T.A. McCann with Shane Mac

Alright, hey everyone, thank you for joining the Ask Interview series. I'm excited today to have a friend of mine, someone that I look up to, and someone that I'm proud to say I've worked with before, Mr. T.A. McCann. He's the founder of a company called Rival IQ. In the past, he founded a company called Gist.com. He was a professional sailor and won the America's Cup in 1992 and 1995. He didn't win both times, but one of those times. And he's also a mentor and advisor and investor in a lot of Seattle companies and involved with Techstars a lot. So thank you for joining me today. I'm excited to have you here.

Thanks, Shane.

So we always start off the Ask an Interviewee series by using one question to kind of like kick it off and lead it into the discussion and just hear stories from people, you know, that have something that can be helpful to the people listening today. And what I wanted to go to you, you have such an interesting background. I want to take it back. Like back to maybe when you were a lot younger than you are today, even though you're not old or anything, but just take it back a little bit. And the question that I wanted to ask you is, what past experiences do you think have contributed most to your success? And you can take that as far back as you want. And I would love to just hear more of like the progression or timeline of your life and stories around things that you think contributed to things later on that were successful.

Yeah, great. Well, thanks a lot for having me. It's great to be together, so to speak. Yeah, I'll take it all the way back. I started my first company when I was like 11 years old. So I remember printing my own business cards saying T.A. McCann's Grass Cutting and Yard Work, and I like literally printed them on a hand printing press in my junior high school. I still have those business cards. It was really pretty cool. But I started working as, you know, really, really quite young and the sense of driving my own direction and owning my own thing was really empowering for me. I did that for a couple of years.

Who pushed you to do that?

I don't know that anybody pushed me to do that. I think I was primarily motivated by independence and both, I'd say, financial independence. Like, it was cool to have a little bit of pocket money that you went and earned on your own to go and spend however you wanted. So I think I was a little bit financially motivated. I think more than anything, I was motivated by just being in control of my own thing. And from a really, really early age, and whether I was doing my marketing, doing my cool little business cards, or doing the work, I enjoyed both components of that when I was super young. And then I moved into doing the same kind of thing where I was involved a lot, as you mentioned, as a sailor. I was involved with the boats. And so I started my own sort of boat washing and boat maintenance business, and I did that really through my teens.

How did you get into sailing?

My parents had a sailboat, and, you know, we grew up on Lake Michigan outside Chicago. And I always, you know, from time I was a little, you know, little kid, we were hanging around sailboats. And I didn't get into sort of competitive sailing until I was sort of 13, 14. But I was always hanging around boats.

Awesome. Is there something in— like, do you go to college for that? How do you get into competitive sailing?

Well, I grew up, I knew how to sail, and my parents both were competitive sailors, albeit on a sort of a small club level. And one of the boats that I worked on, like taking care of, these guys asked me, they said, "Hey, we race this boat and we would love— would you be interested in coming out and sailing on the boat?" And my mom, I was like, "No, I'm not interested." In fact, I got quite seasick when I was a kid. I was like, "No, not interested." My mom really encouraged me. She said, "Just go try it. Just go try it once. What do you got to lose? You lose one Sunday. Who knows? You might like it." I tried it. In sailing, no matter what age you are or whether you're male or female or big or strong, everyone kind of treats you in a similar way. Everyone is equal. That really appealed to me. It's almost like in a startup. Everybody is equal. It doesn't really matter what you've done in the past. It doesn't matter what your rank is. It doesn't matter this or that. It's like everyone's equal. We're all contributing to the same thing. That really appealed to me at a young age. I felt empowered. I felt maybe older than I was. I went back. We kept getting better and better. I went from one boat to the— which was kind of above average. Then the next summer, the guy who ran the best boat asked me to sail with him. Then we got to be kind of the big fish in the small pond at Lake Michigan. Won a bunch of things there. And so it just kind of went from one to another to another until I got to be, you know, pretty good, albeit in just the sort of the Great Lakes area.

So can you take me from then? So it's like many, I think, athletic careers in general, especially mine. Uh, I was really good at baseball in high school. I came my senior year, I got cut, I didn't make college baseball. The end of sports is my, you know, everything I knew in life is done at that day because I thought baseball was everything. And I think a lot of people in athletics, you never get to the next step. Very few people, 1-2% of people actually go to a college and then, you know, the 0.0001 get to do it for a career. And I didn't know a lot about the America's Cup in general until I met you, or mostly last year being in San Francisco. The America's Cup took over the city and I was like, holy shit, this thing is actually a big deal. And the amount of money and teams and really how few people are actually involved with the actual teams. There's only a few teams and there's only 11 people on a boat. So how do you go from the big fish in Lake Michigan to actually ever winning an America's Cup and being, and, uh, like becoming a professional sailor? Like, what is that? How does that progression happen?

You got— I mean, I got lucky enough for two factors. One is that my parents always encouraged me to go ask, you know, for an opportunity. To say, "Listen, I know I might not deserve this, but I'm going to ask and I'm going to come in at the lowest possible level and I'd like an opportunity to try out for this thing." When I was like 13, I saw this video of the Around the World Race. This is racing around the whole globe. I said, "Man, that is cool. That is for me. I want to do that." I'm just a kid. I'm a kid sailing in the Midwest. I had no plan on how to do it, how to approach it or anything, but it sort of sat in the back of my mind as I got to be a little bit better here or there. I went to college. I got out of college and I said, "Well, if I want to go try and achieve that goal, I better start figuring it out." I literally wrote a letter to these guys that I had met 3, 4 years earlier and I said, "Hey, I don't know if you remember me, but we met back here. I just graduated college on a swimming scholarship. I'm big. I'm fit and I want to go and do this round-the-world race. Could you help me? Could you tell me what I need to know, what I need to learn, who I should who I should get in touch with, because it might be, it was 3 or 4, 3 years in advance of the next race upcoming. Sorry, this was in 2000, sorry, 1990. Okay. So 1990, I graduate college 1989.

No email.

No email, so I write a letter to these guys named Gary Jobson and Buddy Melges, and I said, I would like to go do this thing and achieve it. Could you just tell me what I need to learn? How do I need to get myself on that path to achieve this thing that I wanted to do since I was a little kid? They wrote me back and said, "Yeah, sure, we remember you and we'd be happy to answer those questions for you, but in the meantime, we're putting together this America's Cup team. Would you be interested in trying out?" I said, "Okay." So I tried out. I went to the tryout and they said, "Yeah, not quite good enough." So they sent me home. But they said, "You know, we're going to look at some other guys." And then they invited me back and I was literally like the last guy chosen on the team. Then we went on to win the America's Cup with that 1992 team. It's like being there at the IPO. It's like you may have had a very small contribution to it, but you were on the team and you made it happen. You get the watch, so to speak, in sailing. It was really about the persistence of I had a dream and I wanted to go after that knowing it might take me many, many steps to get there, leveraging my mom or my dad saying, "You know what? Just go try." What do you got to lose? Nothing. And those two things worked out to take me from the big fish in the small pond to a really, really small fish in the biggest pond. And it took me a while to make that step.

So you mentioned you went to college and you had a degree in—

Mechanical engineering.

So when you got out of college, did you have any— you didn't have pressure from parents to say, go use your degree?

Well, I had a job. I mean, I got out of college. I got a regular job. I mean, a good job, entrepreneurial job. I was like an individual sales guy working for a robotics company in the Midwest. I was running my own territory. I was straight out of college. It was still entrepreneurial, albeit I was working for a slightly larger company. But it's almost like if you're in a company now and you think you want to do a startup at some point, you start working on Tuesday nights. You start building your entrepreneurial skill. You start doing your side job. And you and I both talk a lot about doing a side project, and sailing at that point was a side project. I didn't know if it would materialize. I didn't know if I could find the right path to go and achieve it. So I had my day job. Got it. I was doing that. I was learning from it. But I started my side project, which was in this case trying to do the round-the-world race.

And the moment you got the real call, like, hey, you want to be on this team, is that like years of your life? You just practice. It's full-time now. You get paid. What does it even work? How does that even work?

That's it. Yep, you quit and you become a full-time sailor. And in the America's Cup, I mean, it's 6 or 7 days a week. I mean, it's a startup, 6 or 7 days a week for somewhere between 2 and 3 years. And it is hardcore, 6 o'clock in the morning until, you know, 6, 7, 8 o'clock at night. And you're like dead tired every day. I mean, sometimes you're working 26, 27 days out of the month, like just no time off. I mean, you're just busting it hard because Just like a funding round, you could think, listen, the America's Cup is going to happen on this day. The race is going to start on this day. We've got only so many hours to do the best we possibly can to build the fastest boat, the best team, whatever. That's what you do full-time. Yeah, you get paid and they look after your expenses. Just like Google or wherever, they buy your lunch. It's all taken care of so that you can focus all of your effort on trying to be the best that you can.

What happened in 1995?

Uh, so I did the '92 Cup, then I did the round-the-world race '93-'94, um, and then in '95 I joined Dennis Connor, who is probably the most well-known, uh, America's Cup sailor and probably one of the best, well, most well-known sailors, you know, out there. And we were underfunded. I mean, simple as that. In sailing, um, money translates to technology, technology translates to boat speed. And if we create a fast enough boat, anybody can sail it. And so there's all this groundwork that's laid. And the more money you have, the more engineers you can hire, the more tests you can do, the more prototypes you can build. And the more of those you build, you increase your chances of success. And in the case of 1992, we probably spent as much, if not double, of everybody else super fast. In 1995, we spent half of what the Kiwis spent, the New Zealand team. And we were slow. And so we did the best we could with what we had, but technology was slow and the boat was slow. And no matter how well you sailed it, you just couldn't compete. Hmm. And we lost.

How bad?

Well, the America's Cup is always a head-to-head race, so it's called a match race. So you go through a process of elimination to get to the final match. So, I mean, we lost handily. The Kiwis beat us handily in the finals of the America's Cup in '95. And that was the first time that— that was the second time that America had lost it. But it's pretty rare. And now it's taken all the way back to Larry Ellison and his team of Oracle to bring it back to the United States.

That's crazy. So you're done. 1995, done with the America's Cup. No more professional sailing?

No, I was hired after the '95 America's Cup by Larry Ellison. There were 4 or 5 of us from the Stars and Stripes team, which was well regarded as one of the best teams, albeit on a slightly slower boat. And Larry said he wanted to go sailboat racing. So he hired us and we basically built a boat for him and built a program for him and built the guys and hired the team. And we went on to win 5 world championships with Larry. And we were sitting around after winning, I think the 5th of those world championships. And he said, "Okay, well, like, is this it? Is this the end?" He said, "Well," "If you really want to go big, Larry, you got to go for the America's Cup." He said, "Well, what would that entail?" This was like '98, '99 timeframe. He said, "Great." We talked about a budget. We talked about a team. We talked about an approach. He put that team together and it took him, I think, 8 or 9 years to actually go and win the America's Cup and probably $300 or $400 million to go do it. At that time, he was going to step up to the next level. I was fading out of sailing.

And so you're looking at like 1995, it sounds like you were there for a few years after that, right? You have a mechanical engineering degree. How did you turn and end up getting into technology at all?

Well, we were sitting around, I was sailing on another professional team in '95 and it was in Europe and the owner of the team said, "What's going on with this whole internet thing?" And it was when Bill Gates was on the COVID of Newsweek. It was when Netscape was just starting to happen. I mean, the internet was starting to happen. I basically said to the team owner, I said, "I'm kind of interested in this too. Why don't you just pay me like $20 an hour over the winter and I'll go build us a website. Maybe it will be good for promotion or for sponsorship or something and I'm interested in figuring it out." What did you use to build the first website? PageMill.

All right. PageMill?

PageMill. It's awesome. We built the first database on Access. Nice. Microsoft Access is the database and we were using Active Server Pages which is really cool. This is sort of like circa 1998. '96, '97. But we built this website and it was, you know, it was terrible but pretty good. And people saw it and they're like, "Wow, we want one of those." And so we, myself and my brother who is my co-founder, we basically built a side business while I was sailing full-time now, I had a side business building websites. And then pretty soon the website business became the full-time business and the sailing became the side business. Then by the late '90s, I sort of faded out of sailing. I was spending all my time on technology and building technology companies.

Technology in the sense of you were building websites for other people like an agency or a consulting type gig?

Yeah, exactly. With your brother? Yeah, that's right.

Then from there, you went on to actually start a product-oriented software company, correct?

Yeah, that's right.

What was that?

The name of the company was called HelpShare. And it was an online marketplace for questions and answers. A little bit like Jelly, a little bit like Quora, circa 1998.

So 15 to 20 years before.

Yeah, a little bit.

And the premise was just a community you could ask a question and then get answers, just like Yahoo Answers as well?

Yeah, we were before Yahoo Answers, before Google Answers, all of that. So it was—

Is this before Google?

No, not before Google. Google started in '96.

Okay. Because I remember there was a story I heard from one of the founders or the CEO of eBay, and she was talking about, you know, eBay was before people were searching. Like, they would go to eBay directly. And so how were people finding Helpshare?

Well, they initially were finding it because we had done a reasonable job of content marketing. I mean, every question that went through the site was basically being indexed by Google. So if you went to Google or AltaVista at the time—

Lycos, Ask Jeeves—

you would basically do a search and then you'd find, "Oh, here's actually a question and answer." I mean, it's identical in that sense to the way Quora is working today. I mean, Quora has lots of really good natural traffic because they've indexed all the content. So we had that similar sort of model. So people were finding it. That was one way. Two is we built the system initially to be a white label system. So we built it so you could plug it into homedepot.com or gardening.com or lawyers.com because those communities already existed. They just weren't enabled to ask and answer each other's questions. So we architected the product and our distribution strategy or acquisition strategy was really thinking about, let's take it to where the people already are and let's enable questions and answers in those communities.

Is this very much like forums of today?

Yeah, well, forums were actually a predecessor. I mean, forums existed, but the challenges with forums were twofold. One is there was no way to provide rankings and rewards. There was no way to understand credibility. So you ask a question, one guy says, "Make it white," the other guy says, "Make it black." You don't know what to do because there's no way to figure out, like, is one guy smarter or dumber than the other guy. So we added ratings and rewards to the basic model of threaded questions or forums.

It's interesting because you see things 15 years later like Jelly, which they also don't have ratings or rewards and it's just random answers. And I'm kind of like, you know, is this— it needs a little verification layer on top of who this person actually is. But hold on. So go back a second because you started this product-focused company. I understand how you make money when you're in a consulting company building websites for other people. But how are you actually paying for this?

Like, So that was my first angel-funded company.

Okay.

Our primary revenue model was we were licensing that application or that platform to other online communities. So if you were gardening.com, you would pay us a fee to license that particular product.

And you had gardening.com?

We had a lawyer site, we had a small business site, we had an IT site, 1, 2, 3, 4, like 3 or 4 vertical sites that we had sort of licensed it into. At which point we said, "Great, now we've got like real revenue. We have real customers. We've got flow of questions and answers. Let's go raise a Series A, you know, real venture round in February of 2000." It was like the month before the dot-com crash.

Insane.

And then we were hosed.

How much angel money did you raise?

Like $350,000.

And friends, families, investors, who?

Yeah, friends and family, pretty much all. I mean, I had no idea what I was really doing. There was a couple of angels in the Seattle market that participated. But generally speaking, I had no idea what it meant to raise money, to raise money in a strategic way, or anything like that.

And it was just you and your brother?

Yeah, they were the two founders, yep.

And so did you hire like engineering team or did you code it yourselves? Like how was that? What did that look like?

Yeah, Rob did, my brother Rob did all the original coding, but then we ended up building the team up to about 13 or 14 people. So about 3/4, you know, half engineers. Half marketing, customer support, a couple of account manager-y kind of people, one sales guy. I mean, we were building a real company when we basically ran out of money and had shut the company down.

What was that like?

Remember like it was yesterday.

What was the worst part about it?

I think the worst part is that you all believe in a dream and a thing that should exist in the world. One might argue that it should exist in the world because people are still trying to create it. Whether it was Jelly or Yahoo Answers or Google Answers or Quora. So we believed that that thing should exist in the world and that we weren't going to be able to go and do it. We had to stop working on pursuing that thing that we think needs to be in the world. Everybody could go find regular jobs and that all worked out fine. You could go solve that but we also really enjoyed working on the problem together. The team was really solid. We were having a lot of fun together building the thing and working really hard at it but It's sad when you have to sort of break up a team that you've worked hard to put together.

I have a question on this. If you like working and believe so much in what you're doing on the side and you were all in, how did you know to quit and not keep doing it on the side?

Well, I remember sitting with the team when we sort of got the final no from whatever 27 venture capital firms we were talking to. I was like, "Okay, I don't know who else we're going to talk to." We're now well into the dot-com crash. I remember just saying like, "I would love for you guys to keep working on it with me, but I can't pay you anymore. All the money is gone. So I understand if you want to go and get a job. Totally fine. You should go do that." Some of us stayed on for much longer. So my brother and I were the first in and we were the last out. We worked on it for another good sort of almost 6 months probably past when everyone else is gone, still trying to make something of it. At a certain point, like your wife or your girlfriend or your friends say, "Dude, you need to get a job. It's over." I think many entrepreneurs, myself included, certainly at the early stages, they'll keep going because we're persistent people. We believe in the vision and we think, "You know what? Someway it's going to work out." In many cases, too long. In that case, I mean, there's lots of examples of where it did work, but there's way more examples of people who worked on it far too long. And should have just been able to say, "Kill it." So did you go get a job?

Yeah.

I ended up working at Microsoft. So I didn't think that I would end up at Microsoft. I knew little about them, but I thought what I wanted to work on is sort of a company that might be the next stage along. So I was looking at companies that are like 50 or 100 people, kind of Series A, Series B funded companies. And a friend of mine said, "Hey, you should go just talk to the guys at Microsoft." And I'm like, "Why would I want to work there?" Literally, I just wandered around. I'd meet one person and they'd say, "Well, tell me what your perfect job is," and I would describe what I thought I wanted to do. They'd say, "Well, we don't have that, but you should go talk to this other group and this one and this one and this one." What was the job? I said I wanted to work as the intersection of product development, business development, and sales. I like building products and I wanted to be close to building a product. I like business development because it's more strategic. It's like aligning different interests and it's about distribution. I like sales because I like closing it. I like actually having something that has meaningful value where someone will give you money for it. I continued to describe it that way and ultimately ended up working on the Exchange team working on email, corporate email.

When was Exchange— is it a new product? Is it around that time or has it been around for a while?

No. When I joined Exchange, it was $640 million a year in revenue. It was already a big product. I think Exchange, the first version of Exchange were around 1995. Now, we are 6, 7 years into it. It was arguably, they were beating out Lotus Notes, which I don't know, maybe it doesn't exist anymore. Gmail had just really been invented on the consumer side and hadn't really moved into a business side yet at all. By the time I left, it was over a billion-dollar business. 3 years later, it was a billion-dollar business at Microsoft.

So take me where you're at now, 2007, 2006?

2004, I left Microsoft and I started a bunch of entrepreneurial things in and around Exchange. I started a program that would work with venture capitalists to say, "Hey, I need you guys to go build a bunch of products and companies that fill in the voids around Exchange." One of those relationships led to the Polaris guys asking me to come and entrepreneur in residence. They're like, "Hey, that was fun." developing ideas with you, you should come over here and develop your own ideas.

So two things for people listening, because I don't know if everyone understands. What is Polaris, and then what is an entrepreneur-in-residence?

Polaris is a venture capital firm.

In Seattle?

Based in Boston, and at the time they had an office in Seattle. And an entrepreneur-in-residence is usually somebody who has some level of entrepreneurial success, or in my case, failure. that they hire and give a small stipend to with an expectation that they'll develop companies, and the venture capital firm will get a first look at that company with no obligation to fund it, but their opportunity to watch it develop before everybody else gets to look at it. And the entrepreneur's opportunity is that they're working with a venture capital firm already so that they have a higher likelihood of that idea being funded.

And, and you get a salary. You're, you're an employee of the venture capital firm.

Small salary, enough to make your house payment, buy beer and pizza.

Yeah, yeah. But, so that, is that, it seems like the dream for, if I'd never done a startup before, or, like how do you get that gig?

Well, you get that gig, generally entrepreneur residents are people who've already been successful at starting a company. Got it. And I was the odd one that, you know, my company had been a failure. But most of them are successful. But most entrepreneurs, I mean, the dream is to start and run good companies, not to hang around and think about starting companies. So it's really just a sort of a place of, um, an opportunity to study, to focus, so that, you know, they're like, you're not doing your day job, you have enough time to work on new ideas. Personally, I find it, um, I don't like that model. I would much rather have something I'm working on with a significant amount of my focus and have a side project. So my— for me at least, being in a room by myself with just myself and a whiteboard is not as good for developing ideas as it is being out kind of in the community, because I never know how long it's going to take to develop an idea. You can't force it sometimes. Sometimes you have to wait for the market, sometimes you have to wait for the team. And like, you can't just say, like, great, here's 3 months, like, go find your next idea. At least that doesn't work as well for me.

So how did you— so now you're an entrepreneur in residence. What did you build inside of there and what happened next? Did any ideas spin out and then you went and ran with them?

Yeah, I had a few ideas that I liked a lot that Polaris didn't like. I had a few ideas. What were they? One of them was all around active traffic management. So predictive traffic management, kind of like Waze. Kind of like Enrix. Both companies will be billion-dollar companies. So I was working on those in 2004, 2005, um, and couldn't get it funded. Uh, at least Polaris wouldn't, wouldn't fund that particular idea. Um, there were a couple of other music-related things that I worked on.

Do you think that that would have worked on the web and not with the platforms of mobile of today? Um, do you think like the idea of Waze could have worked as a web-focused company? Back when you started it?

Yes.

Or do you think it needed the infrastructure to make it work?

No. It's better. It's augmented with mobile and it's augmented with smart mobile phones as opposed to dumb. But I mean, we had BlackBerrys at the time, right? We had Windows Mobile phones. They weren't as good as an iPhone or Android today, but I mean, we had smartphones in 2005. So, you know, they're always better every year, but we had plenty of infrastructure for that. To work properly. And INRIX, you know, a Seattle-based company here, is working a lot of the similar concepts. Waze was similar—

not—

it wasn't my idea, wasn't identical, but certainly in the same kind of idea of let's use a lot of data probes that are out there to do predictive traffic analysis and send me an alert that says, "Hey, did you remember there's a Seahawks game today?

So you better leave early if you need to get home at 6." You would see a lot of lights in the Google Maps red, yellow, green, and the Google Now, probably.

Yeah, that's correct. Okay. Yeah, this is 2000— this is 2005.

Yeah, yeah.

You know, it's almost 9 years ago. So that was one of the ideas, and we just didn't end up— and none of the ideas ended up resonating with both of us. And so I ended up leaving Polaris and joining up with Vulcan Capital, which is Paul Allen's venture firm. And so they hired me sort of as an entrepreneur in residence, but also to just help them productize ideas. So Paul had a lot of ideas, and Steve Hall, who runs Vulcan Capital, had a lot of ideas, but they didn't have any entrepreneurs to go turn them into companies. So they effectively hired me to do that, um, and one of those ideas that I worked on ultimately became Gist.

And so was it your idea or their ideas, or like, how did it— how did ideation happen inside of Vulcan? And, um, ultimately, like, when do you make the decision, like, okay, I'm going to do this as a company? Like, at what point have you spent enough time to figure it out?

Yeah. So, the early parts of my Vulcan time were primarily helping them organize a bunch of ideas they had on their own. Like, you know, back of the envelope. What about this? What about this? What about this? What about this? And I would do a little bit of who's the customer, what's the value proposition, what's the feature set, what's the business model, what's the competitive landscape. I got pretty good at that process and I could, you know, on a week or two weeks basis, I could churn a couple of ideas for them and I'd say, you know, on a scale of 1 to 10, this is a 4 and on a scale of 1 to 10, this is an 8. Hey, if we were going to pursue this, then we do this, that, or the other thing. I started hiring and managing small prototyping teams for the ideas that we thought were good. The idea for Gist really came from, I think, primarily Steve Hall who said, or Paul, which said, "What if I could have kind of an automatic newsfeed or 'newspaper' that told me everything I wanted to know? How would you do that?" We started thinking, well, you'd have to mine a bunch of data from the user originally and to get kind of a profile as it were, and then you'd have to go and hit a bunch of data sources to bring back the relevant information. I did a bunch of kind of prototyping. Well, if you want to know travel information, go to travel history. If you want to know sports information, you know this. Then I said, "Well, what if you wanted to know news about people and companies?" "Oh, that's the inbox." So I brought the inbox, my Exchange background to— we could develop an automated news service that gave you relevant information about your contacts by mining all of your inbox and algorithmically prioritizing who you cared about and then going into a bunch of news sources and bringing that back. So the idea that ultimately became Gist was, I'd say, originated by Paul and Steve and then enhanced with a bunch of my own background and perspective.

And so what did you do different when you decided to start Gist versus when you decided to start HelpShare?

I had a lot more— I had time. And I had certainly a lot more experience. I knew what it took. I had gone and seen what real software looked like. I mean, you go to work at Microsoft and you look at a global business and you look at a billion-dollar business as opposed to a $10,000 business. I know what product management was and program management and engineering and test and all the functional things. I had added all of that set of skill that I didn't have when we did Health Share. So I had, I think, much better perspective. I had Paul and Steve sort of pushing us on, "Let's not build something small. Let's go build something big that lots and lots of people, I mean, like tens or hundreds of millions of people are going to want to use." So that was all different and additive. And through my time at Microsoft and Polaris, I looked at and was introduced to lots of other entrepreneurs who were building really big companies. And so I started to have a perspective that was much larger than I had, you know, 10 years previous.

Okay. So who was the first person you called when you decided to do Gist as a company?

Uh— Well, it was— in this case, it was a little bit more iterative because we were slowly— like, the idea was coming together and I hired a small development team. Adam Loving was on that team, so Adam was at JIS with us for a while and he'd been working with me in lots and lots of other companies, and so he's one of my kind of go-to prototype guys. And JIS was not really— I hadn't convinced myself there was a company there until we built the prototype. When we built the prototype, connect to Gmail, parse all the message headers, give me a list of people and companies that I interact with frequently, and then go hit the Google News API and bring me back a feed of data. And when we hooked those two things up and we're like, whoa, this is cool, like this is valuable. But we weren't sure until you actually did a prototype. And Adam and this other guy named Toby Padilla were working on that prototype. And once they got that working, That was like a big step toward this could be a company. Then I had to make the mental choice to go to Paul and Steve and say, "I want to go run this company," as opposed to, "We should create this company," or, "We should hire some guys to go do this." I made a mental jump of, "I want to go do this. I want to go run this company and take these guys with me to do it." Okay.

This is an amazing story. Like progression through your life. And I'm— it's love. I'm loving this story. So go to Gist for a few years and get to like the end of Gist. You've built a product. Gist ultimately got acquired by BlackBerry. I think there were other acquisition offers that happened, didn't go through. Who knows what was going to happen? And like, do you feel at the end of Gist like that you wish— are you happy with what, uh, ended up with Gist?

Absolutely. And I'm sad. And I'm sad too.

Okay, why?

I'm, I'm happy because it was my first successful entrepreneurial venture. You know, you start an idea, you grow a team, you raise venture capital money, you sell the company, people make money, everyone's happy. Like, that's just— that is a— I think an unmitigated success in the entrepreneurial world, venture capital funded sort of startup world. Yeah, could it have been bigger? Sure. But everybody made money, nice return for their investors. As an entrepreneur, it was good for me, for the team. As you were one of them, it was good for the team. So check, good success.

Cool.

Two is we did something important, like we actually built something that was meaningful and useful. And, um, in fact, we took much of that and put it into BlackBerry BlackBerry 10 Contact Manager is largely Gist and put that into a mobile context and put that out into the world, which was part of the premise of why should we sell the company now, was we can put this in tens of millions of people's hands much more quickly inside BlackBerry versus what we could have done on our own. I think that was a significant success. The failure is that we didn't really get to realize the vision. I wanted to basically create the world's largest connected social graph because the way Gist worked was to bring all my contacts together— Facebook, LinkedIn, Twitter, and my inbox— bring them all together and understand who I know, how well I know them, and how that's changing over time. We didn't get to do that. In that way, it's frustrating or it's sad or it's a failure. Just today, RelateIQ raised $40 million to basically go and do that.

I saw that and I saw people tweeting about it a few days ago saying that they really liked the idea. I signed up actually yesterday. I got an email from their customer support and he's like, can I help you get it set up? And I tried to use the Google OAuth. It didn't even work. And I was like, I was like, it's just all the same, you know, the same problems and hardships with building software. But when I saw that funding round today, I was like, no one's still solved this even close. Right.

So it's exciting that we made some steps forward on that. Now Gist is all gone. It's evaporated into the ether. And yet there'll be more and more people that continue to try because the emotion still sits there. We all care about building relationships with people. And you build relationships with content, with context, by understanding that you did something or I did something and using that to say, "Hey, congratulations on doing whatever," or contextualizing our relationship in products like Gist or Refresh or RelateIQ or FullContact. Are all approaches to support an underlying human emotion of building strong relationships.

Man, can I ask you, how do you take your expertise? Whenever I think you work on something so long, I mean, you thought about it for years, and you see all these new companies in the last 2 or 3 years coming up, uh, you know, monthly pretty much, that are contact book solutions. And how are you taking your knowledge or experience in the space, which is greater than probably many or are you, and trying to help other companies like do things that didn't work for— or don't do things that didn't work for Gist, or do things that we thought worked really well, or like are you investing on the board of— do you spend time doing workshops? Like, I feel like the amount of companies being created in the space versus the amount of knowledge that you probably have, or learnings from what you've been thinking about for the last 7, 8, 9 years, do you do anything in that realm?

Yeah. So, Brad Feld from Foundry Group was an investor in Gist and he's also an investor in a company called FullContact. And so I've joined the board of FullContact and they're working at the problem in a little bit different way but certainly in that broad sort of umbrella, similar kind of approach. So now I'm on the board of FullContact. Products like Refresh which I think are awesome, like I volunteered my time and hopefully they'll take me up on that. I mean, any of these guys who are working on it, I'm willing to spend time on it because I want the solution to exist. Both for myself in a selfish way but also in the world. Like, I want something like Gist to exist and yet it doesn't. So I'm willing to put my time into trying to help these guys in addition to just— they're the next set of entrepreneurs and I'm always willing to spend my time helping other entrepreneurs.

So the company that you're involved with is FullContact.com?

Correct.

And then the app is Refresh App, correct?

Yeah, I'm not involved with Refresh in any way but I think that from what I've seen, in the spirit of using content to build a relationship, I think that Refresh has done the best job on the mobile phone. Before you walk into a meeting, it's like, "There's my contact of Shane, and here's where he is, and he's a Cubs fan, and he used to do this, and this is when you last talked to him, and this is where he lives, and these are your friends in common." The context they give you is insane.

I mean, it's one of the best. The way they tell the story too, they're like, "Hey, you should talk about this tweet because it was the most favorited," and all that. And it's funny thinking about just the one piece of the app that was just the best part was when there was the meeting in 10 minutes and you could say, I'm running late, and then it would have that little feature. It's in a text. And it was like, you're seeing like they kind of like pulled just that piece of the app and built an entirely like, like a full solution around just that singular use case, which is interesting. Yeah.

So they're actually getting a lot of their data from FullContact.

Awesome. Full contact.

They're a full contact customer, which is fine, but augmented it into the mobile context and made it slightly more meeting-centric, which is great. I mean, totally awesome, and there's lots of guys trying it from different directions, and I'm willing to spend my time trying to help them to be successful.

Okay, so go a little further now, and you were the CEO of Gist, and you raised, it was pretty much raising money was all on your shoulders, correct?

Yep.

And then I'm just curious, now your new company is Rival IQ, which is more in the B2B space, marketing tools of competitive research on all of your competitors. Mm-hmm. I don't know if you have a better pitch, but I mean, I like it and I use it. I'm curious from a personal level, you talked a lot about like building the initial team and stuff. How did you decide to go build a company with the 3 other co-founders you have there? And how did you decide to not be the CEO after being the CEO of your last company? Yeah.

So RivalIQ is marketing and competitive intelligence focused at active online marketers. I had this problem at Gist. Whenever I wanted to make a significant decision like pricing or a blog redesign or a page redesign or a feature, I would always go and look at my competitors. Duh. I'd also go look at what I would call aspirational companies, companies that had done it really well one way or another, and you wanted to basically screencap all of their effort and try to compare your own. So I actually had the ideas for ArrivalIQ a long time ago, kind of 2008, 2009. I'm seeing a theme here that it takes me a long time to develop an idea.

Or that you're 10 years early. So if I just had a list of all the things you thought about 10 years ago, I would just go start them all right now. That's what I think you should post. Here's my ideas from 2004. It's the perfect time. And then you'll give to everyone who watches this interview.

Maybe so. So, I mean, I fundamentally believe, I mean, to build a good company, it's so much more about the people, and the idea has to resonate equally with everybody on the team, the founding team specifically. And so I met John Clark. We were both mentors for Techstars. And we just enjoyed spending time together. He said to me, "Hey, I'd like to work on something with you." I was working my full-time job at BlackBerry, and I said, "Great. What ideas do you have?" I said, "It's much more fun to work on a thing." We kicked around a bunch of different ideas, and this idea for comparison really— less on competitive intelligence and more on comparison and learning by comparing myself to others. Kind of popped into my head and I sort of kicked that one out to him. He said, "Hey, that seems good." And we just kind of kept working on that. Like, we would get together like every Wednesday for an hour or two and we just kind of try to make a little bit of progress. Meanwhile, building a relationship with each other and working the idea. And so in this case, I mean, it was very clear early on. I mean, I had a day job at BlackBerry. There wasn't an opportunity for me to be a CEO in this particular case. So I was playing sort of co-founder mentor, and individual contributor. And for me, it's really quite exciting to be able to do both of those things or three of those things. And some days I do play kind of mentor. I play board member and I help John because I'm a CEO. I know how that feels and I can provide him a lot of like, a lot of guidance and/or just another sounding board to react to. And then other days I enjoy the fact that I'm not the CEO, right? It's his decisions to make. And I'm just going to go be the VP of marketing or I'm going to go be a product guy. And, and I think I learned different things in each one of those contexts. And it's really fun in a company like this to, to be able to bounce back and forth between those roles, learning and honing my skills in different ways for both.

So I want to, I want to end this up. We're coming up in about 45 minutes, which is, uh, between 30 and 45 is good. And I want to walk back to one last question, which is starting this new company, what do you think you're thinking about differently after doing Helpshare, which ultimately failed, after Gist, which was a success, or even thinking back to the Sailing Days? Is there something— the way you're approaching this company, the team, the way you think about kind of hiring, or the work style? Do you have an office? And, and in 2014, are you thinking about it differently, or what do you think about differently from the past things that you've learned from the other companies?

I would say that I'm drawing from my experience sailing in that it's so much about the team and the team dynamic and really believing kind of in my heart in the rest of the crew, rest of the guys. And I spent a lot more time in the early parts of Rival IQ wanting to feel that, wanting to feel a connection, a brotherhood as it were, with my co-founders. That takes time. It takes grunting it out. It takes arguing. It takes making up. It takes disagreeing in order to get to that, to get to a level of understanding and a level of trust. So I think I used to probably place more effort on idea. While my teams have always been good in my opinion, I'm erring more and more toward the fit of the team, the feel of the team, the skills and complementary nature of the team. And how we're gonna make decisions as much as what the decisions are.

That's interesting. So in a sailing context too, do you think at all, 'cause on a sailing, on a sailboat, like the environment is very clear. You're on a boat, you have a very clear destination, and that's how you win. Do you think at all about the environment of how you work to create, like to create that atmosphere for the team? Is that anything at all? Do you think of in that kind of thing?

Well, I think about— I would say less about the physical environment, but I would say much more about the cultural environment. So it's how do we interact. I mean, I'm a mechanical engineer and I draw a lot on the— what is the process of building a company as much as whatever the company is. How long is the sprint? Who does what? What happens on Wednesday? What happens on Friday? What happens when we miss a feature? What happens when we make a feature, etc.? And so we focused a lot of that at Gist, as you recall, and we focus a lot on Rival IQ, the process of which we're building the company. And that's everything from the engineering schedule to the how are we going to hire people and how are we going to do that differently, do it better than other companies, which I think ends up— if you take the sailing analogy, it ends up being able to get more boat speed out of the same dollar, more technology out of the same dollar, more productivity out of the same amount of people. Which ultimately I think creates an advantage. So we're focused a lot on who the people are, but also what is the process and how do we keep iterating on the process as much as we're iterating on the product.

Awesome. Well, I would like to thank you for that interview. That was an amazing story from going back to, from being a kid selling, uh, or mowing lawns. It's funny, you were personal branding back then. You named it T.M. McCann Lawn Care. If you ever have the business card, just send it in and I'll sniff it at the end of this interview. But I just want to thank you for coming today. Everyone, T.A. McCann, how can they reach out to you or say hello?

Yeah, I'm @TAMcCann, M-C-C-A-N-N, on Twitter, and my blog is TAMcCann.com.

All right, thank you very much.

Thanks, Shane.