Straight out of College with a degree in entrepreneurship from Cal Poly, San Luis Obispo. Chris decided it was time to move on, quickly relocating to silicon valley.
In a new city with no family and few friends, he started attending startup events as a way to connect with like-minded people and make friend. In no-time, he was networking with some of silicon valley’s finest, after spending a lot of time going to events, with also limited time after getting a job, in order to avoid wasting time on un-important events, he decided to write down the best events that he wanted to attend once a week, his friends became interested in the list which he later started sharing via email with 22 of them in November 2009, this marked the start of Startup Digest.
This private email chain has grown into over 200,000 weekly newsletter with subscribers from over 60 cities around the world.
This is his story.
Hi Chris, Can you give the readers some background information about yourself?
Ya my name is Chris McCann and I am one of the co-founders of StartupDigest.
So how the Startup Digest idea start? What were you doing before you started Startup Digest?
I’ll lump both of these questions into one, will make it flow nicer 
I graduated from a small engineering centric school called Cal Poly San Luis Obispo, which is located in the Central Coast of California. During college I was running an engineering competition, a business plan competition, and started an alumni led incubator for Cal Poly. Although I was doing all these activities the entire county of San Luis Obispo is ~35,000 so I was basically a small fish in a small pond.
When I graduated from University, I threw all my stuff in my car and drove up to Palo Alto, Silicon Valley with the intention of figuring it out. I have no family and very few friends living in the area so I started going to events to meet people socially, get connected, & I didn’t have a lot of friends and all startup events because that’s what I am interested in
One of the big problems of Silicon Valley and a lot of other major cities is there are a lot of startup activities going on, but its very hard to know what’s good and what’s not. There are things like eventbrite, meetup, plancast, etc but all of these are comprehensive calendars, they don’t tell you what is actually good this week. So I started compiling the best events for myself that I wanted to attend once a week. After doing this for awhile some of my friends at work (I got a real job at first) thought this was cool and wanted to see them as well. So in November 2009, I sent one email to 22 of my friends with the best events going on in Silicon Valley this week, that was how StartupDigest got started.
How did you go about marketing the service? Everyone seems to know about it?
Originally since I was compiling these events for myself, I was actually attending most of the events I was featuring. Because I was featuring the events most of the event organizers let me get up on stage for a minute and share what StartupDigest was about.
Soon after one of my good friends Carter Cleveland, founder of art.sy, moved back to New York City and wanted to start an edition of StartupDigest for NYC. This is when we came up with the curator model of other founders themselves “curating” (picking) the best events 1x a week, and then we would do all of the publishing.
Fast forward to today, now StartupDigest is covering 60+ cities with presence is most of the major tech hubs around the world. Still however most of this growth is largely due to worth of mouth, and people sharing it because it solves a personal problem of theirs and it’s valuable information that’s hard to find in other places
From your experience going to different events, what makes a good event?
We define “high-value events” to be ones that get entrepreneurs working together or around a niche topic. Some examples include user groups, hacktons, Startup Weekends, educational based events, events around specific topics (health-tech, mobile, etc), and demo events. The conter-example to this is a “inspirational event” or “celebration event” which doesn’t actively get real entrepreneurs working and solving problems together.
How do you pick your curators? What is the process?
We look for others who are startup founders themselves or investors who are working on interesting problems. A great example is Matt Sandler the Los Angeles curator who started the company Chromatik, a music education startup in the LA area.
How many subscribers do you have at the moment?
A little over 200,000
Why do you think your company has become so successful so fast?
It’s simple, valuable, and solves a real problem. If I asked you what are the best events for tech entrepreneurs in Tel Aviv, where would you look?
Yeah i get it, Sourcing the best events all around the world.
What companies do you guys look up to for inspiration and why?
We’re very media focused and look up to a lot of larger media companies in our space. Some of these aren’t the most talked about companies but we take a lot of inspiration from them.
O’Reilly Media – They have built an incredible book line, conference line, and education brand around specific development topics
IDG (publishers of Mac World, PC World, etc) – Nobody ever talks about these guys but they are doing $3B+ in revenue per year. As a media company in todays environment that is insane.
Help A Reporter Out (HARO) – Peter Shankman is a friend of mine and built up a profitable email newsletter for reporters and sold it for a “reported” ~$20M
How has the business evolved from when it started? What are some of the things that have changed?
We’re constantly changing all of the time. Two of the new things we have added recently are the StartupDigest Jobs editions http://eepurl.com/daCBc and the StartupDigest Reading List http://eepurl.com/dcEHs
What would you say was the most difficult stage when you initially started and how did you deal with it?
Not being profitable and burning money slowly every single month. It’s completely nerve racking as a founder, but the only thing to do is keep on building and surviving.
What has been your most memorable moment so far?
I flew to Dubai (when we were broke) to attend the Global Entrepreneurship Congress put on by the Global Entrepreneurship Week. It was here that I met the team at the Kauffman Foundation who ended up funding us > http://techcrunch.com/2011/03/09/startupdigest-funding/
What are your revenue models?
Running advertising campaigns and we operate a job board > www.nextdigest.com/jobs
What should users of Startup Digest be expecting from you guys in the future?
We’ll be creating more newsletters to solve specific problems (keeping up with the news, finding individuals to hire) and expanding slowly outside of the pure startup tech market.
