Tech Cocktail: Bootstrapped And Profitable In 20 Cities

How does and entrepreneur do events in 20 cities and draw 30,000 guests to those events?

Frank Gruber is the founder of Tech Cocktail, which is known for its evening events and conferences for startups and also publishes Tech News.

I want to find out about why he decided to quit his job when he had such a great job and what impact it had on his business. I’m going to ask him how he got his sponsors and what happened to his content since March 2010 that impacted his traffic.

Frank Gruber

Frank Gruber

Tech Cocktail

Frank Gruber is the founder of Tech Cocktail, which is known for its evening events, conferences for startups, and also publishes Tech News.



Full Interview Transcript

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All right, let’s get started. Hey there, freedom fighters. My name is Andrew Warner. I’m the founder of, home of the ambitious upstart, and the place where over 700 tech entrepreneurs have come on to tell you how they built their businesses so that you can learn from them, pull out their best ideas, implement those ideas, and go out there, build your successful company, and hopefully, hopefully, you’ll be as generous as today’s guests and come back here and share what you’ve learned along the way. So, how does and entrepreneur do events in 20 cities and draw 30,000 guests to those events? Frank Gruber is the founder of Tech Cocktail, which is known for its evening events and conferences for startups and also publishes Tech News. Frank welcome.

Frank: Welcome. Thank you very much. . . .

Andrew: Good to have you.

Frank: . . . I thought you were still going to keep going.

Andrew: I kept it short. And we did agree . . .

Frank: Yeah.

Andrew: . . . before the interview that of course we’re going to drink, we’re going to, . . .

Frank: Yeah.

Andrew: . . . we’re going to be relaxed here and talk about your story.

Frank: Start out with a drink. I think that’s appropriate.

Andrew: What size revenue are you guys doing?

Frank: Oh, right for the . . .

Andrew: Right for the, yeah, right for the big question.

Frank: I’m not going to get into specifics, but we’re in the six figures. You know, we’ve been growing now for a few years and we’re boot strapped, so everything that we, you know, generate goes back into, you know, paying all of our great people.

Andrew: Boot strapped and profitable.

Frank: Yes.

Andrew: OK. I can’t get the revenue out of you and we talked beforehand that I [??] . . .

Frank: To give you an idea, we don’t have a team jet yet, but, you know, obviously.

Andrew: No team jet. How many people on the team, though, that’s a good indication.

Frank: Yeah. So our core team, I’ve been saying ten, you know, where it’s half operations and half, you know, editorial. Summer contractors, but they work with us, you know, a lot, you know, the majority of their time. So yeah, I’d say roughly ten. And then we have an extended team with developers, designers, as well as contributors, so people that want to just write or want to just help us in some way . . .

Andrew: OK.

Frank: . . . in a city. I think that networks around 30. And then we probably, God, we’ve got a queue of writers that want to write around, like, 200 or something and we just need to [??], you know, go through and really, you know, see which ones want to really do it versus just send us articles about their company.

Andrew: All right. So, the vision that I have for this interview is we’re going to go back in time and see where the idea came from. We’re going to find out about that one conversation you had of Potbelly and how it helped you find your co-founder and made the whole thing take off.

Frank: Yep.

Andrew: I want to find out about why you decided to quit your job, when you had such a great job, to do this and what impact it had on your business. I think anyone who’s working part-time is going to want to hear that. And I’m going to ask you probing questions about how you get your sponsors, and we agree that we’re going to talk about how you did that. What happened to your contents since March 2010 and how traffic has been impacted by that? I think that’s something people want to know about. I might ask you a few more questions about revenue, which you’ll be free to say no to, but we’ll see what happens. But first, I want people to get a sense of how big this is, and it’s really hard because we’re just having a conversation. I can’t flash a photo up of the audience of an event. So why don’t we pick one event and just quickly describe what happened there, so people get a sense of why I invited you here and not just some random guy who’s throwing meet ups on

Frank: Right.

Andrew: Do you want to talk about maybe the South by South event that you just did this year?

Frank: Oh yeah. Sure.

Andrew: Who was there?

Frank: OK. So South by Southwest I mean, it’s kind of a full few day of events. But our evening event we had about 5000 people registered for. We had a stop in for Steve Case honor of AOL. Scott Case who was CTO at Priceline. Now that he’s meeting up with Star of America. You know we had Dotco as a big partner and sponsor. And they, you know, [Malon] from Dotco was there.

And throughout the day we did an interview series on the stage. And so we had Tony [Feshay] stop in. Jane Lynn from [?] with happiness. We had a great Bo Fish [?]

We had a bunch of people come through throughout the day. And during that day we had a breakfast event, a lunch event. You know, I think it was Robin themes it was like start of life. Hashtag, start up life and celebration and so forth. And it was raining. So it was nice to have the space where people could come in and hang out. And in some cases meet people that they never thought they’d be able to. Because we’re kind of bringing everyone together. It’s literally cocktail type people.

Andrew: All right. And you do get big names. Even at the conference here that I spoke at tech at…

Frank: DC.

Andrew: DC. Exactly. Steve K showed up and spent some time there. Who were the other big names who’ve showed up?

Frank: Well, I know them from, you know, Steve to Charles Callaway from Auger. Jerry V was at our first conference in Chicago. [Pecaslo] who’s now the CEO of Twitter, at the time he was our feed burner, he’s in Chicago.

Andrew: And when you say 5000 people register for the event of South by Southwest..

Frank: Yeah, they did.

Andrew: How many of those show up?

Frank: So, that’s a great question. We wanted to get it quicker this year and I think it fell off the radar. Because of just the other things we’re doing. I’d say it’s a river, right? South By is a river, and if I had to guess, I’d say about 2700-3000. I don’t know off the top of my head.

Andrew: Do people pay to show up at these events? In this one specifically.

Frank: In a lot of cities, yes. South by Southwest is its own beast. It was basically anyone that had a badge could come through. It was an official event.

Andrew: And when you say an official event, do you have to pay for that?

Frank: You do. You have to be a sponsor of South by Southwest.

Andrew: How much does it cost you to sponsor South by Southwest?

Frank: Yeah. It depends. There are a lot of different entry points. You could be a part of their expo. Or you can get an advertisement. We ended up with a, I don’t know, a full page advertisement or a half page advertisement, that was like 3300 dollars, something like that.

Andrew: So you pay 3300 dollars in exchange for an ad and I guess it being an official event. What else do you get for being an official event?

Frank: Really schedule. You get to work with South By directly and also they do sometimes help with, you know, finding different things. Like in some cases Ben uses them [inaudible] cases sponsor participants who want to be involved.

One thing I have to mention though, is everyone that’s involved in our event has to then be a sponsor of South By before they can just participate. So, it’s almost like, you don’t only just pay South By, they also help you out.

Andrew: So Tony Shay, if he’s coming in to be in the event and or Steve Case or Dotco, they all have to be part of South by Southwest.

Frank: Oh no, no. I’m sorry. Attendees are free they just have to have a badge. And obviously if you want to have, let’s say, our sponsor Dotco had to be a partner or a sponsor of South by Southwest first.

Andrew: OK.

Frank: So it’s just like anything that we do we kind of have to..

Andrew: I see. They don’t want you leeching sponsors who would otherwise be their sponsors.

Frank: Right.


Andrew: I’m sorry to interrupt that. Where does revenue come from then if you have 5000 people registered, a few thousand people show up but none of them pay?

Frank: That’s a different dynamic than usual.

Andrew: OK.

Frank: We see South By as it’s own little beast, our baby actually. So in that case it’s advertising and sponsors. So the Dotcos of the world. Arbiter, Constant Contact, MapQuest, those are kind of all of our sponsors.

Andrew: I see. OK. All right. Let’s go back and figure out how you built this whole thing up. Starting with, where were you just before you launched Tech Cocktail?

Frank: So I was in Chicago, I was living in Chicago. And I was working at the tribune. And doing a lot with syndication and kind of the newer technologies that web to as a step, and I was blogging. You know, and I’ve met through blogging people like [Pecash Moore], Mike Larington.

Andrew: Pecash Moore of [Nashville], Mike Larington of course of tech crunch.

Frank: Right.

Andrew: So you were blogging at the time. They were blogging at the time. You were connecting. Why was this, like this was the prime time to be a blogger?

Frank: Yeah. It was.

Andrew: Why?

Frank: Because of tools. Tools came out and they became really easy. The barriers became really easy for anyone to start a blog and have a voice. It was before Twitter and Facebook existed. So if you can think of a timeline before that, yeah. It wasn’t that long ago, right? And so things like blogger and goggle tech and word press were just getting going and there was a big acquisition of Jason Calacanis, Red Blog Inc. and I think that spurred a lot more interest in blogging.

Andrew: And before then Jason, I think, was showing how much money he earned from blogging, I think, I forgot what sized check he had but he showed a check, I think. But beyond that it doesn’t seem to me like it was the money that was drawing you personally into blogging.

Frank: No, it wasn’t.

Andrew: You’re in the middle of nowhere and no one knows you and this is the way most of the people were before blogging and suddenly because you can sit and type out intelligent things and report on what’s going on, people start to get to know you and people who you never would have contact with are suddenly basically your friends and colleagues.

Frank: Oh, that’s exactly right and it’s connecting me with people across the world.

Andrew: For example, do you have an example of someone who you met as a result of this blogging?

Frank: Yeah, Mike Garenton’s [sp] a great example. We were commenting back and forth and two or three months later I’m in San Francisco meeting him and hanging out and it turns into a situation where six months later I’m helping write content for Tech Coach.

Andrew: Commenting back and forth meaning that at the time he was still commenting on people’s blogs actively and you were one of the blogs he was commenting on.

Frank: Exactly. You look back at some of the early 2005 posts, he’s linking back to things I have written and we’re writing comments and the same with Pete Casmore [sp] as well; his first site was on I remember the header specifically, it said Mashable and that’s it and now they are humongous. It’s been interesting to watch and fun to see those guys do really well.

Andrew: I do remember that and, actually, you are one of those people who I got to know remotely just through your blog, through Somewhat Frank, through Tech Crush was writing about you. It was starting to be this little buzz of certain people getting written up and certain people being discussed and you were one of them and that’s how I got to know and, in fact, I’m going to write a note here to talk about how you and I first talked. But, let’s move on with your story, Ben, your publishing these blog posts, you’re getting this reputation, connecting with important people in the space and then you have this conversation with Pot Belly that I hinted at earlier. What happened?

Frank: We had just gotten back from trips back and forth between valley and Chicago and was blogging like crazy and I ended up through that meeting some folks in Feed Burner, I was working with Feed Burner, through a friend who had commented, I believe it was Rick Clow, he’s over a Google now running their start up program, he connected me with Eric Olsen and Eris had just moved from Boston to Chicago and we went to a nice fun dinner at a Chicago based startup, at the time, Potbellies, and had some subs and talked about what we like to do and I kind of tossed out the idea of doing this kind of connecting the early stage startups with the bigger companies that are in the area.

Being from the area I thought that was needed and he was from Boston and he saw that kind of stuff happening out there and I knew the area and needed to do the same thing, let’s bring this community together to see what’s out there and we thought 50 people would show up at this first cocktail meet up sort of thing, mixer. We had not sponsors we go wine donated from Huma Cloud, he was doing this dinner thing and he sent a bunch of wine from the store hook and, yeah, we got a venue and literally hosted this event that 250 people showed up to.

Andrew: 250 people show up to an event in Chicago. Let me take a step back though. I want to find out how that happened. But, when you met Eric, your co-founder, you told me right now that one of the reasons why you’re blogging is you want to leave a mark on the world, you want to stand out. And I know that’s something that my audience wants to do a lot. Did you feel the same energy from him? Was he someone who’s like I got to do something and leave my mark and not be just another guy reading someone else’s thoughts in a blog?

Frank: Yeah, he really had a lot of positive energy about doing something and he has literally packed his car up a couple weeks before, drove across the county with his girlfriend, not even having a place to stay to work for a startup and so that startup was Feed Burner and so, you head stuff like that you’re like wow, you are passionate about this and obviously he was, we worked on this for 3 ½ years together.

Andrew: What does that drive that we have to take a drive out to the middle of nowhere if we have to just to build this business, why is it, who do you have that?

Frank: That’s a great question. I think the trite answer is to cause positive change but I really believe that anybody and can do anything and obviously we want to try to impact the world in a positive way and I saw an opportunity to do that in Chicago in my home town and other people noticed. That’s the part that was really, I guess, interesting to us. Within the first year, we had people in Boston and Boulder, we had the Tech Stars guys reaching out. Before we even knew what Tech Stars was, they were reaching out and wanted to work with us as well as D.C. Nick O’Neil was the in D.C. who was reaching out like crazy like, “Let’s get Tech Cocktail in D.C.”

So within the first year, this part-time labor of love, it turned into something we were doing in four cities and bringing those people together, better telling the story. And other than just having cocktails, one of the components was, “Let’s showcase early stage tech companies.” It’s always been that way. It’s been to amplify the local signal on what people are doing. So we showcased, in that first event, six startups.

Andrew: So you found six startups. You gave them tables where they could set up their computers and show their work.

Frank: Yeah it’s funny. We first started that event with, “Let’s have them pitch,” and people were having cocktails and having fun and the first one tried to go up there and we couldn’t get the attention of the audience long enough to make that happen. So we decided, “Let’s just let them do it expo-style and it’ll work.” I don’t know if you’re familiar with Christian Perry, he was one of the first people to do it, do one of our demos. He had a ticketing site and went on to go to the Valley and start SF Beta, so a similar kind of thing out there. Some others, geez, we had . . .

Andrew: Mike Macadaan did something like that in L.A.

Frank: Right.

Andrew: Were you pissed when all these guys were copying what you did?

Frank: Yeah. But you know what? It’s flattering because that each one of those things was needed.

Andrew: But you were a little upset that they were copying you?

Frank: No. Actually, I helped them.

Andrew: You helped them?

Frank: Yeah. So like with Macadaan, for example, I wanted to help him as much as possible and shine a light on it so, obviously, covered it and I thought it was necessary. And working with him directly, I was working with him at AOL, so it was, you know, he’s a good guy and it wasn’t anything like . . . I feel like it’s not a zero sum game. There’s opportunity out there for everyone to kind of have their own little piece and do what they need to do.

Andrew: But if Mike is locking up L.A., which he ended up doing, and, as far as I know, Tech Cocktail isn’t there, right?

Frank: Oh yeah.

Andrew: Oh, it is now. But it wasn’t there for a long time. If he ends up locking down L.A., and someone else ends up locking down New York and someone else ends up locking down Northern California, then you don’t get to grow Tech Cocktail there. Aren’t you thinking about that when you’re launching this business?

Frank: Yeah but, like I said, there’s 365 days a year, or 364 ½ or whatever, and there’s a lot of opportunities for events like this and there’s hunger for it.

Andrew: So if Mike does just four events a year. That still leaves you with over 360 events to do the other 360 nights.

Frank: Right.

Andrew: But sponsors aren’t going to sponsor every single night of the week if you can throw that many events. They limit themselves, don’t they?

Frank: They will. They will. I think the best stuff will bubble itself out.

Andrew: So you’re just saying, “Hey, you know what? All right, so that means that if you’re the best, you don’t get hurt.” But what’s the benefit of helping them? I know there is a benefit, I just want to explore what that is.

Frank: What’s the benefit? I think the benefit is, ultimately, has been our mission from day one, which was try to amplify the local signal in what’s happening. For me, personally, that’s my mission. If it ends up hurting us in some way, I think we’ll be OK.

Andrew: It could also be that, “Hey, you know what? If Mike Macadaan does well, and Mike happened to, at the time, work for A.O.L., then he’ll be happy that I helped him out and he’ll help A.O.L sponsor my events.

Frank: Yeah, it draws attention to the whole space and validates it.

Andrew: Right. Because you built a friendship with the guy who gets the sponsor in L.A., maybe he’ll send that sponsor to you in Chicago and then you’ll move that sponsor to D.C. and that’s how it all helps each other out.

Frank: Yeah and, ultimately, he did great. He built huge events there and then ended up selling it so, for him, that was a win, right?

Andrew: Yeah.

Frank: And then went onto write MySpace and things like that.

Andrew: And he ended up coming in and speaking at one of your events.

Frank: Right.

Andrew: So you do get into a situation where if you don’t talk to your competitors, they’re going to talk to each other. Or if you don’t talk to people in your space, they’ll talk to each other and help each other and then you’ll be frozen out of all that support that you could get.

Frank: Right. And, ultimately, we’re still doing L.A. events and they’re big. We work a lot with local people. We have more of an umbrella-type view. Like he was in L.A. at the time and he’s doing great things. We don’t want to like storm in and say, “Yeah, we’re going to take over L.A. That’s not our approach but there are people that do that and I just can’t believe it. Why would you even try that? Our thing is more like, it’s not a zero sum game. We’re going to come in and work with you directly and we’re shine a light on even the stuff you’re doing because it’s going to actually help the entire ecosystem.

Andrew: I talked to an interviewee recently, the founder of SpeakerGram, and said that he wished he talked to his competitors early on instead of fighting them and shunning them, that he would have figured out the market a little bit better and maybe would have worked with some of his competitors better. Instead he ended up closing it down and moving in a different direction. All right so you guys launch this thing.

Frank: Yes.

Andrew: You get 250 people to show up. Tell me how. I mean we’re not talking about a community that already had been formed. We’re not talking about a place where there were blogs that were dedicated to the community that you can reach out to.

Frank: Right.

Andrew: No one had a mailing list of local people.

Frank: Right.

Andrew: How do you overcome that challenge.

Frank: Yeah, I think initially it was very much word of mouth. I emailed a ton of people that I knew in the area. You know it was just one of those things. Yeah it was a lot of hustle to begin with. You know what, to be honest with you we were not even sure if the people that were emailed would show up. The commenting on our blog post was the way that we RSVP’d so if you go to our first blog post ever; we just put out a blog post and said here sign up here. Look at it now there is two hundred and something people signed up. And we were like oh right is that really going to happen. And sure enough it did. I think there was such an electricity about web 2-0 and the social movement online that it made people super excited to get together. And if you think about it was before tweet ups and things happened. Like there was nothing else like happening like that.

Andrew: You emailed your friends and you had a good list. Eric emailed too. I went back in time and saw that Eric did a blog post about it. I think he was also an influential blogger at the time.

Frank: Yes he had his own blog. Frank has a blog. We leveraged our own blogging communities to kind of get people out there to know about it. What else did we do, yeah there was no real mainstream player or anything like that you know.

Andrew: Okay so that helps a lot. You have a big network, he has a big network, your blogs have good reach and you’re emailing everyone and sending them all to a web page and in the comments asking them to RSVP. I have noticed that a lot of entrepreneurs do this they’ll just start out with the quickest, dirtiest first version that they can.

Frank: Yes.

Andrew: I did the opposite I started some how building my own invitation site for my fans. Don’t you feel like boy this is an event that needs to look good so I’ll start off by getting a nice invitation, maybe use E-vite, maybe build something. No. Why is commenting? Why is the easiest solution the best solution?

Frank: Well you know we could have gone E-vite I guess but it wasn’t exactly what we were trying to do. We just thought it would probably get the most reach if we made it very open and put it out there. And so we didn’t want to exclude people and so the easiest was let’s put up a site. If you would have seen our site man you would have laughed. The logo I made was literally on a napkin then I had somebody that had better skills than I did take that napkin and design it. And it was a big neon cocktail glass and we had that for a long time. But the site itself was a WordPress site put up with in, not very long, probably like with in a day or something we got it all ready to go. And the logo was probably half the screen so we were looking at a logo like that big.

Andrew: I remember that.

Frank: It was in your face.

Andrew: Yeah and on the right side there were sponsors which I’m going to get to in a moment to see how you got them because that is where the revenue was. Were you charging the 250 people that showed up to the first event.

Frank: No, it was free.

Andrew: The tables was that before the event that your decided you were going to give the start ups who were showing off tables.

Frank: Yeah, the idea was to always better connect and amplify the stuff that was happening. So getting those people there was important. And then also inviting people from like the Chicago Tribune and the Tribune Company, Playboy, Boeing, Motorola. Getting all of those people to show up and see these companies. And bridge the gap between the bigger companies and the start up.

Andrew: Right, I see if those guys were local then they should have known about the local start ups too.

Frank: Right.

Andrew: Now you don’t have contacts at those companies, right? Do you have a contact at Playboy? Do you have Hef’s email?

Frank: Not really so that was one of my skills was trying to find those people I really do.

Andrew: So how did you find them?

Frank: I guess I stalked them online. I don’t know you know I looked on Playboy. I tried to find contacts. I would reach out to them via email. Just really hardcore reaching out. I guess it would be a little bit of grass roots marketing. A little bit of hustle on line.

Andrew: Do you know anyone at Playboy they are local they have to come out. Do you have a friend who works there?

Frank: Right. Exactly.

Andrew: Do you have a friend who knows a friend? That kind of thing.

Frank: Right.

Andrew: Most people at that point after they realize that they just don’t know anyone would’ve just given up or whined about it. We need to have connections why are people from new media being shunned by old. How do you clear the hurdle instead of whining about it? Which is another thing I notice a lot of entrepreneurs do?

Frank: We just don’t, I just wouldn’t.

Andrew: You’re not built that way.

Frank: Yeah. We figured, you know what, this is an important thing that we’re trying to do here. And the mission was critical to the area and I thought that they should know about it. And I didn’t have any shame in letting them know that that was the most important thing that they should do on that particular day.

Andrew: All right, the start ups do they pay?

Frank: No, no, no.

Andrew: Nothing. The guys who show off don’t pay it is just sponsors you got sponsors. Did you get sponsors for the first event?

Frank: No.

Andrew: No, so it was just: “Hey, let’s do this”.

Frank: Wait, let me, let me answer that. We didn’t have any sponsors at the first event until I think after the fact, and then I think we got one for like five hundred bucks or something. Yeah, I think it was a hosting company called Middays, that saw what we were doing and I think they threw out five hundred bucks right afterwards because, everything, like, I got the wine donated, I had – My family was there so-, It’s actually a funny story. The venue we got, we locked down, it was a brand new venue, had a lot of technology in it, that’d be great because the crowd, right? And they didn’t have their liquor license when we locked it down in like April or May, and they said: “Oh, we’ll have it by July, no big deal, we’ll get it”. Well apparently, that didn’t work out.

So, July 6th came 2006 they have no liquor license. So I’m like, “Well how are we going to serve this wine?” We’ve got cases of wine, we’re supposed to have cocktails at the bar, they didn’t have anything. So I had to literally have my family pass out wine. Family and friends, that had come, you know I’m from that area so a lot of them come in. My sister was out there and they were pouring the wine. And if they didn’t do that we wouldn’t have had any [??].

Andrew: So I talked to a lot of entrepreneurs who will launch and then something bad will happen like that and they’ll go “Well…

Frank: Yeah.

Andrew: âĦmaybe it’s not meant to work. Maybe for some reason I’m not the right guy to make things work. I can’t even get the liquor.” You keep going, despite that. Why?

Frank: Those are just things-, You know that’s a journey man. It’s a roller coaster and things happen and those are just little bumps along the way. It wasn’t, you know, the first time is not going to be exactly how you want to do it. Like, you know that. You just got to know that going in and just be resilient.

Andrew: All right, get real with me for a bit.

Frank: OK.

Andrew: Tell me about the time when you felt really depressed as an entrepreneur, where you said “Hey, you know what, things just aren’t working out. I see all these friends who come to the events and they’re just becoming superstars and I’m not going anywhere” Be…

Frank: See…

Andrew: be open about that depression. And then I want to know how you felt that depression and then did it anyway.

Frank: Well, I think that there’s times like that every single day. Like every day’s a roller coaster…

Andrew: To this day. So you’re saying in the last thirty days you’ve felt it more than a dozen times, this sense of…

Frank: I’m not so much, I don’t really, I don’t worry so much about the other people as much as I feel like, maybe I’m not doing enough. I put [??]

Andrew: Maybe, you’re not doing enough and that’s why the business isn’t growing faster.

Frank: Right, but I’m starting to realize that, you know, as I grow as an entrepreneur it’s like, I need to make sure that the people around me, I give them the right and ability to just go and do what they need to do. And it’s been amazing the last, you know, I’d say few months we’re starting to really have a team together that can just execute. So I think, you know, every single day there’s things that are ups and downs, and you know, you’ve just got to know that’s it’s going to come back, you know like, we do an event and we’re like up here. And then you should have seen me like the Sweetheart event Saturday and I was like riding high, and I was up there a little bit higher than I thought.

And then, you know, probably Sunday night I was starting to come down. And then I was like “Oh, man” Like I was still at softbine – but I’m still like pretty outgoingly happy it’s just that I’m like “Oh, that was”, you know it’s a lot of energy that you’re just like putting out there, and to pull something like that together. I always warn

people around me, “I may not be the most positive person you know the next day” but, it’s not that I’m a negative person, it’s just that I’m just, you know, It’s got to be a roller coaster or you can’t get to that high. You know, you can’t get to the level you need to be, to be on all the time. I

mean I’m sure you know with talking…

Andrew: Yeah, I’ll tell you where I felt it. I, I can think of a few specific situations but I’ll go back in time to the Bradford and Reed days and tell you that there was one time I left the office, went to the other room which was my bedroom, in the house, and I just threw myself on the bed, lights off and I don’t know if I cried. But I should have cried. I was just feeling so bad because I tried every day to get this one woman, Susan, to sponsor my site.

Frank: Right.

Andrew: And I couldn’t even get a call back, and I tried everything, saying “Hey, I’m calling from Bradford and Reed, I’ve got an important call for you, my name is Andrew” you know…

Frank: Yeah.

Andrew: like mysterious but maybe it sounds urgent ‘cuz it’s Bradford and Reed to working the friend angle and she just wouldn’t call me back and I just felt like I can’t get these sponsors…

Frank: Yeah.

Andrew: and before that, when I took my business plan that I wrote so neatly. I mean, if you take a look at this business plan, it looked beautiful. No one, gave me any money, but all these people who like, people who believed in me for years …

Frank: Yeah.

Andrew: would say, tell me if there’s anything you ever want to do and so when I went and threw myself in bed.

Frank: Yeah

Andrew: And you know what happened after that? I don’t know that specific day, but…

Frank: Yeah.

Andrew: somewhere she must have been talking internally about my proposal, because within a day or two, all those seeds that I planted actually paid off. I mean they blossomed…

Frank: Yeah.

Andrew: And I ended up getting her as a sponsor, millions of dollars in revenue from that moment…

Frank: Yeah [??]

Andrew: But that low moment? I still am ashamed that I gave up and went to the other room out of frustration and…

Frank: I don’t think you should say that I think that’s human…

Andrew: Tell me about your frustrations.

Frank: that’s human nature, I mean you can’t, you just …

Andrew: When, when did you feel so low that you, depressed, threw yourself on the bed and, and threw yourself on the bed and said, I can’t make it. Maybe I’m done here. Did you feel that way?

Frank: Even last year, at the end of our year, we had a really long tour man, I went to twenty cities, you know, ongoing. I’d say by the end of last year we were just going on fumes. I have to admit, like some of those days, especially even on the west coast to go and do an event and then take a break for a day and then do an event a day later and then come back and do an event 2 days later, that’s not enough time for the dip.

I wasn’t back up to where I needed to be, so on that situation I worked with people like my partner Jen. I’m like Jen, we’ve got to talk each other through this. It’s the same with her.

Andrew Warner: So you went to Jen. At that low moment you said, you have to talk me through this. You didn’t say, hey you know what Jen, maybe it’s time for us to give this thing up because it’s too exhausting.

Frank: Of course I said that.

Andrew: You did? OK.

Frank: No, I didn’t say that.

Andrew: You didn’t?

Frank: You have those moments where you’re like, you’ve got to help me get through this because I need to be on.

Andrew: What did Jen say then to help you get through that?

Frank: We just talked through all the positive things. I mean, you look at what all the good things are. You’ve got to be grateful for the things that you have versus looking at the bad things.

Andrew: It sounds like you look around and you say, well I’m exhausted, but I can actually put on all these events and people will show up. I’m exhausted, but we did have a better 2011 than we did 2010. That’s the way it is, and it’s her job as a co-partner in this business to perk you up and you do the same with her.

Frank: Right. No, it really is.

Andrew: Do you ever feel like saying, you know what, I’m the guy who launched this, she came in here and I’m going to her? She’s supposed to come to me for trust, for confidence. She’s supposed to come to me for belief in this and if I show vulnerability to her the thing is done.

Frank: Yeah, I guess it’s an interesting relationship. I think everyone has their people they can turn to in that situation and she’s one of mine, so I think at the end of the day it’s just a matter of thinking the positive and I try to do that all the time, but every time that you kind of come to that low there could be negative thoughts.

Andrew: I found in my life that because of those issues, because of those big challenges that almost broke me, I become better. So for example, after being turned down by Susan for months, even though I had friends who suggested that I talk to her and I used them and even though I was persistent and I failed and failed and failed, knowing that I could still be so humiliated on the inside and still persevere makes me feel like I could persevere even if no one is watching this interview and even if you think I’m doing a crappy job here.

Frank: No, I think you’re doing a great job.

Andrew: Thank you. But even on days when I know I’m doing a bad job it makes me feel like, well you know what, I somehow won Susan over and I got that deal and maybe back then too when I thought I was failing I was actually succeeding, so maybe when I think I’m doing a bad job in the interview I’m actually succeeding in some way that I’m not aware of by maybe becoming better at knowing what not to talk about. Do you find that?

Frank: Yes.

Andrew: That because of those challenges you do become better?

Frank: I think you get better if you can just get over that little bump, like get to the event, talk to people, see that companies are super excited to show their stuff, or they just met this other person that is their new co-founder now. There’s positives that come out of every experience like that and it’s just every once in a while you hit those bumps and it just happens and I think you need to understand as an entrepreneur that that’s going happen and don’t give up and that’s the key, it’s just be patient.

Not every day is going to be sunny, sometimes it rains. It rained at South by Southwest. It rained on our day. We’ve got an outdoor area, what are you going to do? Nothing. Am I going to hide in our hotel? No. I’m going to go show up and obviously be happy that everyone is able to get together and were there. You’ve just got to push on through and I think to go back to your same point about sponsors and advertisers and things like that, some of the folks that I’ve been talking to for 6 years are finally coming around.

It takes a long frickin’ time to build a business. I mean I know a lot of people want to have the quick win and get their funding and grow to a bazillion people and it’s going to be a parade down the street and that’s not what’s going to happen necessarily. Especially if you’re bootstrapped and you’re doing something that’s unique. I don’t know anybody else that’s crazy enough to go to twenty cities last year and host events everywhere, you know what I mean?

Andrew: And show up at every one of them.

Frank: Right. But from that learning experience we’re going to basically change our business a little bit so that I think physically, I don’t teleport, I can’t be everywhere, so we’re going to have to change and that’s just something we’ve learned and we had to learn it hard way by doing it one way.

Andrew: I’m going to come back to the narrative in a moment. I’ve got to apologize to all the people who are listening because I’m so lost in this stuff, but we’ll come back to the narrative. Tell me about learning. Beyond experiencing and suffering on your own and then figuring out a solution, when it’s time for you to learn from other people how do you do it? How do you arm your mind when you’re preparing?

Frank: So learning from other people, I just believe in a lifetime learning. I learn from a lot of different people and I don’t necessarily turn it on and turn it off it’s just I’m constantly curious in asking people questions. It may seem like I’m doing it because I don’t know or whatever, I don’t really care.

Andrew: Give me an example. Who do you talk to? Do you talk to Mike (?) at (?) and say, “Hey look you’ve done this event now and tell me what you figured out that I need to do?”

Frank: I would do that, yes. I haven’t recently.

Andrew: Give an example of something that you learn that way.

Frank: What’s that?

Andrew: Do you have an example of something that you learned that way by reaching out to someone else who’s doing an event. Maybe, from the early days.

Frank: Yeah, let me try to think about that. On the event side not as much, I think the content side is something that’s new and I think, I’ve obviously done writing and blogging for a long time, but growing a team and growing a (?) staff, I reach out to folks that have done it.

Andrew: All right. Let’s come back to the writing then. I’m going to ask you about how you learned about that, but we’ll come back to it in chronological order. You do your first event, things are going well, it’s time to do another event. How do you do it? Sorry, you know what, obviously you do another event that’s not as significant as what’s the next big milestone for the events? When do you start to charge and when do you start to bring in some revenue from it?

Frank: Right. So what we started to realize is in Chicago we were hosting events and getting like 1,200 to 1,600 people signing up for them, which is a lot to manage and try to find venue’s. It’s almost like a necessity we had to start figuring out how can we streamline this a little bit, get it down to a number we understand. So we started charging marginal fee, $10 for a couple drinks and entry.

Andrew: Was it hard to charge for the first event because there’s a sense at first that it’s a community, I’m trying to build a community together and by the way guys, pay up. That’s the hard thing to . . .

Frank: It is. It’s scary to do that but at the same time it was something that, I think we needed to do it so we could understand who was going to show up and manage it better. We were getting a lot of feedback, well your venue’s not big enough, you don’t have enough space. We’re like yeah, there’s a 1,000 people here and this venue doesn’t hold that, we know that. So on the event side it was very much trying to figure out how to streamline these events and make them better.

Andrew: So, how does paying make it better? It gets fewer people to show up, true, how else does charging make it better?

Frank: Because people have skin in the game. When they have skin in the game you know if they put in their $10 they’re probably more likely to show up and participate. So I think by doing, it weeded out the folks that were just there for free drinks and made people want to come because they wanted to learn from these companies. They wanted to interact. They wanted to be a part of it.

Andrew: OK. Actually, I noticed that too. I used to do events too. I don’t know how many I freaking got. My idea was I was going to do these events and they were eventually going to lead to mutual learning. I never got to the mutual learning because I never explained to people that that’s the vision behind these events and so what I ended up doing is more events thinking that eventually we’ll get to the next step and do more events meant contacting people like you who I found out about and saying, “Hey, how do I help you get to have a cocktail here to LA?”

And then I said well I need my own invitation software. I got way, way off track. What I did find when I was charging nothing for those events, people would just talk about how it’s a free drinks event? Go there because you’re going to get free appetizers and they’d forget about the mission which in your case you made a lot clearer, it’s to help shine a spotlight on these entrepreneurs and their start-ups. All right, so you start charging, what about going after sponsors? How do you start bringing in those sponsors?

Frank: Yeah. So we actually started doing that right away trying to figure out how we were going . . . because they’re free, early on they’re free events so to begin with we were looking for sponsors trying to figure out how we could offset the cost because we we’re running up some big tabs with these, thousands of people showing up or whatever. So we kind of divided and conquered. My co-founder, Eric, took over a lot of the sponsorship stuff and I took more of the, let’s figure out how to get this thing out there more stuff.

Andrew: Do you have some tips that you learned from him that you can share with the audience for getting sponsors?

Frank: He literally met with a lot of people. He did a lot of in-face meetings and anytime he did he talked about what we’re doing.

Andrew: He met them through his work?

Frank: It wasn’t through his work as much. It was more, he was in Chicago and doing a lot of coffee’s and things like that. We both did it. We actually got a lot of people to reach out to us after the first event. You know the first couple of events and started getting interested in what we were doing and one of the big ones was Mid Phase was turning into Single (?) which was a local Chicago hosting company and that was in 2006ish time frame. Four, five months, a few years later they’re now an Inc., 500 company so it’s like they were seeing the trend happening. They were supporting what we were doing and through that helping to shine a light on what they’re doing that through that, trying to line up what they’re doing. You look at some of our fist events, the single hop frog was everywhere.

Andrew: When people find you through events, how do they even know? How do they know to ask you to sponsor? Why do they ask you to do it? I found it, yes, I get most of my sponsors on Mixergy because people who watch end up sponsoring, but that didn’t happen regularly enough until I put that link at the top of the page that said ‘sponsorship’ where people can sign up, but asking for the business that way helped me get it.

Frank: We have that on our site. Back then, I don’t think we were as smart about it, to be honest with you, we’ve learned a lot. I’d have to say it’s been a learning experience for the last five and a half, six years. I think putting that link on there does help and it obviously creates a place where you can manage who’s requesting different things.

Andrew: So putting the link helps.

Frank: Yeah.

Andrew: My understanding is that talking to other organizers and sharing their sponsors helped, true?

Frank: Yeah, in some cases it does, depends on who you’re talking to, sometimes they’re not as open.

Andrew: Right, sometimes they’re not as open, but often times they are. I’ve helped interview entrepreneurs get sponsors. The fact that you worked at AOL at the time, that helped you get AOL?

Frank: Sure did. They saw the benefit in connecting with early stage companies and they saw the benefit in using the events to also channel out of their brand and market their brand. We did some things with AIM, we did some things with straight up AOL and some of the things that they were doing when they were launching products.

Andrew: That’s something that I found when I was doing events. I remember sitting down with someone from User Voice and saying, ‘I want to learn how you guys decide to sponsor. Why did you decide to sponsor Mike’s events?’ for example. They go, ‘Oh, Mike works with us. He’s good friends, of course, we want to help him out. So this is our way of helping out a guy who works for us.’ What I noticed was that a lot of guys that were succeeding with events, worked for companies that were sponsoring those events.

Having that in is a big help and when I’ve talked to people who run companies that sell to enterprise, launching a company where your first client is your past employer is an easy way to get that first credible customer on board. That’s why guys will sell to Microsoft after they leave or to Google. You find the same thing for you?

Frank: Found the same thing and I think AOL’s benefit, I guess, in marketing as well as hiring, they were trying to hire people, so they love to go to our events to try to find great developers. Then through the events, by doing events in the space, Microsoft reached out. So Microsoft BizSpark has been a big supporter for a long time.

Andrew: I see, and they were just on the market looking for events like this?

Frank: Right, exactly. Obviously, in Chicago we were the biggest thing happening in that space and we’re interested in more than just the coast, we’re interested in connecting with these folks. I think in 2008, through BizSpark, we helped sign up the most start-ups for the Midwest in 2008. We were helping along the way to meet their goals which were, in that case, trying to get startups involved with their BizSpark.

Andrew: So, in that case, it was a measurable goal that you were able to help them to achieve. They were trying to find startups who would sign up, basically, for free software because they wanted these guys to build on Microsoft software.

Frank: Yes.

Andrew: OK. What about this? The usual suspects. Any business that has sponsorship, there’s a list of guys that is just easy to get. What can I come up with? You know what? I’ll stick with this. If you’re doing tech events, the local law firm is the easy get because a law firm has money, all they need is a couple of clients, and they want to raise their profile and they use this sponsoring. Did you find that was true for you guys, too?

Frank: Definitely, it’s also a double-edge sword, if that even exists.

Andrew: Why?

Frank: Because when you start locking in service providers like law firms, or whatever, you’re only going to lock in, probably, one.

Andrew: Right, so you can only have one law firm, one accounting firm, I see.

Frank: Right, because you can’t just have them all be there, they don’t like it.

Andrew: Back to sponsorship. How did you figure out what to charge?

Frank: I kind of let the market decide. We started with a certain level to see what people would be interested in and then it went up from there. You kind of look around the market, as well, you look at conferences as a base but, obviously, this is not, in a lot of cases, a conference, although we have a speaker series rolling out soon across the country in a couple of different cities. When we do our conferences they have a total different sponsorship levels.

Andrew: So when you were looking, did you e-mail people and say, ‘What does it cost to sponsor?’ and then look at their prices.

Frank: We started based off of what the cost structure was to do the events and then worked backwards from there.

Andrew: If it takes $5,000 to do this event, maybe we charge to sponsors $2,000 each and the rest a couple of hundred.

Frank: Trying to keep a lower barrier of entry for people to participate I mean because we do this in a lot of different places, and there are a lot of places that charge a ton for different types of events, so we wanted to be, I don’t want to say economical, but sometimes just very accessible for people.

Andrew: All right. We talked earlier about two big milestones before the interview started you told me. The first big milestone was doing the conference.

Frank: Mm-hmm.

Andrew: How are you doing on time, by the way? We’re going a little bit over. You’re good? OK.

Frank: I’ve blocked out the last two days because it’s [??], so if you see a little gray under here, or not gray, dark circles or whatever …

Andrew: Thanks for doing this interview. I know when you get back from a conference after especially when you work as hard as you do, you say, “You know, I’m going to take a couple of days and not have anything on the agenda, not even have to shave,” and here you are. Not only did you have to shave, you had to put on a clean shirt and come on camera and hang out with me.

Frank: I appreciate the opportunity. It’s fun to talk so …

Andrew: Thank you. So the conference.

Frank: Yes.

Andrew: Is there more money in conferences than there is in evening events?

Frank: It depends. I mean if you do one big conference, Super Bowl kind of thing, and you’ve got the attention of a lot of people, I mean those can be real profitable. Look at like TechCrunch50s of the world or whatever. They’re a million-dollar-plus events, right? So it just depends on what you do. I think we end up scaling our conferences almost like our mixers as a conference across the country, so it’s obviously more work and probably more overhead. Oh yes, conferences bring up a different cost structure because you’ve got now bigger venue costs, longer duration. You got food which is always, like, ridiculous, and yes, so it just adds, and then travel, like, everyone getting there and everything. So it just adds a lot more overhead to the whole thing, so you then have to mark everything back up to make that overhead, you know …

Andrew: So what happened at this conference that made you feel like this was a big milestone for us?

Frank: It was actually very community-driven the reason we did it. It was like it seemed like the right next step for what we were doing, and so we had a conference in May of 2008 in Chicago. At the time, it was just called the Tech Cocktail Conference. We’ve since re-branded it and called it Startup Mixology because it was really, the concept was break down every ingredient that goes into starting up and how to run a business. So we take different speakers for each different category and let them just talk. In some cases, we had a few panels like the legal panel which we brought a bunch of lawyers together to talk about how to start up, what are the things you need to know, things like that, but the reason it was interesting was that things were still really booming with what worked well and exciting and people flew in from different coasts to come to it. But at the time, we had folks locally like Dick Costolo who is the CEO of Twitter, or at the time, he was the CEO of FeedBurner and they just sold it to Google. We had…

Andrew: What was it about the conference that made you feel like we just took our business to the next level? Was it that more revenue came in, more speakers, more guests?

Frank: I think it was just the fact that it was very aligned with the goal of amplifying, and people were really excited about what was happening.

Andrew: And so you were looking back at the conference and saying this amplified the community way more than anything else?

Frank: And what we were doing and it did it on a more of a national level.

Andrew: OK. Where before, people had to be in Chicago or D.C. or some of the other smaller cities that you were doing this in, now it’s a national event. Anyone should be willing to show up to this thing.

Frank: Right. We had people coming from all over to attend and speak, and I still get mentioned. Everyone is all, like, “Yes, you know what? The first conference I went to was this and that really was what made me decide to do what I’m doing now,” which is totally different than what they were doing then, you know …

Andrew: Because of the conference, they changed what they wanted to do.

Frank: Right. It was a turning point for a lot of people, and if you look at, like, who we had brought together back then, it’s just like an all-star cast but no one knew it. At the time, it was kind of like people were still kind of getting leery of these people, so it’s interesting. Like Brad Feld was there.

Andrew: Brad Feld?

Frank: Brad Feld, Dick Costolo, Micah Baldwin, Mike Macadaan. Obviously, a lot of these folks are friends, and I obviously reached out to them to get them to come out, and obviously, we had a great time, but it was interesting. I mean and then we had the mixer afterwards, and companies like crowdSPRING demo’d at it, Edmodo, which ended up now has funded by Union Square Ventures and it’s growing like crazy in the education space. Gary V was of course there because he had spoken at our conference, company called The Point Demoed. It was turned into Groupon.

So, it was a big kind of turning point to have all those people at our event during the day and then coming to our mixer for afterwards. The ironic part was that both Eric and myself were still working full time. So we were able to do this while working full time. And it was a heavy list. So we didn’t do it the next year because we were like, wow that was crazy hard. We did it but hopefully people saw that and could keep that going and kept doing the mixing, so. But as far as like…

Andrew: How profitable was that?

Frank: That’s a great question. It wasn’t like ridiculous profitable. I have to admit. I think we probably cleared, you know, 10 grand or something. Because it was just not even..

Andrew: 10 in revenue.

Frank: Yeah. But that was to try to help us, like keep going throughout the year.

Andrew: And profitable what would you say it is, what do you think it was?

Frank: It wasn’t a lot.

Andrew: It wasn’t. Less than two thousand.

Frank: Probably. Yeah.

Andrew: So let me ask you this. Everyone keeps telling me that conferences is where the big revenue is. That look at Tech Crunch, their making the big money from conferences. Andrew, you should be mixture of conferences, you’re going to rake in the cash.

Frank: Yeah.

Andrew: I talk to several conference organizers. I’m not seeing that.

Frank: OK. So to step back I think the reason that, there’s huge opportunity, right? Like you got, you bringing all those people together there’s an opportunity. I think the hard thing about it is that you’ve got to sell a vision like especially the first time.

And so the first one is not going to be what it’s going to be a few years later. You’ve got to going in understand that you’re going to have to do this over and over and over. I think that’s where we kind of messed up a little bit. I mean, we didn’t do it the next year. I think that if we would’ve done it the next year, we would have done a lot better. So we brought it back in 2010 as Startup Mixology. And did it in Chicago, in we did it in DC last year Startup Mixology. And you’re starting to see it kind of grow and people get aware…

Andrew: And so revenue grows and profits grow from year to year. Why? What do you get the second and third year that you couldn’t do the first year?

Frank: It’s with anything. I mean, you’re selling a vision the first year and then the second year you have actual pictures. I mean, it’s that clear.

Andrew: So people can, I see. So they can say look this guy was there speaking.

Frank: Right.

Andrew: And then people attend it. So you’ve got the word of mouth and it just continues to build. So we did something in DC called DC [?] that you were at. You interviewed Ben at. Ben [Dwalla].

Frank: Ben Dwalla.

Andrew: Yeah. And you know, the first year we did it, it was very similar to the first year we did it our Tech-Cocktail night, you know, our Tech-Cocktail conference. Like bringing all these people together. We did five days of programming and trying to figure all this stuff out.

Last year we consolidated it and it was just overall a better experience. I think you just learn. And then obviously we did a lot better with sponsors. Not that we did bad the first year. But it just, it takes time to sell the vision. And for others to see it and see the opportunity and things that they can do with it.

Frank: When you say things that they can do with it, what do you mean? Like sponsors suddenly discover what they could do?

Andrew: Yeah. Yeah, so for example. Yeah so sponsors.

Frank: Give me an example how a sponsor was able to do something more with the second one than with the first.

Andrew: The first for example is DC, Ford was the sponsor.

Frank: Ford?

Andrew: Ford. Yes.

Frank: Way to go, man. OK.

Andrew: Thank you. So they came out, they didn’t [?] the first year. Second year they did. And their focus was the Ford focus. And a lot of the events they were getting people to do test drives. It seems a whole activation aspect. But you don’t really, I mean, as a conference goer it’s not like in your face that you have to drive a car whatever, if you want one or two. But it’s just ultimately, they had a Tweeting cake for our closing party. That you could literally tweet the cake. It was a Ford focus cake. They had the Ford focus on its face. You could see now it’s a lot more clear what this is and what they can do.

Frank: Right.

Andrew: So, others are obviously going to see that and want to participate.

Frank: All right. And some other thing happened in 2010. Another big milestone. Do you know what I’m talking about?

Andrew: Yeah. That was when I dove off an entrepreneur diving board. Pulled the band aid off of what we were doing. Because what we had learned is that we couldn’t sustain this as a full time thing. I was doing it on the side with Eric for a long time. And it got really hard. I mean obviously there was some tension. We were working our butts off at our day jobs. And then having to like do this on the side. Something that had grown and scaled itself rather quickly without any funding or anything. So there was a lot of late nights I could say.

So we decided, in 2010 I decided there was an opportunity for me to leave AOL. They were asking for people to raise their hand as they spun out. I said, you know, that’s a great opportunity for me because they’re going to get a runway and I’m going to be able to do whatever I want.

Frank: You mean they were giving you money to buy, they were buying out employees. Saying take this money if you’re going to leave.

Andrew: Right. And he’s saying, take this money if you’re going to leave.

Frank: Right. And they were trying to get about, I think, I forget the number, it was like 5,000 people or something to raise their hands and I was like, “Sounds good to me.” I had built products for awhile there and done a lot and it was a great experience but I couldn’t keep doing this on the side, the Tech Cocktail stuff. It was going to end up either dying a slow death or something and I was just too passionate about what it was, that we were doing, and it couldn’t go down that way.

So I reached out to Eric and said, “Listen, I’ve got this opportunity to leave. Do you want to do this full-time?”, and he was just at a different crossroad in life, getting married, in school, getting his M.B.A. at the University of Chicago was not an easy place to do that, wanted to kind of settle down, had just bought a condo and just wasn’t at the same point and wasn’t as passionate about doing it full-time. So we actually worked out an agreement. He just kind of said, “Listen, if you want to do this, do it, and I’m totally supportive of it, I just can’t do this full-time. It’s not the right thing for me.”

So I just went out and started doing it on my own. I actually did it solo for a good first three or four months and then realized, “This is really hard. I’ve got to pull some people in.” I pulled in Jen, my partner, to help right the ship and get things going up on the operations side and continue to grow the team and manage the team. I’d say the first year was probably the bumpiest. I mean, we still did a ton of events and I did a lot of them myself. It was hard. I have to admit, it was really hard.

Andrew: When you were doing it by yourself?

Frank: I have to say even the first six months of it was like shoestring budgets and if I didn’t have that runway from AOL, I don’t think I’d be able to do what we’re doing today. I really don’t.

Andrew: How much money did you get from AOL?

Frank: I think it was about three or four months.

Andrew: Three or four months of salary.

Frank: Yeah.

Andrew: And you were doing what? You were doing over $150,000 a year in salary from them?

Frank: Yeah, I’m not going to comment but it was comfortable, very comfortable.

Andrew: You know, by the way, there are a couple of reasons why I keep asking about the money, the first reason is because I think it gives a sense of where, and I don’t blame you, by the way, for not answering because I understand the privacy around money, but I think it gives us a sense of how much you had to work with and what you were able to do with it.

The other reason I ask about money is because, even if I get a “no” on it, I just get to make a point that revenue and money is important. We’re living in a world where we can talk about design and everyone loves us for it. We can talk about community and everyone loves us for it. But, God, if you have design and community but there’s no revenue coming in, you can only last for so long before someone pulls the plug on you and you can say, “Yeah, maybe I’ll sell it before that happens.” Terrific. Look what happened to Delicious, they sold before they were able to bring in revenue but eventually they had to shut down. If there’s no revenue, there’s no incentive to continue building it.

So I’m just here to say, I think the revenue is important and I let the entrepreneur either say the answer or not. I let them even beat me up and disagree with it, but I do want to at least bring it up in these interviews and not shy away from it. And, thankfully, because I’ve been doing this for a long enough time, people accept that I’m going to ask the revenue question without being insulted by it. Some guests are insulted, which is fine. I’m OK having insulted you guys, but for the most part, people know where I’m coming from on it.

All right. So you still, even though it was tough, you mentioned it to me in our pre-interview as a key turning point, that things got better, bigger, more meaningful after you went full-time. Why does going full-time have that kind of an impact?

Frank: Well, you realize that what you were (?) for on the side was not maximizing what you could do so this was just this open field that you could just be like, “Wow! This is where we should go with this.” So it took us a little while to kind of meander to the point where, “This is what we really need to do.” And, obviously, we had been working on it for a little while, but it’s been very iterative is like what we’ve done and how we’ve done it. So I was just super excited. I had a lot of energy to take this on. I don’t know. I think there’s just that passion to be able to do it full-time that made me super excited to be able to take it on and, literally, wear pajama pants if I want to everyday.

I’d been working for bigger companies for awhile and, yeah, I was getting paid a lot and I had the comforts. I used to take a private jet from Virginia to New York and back on the same day. We don’t have that anymore. That’s not even an option. So you got to the point where you had to be really creative and scrappy as to how you’re going to get things done, trying to maintain the same level of lifestyle, so I think that’s the most interesting thing. I’ve been working at a big company for 10 years, probably, and so when you get in that comfort zone and that pay check and everything else. And 401k and all that kind of stuff. I threw all that away and I was like, you know what, this is the only time I’m ever in my life going to be able to do this. I was excited to take that dive.

Andrew: So, it was a dive that you got excited about. Because you were doing full time what you were passionate about. What else?

Frank: Exactly. Exactly.

Andrew: What else? Was it also that because of that you were able to focus more and not get distracted? Was it that people knew that you were more committed to it? Was it that you had no place to escape when things got rough? You couldn’t say, hey I’ve got to do some work, so I can’t concentrate on this problem? You had to concentrate on the problem?

Frank: I think, well just, you know, you start to realize that you only have so many hours in the day. And if you want to do something right, you need to really focus. And so, I mean, I started doing some things with my partner Jen on the side as well. We started something called Shiny Hard Benchers. And we built some products. Right after we left AOL. One was a gratitude journal, of all things. So we wrote this gratitude community. It’s still out there, as I found out, there’s soon to be an android out. You know, tens of thousands…

Andrew: I noticed it out there, actually. I wanted to see if it was around and how active it was. And I went to a [inaudible] up here right now.

Frank: Yeah.

Andrew: And

Frank: Yeah. The idea there is that we’ve been working so hard on building products, that you know, we liked. But it was an idea, that was like, we want to get out of this corporate environment and build something that we really felt good about.

So like, how can you argue with something like gratitude? You’re going to see someone posting something that’s like, wow I’m thankful for, you know, the sunshine on my ninetieth birthday. You know, like, wow, first off, you’re thankful that you’re 90 but also the sun shining and you’re on our site. Like that’s like, how did it even happen? You know, like, that’s amazing.

So to see things like that posted from around the world was something that really made us feel good and ultimately crazy places that we still posted things. You know, like, so I keep a private journal because I don’t want to share with everyone, but I also have a public one. And there’s, you know, a number of people that do the same. But to see that continue to grow, now our next day is like we have to get some more people on that. Because it’s starting to get to the point where it’s a lot of [API’s] and things have changed. It’s pretty launched. I mean to get those things kind of changed out because…

Andrew: I see more developers to work on it to make sure that it’s up to date.

Frank: Yeah. You got it. But it’s still, it’s something that we’re really passionate about. I mean, there’s no business model in mind other than we wanted to create an amazing experience for people that want to share their gratitude.

And so we did that but we realized we can’t build that as a business and Tech-Cocktail as a business at the same time with the same capacity. So we doubled down on growing Tech-Cocktail. And I pulled Jen away from gratitude. Which I feel terrible about. But it’s been a great thing.

Andrew: Sorry Jen.

Speaking of doubling down on Tech-Cocktail, I went to Somewhat Frank and the post I saw at the top is, hey I’ve been posting here just about every day for years and I know that you guys have come to trust and I love this site. But I’ve got to focus more on Tech-Cocktail.

Frank: Yep.

Andrew: So now I’m going to do all my blogging on Tech-Cocktail. Which must have been a big move for you.

Frank: That was a big move. Yeah. Because that’s something, everyone kind of gets, you know, you’re personal brand you know, is a pretty big deal.

Andrew: Yes.

Frank: So to make that decision, it’s one of those things that, you know, was a tough decision but I think it’s the right thing to do. Because you can only focus so much of your attention on like, (___)

Andrew: Gary [inaudible] was on here. I asked him how he went from being a guy who was doing a small wine show.

Frank: Right.

Andrew: That, you know, few people knew about, to being a guy who was on Conan, on all these T.V. shows and a successful author. And he said, back then being on Somewhat Frank raised your profile.

Frank: [Laughs]

Andrew: I swear. You can go back and listen to one of the two interviews that I did with him. It’s in the record. The official record of the internet.

Frank: Oh.

Andrew: And he said being on Frank’s site elevated my profile with the community of people who are important to me. And as important to my growth. And as a result of that more people discovered me in any way things took off from there. So I understand the movement.

And so that’s one of the reasons why Tech-Cocktail is doing well as a content site.

Frank: Mm-hmm.

Andrew: But what else? How did you grow between March 2010 and March 2012? You and I talked before about the growth, what was the growth in traffic as a result of the content?

Frank: It was 900%.

Andrew: 900%. That means nine times more traffic coming into this site.

Frank: Yeah.

Andrew: How many hits, how many unique hits do you get on your site per month now?

Frank: Right now it’s around 150 thousand.

Andrew: 150 thousand a month, unique hits. Why do you have to do content? I remember you and Jen were over at our place for dinner. And you were talking about how you were stressed a few hours before because you had to be one of the first people to publish, I don’t know what, an article on the new I Pad. Or someone had picked out. I go, why do they need this agita, why do you need the agita of doing content in addition to doing [inaudible].

Frank: Yeah. So we’ve come a little further since that meet. So, that’s what I’m saying, it’s been a learning experience. It’s gone like this, you know, it’s not a straight line. There’s no way that I can say it is. But the content is really to help entrepreneurs and continue to tell the story that’s happening in all these places and so.

Andrew: How does it help your business? I mean, you want to help entrepreneurs, great, but you’re still very focused on growing Tech-Cocktail. How does having content help you with Tech-Cocktail? And I ask because I know many members that I have in my audience are thinking to themselves, everyone tells me I should do a blog, but I don’t have time for it. Why should I bother? You do it, why do you bother? What’s the business upside?

Frank: The business upside is being able to have a voice in the platform.

Andrew: A voice. What does that mean?

Frank: Well, if you’re not out there speaking, no one’s going to hear you, right? So, you got to have someplace you can do that. It’s not like you can just turn it on or turn it off.

Andrew: I see. So when you have something to say, you can’t get people to the site unless they’ve already been coming to this site.

Frank: Right.

Andrew: OK. And when you have something to say what is it? Is it this iPhone 3 stinks?

Frank: [Laughs]

Andrew: Or no, that’s not what you want to say?

Frank: No. No. No.

Andrew: What are you preparing this platform for?

Frank: Well, it feeds itself. So it’s like our events, we have companies that participate, and entrepreneurs that participate, we cover all those companies online. So, not only are they getting the offline exposure for being at the event, meeting people or whatever. They also get an online exposure.

Andrew: So another benefit of being a part of your world is that you expose them to your growing audience. What other benefits do you get? Ryan Carson of, what was his conferences called? Shoot, for some reason I can’t think of his conferences.

Frank: Carson?

Andrew: Yeah.

Frank: Yeah. So fun, like future of web.

Andrew: Ah. Future of web apps. He had a whole company of conferences. And he said look, I got tired of waiting for bloggers to write about my events, I said if I become a blogger then I could write about my own events. And then people can buy directly from me.

Frank: Right.

Andrew: Did you find any of that, too?

Frank: Obviously, it’s a channel to be able to communicate that. And so we put out announcements. We have a newsletter that goes out weekly or daily or monthly and by region as well. I think partly too, I started as a blogger. I mean, I think I’m really passionate about that still.

Unfortunately, I don’t get to write as much as I’d like to. But I’ve found really great people that do, that are able to. And I still hope, lead up a lot of that editorial effort as far as like, what are we going to write about it. When are we going to write about it?

But to your point about breaking news, we kind of decided we’re not gonna be that kind of place. Even though we still cover breaking news. So like, we’d love to have your story but it’s going to take us a little longer to get the story out. Because we’re going to ask you questions. We’re not just going to publish your press release or whatever.

Andrew: I see.

Frank: So, it’s a little different angled then (___).

Andrew: So, you’re not trying to compete with Tech Crunch on being the first to cover a story about a new star.

Frank: I think they’ve done a great job. I don’t think that, you know, I think that obviously there’s other places that do a great job as well. I mean, yes, we want to tell your story. We’d love to tell it on time when you want to get it out there. But we also want to tell the back story too. So it’s like the more like interesting story of the why and how and how do you do this.

I mean, because I think that’s the difference between what we’ve talked before and now I think now we homed in on what we really are good at. And I mean, that’s been a learning process for us.

Andrew: And what you’re good at is those longer, the stories that take a little bit longer to put together, but that give more depth. The, why did you succeed with this start up? How did you launch it? That kind of stuff.

Frank: Exactly. Because our goals are to be a resource as well. You know, we get all these entrepreneurs from across the country that we have access to and can tell their story and why not ask them the questions that people are interested in.

Andrew: All right. A lot of people fade with their blogs. You grew at 900 percent. You told me before the interview started that you learned a lot over the last couple of years.

Frank: Yeah.

Andrew: Name me three things that you learned, that my audience, that my members can steal from you and go implement on their site. What are three things that you’ve learned?

Frank: Let’s see. On the content side?

Andrew: Yeah. On the content side. How do you grow content? Because if they’re going to build a big business and at the same time go blog because they’re learning from you that there’s value in that. I want them to do it right.

Frank: Things that we learned, I mean obviously, I’m going in the opposite direction.

Andrew: So, you don’t have to break news.

Frank: Breaking news does sell though. And I know if we did that we’d be bigger.

Andrew: OK. So if you’re not going to break news, and I know that too. That if I do an interview with a news maker, I get way more traffic than I get for five other interviews.

Frank: Right.

Andrew: But if you’re not going to do that. Because it is bust your butt, get things done, 24 hours a day type of work. If you’re not going to do that. What else can you do? What else worked for you?

Frank: Just being able to share things that are with a unique angle that others don’t have.

Andrew: Give me an example of a unique angle that you went with (___).

Frank: So, instead of doing, like, say, what just launched yesterday? So even, you know, this is probably something we wouldn’t be able to get access to, but let’s say with Apples launch today or something. We’d want to interview somebody from Apple. But I obviously, that’s not going to happen because they don’t really do interviews. So, you know, we’d want to try to get the back story of how this thing was created. Why it was created, you know, why is it important to you as an entrepreneur if you’re staring a company versus..?

Andrew: OK. So it’s not hey look this is how many, here’s my review, my first review of the iPad 3.

Frank: Right. Because you’re going to see that everywhere.

Andrew: Right.

Frank: Everyone is going to do that. That’s just, like, anybody [??] can do that.

Andrew: So iFixit, whose founder was on here, he takes a new angle with that where what he does is he takes apart the device because his site is all about fixing things and looking inside them. Your unique angle is we’re going to talk about how it helps the entrepreneur or whether it does help the entrepreneur. OK, so unique angle. Tell me what else gets traffic.

Frank: Let’s see. Well, obviously, sharing your stuff across the Web, right? We got a bigger reach through Facebook and Twitter and all these other places because of our use of that, right?

Andrew: But how do you get so many Twitter and Facebook followers?

Frank: You know, that’s a great question. I think for us, it’s been all organic, like, organically grown through the years. I think there is a lot more people quite better at it than us, but we haven’t been as focused on it.

Andrew: What about going daily? You will not take a week off. A lot of people will take a week off of blogging. You go daily, right?

Frank: Yes, we’re daily.

Andrew: Multiple times a day.

Frank: Yes. Probably like five to seven articles a day now. I mean consistency is important.

Andrew: Why?

Frank: I think it’s definitely something people should think about. But it’s actually setting the expectation is probably one of the keys.

Andrew: OK. So you don’t have to be three times a day the way that Frank is. You are saying just let everyone know how often you’re going to show up and then show up when you say you’re going to show up.

Frank: Right. And if you show up, like, weekly and you show up in fours weekly, that can probably generate just as much traffic as if you generated, like, six articles a day because things get lost. There is so much content out there now.

Andrew: What about e-mail? You guys have a big e-mail list. Do you use it to promote?

Frank: I think e-mail is still so crucial because, like, it’s still, like, the first point of contact for a lot of people. I get up in the morning. I check my e-mail. Even though it’s overwhelming, like, you still want to see what’s coming in and get back to those things that you need to right away. But yes, so, like, we do a lot, like weekly, daily, and monthly e-mail newsletters, and we even do it by regions, so, like, if you’re really just interested in L.A. or D.C. or Chicago, you can find out …

Andrew: You can just get. And every time someone signs up for an event, they join your mailing list.

Frank: Right.

Andrew: How big is your list? You can’t say that either?

Frank: Not comfortably. I don’t know. I actually don’t know right now because…

Andrew: Is it over 50,000.

Frank: It’s about. It’s getting in there, yes.

Andrew: OK. All right. It’s a pretty sizable list.

Frank: It’s a sizable list.

Andrew: [??] you told me the number in private but I won’t…

Frank: I don’t want to just give you a specific number because it’s not going to be accurate, like, I don’t know because we haven’t basically included all the people from the South By yet, you know.

Andrew: All right. Let’s see what else we got here. Sponsorship. I can imagine a lot of people in my audience would want a sponsor, and I could also imagine a lot of people in my audience are thinking, “Dude, I got Facebook ads. I can keep track of how many people are clicking from the ad over to my site and buying from me and then returning because everything online for sponsorship is trackable.”

Frank: Right.

Andrew: So what’s the benefit of sponsoring an event where you don’t have that kind of accountability?

Frank: Well, see, we try to make each experience have that kind of accountability, so, like, depending on what we are trying to do, so …

Andrew: So with this bark, you give them the accountability of “We’ll get you people to actually sign up for your thing instead of just look at it online with …

Frank: And in some cases, it’s really hard to figure out what that is because a lot of times, the sponsors don’t even know, like, they don’t want to know. They just want to do it, and you’re, like, well, if you just do that and there is no accountability, how is that going to be successful? Like, there is no … a big one that’s tough is branding, brand awareness, like how do you make sure that it gets noticed, like…

Andrew: People know about it.

Frank: And so we try [??] social experience.

Andrew: What did you do for Dotco?

Frank: Go ahead. Sorry.

Andrew: Sorry. I keep interrupting because I’m worried about your time, and what it leaves me to do is be rude. Dotco, you guys did something for them around branding, and it got them some press. Can you talk about that?

Frank: Yes. So Dotco is this sponsor of our South By event and they were there in full force, and through that, they got seen at our event, interviewed Juan, the CEO. We produced a video series that interviewed Juan and put him out there that got syndicated out to USA Today, so we’re obviously driving attention through that. We had a number of their Dotco companies interviewed at our event, so we continue to kind of drive additional interest.

There is a lot of digital press there, so it’s just kind of an ongoing thing. Our whole thing was to tweet the hashtag #startuplife, so that was social, like, when people saw that, it was on photos and it was on a micro-site that we created and one that they created, so the whole thing was kind of measurable, in a way. So that’s like the Super Bowl of analytics, right, but that doesn’t happen in every city, right? South By is a unique experience and a unique platform. So I think the key then is to work in each individual city with the different folks to find out what they are trying to do. So like in the last year, we did a bunch of stuff with Sprint and they were trying to launch 4G, so we would measure a certain hash tag on Twitter to see if some people participated and we’d be able to measure what people were doing and saying out there about what was happening.

Andrew: All right. Let me say something here, a couple of things, and then I want to ask you a very important question.

Frank: OK.

Andrew: First of all, I found the website for Jex if anyone is interested. I call her Jex, but I think she prefers to go by Jess. She’s very Austin cool. Her name is spelled J-E-X, but it’s Jess. Anyway, it’s I don’t even think you can contact her, but you can stalk her on Twitter and Facebook and connect with her there. The second thing I want to say is Mixergy Premium has courses that will rock your world.

If you go to and you click around you’re going to see that a lot of this philosophy of showing companies how to actually generate revenue is inherent in every course it seems like. So when we do a course on how to build an iPhone app we bring on the guys from FreeApps who generated a million dollars with their apps even though they didn’t code any of it because they went to sites like Elance and they brought in outside developers to code it for them.

I say show me your revenue, show me your advertising, tell me how you generate it and show me how you get these developers to build the apps for you and to be accountable and that’s in Mixergy Premium. What else do we do? If you’re not into coding, let’s see, do I have this up here? Yeah, here. Here’s one of the comments on one of the course that we did that’s on creating content.

Diane says, I’m very shy so the thought of doing videos was scary before listening to this course, and this is a course that Greg Rollett did on how to create a profitable information product. We thought, hey you know what, this is a tech site, but maybe people don’t want to code, maybe they don’t want to build iPhone apps, they just want to create information products like books and videos and sell those.

She saw that and she said, boy this is a little scary, but she goes on to say, after listening to all the advantages of video I decided to take a baby step of recording a product demo video and rather than using my voice I put subtitles and showed only my hands. Somehow once I took that step it was really easy to do another video with my voice included. I did a couple more videos and actually enjoyed doing them, so I’m grateful for the push this course gave me.

So you’ll see that throughout these courses people will start to get progress and you get to watch them as they get progress. This is the course actually on how to create a profitable information product, but now that I reread her comment I can see that Diane isn’t looking to build an information product, she just wanted to build a video to help sell her software it looks like. So there are lots of different ways to use these courses.

They work and you’ll keep seeing other people talk about how it works for them. The reason it works is because I’m not sitting here doing it with my sweater vest here, I bring on an entrepreneur who’s really good at it and I say, look I’ve got a big audience at Mixergy. Lots of paid customers are going to watch you. If you teach instead of just talk about yourself they’re really going to admire you and maybe do some business with you.

All you have to do is come on here and really teach exactly how to do what you do well and in Greg’s case he knows how to build a great information product and how to create videos so he taught that. Tim Sykes was on recently and he talked about how to generate money from a blog and that’s what he did with his business, with

He told me in a past interview that he generated $3.3 million blogging and I said, all right mister big shot, show my audience how they can do it, so he did it. So that’s all at Let me look at the camera and say, I guarantee it and if I raise prices soon I also guarantee that you’ll keep your current price forever. All right. Next, here’s the important question I have for you. You exhaust yourself by going to these conferences.

You go there beforehand, you stay there and you sweat the details and you work with everyone who comes in and you greet all the guests and then you exhaust yourself on the flight back home and then you exhaust yourself by coming here and doing this and still you keep going. How do you, when you’re exhausted, get yourself to keep being productive? Because I see most people, they throw their hands up and they go watch TV and frankly I’ve even done that. So when you’re exhausted how do you overcome it and still be productive?

Frank: Well just this last week is a great exampled. I got back Wednesday from the south, we were there for 7 days, so I did 3 days of prep and then our event and then Sunday, Monday, Tuesday, Wednesday we’re all just out talking to people and people that we don’t get to see because it brings so many people together.

So yesterday was a no-meeting, hold-for-no-meeting day and I posted out there on Instagram and other places that this is a South by Southwest recovery day and I think being able to take that and take that day off and just relax and granted I still was on the iPhone and talking to people and emailing and I think I did a couple of calls, but it wasn’t as intense as what we’d been through last week. So being able to do that just kind of recover and I took a walk outside. It was beautiful here. It really helped today. Right, so today I’m back at it. I’m going to probably work this weekend, like a little bit, to keep things going, right?

So, I think the key is just to be able to understand your body, and understand your mind, and what you need, and listen to it. Like I said, so if you need a break, take the break. Take a break, ‘cuz you know you’re going to still work all weekend, or whatever. So don’t keep pushing it if you don’t have it in you. Just take a little break, get back at it, and then go full force.

I think that’s one of the biggest things that people don’t realize is that your body needs rest, and rest is such a crucial part for keeping you on point. So this weekend is going to be probably a little bit R&R, a little getting back to it, so next week we can dominate. I mean, that’s the goal.

Andrew: All right. Well, that is good advice. I need to keep being strong. When I say I’m taking a break, to not give in to side work, or to side distractions, or to people who say, ‘Hey, you have a whole day off. Why don’t you come and do this or help me with that?’

Frank: Well it’s just, yeah, but then you’re doing work, right? Like you’re doing that . . .

Andrew: Yeah.

Frank: . . . so you almost need to just create your own little environment where you’re comfortable and do your own thing in that environment. It’s different for everyone. I mean, it could be going out and going for a bike ride or whatever, if that’s what you like to do. So just get out of it for a little while so that you can get back in it and come at it 120%, if that’s even possible.

Andrew: All right. Thank you for coming in and doing this interview. The site of course is Tech Cocktail. If you haven’t been to a Tech Cocktail event, you’re really missing out on, I was going to say, ‘one of the best’, but I can’t think of anyone who does better local events than Tech Cocktail. I can’t think of anyone who takes it as seriously and also creates an environment where you don’t have to be as serious, the way Tech Cocktail does. So . . .

Frank: Thank you so much, that’s flattering.

Andrew: It’s true. I mean, you can look around and you can say most people are kind of doing it as a side thing, and hanging out, and maybe it works, maybe it doesn’t. Tech Cocktail works. When I got to D.C., I said I’m going to Tech Cocktail then, ‘cuz I need to know some people around here. And boom, within an hour, I got to meet dozens of people who I’ve still stayed in touch with. Many of them became customers of Mixergy or we became people who helped each other with their businesses. I can’t recommend enough and of course somewhere on there is a sponsorship link that I hope people will, if it makes sense for you, that you’ll go and become a sponsor. Because it is a great event and I want to see it continue to grow, and I know that it’s one of those events where the organizer would take good care of you, because I know the organizer. Frank, thanks for doing this interview and thanks for letting me push you with some revenue questions.

Frank: Oh, no problem. Thanks Andrew, I really appreciate it. This was awesome.

Andrew: Cool. All right, thank you all for watching. As always, go out there, use it, and let me and Frank know how you’re doing it. Bye everyone.

Who should we feature on Mixergy? Let us know who you think would make a great interviewee.