#99 Dave McClure

David McClure (@DaveMcClure) joined James Altucher to talk about startups, the synergy of skills, and what it’s like to see your peers ride to the moon while you walk on earth.

Prior to this interview, I had never heard of McClure who is “an entrepreneur and prominent angel investor based in the San Francisco Bay Area, who founded and runs the business incubator 500 Startups. He is often described as one of the super angel investors.” Well, things, can’t be that bad when you’re a super angel. But McClure was a late bloomer, in the sense that it took time for him to build up the right set of skills for the right moment in time. He mentions this explicitly in the interview when he says that timing matters quite a bit. Paypal, for example, at one time was going to make mobile payment systems. Only just now is that coming to the market and the original design was for a company that no longer exists.

McClure has found his success running 500 Startups where he learned, “the biggest companies are often outliers.” It’s hard – maybe impossible – to sniff out the next big thing. Even McClure, who has decades of Silicon Valley experience (and remember that Silicon Valley has only been called that since the early 80’s) makes mistakes. He missed investing in Uber and calls it “the single biggest fuck-up of my investing career.”

That career in technology started when he sold his own company, then moved on to Microsoft, and eventually the Director of Marketing at PayPal. At these places he rubbed shoulders with some of the most successful entrepreneurs in technology but faced “a lot of mental challenges.” It’s hard to be around the best, see what they are doing, and then not compare yourself. Well, that’s an ultra-FWP (first world problem), you’re thinking. We’d do anything to be in his shoes. Maybe.  It really depends on where you’re sitting to begin with.

Writing in the LA Time, Michael Shermer explains:

Would you rather earn $50,000 a year while other people make $25,000, or would you rather earn $100,000 a year while other people get $250,000? Assume for the moment that prices of goods and services will stay the same. Surprisingly — stunningly, in fact — research shows that the majority of people select the first option; they would rather make twice as much as others even if that meant earning half as much as they could otherwise have.

What? Yup. It turns out that when we think about things, we often compare them to some baseline/normal/traditional level rather than absolute level. The woman with one million today feels great if yesterday she had half a million but awful if yesterday she had ten.

H.L. Mencken noted this in his definition of wealth: “Wealth – any income that is at least one hundred dollars more a year than the income of one’s wife’s sister’s husband.

Rather, don’t look at what other people do or have done:

“If you look at someone from the outside and they have a successful business or blog and a podcast and you’re like wow, there’s no way I could do that. I felt exactly the same way…. but jump in anyway.”” – Ramit Sethi (episode # 36)

McClure kept working, and looked for “an areas I’m actually doing well at.” Then a stroke of “luck” when Sean Parker asked McClure to join Founders Fund. He did.

Then in 2010 he stared 500 Startups, their boilerplate reads:

“We’re based in Silicon Valley, but you can find the #500Strong family of mentors, investors, and founders all over the globe. In the last 4 years, we’ve invested in over 700 companies in more than 40 countries. We have offices in Mountain View, San Francisco, New York City, and Mexico City.”

setofskills500 Startups began, McClure says, because of his particular set of skills. “I had both the engineering and marketing side and there weren’t that many people doing investing that had both disciplines.” McClure had what Scott Adams articulates as the right combination of skills.

“I’m a perfect example of the power of leveraging multiple mediocre skills. I’m a rich and famous cartoonist who doesn’t draw well. At social gatherings I’m usually not the funniest person in the room. My writing skills are good, not great. But what I have that most artists and cartoonists do not have is years of corporate business experience plus an MBA from Berkeley’s Haas School of Business.” – Scott Adams

But wait, there’s more!

McClure had also taught a class at Stanford University and had been organizing community events. He also had some “very interesting experiences that have served me well.” His intersection of skills included teaching, business, coding, and communal. Tim Ferriss had a similar path, using community as a tool to connect. Ferriss got involved with Silicon Valley Association of Start-up Entrepreneurs and began taking any job they offered. Soon he was organizing conferences and consequently meeting the speakers. One of which, was Jack Canfield (episode #90).

Toward the middle of their conversation James notes that “nothing is predictable” and McClure chortles, like an east coaster just told him that Californian has wonderful weather.

He explains the iterations that PayPal alone went through. “There was two year with three to five business models, shifting strategies and iterations before they found something that caught fire” McClure says. “That’s pretty typical.”

How then can you know what to invest in? James asks. MCClure says it’s hard. “It’s hard to know the person.” At 500 Startups they look to whatever track record might exist, what school they went to, and what they’ve made in the past.

Once someone gets in, they only succeed about 15% of the time. McClure sounds pretty reasonable and realistic when he explains that number, which isn’t often the case. What usually happens is we negelct the base rate. For example, “John is a man who wears gothic inspired clothing, has long black hair, and listens to death metal. How likely is it that he is a Christian and how likely is it that he is a Satanist?”

Duh, John has his wallet hooked to a chain. Guaranteed. Au contraire mon ami. Think instead of how many Christians (2B) there are and how many Satanists (~15K) there are. It is far more likely that John is a Christian with an affinity for black (which does go with everything). What we did there was take the sample in front of us and think deeply about that rather than thinking widely. These examples are fun, let’s do another:

Linda is 31 years old, single, outspoken, and very bright. She majored in philosophy. As a student, she was deeply concerned with issues of discrimination and social justice, and also participated in anti-nuclear demonstrations.

Which is more probably, Linda is a bank teller or Linda is a bank teller and is active in the feminist movement? Wikipedia has the deeper answer and if you like these sorts of things, add David McRaney’s You are Not So Smart podcast to your list of ones to listen to.

Bringing this back to McClure, we could expect that he would exhibit some bias toward expecting a higher success rate because he’s involved with a company. We typically overestimate this for a few reasons. One is that he succeeded in the past. If I can build and sell company X then I can build and sell company Y the thinking goes.

Another reason, Economist Daniel Kahneman explains  is that from the inside of a group we miss the view from the outside, we are overly optimistic, and we underestimate how long things will take.

This part of the notes is so long because it’s so important. This is a bias that it appears McClure has recognized and taken into his calculations. Like a chef might rework the menu because of a lack of lobster, McClure has reworked an investing philosophy. It’s not that no one will order lobster (that McClure will always avoid mistakes), it’s just that there’s some safeguards against everyone ordering the lobster (McClure making the same mistakes over and over).

James asks for suggestions about what might be one of the next big things, and McClure guesses home automation (just not yet), hardware and software combinations, and SAAS for busines. Steven Kotler (episode #10) had his own predictions.

About new business, McClure thinks that the ideas are new, but maybe not the technology behind them. “There’s nothing technically new about those businesses (Uber, AirBnb).” Rather it’s the synergy of ideas. PayPal was ready for mobile payments, but mobile wasn’t. Mitch Lowe (episode #67) had built a prototype of the Redbox rental machines for VHS, but the technology wasn’t there. A current example is Alex Blumberg’s (episode #70) Gimlet media which is increasing their pace because of the success Serial had. But Blumberg wouldn’t have a podcasting company without a mobile way for people to download them. I was listening to podcasts in 2005 and in a decade, we’ve come a long way. Timing matters for technology.

One bit of parting advice from McClure is to write about what you’re doing. Austin Kleon advocated for this in his interview with James and it’s something Gary Vaynerchuk (episode #2) has been shouting, whispering, and vining from every possible channel. (And your channel and message matters.) If nothing else, it’s a great way get your message out without relying on the press, said Jason Calacanis (episode #77).

Thanks for reading. If I nixed, neglected, or narrowed my focus too much, let me know: (559) 464-5393, @mikedariano, or in the comments. Plus, our book club begins soon. Sign up here.
One final story that didn’t fit. Uber comes up a few times in this conversation and a story about founder Travis Kalanick comes up around the 14:00 mark of this StartUp episode. Understanding it, will help you understand Uber.

McClure also had this reading suggestion:

#39 James Manos

James Manos joined James Altucher to talk about persistence, following your passion, and what it was like to write the College episode on the Sopranos. He also created Jimmy Stones and South of Hell which he talks about in this interview.

Manos has a rich IMDB profile with credits for Dexter, The Sopranos, and The Shield – the career “anti-hero” shows as James calls it. Manos says that the anti-hero is “a much more realistic version of what we’re all capable of doing and what we’re all capable of being.” This trend didn’t just happen. Manos says that The Sopranos was in “turn around” for five or six years before HBO picked it up. Originally it was bought by Fox, who David Chase wrote a pilot script for. They passed. So did every network to the point that HBO was the last broadcaster standing.

Even when the show started, “none of us were conscious of creating something that became truly iconic.” Manos tells James. It’s similar to this Dave Grohl quote about how Nirvana became Nirvana:


As the interview goes on, Altucher says that it seems like HBO was the “grandfather” to so many great shows. Manos says that “the best shows happen when the networks allow the original creator to do what they want to do. Disney knows this, so does FX.

For FX it went like this: “Basically, Louis (CK) gets very few notes, with very little supervision, for very little money. He has complete control over every aspect of the show and is able to create the show he wants.” But he’s talented, shouldn’t he get paid more? “FX exec John Landgraf explained, “I can write you a check right now for 200 but anything more than that I’m going to have to go ask Rupert Murdoch, and you’ll have to tell him what it’s about.” Louis agreed to keep it at $200,000.)”  This is an example of building up career capital and trading it for career control, a theme to our April book club

When you find a creator who has a chance to create, take the advice of Harold Ramis and try to stand next to them. (~1:10)

Part of the work feeling like play attitude that Manos has sought comes from working with people he likes. The world isn’t going to be full of kind and nice people, he tells James, so you may as well try to find some at work. Tom Shadyac (episode #15) said that working with Jim Carrey made him funnier, and vise versa. Brian Koppelman (episode # 98) said that marrying the right person was the best choice of his life. Find good people and be around them.

Manos’s big break came when he got “very lucky” in obtaining the rights to the “Texas cheerleader story.”  The movie included Emmy Awards for Holly Hunter nad Beau Bridges.

Altucher observes that it seems like story arcs for television has gotten more complicated. Manos doesn’t think so at the character level, and this is part of why he has been successful. His advice to Altucher about writing is that he writes what would be true to the character, and “my only goal is to come up with good stories.” In his eyes there is no change for a character, and if there is one that’s a failure of the writer. He said that working with David Simon was easy because he had such a clear vision. “If you know the characters really well, it doesn’t become all that complicated to reach your desired goal.” Manos says. In the Vanity Fair oral history Chase said, “I would always go away before the season even started and come back with a whole, overly complicated story arc for the characters. It started out very simple, just for Tony. Then as the years went on, I would do one for Tony and one for Carmela, one for Chris Moltisanti. Tony would have three story arcs by Episode No. 13; Carmela would have two or three; Chris would have a bunch. You’d lay them out and see how they’d all line up. Sometimes you’d see a resonance in the stories, and sometimes not. So we would start to work it out”

On a more macro level, Altucher might be on to something. In the book, Everything Bad is Good for You, Steven Johnson makes the case that games, television, and the internet are getting more complex over time, and that this is actually a good thing. Ironically enough, Altucher hits on what’s considered the start of this movement towards complexity in television with Hill Street Blues. “Watch an episode of Hill Street Blues side by side with any major drama from the preceding decades – Starsky and Hutch, for instance, or Dragnet and the structural transformation will jump out at you.” Johnson writes. Dragnet is a “single line.” Starsky and Hutch is a single line plus a “comic subplot.”  Hill Street Blues by contrast has more characters, more scenes relevant to more story lines, and fuzzy borders where one episode begins and another ends. Then we get to The Sopranos.

“The total number of active threads equals the number of multiple plots of Hill Street, but here each thread is more substantial. The show doesn’t offer a clear distinction between dominant and minor plots; each storyline carries its weight in the mix. The episode also displays a chordal mode of storytelling entirely absent from Hill Street: a single scene in The Sopranos will often connect to three different threads at the same time, layering one plot atop another. And every single thread in this Sopranos episode builds on events from the previous episodes, and continues on through the rest of the season and beyond.

Here’s are the graphs that Johnson uses to explain this. The vertical axis is number of threads, the horizontal axis, time.

everythingbadtvchartAltucher had a similar conversation with David Levien (episode #85) about this.

For the actual writing process, Manos doesn’t have much advice, even admitting that he doesn’t want to know how he writes. He’s not alone, none of the writing guests give great specificity about their process, but Simon Rich, (both episodes), Andy Weir (episode #92), and Ben Mezrich (episode #84) all beat around the bush. It’s not that they are intentional, it’s just that like, Manos, they aren’t sure how exactly it happens.

One thing Manos does know for sure, is that he needs to be doing it, the story telling. He said that he recently got a phone without email capabilities because “I don’t want to be inundated with email all day long.” He’s not the only Hollywood person to do so. In an interview with The Hollywood Reporter Christopher Nolan said he doesn’t have email or a cellphone. How can that be?

“Well, I’ve never used email because I don’t find it would help me with anything I’m doing. I just couldn’t be bothered about it. As far as the cellphone goes, it’s like that whole thing about “in New York City, you’re never more than two feet from a rat” — I’m never two feet from a cellphone. I mean, we’ll be on a scout with 10 people and all of them have phones, so it’s very easy to get in touch with me when people need to. When I started in this business, not many people had cellphones, I didn’t have one, I never bothered to get one and I’ve been very fortunate to be working continuously, so there’s always someone around me who can tap me on the shoulder and hand me a phone if they need to. I actually really like not having one because it gives me time to think. You know, when you have a smartphone and you have 10 minutes to spare, you go on it and you start looking at stuff.”

Toward the end of the interview, James asks “how do people find their passion?” That’s one of the big ideas here and Manos credits an old boss for giving him two weeks off to see if he really enjoyed the job he had. Zappos has something similar in The Offer.

Maybe though it’s not about finding your passion in a two week hiatus. Maybe it’s about finding your skill. Adam McKay was on the (very good) Working podcast.

“I’ve been doing this a long time. From the age of nineteen on, I was actively writing sketch and took screen play classes and I’ve watched thousands and thousands of movies, and I’ve rewritten and written – at this point – a thousand different kinds of scripts in my life.”

Thanks for reading. The book club starts in April and you’ll need to track down the book by the end of March. Sign up here. It’ll cover ideas like why you don’t need to check email as often as you think, what really matters in the passion vs. skill balance, and how you can build your own skills. It’s one book, six emails, in thirty days.

*A previous version of this post misspelled Jim Carrey’s name. 

#48 Marni Kinrys and Kristen Carney

On October 3rd, James Altucher interviewed Marni Kinrys (@WingGirlMethod) and Kristen Carney (@KristenCarney) to talk about “dating, sex, and comedy.” Marni and Kristen host the Ask Women podcast.
Altucher begins the interview by talking about how both Marni and Kristen have “created an industry by yourselves.” Kristen – the standup comedian – tells James that she was very observational. “I remember being, like, nine years old and thinking to these girls, you know, go to the bathroom by yourselves. Like, you don’t share a bladder.” Comedians often say they feel like outsiders and their comedy comes from observations like this. In his book, Dad is Fat, Jim Gaffigan tells the story about how his role in the family was the comedian and he liked making his family laugh. Even now he comedy focuses on being an outsider, how many other fathers of five live in a two bedroom NYC apartment and look like ghost who needs a tan?
Marni created the career of “wing woman” after she worked in PR and hated it. Then she reframed the issue. She hated PR for companies, but PR for individual guys looking to get dates she could do. Marni has been a wing girl since 2003 and she talks about David DeAngelo and pick up scene. Altucher shares a story about an ad he put up on Craigslist saying he had psychic powers. I’ve been reading Jams for a few years and this is one of the crazier stories he’s shared.
Marni goes on to talk about being invited by DeAngelo to speak at a conference where she met Mystery – a famed pick up artist.. I know next to nothing about pick-up artists, but have heard that Neil Strauss’s The Game is the definitive account. You can hear Strauss talk with Tim Ferriss about this and other things in their interview from June 2014.
Marni and Kristen then share a bit of their stories. They are both attractive women but from the interview, it sounds like it took time for both to see themselves that way. It took time for them to work through some insecurities to get to where they are now. If you’re a guy, and haven’t done this yet, they call that “Pretty Boy Syndrome, you know, when you are pretty when you’re younger, you never really have to think about having a personality because things just came to you really easily.”

Their pretty boy syndrome isn’t baseless. The idea of having to overcome obstacles comes up with many successful people. Malcolm Gladwell wrote an entire book about it, David and Goliath. One example from the book is the number of dyslexic executives at major companies. It’s a larger number than what their overall percentage in the population might indicate. Gladwell’s theory is that these individuals developed other skills to overcome their handicap. Steve Pressfield approaches this same idea from a wider angle in The War of Art.Marni talks about her testing grounds, Whole Foods. “ I know that if I want to get attention from other people, from men especially, I can walk a certain way. I know if I wanna be seen as open and friendly, I can walk a certain way.” Marni’s focus may be getting people from the bar to the bedroom, but the research on how you hold your body works for the boardroom too. In her widely popular Your body language shapes who you are TED Talk, Amy Cuddy reports on research about how fast we make observations about people. A one second clip of a political candidates face can predict their success 70% of the time. Researchers can show an audience a silent film of a doctor and patient interaction, and the audience will correctly predict whether or not the doctor gets sued.

Altucher brings the conversation back to the pickup scene, but asks what men should really be doing. Marni says, “Well, the first thing that I do in all of my programs is I have these guidebooks that I give to them that really gets them to know themselves and identify what their values are.” One method for this is BET. In her book, Do Cool Sh*t, Miki Agrawal outlines that BET stands for bullet, eliminate, take on. Agrawal suggests you list everything in your life. Relationships, projects, bills, commitments and so on. Once you have everything listed, start eliminating the things you don’t like. Once you whittle everything superfluous off, double down on what’s left. Greg McKeown writes about something similar in Essentialism, his book is a more comprehensive approach to it, providing many steps along the way.

Marni says something interesting about confidence, “confidence doesn’t mean that you’re, like, 100 percent confident 100 percent of the time and you never have a down moment. It just means that you can help yourself a lot faster and you don’t get into this depression hole from something small or even large happening to you. You have the tools and the skill sets to be able to handle whatever comes your way. That’s what confidence means.”

The interview ends with a bit about the books they’ve self published. Marni’s book is Get Inside Her: Dirty Dating Tips & Secrets From a Woman.

If you enjoy reading, our book club begins next month. Sign up now.

#98 Brian Koppelman

Brian Koppelman (@BrianKoppelman) is back! He joined James in episode #59 and in this one they  talk about getting over your creative hurdle, the value of good partner, and how easy it is to find success.

Koppelman is no podcast newbie either, he has his own show – The Moment – which has featured guests like Altucher, Seth Meyers, and Phil Hellmuth.

Their interview begins with a short discussion about how podcasting is a different sort of interview. They comment that no one would watch them sit in a room and talk, but there’s something about the mic, your speakers or headphones, and the captive nature of podcasts that’s different. Koppelman wrote about an example of this when Jim Breuer was interview by Mark Maron on his WTF podcast. It’s a good article. Really good and I don’t care for Breuer, Maron, or SNL but read the entire thing.

In Wired, Roman Mars (another great podcaster) said “It’s weird, but I love the closeness that people feel to me and to my show. Public radio once cornered the market on the closeness. Listening to NPR became the definition of who you were. And podcasting is a hundredfold more intense than that. Podcast listeners are so, so dedicated.”

Gary Vaynerchuk suggested something similar, but in regards to marketing channels. When Koppelman does his Vine videos, Vaynerchuk would probably applaud what Koppelman is doing. The videos are short and inspirational and appeal to people in a way that an article, a longer video, or even his podcast episodes can’t. It’s like a coach bringing a player over the bench, offering a few encouraging words, and then sending them back out there. It’s all about matching the medium and the message. Podcasting is still so new though, that there’s a lot to figure out.

For one thing, it’s not a quick way to make a buck. “It isn’t clear that there’s real money in it.” Koppelman says about podcasting. Jason Calacanis (episode #77) has been there, done that. He told James he tried to start a network and it doesn’t really work. He found that you need people with established bases, fans, skills and those people don’t want to work for anyone.

But Koppelman and James continue at it and begin talking about Solitary Man, about which Koppelman say, “that’s the movie of ours that means the most to me.” In part because he was stuck on it for so long. It took over three and a half years to write and another year and a half to get funding.

Part of that struggle was because Koppelman got stuck writing part of it and had a brief interlude as a stand-up comedian. I couldn’t help but that think that part of this was advice from Koppelman’s writing partner David Levien (episode #85) who told James, “when you’re doing something creative, you have to find different ways to stay fresh.”

And each iteration, each adventure, each small story is part of the bigger one. Koppelman reminds feeling that if he didn’t do something, he’d never do it. “When you’re thirty you do think to yourself, if I were going to do it, I probably would have” he says. Carol Leifer (episode #66) thought something similar when she had a chance for her own show. She had written on Seinfeld, on SNL, and for the Emmy awards. This. Was. It. Her own show! But it wasn’t. In her book she tells the story of Jerry Seinfeld coming over during filming for the pilot and saying:

“You know, there’s not just one thing, Carol. Take the pressure off yourself. It feels like the most important night of your life , but it’s really just another night in the bigger picture of everything you do. Now, go have fun out there .”

Each thing you do is just another fence post in the work of life, and that never ends. Koppelman said that you have to “keep moving forward, it’s always scary.” This is another theme the podcasts guests have hit on, success isn’t a destination but more like a mindset. You don’t arrive, land, or end-up successful. You “keep moving forward.”

Stand-up began a change within Koppelman, partly because he was surround with good people. “There’s an incredible power in having a creative partner” he tells James.  Adam Carolla (episode #25) met Jimmy Kimmel and thought “hey, this guy’s funny” and “we work well together.”

Solitary Man continued to be Koppelman’s white whale. As he trawlled through comedy clubs, the project swam untamed. Not finishing it made him feel like “a fraud.”

To break through the creative block he tried The Artist’s Way, but was stymied. He needed stand-up because it “could let me fail in a certain way.” He had to build up a set of skills and “pass a club” and slowly his fear abated. His fear of failing was melted away by the warm stage lights. Gretchen Rubin (episode #97) told James that repetitive actions like this can “dampen our emotional reaction to things.”

Ready to face his fears, Koppelman began writing and let his rough draft be rough. Jacques Barzun wrote, “let that first sentence be as stupid as it wishes.” But not forever so. Koppelman advocates for a band, a range, of creativity to fall in. You want to be vulnerable early and write anything, no matter how bad. But you need to be tough later on and welcome feedback that might rip it apart. It’s been these landings, between soft as cotton and hard as stone that the really good work is found.

Koppelman said he cranked away at the script and one day on the bus he realized what the missing part of the movie was. He said he rushed into his office and told Levien “I need five minutes” and he transcribed what he had written. Ryan Holiday (episode #18) mentioned something similar, saying he would finish a run and walk into his home, telling no one to bother him while he jotted down an idea.

Once the script was done, it was time to make the movie. Slowly. Koppelman faced resistance from the studios about the tone of the story and age of the characters. To combat this he had custom shoes made that reminded him he had to take one step each day to get the movie made. Doing one thing, no matter how small, was something Jack Canfield (episode #90) said he proposes too (though he suggests five).Slowly Koppelman’s movie got reeled in. Steven Soderbergh thought it was good. Michael Douglas agreed to star. But it took over a year to get the money.

James asks what is becoming his stock, but wonderfully open, question; “what would you tell someone who’s listening and sitting in their cubicle?”

Koppelman doesn’t disappointment and sounds excited to give five pieces of advice:

  1. Have good people in your life. “I luckily married the perfect person for me.” he tells James. Tom Shadyac (episode #15) said that he worked well with Jim Carrey because they each made each other better.
  2. Ask what you want. “What is most important to you?” he tells James. I’m guessing he got this from Tony Robbins, which means that Jairek Robbins probably got it from him when he told James that people need to learn what they want in life.
  3. Be selfish. If you don’t have a good dream, Koppelman says, “you become toxic.” This is what Scott Adams calls the right kind of selfishness. One that makes you and everyone around you better.
  4. Say no. “I cut it all out of my life years ago.” Koppelman tells James. There’s no obligations that don’t bring him good feelings.
  5. Don’t listen to experts. Experts don’t have the incentive to find a gold in the river, it’s to make sure the pan doesn’t get full of stones. Stephen Dubner (episode #20) used a soccer metaphor to explain why you should act toward your real interests, not perceived ones.

James follows up with another good question, but how do you know when to quit, when you won’t make it. “The line between being an artist and being delusional is very thin.” Koppelman says. Stephen King has his own suggestion:

The biggest part of writing successfully is being talented, and in the context of marketing, the only bad writer is one who doesn’t get paid. If you’re not talented, you won’t succeed. And if you’re not succeeding, you should know when to quit. When is that? I don’t know. It’s different for each writer. Not after six rejection slips, certainly, nor after sixty. But after six hundred? Maybe. After six thousand? My friend, after six thousand pinks, it’s time you tried painting or computer programming. Further, almost every aspiring writer knows when he is getting warmer – you start getting little jotted notes on your rejection slips, or personal letters . . . maybe a commiserating phone call.

Instead of making it as a writer, entrepreneur, spouse, think about pivoting. Jack Canfield told James that he sees all kinds of people succeed in areas related to, but exactly what they dreamed of. Sam Shank (episode #78) lived this when he pivoted from Hollywood to start ups.

In the end Koppelman offered this advice:

“I knew that those two hours in the morning that Dave and I were writing Rounders, were the two hours that I felt most alive in my workday. And it wasn’t a bullshit thing that lasted one day, even when the writing was hard, the actual doing of it is hard…and I wanted that all the time.”  about it feeling good even though it was hard.

And that it was hard matters a great deal. “You have to cover that difficult terrain yourself.” Koppelman says. Jairek Robbins said the same thing, that his dad could have saved him some time and money but without learning on his own he would be short the lesson.


Beyond their enjoyment of podcasting, Koppelman also has a Vine channel,  #319 is quite popular.

“I’m sure there are days when you think the haters are right and you’re not good enough. Days you know it’d be easier to quit. But then you’ll never know what would have happened if you gave it one more push.” – Brian Koppelman

Nassim Taleb calls this the sandpile effect, and it’s a key part of his theories of non-linearity. Imagine you are building a sandcastle (Taleb is “on a beach in Copacabana, in Rio de Janeiro”) but you can be anywhere. One bucket at a time, you add to the castle. Until finally one bucket is one bucket too many, and the whole thing topples.

Taleb’s point is that in life, sometimes that last bucket is random. His example in Fooled by Randomness – appropriately enough – centers on an actor who gets selected for a role and then another role because of the first and so on. That initial selection,the one more push that Koppelman says, or last bucket that Taleb dabbles with could be random. Research has shown that judges can be predicted to be more or less lenient based on their eating habits.

Koppelman likes the Vine videos because of how loose and free they are. A decade ago Jason Calacanis thought this unedited nature was unprofessional but he quickly saw that this was exactly what appealed to people. Maria Popova (episode #89) told James that “allowing yourself the uncomfortable luxury of changing your mind” is one of the things she’s learned running Brain Pickings.

Koppelman’s current project is Billions, which is starting up production now. You can see all the Variety tags for more. He also Vines from the set.

Koppelman wraps the interview telling James that it’s okay to hear people tell you to chase your dreams but that “you have to work ferociously hard.” This is theme of our April 2015 book club choice, So Good They Can’t Ignore You. For example, do you know how Steve Martin became so funny?

He was born that way, no that’s not it. He was passionate and used the law of attraction to will success to him. Wait, wait, that’s not it either.

Martin got a job at Disneyland and spent his summers doing tricks. Then he worked on his magic which transitioned to comedy. But being a Grammy Award winning banjo player, that was a gift right? No. No. No. He played banjo records at half their normal speed so he could play along with the song. Success takes work, super success takes super work.

Dave Grohl also has a bit of wisdom:


Koppelman was on Seth Meyer’s show, you can watch the clip below.

Thanks for reading. If I messed up something other than writing “vine channel” please let me know via text, (559) 464-5393, contact, comments or @mikedariano. There was one great bit that didn’t seem to fit. It was around 33:00 when Koppelman talked about learning comedy. He says that he had to learn to “be mean enough to dispense with the heckler without losing the rest of the audience.”

This shows how deeply he had to understand the craft to do it well and he estimates that it would have taken years and years of late night shows and touring to be able to earn a living from it. To succeed you have to understand things deeply. Jason Calacanis said you have to “know this stuff cold.”

It’s ironic that a post featuring a Michael Douglas movie would lead to another Michael Douglas movie – Falling Down – which is an extreme example of the straw that broke the camel’s back.

*A previous version of this post misspelled Jim Carrey’s name. 

#77 Jason Calacanis

Jason Calacanis (@Jason) joined James Altucher to talk about startups, podcasts, and how surfing is like business. Calacanis is the founder of Inside.com, host of This Week in Startups podcast, and an active angel investor at AngelList.

Their interview begins with Calacanis’s history. He started Silicon Alley Reporter in 1996, as a trade publication focused on New York’s Silicon Alley. Calacanis said that while he was running the company, he felt like he “was the Silicon Alley Reporter” and this identity bothered him. Seth Godin (episode #86) said in that he felt the same way about his company and noted that after he sold it, he felt like a loss of part of himself.

Eventually, Silicon Alley Reporter failed and Calacanis began laying people off. It wasn’t fun but Calacanis tells James that it also wasn’t something to get upset over. He said, “okay, it’s low tide, let’s find another beach.” Like a surfer might drive along the coast and look for parked cars, Calacanis looked at where his Silicon Alley reporters landed – at blogs. At first he was dismissive, thinking that because they weren’t edited, they wouldn’t be good. Once he took some time to examine them more deeply though, he saw that this was exactly why they worked. So he started doing what Gary Vaynerchuk (episode #2) calls “the most important word ever.”

He hustled. Looking at him now it seems like he had hit after hit, but that’s never how it really works. Calacanis had to build up his skills at business building. Jairek Robbins (episode #96) told James that this was something he too had to learn. Jairek was almost perfectly following in his father’s footsteps (Tony Robbins, episode #62) but he had to learn things the hard way, to make his own mistakes and said that he “learned more by figuring it out on my own.” The same was true for Alex Blumberg (episode #70) who told James that he doesn’t know how he solved the problems that come up other than by solving the problems. Ramit Sethi (episode #36) said, “don’t wait for inspiration, test your way to it.” Kevin Kelly (episode #96) said that if you have money you buy solutions, if you don’t you figure them out and learn something along the way. There’s value in the experience of figuring things out.

For Calacanis this meant beginning Weblogs, Inc. a blog network with some notable names then and now, among them, Engadget, Joytstiq, and Download Squad. Finding sites to form a network was easier then Calacanis said, because there was less noise to parse through. You could look at some of the new products on Delicious and find something of value. Now though there are sites like Product Hunt where hundreds are released each week. Calacanis is echoing what Kevin Kelly  mentioned about being lucky. Kelly said, “I lucked out to be at this moment when the digital culture and the nerdy stuff I was interested in became mainstream.” For Calacanis, it was luck in the timing. Five years back and there’s nothing to see. Five years forward and there’s too much.

Part of the avalanche of options is thanks to the access technology provides. “There’s a zillion things you can just do and that’s pretty fantastic.” Calacanis told James. You could setup a blog, an e-commerce store, and a podcast in half a day. Things that took weeks takes days. The cultural gatekeepers are gone – Godin’s idea, not mine – but they are gone for everyone – Vaynerchuk’s idea, not mine. You have to “put up or shut up” as Adam Carolla (episode #25) told James. In the past fewer people could get book deals, start companies, or build websites. Those limits are gone but it means larger crowds. A decade ago Andy Weir (episode #92) tried for three years to get a book deal and got nothing. Now his book is becoming a movie. For every Andy though, there’s a Randy out there that missed.

James asked Jason what someone in their cubicle might look towards as a growing area? Calacanis says whatever you create, he looks for two things in your work.

1. Know your space. “There’s  level of deep, deep obsessive knowledge you need to have of all your competitors. Of all the nuances of their products. Of the history.” He says to James that you shouldn’t be in the smartwatch business if you don’t know the in and outs of the Apple watch and about Pebble’s Kickstarter. “Know this stuff cold.” he says. He likens it to this clip in Rounders, which David Levien (episode #85) said is based on something he really saw and Levien was only able to include this in his movie because he knew his space.

Calacanis calls this “asymmetrical advantage of information.”

2. Do good work. The other thing he looks for is good work, in general. If you have a  well-designed site or good technical programming, then you probably won’t forget that overnight.

The conversation moves to angel investing and Calacanis returns to these ideas. When James asks how someone can get featured on the AngelList (another crowded market) Calacanis says that you should just partner with someone. He goes on to say that if you research one of the syndicate heads you’ll have a better chance. Carol Leifer (episode #66) mentioned the same expectation to James. She said that if someone connects with her and knows that she likes animals, a bit of her history, and has good things to say, she’ll be more likely to work with them.

Calacanis said that one crowded space people shouldn’t worry too much about is reporting and press. Instead of hoping for coverage, people should “take ownership of communicating their ideas.” Build a blog or newsletter and use those mediums to communicate he said.

James and Jason speculate about the future of IPO’s and wonder what role they might play. Facebook was down to almost half of their valuation six months after their IPO and that may have scared some companies away from their own IPO. That’s true, but for the people not involved in the initial investment, it’s valuable to look at the bigger picture.  Two years later the Facebook stock was triple the low. More evidence to not read the daily news which included headlines in the fall of 2012 like “Is this the beginning of the end?” An article at Bloomberg said, that “It might be fatal to your career to be viewed as the last chump to get out.” Ladies and Gentlemen, your daily news.

The problem in the daily news isn’t that the news is bad, it’s that the good stuff is hard to find, especially among the hyperbole. In Fooled by Randomness, Nassim Taleb wrote, “For an idea, age is beauty…For an idea to have survived so long across so many cycles is indicative of its relative fitness. Noise, at least some noise, was filtered out.” Which is a less than applauding introduction to…

Inside.com, Calacanis latest company. It started when he asked, “if people on mobile could read news more efficiently, that would be a great thing for them.” Inside.com then is a snippet view of news stories, organized around themes like Disney or Podcasts. To their credit though, they’ve avoided the “salacious” headlines that typically drive news.

James picks Jason’s brain about his experience building a podcasting network, but Calacanis says it’s really hard. You could “do it as a loss leader” he says. Or as a way to learn from people. But as a business, that situation is harder to figure out.

The end of the interview circles back to Calancanis’s situation when his other startups shuttered and it reminded me of something Marni Kinrys told James. She said that when it comes to being confident, it’s not about being confident all the time. It’s more like a self awareness, an ability to self-diagnosis when you aren’t confident, but want to be, and the know how to build your confidence back up. For Calacanis it wasn’t confidence, but business health. He didn’t always run a successful business but knew when something wasn’t working and what might work instead.

The interview ends with some book suggestions from Calacanis, who says people think he’s smart, but he says he’s just well read. As Charlie Munger said, “I have known no wise people who didn’t read all the time — none, zero.You’d be amazed at how  much Warren(Buffett) reads — at how much I read. My children laugh at me. They think I’m a book with a couple of legs sticking out.”

Jason’s suggestions:


Note: You can now sign up for The Waiter’s Pad Book Club.

Thanks for reading. One final word on luck. Luck is hard to figure out. I’m sure that Jason pursued Weblogs, Inc. because he had the skill to recognize a trend, but there is no success without a bit of luck. As Kevin Kelly said, it’s not that successful people don’t work hard (they do) or aren’t smart (they are) it’s just that they get a bit lucky too.

The Andy/Randy dichotomy will continue on this site after reinforcement from Thinking Fast and Slow and Fooled by Randomness. Both books talk about our mistake in looking at the numerator rather than denominator (availability bias). That is, we take notable examples, like Andy Weir and we think that he represents a class (part-time fiction writers). Rather, he’s the exception. There are many people writing space fiction who didn’t make it, we will call them Randy.

#97 Gretchen Rubin

Gretchen Rubin (@GretchenRubin) joined James Altucher to talk about habits, happiness, and answer why she was so unhappy in the first place (she wasn’t, and gives a good reason).

Rubin is the author of a trio of books that James seems to have enjoyed. The Happiness Project, Happier at Home, and her latest, Better than Before. In that final book Rubin says that she discovered that there is no one sized fits all approach to solving our habit (or any) problems. It takes a lot of experimentation and mindfulness, something that Brad Feld (episode #91) mentioned in his interview too. It’s a theme among the podcast guests that you have to experiment to find your own solutions. In her interview Rubin admits that she found that novelty and challenge made her happier while adventure and travel did much less for her.

One of Rubin’s discoveries during her exploration of habits was that people have range of aptitudes for creating habits. Like some people are better at cooking, or building websites, some people will be better at creating habits. Taking a moment to think about the habits you want to build is good, and it’s what Scott Adams called the right kind of selfish.

If you do selfishness right, you automatically become a net benefit to society. Successful people generally don’t burden the world. Corporate raiders, overpaid CEOs, and tyrannical dictators are the exceptions. Most successful people give more than they personally consume, in the form of taxes, charity work, job creation, and so on.

runningmommyRubin says that beyond that “happier people are more altruistic” and “when we’re unhappy we tend to get defensive and isolated and pre-occupied with our own situation.”

This conversation reminded me of a recent Facebook post from a friend. She’s one of the many parents who faces the trade-off of personal well-being and taking care of your kids. It’s important to have some kind of good selfishness.

Rubin began this journey of habits, health, and foremost happiness not because she was unhappy, but rather “I was taking my happiness for granted.” She wanted a better sense of appreciation for the things she had. Past guest Wayne Dyer has built his books on this idea, noting that even if all you have is your breath, or your mind, you still have something to be thankful for.

So, Rubin began a year long project of building up a collection of habits that would let her “have a greater appreciation for what I already had.” One discovery was that when she built habits, time would either speed up or slow down. It can “dampen our emotional reaction to things” she tells James. For Rubin this meant that the anxiety producing act of driving became less angst filled when she did it more often. Examples like driving were some of the low-hanging fruit examples that brought her happiness.

She also saw that “energy makes everything easier.” She noticed that if she had good energy levels, she could act in the way she wanted much more easier. Daniel Kahneman writes that “self-control and deliberate thought apparently draw on the same limited budget of effort.” We want to take a certain course, the one of least resistance as worn smooth by our habits. If this course isn’t what we want though, it takes some effort to change.  It reminds me of sledding with a young child. You get on, aim away from the tree/creek/other people, only to have your sled turned by the well worn grooves of other riders. You dig your heels in to change course. That mental heel digging takes energy. Willpower takes energy in the same way that solving a difficult problem would. If you want to do something different, you need to summon a surge of energy or build new habits that don’t require that surge.

Rubin also found that the acting and feeling dichotomy echoes what A.J. Jacobs said. In episode #94 Jacobs quoted Millard Fuller saying, “It’s easier to act your way into a new way of thinking than to think your way into a new way of acting.”  Rubin found her experiences similar, telling James, “a lot of times people feel we act because of the way we feel, but in fact to a very great degree, we feel because of the way we act.” Kahneman also found that just smiling or frowning can affect your thinking.

nestledlistRubin continued her experiments, picking up pieces and seeing their fit like a child might put together a Lego house, then a boat, then a castle. She found that children know how to make friends easily but adults find hard it more difficult. “It’s really hard to make friends as an adult” she tells James. Our problem, Rubin suggests, is that we don’t take a moment to ask why it’s so hard. She says that we don’t – in the words of Jack Canfield (episode #90) – take our whacks at the tree. “Keep asking why,” Rubin says, and you’ll find an answer.

James addressed this in a very specific way in episode #223 of his Ask Altucher podcast; “How Do I Execute?”. He said that execution “is just a subset of ideas.” James goes on:

When you have a good idea, the next day make your list of ten possible next steps to execute on this idea and all of these steps should be stress free.

A more explicit tip Rubin suggests is to find triadic closure, which I had to find on Wikipedia because it sounded too wild to believe (the term, not the principle). The idea is that you should make friends with your friend’s friends. If you know Kim and Kim knows Dan, then you should try to become friends with Dan. Rubin admits that it seems odd thinking about friendship in anything less than organic terms, but if it’s your best thinking that’s got you where you are, maybe you need to change your thinking.

Another tip that Rubin has is to start a group. It doesn’t matter if it’s a children’s literature book club. If you do choose a group, make sure it’s something you’re really interested in. Adam Grant (episode #73) told James that people who volunteer for causes they don’t care about, or aren’t invested in, get burned out much faster.

There was the month – NaNoWriMo – where Rubin wrote a novel. There was a month of trying to be better in her marriage and with her kids. She found out that nagging doesn’t work, that six second hugs are great, and that it takes thoughtfulness and mindfulness to fight right. After her experiments she tried to be more mindful of things, to the way she talked with her kids to the way she postured her body during writing. She experimented her way to four big ideas for happiness.

  1. Growth
  2. Feeling Right
  3. Feeling more good things
  4. Feeling less bad things

James asks what a “cubicle dweller” might do to make their life happier and Rubin suggests that you start to list out the things in those four categories that would make you happier. What are some of the more good things and some of the less bad things? If you’re reading this and listening to the podcast there are a whole host of of shows you could dive into. Here are a few of my current favorites.

  • Gary Vaynerchuk (episode #2) also has a Q/A podcast.
  • Build and Launch. Justin Jackson launches a product every seven days.
  • Stephen Dubner has a Freakonomics podcast.

Finding podcasts actually became a solution to a friend of Rubins. At first her friend thought she hated her job. After diving deeper into the problem though, she realized that it wasn’t her job as much as it was the commute. Filling that time with audiobooks and podcasts changed her view. This is what Stephen Dubner (episode #20) calls solving a small problems. Small problems are easier to solve because they have easier solutions. He’s putting the same ideas of Rubin and Canfield into effect.

A personal story of my own was when my first daughter was born. I realized – in hindsight of course – that there were certain days I lost my temper. Why was that? It turned out, the reason I was so short with my daughter and wife was that my legs hurt. My hips were misaligned because my hamstrings were too tight. My hamstrings were too tight because I was sitting down too much. If this were a corporate flow chart it would look like this:

tight hamstrings > crooked hips > back pain > general pain > discomfort > short temper

Only after I realized this sequence did I begin to understand how to solve my problems. Diving into deeper good solutions like this is told in the story of cholera in 1850’s London. A middle of the century outbreak was causing hundreds of people but no one knew the answer. Not until Dr. John Snow began asking questions, diving deeper and deeper, did a solution appear. The problem was the water. By disconnecting a single pump handle, the outbreak was squelched.

If you takeaway anything from Rubin’s interview, it’s that you should start tracking something because “anytime we start monitoring something we do a better job with it.” she tells James. Track, experiment, change, tweak, repeat. Also, pick up a book or two from Rubin for a good idea on where to begin your own happiness project.

Thanks for reading. Mike – @mikedariano.

If you want to join a group, The Waiter’s Pad book club will be starting soon. If you have book suggestions or requests, let me know.

#49 Kevin Harrington

James Altucher interviewed Kevin Harrington (@HarringtonKevin) to talk about marketing, infomercials, and the nuts and bolts of selling nuts and bolts.

Altucher begins the interview by asking about all the products Harrington has been involved with, and it’s a lot. Like James, I was struck by the number I recognized considering that I don’t watch late late night television. Kevin’s been involved with the George Foreman grill, the NuWave Oven, Ginsu knives, Tony Little’s products, Paris Hilton, the Medicus golf club and the list goes on. Kevin pegs the number of infomercials he’s been involved with at nearly 700.

One of Harrington’s early partnerships was with Tony Little. He was so successful that he was “buying homes and real estate and, you know, unbelievable things and, you know, antiques and art and all that kinda stuff – fancy cars.” One of the guys on Kevin and Tony’s team sees this and thinks that he wants to do it too. So he goes off and starts a company called Beachbody – the company behind P90X – which now does over $400 million a year and that man’s name was Carl Daikeler.

Then James and Kevin talk about the Flying Lure, a 500 million piece seller (this phrasing slipped past me until later in the interview, just wait). The Flying Lure inventor, Alex Langer, says that the idea came to him after he “got skunked for 2 straight days of fishing.” He then cut up a Coke can and glued the pieces together for the first iteration of the lure. Three years later he met Jim Caldwell who took the idea to National Media Corp. where Harrington was president. From there Kevin put together $75,000 worth of TV spots, but tells Alex he needs one hundred testimonials. He needs; consumer, professional, editorial, celebrity, and documentation testimonials.

This range of testimonials works well because it corners the market on a psychological idea known as the availability heuristic. “The availability heuristic is a mental shortcut that relies on immediate examples that come to mind. The availability heuristic operates on the notion that if something can be recalled, it must be important.” Marketers like Kevin want to provide enough examples, that one of them will come to mind when thinking about a product, like The Flying Lure.

Imagine a hypothetical situation where you need to buy a new computer. You check Consumer Reports, The Wire Cutter, you look around at coffee shops. It’s clear after your research that Apple is the clear choice. You then tell your brother about this and he tells you about the lemon of a computer his Apple was. His review should have very little impact, it’s only one experience of many. What research has found though, is that because this information is more recent and comes from someone we interact with, we are more likely to weigh it heavily in our decision. For Harrington – I’m supposing here – the idea is that if your brother is a fisherman that doesn’t like the lure, they provide a better fisherman who does. If he is an engineer that explains it can’t work, they provide a better expert who says it does. Whatever area you might face an objection, they want a more available, and favorable, suggestion that says it works.

Before any of the testimonials can work though, Harrington says you have to “tease, please, and seize” the person who is listening. In the interview he gives the example of the meatball sandwich. “If I’m selling a cleaning product, you’re gonna see a guy eating a meatball sandwich with a big drop of sauce all over his beautiful $100 tie. Has this ever happened to you? And that’s – and, yes, it has, and by the way, I’m gonna watch to see how they solve that problem. So show me a problem, hit me upside the head, tease me.”

After getting their attention, you need to please them, and show the benefit, the magical transformation. “In acne, it’s pizza face to clear skin. In weight loss, it’s 280 pounds to 120 pounds. It’s, you know, show me somebody that was poor, now they’re rich.”
After the testimonials are arranged and the tease, please, seize sequence coupled together, it’s time to buy TV time, which can be expensive. Harrington says that it’s 30-50% of the cost of goods. With all the numbers he gives on the episode my best guess for the cost breakdowns on The Flying Lure are; $10 to TV, $1 to Alex the inventor, and $4 for the packaged goods. Harrington says the rest goes to the lawyers, accountants, and other people behind the scenes that make it all happen. About that “500 million piece” language, that’s how many total pieces. In all only 25 million kits were sold. Still a staggering number but something about the funny expression made me wonder about the other things Harrington was saying.

Then James and Kevin get to the celebrity endorser that I was most interested in hearing about, George Foreman. I remember looking up Foreman the boxer after seeing Foreman the grill salesman. At first Foreman didn’t want to do it, saying he wasn’t “interested in toys.” His wife was the one who tried the grill and convinced him after cooking a burger for him on it. The grills bearing his name went on sale in 1994 and in 1999 Foreman was bought out for $137 million bringing his estimated total compensation for the grills to almost $200 million.
The other media mogul from Foreman’s generation is William Shatner, the spokesperson for Priceline.com who was initially paid in Priceline Stock. The details on Shatner’s fortunes are more ambiguous than Foremans, but here is what the Priceline stock has done.
Harrington hasn’t been on Shark Tank in a long time – that I can remember at least, and I watch most weeks – but he’s been doing his own shark tanks. “You know, like I go into corporations and I do – I create Shark Tank style events. You know, I went into a major corporation like AT&T, had 300 senior executives, break them into 30 teams of ten and we take 30 pitches over the day and we come up with new ideas for AT&T. That’s one style of event, so that’s cool. I’m planting a seed, building a whole new business enterprise corporately. Then I do the same for commerce kind of events and I do entrepreneurial organizations.”
Then they bring up Gary Vaynerchuk (a past podcast guest) and Harrington says he’s made millions of dollars on investments in companies like Uber. Somehow I didn’t get any of this when he was last on Altucher’s show.

Harrington ends the interview by telling Altucher to keep his eyes on the NuWave Oven which uses infrared technology, and the Ronco vertical grill. If you want more from Kevin Harrington he has a new book out, Act Now: How I Turn Ideas Into the Next Million Dollar Product.