Timothy Ferriss's Blog, page 92

5 Tools I Use For Faster And Better Sleep

This short (~20 min) episode covers the latest tools, gadgets, and tactics I’m using for faster and better sleep. Enjoy!

Listen to it on iTunes.
Stream by clicking here.
Download as an MP3 by right-clicking here and choosing “save as”.

As a lifelong insomniac, I’ve tried everything, and here are some of the critical few that make the cut:

Chili Pad
Hanging upside-down or traction 
Sleep Master sleep mask and 3M E-A-Rsoft FX ear plugs
Yogi “Soothing Caramel Bedtime” tea
Visual overwriting (e.g. Tetris or Escape to River Cottage, Season 1)

Here are a few other things that I think about when optimizing sleep and recovery.

Want to hear another podcast from that focuses on some of my favorite tips and tricks? — Listen to my podcast about The 5 Morning Rituals That Help Me Win the Day. In this episode, you’ll find the five things I’d like to accomplish within the first 60 to 90 minutes of an “ideal day.”

QUESTION OF THE DAY: What change or decision has most improved your quality of sleep?  Please share in the comments!

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Investing in securities involves risks, and there is the possibility of losing money. Past performance is no guarantee of future results. Please visit Wealthfront dot com to read their full disclosure.

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Inside an “Anything Goes” Sex Club

(Photo: Stelladiplastica © Medhi, Zivity.com)

“Those who are easily shocked should be shocked more often.” – Mae West

In this post, we’ll look two alternatives to monogamy: an “anything goes” sex club and living with three lovers at once.

It’s very graphic, definitely not suitable for work (NSFW), and guaranteed to offend most of you.

If you’re chomping at the bit to express mock outrage, please check this out instead. For the rest of you, I’m hoping the below is hilarious and somehow helpful.

Lifestyle design is, after all, about a lot more than work.

And if anything below shocks or appalls you, please ask yourself: why does this make me so uncomfortable? Dig into the discomfort. Looking inward before lashing outward is good for the world.

Now, on to the taboo.

Context

As some of you know, I’ve been conflicted about monogamy for a long time. I love intimacy, but my biology craves novelty…

So, what the hell is a guy to do? There is reality as we’d like it to be, and then there is reality.

This is where Neil Strauss often enters the picture. I’ve known Neil for years. He’s a seven-time New York Times bestselling author, arguably best known for The Game. In that book, he enters a subculture of pick-up artists as a hopeless nerd and comes out able to conjure threesomes on demand.

Not surprisingly, Neil went on a tear of sexual hedonism after his transformation, and many men read his book hoping for the same.

Then… Neil fell in love. Things got complicated once again.

On this blog and in the podcast, he and I have talked about kickstarting creativity and his genius writing process. But at night over drinks, we still discuss what two guys usually discuss: women. The same questions come up a lot:



– Are humans really designed for monogamy? Is it possible or even desirable?

– Should you choose excitement over intimacy?

– If you’re a driven type-A personality, can you really have both with one person?

– Would life be better if you could sleep with anyone you liked at any time?

– What if you could get a hall pass every once in a while?

Neil has spent the last six years attempting to answer these questions, and the result is a brand-new book called The Truth: An Uncomfortable Book About Relationships. I’ve been reading drafts for months.

This post includes two of my favorite stories from his experiments, adapted and embellished for this blog.

It’s written from the perspective of a male, of course, but many women grapple with similar questions. These are challenging times.

MY SELFISH REQUEST: Please share in the comments what has worked for you! I’m a simple animal living in a confusing world. How have you navigated the above questions?

In the meantime, enjoy the debauchery…

Enter Neil

Several years ago, I was in a relationship with a fantastic person. She was great. Yet I was miserable. I felt trapped. Being romantically and sexually with one person for the rest of my life–at least four decades, barring any cruel twists of fate–made no sense.

First, there was the science: I had interviewed evolutionary biologists, anthropologists, historians, geneticists, and more. I could not find a single shred of evidence supporting the theory that monogamy was natural. And when I talked to a professor who wrote the only major research paper I could find suggesting monogamy was good for civilization, even he admitted, “If humans, just by nature, mated for life and there were a very tight pair-bond, then we wouldn’t need all these marriage customs.”

As Stephanie Coontz, the world’s leading marriage historian, explained when I spoke with her: ”…Now you don’t have to [accept traditional marriage and family as a package deal]: It’s literally pick and choose. Cut and paste the kind of life you want. Family life and love relationships are essentially becoming a build-your-own model.”

So I decided to build my own relationship, and after some thought, this is what I came up with:

It can’t be sexually exclusive, which rules out monogamy.
It has to be honest, which rules out adultery.
It has to be capable of developing romantic and emotional attachment, which rules out being a permanent bachelor.
It has to be capable of evolving into a family with healthy, well-adjusted children, which rules out unstable partners and lifestyles.

Then I started experimenting. Some turned out far better than others. Let’s start with one of the winners.

THE “ANYTHING GOES” SEX CLUB

Everywhere I look while traveling to Paris, I see young couples pushing sleeping children in strollers, carrying blanket-wrapped babies in their arms, hurrying along superhero-backpacked toddlers.

Each family makes me think of Ingrid, the girlfriend I broke up with, and the future I ruined. I wonder what Ingrid’s doing, who she’s doing it with, and if she’s happier living without my wandering eyes and ambivalent heart.

In Paris, however, everything will change. I will finally find the freedom I’ve been looking for.

First, there is Anne, a woman who’s been flirting with me on Facebook. She’s waiting in the hotel room when I arrive. She’s slender and toned, with dirty blond shoulder-length hair, minimal makeup, and boyish clothes. As I approach her, she looks deeply and mutely into me with quivering brown eyes. I take a step toward her, brush her hair aside, and we kiss.

We disrobe. Get in bed. Make love. Spoon. And then she says salut. It’s the first word we’ve exchanged.

Then, there’s Camille, an open-minded Parisian who some new swinger friends made me promise to get in contact with.

“Hi Neil. I’m meeting my friend Laura, who’s American just like you,” she texts. “She wants to go to a great switch club and I promised I’d get in trouble with her. Do you want to come with us?”

“Is it okay if I’m with a date?”

“Dump the girl. There’ll be plenty of dates for you there! And they all want to have sex :)”

This switch club sounds like a goldmine of open-minded single women. The only problem: I want to bring Anne.

“If you have to bring her, use the ‘We’ll just have a drink and watch’ technique,” Camille relents. “That’s how my boyfriend got me there in the first place, and look at me now! The club is by Montmartre. Give me a call after dinner.”

In my monogamous relationship last year, my credo was to say no. Only by saying no to others could I protect Ingrid’s heart. But now, I am saying yes—to everyone, to everything, to life. Because every yes is the gateway to an adventure. Whatever I am heading toward, it is a relationship that operates out of a place of yes.

At dinner that night, I do exactly as Camille instructed. Anne and I are with two women I met on a European press tour a few years earlier: a German fashion photographer and a Swedish designer. They spend most of the meal gossiping about people I don’t know.

“We don’t have to do anything,” I explain to Anne. “Let’s just plan on having a drink and watching, and we can leave right away if it’s lame.”

“I’m a little tired,” she replies, her voice barely audible. Throughout the day, she’s barely spoken. Instead, she’s attached herself to me energetically, gazing at me almost constantly with big, vulnerable, barely blinking eyes. I get the sense that she wants something from me or may already be getting it from me. “Is it okay if I go back to the hotel?”

“Can we come?” the fashionistas interrupt.

“You can go with them if you want,” Anne tells me softly.

It’s hard to read Anne. I’m not sure if she’s legitimately tired or just uncomfortable with the suggestion. “Are you sure it’s all right for me to go?”

“I don’t mind,” she replies.

I study her face to make sure she’s sincere, that it’s not a test to see if I’ll choose her. She appears placid and unconcerned. I ask three more times just to make sure.

“She said you could go!” the German photographer snaps at me.

We drop Anne off at the hotel, and she gives me a deep kiss and walks off. It’s a good sign: Letting your lover go to a sex club alone is actually a much more open-minded feat than going with him. As the taxi speeds away, the German photographer loops her arm in mine.

I’m determined not to wreck this orgy like all the others [Editor’s note: elsewhere in the book].

We arrive at the club just after midnight. I spot Camille instantly. She has long brown hair worthy of a shampoo commercial and skin so smooth and flawless that a metaphor to an inanimate object, like a pearl, would hardly do it justice.

She’s standing with two other women: Laura, her American friend, who looks like a burning candle—long and narrow, with a white pantsuit and a shock of short blond hair. And Veronika, a haughty beauty from Prague with lips like cylindrical sofa cushions, flowing brown hair, an overdeveloped nose, and a tall, thin, sensuous frame that reminds me of the actress Jane Birkin.

“Do we have to put on robes or towels when we go in?” I ask Camille, unsure what protocol is for places like this.

Camille looks at me like I’m crazy. “No, we just wear our clothes.”

That’s a relief. Despite my desire to be open, evolved, and shame free about sex, I’m still not totally comfortable with the sight of my own body. The first time I ever had sex, I was too embarrassed to remove my shirt. And the second and third times as well.

Behind us in line, there’s a Frenchman with a shiny suit and slicked-back hair. He looks like a shady businessman who snorts a lot of cocaine. “Since you have so many girls, is it okay if I come in with you?” he asks.

The club has a rule that all males must enter with a female—and I’m standing there with five of them like a glutton. I suppose this is what I missed when I was dating Ingrid: options, variety, adventure, discovery, novelty, the unknown.

“I don’t know,” I tell him. “It’s my first time here.”

As we wait, Camille and Laura discuss sharing toys, by which they mean boys. “Is your boyfriend coming?” I ask Camille.

“No.”

“Does he know you’re here?” I’m asking not to judge her, but because I’m curious how their relationship works.

“No.” She smiles guiltily. Clearly, having an open relationship is no cure for infidelity. Almost everyone I’ve met in the scene so far has transgressed even the minimal rules of their supposedly open relationship.

Perhaps the problem with most relationships is that the rules start to become more important than the values they’re supposed to be representing.

Eventually two of Camille’s toys arrive, both in designer jackets and skinny ties. They introduce themselves as Bruno and Pascal. Bruno looks like a clean-cut college athlete, while Pascal, with thin-framed glasses, tight curls, and slow, well-mannered gestures, looks like an intellectual dandy.

Unlike the highly sexualized crowd at Bliss [another sex party], the men and women here aren’t divorced weekend warriors dressed like porn stars. Aside from the slick-haired businessman behind us, everyone here seems young, hip, well dressed, and silicone free. They don’t look much different than the crowd outside an exclusive nightclub. Evidently, after a night on the town, they come here for dessert. As the line starts moving, Laura takes pity on solo slick guy and invites him to come in with her.

“Do you know how I can tell these people are barbarians?” the German photographer says to her friend. “Look at their shoes. I wouldn’t wish a single pair on my worst enemy.”

I glance back nervously and think about ways to slip away from them. But it’s too late: We’re being let inside.

When we enter, a hostess asks us to check our jackets (which for some reason leads to sniggers from the fashionistas), then gives me a card that she explains will serve as my tab for the night. Veronika removes her blazer to reveal a loose-fitting backless dress that, when her stride is long, would get her arrested. “She will be my first fuck tonight,” Pascal tells me confidently as I stare mutely at the tan expanse of Veronika’s back.

We walk downstairs to an empty, low-lit dance floor dotted with stripper poles. The twenty or so people in the room are clustered against a bar, drinking away their inhibitions. Katy Perry’s “I Kissed a Girl” is playing. It seems so . . . obvious.

At the end of the anteroom, there’s a black door that leads to the fun. After her friends have drifted into the rooms behind it, Camille takes my hand and offers to show me around. “What about my friends?” I ask.

“They’ll be fine. Are you coming or not?”

I look over and they seem deep in snide conversation, concealing their discomfort by increasing their arrogance. I should invite them to join us, especially since I brought them here. The last thing I want to do, however, is walk around the orgy with them making obnoxiously loud comments about how everyone’s sexual techniques are so last year.

• • •

Behind the black door, Camille and I slowly wander through sunken living rooms and small porthole-fitted chambers, all in copious use, until we arrive at a space that consists of just an enormous bed and a narrow walkway along the front wall.

Most of the women on the megabed are completely naked while the men are still wearing dress shirts, ties, and pants. However, their pants are all unzipped or lowered and their junk is hanging out. Dicks are everywhere. Even the guys who aren’t with women are walking around the room with expectant cocks dangling in the air in case someone has a need for them. I’m the only guy who’s zipped up.

In the bottom right corner of the bed, Laura is on all fours with her dress up. Bruno pulls out of her and parks in Camille’s mouth while Pascal, true to his word, fucks Veronika against the wall. She’s standing up, facing frontward with one leg raised and her face flushed, in a pose that, if photographed, would incite a million sticky nights.

I don’t know what to do, how to get involved, or what the rules are.  This is the closest to a free-for-all I’ve ever seen.

So I sit in the empty space on the mattress in front of Laura, who’s still posed on her hands and knees expectantly. “Thanks for letting me come here with you guys,” I tell her, because I feel like I need to say something.

“Is this your first time at a switch club?” she asks astutely. This is probably the stupidest place I’ve tried to make small talk since the last orgy.

“Pretty much.”

As we’re talking, the creepy businessman from outside the club materializes behind Laura and rubs her pussy. Then he scoots under her like he’s repairing a car and starts eating her out.

“Is that cool with you?” I ask her. “I can tell him to stop if you’re not comfortable.” Here I go again: taking care of everyone’s needs but my own.

“That’s so American of you to say,” she laughs.

“What do you mean? How is that American?” I don’t even understand the comment: She’s American herself.

“No one’s ever asked me that before.”

“But I thought maybe—”

“I just want a cock in me.”

This is the kind of woman I fantasized about as a teenager: an indiscriminate one. And more than anything I’ve experienced so far, this seems like free sex–because there’s no spiritual baggage, drug baggage, or even much relationship baggage around it. In fact, there’s no baggage or encumbrances whatsoever, just randomly intersecting body parts. And now that I’m in the midst of it, I’m terrified. It’s so shockingly . . . open.

It’s not society that holds us back, it’s ourselves. We just blame society because not only is it easier but it’s a nearly impossible weight to move. This way, we don’t actually have to change. I thought I was fighting the system, but perhaps all I’ve really been doing is fighting myself.

Meanwhile, the slick-haired guy stops licking Laura and appears to be going for a home run.

I realize this is very crude, but the story takes place in a sex club. What else am I supposed to describe? The chandeliers? There’s nothing going on here but sex.

“Can you make sure he puts on a condom?” Laura asks.

“Okay,” I reply over-enthusiastically, grateful for the opportunity.

I have a job to do now. A purpose. I am the condom police. I watch him carefully to make sure he puts the rubber on. Then I worry that I’m creeping him out. But I won’t be swayed from my very important duty: no protection, no service. That’s right, sir, roll it on all the way. Otherwise I’m going to have to ask you to step out of the bed.

“It’s on,” I tell her with an air of authority,

As he thrusts inside her, Laura’s face swings closer to mine. Now’s my chance, I think, and I start making out with her.

And that’s when I realize: No one else here is making out. How many dicks has she had in that mouth tonight?

So I pull away. It’s time to say yes and unzip. I kneel so that my crotch is level with her head. And sure enough, she takes it in her hands, guides it into her mouth, and starts sucking.

“What do you like?” Laura pauses to ask.

Good question. I like this. What’s better than a blow job? Or does she want more specific instructions? Perhaps they have names for different blow jobs here—the spit-shine, the round-the-world, the confused American.

Like anything, I suppose sexual freedom is a learned art. I still need more experience to get comfortable.

Suddenly, I see Pascal’s head appear over mine. He whispers in my ear, “Veronika wants you.”

It’s music to my ears, especially since things with Laura feel awkward. I know she has an any-cock-will-do attitude, but I have a sneaking suspicion that my cock isn’t quite doing.

When the businessman finishes, Laura makes her escape. But instead of Veronika appearing, Camille kneels in front of me and takes Laura’s place with more enthusiasm. I’m not fully present because I’ve been stuck in my upper head, so I look around the room and notice a woman lying spread-eagled in front of me. I take her hand and start massaging it, and she massages my hand back. I move my hand between her thighs and start playing with her.

I’m starting to get comfortable here. Finally, I’m actually part of an orgy—awake, accepted, alive. I rear up tall and look around. Everyone is fucking and sucking.

Perhaps my previous disasters in CNM (consensual non-monogamy) have actually been necessary experiences to get comfortable at these things, learning lessons on the road to orgy mastery.

Suddenly I hear a guy’s voice exclaim loudly, “Tu es sur ma jambe.”

Nearly everyone on the megabed starts laughing.

Evidently I’m kneeling on some guy’s leg. I slide out of his way and notice Veronika crawling toward me on the mattress. I drink in her unique amalgamation of devastating beauty and awkward innocence, and I instantly harden.

I make out with her passionately. I don’t know why I keep touching people’s filthy lips, but I crave the intimacy and connection more than the anonymous sex. Maybe I am polyamorous—because it’s not just free sex I’m searching for, it’s free romance, free connection, free relationships, free getting-naked-with-someone-you-enjoy-and-who-enjoys-you-and-then-getting-to-know-each-other-even-better-afterward.

I seriously need to gargle with Listerine when I leave this place.

Meanwhile, Bruno has appeared out of nowhere and started having sex with the spread-eagled woman.

I pull back and look at Veronika’s face, and she bites her lower lip in response. There’s so much heat between us and we’ve only just met. I hope it isn’t because she was abandoned by her father (long story).

I run a finger across her lips and she sucks it into her mouth and . . . oh god, I feel like I’m about to . . .

But I don’t want this to end, so I pull out of Camille’s mouth.

“Let me suck you!” she begs.

This is the best night of my life.

I’ve finally entered the world I’ve been reading about in porn magazines and watching in adult movies since puberty. Just as women are trained by the media and society to look for their Prince Charming, men are conditioned to look for their nasty slut. Not for a marriage, but just for an adventure. Both are fairy tales, but a Prince Charming is nearly impossible to find, because it’s a lifetime illusion to sustain. It takes only a few minutes to play the role of nasty slut.

The only thing keeping me from fully enjoying this sexual paradise is the guilt: that Anne is in the hotel worrying, that the fashionistas are angry, and that because I’m liking this so much, it means I’m a sex addict, as is everyone else here. The counselors back at rehab have really done a number on my head. I used to be worried just about sexually transmitted diseases, but they’ve turned sex itself into a disease. And now, any time I’m giving myself over to pleasure, I hear a therapist’s voice in the back of my head telling me I’m avoiding intimacy.

Just as I promised my friend Rick Rubin I’d go all in on addiction treatment without doubt, I need to go all in on freedom without guilt. The answer will become clear over time: Either I’ll hit bottom, as others predicted, or I’ll find a solution that works for my life, as I hope. I need to get out of my head and be present for this experience. And to remember why I’m here: not just to have a lot of sex, but to find my relationship orientation and like-minded partners.

As my eyes meet Veronika’s again, I notice a dick hanging in my peripheral vision like a cloud covering the sun. Its owner says to me in a thick French accent, “All the girls here, they have been sucking your dick.”

“I guess so.”

“Do you like having your dick sucked?”

It seems like an obvious question, but I reply anyway, “Yes.” I try not to make eye contact. This conversation definitely isn’t helping my staying power.

“Would you like that I should suck your dick?”

“Oh, no thanks.” I don’t know why, but the situation seems to call for politeness. “I’m good.”

I suppose if I technically wanted total freedom, I’d let him go to town. But, I realize, the goal isn’t sexual anarchy. It’s that I want the rules around my sexuality to be self-imposed, not externally imposed. That’s the key difference—perhaps in everything.

The goal, then, is liberation: to be the master of my orgasm. I don’t want my partner to own it, which would be monogamy, but I also don’t want the orgasm to own me, which would be addiction.

My new admirer has inadvertently given me a gift. Though he doesn’t say anything else, I keep seeing his dick—on my right side, then my left, then a foot above me—as if he’s hoping that by just dangling it around me, at some point I’ll decide to show my appreciation. That seems to be how things work here. Maybe this is where all the women hang out who actually like it when guys text photos of their dicks.

A Valkyrie with long blond hair and missile breasts clambers onto the bed with her boyfriend. I eye-fuck her to get back into the spirit of the orgy. She holds my gaze. But before I get a chance to do a thing about it, Bruno appears out of the blue and starts fucking her.

I don’t know how he does it. This must be his tenth woman. Suddenly I remember that Camille has been down there sucking me for half an hour straight. I put on a condom, lie down, and move her on top of me.

Camille rides me as Veronika positions herself over my face. I am smothered in woman. If this is happening right now because my mother smothered me, then I owe her a serious thank-you.

Suddenly, a loud, condescending German voice fills the room: “Where is he?”

I tilt my head back and see an upside-down image of the fashionistas standing against the wall, staring into the mass of bodies.

“It’s just like him to do this to us!”

I try to shield myself underneath the women so the fashionistas don’t spot me.

“Let’s just leave without him.”

Their voices cut through the room, killing all sexuality in their path.

“So selfish.”

For a millisecond, I consider stopping. I should probably get back to the hotel and check on Anne anyway.

Then I think, No. This is amazing. I don’t want to stop this. So I’m selfish. Let me be selfish. They can leave and I’ll deal with it later. I’m learning how to take care of my own needs for a change.

In moments like these, the true nature of one’s soul is revealed.

“Let’s switch,” Veronika suggests. This is a switch club after all, so I slide out of Camille so she can swap places with Veronika. However, as soon as Camille’s lower orifice is free, Bruno is in there. The guy never misses an opportunity. I’m sure he’s a great businessman in the outside world.

Veronika slides her body over mine, her skin rubbing against my clothing, her back arched so we can see each other’s faces. I switch condoms and slowly enter her. We move against each other sensuously. Time slows. We fall out of sync with the rest of the club and into each other.

I gaze deeply into the world in Veronika’s eyes and she into mine—and it feels like love. Not the love that is a thought that comes with expectations of commitment and fears of abandonment, but the love that is an emotion that makes no demands and knows no fear. I’ve found, for a moment, love in a swing club.

Connected sex is a spiritual experience, but not in the way new-age western Tantra devotees describe it. It is spiritual because it’s a release from ego, a merging with the other, a discorporation into the atoms vibrating around us, a connection to the universal energy that moves through all things without judgment or prejudice.

Thus, orgasm is the one spiritual practice that unites nearly everyone on the planet, and perhaps that is why there’s so much fear and baggage around it. Because they were right both in rehab and the pseudo-religious sex cults: It is sacred.

And every orgasm. Is in itself an act of faith. An attempt to reach out. And just for a moment. Relieve our separateness. Escape from time. And touch eternity. And, yes!

As she drenches the mattress, I fill the condom.

Not only did I find love at an orgy, I think I found enlightenment.

ENLIGHTENMENT COLLIDES WITH “REAL LIFE”

A MONTH LATER, IN SAN FRANCISCO

“I moved in with three girlfriends and it’s been a complete disaster. No one’s getting along.”

That voice is, unfortunately, mine. I am making an emergency call to the smartest person I know in the world of polyamory. I would caution against, however, judging his level of intelligence from the name he goes by. It is Pepper Mint.

Really.

Months have passed since I made the decision to find a free relationship, and I eventually found three of them. So with a relationship roster that looks like a visit to Disney’s “Small World” ride–Anne, from France; Belle, from Australia; and Veronika, from the Czech Republic–we all decided to move into a house in San Francisco together.

And while months have passed since my decision to broaden my relationship horizons, unfortunately only a day has passed since we all moved in together. Problems came up that I just couldn’t anticipate, that weren’t covered in any books on the subject, that even the experts didn’t mention.

Like this one: The four of us traipse down the stairs, hungry and excited for a good meal. I get in the driver’s seat of the car. And… three women stand in front of the passenger seat of the car, looking confused and uncomfortable. They look to me to make a decision. But how can I pick favorites? That’s not going to help us live in equality this weekend. Eventually, we decide on a rotational system for the front seat: Alice will take the front seat now. Next time, Belle gets the front seat. Then Veronika.

It’s as ridiculous as it sounds.

The automobile was clearly designed by monogamists.

And that was just the beginning: Even though all three women were excited about being in a group relationship, and two of them had already had related experiences, by the end of that first night all together, I felt like I was on an episode of The Bachelor. Competition reared its ugly heads at a party that night, at which all three of them wanted to leave at different times, Anne became jealous when anyone else touched me, Belle became upset when I told her to be careful about touching me because of Anne, and Veronika was irritated with all the drama.

There’s a term popular in the poly world: compersion.

It was coined supposedly at the Kerista commune in San Francisco decades ago. And it’s the idea that if the person you love is with another partner, rather than feeling jealous, you can feel happy for them because they are happy. And if you love someone, you should be glad that they’re happy, whether or not they’re experiencing it with you, right?

Compersion is evidently a lot harder to feel than it sounds. And it already seems pretty difficult to feel.

So that night, in light of the clear and total absence of compersion, I ended up sleeping on the couch so as not to hurt anyone’s feelings.

The moral thus far: Be careful what you wish for.

So now, the next day, I was on the phone with Pepper Mint, begging for help. Things could only get better from here.

“You’re trying to run before you can walk,” he informed me.

“What do you mean?”

“How many people are in the house?”

“Four of us.”

“So mathematically that’s six relationships. And it’s hard enough to make one relationship work.”

I had thought of it as a single relationship, or three at most. But I do the math—n(n-1)/2, with “n” being the number of lovers in a poly pod.—and he’s right.

“But there was this guy Father Yod,” I protest, “who had fourteen wives and it worked for him . . . I think.” I realize I don’t know much about how Father Yod managed his relationships. In fact, I just looked at the pictures.

“Who’s Father Yod?”

“He’s like Charles Manson, but without the killing.” Actually, that’s not totally true. I recall reading online afterward that Father Yod was a judo expert who murdered two people with his bare hands in self-defense.

“What I can tell you is that a shared living situation is what we call an advanced skill,” Pepper says, unfazed. “But trust me, it can work. I just went on a weeklong vacation to Hawaii with my partner and her boyfriend. And it was totally smooth because the three of us had spent so much time together.”

“Right now, I can’t see us ever getting to that point.” I suppose after a few years, one can get used to anything.

“Do you want me to come by and talk to them?”

“Please!”

When Pepper arrives an hour later, we gather in the living room, desperate for a miracle. I dare not sit on the couch in case it looks like I’m favoring whichever girl drops down next to me, so I take an armchair instead. Veronika and Pepper sit in the other chairs while Belle and Anne share the couch.

I introduce Pepper to everyone and list all the problems we’ve had so far. He listens carefully, then responds as if telling preschoolers to play nicely with each other. Unlike with monogamy, our culture offers no schooling on how to make a group relationship work, no real role models to look up to, and few—if any—friends to turn to for advice. Even in movies, when couples decide to open their marriage, the results are usually disastrous and the moral of the story is to stick with what you’ve got.

“Here’s your first lesson in going out together,” he begins. He is a sharp-featured, pale creature with long black hair, a black choker, and a slow, measured voice. I wonder if he was always this calm and deliberate or if it’s something he learned from years of managing multiple relationships. “You need to talk before you leave and have a plan for party protocol. If someone gets tired, do they take a cab home alone or do you all leave together? And if it’s a sexual situation, decide ahead of time whether you want to watch or leave or join the sex pile.” This makes perfect sense, yet it never occurred to me: The art of group relationships is logistics. “I want to encourage you to do little check-ins with one another constantly, with the knowledge that you don’t know each other very well. This way you can start to build a team feeling together.”

We nod in agreement. I suppose I was naïve to assume we would all just instantly become attached and live in relational utopia together. I’ve made mistakes in every monogamous relationship I’ve had, but I learned from them and that made the next relationship better. So it makes sense that my first multiple-partner relationship isn’t going to be a runaway success. It takes experience and failure to get good at anything. This is my opportunity to learn.

“I want to add something that’s important,” Pepper continues. “You”—he points to me—“are the fulcrum. This is a long-known poly situation. The fulcrum is the only person in a relationship with each partner, but because of that, you end up torn in a lot of different directions. It’s a very uncomfortable thing, because you’re empowered and disempowered at the same time.” He turns to the women. “So I would like to recommend that you all try to de-center Neil a little.”

I heave a hopefully imperceptible sigh of relief. I watched several documentaries on poly pods before coming here, and many were led by people with a pathological need to be the focal point of everyone’s love. They didn’t seem to care whose feelings got hurt as long as the empty space in their own hearts was kept filled. But for me, it’s no fun being the center of attention when it results in collateral damage to other people’s feelings.

“So how do we de-center me?” I ask Pepper.

“The three of you”—he gestures to my partners—“should hang out without him and also start negotiating decisions that don’t have to go through him first. The easy part of the situation is you and Neil, and you and Neil, and you and Neil”—here he points to each woman. “The hard part of the situation is your relationships with each other. I have a saying: Poly works or fails on trust between metamours.”

“What’s a metamour?” Veronika asks.

“A metamour is a partner’s partner. So if Neil and I were both dating you, then Neil would be my metamour. And it succeeds between him and me, because we have the hard part but not the good stuff. So when you build trust among metamours, everything comes together and the group starts functioning. Does that make sense?”

We were in the dark before. This pale Goth guy is the light. He’s a relationship pioneer, mapping new realms in interpersonal space.

He tells us about the burning period, which is the length of time (usually two years) it takes couples who open up to deal with the issues and challenges that occur as a result. I learn about the joys of theoretical nonmonogamy, which is when two people say they’re in an open relationship—but instead of actually sleeping with other people, they just get to feel free knowing they have the option to do so. There’s the jealousy test, which you pass if you’re able to have a serious relationship with someone who’s sleeping with other people or in love with someone else. Then there’s fluid bonded, which refers to partners who feel safe having unprotected sex with one another, and veto power, which means that one partner can ask another to end an outside relationship—an agreement that Pepper feels can cause more problems than it solves. Finally, there are the wearisome cowboys and cowgirls who get into the poly scene, date someone’s partner, and then try to rope that person into a monogamous relationship.

“So what do I do if I want to spend time with Neil alone?” Belle eventually asks. “Every time I try to do that, he says it’s rude to someone else.”

“Try not making the request to Neil. Make it to Anne and Veronika. And if they both say it’s okay, then you can do whatever you want with Neil.” The corners of Belle’s mouth turn up in an unsuccessfully repressed smile. Pepper spots this and adds sagely, “But be willing to hear a no.”

Veronika sighs and uncrosses her legs. “It’s so hard to share a person,” she says. “It would be easier if we didn’t have strong feelings. But there’s always going to be this mental fight to have him.”

Although having three attractive women fighting over me may seem like an ego trip, in reality it’s nerve shattering. Whatever interest they had in me before they arrived seems to have been exacerbated by the competition. According to a copy of O magazine I once read, polygamous men live nine years longer, on average, than monogamous men. But I wonder how Oprah could possibly be right. Because this is definitely not good for my blood pressure.

Pepper turns to me: “What you can do to get them past that point is reassure them. I’ve seen really jealous people and people with a lot of abandonment issues get past their shit once the fear of loss goes away. A good nonmonogamous group is like a flock of geese, which is to say it separates and comes back together.”

Anne opens her mouth to speak. The words escape soft and unsure. Everyone leans in to make sure they catch them. “For me, I was really surprised last night because when everybody was touching, it was hurting me.” She takes a pause so long it seems like an intermission. “I have a complicated family history, so maybe I get more possessive. But I understand now that we have to make things work so this can be a relationship.”

Pepper’s talk seems to be straightening everyone out. The metamours are remembering that they didn’t come here to be in some reality-show competition, but to live, learn, and grow in a mature relationship together. “I would recommend letting go of expectations and trying to get to a place of comfort with everything,” Pepper tells her. “If things get weird, let them be weird. If you can all get to a high communication level, and learn the process of negotiation and setting boundaries and talking through discomfort, this will start working much better for all of you.”

Before Pepper leaves, the girls and I agree to hold house meetings every day, during which each person gets a turn to speak uninterrupted–like in the talking-stick circle I made fun of back in sex rehab.

As a sense of calm and understanding descends on the house afterward, Veronika makes egg salad sandwiches and we sit around the table, all on the same page for the first time. Then, with Anne taking the front seat of the car without incident, we visit Alcatraz. As we walk from the ferry to the island prison, Belle holds my left arm while Anne clutches the other. Veronika wanders behind, taking photos.

“I feel like I’m a third child whose mother doesn’t have enough hands to hold,” Veronika says as she catches up to us.

She takes Anne’s hand in hers as a group of frat boys walks by and gives me a thumbs-up. For the first time, there’s a group energy connecting us. Perhaps all of us just needed to let go of our expectations like Pepper recommended, adjust to being somewhere new, and allow the relationship to set its own course.

And that’s when something unexpected happens: I’m overcome by a powerful sense of unworthiness. It doesn’t seem fair that these women have to share me. Any one of them could easily have her pick of the guys here who keep looking at us. But instead they’re settling for scraps of my affection.

When I imagined living in a freewheeling love commune during my monogamous relationship, I thought I’d be adrift in a blissful sea of pleasure, excitement, and feminine energy. But instead I only feel embarrassed that I’m monopolizing three hearts.

I spent my childhood starved for the love of the adult figures raising me, feeling like most of their positivity went to my brother and their negativity to me. So being in a position where I’m actually getting so much positive female caring is a new experience. Maybe the real purpose of this relationship for me is to break through my walls and feel worthy of love—or whatever this is.

CONCLUSION

This was the quiet before the storm: One of the worst relationship storms I’ve ever experienced.

The situation lasted roughly a week, then turned into a triad with just Belle and Veronika, then turned into me alone.

The lesson: If a relationship with one person is difficult, then a relationship with three people is going to be three times as difficult—or, according to the Pepper sum, six times as difficult.

Fortunately, or unfortunately, I am not a quitter. I decided that if I couldn’t make it work with three other people, then I’d definitely be able to make it work with ten.

After all, what could possibly go wrong?

But that’s a story for another time.

###

Want more stories and more of the lessons learned? Of course you do. Check out The Truth: An Uncomfortable Book About Relationships. I have my own dog-eared early copy.

The Nasty Icon of Retail, Sophia Amoruso

“I like to make promises that I’m not sure I can keep, and then figure out how to keep them.”  – Sophia Amoruso

Sophia Amoruso (@Sophia_Amoruso) is the Founder and Executive Chairman of Nasty Gal, a global online destination for both new and vintage clothing, shoes, and accessories.

Founded in 2006, Nasty Gal was named “Fastest Growing Retailer” in 2012 by Inc. Magazine, thanks to its 11,200% three-year growth rate.

Sophia has been called “fashion’s new phenom” by Forbes magazine, and she has become one of the most prominent and iconic figures in retail. She recently founded the #GIRLBOSS Foundation, which awards financial grants to women in the worlds of design, fashion, and music. Sophia’s first book, #GIRLBOSS, is a New York Times bestseller published in fifteen countries.

Listen to it on iTunes.
Stream by clicking here
Download as an MP3 by right-clicking here and choosing “save as”.

Want to hear another podcast from a founder of a rapidly growing business? — Listen to my conversations with Phil Libin of Evernote. In this episode, we discuss lessons learned from Jeff Bezos, Reid Hoffman, and others (stream below or right-click here to download):

This podcast is brought to you by Athletic Greens. I get asked all the time, “if you could only use one supplement, what would it be?” My answer is, inevitably, Athletic Greens. It is my all-in-one nutritional insurance. I recommended it in The 4-Hour Body and did not get paid to do so. Get 50% off your order at Athletic Greens.com/Tim.

This podcast is also brought to you by Vimeo Pro, which is ideal for entrepreneurs. In fact, a bunch of my start-ups are already using Vimeo Pro. WealthFront uses it to explain how it develops personalized investment portfolios. TaskRabbit uses it to tell the company’s story. Twitter uses it to showcase Periscope. Why are they using it instead of other options out there? Vimeo Pro provides enterprise level video hosting that typically costs thousands of dollars for a tiny fraction of the cost. Features include:

Gorgeous high-quality playback with no ads
Up to 20 GB of video storage every week
Unlimited plays and views
A fully customizable video player, which can include your company logo, custom outro, and more

You get all this for just $199 per year (that’s only $17 per/mo.) There are no complicated bandwidth calculations or hidden fees. Just go to Vimeo.com/business to check it out. If you like it, you can use the promo code “Tim” to get 25% off. This is the deepest discount you will find anywhere for Vimeo Pro.

QUESTION(S) OF THE DAY: What rapidly growing companies interest you the most and why?  Please let me know in the comments.

Scroll below for links and show notes…

Enjoy!

Selected Links from the Episode

eBay for Dummies by Marsha Collier
Influence by Robert Cialdini
Learn more about Girl Boss Guerilla
The Richest Man in Babylon by George Clason
Rilke on Love and Other Difficulties and Letters to a Young Poet by Rainer Maria Rilke
Learn more about Dating Naked
No Man’s Land by Doug Tatum
Venture Deals by Brad Feld and Jason Mendelson
Check out Valve Software’s Employee Handbook
Learn more about Index Fund
Visit the House of Air in San Francisco, CA
Watch The Color of Pomegranates, Sophia Amoruso’s favorite movie
Check out Jura Coffee makers and David Lynch Coffee
Connect with Sophia

Instagram | Twitter | Podcast | #GIRLBOSS

Show Notes

How do you answer the question, “What do you do?” [5:21]
The poopy pants story [9:06]
How Sophia Amoruso started her business [13:51]
Why Sophia is so good at selling on eBay [18:36]
On learning to write persuasive copy [21:26]
The inspiration for Sophia’s next book [23:21]
Most gifted books and favorite writers [24:31]
How to manage the stress of a quickly growing company [28:21]
The origins of Nasty Gal [30:41]
On the transition from eBay to NastyGal.com [33:56]
Advice for those seeking to grow a business similar to Nasty Gal [39:51]
Helpful books for those seeking to lead fast-growing companies [42:41]
The biggest challenges while growing Nasty Gal [45:01]
The mentors and/or resources that helped Sophia learn leadership [54:21]
Sophia’s biggest struggles [1:01:56]
Tips for interacting with the media [1:06:21]
What is Sophia Amoruso’s go-to drink at a bar? [1:15:56]
When you think of the word successful, who is the first person that comes to mind and why? [1:18:31]
Rapid fire questions: favorite movies, surprising world-class abilities, and common misconceptions [1:21:01]
If you could put a billboard anywhere and write anything on it, where would it be and what would it say? [1:24:26]
The process behind stepping down as CEO [1:26:51]
What purchase of $100 or less has most positively affected your life [1:29:36]
Daily rituals [1:31:26]
Advice for your thirty-year-old self [1:40:46]
What are you most looking forward to in the next 12 months [1:42:01]
Asks or requests of the audience [1:43:51]

People Mentioned

Rainer Maria Rilke
Betty Davis
Kelly Ripa
Natalie Massenet
Mickey Drexler
David Choe
Harley Pasternak

 

Should You Start a ‘Startup’ or Build a Cash-Flow Business?

“I should be used as a mercenary, not a lifer.”  – Tim Ferriss

In this episode, we have a change of pace…

Expa (@expa) is a startup studio. It was founded by Garrett Camp, who co-founded Uber. Every once in a blue moon, they put together a night of education. I was recently invited to participate in an event.

In this episode, I discuss the topic of startup design vs. lifestyle design. Some of you may be aware that I’ve been involved with various startups ranging from Uber to Facebook, Twitter and DuoLingo, and other businesses that have grown to more than 100 million users and customers.

Simultaneously, I have written about lifestyle design many times, and I’ve suggested that it should come before career planning. The question is, how do we reconcile these two different approaches to business?

Should you focus on building your muse and creating a cash-flow focused business to fuel your ideal lifestyle? Or should you swing for the fences and bet it all on a startup that is equity-driven? This podcast explores these topics — and many more — and aims to answer the questions that I think are under-examined.

Listen to it on iTunes.
Stream by clicking here
Download as an MP3 by right-clicking here and choosing “save as”.

Want to hear another podcast related to customer acquisition? — Listen to my podcast on how to build a large audience from scratch. In this episode, I answer some of your most-asked questions (stream below or right-click here to download):

This podcast is brought to you by 99Designs, the world’s largest marketplace of graphic designers. Did you know I used 99Designs to rapid prototype the cover for The 4-Hour Body? Here are some of the impressive results.  Click this link and get a free $99 upgrade.  Give it a test run…

This podcast is also brought to you by Wealthfront. Wealthfront is a massively disruptive (in a good way) set-it-and-forget-it investing service, led by technologists from places like Apple and world-famous investors. It has exploded in popularity in the last 2 years, and now has more than $2.5B under management. In fact, some of my good investor friends in Silicon Valley have millions of their own money in Wealthfront. Why? Because you can get services previously limited to the ultra-wealthy and only pay pennies on the dollar for them, and it’s all through smarter software instead of retail locations and bloated sales teams. Check out wealthfront.com/tim, take their risk assessment quiz, which only takes 2-5 minutes, and they’ll show you—for free–exactly the portfolio they’d put you in. If you want to just take their advice and do it yourself, you can. Or, as I would, you can set it and forget it.  Well worth a few minutes: wealthfront.com/tim.

Mandatory disclaimer: Wealthfront Inc. is an SEC registered Investment Advisor.

Investing in securities involves risks, and there is the possibility of losing money. Past performance is no guarantee of future results. Please visit Wealthfront dot com to read their full disclosure.

QUESTION(S) OF THE DAY: Are you building a cash-flow business or a startup? What problems and questions do you currently face? Please let me know in the comments.

Scroll below for links and show notes…

Enjoy!

Selected Links from the Episode

Learn more about Expa
Margin of Safety by Seth Klarman
Secrets of Power Negotiating by Roger Dawson
Getting Past No by William Ury
Anything You Want by Derek Sivers
Built to Sell by John Warrillow
The E-Myth Revisited by Michael E. Gerber
Buffett: The Making of an American Capitalist by Roger Lowenstein
Listen to interviews mentioned in this podcast:

Jocko Willink | Rick Rubin | Neil Strauss | Josh Waitzkin

Jon Favreau | Robert Rodriguez

Thinking, Fast and Slow by Daniel Kahneman
Small Giants by Bo Burlingham
Learn more about Derek Sivers

Questions From the Interview

How do you decide to invest in companies like Twitter and Uber? [8:06]
Are we in a bubble? [16:31]
Can you talk about your first business, BrainQUICKEN? [20:41]
Can you talk a little about bootstrapped businesses vs. venture-backed businesses? [26:16]
Are there examples of happy VC-backed founders? [29:16]
What approaches have you seen that are successful in venture businesses, and do you actually work 4 hours a week? [30:46]
Can you tell us about the distinction between a good CEO and a good founder? [36:16]
How do you factor happiness into work ethic? [38:06]
What are great examples of CEOs and founders who are killing it? [39:31]
How has your understanding of neuroscience affected your writing? [43:36]
Why prioritize wants vs. needs when starting a business? [47:46]
Who are your favorite podcast guests and why? [49:26]
Should a solo founder find a co-founder? [52:21]
What have you changed your mind about in the last year or two? [55:16]
Deconstructing “What next?“ in a lifestyle business, and the challenge of identifying “the one big problem.” [57:51]
If you had to choose between being an investor, writer, or podcaster, which would it be? [1:03:16]

People Mentioned

Mike Maples Jr.
Herb Kelleher
Steve Jobs
Warren Buffett
Marc Andreessen
Rick Rubin
Daniel Kahneman

The Tattooed Heretic of Wine and Whiskey, Richard Betts

“Wine is a grocery, not a luxury.”  – Richard Betts

Richard Betts (@yobetts) served as the wine director at The Little Nell in Aspen from 2000 to 2008. Much more interesting to me, Richard passed the Court of Master Sommeliers’ Masters Exam on his first attempt, becoming the ninth person in history ever to do so.

I first met Richard through investing wunderkind Chris Sacca, and we immediately hit it off. Richard can help you train your senses for anything, including wine, whiskey, his current love of mezcal, and far beyond.

He’s also done a lot of wild experiments, gotten a lot of tattoos, almost been shot in Mexico, and developed an incredible ability to simplify the complex. We get along.

In this conversation, we talk about nearly everything, ranging from the value of quitting to tricks of the trade, travel tips (he’s traveling 300+ days per year), and “starter” wines.

We also drink a boat-load of whiskey, me tasting and Richard teaching. The pictures below show a sample. Side note and cool rule of thumb: did you know it’s spelled “whiskey” when from countries that have “e” in their names (e.g. America) but “whisky” when from countries that don’t have an “e” in their names (e.g. Scotland, Japan)? Richard taught me that.

Last but not least, Richard is the author of a brand-new book, “The Essential Scratch & Sniff Guide to Becoming a Whiskey Know-It-All,” which is sitting on my kitchen table with whiskey stains all over it. It distils (see what I did there?) a couple of lifetimes worth of study down to 24 pages…then makes them smell good. Definitely check it out. At the very least, it gives you a bunch of rules of thumb (like the whiskey vs. whisky trick), so you can impress your friends and not look like a dumb-ass at the bar. Sweet! Less dumb-ass and more smart-ass is always good. Get ‘er done.

 

Listen to it on iTunes.
Stream by clicking here
Download as an MP3 by right-clicking here and choosing “save as”.

Want to hear another conversation that leaves no topic uncovered? — Listen to my conversation with Chris Sacca. In this episode, we discuss being different and making billions (stream below or right-click here to download):

This podcast is brought to you by MeUndies. If I’m not going commando, then I’m wearing MeUndies. I’ve been testing out pairs for about 3 or 4 months now, and, as a result, I’ve thrown out my other underwear. They look good, feel good, have options for men and women, and their materials are 2x softer than cotton, as evaluated using the Kawabata method. Not only does MeUndies offer underwear, but they also have incredible lounge pants. I wear them when I record the podcast, and when I’m out and about grabbing coffee.

If by some chance you’re not happy with the first pair you try on, they’ll refund your purchase completely. Check out MeUndies.com/Tim to see my current faves (some are awesomely ridiculous) and, while you’re at it, don’t miss lots of hot ladies wearing MeUndies.

This podcast is also brought to you by Athletic Greens. I get asked all the time, “If you could only use one supplement, what would it be?” My answer is, inevitably, Athletic Greens. It is my all-in-one nutritional insurance. I recommended it in The 4-Hour Body and did not get paid to do so. Get 50% off your order at Athletic Greens.com/Tim.

QUESTION(S) OF THE DAY: What is your favorite whiskey or wine? What is it about the brand(s) that make it a favorite? Please let me know in the comments.

Scroll below for links and show notes…

Enjoy!

Selected Links from the Episode

Learn more about Court of Masters Sommelier Testing
Check out The Little Nell, one of the best places in the world to drink wine
Visit world-class San Francisco restaurants, flour + water and Central Kitchen
Pick up some Kimbal Kimax Beakers (go with 250 ml)
Learn more about hurling, the fastest field sport in the world
In Praise of Shadows by Junichiro Tanizaki
Check out Sombra mezcal
Preferred tequila:

Siete Leguas | Tequila Ocho | Tequila Astral

The Crossroads of Should and Must by Elle Luna
A Fan’s Notes by Frederick Exley
The Art of Asking by Amanda Palmer
Learn more about Donors Choose
Favorite Movies:

The Breakfast Club | Baraka

Learn more about Dennis Scholl
Love Yourself Like Your Life Depends On It by Kamal Ravikant
The Essential Scratch & Sniff Guide to Whiskey by Richard Betts, Crystal English Sacca and Wendy MacNaughton
Connect with Richard Betts:

Twitter | Instagram | Facebook | Wine Specific

Wine Mentioned in this Episode:

Turley Wine Cellars
Ridge Vineyards
Rusden Wines
Mosse
Sucette 

Whiskey/Whisky Mentioned in this Episode:

Jack Daniels 
EH Taylor Rye
Jameson Irish Whiskey
Nikka Whisky (17-year-old)
Edradour Distillery (10-year-old)
Ardbeg Uigeadail
Bulleit Bourbon

Show Notes

Why Richard Betts got into wine? [7:22]
Characteristics of those who would excel as line cooks [20:15]
On the decision between culinary school and getting a job [21:40]
The story of falling in love with wine and becoming a sommelier [22:55]
Lessons learned as a sommelier [36:55]
The importance of the observation process [43:50]
Visual cues for seeing alcohol levels in wine [44:45]
How to correctly taste wine [36:50]
Understanding wine flavor characteristics [52:20]
Favorite zinfandels [45:50]
Common misconceptions about wine [58:15]
The sweet spot in terms of cost and value of wine [59:35]
What is the difference between bourbon and whiskey? [1:11:29]
Taste testing whisk(e)y [1:18:54]
The story of the convoy: explaining mezcal [1:52:14]
Rapid fire questions: Who is successful, when do you lose track of time, most gifted books, and fear of failure [2:00:24]
If Richard Betts was teaching a 9th-grade class, what would the subject be? [2:05:14]
Morning rituals for staying healthy while traveling [2:10:24]
A purchase of $100 or less that had the biggest impact [2:16:24]
Favorite movies and documentaries [2:18:09]
Advice for your 25- and 30-year-old self [2:23:54]
If you could put up a billboard anywhere and write anything on it, where would it be and what would it say? [2:30:39]
Describing The Essential Scratch & Sniff Guide to Whiskey [2:31:29]
An ask of the audience [2:35:39]

People Mentioned

Dennis DeConcini
Drew Curtis
Amanda Palmer

The 5 Things I Did To Become a Better Investor

I get asked a lot about investing.

This is mostly due to start-up investing and the hoopla around it, but I’ve expanded my experiments to late-stage deals, real estate, and more. So far, my startup bets are 10x+ more successful (on paper) than my publishing career. Based on cashed-out positions, they’re still several times more successful. I’ve had a lucky stretch.

By no means am I an elite investor, but I’ve borrowed from elite investors since 2007. I’m incredibly fortunate that amazing people have been very generous with their time. Thank you, all!

I’ve made hundreds of survivable mistakes, networked my little bald head off, and–net-net–I’m happy with the results.

In this short podcast episode, I’ll explain the five (or so) steps I took to become a better investor, starting at ground zero.

Caveat emptor: I am NOT a financial advisor, and none of this advice should be taken without speaking to a qualified professional first. Also, my results could be due to pure luck and zero skill. M’kay? M’kay.

The episode’s only 40 minutes long, despite it saying 2 hours. If the below player doesn’t work, just click here.

Hope you enjoy, and please let me know in the comments if you’d like more of this. Or what you’d like more of. Please correct me if I made mistakes in this episode!

Related reading that I mention in the audio:

Rethinking Investing

How I Created a Real-World MBA

Things I Learned and Loved in 2008 (Lots of Financial Lessons)

This podcast is brought to you by Wealthfront. Wealthfront is a massively disruptive (in a good way) set-it-and-forget-it investing service, led by world-famous investors technologists from places like Apple. It has exploded in popularity in the last two years, and they now have more than $2.5B under management. In fact, some of my good investor friends in Silicon Valley have millions of their own money in Wealthfront. Why? Because you can get services previously limited to the ultra-wealthy and only pay pennies on the dollar for them, and it’s all through smarter software instead of retail locations and bloated sales teams.

Check out wealthfront.com/tim, take their risk assessment quiz, which only takes 2-5 minutes, and they’ll show you—for free–exactly the portfolio they’d put you in. If you want to grab their advice and do it yourself, you can. Or, as I would, you can set it and forget it.  Well worth a few minutes: wealthfront.com/tim.

Mandatory disclaimer: Wealthfront Inc. is an SEC registered Investment Advisor.

Investing in securities involves risks, and there is the possibility of losing money. Past performance is no guarantee of future results. Please visit Wealthfront.com to read their full disclosure.

This podcast is also brought to you by 99Designs, the world’s largest marketplace of graphic designers. Did you know I used 99Designs to rapid prototype the cover for The 4-Hour Body? Here are some of the impressive results.  Click this link and get a free $99 upgrade.  Give it a test run…

Comedy’s Dynamic Duo, Seth Rogen and Evan Goldberg

No, we are not in jail. And am I really that short?!

“If we can write a high school movie, then we can make a high school movie.”

— Seth Rogen

This episode features a dynamic duo. Seth Rogen (@SethRogen) is an actor, writer, producer, and director. Evan Goldberg (@EvanDGoldberg) is a Canadian director, screenwriter, and producer. Together, they get into a lot of mischief and create amazing comedy.

They’ve collaborated on films such as Superbad (which they first conceived as teenagers), Knocked Up, Pineapple Express, The Green Hornet, and Funny People. They have also written for Da Ali G Show and The Simpsons.

In 2013, Evan and Seth released their directorial debut, This Is the End.  In 2014, Seth starred in and produced (alongside Evan) Neighbors, which was a worldwide comedy hit and has taken in more than $268 million.

In December 2014, Rogen and Goldberg’s film, The Interview, became the most-talked-about news story around the world. Under extremely difficult circumstances, the film persevered to become Sony Pictures’ #1 digital title of all time.

Neighbors 2 is shooting now and will be released next May. Seth and Evan are also in production on Sausage Party, a raunchy animated movie for adults about one sausage’s quest to discover the truth about his existence. Seth and Evan are producing the film with Megan Ellison and Conrad Vernon.

In our conversation, we discuss all manner of tactics and silliness, including:

Kyokushin karate
Writer’s block and related debates
Their writing process
Who are the most underrated comedians and comedy writers?
How Superbad got made… after they first drafted it around age 13
The odd book Judd Apatow recommended to them (also Woody Allen’s favorite)
How The Kids in the Hall influenced them
The movie they both wish they’d written
Common pot mistakes
Recommended newb pot for working versus relaxing
Will there be a McLovin spinoff?
And much more…

Listen to it on iTunes.
Stream by clicking here
Download as an MP3 by right-clicking here and choosing “save as”.

Want to hear another podcast related to comedy? — Listen to my conversation with Bryan Callen, who is a world-class comic and prolific actor. Stream this episode below or right-click here to download.

This podcast is brought to you by Vimeo Pro, which is the ideal video hosting platform for entrepreneurs. In fact, a bunch of my start-ups are already using Vimeo Pro. WealthFront uses it to explain how WealthFront works. TaskRabbit uses it to tell the company’s story. There are many other names who you would recognize among their customers (AirBnB, Etsy, etc.) Why do they use it? Vimeo Pro provides enterprise level video hosting for a fraction of the usual cost. Features include:

Gorgeous high-quality playback with no ads
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Unlimited plays and views
A fully customizable video player, which can include your company logo, custom outro, and more

You get all this for just $199 per year (that’s only $17 per/mo.). There are no complicated bandwidth calculations or hidden fees. Try it risk-free for 30 days. Just go to Vimeo.com/business to check it out. If you like it, you can use the promo code “Tim” to get 25% off. This is a special discount just for you guys.

This podcast is also brought to you by Athletic Greens. I get asked all the time, “If you could only use one supplement, what would it be?” My answer is, inevitably, Athletic Greens. It is my all-in-one nutritional insurance. I recommended it in The 4-Hour Body and did not get paid to do so. Get 50% off your order at Athletic Greens.com/Tim.

QUESTION(S) OF THE DAY: If you could interview any comedian, who would it be and why? Please let me know in the comments.

Scroll below for links and show notes…

Enjoy!

Selected Links from the Episode

The comic strip Calvin and Hobbes
The movie The Mist
The Freaks and Geeks television series
The Ski Patrol movie
Undeclared
Talladega Nights
The 40-Year-Old Virgin
Adaptation
The Princess Bride
The Larry Sanders Show
Rejected: A Film by Don Hertzfeldt
The Kids In The Hall
Fawlty Towers
Monty Python
Absolutely Fabulous
Watchmen by Alan Moore
Preacher – Book One by Garth Ennis
The Hitchhiker’s Guide to the Galaxy by Douglas Adams
Art Of Dramatic Writing by Lajos Egri
The Conquest of Happiness by Bertrand Russell
Love You Forever by Robert Munsch
The Fast and the Furious
“How Do People Get New Ideas?”
Jack Herer
Connect with Seth Rogen:

Twitter (@Sethrogen) | Facebook | Instagram (@sethrogen)

Connect with Evan Goldberg on Twitter (@evandgoldberg)

Show Notes

The story of how Seth Rogen and Evan Goldberg got into karate and beat the shit out of each other [06:42]
How their view of competitive violence changed after karate [10:58]
How Seth and Evan first met and when they first started collaborating [12:08]
How Seth and Evan decided to write Superbad [16:05]
The differences between standup comedy and movie writing [19:30]
How Seth and Evan’s writing process works [25:03]
How This Is The End came together, and how they created the film [27:01]
How the Superbad script came to life [33:24]
Being hired to write for Da Ali G Show and other acting roles [40:06]
The lessons Seth and Evan learned from Judd Apatow [44:06]
Thoughts on the concept of writer’s block [48:29]
Today’s most underrated comedy writers [52:04]
The first person who comes to mind when Seth and Evan think of the word successful [57:52]
The habit Evan picked up when working with Snoop Dogg [1:03:01]
The advice Evan and Seth would give their 25-year-old selves [1:05:07]
The reason nearly all involved in Freaks and Geeks ended up being so successful [1:11:06]
Weed and productivity [1:14:20]
The types of pot for different situations [1:17:30]

People Mentioned

Judd Apatow
Paul Feig
Jake Kasdan
Nicolas Cage
Hannibal Buress
Sacha Baron Cohen
Don Hertzfeldt
Trey Parker
Matt Stone
Woody Allen
Elon Musk
Bryan Callen
Steve Jobs
Isaac Asimov

The Scariest Navy SEAL Imaginable…And What He Taught Me

John “Jocko” Willink

“Discipline equals freedom.”

– Jocko Willink

Jocko Willink (@jockowillink) is one of the scariest human beings imaginable.

He is a lean 230 pounds. He is a Brazilian jiu-jitsu expert who used to tap out 20 Navy SEALs per workout. He is a legend in the Special Operations world. His eyes look through you more than at you.

He rarely does interviews, if ever. But, a few weeks ago, Jocko ended up staying at my house and we had a caffeinated mind meld. Here’s some background…

Jocko enlisted in the Navy after high school and spent 20 years in the SEAL Teams, first as an enlisted SEAL operator and then as a SEAL officer. During his second tour in Iraq, he led SEAL Task Unit Bruiser in the Battle of Ramadi — some of the toughest and most sustained combat by the SEAL Teams since Vietnam.

Under his leadership, Task Unit Bruiser became the most highly decorated Special Operations Unit of the entire war in Iraq and helped bring stability to Ramadi. Jocko was awarded the Bronze Star and a Silver Star.

Upon returning to the United States, Jocko served as the Officer-in-Charge of training for all West Coast SEAL Teams, designing and implementing some of the most challenging and realistic combat training in the world.

So why is Jocko opening up? Well, in part, we have mutual friends. Second, he is the co-author of an incredible new book — Extreme Ownership: How U.S. Navy SEALs Lead and Win — which I’ve been loving. Trust me. Buy it.

This is his first mainstream interview and one you won’t want to miss.

“Leadership is infinitely more about brains than it is about brawn. The brawn stuff is from the movies and it doesn’t work in reality.” – Jocko Willink

Listen to it on iTunes.
Stream by clicking here
Download as an MP3 by right-clicking here and choosing “save as”.

Want to hear another podcast related to leadership in the military from a decorated officer? — Listen to my conversations with General Stan McChrystal. In this episode, we discuss eating one meal per day, special ops, and mental toughness (stream below or right-click here to download):

This podcast is brought to you by Wealthfront. Wealthfront is a massively disruptive (in a good way) set-it-and-forget-it investing service, led by technologists from places like Apple and world-famous investors. It has exploded in popularity in the last 2 years, and now has more than $2.5B under management. In fact, some of my good investor friends in Silicon Valley have millions of their own money in Wealthfront. Why? Because you can get services previously limited to the ultra-wealthy and only pay pennies on the dollar for them, and it’s all through smarter software instead of retail locations and bloated sales teams

Check out wealthfront.com/tim, take their risk assessment quiz, which only takes 2-5 minutes, and they’ll show you—for free–exactly the portfolio they’d put you in. If you want to just take their advice and do it yourself, you can. Or, as I would, you can set it and forget it.  Well worth a few minutes: wealthfront.com/tim.

Mandatory disclaimer: Wealthfront Inc. is an SEC registered Investment Advisor.

Investing in securities involves risks, and there is the possibility of losing money. Past performance is no guarantee of future results. Please visit Wealthfront dot com to read their full disclosure.

This podcast is also brought to you by 99Designs, the world’s largest marketplace of graphic designers. Did you know I used 99Designs to rapid prototype the cover for The 4-Hour Body? Here are some of the impressive results.  Click this link and get a free $99 upgrade.  Give it a test run…

QUESTION(S) OF THE DAY: How has discipline supported your entrepreneurial goals? What aspects could still use improvement? Please let me know in the comments.

Scroll below for links and show notes…

Enjoy!

Selected Links from the Episode

Extreme Ownership: How U.S. Navy SEALs Lead and Win by Jocko Willink
Learn more about Victory MMA, Jocko Willink’s gym in San Diego
Seeking solutions in business or leadership? Check out Echelon Front
Connect with Jocko and his organizations on Twitter:

@Xtremeownership | @jockowillink | @echelonfront

Connect with Jocko and his organizations on Facebook:

Extreme Ownership | Jocko Willink | Echelon Front

About Face by Colonel David H. Hackworth
Blood Meridian by Cormac McCarthy
Learn more about Band of Brothers
Learn more about Letters from Iwo Jima
Hardcore History by Dan Carlin (Wrath of the Khans I)
Watch the Restrepo
A Chance in Hell: The Battle for Ramadi
The Pacific or “Band of Brothers in the Pacific”
With the Old Breed by E.B. Sledge
Watch Meru, the documentary about elite climbers
Listen to Black Flag, My War, Side B
Listen to White Buffalo

Show Notes

How Jocko would design training for someone who wants to add lean muscle mass [13:49]
The story of how Jocko Willink got involved in jiu-jitsu [15:44]
How Jocko Willink’s SEAL military experience influenced his business [19:24]
The story of how Jocko Willink became a SEAL [22:14]
Where mental toughness comes from [30:04]
Describing the Battle of Ramadi [31:04]
On the leadership and strategy required to take over a city [47:14]
The great tacticians that Jocko Willink respects, [52:44]
What makes a good leader and the things to look for when identifying good leaders [53:59]
How to teach the skill of detachment [1:01:34]
Jocko Willink’s workout that would cause entire platoons to “tap out” [1:09:14]
What are you world-class at that people might not know? [1:12:49]
Morning rituals [1:14:49]
When you think of the word successful, who are the first people that come to mind? [1:18:54]
Non-military leaders that Jocko Willink admires and considers role models [1:29:45]
Skills and/or experiences that every man should have [1:33:34]
Fear inoculation for civilians [1:40:14]
The books Jocko likes to give as gifts [1:42:20]
Common misconceptions about Navy SEALs [1:49:34]
If you could have one billboard anywhere, where would it be and what would it say? [1:55:59]
Explaining the purpose of his business, Extreme Ownership [2:00:14]
Discussing lessons from Extreme Ownership and the value it brings to private companies [2:06:19]
What SEALs discuss between themselves that they don’t discuss with civilians [2:12:44]
Which historical figure does Jocko Willink identify with? [2:18:29]
Something people would be surprised to learn about Jocko Willink [2:19:22]
Cheesy questions: What do you order at a bar, favorite music, advice for your 25- and 35-year-old self [2:22:49]

People Mentioned

Dean Lister
Cus D’Amato
H.R. McMaster
Sean MacFarland
Rickson Gracie
Marcelo Garcia
Marc Alan Lee
Michael A. Monsoor
Ryan Job

Scott Adams: The Man Behind Dilbert

“Be Useful.” – Scott Adams

Scott Adams (@scottadamssays) is a famous cartoonist and the creator of the Dilbert comic strip, which has been published in more than 2000 newspapers in 57 countries and in 19 languages.

In my conversation with Scott, we cover topics ranging from the rise of Dilbert, to how he uses affirmations to impact stock market decisions, success with women, and building his career. 

We also talk about Scott’s interest in hypnosis and its relationship with his writing process. Plus, we dive into his current fascination — Donald Trump. 

You’ll also find out more about:

Goals vs. systems, and how he has used them to get what he wants in life
His first ever Dilbert paycheck
The six dimensions of humor
How he got into the best shape of his life at age 58 and much, much more.

It is a really fun conversation. Scott is one hell of a character and a hilarious guy.

Enjoy!

Listen to it on iTunes.
Stream by clicking here
Download as an MP3 by right-clicking here and choosing “save as.”

Want to hear a podcast related to creativity? — Listen to my conversation with Ed Catmull, who is President and Co-Founder of Pixar and author of Creativity, Inc. Stream this episode below or right-click here to download:

This podcast is brought to you by Vimeo Pro, which is the ideal video hosting platform for entrepreneurs. In fact, a bunch of my start-ups are already using Vimeo Pro. WealthFront uses it to explain how WealthFront works. TaskRabbit uses it to tell the company’s story. There are many other names who you would recognize among their customers (AirBnB, Etsy, etc.) Why do they use it? Vimeo Pro provides enterprise level video hosting for a fraction of the usual cost. Features include:

Gorgeous high-quality playback with no ads
Up to 20 GB of video storage every week
Unlimited plays and views
A fully customizable video player, which can include your company logo, custom outro, and more

You get all this for just $199 per year (that’s only $17 per/mo.). There are no complicated bandwidth calculations or hidden fees. Try it risk-free for 30 days. Just go to Vimeo.com/business to check it out. If you like it, you can use the promo code “Tim” to get 25% off. This is a special discount just for you guys.

This episode is also sponsored by 99Designs, the world’s largest marketplace of graphic designers. Did you know I used 99Designs to rapid prototype the cover for The 4-Hour Body? Here are some of the impressive results. Click this link and get a free $99 upgrade. Give it a test run…

QUESTION(S) OF THE DAY: What is your biggest struggle with the creative process? Which experts would you like me to interview about their methods? Please let me know in the comments.

Scroll below for links and show notes…

Enjoy!

Selected Links from the Episode

More information about the reticular activation system
The Luck Factor by Richard Wiseman
The definition of selective memory
Judo foot sweeps 
Neuro-linguistic programming (NLP)
Scott’s blog on The iPhone 4 “High Ground Maneuver“
The tools Scott uses to draw his cartoons:

Wacom Cintiq monitor | Photoshop

Scott’s blog post on the 6 elements of humor
Other cartoons

F Minus | Pearls Before Swine

Background on the condition of spasmodic dysphonia.
Influence by Robert B. Cialdini
How To Stop Worrying And Start Living by Robert B. Cialdini
Scott’s book God’s Debris
Connect with Scott:

@ScottAdamsSays | http://dilbert.com | Calendar Tree

Show Notes

How Scott started using affirmations [08:45]
The beginning stages of Scott’s journey as a cartoonist [20:45]
The process Scott uses to create his affirmations and the reasons they work [22:39]
How God’s Debris came about [32:01]
How Scott incorporates hypnosis into his life [35:25]
Scott’s first hypnosis experience and why he started [39:15]
Scott’s definition of hypnosis [45:50]
How writing has helped his practice of hypnosis [48:41]
Hypnosis, NLP, and Donald Trump [51:00]
How the way Trump phrases his statements help him in the media [59:43]
Scott’s view on goals vs. systems, and why each approach can work [1:02:39]
Scott’s practical approach to dieting [1:12:29]
The first time Scott was paid for Dilbert, his ‘day job,’ and where his first ideas came from [1:18:27]
How he came up with the name Dogbert [1:21:51]
The aspects of Dilbert that have changed over time and what the characters mean to Scott [1:23:07]
Scott’s techniques to help Dilbert succeed and gain a competitive advantage over other cartoon strips [1:24:31]
The tools and routines Scott uses to get in the creative mood [1:30:42]
Scott’s morning routine [1:34:09]
Scott’s six elements of humor [1:37:26]
Other cartoons Scott respects and reads [1:41:26]
How Scott got his voice back after identifying he had spasmodic dysphonia [1:42:36]
The book Scott would recommend everyone should read [1:51:30]
When Scott thinks of the word “successful,” who is the first person that comes to mind? [1:58:58]
The advice Scott would give his 30-year-old self [2:01:54]

People Mentioned

Richard Wiseman
Milton Erickson
John Grinder
Tony Robbins
Steve Jobs
James Altucher
Donald Trump
Bill Gates

The Random Show: Okinawa, Pee on the Head, “Medicinal Spirits,” and Jedi Force Tiki Toss

This episode of The Random Show is full of accidental sexual references. There are dozens of topics covered in this wine-infused session of scatterbrained nonsense.

Like what? To start off: Okinawa, new diets, dog training, booze finds, accidental golden showers, tech, recommended books, people to follow on Twitter, and much more. O-tanoshimi dane!

For all previous episodes of The Random Show, including the infamous China Scam episode, click here.

Can’t see the video above? Click here.

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If anyone would like to add show notes with links in the comments, I’m happy to thank you with a link to your site. I’ll choose the best 1-2 people who are among the first to post.

QUESTION OF THE DAY:  What would you like to see in future episodes of The Random Show? Please let us know in the comments!