How StartupDigest Got 100k Email Subscribers in One Year

Getting average internet users to give up their email addresses is easy. You just offer a free ring tone or Brintney Spears computer wallpaper and they hand over their addresses.

With tech founders, on the other hand, you have to earn every ounce of trust and work hard for every single email. Which is why I think it’s so impressive that StartupDigest, an upstart that’s been around for about a year, managed to grow its email list to 100,000 subscriptions.

I invited Chris McCann to teach how his company did it.

Chris McCann

Chris McCann


Chris McCann is the co-founder of StartupDigest, an email newsletter that features news and events for startups.



Full Interview Transcript

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Here’s your program.

Andrew: Hey, everyone. It’s Andrew Warner. I am the founder of, home of the ambitious upstart. How do you build a large e-mail newsletter company? Joining me is Chris McCann, co-founder of StartupDigest, a newsletter about events and news in the startup world. And Chris has a big announcement that he’s going to be making here for the very first time. He’s hit a major milestone. He’s going to tell you for the first time.

Chris, what’s the major milestone?

Chris: We passed the 100,000 subscribers last week.

Andrew: 100,000 subscribers, all of them are who? Who’s subscribed to your newsletter?

Chris: All of them are hackers, founders, CEOs of tech startups, VCs, angel investors, people generally in the tech ecosystem, tech startup ecosystem and then people kind of on the fringes that are interested in this sort of information.

Andrew: Getting 100,000 e-mail addresses is so hard. I don’t even know how to communicate the difficulty of it to the audience. I mean, most people are thinking about how do they get another hit to their website, but getting a hit is no kind of engagement compared to getting someone to give you their e-mail address.

In fact, before I say it, instead of me saying it, why, why is getting someone on your e-mail newsletter so important and so powerful?

Chris: Yeah. The big difference between an e-mail newsletter or a blog or a website or a paper or anything is you’re literally getting . . . our newsletter comes out once a week, so when you sign up you’re getting an e-mail from us every single week. You’re not only signing up to see the site for once and then leave, you’re signing almost like a customer, a real subscriber of what we do.

So you like us enough to give us permission to basically go into your inbox once a week, this private space you have, and most people, especially in the tech world, they have too much e-mail. Like, they make their e-mails really short, so for them to give us their e-mail address is a very, very high bar that we have.

Andrew: A very high bar. Like you said, people in the startup world, in the tech space are so jaded. They’re so reluctant to engage in anything. If you want to get mom and pop, middle America they’ll give you their e-mail addresses. They’ll give their e-mail address to an obvious virus, but people in the tech space, man, it’s hard. It’s hard. It’s a very significant barrier that you’ve got, and it’s kind of like being married to someone. They’re sticking with you day in and day out, even when you suck some days and, of course, when you do well most days.

What are they getting? I kind of described it, but well, because it’s that difficult and because you got so many people to do it, to give you their e-mail address and join their mailing list, I invited you here to find out your story of how you built the business, how you got so many e-mail addresses and more importantly to my audience who’s sitting there and saying, “I don’t really give a rat’s ass about Chris, I care about my life. I care about my business, more importantly,” you and I have talked, and you put together a list of techniques that people in my audience can use to grow their e-mail business. And so, that’s what we’re going to be talking about here, but give us a clear understanding of what’s in the e-mail that people are signing up for? What are they getting every week?

Chris: Now, we call the StartupDigest as kind of the insider’s guide to the tech startup world. Once a week we send you the best events, jobs, or on Fridays now we do this thing called the Reading List. The events and jobs are all broken up by area. We’re sending you the highest value tech startup centric events in your local city.

If you’re subscribed in Paris or in Tokyo or New York City or Seattle or Silicon Valley, these are all things that are very relevant to you or where people of like minds are hanging out. Jobs, same thing. Take out the events, put in jobs, and this Reading List is kind of a collection of the best articles for that week for the industry. But it’s all around, like I said, the tech startup ecosystem and it’s all through e-mail newsletters.

Andrew: Okay. For you to be able to put this together in all these different cities, you can’t do it yourself. You came up with a clever solution that, man, ever since I heard about it, I just said, “I should have done it myself.” It’s such a freaking clever idea. Who are these people who are putting it together for you?

Chris: You might be thinking to yourself, okay, you have a startup guy who is in Paris. How the hell do you know what’s going on?

Andrew: Yeah, what’s does Chris know about startups in Paris?

Chris: I don’t know anything. So the approach we took was . . . at the beginning it’s not like we have a ton of money. We couldn’t pay for a huge editorial support staff to go out and compile this for us. So what we looked for, we found tech startup founders themselves living in their area. They’re the ones that pick the best events, and they basically send us the basic text of the event they want to feature, and then we do all the publishing of it.

It started because one of my good friends, Carter Cleveland, me and him were friends here in Silicon Valley. He moved back to New York City. He saw what we were doing. This was just when we were in one city, and he was like, “Hey, this is really cool. I want to do this in New York City.” And I said, “Cool. How is this going to look?”

Me and him kind of came up with this curator model that we call “Now”. The main benefit for the curator is the e-mail newsletter actually comes out in their name. It has a direct tie-in benefit to them. It’s actually published out in their name.

Andrew: Ah, see, I’ve been wondering about that. How do you get all these great guys to be your curators and essentially do the work for you, especially when we already read Tom Sawyer. We know that other people are going to try to get us to paint their fences for us. All right. You are giving them a lot of attention. Who are some of the curators? I know the audience is saying, “Forget about him. Get back to how we can learn to build our newsletter.” But I’ve got to hear from you. Who are some of those?

Chris: Like I said, most of them are all tech founders, investors.

Andrew: Name drop, exactly. Name some of the investors.

Chris: Some examples, like I mentioned, Carter Cleveland. He’s in New York City. He started a company called We have another guy, Josh Baer. He’s in Austin. He’s the founder of Capital Factory and also Other Inbox. He’s kind of an investor and entrepreneur at the same time.

In Detroit, there are two guys, Raji and Jeff. They’re both startup founders in the Detroit area. In Paris, there’s a guy, Pascal. I think he’s doing Card.Biz, that’s trying to place business cards out in Paris. Those are just some examples. Like I said, they’re all generally tech founders living in that city.

Andrew: And the revenue’s coming from where?

Chris: The revenue, how we make money, is two fold. It’s advertising and commerce, The events, jobs is really kind of our content. It’s our editorial. We don’t mess with it. We don’t screw with it. You can’t pay to be in there. You can’t do anything. But on top of that, we include one little short blurb, short little textual message. And it’s either a paid for advertisement or it’s e-Commerce with a flash sale.

We were looking at all the other e-mail newsletters, the successful ones, some you’ve actually interviewed, Thrillist, Help a Reporter Out, Daily Candy. Essentially we’ve copied a lot of their models and applied it to what we’re doing.

Andrew: What’s the e-Commerce part? What are you guys selling?

Chris: It’s generally products that would excite our audience. Two examples of that, one we did with user testing. You can have someone actually use your app or use your site or service, give a video, give some feedback. Normally, to have three people look at your site it’s eighty bucks. We got a 50 percent off. We took 50 percent of the revenue, and it’s a limited quantity for a limited period of time.

Andrew: I see.

Chris: It’s called a flash sale. It’s like Guilt Groupe or Boys Purvey or some of them do. It could be a digital or it could be a physical product. Another example that we did was on Monday we did on Manpacks, which is an awesome, awesome product. It’s underwear, socks, t-shirts subscription, awesome.

Andrew: I’m subscribed actually. I think my next pack is coming any day now. So, you get a cut of that. You sell it on their behalf. You make a cut of the revenue that comes from it, and they hopefully get a subscriber that stays with them for a long time and continues to make money for them.

Chris: Exactly.

Andrew: Okay. It’s not that you’re selling your own stuff. It’s kind of a CPA deal essentially, cost per action.

Chris: Yeah, yeah. Actually, we want to have some control over what is offered to our audience, what products. We really know who our audience are and who are subscribing. We really know the things that would excite them and what they would want. We want to have a bit of control over that.

Andrew: All right. Let’s go through some of the points that you sent me in preparation for this interview. First is about content. What do we need to know about putting content in the newsletters that we put together?

Chris: First in context, this was how would you build your own e-mail newsletter for business and how would you grow it? I was thinking before this, I was thinking, what are some of the things we did well. I kind of wrote some ideas down, and that’s what this is from.

The first one was around content. Originally, when I started this, I moved to Silicon Valley in June of 2009. Essentially, I didn’t freaking know anybody. I was going to a lot of these events really to meet people, and the problem is there is a lot of stuff that happens here, but it’s hard to know what’s quality and what’s not.

So I essentially started making this little digest. This is what this kind of came from, of events. But a lot of the tech media companies out there, TechCrunch, VentureBeat, Entrepreneur, a lot of them cover news. They cover analysis, but they don’t cover events. They don’t cover jobs very well. It’s the type of content you don’t really see, especially broken up in your local city. If I’m in New York City, I don’t really care what’s going on in Silicon Valley for events, nor would I care what’s going on in, like, Shanghai.

It’s very, very location dependent and time specific. It’s the type of content that’s not really offered or delivered anywhere else really well. From that point, it’s kind of unique, and it has a high value to the subscriber.

Andrew: You’re saying I’ve got to find something that’s unique.

Chris: Yeah. It’s a lot of the same thing that you’re thinking about when you’re coming up with a blog or coming up with content. What’s something that I can get that I’m uniquely capable of or a gap in the market that’s not really being fulfilled and basically delivering that through e-mail, which is a much better mechanism than blogs or any of that sort of stuff.

Andrew: You know what? You mentioned that I interviewed a few people who had successful e-mail newsletter businesses. Some of them sold their companies for high amounts of money.

Chris: Yep.

Andrew: When I asked them about their content, everything that they said that they created essentially could have been put into a blog, but because they decided to go into the e-mail space, they had a better lock on their audience. And so, it’s the same content, smarter delivery mechanism and a better relationship with their audience.

Chris: Exactly. I watched a lot of those interviews, the one with Ben from Thrillist. I forgot her name, I think it was Jennifer of Ideal Bites. Peter Shankman. I definitely watched them all. We keep up-to-date with the space really well.

Andrew: Useful as a person who’s in the space, are they useful, do you think?

Chris: Yeah. I actually subscribe to Help a Reporter Out. The value to a subscriber is awesome. It’s getting free press. All you’ve got to do is go in and scan there, and if there’s anything in my topic, I go and I reach out to the reporter. Who knows? I might get free press out of that. For a business, that’s extremely, extremely valuable. I’m willing to have them e-mail me three times a day. That one comes out pretty frequent, three times a day which is pretty crazy.

Andrew: I couldn’t deal with that. I’d have to unsubscribe. Speaking of . . . that’s the next point you want to talk about, which is frequency. How do you know how much to send to people?

Chris: It’s very dependent on the type of content. For example, Daily Candy and Thrillist, who I mentioned, they come out once a day, five times a week. We originally thought that ours was going to be five times a week as well, but the problem with events content is you plan your week from it. You get the events content on Monday and you plan your week from it, and then the content expires. It wouldn’t really make sense to send it daily. What are you going to say? Here’s today’s events. Here’s tomorrow’s events. It would get kind of annoying.

On the other hand, like I mentioned, Help a Reporter Out comes out three times a day, and the reason why it does it is when a journalist puts a query out there and needs a story, they need that filled fast. When a journalist puts a query inside Help a Reporter Out, it gets filled in less than three hours. So they really, really need a story very, very fast. It’s more on the type of content and who you’re serving. For us, events happen to be one a week, so that was kind of the right frequency we went with.

Andrew: But you found an excuse to send an e-mail a second time a week with the book list, right?

Chris: Yeah. For us . . .

Andrew: Let’s say not an excuse, an opportunity.

Chris: For us, we knew events we can never do more than once a week. We tried to do it twice a week. All the metrics and stuff weren’t doing so well, so we reverted back to once a week. For us, we thought, okay, what else could we send to our audience or what other types of content could we go into? And that’s how we got into jobs and the Reading List. Essentially it’s a very similar audience. It’s very similar in need, but it’s different types of content that we could send out on different days of the week.

Andrew: Okay. I looked at your home page before this interview, and it changed. I used to see a completely different home page. You know what I’m talking about? What did the home page used to look like, and then we’ll talk about what it looks like now and why you made the change.

Chris: What it looked like when we started or what did it look like now?

Andrew: How about take me through the home page in time? How did you start off? How did it evolve? Where is it today?

Chris: Like a lot of our interviews, our home page in the beginning was a terrible, terrible disgrace. We started this in November of 2009. Actually, when we started originally we didn’t have a home page. The first e-mail I ever sent out was straight through Gmail to 22 people. You never want to do that. You really want to send an e-mail through a sender, like MailChimp or Constant Contact or somebody. But at the time, we had no idea, so we sent that out through Gmail.

The reason why we came up with the website is people wanted to subscribe, and the only way is you could either tweet at me or e-mail me. At a certain point that wasn’t very efficient. We made a website. Originally, our home page was We couldn’t get the dotcom. And it was super, super simple.

It was just plain text on top, TheStartupDigest. There was a big, huge signup box in the middle. It said, “put your e-mail here.” Nothing else. We didn’t give you the context. We didn’t tell you what it was. It was made in just straight HTML. It was really, really terrible. This is now in January of 2010, basically one month last year.

TechCrunch was about to write a piece on us, but they said your website is so terrible that we won’t write about you until you fix it. They’re like, “Go get WordPress. Go get MediaTemple and make a sign-on.” So we got WordPress. We got MediaTemple. We made a site. It looks very similar to how it is today except we had a lot less cities. So, it was just a big thing with all the cities, and then we had like a little page about us. And then we had a little link like, “Hey, if we’re not publishing in your city, apply here to be a curator.”

Then, as we got more and more cities, now we cover 58 of them. It started to take up too much space in the home page, and people hit it and it’s like this huge form you had to fill out. We simplified it a lot now, so if you go the main page basically it’s still one big box for your e-mail address, but there are four steps you have to go through, taking you through the steps.

The only reason why we changed all this stuff is basically every single week we’ll A/B test something, and we’ll see what improves the conversion rate on the home page. We noticed when we did the step thing, it improved it around ten percent or something like that. So, we’ve stuck with that, just to simplify the process and not make it look so overwhelming when you get to the page.

Andrew: And your site, is the first time that I saw a Wufoo form created into multiple steps. I didn’t know Wufoo allowed that. So it’s just a basic form. It costs you nothing if all you have is one form, or costs you a few bucks if you have a lot of people filling out your form or you need multiple forms created.

Well, actually, let’s stick with the home page before I ask other questions. Your home page also used to have lots of links and lots of text. Didn’t it have more content than this at one point?

Chris: We still have a job board, and it used to be up there. Then, we had a couple of other tabs and other stuff at the bottom. Basically, one of my other points in growing an e-mail newsletter is really optimizing your sign-up page or your home page for a sign-up process. All that stuff is really nice, but really we’re trying to optimize. When someone hits our page, we want them to sign up first and then look at our other stuff. We really only care about the sign up. We noticed when we took off certain pages and we tested all the heat map of it, people are going out and stuff, so we just simplified everything.

Andrew: Get rid of anything. Your goal is just to get them to marry you.

Chris: Basically. And then, inside the e-mail newsletter itself, we’ll reference all of our other pages and stuff like that. Once you become a subscriber, you’ll start to notice some of the other stuff we do, but it’s not very apparent when you go to our site all the things we do.

Andrew: I’m telling you, if I had to do Mixergy over again, I wouldn’t do it in a blog format at all. What I would do is I would say is you have to sign up by e-mail. This is an exclusive group of people who are talking very openly about business. The only way you can have access to it is if you apply and get the e-mail address first and nothing else on the home page. It’s essentially what you guys are doing.

Now, when you don’t have anything on the home page, what about the content and the content sharing by Twitter or by Facebook or whatever else people happen to use? How do you encourage that?

Chris: Yeah. We really don’t. It’s kind of strange being a company in Silicon Valley. We don’t have tweet response. We don’t have to share this. We don’t Facebook. We don’t have any of that stuff, really. People will take links and share it and reference us and stuff like that. The one where we use it heavily is in the e-mail sign-up process. We’ll say, to share this afterwards and also we have a spot to include some of your friends’ e-mail addresses and stuff like that. When you sign up through the process, we kind of ask for a lot of those sharing stuff.

After that, we really don’t. The content really speaks for itself, and we try and keep it as super simple as possible just to get people to engage with it as much and really optimize for the conversions.

Andrew: Okay. Speaking of optimizing the home page, the other thing that I see on here is a list of testimonials, the founder of Lotus 1-2-3, the founder of Thrillist, the founder of KISSmetrics, really good people. How did you get the founder of Lotus 1-2-3 to give you a testimonial?

Chris: He actually just wrote about us, which is really freaking cool. This one was around the Reading List. He was signed up for the Reading List, and he really liked it. So he reblogged it on Posterous and wrote a little thing and tweeted about how this was the greatest thing that he was signed up for. So, we asked him, “Hey, is it cool if we use this quote?” He said, sure. We took the quote and put it on our home page.

The reason why we did that is actually because of Dave McClure. He wrote this awesome post everybody should read. It’s all about the mother f***ing faces. Sorry for cursing. When you put in someone’s face there, someone recognizable that a community trusts and use a real quote that they gave you, it really, really increases trusting conversions a lot.

Andrew: I see. It does for me. I take a look at these people. I think I’m impressed. I think whatever they trust, I should trust too. Okay. All right. By the way, the Book List, did you guys start it yourself, or did you buy somebody else’s list?

Chris: The Reading List? We started that ourselves.

Andrew: All right. I thought someone else was doing that.

Chris: Essentially, we were tweeting out these links anyway, because me and my co-founder, we stay up-to-date with the industry. We read Hacker News and TechCrunch and all this stuff all day anyway. We’re already tweeting out these links, and people are clicking on it. So essentially we ate our own dog food, so to speak. We turned that into a newsletter and send it out on Fridays.

Surprisingly, those have been our fastest growing issues ever in the history of what we’ve done. They’ve been growing, each of the Reading Lists have been growing at about 30 percent week over week.

Andrew: What do you mean? How can you tell that the Reading List is growing more than the overall list?

Chris: We can just tell on an individual subscriber basis. We track every single week how much a list is growing and over time, and then plot it all and look at it versus all the other ones. By far, those are the most subscribed ones. Probably a big function of that is it’s not city specific, so that one’s just one global issue for everybody.

Andrew: I see.

Chris: So instead of having to pick your specific city, it’s just one Reading List.

Andrew: Okay. Physical events, what do you mean by that? Why did you include physical events on this list?

Chris: I included that because in the very, very early days, like right when we started this, like I said, it was just for 22 of my friends. I was working at this investment fund incubator. It was kind of spreading in there a little bit, but the first big uptake, I went to this event called Silicon Valley New Tech here in Palo Alto. At the end of it, they invite people in the community to go up and just give a one minute spiel about what they did.

So I go up like, “Hey I’m Chris. I do this little events list in Silicon Valley. We send you the best events. If you want to sign up, just come up to me afterwards or tweet me.” And literally afterwards, like a whole crowd of people came over to me. That was the point where we realized, “Oh crap, we probably need a website.” That was the turning point.

With all these events, I actually go to a lot of them that I can. I go to on average, I don’t know, maybe like two or three a week. At any point in time, I’m actually looking for the quality, if the event’s actually good, actually keeping up to date with the community, telling people about it that have never heard of it. And then, any chance I can, I love to get up on stage and either give a talk or just give a short spiel for people to know about us.

Andrew: And that helps you grow your list.

Chris: Yeah. Especially from a trust factor standpoint when people see you’re actually active.

Andrew: I’ve got to say though, I’m thinking in my head, 100,000 people on the list. The number of people you can reach at an event, even a large group of people is a drop in the bucket compared to that. And then, those people have to remember to go to and give you their e-mail address and go through the form. That doesn’t seem like a very efficient way to grow.

Chris: You’d be surprised. People will notice when you speak at an event, because people when they speak at an event they are looked at almost like an authority figure.

Andrew: That’s still less than one, way less than one percent. It’s a fraction of one percent that you get from that, no?

Chris: For now, going 100,000+, going and speaking at a lot of these events, like you said, it’s not a super efficient way to try and grow your list. But especially when you’re just starting this, when we were like 100 people, these events were incredibly, incredibly valuable to us.

Andrew: All right. I can see how when you’re getting started it could be huge. Next point is partnerships. I really was looking forward to hearing you talk about this, because I’ve seen a little bit of what you do there. Tell me about partnerships and how that helps grow a mailing list.

Chris: Yeah, yeah. For us, there’s a lot of companies that serve a similar audience to what we do that have non-competing content. I mentioned some before, but you know, TechCrunch, VentureBeat, Entrepreneurship Magazine, Mixergy, you guys. We’re covering events, jobs, and a reading list. We’re not doing interviews. We’re not doing analysis. We’re not doing editorials. We’re not putting on own events, anything like that. Any chance we get we like to partner with larger media entities or people kind of generally in our space.

To get a little bit more specific, that goes in a couple of ways. That could either be just a straight events partnership. Events that are more than $200 that are reaching a larger audience, we either do swaps about us, or they’ll put us in their sign-up flow in return for extra promotion on the digest. Or we’ll just promote the straight media entity itself.

A real example we did with Business Insider is Business Insider really liked what we did. They reached out to us. We really respect what they did. I know a lot of the writers there when I go out in New York City. So essentially, we took both of our ad inventory, swapped it. They wrote a little spiel about us on one of their newsletters. They wrote an article about how to get trust from business insiders. So we said, “Hey, our audience, if you want press, go reach out to Business Insider. Here’s how you do it.” It was a great cross marketing partnership that allows us to both swap our audiences.

Andrew: They wrote an article for your newsletter, and you wrote one for them. Is that how it worked?

Chris: Yeah. We wrote one for them, and then they editorially changed it. They wrote one for us, and we editorially changed it and put it in.

Andrew: I see. Okay. All right. Inflow, that’s really clever. If an event wants to get more press, more attention from StartupDigest, all they have to do is give you a check box in the registration process. So every time someone registers to go to their event, they can also sign up to Startup Digest. That’s fantastic. That’s huge.

Technically, how do you do it? Considering that you’re using off the shelf tools, like Wufoo forms or subscription and MailChimp for e-mail, how do you do it?

Chris: A real example we did this in the New York Entrepreneurship Week. They used Eventbrite, and Eventbrite has a real simple thing where you can add in a custom field or add in an extra check box. We just do it real simple. They’ll just send us the list of people that were interested, and then we’ll send them a little auto e-mail, “Hey, this is what we’re about. Here’s how you sign up.”

Andrew: Oh, I see, you’re not automatically signing them up. You’re just getting an opportunity to say you should check us out.

Chris: Yeah, yeah. Because, for us, it’s a little hard because we have so many cities and so many issues. We don’t know exactly what someone would be interested in. We just found it’s easier to send them a little message afterwards. Of course, there’s a little bit of drop-off, but at least we’re reaching out to a new crowd we wouldn’t have otherwise reached.

Andrew: Interesting. And MailChimp lets you e-mail people just because you have their e-mail address?

Chris: Yeah. Even with Wufoo, there’s like auto form, transactional forms and stuff like that that you can use.

Andrew: With Wufoo, when someone gives you their e-mail address, you can e-mail them back and say, “Thanks. Thought you should check this out.” What else . . . I’m sorry. Go ahead.

Chris: I was going to say, it’s all permission based. Someone actually checked us.

Andrew: This is fantastic. Give me another idea of a partnership that you guys have put together?

Chris: Another one, more recently with our university courses, we did one here with Hackers and Founders here in Silicon Valley. We did a university course around hiring. We filmed a bunch of people, put it together in a package, and then we partnered with Hackers and Founders and said, “Hey, you’re going to invite all of your members to join this event with us. And then, also when the video is ready, you’re going to e-mail all of your members to go check out our video.” Then before that, we do co-branding. So it was with Startup Digest and with Hackers and Founders.

Andrew: I see. The video is on your site.

Chris: Yes. It’s actually on Udemy but that’s a whole different story. If you have promotional materials or premium content or any of that sort of stuff, there’s also a lot of co-branding opportunities that you can do with other similar organizations.

Andrew: What’s the deal with Udemy? Can you talk about that?

Chris: Yeah, yeah.

Andrew: When I say, can you talk about that, sometimes because I have personal relationships with my guests, and they tell me things that they don’t want to get into in the interview. And so I’m cool to back off as long as we know where we are. This is something you’re saying that you can talk about.

Chris: We’re pretty transparent and open about most stuff, so feel free. So we started doing these university courses, like I mentioned. Actually, my roommate is Gagan, who started the company, Udemy. So Udemy is an education platform for anybody to teach anything. They just raised a million bucks. They actually did a Mixergy interview. I saw that. Because I was with roommates with him, I heard him talking about all the things that they’re doing and they’re looking for more content.

I was thinking to myself, I was sitting here working one day, could we do what O’Reilly’s doing for books? Could we do that for education video content? Since he’s my roommate, I’m like, “Hey, Gagan, what if we made a course on Udemy. Would you guys be interested in that? He’s like, you’re my roommate. I would have never asked, but I would love to do that.”

So, we started doing these courses together. We both jointly do it. We pick a topic. The first one we ever did was on fundraising. We get a bunch of good speakers. We had Naval Ravikant, Dave McClure, Adeo Ressi, and a bunch of other guys, all speak about very tactical things on fundraising for one hour each. Put it together in a course, package it together in Udemy, and we sell it as premium content, and we host all that on Udemy.

Andrew: So, that’s just a revenue idea for you. That’s not bringing in any new members, is it?

Chris: There are people who see it that wouldn’t have otherwise, either from SEO or we actually do SEO word campaigns on it, or just general promotion or word of mouth. But the overall majority of people have come from our audience.

Andrew: Okay. All right. I know there’s a whole interview about how much revenue there is in e-mail newsletters, but I’ll save that for another time. Maybe I’ll ask you about one sponsor, about Charles Hudson and how he fit in. I’ll see if we can squeeze that in towards the end of the interview.

Next thing I want to ask about is consistency.

Chris: Yes.

Andrew: I know with blogging consistency is very important. People need to know that if you commit to doing it once a week on a Monday, every Monday they come, they are going to find something. If you do it daily, they want to know that. I always thought with e-mail consistency didn’t matter because you’ve got people’s e-mail address. You can go into their lives whenever you want as long as you don’t overdo it. Life is good.

You’re saying consistency is important there, too?

Chris: It’s just like with blogs. People expect a certain amount of consistency and a certain amount of content from you every single week. For us, it’s around events, so people are actually using this to plan out their week. So, we’ll notice that for whatever reason, let’s say, New York City or L.A. or one of the cities is late. We’ll see a bunch of people on Twitter, like, “Where the hell is Startup Digest’s email? I want my Startup Digest.” Everybody will freak out and we’ll need to do it last minute.

When you have subscribers, when you have customers, people depend on you for your product or for your service. If you promise it comes out once a week, you make sure it comes out once a week. That just builds long-term trust. In terms of subscribers, if people really trust what you do, really like it, they feel about better recommending it to their friends, telling people about it, getting them to sign up because they know that what you’re doing is very valuable.

Andrew: Okay. I’ve got another one here that’s mysterious. I love, by the way, that you put in points. Anybody who’s listening to this interview and compares it to an interview where someone is kind of going to wing what they teach in the interview can tell there’s a difference when the guest puts some effort into the program. So, I appreciate the effort and I know that it is effort. You’re not just pulling the list together at the last minute. You’re putting thought into it.

By the way, most people who think that they’re going to able to wing it and come up with some really valuable tips within the interview, end up with just three. And because there’s a short time period here, we’re only going to do the interview for an hour and because there’s a light looking at them, because there’s me expecting information, they can’t come up with enough. So, I appreciate it. I’ll move on now to the next point.

Chris: Thank you. I actually, personally really like Mixergy.

Andrew: Thanks, I appreciate it, and I’m a member of Startup Digest. As soon as I got back to the U.S., one of the first things that I did was sign up for Startup Digest. I did that and RunKeeper for my running. You guys don’t have anything in Argentina, do you?

Chris: No. Buenos Aires is one of the few cities we don’t cover. If you know anybody good there, let me know.

Andrew: All right. You say, social inside the sign-up flow. What do you mean by that?

Chris: This goes back to when you asked do we have Twitter or Facebook sharing anywhere? I said the only place we really have it is in the sign-up flow. Essentially, if you go to our site right now and you sign up, we ask you to pick the cities you’re interested in. And then, if you’re interested in the jobs or the Reading List or whatever. After that, the next step is something along the lines of “Woohoo, you’re now a subscriber. You are awesome. To share this to your friends and get more people to be entrepreneurs, tweet this.” And we use a little thing, a Click to Tweet, which actually Hiten Shah told me about it a while ago. Click to Tweet is awesome. It’s a super, super simple service where you can put in a Twitter message, and it changes that into a link. So when people click that, it automatically populates that in their Twitter.

All they have to do is click send. They don’t have to think about what to write or should I get creative? All they have to do is push send. After that, basically, we encourage people to tweet this link out to bring more people back into the digest who are their friends, who otherwise wouldn’t have heard about it. And then, the last step at the end is, “Hey, if there’s anybody specific that you know that might be interested in this, feel free to put in their e-mail address here.” Noah Kagan yelled at us and told us to do that, so thank you, Noah.

That’s actually very surprising. I didn’t think anybody actually would use that, but I think about ten percent of our audience who signs up actually put in one of their friend’s e-mail address in there. It has a very high conversion rate of getting people to input other people’s address.

Andrew: Now, you don’t automatically sign those people up to the list, right?

Chris: No, just like with an event partnership, essentially we send them that auto scripted message saying, “Hey, here’s what we’re about. If you’re interested, sign up.”

Andrew: You just take all the e-mail addresses. Maybe, once a week, maybe, more frequently than that, you put them into one list on MailChimp, and you send it out, and you say, this is the opportunity you have to sign up for StartupDigest.

Chris: Yeah. If they’re really not interested, they could forget about it. If they are or their friends thought they were, then they can sign up. It’s up to them.

Andrew: You don’t even say, “Hey, Gagan, your friend, Andrew, thought you should sign up to Startup Digest.”

Chris: We did originally except we were doing it manually. As soon as we got a lot more people, it started to become a little bit more. So, we just wrote a super personal message but not any specific keyword personal.

Andrew: Okay. I wish that there was a service that did that, that let me take the e-mail address of the person who just signed up and wants to share my stuff with their friends, take their e-mail addresses and address it properly.

Chris: If Wufoo is listening, here’s a product request. We would use it.

Andrew: I love Wufoo. It’s such an easy way to automate things.

Chris: I figured out the form or whatever. We’ve used Wufoo since the beginning. They’re an incredibly, incredibly helpful service.

Andrew: They just keep coming up with new techniques, new things that I can do with Wufoo. I could do a whole session. I could do a whole seminar on how you can run your business on Wufoo. I feel like my business does run on that.

I discovered this recently. There are rules in Wufoo. If you give me one answer to one of my form questions, I can take you to . . . what I mean is based on the answers that you give me, I can take you to a different landing page after the process is over. So, I can take you to a pay page, or I can say, oh, he’s not going to buy. Let’s find out why he’s not going to buy. I could do all kinds of clever things.

Also, for tweeting, I don’t even think that you need that website in order to create that auto tweet URL. All anyone has to do is do and then whatever they want. It will automatically pre-populate. I do that for my guests sometimes if I remember.

Chris: Click to Tweet is free, so it’s really simple. It’s this little box. You write the message. You put the little at reply or whatever in a link and it makes that URL for you.

Andrew: All right. It would be a lot easier to use. Click to Tweet.

Chris: Yeah.

Andrew: All right. What’s next here? Social inside the flow. Crazy exclusive deal. I won’t say any more. You tell me about that. What do you mean by crazy exclusive deal?

Chris: Yeah, yeah. Every once in a while, we’ll just hook our subscribers up with something really freaking cool. It’s something we’re so excited about it that we want to tell everybody.

A real example of this is when the “Social Network,” the movie came out. We basically begged Sony Pictures to let us do a premiere of it in San Francisco. We rented out an 800 person movie theatre. I guess this is another term of partnership. We partnered with our lawyer, who is one of our sponsors, and then also CMA Ventures. So, it was a joint thing with all three of us.

So we got an 800 person movie theatre. It was one night before the movie came out, and people could come and it was a premiere for it. We gave away, I think, 400 or something tickets to our audience. We just basically used our own ad inventory. We just put a little message on top to say, if you’re interested in this, here’s a link. The first 400 people get it.

That thing was freaking clicked and shared like crazy. We had like, I could be misquoting this, but like a 20 percent click through rate on that. People just went crazy for that. There ended up being a 300 or 400 person waiting list of people that wanted to go, but there weren’t enough tickets because there weren’t enough seats for the thing. Every once in a while we find something like really, really, really awesome, and we’ll just completely hook our subscribers up.

Andrew: And Manpacks, you also have on the list. Manpacks, was that effective for you?

Chris: Yeah, yeah.

Andrew: It’s a crazy, exclusive deal?

Chris: Yeah. I didn’t think people would be so excited about that, but I just noticed . . . because I have the search term for StartupDigest on Twitter. I noticed the day we did that so many people were talking about that. I was like, “Wow. This one did pretty well.” It’s kind of a unique product with a really good brand. People are really excited about it. Basically, we gave a 50 percent deal off for anybody who wanted to subscribe through us. I know a lot of people, some of my friends who bought it, like, love it.

Andrew: Here’s another one that I wasn’t sure if you were going to bring up because a lot of people who build mailing lists like to say things like, we grow by word of mouth. We grow because people happen to find us. We grow because we have good content. They never admit, and you do, paid acquisition. What kind of paid acquisition have you done?

Chris: That one I included. We don’t do much of that, just because we’re not very good at it yet, but we know it works. We’ve done tests of like social Facebook ads, Google AdWords campaign. Also, we’ll do AdWords on the specific university videos that we do, and that one has a cost associated with it, so we know on ROI terms if that works out.

But definitely if you have the money, it works. I know even though they probably don’t like to admit it, Groupon, Living Social, even different ones like Facebook Category and stuff like that, a lot of them use Google AdWords, Social AdWords, very, very social ads, very, very smart, driving people to become subscribers for them.

A good example is if you go to Groupon’s home page, the first thing they do is they ask you to sign up for their e-mail newsletter. You literally cannot see their website until you sign up or if you’re a subscriber already. They’re definitely driving a lot of people through their deals about it.

Like I said, we haven’t done a lot of it just because we’re not . . . we haven’t got the cost per subscriber down to a good science yet, but you can definitely just grow through paid acquisition. There’s also some more, like, if you look at the world of e-mail newsletters, there’s a couple of shadier things you can do, like co-reg buying, or you can do just straight list buy. Some people will sell it to you.

It’s usually not good, especially if you want to keep your reputation high. A lot of those subscribers end up not being the most high quality subscribers. For us, the partnerships is a lot more organic way that we do it, but it’s definitely an option when you want to try and grow an e-mail list into something you have.

Andrew: What have you seen that’s especially clever in the paid acquisition space?

Chris: I’m trying to think right now. I want to say, I think I actually heard in your interview what JackThreads was doing.

Andrew: Yep.

Chris: They were essentially leveraging the brands that they’re featuring to get subscribers for themselves. They’d be like . . . I can’t think of a brand they use right now. I’m not an active JackThreads subscriber. But, let’s say Levis. They would basically use the brand recognition of Levis and show their deals and use their brand name, so essentially get a subscriber for themselves.

Andrew: Right.

Chris: That’s the thing. It’s not necessarily partnerships. It’s kind of leveraging their brand in sort of a way. I don’t know how we can use that more, but it’s definitely a smart, kind of unique kind thing I learned.

Andrew: I see. What they’re good at, all these e-mail businesses is knowing the lifetime value of their e-mail subscriber. Once they know that, they can go out there and spend up until that limit. The reason that for them it’s easier to figure it out is because they’re not just buying a hit, they’re buying a member.

And they know how much that member is going to be worth over time, where if you’re buying a hit you’re kind of hoping that the person comes back tomorrow or hoping that they’re going to buy right frigging now. And people don’t come back tomorrow, and they don’t buy right now. If you have their e-mail address, in time they’ll be profitable for you. I see how that plays in.

Finally, SEO, I thought with e-mail what you lose is search engine optimization because with e-mail all of the contents in an e-mail inbox is locked in there, where with blogging you get all this content online. You give it away free, sure, without any commitment from users, sure, but you’re opening it up to search engines.

How are you finding search engine optimization working for you?

Chris: Yeah, this is another one. The paid and SEO were the two last points I gave. These are both we’re not doing that great, but we need to do a lot better at doing. E- mail newsletters do it. I know for sure that Ideal Bite did this really well, and Groupon did this really well. Essentially they put all of their old campaigns that they’ve done, all the text, all the editorial because all that stuff has very high value, high SEO, high keyword rich.

For us, it’s like we’re compiling a lot of these events together in a very local, specific area. There’s a lot of high value content going in there, but like you said, it usually goes inside someone’s e-mail box and it gets trapped and no one ever sees it again. How you unlock the value in that is essentially you make an archive section on your site, and then you put up a huge header, something like, “Hey, this is an old issue. To sign up for the new one, subscribe here.”

So, you’re getting all of the people who came to your last one, and they want to subscribe to the new one. Since we’re publishing 60+ different newsletters, it’s getting all the content archive correctly is a little bit of a nightmare. We’ve kind of outgrown MailChimp in that aspect, but we’re actually in the middle of making a product for ourselves to kind of automate that, so to speak, to make that a little bit easier on ourselves. But that’s definitely one way you can leverage all of the content you’re already doing for the newsletter for the SEO benefit.

Andrew: You could probably even automate it using a WordPress plug-in, can’t you? Where you have each e-mail go into your WordPress and create a post for you and tag it up and have it go online.

Chris: Some of the problems, I don’t know if it’s a MailChimp specific thing. I think it’s an e-mail specific thing, but usually when it sends to whatever e-mail sender you’re sending, it kind of templatizing everything, like puts it in these weird CSS boxes. And it’s really hard to put that somewhere else.

This is also a product idea. If someone can make a real freaking simple thing to do exactly what you said, I want to send something and put this in there and keep doing it every single week. No one’s been able to make something like that, so we’re having to make something ourselves.

Andrew: Yeah, you’re right. I’d love to have a system like that, that worked easily and no one does do it. It’s too bad because more and more people are creating e-mail newsletters. More and more, if they’re not focusing their businesses on it, they’re adding it to their business, and all that stuff is good to have online. It’s good drawing new users at SEO. It also means that you can let your users tweet it out. So, you don’t just want to post it on the webpage. You also want to add a tweet button within each e-mail, and when people click on that, what they’re doing is tweeting that archive page which is another opportunity for you to promote.

Well, this is extremely helpful. But here’s what I’m thinking. 100,000 people in a matter of what? Two years? How long have you guys been in business?

Chris: One year and two months.

Andrew: One year and two months. 100,000 in one year and two months. Can you really get all that from this list of ten techniques, especially when the last two you’re not really fully utilizing? Where’s the biggest bulk of your users? Where do they come from?

Chris: I think the first point I made, it’s the type of content. Like I said, for events, jobs sort of stuff, it wasn’t very well served. If I was to ask you, “Hey, Andrew, can you tell me the best startup events in Tokyo next week? Can you send the list to me?” Sure, you can go on Eventbrite or PlanCast or MeetUp or Facebook and try and pull some of this down yourself, but it’s a huge pain in the ass.

Andrew: That’s a problem that I have today. It’s not necessarily a problem that I’m going to remember or think that I’ll have tomorrow. What I mean is, I might be ready tonight. It’s a Thursday night. I want to go check out a tech event. I might go online right now and check it out. If I see that I have to sign up to a newsletter that won’t come out until the following week, I’ll say, “All right. You know what? Maybe I don’t need it now. I’ll remember to do it next week,” and pass it on, no?

Chris: Like I said, events are very location specific. That instance might work, if you’re visiting Tokyo or you’re visiting Tel Aviv or somewhere, but if you actually live there and you actually want to be part of the startup community, or you want to start your own thing or you coming out of college, or you just want to keep up-to-date, you want something that’s going to help you on a continuous basis.

Andrew: Okay.

Chris: So, it’s not so much for the person who’s kind of, sorry, no offense, a little bit famous and knows what’s going on and people tell you stuff. But it’s really for people on the fringes. If you’re a new student or, like me, I just moved to Silicon Valley, where do I find this stuff? It’s incredibly, incredibly hard for me as an outsider to really get connected to this industry.

There was no past resource that really kind of helped me get connected within this world. This is one of the few and entrepreneurship has an affinity to it. People are very passionate about this topic. It’s a very hot thing right now. We started it in the crash, and no one really cared about it. Now, it’s a hot thing and everybody likes it. That probably very much helped us as well. Yeah. It’s just something that wasn’t being served very well.

Andrew: All right. I want to end with advice for anyone who’s listening to this, but I want to keep in mind that we just gave them ten very meaty points. I could see that at the end of this interview some people are going to feel inspired, and some people are going to have a list of notes, a big set of notes that they’re going to go act on. And others are going to say, “Where do I start? What do I do first?”

So, for someone who has an e-mail list, they want to build it, what’s the one easy thing that you can tell them to do that will give them some quick results and make them feel proud of their accomplishment and hopefully get them to come back and follow up on the rest of the list?

Chris: Yeah, yeah. Great question. I actually wrote a blog post about that. There was a guy from New York City. He just e-mailed me randomly out of the blue, and he’s like, “I want to do an e-mail newsletter. Where do I start first?” He’s like, “Can I call you?” Because he saw that we had an e-mail newsletter? So, I was like, “Okay, give me a call.”

I talked with him over the phone and said a whole bunch of points. Basically, I took what I thought and I wrote it into a post. So I’ll kind of paraphrase that. The first thing is you really need to find out what you’re uniquely capable and passionate about. For this guy, it was . . . I want to say, but I could be wrong, but I think his content was kind of around food specific events going on in New York City. He loved going to this stuff. He went to all these events, like, this was his thing. He knew about this. He wanted to tell other people about these type of events in New York City. Actually, I think it was fashion. I could be wrong. That could be another guy. Anyway, sorry.

But whatever that is, whether you’re into fashion stuff, or maybe you’re into interviews, or maybe you’re into, I don’t know, something crazy like babies clothes, whatever the hell you’re into. Find out what you really, really, really like and figure out the type of content you’re going to do, whether that’s news stuff or that’s articles or that links, whether it’s information or events that we’re doing. Figure out what you’re really, really good at. And then figure out, like I said, all these points that I talked about, you know, the consistency of the type. And the first thing is just go out and try it and send it to ten of your friends and see if it resonates.

I actually have a friend. She just started one on kind of like cool parties and things happening in San Francisco. I basically told her the same thing. So, she started and put a little list of five stuff going on and sent it to her friends. Her friends wrote back and were, like, “Hey, this is really good. I actually went to some of these events.”

You can see it resonate. You can see there might be something there, if people are kind of resonating with it and they’re kind of finding it. Kind of like with any publishing or any blog, the first thing you really need to think about is what do you want to write about? What do you want to talk about? What do you want to be in that newsletter? And then, start to look at all of these mechanics.

Andrew: What about if they have it and they want to grow the list? They’re seeing that you have 100,000 people. They’d like to get a piece of that action. How do they get more people? One thing that they can do.

Chris: The second thing is even though, like you mentioned, it’s very hard to measure this and it might not be the most efficient. Actually be active in whatever you’re writing about. If you’re writing about food events, go to food events and tell people. If you’re going to fun events, do that. If you’re writing about fashion news, like go hang around fashion people. Actually be part of whatever community you’re talking about.

People will never find out about you or know about you if you’re on the fringes doing this at home. But if you’re actually in front of people who are going to take notice of this, that’s when you really start to see the beginnings of it.

That’s the story of how we started. I actually went to these events. This is a product I made for myself. It wasn’t necessarily I was trying to do this big newsletter company. This is something I needed when I moved to Silicon Valley.

Andrew: All right. Well, there’s a great place to leave it. The website is

I’m looking for suggestions from the audience here. I’m going to ask them what kind of follow-up interview can I do here? How can I make this interview more tactical for you? I’d like to have Chris come back here and make this stuff even more useful than what you’ve heard.

So come back to Mixergy. Give me feedback on how you’d want to see that done. What else do you want to hear from Chris? What else do you want to know about e-mail newsletters? Come back and tell me that, and check out StartupDigest. I’m sure it’s in whatever city you happen to be in, or you can put it in your city and be the curator if it doesn’t exist already?

Chris: Yep.

Andrew: All right. Thanks for doing the interview.

Chris: Thanks, Andrew.

Andrew: You bet.

Chris: You rock. Peace out.

Andrew: Bye, everyone.

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