Today’s jobtalk is with Ryan Healy, one of the co-founders of Brazen Careerist, and the only founder who still works for the company. After my interview with Penelope Trunk, I realized that it’d be great to hear from one of the other founders of Brazen Careerist, so that’s when I emailed Ryan Healy.
As a newbie in the blogosphere, I automatically assume the worst when I contact someone who doesn’t know me – I won’t hear back. So it made my day when Ryan Healy responded to my request for an interview saying that he’d be happy to do it. As the epitome of Gen Y’s resourceful and hardworking, Healy not only serves as a role model for his generation, but also for anyone who has an entrepreneurial spirit.
B.S. Accounting, Penn state University, 2006
Healy’s been named as one of the Top 20 Entrepreneurs to Watch by Worth magazine. But I assure you, it hasn’t gone to his head.
Did you start college knowing that you wanted to be an entrepreneur?
I was always really interested in business, but I didn’t put together that I wanted to start something on my own and create things from scratch until my sophomore year in college. A buddy of mine who started a business in college took me under his wing.
What was the business?
It was on online ordering business. You would order takeout online. It started at Penn State. My friend ended up bringing it to different schools. He left, but it got pretty big.
When you graduated from college, what made you take a job at IBM?
When I got nervous about majoring in entrepreneurship – I had created a major in entrepreneurship – I switched to studying accounting. And once you’re in accounting, you end up going to work at a big accounting or consulting firm. I got lost in the shuffle, I like to say. I ended up following the crowd. I figured that I didn’t know what else I was going to do so it seemed okay.
It doesn’t seem like you followed the crowd for very long.
Well, that’s the thing, I realized quickly that I couldn’t crack it.
What was it that made you realize that?
I need to have an impact on whatever I’m working on. I guess maybe I need some control – or a lot of control. And I need to be doing something that I really believe in that makes a change in some way; I need to be creative and do something that’s helpful to people.
What you’re saying is something similar to what I’ve heard other entrepreneurs say.
Right. I could have done that at IBM, I guess, if I wanted to wait 30 years.
What inspired you to start your blog, Employee Evolution?
I was helping out my boss at IBM do some recruiting at Penn State. I talked with folks from IBM and with my father a lot about this new generation – my generation – that was coming into the workforce. People were saying that Generation Y was so different, that kids these days are lazy and entitled and want trophies. I remember hearing about all this and I thought it was really interesting because I just didn’t see it. It wasn’t what I saw from myself or my peers.
So I did some research. And the thing that I realized was that there were a ton of people who were making a great living off of telling companies how bad young people were and how much they needed trophies and all that stuff.
I didn’t think it was true. And I realized that all these people who were doing it were in their 50s and 60s. I thought, “What do they know about this generation? I don’t think they know what they’re talking about it.”
I had the idea to talk about Generation Y in the workplace from the Gen Y point-of-view. I figured that the best way to talk about it was to start a blog, but I knew nothing about blogging. I reached out to a friend of mine, Ryan Paugh, because he had majored in journalism. I figured he would know what a blog was.
He was working at Merck at the time. He said that he had heard some of the same ideas about Generation Y from consultants that came to Merck, and he thought what they were saying about people our age wasn’t true either. So we decided to start the blog together. We wrote about Gen Y in the workforce from a Gen Y point-of-view and invited our peers to write about it too.
About a month or two into blogging, we started getting calls from press. The Wall Street Journal called Ryan one day. The next day I got a call from Business Week. Then the New York Times called. We had become to go-to sources for anyone writing about Gen Y at work because the other sources were in their 50s and 60s. It was crazy and totally unexpected.
As we were growing, I really wanted to turn the blog into something. I thought, “Well maybe this will turn into something.” I reached out to Penelope and asked for feedback on my writing. She wrote back and she asked me to guest post on her blog, which drew more attention to our blog. I’d write one post a week for her blog. She’d edit it and then we’d talk about the post on the phone.
At the same time, Ryan and I were trying to figure out how to make what we were doing into a business.
Penelope said that she was thinking about doing a startup having to do with Gen Y in the workplace too, so we all decided that we should do it together. That was in 2007.
After that, I put in my two weeks’ notice, we incorporated and moved out to Madison Wisconsin.
At that point, you had no doubts, you just went for it?
Exactly. I knew it was the best shot I was going to get.
What was that first year in Madison like for you?
It was weird. I think that’s the best way to describe it. It was Ryan and I living on the top floor of a house that we rented for 500 bucks a month. We lived on maybe 1000 bucks a month tops. An awesome family friend of mine gave us 25K – no strings attached – that we lived off of.
We just tried to figure out what we were going to do. We worked from the apartment that we lived in. It was fun and weird and exciting and cold.
What was that figuring out process like?
Penelope would come over to our apartment and we’d get out a whiteboard and throw around ideas. When we settled on where we were going to start, we worked on figuring out how to find people to help us build our project.
How did you find people to help you?
At first we found people who would help us in exchange for equity or who would help us for a low cost. We had a designer who was a friend of Penelope’s who we paid a little bit. And we had a software developer who was Ryan’s and my friend and we paid him a little bit. Once we got a prototype off the ground in March 2008, we got really lucky and were able to raise 700K.
Then we were able to hire the software developer full-time and convince him to move from Philadelphia to Madison, Wisconsin.
In late 2009, we had another investor come on board. We asked him to be the CEO. We wanted somebody to come on and act as CEO because we thought we needed someone with an entrepreneurial background.
I think it takes people who are really humble to do that.
I think you’re right. It does to a point. Penelope was the CEO at that time. It was good to have somebody be in between Penelope and me too. We both have strong personalities.
Do you have much of a personal life?
Yeah, I do. My girlfriend moved out from Madison to D.C. with me. We have a lot of fun. I work a lot. But we also play a lot. I’m finally going to take a little bit of time off this year to travel. I’ve got a pretty good balance.
What’s your take on Tim Ferris?
I think he’s one of the top 5 marketers I’ve ever encountered. He’s really good at knowing what people want.
What are your day-to-day responsibilities as a COO?
It’s everything and anything, and it changes every day. I do everything from doing fundraising to finances to wire-framing new products to coming up with a sales strategy for how we should be selling into companies.
If you could talk to your 20-year old self, what would you say to him?
There’s so much. I’d say to be patient. Everything is going to take 3 times as long as you think it’s going to take. But you also have to be persistent because if you sit around and wait for something to happen nothing is going to happen.
The other thing I would say is to figure out how to just ship it. Meaning, get the product, the service, whatever it is, out there. See how people react and then make decisions about where to go.
That’s what Eric Ries talks about.
Yup. Exactly. I’m a big believe in The Lean Startup.
What is your favorite late night snack?