Stockpickr: The Controversial Deal That Built A $10 Mil Company

When James Altucher made a daring deal to give 50% of his unlaunched business, a star employee was so shocked that he quit.

The guy had no idea that this crazy-sounding deal would generate millions of hits for Stockpickr, the investment advice site which was launched on a shoestring, and lead to a lucrative sale in under a year.

James is a much better storyteller than I am, so I won’t spoil the story for you by revealing the deal here, but I promise you’ll love it. Grab the interview now.

James Altucher

James Altucher


James Altucher is an entrepreneur and venture capitalist who has launched and sold three separate businesses, including Stockpickr. Of course he does this in addition to daytrading, futures trading, arbitrage, value investing, private equity investing, and whatnot. He’s also an amazing writer.



Full Interview Transcript

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Here’s your program.

Andrew: Hi everyone, my name is Andrew Warner, founder of, home of the ambitious upstart. Joining me is one of the most popular guests that I have ever interviewed. James Altucher kicked off my series of failure interviews by talking very openly about the time he lost a million dollars a week. Well, I invited him back this time to talk about the successes, and specifically what I’m curious about is how he launched, built and sold Stockpickr, a social network for stock traders. But as I said before the interview started, as I told you, James, wherever you want to go with the interview, I’m happy with. You’ve got so many great stories . . .

James: Thanks, Andrew.

Andrew: . . . and so many success stories, specifically, that I’m sure we can spend hours. So let’s start off with this.

James: Sure.

Andrew: I described Stockpickr as a social network for stock traders. What happened to it?

James: Okay. You know, that’s an interesting phrase, a social network for stock traders, because that’s how I described it, actually, at the time, as “MySpace for finance,” because MySpace had just been sold for $500 million or $900 million or whatever it was sold for. But the phrase itself was bullshit. I just used that phrase because that was the hot phrase at the time.

There’s kind of a back story, if you don’t mind me taking it two steps back. What happened was . . . well, I’ll start at the beginning and then move backwards. So, Tom Clark, the CEO of, called me up and said, “Hey, let’s get together and exchange ideas. I want to see what you’re up to.” And we would get together for breakfast once a year and exchange ideas. So I figured, OK, I’ve got two weeks to come up with something. I called up India and I said, “I’m going to start this business. I’m going to send you a spec, and I need to you send me back screenshots as if the site is already finished. I completely spec’d out Stockpickr – MySpace for finance – and I met with Tom Clark. I said, “Tom, you’re asking me what I’m up to. It’s too late, I’m already done with the site.” I showed him all these screenshots, the front page, the user pages, everything. I said, “I’m already talking to everybody about my new site.” I had sent out some emails. He said, “Why are you talking to everybody else? You’re one of us, you’ve got to do this with us.”

I had been writing for since 2002, and just so people know, was started by Jim Cramer, who has the TV show “Mad Money.” He’s a very well known financial pundit and former hedge fund manager. So I said, “Okay, Tom, how about I give you a piece of the company and in exchange, you fill up all of my ad inventory, so I’ll have 3 ads on a page.” And I knew I was going to get a lot of traffic, because I would write articles all day long for and link to all over the articles. I told Tom, “You fill up all the ad inventory,” so I’m making use of his entire ad sales team. He had 20 people on his ad sales team. I’m making use of all of them. I’m making use of his CPM rates. And I would be profitable instantly, because it was just myself and one business partner, and we actually had one employee. So I would be profitable instantly, and I would give up a piece of the company.

He said, “Okay, how much of the company?” I said, “Well, I’m thinking 10 percent.” And he said, “Well, I’m thinking 50 percent.” I said, “Okay.” Without even thinking about it, I said okay, because in a weird way, it’s much better to give up 50 percent of a company than 10 percent of a company. That sounds almost contradictory, like why would you want to give up 50 percent of something when you can give up 10 percent of something? But when you only give up 10 percent of a company, the other side doesn’t care anymore. He couldn’t care less. It’s 10 percent, that’s nothing for him. But 50 percent, they’re really invested. It’s part of their company. In fact, they have to consolidate it on their balance sheet if they own 50 percent. So there were some bloggers, actually, who were later criticizing me for giving up 50 percent, but it was the correct decision at the time. And I’ll tell you, I had my one employee, actually, he was so upset that I gave up 50 percent of the company to that he quit. And he wrote me a whole email, like a 3-page email, that said, “Not only am I quitting Stockpickr, but I’m quitting you!” And he was very angry. Have you ever seen that video, “Quantitative Easing Explained”? It’s these two cartoon bears that are explaining quantitative easing, and they call Bernanke “The Bernank”. It got about 6 million views. It was a fairly popular video.

Andrew: Okay.

James: Anyway, that was my former employee that made that video. So, talented guy. He shouldn’t have quit, he would’ve made some money on Stockpickr. But that’s basically how it got started–off of a couple of screenshots made in India off my spec. There’s a back story to that, but that was kind of the basics of that.

Andrew: And got 50 percent of it in exchange for selling your ads and nothing else, no cash put into the business, just them selling your ads?

James: No, and what’s great about that is, is that they did put a lot of cash into the business, because I was making about $90,000 a month, you know, forever, on their ads. So that’s all cash that they essentially put into the business, but suddenly it was revenues and profits to me. So I didn’t take in one dime of investment, I was profitable from day one, I had great revenues for a startup on day one, great revenues, and I had to give up 50 percent of the company.

Andrew: $90,000 in advertising?

James: Yeah, because let me tell you, I was writing about 5 articles a day for The I’ll describe the site in a second, and where the ideas from the site really came from, and why I don’t consider it a real social media site. But essentially, I would write an article on, “What Are Warren Buffett’s Top 10 Stock Picks? Here are 4 of them. For the next 6, go to and see Warren Buffett’s portfolio.” So I was getting a million visitors a month. Every visitor was hitting the site with 12 to 15 page views. So I was getting 10 million page views a month and selling advertising, just from the beginning. How many sites get that advantage? It was great. So I got distribution, I got revenues, I got profits, and I didn’t have to take in a dime of investment, so I didn’t owe. There was no cash in there. The first draft of the site cost me $4,000 to make, and okay, I gave up 50 percent of the company to Jim Cramer. Jim Cramer and I would do a video every single day mentioning the site. Jim Cramer would mention on “Mad Money” on CNBC, he would mention the site every single day.

Andrew: How . . .

James: It’s incredible. And I had the benefits of a 20-person ad sales team. Like, how much would that kind of distribution cost, and how much would those ad sales people cost me if I had just taken an investment and tried to do it myself?

Andrew: That’s phenomenal. How does he bring up Stockpickr on CNBC? I never caught that.

James: He would talk about a stock, and a little guy would help him come up with the stock ideas for “Mad Money” every weekend, emailing back and forth all weekend. What stocks should he do for the show? And so I would say, “I’ll make this portfolio on Stockpickr, “Top Garbage Collection Stocks.” And we’ll make this a portfolio. Stockpickr was basically a collection of portfolios. So I’m thinking of a portfolio, “Top Garbage Collection Stocks,” that are going to go through the roof. So he would talk about it, and he would say, “As I see on Stockpickr, my favorite website . . . ” would flash at the bottom of the screen, and it would get 100,000 hits right there, crashing all the servers at

Andrew. Wow.

James: It would crash all the servers because the programming was so utterly bad from my programmers in India that any load at all would crash any servers. You could have Google’s server farm and we would still crash it.

Andrew: All right. I want to get to the back story, I’m curious. Let’s jump forward just for a moment here. Last time you complimented me on asking you what you sold a previous company for. I’ll do the same thing.

James: Sure.

Andrew: What did you sell this company to for?

James: First off, we announced the site on January 3rd, 2007. I would say I built the site and launched the first version in mid-October of 2006, but it was a pre-launch. We launched officially on January 3rd, 2007, and put out a press release. That morning I thought I had caught a stomach virus from my kids. Jim Cramer and I were going to do a video about it; I was absolutely convinced I was going to throw up all over. I managed to hold off and throw up later in the day, but that’s another story. As soon as we launched the site, I put the site up for sale. So I called up AOL, Reuters, Forbes, Yahoo!, IAC Interactive Corp, and a couple other places. I can’t even remember them all. I called up every possible company you can call up. Just as an example of how small a world this is, I called up AOL by calling up Jeff Bewkes, who is the CEO of Time Warner and used to be my boss at HBO. I called up Mike Smith, who is the CEO of; by coincidence, 13 years earlier in 1994, I actually showed him the Internet, so what goes around comes around. We both worked at HBO at the same time, he had never even seen the Internet before. I showed it to him and 13 years later he is the CEO of So I called him up. I called up the head of business development at Yahoo!. His name didn’t sound familiar to me at all, and he said, “Oh yeah, you cost me a million dollars.” And I’m like, “How?” And he’s like, “Well, I invested in Vaultus, your last company.” And I’m like, “Well, you know, sorry, but maybe check this out.” So he did, and Yahoo! was taking a serious look at it. Similarly, AOL wanted to get into the social space as well, so they were very interested in Stockpickr.

Andrew: Now, you had nothing up and running, really. There was just a brand new website that was buggy and couldn’t even handle a few hundred thousand hits.

James: Yes.

Andrew: But you were already starting to sell it, with the idea that you were going to sell it as quickly as possible? Did you think you were going to sell within months of launching, or were you just laying the foundation for an eventual sale?

James: Both. I couldn’t really predict. I was determined–not to say that this was a bad business, because it was profitable immediately, and the fact that essentially guaranteed ad sales for two or three years, I forget the exact terms of the deal. I knew it was going to be profitable for a long time and I knew I was going to generate a lot of traffic. But I was for sale from day one. It didn’t feel to me like a $100 million business; it felt, to me it felt much smaller, and I wasn’t buying into the whole social media hype. And there was a lot of competition. So the Motley Fool was developing a competitor. I was maybe a little bit ahead of everybody else, but not that much ahead. Covestor was starting up, and they had a different twist on it. I don’t take any chances. If I can sell something and make some money, and put money in my pocket, I do it right away. Look, Larry Page and Sergey Brin, they started Google, they were getting a ton of traffic, and what did they do? They went to Yahoo! and said, “For a million dollars we’ll sell the whole thing to you.” And Yahoo! said no, so if not for that, they never would have made billions. They tried to sell almost immediately, so I did the same thing as Larry Page. Though he did a much better job at selling than I did, I was successful at selling. But I legitimately had everybody interested. I visited Google, Yahoo!, AOL, all these places.

Andrew: And when you eventually sold, how much did you get for it?

James: We sold on April 27th, 2007, a little less than 5 months later. We sold for $10 million, and of course owned 50 percent of the company. They didn’t pay themselves $5 million, so essentially we sold our piece of the company for $5 million.

Andrew: James, is this public?

James: Yeah, that’s public information.

Andrew: I didn’t see that.

James: It was buried in the filings. It was never announced in the press release.

Andrew: So within months, in well under a year, you created–out of nothing–this $10 million company, of which you pocketed just under $5 million, because you shared some of the equity with your employees.

James: Yes.

Andrew: I see. And this employee who left would have ended up with how much, if he would have stuck around?

James: Maybe $100,000 or $200,000. But he wanted us to go and make a $100 million company, and he didn’t want to have to listen to whatever Jim Cramer told him to do. If someone’s your partner, you do everything they tell you to do. And not just your partner–your eventual acquirer–and we knew that was probably going to be our eventual acquirer. My goal was to kind of get Yahoo!, Google and AOL interested, and then of course was going to have to buy it. They couldn’t own it 50-50 with Google. So our eventual goal was to get to buy it, if none of these other guys were interested. My view was, if Jim Cramer says, “Hey, could you put up a portfolio for Carl Icahn,” then three seconds later we do it. There’s no fooling around.

Andrew: What do you mean by portfolio? You mean, create a webpage for him with his portfolio so that it looks like he’s engaged with the site and has created his own account, but really you did it for him.

James: Right. Basically, what Stockpickr was, was we kept track of the portfolios of the top 100 or 500 investors on the planet. So Warren Buffett’s portfolio, George Soros’ portfolio, Fidelity’s portfolio, whatever. And then people would upload their own portfolios, and we wrote a little algorithm that said, “Based on your portfolio, and matched with all the professional portfolios, here are the stocks you should be looking at.” It actually provided a valuable service to people, to help them to pick better stocks than they currently own.

Andrew: Let me ask you this. It’s been about 5 years, so we can talk openly about it. Can a website that can barely stay up really be trusted? Should it be trusted to give people a portfolio to follow?

James: Well, the algorithm itself was good. I’ll give you a little bit of the Genesis of where the idea came from. In early 2006, I had an idea. The portfolios of all the top investors are public information. If you have $100 million or more and you invest money, you have to file with the SEC once a quarter. My idea was, let’s say Warren Buffett bought Exxon stock, and I’m just making up numbers, let’s say he bought Exxon stock at 50, and now Exxon is at 40. Well, Warren Buffett is essentially like my intern then, and I pay him nothing. So I can buy Exxon stock for $10 less than he paid for it, and I don’t have to pay Warren Buffett any money. And I get the benefit of buying these stocks from the best investor on the planet at a huge discount to what he bought.

My plan was, I wanted to buy a portfolio of 100 stocks at discounts to wherever the top investors in the world bought these stocks, and I wanted to diversify across investors, across sectors, across industries. I thought that would be a strong portfolio. A hedge fund offered me $100 million to start investing in that, and I would take about 30 percent of the profits for myself, which was an enormous amount of money. They had a couple of conditions, though. One is that I hedge everything, so if I went long on Exxon, I’d have to short some oil, or something opposite of Exxon. They wanted me to neutralize every position. They also wanted me to stop all of my writing. I was writing books. I was writing for a couple of different websites. I was writing for the Financial Times and I didn’t want to take the chance that I would give up everything and then neutralize all my positions, ending with a slight chance of making no money at all. So I said no to them. I said, “Okay, how can I make use of this idea in a way that I can make money off of?”

At the same time, I was running a fund of hedge funds, and my partner and I were offered millions of dollars to sell our fund of hedge funds to a bank. The bank had its own reasons for wanting to buy our particular fund of hedge funds, the details are not that important. But the one problem was that they wanted me to personally sign a six-year employment agreement, or else I’d have to return all the money. Even if they fired me at their own will five and a half years later, I’d have to return all the money. I just couldn’t sign the deal, and they said, “We’re willing to negotiate,” but it was just such a bad deal, and I never even returned their calls. I stopped returning their phone calls, which I probably should have returned. They still call me, actually, and this is like seven years later and I don’t return their phone calls. So I’m sitting there thinking to myself that we’ve created no real value at all with this fund of funds if I had to sign such an agreement. Meanwhile, we have this great idea . . . let’s just put it all into a website and call it ‘social’ and allow other people to upload their own portfolios. We’ll add some other features as well. We had about 10 different ways for people to pick stocks using our site. It was actually a very good site, and it actually helped a lot of people pick stocks. There was some value there.

Andrew: All right. Great idea. Then, you take it to India . . .

James: One other thing, I really thought all news about stocks and finance was bullshit. So this was like a financial media site with all the news stripped out. Anybody who tells you any news at all about stocks or the economy is just lying. Nobody knows anything. So this is just raw: Warren Buffett owns this stock at this price. Bam. You don’t need anything else.

Andrew: I see. Okay. And the way that you were marketing it, as you said, was you were writing articles for

James: Yeah, I would write five articles a day.

Andrew: You know what? How do you do that? How can you pump out five articles a day? As I heard that, I said, “Wow, if James is using article writing for other websites as a way of getting traffic to his site, as a way of building reputation, as a way of connecting with people like Jim Cramer, then maybe I should be producing five a day.” But then I started to think about it, and I realized one or two would be draining. How do you do five?

James: Well, stocks are different. It’s like putting together a bunch of pieces in an article. Let’s say, oil stocks that Warren Buffett bought in the past six months. Bam, that’s an article. Waste management companies owned by the best investors. Telecom owned by the best investors. Then I would do a blog-fest article, so I would link out to all the best blogs. Nobody was linking to blogs at the time–everyone thought, it’s bad to link outside your website–but I convinced TheStreet, let’s link out to all these blogs. So all these blogs loved me, I was the source of all their traffic. So they would link back to Stockpickr also. You do nice things to people, they do nice things to you.

Andrew: I see.

James: I was getting traffic from everywhere. Popular blogs like Paul Kedrosky and [inaudible] were linking back to Stockpickr and wrote favorable reviews. I also had interns help me with these stock articles; I would give them my ideas and my methodology for writing them, I would do the final draft while they put together the skeleton. But I was generating 5 articles a day.

Andrew: I see.

James: I wouldn’t have been able to do that, like five articles about entrepreneurship a day. That would be impossible.

Andrew: Unless there was a place to go and find tactics of other entrepreneurs, like Warren Buffett–maybe you find five of his quotes on how to build a company, and you add some extra meat to them.

James: Yeah, exactly. He’s got his letters, his shareholder letters. But in general there’s no standard formula. Where would you go to find Larry Page’s quotes? Where would you go to find Mark Cuban’s quotes? They have their own blogs too. But I was just pulling stuff from SEC filings, so it was great. I had a magic formula. Now, there are plenty of sites that do it, but I started that formula.

Andrew: I see. And it’s essentially the number posts that online marketers are so good at right now.

James: Yeah. And look, Yahoo! Finance distributed every single article, so really I was writing for Yahoo! Finance, because that’s where distributes all its articles. So Yahoo! Finance, essentially, was sending traffic straight to

Andrew: I see.

James: It was great. I had millions of visitors. And because I had a deal with, they had no problem with me linking every article to

Andrew: Okay. Actually, this is just a matter of months—four, five months of being up and running–there’s hardly anything left for me to talk about in a full hour. Was there anything that happened between the time you launched and the time you sold that could be especially interesting to entrepreneurs?

James: Yeah, a lot of things, actually. First off, as soon as you launch, you should put yourself up for sale. I’m not saying this is true for every case, but the goal of starting a company is to sell the company.

Andrew: I’ll come back to that actually, I’m going to write a note about that and I’ll come back to that.

James: The challenge for me is, I’ll call up AOL and I’ll say, “Here are 10 things you can do with Stockpickr, whether you buy it or not. Even if you don’t buy it, here is what we want to do for you.” I actually wrote for AOL Finance for a long time after that. We still did a deal, even though I didn’t sell to them. I started writing for Yahoo! Finance on a weekly basis, and they would let me link back to Stockpickr, because they wanted content. Forbes, I started writing for them. Even though they didn’t buy the company, no matter what, I always said, “Let’s meet. I have this thing, it’s the first social media site for finance, I just want to show it to you. You can buy it, or we’ll do some other deal.” So even if I hadn’t sold to them, I already had plenty of ideas for how they can use this site, even if I wasn’t selling the company to them. It was very useful to sort of half-put yourself up for sale almost instantly, and meet everyone else in the space, just non-stop meetings. I met people breakfast, lunch and dinner. It was fortunate for me, because over that time, I had lost enough money for so many people that I had a large network of people who would take my call, and it was great. I knew people at every single company. Actually Google, I didn’t though . . .

Andrew: You don’t feel awkward, by the way, talking to someone who you just lost money for? I would feel like that’s the one person I should avoid talking to for a while.

James: Well, that was only the Yahoo! case, and he had worked at Allen & Company, he would have invested in Vaultus. I’m sure, personally he lost a little bit of money, but look, time passes, it was 1999, there was a dot-com bust after that, so it could hardly be called anyone’s fault. It just happened, and you just move on. People move on.

Andrew: Okay. So what else?

James: Actually, I had built a very good site. The next thing is, I did the site extremely cheaply. As I mentioned, the first draft of the site cost me only $4,000. I used to find the developer. I would use again, but I would never outsource to India again. The reason is, it was a major, major headache. I could not communicate with these people. They were only awake at 3 a.m. my time. Sometimes there would be religious holidays I wouldn’t know about, sometimes the power would go out there without me knowing, I needed something every day and I often couldn’t reach them. So now I would only hire people local to me; that was a very important lesson I learned. Though to be fair, I used them again later on, but that’s another story.

Andrew: Okay.

James: Another thing I learned, every week, I added new features. It was very important to add new features every week. First week, everybody could their portfolio up. Second week, everybody could put a blog up. Third week, everybody could start sending messages to each other. Eventually I had StockPickr Answers, where you could ask any question about stocks that you wanted, and anyone else could answer. My only regret there was, I didn’t turn that into its own separate company, completely, as a Q&A widget, which would have been a successful company in retrospect. That became the most popular area of the site, by far. It’s still the most popular area of the site, even though I’m not involved in it anymore. Other things I learned I learned from it . . . those were the main things. Keep adding new features, constantly show that you’re innovating, so that your audience is always coming back to see what else is on the site.

Andrew: How does a non-programmer manage developers and get them to be so productive–to add blogging, Q&As, portfolios–all this stuff is very tough to manage remotely, especially for a non-developer. Well actually, do you develop? Do you do any code?

James: Well, I went to undergrad in computer science, grad school in computer science, I was a computer programmer for probably 15 years. But I tried, actually, to look at the code when I couldn’t find these guys, and it was as if I had had a lobotomy. I couldn’t figure out how to program anything at all.

Andrew: Were you able to guide them better because of your development background?

James: Probably, but I was a micromanager. I knew exactly what I wanted out of the site, not as a programmer, but as a stock trader. There was competition in the space–some undergraduates from Stanford started a site called SocialPicks. But they didn’t get it. I was a real hard core trader, so I knew exactly what I wanted on the site, what would be useful to me. I was able to really micromanage because I was a trader, not so much because I was a programmer.

Andrew: Like what? What did you get that they didn’t get because they weren’t as experienced?

James: Well, I knew exactly what would help me trade better. I wanted everything up front, on the front page. Social sites have these big letters on the front page and you have to click through three or four pages deep. You have to sign up. I wanted no friction. As soon as you got to the site, you were getting bombarded. This was my whole thing when I was presenting to Yahoo! or AOL or whoever. Right from the front page, there were 12 different ways to get ideas about what stocks to buy and there was no news. For me, that made it an incredibly valuable site. I wasn’t competing with anyone’s news site, and I was just adding these social features. Everyone wanted to do a deal with me, and then of course ultimately, I sold to TheStreet. As for other things I learned . . . one very important thing I learned from the experienced, when I first started, I started up to 10 other websites at the same time. I knew I wanted to start another business, and I knew I wanted to get back to the Web, but I didn’t know what would work. So I set aside some money and I built and about 10 other websites, 9 of which failed and Stockpickr flourished. All this stuff I’m describing about Stockpickr–I met with these guys, I met with that guy, those guys, I added these features–I was doing this for 9 other websites. It just happened to be that Stockpickr was the one that worked.

Andrew: Why? Why didn’t the other ones work?

James: Very simple. For Stockpickr, I had distribution. was linking every day to Stockpickr, and people trusted me; I was a trustworthy source on where to go for good stock ideas. So I’m building, and I’m there every day and Jim Cramer was on there every day, it’s a trust source for stock ideas. We just started generating millions of pages. If I had created a dating service, I had no idea how to create the numbers. I had no idea how to create distribution for a dating service. So I tried to create a dating service. I tried to create a beauty contest site. I tried to create a site that allowed other sites to create contests on their site. But I had no real way of generating partnerships as easily as I was able to with Stockpickr. Stockpickr, I could right away call the head of Yahoo! Finance, the head of AOL Finance, the head of Google Finance, Forbes, Reuters, IACI, and right away I get meetings. So distribution was key.

Andrew: I see.

James: And domain knowledge. I don’t know anything about dating sites any more than you do or anyone else does, but with a site about trading stocks, I knew more than anybody in the world. To this day, I know more about every type of trading strategy than just about anybody. I could create another stock site if I wanted to and I have confidence it would be good. But a dating site? I always have ideas, but I’m not sure if it’d be any better than

Andrew: You did a post recently about a dating site that you created, I forget what the name of it was.

James: Yeah,

Andrew: 140Love. You said that you spent $40,000 or $50,000, I think it was, to launch it?

James: Yeah.

Andrew: Why did that one cost so much to create, especially considering the fact that it’s based on Twitter and built with so much Twitter integration? Why did that one cost so much, and this one cost only $4,000 for the first version?

James: There’s a lot of reasons. I want to say there’s kind of a superficial reason, that I didn’t know what I was doing, I was using multiple developers, I doing more than just creating, I was also creating a way to make generic 140- or Twitter-based communities, of which was going to be one of them. I had all these ideas and I was trying to throw it into one business. I think at the core, this is what we discussed last video, I was off my game, I was not doing my daily practice. I was going through a divorce, so emotionally I was a mess, mentally I was a mess. I was not really generating good ideas for myself. Spiritually I had nothing going on. Physically, I was probably . . . look, I was getting a divorce, I was dating every night, eating too much food every night, drinking every night, and I just didn’t know what I was doing. The four legs that I discussed in the last video, that you really need in order to be a success, I probably had zero of those 4 working for me. Whereas when I was doing Stockpickr . . .

Andrew: I see. So it was because you weren’t focused, right? It’s not the idea, necessarily.

James: Right, it wasn’t the idea necessarily. Well, it was partly the idea. The idea was no good. Why was the idea no good? It’s because from the core outwards, I didn’t have all the cylinders working in the body. You need to have everything in balance to have success. You and I both, right now, have a million people competing against us for attention, for money, for success, for whatever. Every one of those million people would like to slit our throats in a dark, so it’s either us or them. In order to be in shape, you have to be a superhero; in order to be a superhero, you really need your physical body in shape, your emotional body, your mental body, and your spiritual body. I had that for Stockpickr, I didn’t have that for 140Love.

Andrew: Tell me something. Sometimes I feel like when I’m really in superhuman shape, is when I’m out drinking all the time, trying to pick up women everywhere, feeling like I could do anything, including eat anything and then go running in the morning. Doesn’t that sometimes make you feel so confident that you could take on the world, and then translate it into success?

James: No, I think that’s illusory.

Andrew: Really?

James: No, I don’t think that works. I think you really need to sleep a good number of hours, sleep better than your opponents. I think you need to be feeling really clean and healthy. I think you need your mind to be as sharp as possible, and if you’re drinking, you’re mind’s not going to be as sharp as possible.

Andrew: But doesn’t that make you boring? Isn’t it that interesting people who feel like they can just break rules and get away with it are the ones that everyone gravitates to, and has confidence in, and wants to work with?

James: Yeah, but those are flashes in the pan, and they’re not going to succeed in their business in the long term. Again, the sharpest guys–the guys with the most success, who have it all together from the physical to the spiritual–those are going to be the most interesting people in the long run. So no, I don’t think you can succeed if you don’t have all of the bodies aligned.

Andrew: Okay. You said you wanted to sell from day one. I understand in your book, “How to Be the Luckiest Person Alive”, you talk about the first company you should sell for anything you can get. Basically to get a notch on your belt, get some money in the bank, and later on you can swing for the fences. This isn’t the first shot that you took–why not swing for the fences here? Why not say, “Hey, you know what? Jim Cramer’s going to be known for years, for decades, for The, and the reputation that he built with that, and the influence he has from that. Why should I build this tiny little thing that fits in his empire instead of trying to create my own big empire and have other people sell to me?”

James: Well, I could have, but I felt for myself personally, I had just spent a couple years running this fund of hedge funds, and I had just essentially rejected the offer to sell that. So I was feeling the urge to sell something. So I built something specifically with the purpose to sell it. Maybe the next thing I do will be more for the long run; certainly in several of the investments I have right now, I’ve had the opportunity to cash out, and I’ve allowed those investments to keep on running.

Andrew: For example? What do you have now?

James: I’ve invested in Buddy Media, for instance, which a few months ago did a very healthy round. Some 4X higher than where I invested. I’ve invested in, the URL shortener. I’ve invested in a lot of biotech companies. I’ve invested in a bunch of internet companies; altogether I have about a dozen different investments.

Andrew: Why not launch multiple companies the way you did before instead of investing in other businesses?

James: I’ve thought about it but right now I’m really enjoying doing my blog and helping people and doing these interviews. Let me ask you this, what would you do if you had $100 million? How would your lifestyle be different?

Andrew: It would be exactly this. I would be doing interviews like this, maybe extracting more value from the interviews.

James: Starting a really good business is really, really hard to do. Even Stockpickr, which sold for a relatively puny sum compared to other companies, was 100 hours a week of work and stress. Enormous, enormous stress. You know, if I had $100 million, my lifestyle wouldn’t be any different either. I enjoy my life exactly the way it is right now. Look, when you invest in other companies and other smart people, it’s as if you’re paying these guys to work 100 hours a week for you, and we get to chat on Skype. So I’m not interested in working, like, a thousand hours a week again, and I don’t need a billion dollars. I don’t want it. If somebody gave me a billion dollars right now, I’d give away at least $990 million of it. I couldn’t give a shit about it. You don’t need it. I know from my experience, money won’t make you happy.

Andrew: You seem open about it, so I’ll ask about it. You talked about how in your first marriage, there would be days when you would just go out–I forget the excuse, it would be something like, “Honey, I’m going to go throw out the garbage”–and then you would go and sit in a coffee shop and read a book. I know that sounds dorky, but sometimes I totally get that.

James: Do you have kids?

Andrew: No, I just got married, so I don’t want to do that now. But I get the need sometimes to just go and sit and read a book. I know for other people it might be going to sit in a bar and watching sports. For me, I go and sit and read a book, or like you did, I might go find a poker game somewhere. It feels like that’s partially because you need to constantly be challenged. Now, you’re in a new marriage. How can a single person keep you so challenged that you wouldn’t want to go and play poker all night, or go and sit in a coffee shop and read one of the greatest, most engaging books that you can grab?

James: Well, there are a couple of answers. Right away, I was off playing poker or whatever, but I think the big issue is, I was probably too young to get married, for me personally. Maybe I got married for the wrong reasons, I don’t know. Right now, I’m happily remarried, and I’m not sneaking off to the coffee shop. So it really just depends on the person you’re with, where you are in the stages of life, and what’s right for you. I was certainly happier after I was separated from my wife. I was feeling lonely and then I would do anything meet people. I became the master of meeting people; I put an ad on Craigslist once, the day before Thanksgiving or on Thanksgiving Day, and it said I’m a psychic and anybody who wants can write me and I will use my psychic powers to answer their questions. I got a ton of people writing me, and I engaged in all these dialogues where I was pretending to be psychic and answering people’s questions, just because I wanted human contact on Thanksgiving day, otherwise I would’ve just been sitting there by myself.

Andrew: What did you do to meet women when you were dating?

James: Everything. I’m a shy person in a group, or in a bar, but one-on-one I’m not shy at all. I was on every dating service contact people. I would ask out women on elevators, between the 1st floor and the 10th floor. I knew exactly what I wanted, so I wanted to meet somebody I was going to fall in love with. I was aiming for sheer quantity, because I figured I was going to fall in love with one out of 100 or 1000, or who knows how many, so I needed to churn through as many people as possible. So, meet someone in an elevator, go on a date, if it didn’t work out, go on to the next one.

Andrew: How do you ask someone out in an elevator? That’s not an easy thing to do.

James: No, it’s not.

Andrew: So how do you do it?

James: OK, I’ll give you one specific case. I get on an elevator, and there’s a woman there, and to be fair, she was upset. I could see she was agitated, running her hand through her hair. Finally she said, “Boy, 2008 just sucked for me.” I said to her, “I can tell that 2009 is going to be much better for you than 2008.” And she said, “How could you possibly know that? You don’t know anything about me.” I said, “Well, tell me some things that happened to you in 2008.” She told me: her father died, she got a divorce, she had been married to somebody who was a hundred-millionaire at 25 years old, she was upset about the divorce, he cheated on her . . . so we got off at her floor, we kept talking and eventually I asked her out. That’s one example.

Andrew: I see. So just listening to women tell you what their problems were, or listening what was going on with them was what helped you connect with them.

James: Yeah, and I was sincerely interested, because I wanted to know if this person was going to be right for me.

Andrew: And always, in your head, you were thinking “Is this person right for me, long term? Will I want to marry her?”

James: Yes. Look, any relationship is the same, whether you’re going to sell your business or get married. I mean they’re obviously not the same for obvious reasons, but the same in the sense of, do you want to inherit this person’s problems, issues, family history, business history, employment history, and so on? So you need to learn as much as possible, as quickly as possible. That’s what I would do. Again, I started 10 sites, and one site was the correct business. I had to go out with 100 different women to figure out the one that was really going to flourish for me.

Andrew: I see.

James: And it’s all selfish: I want the one that’s going to help me, again, align the physical with the spiritual as easily as possible. Someone who would be on the same page as me with that. Otherwise, I’m going to be a failure, not only in marriage but in business. There’s a saying, “Happy wife, happy life.” And it’s really true. If you’re not happily married, you’re going to start failing over and over again in business.

Andrew: I can’t imagine the distraction that a divorce must be. It touches every bit of your life, you get frustrated on a very personal level, I can’t imagine it.

James: It’s horrible. I also had kids, so I wasn’t seeing my kids as much. I started three different companies during this period when I was separated. One was this company, Jungle Smash, that I started with the Freakonomics guys, where we were crowdsourcing ads. I think the site is still up, actually. Basically, I would pick a random brand, Crest Toothpaste, and the Freakonomics guys would announce, “Make your own ad for Crest Toothpaste, submit it on Jungle Smash, and we’ll pay $2,000 to whoever produces the best ad.” We were crowdsourcing ads for Crest. I didn’t get Crest’s permission, nothing. I didn’t contact them. They actually contacted me and submitted about a dozen ads for the contest, which showed me that there was some value to this idea. Procter & Gamble was intrigued. So I did Crest toothpaste, Monster Energy, we got some great videos up, and I paid out some prize money. But you know, I was going through a divorce, this was October-November-December 2008, and I actually still think this is a good idea, the idea of crowdsourcing ads for multi-billion-dollar companies. But I just let the idea disappear, and that’s one of the easiest ways you can let a business idea fail, is you just don’t spend the 100 hours a week at it, you spend 10 minutes a week at it. And I started 140Love, which also failed.

Andrew: You know, what I’m finding in my interviews is that there are some people who are so committed to one idea that they will either make it into a huge hit, or they will crash and burn with it.

James: Yeah.

Andrew: And then there are others who are more like you, they’re tinkerers. They’re going to try a bunch of different ideas, each one capturing their attention, and sometimes one will work but sometimes they’ll come here and tell me that the reason they failed was that they couldn’t focus. You seem to have this tinkerer-try-lots-of-different-business-ideas approach, but it worked for you. Why did it work for you? How do you make it work, actually? How can my listeners, who are like you, make it work for them?

James: Do you know how to play chess?

Andrew: Yes. I love it.

James: So when you play chess, it’s the middle of the game, you have a complicated position in front of you. You don’t know if you’re going to win or lose yet, but it’s complicated. All the pieces are still on the board, you’re positioning. So what do you do? The correct way to play is, you find the five or six “candidate” moves. You don’t even analyze two moves. These are the five or six moves that I could potentially make right now that seem good to me. Then one at a time, you start looking at them, and you back up, you look at another, back up, look at another. I think it’s important for your mind to be as flexible with these businesses as possible.

Not everyone’s going to create a Google. The Google guys didn’t even create Google–they wanted to sell their business immediately for a million dollars and they failed. They wanted to be academics, they didn’t want to be billionaires. Then they couldn’t figure out a business model, so what did they do? They bought several different companies, one of them–Applied Semantics–worked out and became AdSense for them, and that’s 99.9% of their revenues. Were they lucky? No, they were genius guys, and they knew what they were doing. But they were tinkerers also, and there were lots of things happening in their lives between the time they started, or as it was initially called, and now they’ve got $15 billion each. They could have been worth $500,000 each and been employees of Yahoo! at this point.

You have to have a flexible mind and be ready for anything, and that’s why it’s important to have the idea muscle working strongly for you every day. You’re always going to have things that are blocking you, and you have to be able to back up quickly and go to the next thing. So, Stockpickr, we were crashing every day, when Jim Cramer was mentioning us on ‘”Mad Money.” We’d have so many hits we’d crash because my programmers were awful. I had to think, what am I going to do? Jim Cramer’s going to keep mentioning me, and I can’t even let him know that we’re crashing every day. We crashed the entire, because we were tied into their servers at one point.

So I called up a friend of mine I hadn’t seen in five years. It was Martin Luther King Day, so I called this guy up on a holiday, and I hadn’t spoken to him in four or five years. It just so happened he owed me an enormous favor. So I said, “Look, Chet, I’m sorry I haven’t called you in four or five years. I know you’ve been calling me, but I need this favor. I’ve got these guys in India who don’t know what they’re doing. You’re from India, and you’re the best programmer I know, so I need you to call them and I need this problem fixed by noon, and it’s 9 a.m. right now.” He said to me, “James, I need to catch a plane to France at 4 p.m. today because I’m speaking at a conference”–he’s the best programmer at IBM right now–“I’ve got to catch this plane at 4 p.m. I’m going into the office right now. I’ll call your guys in India. We’ll fix this problem for you.” He really is the best programmer I know. I’ve known him for forever, and he did it. So I was able to use my network, I was able to think, who could help me? I called the right guy, I got lucky. Everything combined together worked out for me, he fixed the problem. And that’s what you always have to do; you’re going to have these problems every day when you’re starting a business.

Andrew: Usually, though, tinkerers, because they have so many other projects, when it gets to be that difficult, they back away and they go focus on another one, because that one might be easier.

James: This is why if you’re staying up late at night drinking, or sleeping late, or are not grateful for the things you have in your life, you’re going to be in trouble. At that moment, you have to be able to discern, “No, I’m not going to work on this little dating site, I’m going to work on because this is the one that’s going to work for me.” And I might have made some wrong decisions along the way, I’ll never know. But did work for me, and that was because it was the horse I chose to ride.

Andrew: Is that what it is? At some point you committed to Stockpickr, maybe because you were committed to, and to Jim Cramer, and they were all counting on you and giving you this great shot? Is it that once you commit, you can really bring everything that you’ve got to the business?

James: Absolutely, you have to do that. If at that point, when the site was crashing, I said to myself, “Okay, oh well, I’m just going to have to start with something new,” then I probably would have shot myself in the head by now. When I decide something’s going to work out, it has to work out. But you have to give yourself every opportunity before that moment, to be flexible and back out. At the exact same time I was starting Stockpickr, I was trying to sell my fund of hedge funds, I was building 9 other sites, and I was trying to convince and $11 billion hedge fund to give me $100 million to trade. And I probably had five other things going on. So you have to juggle lots of different things until one thing really starts to catch fire, and that’s the thing you do. And you have to really make sure every day that you’re not smoking crack. There was one day when I suddenly realized I had three competitors I didn’t even realize were out there. So I had to really ask myself, “Am I smoking crack?” Ask yourself that almost every single hour of the day, or else you might end up smoking crack, and that’s no good either. So then you’re smoking crack, and that’s just as bad as drinking at night.

Andrew: You know, we have a mutual friend, Tim Sykes. Tim Sykes sent me an email, let me see if I can find this thing. Guy sells to StockTwits, you know what I’m talking about?

James: Yeah.

Andrew: He told me about the sale to StockTwits on Mixergy a while back . . . the guy only received $845 from the sale to StockTwits. What’s going on? He created Chartly with Adarsh, they sold it to StockTwits two years ago, only received $845. What did they do wrong? I thought that was a good sale for them?

James: There’s always a point in a deal where 90% of the negotiation is talking about the worst-case scenario. But nobody wants to talk about the worst-case scenario, because we’re all friends. If you and I do a deal, we’re only going to talk about how much money we’re going to make. We’re never going to talk about what if Andrew decides to steal all the assets, or what if James decides to stop working on the code. We’re never going to talk about all that stuff, because we assume we’re all in this to make a billion dollars. But 90% of any negotiation, at the end, has to be about the worst-case scenario, even though that’s the most painful part, and it’s also the part where there’s only a 1% it’s going to happen. But sometimes that 1% happens, and you have to make sure you’ve legally mapped out what happens. When a lawsuit occurs, as is occurring right now between Tim Sykes and StockTwits, they did not map out that 1% chance, all the things that could have gone wrong.

Andrew: What’s the 1%? What went wrong here? What do you think?

James: I haven’t looked at the actual lawsuit, so I honestly don’t know, it would just be guessing on my part. I like Howard Lindzon, I like Tim Sykes, I’m friends with them both, both have talked to me about the suit but I don’t want to hear it, and I don’t really know. I do know, though, they both fucked up really badly when they did not negotiated for every possible situation. Even when I sold Stockpickr to, and I was best friends with them, we negotiated every possible scenario, and you have to do it.

Andrew: Even when you did the original negotiation to sell 50%, you went in there and you negotiated every little detail?

James: Every little detail. I always negotiate every little detail. And you know what? Lawyers will screw you. I never use a lawyer. I know my company, I know my deal, I know everything that can go wrong, a lawyer is never going to know everything that can go wrong. I negotiate my own deals. My divorce, I negotiated and wrote up the document myself; I just needed a lawyer to do the paperwork. My entire divorce cost me $1,000, much less than any divorce in the country right now.

Andrew: Wow.

James: And it worked out well.

Andrew: I would love to have Tim Sykes on here to talk about it, or Howard Lindzon. I like them both, like you, I don’t know them nearly as well as you do, but to me it looks pretty bad. The guy sold a decent company to StockTwits, it’s a part of StockTwits. Even if the deal doesn’t allow for Tim and Adarsh to get more $845, I feel like Howard is a guy who should take care of the people who sell to him. But I don’t know.

James: We just don’t know the deal. I hear from both sides . . .

Andrew: I would like to hear from both sides. I’m partially provoking both sides right now, trying to get them to come on here and do an interview with me about it.

James: You should, although they’re in a lawsuit, so they probably won’t do it.

Andrew: You never know.

James: It’s funny how once somebody’s in a lawsuit, “Oh, my lawyer won’t let me talk to you.” Everybody suddenly shuts up in a lawsuit. Next time I’m in a lawsuit with somebody, I’d be happy to go on an talk to you about it.

Andrew: You come right here and do an interview with me next time you’re in a lawsuit with someone.

James: I’ll tell you something, I’ve never been in a lawsuit with anybody. I’ve run hedge funds, I’ve sold 4 companies, I’ve run funds of hedge funds, I’ve made money from people, I’ve lost money from people, no one’s ever had an opportunity to sue me, and no one’s ever wanted to. I’ve never even come close to a lawsuit.

Andrew: Well, I come close all the time.

James: Do you really?

Andrew: You know, not lately, but absolutely, for some reason, people feel like they can bully me with a lawsuit. So I feel like, all right, go for it.

James: I can’t even remember the last time somebody was bullying me with a lawsuit. Because if everything’s worked out in the beginning, you have no problems in the end.

Andrew: All right, maybe I’m dealing with different people. At least in the earlier days of my career, people felt like they could just push me around with a lawsuit. They’d just send these lawsuits and threatening letters over, like their lawyers are going to sue me unless I did this or that.

James: Well, I’ll tell you, I don’t partner with litigious people either. My current business partner has never been in a lawsuit, my first business partner on my first business, ReSet, had never been in a lawsuit,, of course wasn’t in lawsuits. And I’ll tell you, once told me to remove the Stockpickr logo from something, and I just did it. So if somebody tells me to do something, I usually do it, if it’s not a big hassle.

Andrew: Yeah, you can usually work it out like that.

James: Tim Sykes, by the way, I’ve introduced him to his lawyer, and she’s a very good lawyer and has helped him out of quite a few situations. Like when Shaquille O’Neal or somebody threatened to sue him, she helped him a lot.

Andrew: Why did Shaquille O’Neal threaten to sue Tim Sykes?

James: He mentioned a penny stock. I think it was Shaquille O’Neal, it was some basketball player.

Andrew: Oh, okay.

James: Yeah, he was involved in some penny stock that Tim Sykes trashed. Shaquille O’Neal’s lawyer sent a cease and desist, and my lawyer, who I had introduced to Tim, sent back a very strongly worded, “We’re not going to cease and desist.”

Andrew: Tim, I understand why people get into so many arguments with him. I don’t know how to say it, but he’s like the Howard Stern of the stock community.

James: Both of them! Howard Lindzon and Tim Sykes are both very argumentative people and they’ll both put down people very freely. I don’t put people down.

Andrew: I haven’t seen that in Howard Lindzon. How have you seen that in him?

James: He’s constantly trashing Jason Calacanis, he’s trashing Tim Sykes, Tim Sykes is trashing everybody on CNBC, Howard’s trashing everyone all over the place. In 10 years that I’ve been writing, I’ve never trashed anybody.

Andrew: Actually, Howard told me about that. He said that it’s part of his strategy. You push a guy like Jason Calacanis, who has an audience. He starts attacking you, which gives you a big portion of his audience, which gives you their mindshare.

James: Look, that might work, I don’t know. For me, I don’t do that.

Andrew: What I’m saying is, I understand with Tim. Tim’s a very aggressive person which is what makes him fun to watch, and I understand why some people have a problem with him, or keep him out of the cool community. When you think about internet entrepreneurs . . .

James: Let me tell you about Tim Sykes. Like anybody, Tim Sykes has his own roller coasters. So when Tim Sykes was going through a low point, I would bring him on and do videos with him, and everybody at TheStreet wanted me to stop doing it, from Jim Cramer on down. Like, who is this guy Tim Sykes? Don’t do any videos with him. But I’d still do videos with him every week, because I saw he was a good guy. And every day, somebody tells me Tim Sykes is a jerk, a fraud, whatever. But I’ll tell you, Tim Sykes has actually exposed, legally, real frauds, and he has really helped people. You can’t take that away from him. He’s actually helped people in this world. You always have to give him credit for that.

Andrew: I agree. I could see why some people who he was railing against might want to sue him, might want to shut him down, I get that whole thing. I get why he’s left outside of the ‘cool kids’ of the tech world community.

James: Sure. And he’s got a real business, too . . .

Andrew: He’s making more money than the people who are insulting him, and the people who don’t think of him as a real entrepreneur or a real stock trader. But what about you? Why is it that I don’t read about you on TechCrunch, why is it that I don’t read about your methodology in the startup community?

James: A couple reasons. And I always wondered this, for instance: when I sold Stockpickr for $10 million, there were a couple of other companies that sold for $10 million, like Delicious sold for $10 million to Yahoo!, mybloglog . . .

Andrew: Right, and everyone was talking about those companies and those entrepreneurs.

James: I honestly couldn’t understand, but I think the answer is . . . I don’t go to all the tech meetups, I don’t go to the parties, because–and I’m accusing these guys of anything, like, I don’t know what they do–but I just don’t go out on the town, I’m working at night. Or I’m working during the day. I’d rather be working on my projects or writing than going to the latest tech meetup or South by Southwest, or whatever. So you know, I think that has permanently, since 1995, made me not one of the cool kids in the crowd. But I might actually do a guest blog at some point for TechCrunch. I mean, they know who I am, but I’ve just never done anything for them. Or with them, I should say.

Andrew: I see. All right. Final question. Are you going to email me afterwards and ask me to edit any portion of this interview out? I’ve been getting a lot of those requests lately.

James: No, no. What would I ask you to edit out?

Andrew: Well, maybe because we talked about your ex-wife, maybe because we talked about your current marriage, dating, I don’t know. People lately have been getting a little bit touchy about what they’d said in my interviews and asking me to edit them out, which of course I don’t do.

James: You know, honesty is a very important thing. People are afraid that if they’re honest about themselves, that other people won’t like them. So you go on a date, and you always put your best food forward. You go on a business interview, you put your best put forward. Because you’re afraid, and there’s this arbitrage between the face you’re presenting and your real face. Well, my face is ugly enough as it is, so there’s no hiding it. I always figure I have nothing to hide. If people don’t like me for some reason, then they have their own issues, and that’s that.

Andrew: Nothing to hide, now this makes me feel bad as an interviewer, because I didn’t push and get anything that’s especially secretive. Well, how much are you worth?

James: You know, I don’t know, I’d have to ask my wife.

Andrew: Give or take.

James: I would say, if I included everything, you know, less than 10, more than 5.

Andrew: Less than 10, more than 5. Have you cheated on your wife, either one?

James: No, no, never. Look, that’s very draining. I’ve seen people cheat on their wives and then kill themselves. That’s like the most draining thing you can do.

Andrew: All right, I can’t come up with any other questions that are especially prying, and frankly, I can’t come up with anything that you wouldn’t put up on your blog. So I’ll say this: thanks for doing the interview. We’re all going to check out your blog to see what you’re going to reveal over there next, and check out the book, too, I’ll tell my audience. I would be the luckiest person alive.

James: And you have to tell me how to use your great products so that I can . . .

Andrew: I’m going to show you in a moment, actually. We’re going to end this interview and I’m going to show you with a tweet how to get this document thing that I’ve been using on the site. I need a good name for it. We’ve been calling it TweetToSee. So people tweet in order to get to see something.

James: TweetToSee. Okay. All right, good.

Andrew: All right, I’ll show it to you. Thank you all for watching. I’m going to go show James what we created over here. Bye.

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