exchange to innovate cost-cutting solutions for the health industry. “Aside from my first company, I’ve been part of three other startups,” he says. “After a while, you start to realize you have more potential, more influence, and more ability to make things happen if you’re not just a cog in a machine.”
Gilad Bonjack used to work at a publicly-traded company of 3,500 people, in a 300-person division. He left that company to help with product at Voxer, a messaging startup of 30 people.
“When I joined Voxer it was one of the top rated apps. I was fascinated by the pace of growth, and I saw how small the company was. I knew that I would be able to make an impact.”
#4. A More Direct Connection With Users
The competitive advantage of a smaller business is better service — which means that a startup founder has both the responsibility and the opportunity to stay closely in touch with their customers. “As a business owner you have so much ability to undercut these bigger businesses by providing better quality service,” says Frankie Loscavio. “But you can only do that if you really care about the user.”
Paul Graham, who started the high-profile startup accelerator Y Combinator, often tells founders to Make Something People Want. It seems like an obvious maxim! But sadly, due to the vagaries of the scaling and governance process, it seems easy for large companies to lose track of their users. A lot of people who shifted from big companies to startups expressed empathy for this — but they also felt very frustrated about it.
#5. Much Less Bogged Down
Michael Rosengarten has done lots of startup stuff, and he spent a few years at Yahoo between startups. “It’s kind of interesting how I got to Yahoo, because it prefaces why it was easy but not easy to leave,” he says.
Rosengarten explains: “While I was at one of my startups, someone from Yahoo reached out and said that they wanted me to be part of a 4-person team that ran around Yahoo and caused a bunch of problems. They said, ‘We don’t really care what you do, cause fires and make money.’ We did exceptionally well and made a bunch of money for Yahoo, but we started to feel more constricted over time. We were building tools that would make Yahoo’s tools more successful, but the bureaucracy stopped successful products from being successful.”
Pretty much everyone who’s gone from a big company to a startup agrees: It’s amazing to work in an environment with so much less process. Francois Mathieu went from working at a bank to a marketing software startup called Uberflip. He says, “I knew how things were supposed to work after reading every single startup blog, so I was not surprised when I arrived, but I was still happy to see it was how things worked for real. At the bank, when I had an idea, I would tell everyone at a meeting the next week. If we all agreed, we had a project for the next quarter. But at a startup, you send a message on Slack or go visit the person, and you get started the same day.”
#6. The People Are Smart And Passionate
“People matter to me,” says Michael Rosengarten. “I liked my colleagues at Yahoo, and I thought they were smart and interesting, but my biggest gripe was that I was surrounded by people who… well, 9–5 was not an important part of their day. In retrospect, I realize that it was unreasonable for me to expect that from my colleagues at Yahoo. But for me, 9–5 is just as important as the rest of my day.”
A while back, while commenting on Quibb about the value of joining a startup, he noted:
“I tend to look at the people I will work with, the flexibility of the role, the growth opportunity for personal development, and a handful of other things (off the top of mind). I’ve never been one to join a startup for financial gain. Maybe that’s why the startup adventures I have had have been successful though, both financially and educationally.”
Erin Glenn moved from multinational companies like Morgan Stanley, to video game startup Kixeye. Now she’s CEO of a young startup — Quire, an equity crowdfunding platform. “I learned at lot at Morgan Stanley,” she says, “the people were smart and the pace demanding. But I loved working at Kixeye and building something from the early days. I love being surrounded by people who are as passionate and committed as I am. There’s such an irreplaceable, invaluable joy and purity in working with people who bring this energy to the job, versus seeing it as a means to an end.”
#7. They Watched The Social Network
Okay, this isn’t the best reason to join a startup, but it’s not the worst, right?
“You often go into things for the wrong reasons,” acknowledges Walter Chen. “I heard a lot of dramatic things about being a lawyer, and my reasons for going into that career were terrible. So maybe I also got into startups because it sounded cool. And the other day I talked to a Thiel fellow who got started after watching The Social Network, which is also a terrible reason.”
But Seriously: Figure Out What’s Best For You
“I didn’t put that much thought into what I was doing,” says Walter Chen. “And taking the leap is glorified. But when other people make the transition, I encourage them to put more thought into it than I did.
I was kinda like, ‘I’m sick of my job and pretty sure I’m gonna get rich,’ and it worked out okay for me, but I see people all the time who make smarter decisions about that transition. For example, some people work on their startup part-time while they’re still at their previous company. There is a leap of faith, but it should be a logical decision, too.”
It’s cliché, but true — not every company is right for everyone. And startups are definitely not for everyone. Yet finding the right fit can be powerful and energizing. “I remember talking with a Jesuit and asking why he became a priest,” says Erin Glenn. “He said it was like deciding to marry — he just knew he had to take a chance. And startups are like that, too.”
“We don’t spend a lot of time helping people, particularly young people, think about what work excites them and reinforces their values. My advice is to think long and hard about what’s important to you, what kind of workplace energizes you, and then organize your personal and professional life to make those things a reality.
“For me, when I joined a startup, I finally felt comfortable in my work environment — even though it took some time to adapt to the policy-free, just-get-it-done workplace,” Glenn concludes. “Joining a startup was like coming home.”
Find other stories about professional experiences like these by joining Quibb.
You can follow all these people to see what they’re reading for the jobs they are so passionate about. In alphabetical order, here they are: Gilad Bonjack, and Walter Chen, and Erin Glenn, and Frankie Loscavio, and Francois Mathieu, and Michael Rosengarten.
Thanks to Lydia Laurenson, writer and media strategist, for her work on this series.
