Chris McCann – Startup Digest 2 of 2

“Try creating products by solving real problems.” StartupDigest is a weekly, members-only, curated guide, showcasing the best events in the startup world.

Matthew: So what was one of the hardest obstacles or challenges that you had to overcome to launch StartupDigest?

Chris: Right when we launched, we were doing great. We were adding a couple hundred, then a couple thousands users. We had our first TechCrunch article in January, 2010. So a little bit after we launched, we had a bunch of people. We originally only took $25,000. Very, very early on in the beginning and we essentially stretched it out until now.

So we were living on basically ramen and not much else. For a long time, we were kind of searching for a business model. We were still very unprofitable, and to see your tech account going lower and lower and lower and your revenues going flat and flat and flat and flat, it’s kind of . . . it’s hard.

You know at one point we were pretty close to cutting the line there. When you’re in that situation, you’ve got to keep executing. You can’t think about that sort of stuff.

In hindsight, those were one of the closer moments that a lot of entrepreneurs experience and this is startup life. Most successful founders had to live through something like that one time or another.

Matthew: In the short time frame that you have been in operation with StartupDigest, what have you learned about your business and your users or your members that you didn’t realize before you launched?

Chris: Very good question. Very early on, we didn’t even think of ourselves as a media company. So it’s only kind of in hindsight we’ve kind of figured it out. You can probably tell through the story of how we created this it wasn’t this planned thing that we thought out. It was more of a chance thing that kind of took off.

Very early on we weren’t thinking about it like a business. It kind of happened in the middle somewhere. And then you kind of had to figure out the piece, “Well, if this is a business, how does this make money? What does this look like? Who would be interested in funding it?” All that good stuff.

So one thing we realize is that we’re really creating a new kind of editorial model. We’re really empowering our own members to become the curators for that issue. So how we get all of our information is we actually have startup founders themselves, they’re the ones that pick the best events, jobs and what to read for their industry and then we do all the publishing once a week.

What the curator gets is that e-mail newsletter actually comes out in their name. So if you get the New York City one, it comes out in Carter Cleveland’s name. If you get the L.A., one it comes out in Matt Sandler’s name. So it’s really a different way of looking at publishing or media, and it’s really cool to see. A lot of our curators will contribute their funding or their partnerships or their co-founders directly to this. So to see them get an extraordinary amount of value from this on both sides and it be good for the users, it’s kind of cool to see it in hindsight, and it’s a different way of looking at media that we would never have realized in the beginning.

Matthew: And so who’s been a mentor to you in your professional development? Then who’s been a mentor or played a significant impact in launching StartupDigest? That’s two questions.

Chris: Good question. Currently people who help me is kind of people who help the company, so it’s kind of one and the same. So I’ll say for the personal one I’ll talk about people before that.

A lot of it came from Cal Poly where I went to college. There were two guys in particular. One is named Carson Chen. He was one of the very early guys at Cisco, and he developed this program called Innovation Quest. It was this engineering competition at Cal Poly. Super, super successful guy, and when I was very naive and didn’t know anything, he was really kind of coaching me through stuff. We put this program together, and we were looking at the college theses and picking innovation and all the good stuff. Just to kind of hear his feedback and insights on all of this is just so, so valuable.

This other guy who I don’t talk about a lot, actually, is a guy named Bob Biddinger. He was one of the co-founders of Seagate who happened to live in San Luis Obispo of all places in the entire world because he was done with his career and he wanted to relax. The guy’s like 80, but he looks like 50. He’s like fit. He’s, like buff. But he’s really, really into more personal development stuff. So this is when I was going to school for motivation and for keeping myself energetic, even diet stuff and all this stuff, he was super helpful for me.

I guess to go quickly into more the business stuff, especially when I was launching StartupDigest, I guess one guy in particular I’ll just talk about, Dave McClure, founder of 500 Startups now. I organized the Geeks on a Plane Tokyo trip. That was actually the first time . . . I kind of met Dave through a lot of events and stuff like that, but when you crash in a hotel room with a guy for eight days, you kind of tend to get to know him. To see all the things he was working on, like the international view that he took on tech startups, the way he was thinking about investing through 500 Startups, and just kind of the world view that he had, it really helped us in the beginning, and that’s probably one of the big reason why we’re in all these different cities. If it wasn’t for him and a lot of other things, we probably would’ve been just a small little Silicon Valley thing. But now a lot of our value and benefit is because we’re in all these other places, and he really helped us out in the beginning.

Matthew: What piece of advice would you want to give to people in our audience about starting something? What do you think the key elements are?

Chris: Find something you’re very uniquely passionate about, some very personal problem of yours. If you look at a lot of successful companies, you usually find some deep-rooted reason why they’re doing it. For me, it was very apparent, I moved here, I was very new. This was why I made this. If you look at our company, you’ll see that same story play along, different industries. It doesn’t even have to be tech, just even general entrepreneurship sort of stuff.

You know if you’re in college or maybe in a corporation or maybe thinking about something, think about what are your problems, like what am I really interested in tackling and helping other people? How can I make something to solve that problem as simple and fast as possible? A lot of people call that an MVP. For us, our minimal viable product, that’s what MVP stands for, was that first e-mail to 22 people. It was a very super simple thing.

Just try and create things and solve that problem and see if it works. Your first 20, 30, 40, 50 will probably fail, just like mine did. But just keep going at it and keep trying different things, and one day you’ll find that thing that feels right.

Matthew: Excellent. So before we close, we’d like to get your vision for StartupDigest and how you hope it’ll change the world.

Chris: Yeah, very good question. For StartupDigest, specifically we’re looking at it like no matter where you are in the entrepreneur ecosystem, whether you’re just beginning, you have something, you’re in the hiring mode, you’ve already sold your company, wherever you are, wherever in the chain you are, we want to be able to provide you the information for this industry.

Information for us is events, jobs, and what to read. So we’re not producing our own news or analysis or editorial. We’re really just curating and scraping through all this information and giving you the highest value stuff once a week.

We really want to bring people together through this information and allow people to find jobs, connect in person, find that one thing that’s really going to educate them and help them build their business, whether it’s hiring or fundraising or whatever. But it’s really pulling together this industry on a very international scale.

We’re already in 60 cities, and we’re probably adding more soon. So we’re really pulling together this whole vertical that we call tech startups into one publication.

Matthew: Excellent. Well, Chris, it’s been a pleasure having you as a guest. We’re rooting for your success at StartupDigest. We hope you’ll come back as a guest. Again, thanks for being here. This is Matthew Wise with If you would like to learn more about StartupDigest and subscribe to become a free member, you can visit them at Thank you.

Chris: Cool, thanks.


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