How Gen Y Entrepreneur Ryan Paugh is Helping Forge Networking's New Path banner image

How Gen Y Entrepreneur Ryan Paugh is Helping Forge Networking's New Path

This post appears as part of our Driven profile series, spotlighting some of the hottest movers and shakers from all corners of the Boston tech and startup space. Know someone we ought to chat with? Let us know

Take a look at nearly any media site and you'll come across myriad resources about Millennials: Lists of our perceived flaws (We're lazy! A generation of participant ribbon-seeking kids who expect the same treatment in the workplace! Technology and social media have ruined our abilities to really connect!). Tips on how to work with us. Ways to get us to really engage. Why we're just one big, baffling generation with little to no promise.

But just as there's endless information highlighting exactly how much we live up to our stereotypes, so too are there Millennials whose work proves that everything you've heard is just a crock of BS. 

Take Ryan Paugh, for example. In the last decade, this Boston-based Millennial (he prefers "Gen Y") entrepreneur has co-founded not one but three tech-based companies: Brazen Technologies, Young Entrepreneur Council (YEC), and CommunityCo - all taking an online, community-focused approached to engaging and networking with ambitious young professionals (including but not limited to Millennials). Today, Paugh's YEC is leading Forbes Councils - invite-only online communities targeting elite business leaders.

I wanted to learn more about Paugh, so we recently sat down to discuss his take on Millennials, how he thinks tech is changing everything we know about work, and why communities like the kind he's creating are the new way to network. Read more in our interview below.

Kaite Rosa: Millennials are constantly thrown around right under the bus, especially by the media and corporate America. We're always called lazy, entitled, clueless on how to connect with other people.

But here you are: a Millennial, Gen Y-er - whatever we want to call you. You're defying all of those stereotypes. You're busting your ass to create a community of hardworking professionals. So what's your take on the whole Millennial, Gen Y stereotype? Is that something that you're actively working to defy?

Ryan Paugh: My first company, Brazen Technologies, started off as a social network aimed at helping Gen Y / Millennials find their path. It all sort of stemmed from a blog that myself and my freshman year roommate started after we graduated college, addressing some of the stereotypes and some of the older generations. The [Generation] X-ers and the Boomers who were talking about Gen Y and putting us in such a negative light.

My take on it is that, in business, we're very focused on generational differences. I learned that it's less about the generations, right? It's more about just the way that people are learning to work better.

KR: That’s actually where I was going to go next. What do you think makes Millennials so baffling to older generations? How do you think technology impacts that stereotype?

RP: A lot of it is around how we embrace technology. And how we embrace different types of teams, different ways of working, being able to be virtual versus all in the same place. We’ve got to just think about how we get jobs done in more meaningful ways, and break the status quo. And that's really uncomfortable for a lot of people.

I think that's where most of the complications and misconceptions kind of come from. It's just like old school way of thinking versus new school way of thinking.

I don't believe in the Millennial stereotypes. I believe in the fact that technology's changing, society's changing, our values are changing in terms of how we want to spend our time, how we work and live, and how we interact. And that's where it all comes from.

KR: You mentioned earlier how tech has made it possible to work from wherever. That’s something that’s really helping with work/life balance. You have two kids, you're married, and you're running multiple companies. Can tell me how the ability to work from anywhere has impacted you?

RP: We started CommunityCo virtually. My partner, Scott [Gerber, CEO, CommunityCo], is in New York. I was in Madison, Wisconsin, which is where I started Brazen Technologies. That wouldn't have been possible without tech and the ability to collaborate online and use all the tools available to us.

Fast forward to now. We have a team here [in Boston] of 20-plus people, but all together we have a team of 50 plus around the country in different areas. That distributed team model wouldn't work without things like Slack, the ability to collaborate using Google Drive, Dropbox. These are the things that drive our day and ability to work.

I always try to make this idea of having the freedom to work wherever you want a core idea for our company. Not just for the virtual people, but for us here in Boston as well. We do “Work From Wherever Fridays”, where the team can go and work from wherever. It's a way to allow more of that flexibility and work/life balance, so that work doesn't interfere with all the other things in your life that are truly important. And it's been great.

We've all sort of struggled with the question of whether or not people would take advantage of that, and it's not been a problem. As we grow, certainly we've had issues, but we're quick to nip them in the bud. We're all adults and good communication solves most issues in companies.

KR: Have you had any issues on the opposite end of the spectrum? Maybe people who find that level of flexibility a bit uncomfortable?

RP: Yeah. We have people who still come in on Friday because they're more comfortable being here, and would rather have the focus of being in an office versus working from home. And that's cool. Whatever they want. It's their day, they decide where they get to work.

The other thing about it that's so great is, when we're in one space for an extended period of time, that space influences your way of thinking and your way of doing things. When you go somewhere else and start working, you start thinking differently. The space that you're in influences the kind of work that you do. So it's fun to see how people work differently that one day a week and what they can accomplish then, versus what they can accomplish here [in the office] the other four days.

KR: What about you? Where are you most creative? Where do you think you do your best work?

RP: It's different now than it used to be. But I think my best execution work is stuff that I have to get done and I save for when I'm not with the team all day. Because when I'm here, my job is talking to them, working with them, helping them knock down whatever road blocks they have.

My best work is just done independently, in a coffee shop or when I go and travel somewhere with my family and find a place I've never been to. I’ll just open my laptop and get work done. The power of places is really important to me when I need to really execute on the stuff that only I can do, versus delegating - which I spend most of my time doing.

KR: Going from Brazen, to YEC, and now CommunityCo, how have the communities you've created been influenced by your own need now to bounce ideas off different entrepreneurs or - back then - different young grads?

RP: I've always been a natural connector. I get a high from connecting people, knowing that they might be able to do something great together - whether that's help each other solve a problem or start a new business.

What motivates me and inspires me about it is that in business - and anything in life - people are your most important asset. Most people don't know how to find the right individuals to connect with and aren't as naturally inclined to do what it is that I can do so well.

With all the noise out there - with Facebook, LinkedIn, Slack, all social media - it just seems so easy to connect with anyone you want to. But it's really just noise and clutter. What we try to do is make connections with the right people easier for busy people, like entrepreneurs and business executives, through curating and being really selective about the group and adding an element of trust when it comes to networking online and offline as well.

KR:  How do you think technology is influencing the evolution of networking?

RP: I think technology has been great and also incredibly evil to the evolution of networking. It's great because we can access the right people on demand from our phones, right? But at the same time, all of this excessive connecting, and posting, and networking for the sake of networking has just made us less attentive, less present for the people who really matter.

One thing that has become really important to me through YEC, and all of the other communities that we're creating, is making sure that we focus on creating experiences that allow people to be more present. Versus just jumping from connection to connection without any real meaningful substance.

KR: And in what way are you enabling those experiences?

RP: Spending a lot of time with offline events, but really meaningful ones. Not just going to a bar and drinking and collecting business cards, but taking people on a private excursion and spending a weekend going on adventures, and sharing good food and drinks, and having closed-door sessions where we talk about business challenges that will never leave that room.

It’s making an experience that allows people to let their guard down, not put on the fake online personal branding facade of how perfect their life is. But really talking about the crazy bullshit that we deal with every day, help each other solve problems, and make some of those experiences that we're going through by ourselves less lonely.

KR: How are you helping your members feel safe in that type of situation? And by safe, I mean comfortable sharing their intellectual property and their ideas without running the risk that someone else is going to take them.

RP: Some people certainly have an issue with that and it keeps them from sharing. But for the majority of our community, it just has never been a problem and I think it's because we've set the tone correctly.

I share my own business challenges with members. I like to be transparent and honest and vulnerable whenever possible, because my actions will speak to the tone of what we want this community to be. I mean, every chance I get when talking to members, I talk completely openly and honestly about the things that I struggle with.

I was talking to a member at our Boston event [recently] about going through these ebbs and flows of depression in being an entrepreneur. And it was funny. He was like, "Yeah, I've gone through that, too. Holy shit, I thought it was just me." And it makes that experience less scary and it's just so refreshing to know that other people are dealing with this and I'm not just going crazy.

KR: What's the depression in relation to? What's the situation?

RP: We were talking about the ebbs and flows of feeling like you're in a rut with your business. How that creates a sort of depression if you hit a plateau.

As you're growing your team, you find yourself being in this position where you just don't know what to do because you're growing, you're delegating, and you're just still here.

It's these moments of, “What am I doing? I feel a little bit bummed about my business right now.” We’re told as entrepreneurs, “You shouldn't be feeling that way. You should always be passionate. You should always be excited about your business, feeling hungry and ambitious.” But people go through these ebbs and flows of feeling good and not feeling good.

I think what was so refreshing about that conversation was that someone else was willing to let their guard down and talk about the fact that we're not always at our best. Even though everyone says we're supposed to be constantly hustling, constantly crushing it, all of that bullshit...

KR: Never sleeping, never eating...

RP: Exactly. So that’s the kind of experience that we try to create: The more present kind of connection that allows entrepreneurs to let their guard down, talk about problems, and just realize that they have peers. And what they're doing isn't - and shouldn't have to be - this extremely lonely feeling place.


Kaite Rosa is Director of Content & Marketing at VentureFizz. Follow her on Twitter: @KaiteRosa

Image via Ryan Paugh