Timothy Ferriss's Blog, page 91

How to Travel the World for Free (And Win $4,000+ Worth of Prizes, Plus a Private Q&A)

If you have any interest in travel, then the next two minutes of reading are definitely worth your time.

It’s been too long since I’ve done a giveaway. I’ve been thinking about a trip to Australia or Montreal, so perhaps you’d like a getaway, too?  By that, I mean a vacation of epic proportions. I’ve partnered with StackSocial and Bootsnall to offer you a free ride around the globe.  Literally.  And there are tons of runner-up prizes (see below).

For those of you who really want to win, here’s a shortcut: Each time you share your unique link, which you get upon signing up, you receive another five entries. So spreading the word on Facebook and Twitter vastly improves your odds.

Click here to sign up. Share it well, and perhaps I’ll see you on the road!

Grand Prize: The Tim Ferriss Round-the-World Prize (worth $3,355.95)

Trip Around the World from BootsnAll (worth $3,000)

Sample route: San Francisco > Boston > Munich > Athens > Istanbul > Dubai > Bangkok > Saigon > Hong Kong > San Francisco
Customize your route to hit your must-see sites
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1-Hour Private Q&A Session with Tim Ferriss
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1st Runner Up: The High-Flying DJI Drone Prize  (worth $1,034.95)

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2nd Runner Up: The Tech-Savvy Tastemaker Prize  (worth $355.95)

Score the 7 gadgets you need this fall–all designed by top innovators, all best sellers. Power up outside with a solar battery pack, power yourself around the world with one plug, and carry it all in the stylish FYL Bag.

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Winner, Winner, Chicken Dinner…

To sign up, simply click here. And don’t forget, every time you share the page, your likelihood of winning increases.  Simple.

Hope to share a drink with you during your adventures.  One trip like this can change your life forever, so it’s worth taking 60 seconds to toss your hat in the ring.

Good luck and pura vida!

Dom D’Agostino on Fasting, Ketosis, and the End of Cancer

“The FDA may see ketones as a drug. I see them as a fourth macronutrient. You have fats, proteins, and carbs. Ketones are an energy-containing molecule.”  – Dom D’Agostino

Dr. Dominic “Dom” D’Agostino (@DominicDAgosti2) is an Assistant Professor in the Department of Molecular Pharmacology and Physiology at the University of South Florida Morsani College of Medicine, and a Senior Research Scientist at the Institute for Human and Machine Cognition (IHMC).

He has also deadlifted 500 pounds for 10 reps after a seven-day fast.

He’s a beast and — no big surprise — he’s a good buddy of Dr. Peter Attia, my MD friend who drinks “jet fuel” in search of optimal athletic performance.

The primary focus of Dom’s laboratory is developing and testing metabolic therapies, including ketogenic diets, ketone esters and ketone supplements to induce nutritional/therapeutic ketosis. D’Agostino’s laboratory uses in vivo and in vitro techniques to understand the physiological, cellular and molecular mechanism of metabolic therapies and nutritional strategies for peak performance and resilience. His research is supported by the Office of Naval Research (ONR), Department of Defense (DoD), private organizations and foundations.

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 discussing ketosis from a world class scientist? — Listen to my conversation with Dr. Peter Attia. In this episode, we discuss life-extension, drinking jet fuel, ultra-endurance, human foie gras, and more (stream below or right-click here to download):

This podcast is brought to you by Audible. I have used Audible for years and I love audio books. I have 2 to recommend:

The Graveyard Book by Neil Gaiman
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QUESTION(S) OF THE DAY: What questions do you have about ketogenic diets that we didn’t discuss in this podcast? Please let me know in the comments.

Scroll below for links and show notes…

Enjoy!

Selected Links from the Episode



Learn more about Institutional Review Boards
Learn more about the modified Atkins Diet and Erik Kosoff at John Hopkins
Learn more about HDAC inhibitors
Pick up your own Abbott Precision Xtra Glucose Monitor
Dom D’ Agostino’s favorite BCAA (branched chain amino acid) product Xtend
Cancer as a Metabolic Disease by Thomas Seyfried
Learn more about De Novo Nutrition and Utopian
See Dom’s website, KetoNutrition.org
Dom’s favorite companies for canned oysters and sardines: kingoscar.com and wildplanetfoods.com
Personal Power by Tony Robbins
The Language of God by Francis Collins
Screw Tape Letters by C.S. Lewis
One of the coolest things I’ve seen in a while (intro’d to me by Dom) — KetoPet Sanctuary
Learn more about The Origin (and Future) of the Ketogenic Diet
Tripping over the Truth by Travis Christofferson
Connect with Dom D’Agostino:

Facebook | Twitter | University of South Florida

Show Notes



How Dom D’Agostino responds when someone asks him, “what do you do?” [5:28]
Describing the Institutional Review Board (IRB) [9:53]
Research on advanced lifters in a state of ketosis [12:13]
Thoughts on getting big (hypertrophy) and strong while in a state of ketosis [15:53]
Defining ketones and ketosis [20:48]
The implications of fasting, nutritional ketosis and/or exogenous ketones for preventing/mitigating the onset of neurodegenerative diseases [28:23]
Defining cachexia, sarcopenia, anabolism, and catabolism [30:48]
Thoughts on the use of anabolic agents in cancer patients [34:48]
The advantage of SARMS instead of pre-existing low androgenic anabolic therapies [38:53]
To what extent is it possible to mimic the benefits of pre-chemo therapy fasting with exogenous ketones? [43:23]
How to accelerate the induction of ketone projection through use of exogenous ketones[49:18]
Ketone esters [56:13]
The benefits of eating exogenous ketones while in a carbohydrate attractive environment (for example, when traveling in Italy) [1:16:08]
What a traveling ketogenic breakfast looks like [1:20:43]
Reasons for using glutamine [1:25:08]
Thoughts on being considered a “nutritionist” [1:32:18]
The impact of Metformin on the survival rates of animals that have metastatic cancer [1:41:38]
If Dom D’Agostino learned that he had advanced cancer, what tools would he use to fight it? [1:46:18]
Thoughts on therapeutic fasting [2:03:03]
Observations of people who experiment with fasting [2:08:23]
Describing the risks and toxicities of consuming a cocktail of exogenous ketones [2:14:33]
Unusual foods or beverages that spike ketone levels [2:22:45]
Top resources for those seeking to learn about a ketogenic diet [2:41:33]
Most gifted books [2:43:13]
How to approach fighting Lyme Disease with the ketogenic diet [2:50:18]
The effect of ketosis on mitochondria [2:53:18]
Healing from use of antibiotics [2:55:53]



People Mentioned



George Cahill
Thomas Seyfried
Kevin Rose

 

How to Say “No” When It Matters Most (or “Why I’m Taking a Long ‘Startup Vacation'”)

(Photo: Michael Matti)

The wisdom of life consists in the elimination of non-essentials.

– Lin Yutang

Discipline equals freedom.

– Jocko Willink

This post will attempt to teach you how to say “no” when it matters most.

At the very least, it will share my story of getting there. It’s a doozy.

Here’s the short version:

I’m taking a long break from investing in new startups. No more advising, either. Please don’t send me any pitches or introductions, as I sadly won’t be able to respond. Until further notice, I am done. I might do the same with interviews, conferences, and much more.

Now, the longer version for those interested:

This post will attempt to explain how I think about investing, overcoming “fear of missing out” (FOMO), and otherwise reducing anxiety.

It’s also about how to kill the golden goose, when the goose is no longer serving you.

I’ll dig into one specifically hard decision — to say “no” to startup investing, which is easily the most lucrative activity in my life. Even if you don’t view yourself as an “investor”—which you are, whether you realize it or not—the process I used to get to no should be useful…

[Warning: If you’re bored by investment stuff, skip the next two bulleted lists.]

Caveat for any investing pros reading this:

I realize there are exceptions to every “rule” I use. Most of this post is as subjective as the fears I felt.
My rules might be simplistic, but they’ve provided a good ROI and the ability to sleep. Every time I’ve tried to get “sophisticated,” the universe has kicked me in the nuts.
Many startup investors use diametrically opposed approaches and do very well.
There are later-stage investments I’ve made (2-4x return deals) that run counter to some of what’s below (e.g. aiming for 10x+), but those typically involve a discount to book value, due to distressed sellers or some atypical event.
Many concepts are simplified to avoid confusing a lay audience.

Related announcements:

I will continue working closely with my current portfolio of startups. I love them and believe in them.
I will be returning all unallocated capital in my private Stealth Fund on AngelList. If you’re an investor in that fund, you’ll be getting your remaining money back. My public Syndicate will remain in place for later re-entry into the game.

So, why am I tapping out now and shifting gears?

Below are the key questions I asked to arrive at this cord-cutting conclusion.  I revisit these questions often, usually every month.

I hope they help you remove noise and internal conflict from your life.

The Road to No

ARE YOU DOING WHAT YOU’RE UNIQUELY CAPABLE OF, WHAT YOU FEEL PLACED HERE ON EARTH TO DO? CAN YOU BE REPLACED?

I remember a breakfast with Kamal Ravikant roughly one year ago.

Standing in a friend’s kitchen downing eggs, lox, and coffee, we spoke about our dreams, fears, obligations, and lives. Investing had become a big part of my net-worth and my identity. Listing out the options I saw for my next big moves, I asked him if I should raise a fund and become a full-time venture capitalist (VC), as I was already doing the work but trying to balance it with 5-10 other projects. He could sense my anxiety. It wasn’t a dream of mine; I simply felt I’d be stupid not to strike while the iron was hot.

He thought very carefully in silence and then said: “I’ve been at events where people come up to you crying because they’ve lost 100-plus pounds on the Slow-Carb Diet. You will never have that impact as a VC. If you don’t invest in a company, they’ll just find another VC. You’re totally replaceable.”

He paused again and ended with, “Please don’t stop writing.”

I’ve thought about that conversation every day since.

For some people, being a VC is their calling and they are the Michael Jordan-like MVPs of that world. They should cultivate that gift. But if I stop investing, no one will miss it. In 2015, that much is clear. There have never been more startup investors, and–right along with them–founders basing “fit” on highest valuation and previously unheard of terms. There are exceptions, of course, but it’s crowded. If I exit through the side door, the startup party will roll on uninterrupted.

Now, I’m certainly not the best writer in the world. I have no delusions otherwise. People like John McPhee and Michael Lewis make me want to cry into my pillow and brand “Poser” on my forehead.

BUT… if I stop writing, perhaps I’m squandering the biggest opportunity I have—created through much luck—to have a lasting impact on the greatest number of people. This feeling of urgency has been multiplied 100-fold in the last two months, as several close friends have died in accidents no one saw coming. Life is fucking short. Put another way: a long life is far from guaranteed. Nearly everyone dies before they’re ready.

I’m tired of being interchangeable, no matter how lucrative the game. Even if I’m wrong about the writing, I’d curse myself if I didn’t give it a shot.

Are you squandering your unique abilities? Or the chance to find them in the first place?

HOW OFTEN ARE YOU SAYING “HELL, YEAH!”? 

Philosopher-programmer Derek Sivers is one of my favorite people.

His incisive thinking has always impressed me, and his “hell, yeah!” or “no” essay has become one of my favorite rules of thumb. From his blog:

Those of you who often over-commit or feel too scattered may appreciate a new philosophy I’m trying: If I’m not saying “HELL YEAH!” about something, then I say no.

Meaning: When deciding whether to commit to something, if I feel anything less than, “Wow! That would be amazing! Absolutely! Hell yeah!” – then my answer is no. When you say no to most things, you leave room in your life to really throw yourself completely into that rare thing that makes you say “HELL YEAH!”

We’re all busy. We’ve all taken on too much. Saying yes to less is the way out.

To become “successful,” you have to say “yes” to a lot of experiments.  To learn what you’re best at, or what you’re most passionate about, you have to throw a lot against the wall.

Once your life shifts from pitching outbound to defending against inbound, however, you have to ruthlessly say “no” as your default. Instead of throwing spears, you’re holding the shield.

From 2007-2009 and again from 2012-2013, I said yes to way too many “cool” things. Would I like to go to a conference in South America? Write a time-consuming guest article for a well-known magazine? Invest in a start-up that five of my friends were in? “Sure, that sounds kinda cool,” I’d say, dropping it in the calendar. Later, I’d pay the price of massive distraction and overwhelm. My agenda became a list of everyone else’s agendas.

Saying yes to too much “cool” will bury you alive and render you a B-player, even if you have A-player skills. To develop your edge initially, you learn to set priorities; to maintain your edge, you need to defend against the priorities of others.

Once you reach a decent level of professional success, lack of opportunity won’t kill you. It’s drowning in 7-out-of-10 “cool” commitments that will sink the ship.

These days, I find myself saying “Hell, yes!” less and less with new startups. That’s my cue to exit stage left, especially when I can do work I love (e.g. writing) with 1/10th the energy expenditure.

I need to stop sowing the seeds of my own destruction.

HOW MUCH OF YOUR LIFE IS MAKING VERSUS MANAGING? HOW DO YOU FEEL ABOUT THE SPLIT?

One of my favorite time-management essays is “Maker’s Schedule, Manager’s Schedule” by Paul Graham of Y Combinator fame. Give it a read.

As Brad Feld and many others have observed, great creative work isn’t possible if you’re trying to piece together 30 minutes here and 45 minutes there. Large, uninterrupted block of time — 3-5 hours minimum — create the space needed to find and connect the dots. And one block per week isn’t enough.  There has to be enough slack in the system for multi-day CPU-intensive synthesis. For me, this means at least 3-4 mornings per week where I am in “maker” mode until at least 1pm.

If I’m in reactive mode, maker mode is all but impossible. Email and texts of “We’re overcommitted but might be able to squeeze you in for $25K. Closing tomorrow. Interested?” are creative kryptonite.

I miss writing, creating, and working on bigger projects. YES to that means NO to any games of whack-a-mole.

WHAT BLESSINGS IN EXCESS HAVE BECOME A CURSE? WHERE DO YOU HAVE TOO MUCH OF A GOOD THING?

In excess, most things take on the characteristics of their opposite. Thus:

Pacifists become militants.

Freedom fighters become tyrants.

Blessings become curses.

Help becomes hinderance.

More becomes less.

To explore this concept more, read up on Aristotle’s golden mean.

In my first 1-2 years of angel investing, 90%+ of my bets were in a tiny sub-set of startups. The criteria were simple:

Consumer-facing products or services
Products I could be a dedicated “power user” of, products that scratched a personal itch
Initial target demographic of 25-40-year old tech-savvy males in big US cities like SF, NYC, Chicago, LA, etc. (allowed me to accelerate growth/scaling with my audience)

Demonstrated traction and consistent growth (not doctored with paid acquisition).
No “party rounds”—crowded financing rounds with no clear lead investor. Party rounds often lead to poor due diligence and few people with enough skin in the game to really care.

Checking these boxes allowed me to add a lot of value quickly, even as relatively cheap labor (i.e. I took a tiny stake in the company). Shopify is a great example, which you can read about here (scroll down).

My ability to help spread via word of mouth, and I got what I wanted: great “deal flow.” Deals started flowing in en masse from other founders and investors.

Fast forward to 2015, and great deal flow is now paralyzing the rest of my life.  I’m drowning in inbound.

Instead of making great things possible in my life, it’s preventing great things from happening.

I’m excited to go back to basics, and this requires cauterizing blessings that have become burdens.

WHY ARE YOU INVESTING, ANYWAY?

For me, the goal of “investing” has always been simple: to allocate resources (e.g. money, time, energy) to improve quality of life. This is a personal definition, as yours likely will be.

Some words are so overused as to have become meaningless.  If you find yourself using nebulous terms like “success,” “happiness,” or “investing,” it pays to explicitly define them or stop using them. “What would it look like if I had (or won at) ___ ?” helps. Life favors the specific ask and punishes the vague wish.

So, here: to allocate resources (e.g. money, time, energy) to improve quality of life.

This applies to both the future and the present. I am willing to accept a mild and temporary 10% decrease in current quality of life (based on morale in journaling) for a high-probability 10x return, whether the ROI comes in the form of cash, time, energy, or otherwise. That could be a separate blog post, but conversely:

An investment that produces a massive financial ROI but makes me a complete nervous mess, or causes insomnia and temper tantrums for a long period of time, is NOT a good investment.

I don’t typically invest in public stocks for this reason, even when I know I’m leaving cash on the table. My stomach can’t take the ups and downs, but—like drivers rubbernecking to look at a wreck—I seem incapable of not looking. I will compulsively check Google News and Google Finance, despite knowing it’s self-sabotage. I become Benjamin Graham’s Mr. Market. As counter-examples, friends like Kevin Rose and Chris Sacca have different programming and are comfortable playing in that sandbox. They can be rational instead of reactive.

Suffice to say — For me, a large guaranteed decrease in present quality of life doesn’t justify a large speculative return.

One could argue that I should work on my reactivity instead of avoiding stocks. I’d agree on tempering reactivity, but I’d disagree on fixing weaknesses as a primary investment (or life) strategy.

All of my biggest wins have come from leveraging strengths instead of fixing weaknesses. Investing is hard enough without having to change your core behaviors. Don’t push a boulder up a hill just because you can.

Public market sharks will eat me alive in their world, but I’ll beat 99% of them in my little early-stage startup sandbox. I live in the middle of the informational switch box and know the operators.

From 2007 until recently, I paradoxically found start-up investing very low-stress. Ditto with some options trading. Though high-risk, I do well with binary decisions. In other words, I do a ton of homework and commit to an investment that I cannot reverse. That “what’s done is done” aspect allows me to sleep well at night, as there is no buy-sell choice for the foreseeable future. I’m protected from my lesser, flip-flopping self. That has produced more than a few 10-100x investments.

In the last two years, however, my quality of life has suffered.

As fair-weather investors and founders have flooded the “hot” tech scene, it’s become a deluge of noise. Where there were once a handful of micro VCs, for instance, there are now hundreds. Private equity firms and hedge funds are betting earlier and earlier. It’s become a crowded playing field. Here’s what that has meant for me personally:

I get 50-100 pitches per week. This creates an inbox problem, but it gets worse, as…
Many of these are unsolicited “cold intros,” where other investors will email me and CC 2-4 founders with “I’d love for you to meet A, B, and C” without asking if they can share my e-mail address
Those founders then “loop in” other people, and it cascades horribly from there. Before I know it 20-50 people I don’t know are emailing me questions and requests.
As a result, I’ve had to declare email bankruptcy twice in the last six months. It’s totally untenable.

Is there a tech bubble? That question is beyond my pay grade, and it’s also beside the point.

Even if I were guaranteed there would be no implosion for 3-5 years, I’d still exit now. Largely due to communication overload, I’ve lost my love for the game.  On top of that, the marginal minute now matters more to me than the marginal dollar.

But why not cut back 50%, or even 90%, and be more selective?  Good question. That’s next…

ARE YOU FOOLING YOURSELF WITH A PLAN FOR MODERATION?

The first principle is that you must not fool yourself and you are the easiest person to fool.

– Richard P. Feynman

Where in your life are you good at moderation? Where are you an all-or-nothing type? Where do you lack a shut-off switch? It pays to know thyself.

The Slow-Carb Diet succeeds where other diets fail for many reasons, but the biggest is this: It accepts default human behaviors versus trying to fix them. Rather than say “don’t cheat” or “you can no longer eat X,” we plan weekly “cheat days” (usually Saturdays) in advance. People on diets will cheat regardless, so we mitigate the damage by pre-scheduling it and limiting it to 24 hours.

Outside of cheat days, slow carbers keep “domino foods” out of their homes. What are domino foods? Foods that could be acceptable if humans had strict portion control, but that are disallowed because practically none of us do. Common domino foods include:

Chickpeas
Peanut butter
Salted cashews
Alcohol

Domino triggers aren’t limited to food. For some people, if they play 15 minutes of World of Warcraft, they’ll play 15 hours. It’s zero or 15 hours.

For me, startups are a domino food.

In theory, “I’ll only do one deal a month” or “I’ll only do two deals a quarter” sound great, but I’ve literally NEVER seen it work for myself or any of my VC or angel friends. Sure, there are ways to winnow down the pitches. Yes, you can ask “Is this one of the top 1-2 entrepreneurs you know?” to any VC who intro’s a deal and reject any “no”s. But what if you commit to two deals a quarter and see two great ones the first week? What then? If you invest in those two, will you be able to ignore every incoming pitch for the next 10 weeks?

Not likely.

For me, it’s all or nothing. I can’t be half pregnant with startup investing.  Whether choosing 2 or 20 startups per year, you have to filter them from the total incoming pool.

If I let even one startup through, another 50 seem to magically fill up my time (or at least my inbox). I don’t want to hire staff for vetting, so I’ve concluded I must ignore all new startup pitches and intros.

Know where you can moderate and where you can’t.

YOU SAY “HEALTH IS #1″…BUT IS IT REALLY?

After contracting Lyme disease and operating at ~10% capacity for nine months, I made health #1. Prior to Lyme, I’d worked out and eaten well, but when push came to shove, “health #1” was negotiable. Now, it’s literally #1. What does this mean?

If I sleep poorly and have an early morning meeting, I’ll cancel the meeting last-minute if needed and catch up on sleep. If I’ve missed a workout and have a con-call coming up in 30 minutes? Same. Late-night birthday party with a close friend? Not unless I can sleep in the next morning. In practice, strictly making health #1 has real social and business ramifications. That’s a price I’ve realized I MUST be fine paying, or I could lose weeks or months to sickness or fatigue.

Making health #1 50% of the time doesn’t work. It’s absolute — all or nothing. If it’s #1 50% of the time, you’ll compromise precisely when it’s most important.

The artificial urgency common to startups makes mental and physical health even more challenging. I’m tired of unwarranted last-minute “hurry up and sign” emergencies and related fire drills. It’s a culture of cortisol.

ARE YOU OVER-CORRELATED?

[NOTE: Two investors friends found this bullet slow, as they’re immersed in similar subjects. Feel free to skip if it drags on, but I think there are a few important novice concepts in here.]

“Correlated” means that investments tend to move up or down in value at the same time.

As legendary hedge fund manager Ray Dalio told Tony Robbins: “It’s almost certain that whatever you’re going to put your money in, there will come a day when you will lose 50 percent to 70 percent.” It pays to remember that if you lose 50%, you need a subsequent 100% return to get back to where you started. That math is tough.

So, how to de-risk your portfolio?

Many investors “rebalance” across asset classes to maintain certain ratios (e.g. X% in bonds, Y% in stocks, Z% in commodities, etc.). If one asset class jumps, they liquidate a part of it a buy more of lower performing classes. There are pros and cons to this, but it’s common practice.

From 2007-2009, during the “real-world MBA” that taught me to angel invest, barbell approach to investing. But most startups are illiquid. I commonly can’t sell shares until 7-12 years after I invest, at least for my big winners to date. What does that mean? In 2015, startups comprise more than 80% of my assets. Yikes!

Since I can’t sell, the simplest first step for lowering stress is to stop investing in illiquid assets.

I’ve sold large portions of liquid stocks—mostly early start-up investments in China–to help get me to “sleep at night” levels, even if they are lower than historical highs of the last 6-12 months. Beware of anchoring to former high prices (e.g. “I’ll sell when it gets back to X price per share…”). I only have 1-2 stock holdings remaining.

Some of you might suggest hedging with short positions, and I’d love to, but it’s not my forte. If you have ideas for doing so without huge exposure or getting into legal gray areas, please let me know in the comments.

In the meantime, the venture capital model is mostly a bull market business. Not much shorting opportunity. The best approximation I’ve seen is investing in businesses like Uber, which A) have a lot of international exposure (like US blue chips), and B) could be considered macro-economically counter-cyclical. For instance, it’s conceivable a stock market correction or crash could simultaneously lead fewer people to buy cars and/or more people to sign up as Uber drivers to supplement or replace their jobs. Ditto with Airbnb and others that have more variable than fixed costs compared to incumbents (e.g. Hilton).

WHAT’S THE RUSH? CAN YOU “RETIRE” AND COME BACK?

I’m in startups for the long game. In some capacity, I plan to be doing this 20+ years from now.

The reality: If you’re spending your own money, or otherwise not banking on management fees, you can wait for the perfect pitches, even if it takes years. It might not be the “best” approach, but it’s enough. To get rich beyond your wildest dreams in startup investing, it isn’t remotely necessary to bet on a Facebook or Airbnb every year. If you get a decent bet on ONE of those non-illusory, real-business unicorns every 10 years, or if you get 2-3 investments that turn $25K into $2.5M, you can retire and have a wonderful quality of life. Many would argue that you need to invest in 50-100 startups to find that one lottery ticket. Maybe. I think it’s possible to narrow the odds quite a bit more, and a lot of it is predicated on maintaining stringent criteria; ensuring you have an informational, analytical, or behavioral advantage; and TIMING.

Most of my best investments were made during the “Dot-com Depression” of 2008-2009 (e.g. Uber, Shopify, Twitter, etc.), when only the hardcore remained standing on a battlefield littered with startup bodies. In lean times, when startups no longer grace magazine covers, founders are those who cannot help but build a company. LinkedIn in 2002 is another example.

HOWEVER… This doesn’t mean there aren’t great deals out there.  There are. Great companies are still built during every “frothy” period.

The froth just makes my job and detective work 10x harder, and the margin of safety becomes much narrower.

[Tim: Skip this boxed text if the concept of “margin of safety” is old news to you.]

Think of the “margin of safety” as wiggle room.

Warren Buffett is one of the most successful investors of the 20th century and a self-described “value investor.” He aims to buy stocks at a discount (below intrinsic value) so that even with a worst-case scenario, he can do well. This discount is referred to as the “margin of safety,” and it’s the bedrock principle of some of the brightest minds in the investing world (e.g., Seth Klarman). It doesn’t guarantee a good investment, but it allows room for error.  Back in the startup world…

I want each of my investments, if successful, to have the ability to return my “entire fund,” which is how much capital I’ve earmarked for startups over two years, for instance. This usually means potential for a minimum 10X return. That 10X minimum is an important part of my recipe that allows margin for screw ups.

For the fund-justifying ROI to have a snowball’s chance in hell of happening, I must A) know basic algebra to ensure my investment amounts (check sizes) permit it, and B) avoid companies that seem overpriced, where the 10x price is something the world has never seen before (i.e. no even indirect comparables, or tenable extrapolations from even an expanded market size).

If you throw low-due-diligence Hail Mary’s everywhere and justify it with “they could be the next Uber!”, you will almost certainly be killed by 1,000 slow-bleeding $25K paper cuts. Despite current euphoria, applying something like Pascal’s Wager to startups is a great way to go broke.

Good startup investors who suggest being “promiscuous” are still methodical.

It’s popular in startup land to talk about “moonshots”—the impossibly ambitious startups that will either change the world or incinerate themselves into star dust.

I’m a fan of funding ballsy founders (which includes women), and I want many moonshots to be funded, but here’s the reality of my portfolio: as I’ve signed the investment docs for every big success I’ve had, I’ve always thought, “I will never lose money on this deal.”

The “this will be a home run or nothing” deals usually end up at nothing. I’m not saying such deals can’t work, but I try not to specialize in them.

These days, the real unicorns aren’t the media darlings with billion-dollar valuations. Those have become terrifyingly passé. The unicorns are the high-growth startups with a reasonable margin of safety.

Fortunately, I’m not in a rush, and I can wait for the tide to shift.

If you simply wait for blood in the streets, for when true believers are the only ones left, you can ensure come-hell-or-high-water founders are at least half of your meetings.

It might be morbid, but it’s practical.

My Last Deals For A While

It’s still a great time to invest in companies… but only if you’re able to A) filter the signal from the noise, B) say no to a lot of great companies whose investors are accepting insane terms, and C) follow your own rules. Doing all three of these requires a fuck-ton of effort, discipline, and systems. I prefer games with better odds.

There are a few deals you’ll see in the upcoming months, which I committed to long ago. These are not new deals.

They are current companies in which I’m filling my pro-rata, or companies postponing funding announcements until they’re most helpful (e.g. launching publicly). Separately, I work closely with the Expa startup lab and will continue to do so. They are largely able to insulate themselves from madness, while using and refining an excellent playbook.

Are You Having a Breakdown or a Breakthrough? A Short How-To Guide

“Make your peace with the fact that saying ‘no’ often requires trading popularity for respect.”

– Greg McKeown, Essentialism

If you’re suffering from a feeling of overwhelm, it might be useful to ask yourself two questions:

– In the midst of overwhelm, is life not showing me exactly what I should subtract?

– Am I having a breakdown or a breakthrough?

As Marcus Aurelius and Ryan Holiday would say, “The obstacle is the way.” This doesn’t mean seeing problems, accepting them, and leaving them to fester. Nor does it mean rationalizing problems into good things. To me, it means using pain to find clarity. Pain–if examined and not ignored–can show you what to excise from your life.

For me, step one is always the same: write down the 20% of activities and people causing 80% or more of your negative emotions.

My step two is doing a “fear-setting” exercise on paper, in which I ask and answer “What is really the worst that could happen if I did what I’m considering? And so what? How could I undo any damage?”

Below is a real-world example: the journal page that convinced me to write this post and kickstart an extended startup vacation.

The questions were “What is really the worst that could happen if I stopped angel investing for a minimum of 6-12 months? Do those worse-case scenarios really matter? How could I undo any potential damage? Could I do a two-week test?”

As you’ll notice, I made lists of the guaranteed upsides versus speculative downsides. If we define “risk” as I like to—the likelihood of an irreversible negative outcome—we can see how stupid (and unnecessarily painful) all my fretting and procrastination was. All I needed to do was put it on paper.

Below is a scan of the actual page.  Click here for an enlarged version.

Further below is a transcribed version (slightly shorter and edited). For a full explanation of how and why I use journaling, see this post.  In the meantime, this will get the point across:

Transcription:

“The anxiety is mostly related to email and startups: new pitches, new intros, etc.

Do a 2-week test where “no” to ALL cold intros and pitches?

Why am I hesitant? For saying “no” to all:

PROS:

– 100% guaranteed anxiety reduction

– Feeling of freedom

– Less indecision, less deliberation, so far more bandwidth for CREATING, for READING, for PHYSICAL [TRAINING], for EXPERIMENTS.

CONS (i.e. why not?):

– Might find the next Uber (

– Not get more deals. But who cares?

* Dinner with 5 friends fixes it.

* One blog post fixes it. [Here’s an example from 2013 that helped me find Shyp and co-lead their first round]

* NONE of my best deals (Shyp, Shopify, Uber, Twitter, Facebook, Evernote, Alibaba, etc.) came from cold intros from acquaintances.

If try 2 weeks, how to ensure successful:

– I don’t even see interview or [new] startup emails

– No con-calls. [Cite] “con call vacation” –> push to email or EOD [end-of-day review with assistant]

– Offer [additional] “office hours” on Fridays [for existing portfolio]?

I ultimately realized: If I set up policies to avoid new startups for two weeks, the systems will persist. I might as well make it semi-permanent and take a real “startup vacation.”

What do you need a vacation from?

My Challenge To You: Write Down The “What If”s

“I am an old man and I have known a great many troubles, but most of them never happened.”

– Mark Twain

“He who suffers before it is necessary suffers more than is necessary.”

– Seneca

Tonight or tomorrow morning, take a decision you’ve been putting off, and challenge the fuzzy “what if”s holding you hostage.

If not now, when? If left at the status quo, what will your life and stress look like in six months? In one year? In three years? Who around you will also suffer?

I hope you find the strength to say no when it matters most. I’m striving for the same, and only time will tell if I pull it off.

What will I spend my time on next? More crazy experiments and creative projects, of course.  To hear about them first, sign up for my infrequent newsletter. Things are going to get nuts.

But more important — how could you use a new lease on life?

To surf, like this attorney who quit the rat race? To travel with your family around the world for 1,000+ days, like this?  To learn languages or work remotely in 20+ countries while building a massive business? It’s all possible. The options are limitless…

So start by writing them down. Sometimes, it takes just a piece of paper and a few questions to create a breakthrough.

I look forward to hearing about your adventures.

How Renegade Filmmaker Casey Neistat Breaks Rules, Reinvents Himself, and Gets Thanked For It

“What is the ultimate quantification of success? For me, it’s not how much time you spend doing what you love. It’s how little time you spend doing what you hate.” – Casey Neistat

Casey Neistat (@caseyneistat) is a New York-based filmmaker. His online films have been viewed nearly 300,000,000 times in the last 5 years.

He is the writer, director, editor, and star of the series The Neistat Brothers on HBO and won the John Cassavetes Award at the 2011 Independent Spirit Awards for the film Daddy Long Legs. His main body of work consists of dozens of short films he has released exclusively on the Internet, including regular contributions to the New York Times critically acclaimed Op-Docs series. He is also the founder of Beme, a startup aiming to make creating and sharing video dead simple.

Casey is excellent at breaking every rule imaginable and having people (fans, sponsors, big brands, etc.) thank him for it. In this conversation, we dig into his history, techniques, influences, habits, and 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 with another award-winning movie maker? — Listen to my conversations with Robert Rodriguez. In this episode, we discuss the making of From Dusk ’till Dawn, Sin City, and what it means to be the “Wizard” of Hollywood (stream 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.

QUESTION(S) OF THE DAY: Casey is breaking the mold for what it means to be a filmmaker. Who are your favorite entertainers, artists, or entrepreneurs who are breaking the mold? Please let me know in the comments.

Scroll below for links and show notes…

Enjoy!

Selected Links from the Episode

Here are a few articles about Casey:

Get Away with Murder | Teen Welfare Dad |

Want to hack commercial flights? Check out Free Business Class Upgrades, everytime (Note: you must fly a whole lot)
Casey Neistat’s vlogging equipment

Cannon 70d | Sony RX-100

Learn more about Final Cut Pro X
The Second World War by John Keegan
The Autobiography of Malcolm X by Malcolm X, Alex Haley, and Attallah Shabazz
It’s Not How Good You Are, It’s How Good You Want to Be by Paul Arden
Some of Casey’s favorite bloggers:

Mr. Ben Brown | Fun For Louis

Neil Gaiman’s commencement speech, Make Good Art
Casey’s favorite movies:

Life And Death Of Colonel Blimp (IMDb) | Little Dieter Needs to Fly (IMDb)

Casey’s running playlist, Jonny Famous
Connect with Casey Neistat:

Subscribe to Casey on YouTube | Draw My Life | Beme | Twitter

Show Notes

On the challenges of working in New York City [2:20]
How Casey Neistat grew up [3:45]
The story of Bike Lanes [7:50]
How Casey Neistat responds when people ask, “what do you do?” [13:45]
The story behind Make It Count [15:05]
Casey’s pitch to Nike for the Make It Count video [18:05]
Suggestions for packing [23:15]
Thoughts on post production software [25:05]
Where novice YouTubers waste the most time [26:50]
Thoughts on how to be successful with YouTube [30:15]
On the decision to make a daily vlog [34:40]
The importance of devoting time to communicating with your audience [39:00]
The story behind Casey’s first paid gig in the entertainment business [40:30]
When you think of the word successful, who is the first person that comes to mind and why? [44:40]
Who makes Casey Neistat feel star-struck? [50:10]
Tips on developing the ability to be well-spoken [54:40]
Rapid fire questions: Most gifted books, best purchase of $100 or less, and favorite vloggers [1:01:05]
Common misconceptions [1:07:25]
On how to say, “no” [1:09:20]
What is a belief that you have that many people may think is crazy? [1:12:00]
The thinking behind Beme [1:15:00]
Top films that may not have been fully appreciated [1:20:50]
If you could put a billboard anywhere and write anything on it, where would it be and what would it say? [1:23:55]
An ask/suggestion for the audience [1:28:15]

People Mentioned

Tyler Oakley
Jason Harris
Po Bronson
Fred Hochberg
Tom Healy
Larry King
Jack Welch

How Casey Neistat Gets Away With Murder

“What is the ultimate quantification of success? For me, it’s not how much time you spend doing what you love. It’s how little time you spend doing what you hate.” – Casey Neistat

Casey Neistat (@caseyneistat) is a New York-based filmmaker. His online films have been viewed more than 50,000,000 times in the last 3 years.

He is the writer, director, editor, and star of the series The Neistat Brothers on HBO and won the John Cassavetes Award at the 2011 Independent Spirit Awards for the film Daddy Long Legs. His main body of work consists of dozens of short films he has released exclusively on the Internet, including regular contributions to the New York Times critically acclaimed Op-Doc series. He is also the founder of Beme, a startup aiming to make creating and sharing video dead simple.

Casey is excellent at breaking every rule imaginable and having people (fans, sponsors, big brands, etc.) thank him for it. In this conversation, we dig into his history, techniques, influences, habits, and 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 with another award-winning movie maker? — Listen to my conversations with Robert Rodriguez. In this episode, we discuss the making of From Dusk ’till Dawn, Sin City, and what it means to be the “Wizard” of Hollywood (stream below or right-click here to download):

 

This podcast is 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: Casey is breaking the mold for what it means to be a filmmaker. What other entertainers, artists, or entrepreneurs do you appreciate who also are breaking the mold? Please let me know in the comments.

Scroll below for links and show notes…

Enjoy!

Selected Links from the Episode

Here are a few articles about Casey:

Get Away with Murder | Teen Welfare Dad |

Want to hack commercial flights? Check out Free Business Class Upgrades, everytime (Note: you must fly a whole lot)
Casey Neistat’s vlogging equipment

Cannon 70d | Sony RX-100

Learn more about Final Cut Pro X
The Second World War by John Keegan
The Autobiography of Malcolm X by Malcolm X, Alex Haley, and Attallah Shabazz
It’s Not How Good You Are, It’s How Good You Want to Be by Paul Arden
Some of Casey’s favorite bloggers:

Mr. Ben Brown | Fun For Louis

Neil Gaiman’s commencement speech, Make Good Art
Casey’s favorite movies:

Life And Death Of Colonel Blimp (IMDb) | Little Dieter Needs to Fly (IMDb)

Casey’s running playlist, Jonny Famous
Connect with Casey Neistat:

Subscribe to Casey on YouTube | Draw My Life | Beme | Twitter

Show Notes

On the challenges of working in New York City [2:20]
How Casey Neistat grew up [3:45]
The story of Bike Lanes [7:50]
How Casey Neistat responds when people ask, “what do you do?” [13:45]
The story behind Make It Count [15:05]
Casey’s pitch to Nike for the Make It Count video [18:05]
Suggestions for packing [23:15]
Thoughts on post production software [25:05]
Where novice YouTubers waste the most time [26:50]
Thoughts on how to be successful with YouTube [30:15]
On the decision to make a daily vlog [34:40]
The importance of devoting time to communicating with your audience [39:00]
The story behind Casey’s first paid gig in the entertainment business [40:30]
When you think of the word successful, who is the first person that comes to mind and why? [44:40]
Who makes Casey Neistat feel star-struck? [50:10]
Tips on developing the ability to be well-spoken [54:40]
Rapid fire questions: Most gifted books, best purchase of $100 or less, and favorite vloggers [1:01:05]
Common misconceptions [1:07:25]
On how to say, “no” [1:09:20]
What is a belief that you have that many people may think is crazy? [1:12:00]
The thinking behind Beme [1:15:00]
Top films that may not have been fully appreciated [1:20:50]
If you could put a billboard anywhere and write anything on it, where would it be and what would it say? [1:23:55]
An ask/suggestion for the audience [1:28:15]

People Mentioned

Tyler Oakley
Jason Harris
Po Bronson
Fred Hochberg
Tom Healy
Larry King
Jack Welch

Thinking About Extra Dimensions with Physicist Lisa Randall

Physics professor, Lisa Randall, is co-author of a paper that suggests dark matter may have played a role in the extinction of the dinosaurs.
(Credit: Rose Lincoln/Harvard Staff Photographer)

“Be curious and try to find solutions to problems.”  – Lisa Randall

Professor Lisa Randall (@lirarandall) researches particle physics and cosmology at Harvard, where she is a professor of theoretical physics.

Professor Randall was the first tenured woman in the Princeton physics department, and the first tenured female theoretical physicist at Harvard. In autumn 2004, she was the most cited theoretical physicist of the previous five years.

In 2007, Randall was named one of Time magazine’s 100 Most Influential People (Time 100) under the section for “Scientists & Thinkers.” Randall was given this honor for her work regarding the evidence of a higher dimension.

She has written several mind-expanding books, the newest of which is Dark Matter and the Dinosaurs: The Astounding Interconnectedness of the Universe.  If you want a semi-psychedelic experience (viewing the world through a new lens) without imbibing substances, this is worth checking out.

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 spirituality and science from a world class thinker? — Listen to my conversations with Sam Harris. In this episode, we discuss spirituality, neuroscience, meditation, and more (stream below or right-click here to download):

This podcast is brought to you by Thrive Market. If you’re anything like me, you care a lot about the food you put in your body. In fact, I think it’s much more important than exercise. The problem is that good food can be extremely expensive…but it doesn’t have to be.

Thrive Market is like Costco for everything healthy – an online shopping club offering the best brands and groceries at 25-50% off retail prices, shipped nationally for free. There are a lot of Slow Carb Diet friendly items that I recommend in The 4-Hour Body. You can easily filter everything by your preferences: paleo, gluten-free, vegan, raw, non-GMO, etc.

Never pay full price for healthy food again. Go to thrivemarket.com/tim to start your free 2-month trial and 25% off your first order. What do you have to lose? Nothing. So check it out: thrivemarket.com/tim.

QUESTION(S) OF THE DAY: What are your thoughts on the value of applied science and basic science? Is one more valuable than the other? If so, why? Please let me know in the comments.

Scroll below for links and show notes…

Enjoy!

Selected Links from the Episode

Inside Job — a documentary on Wall Street shenanigans and financial meltdowns
Learn more about the Hampshire College Summer Studies in Mathematics (Math Camp)
Warped Passages: Unraveling the Mysteries of the Universe’s Hidden Dimensions by Lisa Randall
The Time Machine by H. G. Wells
Knocking on Heaven’s Door: How Physics and Scientific Thinking Illuminate the Universe and the Modern World by Lisa Randall
Dark Matter and the Dinosaurs: The Astounding Interconnectedness of the Universe by Lisa Randall
Hidden Cosmos by Timothy Ferris in National Geographic
The Pleasure of Finding Things Out by Richard Feynman
Learn more about Interstellar
Higgs Discovery: The Power of Empty Space by Lisa Randall
Learn more about Jimmy Chin and Meru
I Capture the Castle by Dodie Smith
Connect with Lisa Randall on Twitter

Show Notes

How do you answer the question, “what do you do?” [6:33]
Defining physics [8:08]
Defining theoretical physics [8:58]
Defining cosmology [9:53]
On succeeding in the male-dominated world of science, and the value of “math camp” [12:33]
Explaining the title for Warped Passages [25:33]
Defining hidden dimensions [28:18]
The search for fundamental connections in the universe [34:13]
Defining dark matter and dark energy [40:28]
Why are outer planets in our solar system bigger than those closer to the sun? [44:28]
Common misuses of physics terms [45:53]
Is time an illusion? [51:43]
Are there aspects of philosophy that are becoming more relevant to physics? [54:28]
How science could expand empathy [57:08]
Thoughts on Interstellar [1:01:03]
Thoughts on consciousness after physical death [1:02:53]
Could you describe a tennis ball as it moves through additional dimensions of space? [1:05:13]
What is the significance of the Higgs boson? [1:06:43]
Why does cosmology research matter? [1:11:33]
What is the difference between basic science and applied science? [1:13:28]
When you think of the word successful, who is the first person who comes to mind and why? [1:15:13]
In the last five years, when have you felt the most successful? [1:16:13]
Most gifted books [1:18:03]
What purchase of $100 or less has most positively affected your life recently [1:20:08]
What do you believe that other people might consider to be insane? [1:21:03]
Should the scientific community be focusing on large-scale expensive science projects or create many smaller scale science projects? [1:22:58]
Thoughts on the superstring theory.  [1:25:53]
If you could put a billboard anywhere and write anything on it, where would it be and what would it say? [1:27:38]
Advice for your 30-year-old self [1:28:58]
An ask or request for the audience [1:29:53]

People Mentioned

Richard Feynman
Dana Randall
Albert Einstein
Timothy Ferris

The Athlete (And Artist) Who Cheats Death, Jimmy Chin

“I’m the laziest motivated person that I know!” — Jimmy Chin

Jimmy Chin (@jimkchin) is an artist and professional athlete, often at the same time. If Chase Jarvis and Laird Hamilton had a love child, it would be Jimmy.

He has participated in and documented breakthrough expeditions around the planet, from climbing first ascents in the Karakoram to skiing first descents in the Himalayas. He is one of the few people to both climb Mount Everest and ski it from the summit.  Most recently, he filmed and directed the incredible feature documentary MERU, which is in theaters now and won the 2015 Audience Award at Sundance.

What is MERU? In the high-stakes game of big-wall climbing, the Shark’s Fin on Mount Meru is the ultimate prize. Everest is a cakewalk by comparison. Sitting at the headwaters of the sacred Ganges River in Northern India, the Shark’s Fin has seen more failed attempts by elite climbing teams over the past 30 years than any other ascent in the Himalayas. This movie is the story of one group’s journey to conquer it—a white-knuckle quest of friendship, sacrifice, hope and obsession. How Jimmy captured it on film while risking his life is almost impossible to fathom.

In this episode of the podcast, we talk about his origins, training, nutrition, gear, and MERU, of course.

Suffice to say, if you want a benevolent kick in the ass, the film MERU is your assignment. I saw it a few weeks ago, and all my family could say for minutes afterward was, “Whoa….” My refrain was, “Holy shit…,” which I muttered to myself at least 20 times in 90 minutes.  It’s an amazing, terrifying, and inspiring edge-of-your-seat experience.

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 with super athletes? — Listen to my conversation with Laird Hamilton, Gabrielle Reece, and Brian MacKenzie. In this incredible episode, we explore underwater training, strengthening your weaknesses, and advice for beat up athletes. Check it out.

This podcast is brought to you by TrunkClub. I hate shopping with a passion. And honestly I’m not good at it, which means I end up looking like I’m colorblind or homeless. Enter TrunkClub, which provides you with your own personal stylist and makes it easier than ever to shop for clothes that look great on your body. Just go to trunkclub.com/tim and answer a few questions, and then you’ll be sent a trunk full of awesome clothes. They base this on your sizes, preferences, etc. The trunk is then delivered free of charge both ways, so you only pay for clothes that you keep. If you keep none, it costs you nothing. To get started, check it out at trunkclub.com/tim.

This podcast is also brought to you by Mizzen + Main. These are the only “dress” shirts I now travel with — fancy enough for important dinners but made from athletic, sweat-wicking material. No more ironing, no more steaming, no more hassle. Click here for the exact shirts I wear most often. Don’t forget to use the code “TIM” at checkout.

QUESTION(S) OF THE DAY: What other athletes or world-class performers would you love to hear on the podcast?  Please let me know in the comments.

Scroll below for links and show notes…

Enjoy!

Selected Links from the Episode

Trango Towers
Grand Teton National Park
Yosemite National Park
Meru Peak
Exum Mountain Guides and Jackson Hole Mountain Guides
Jimmy’s favorite gear: Five Ten Anasazi Climbing Shoes, DynaFit Boots, Armada Skis, and Black Diamond Skis
Jimmy stays energized with Clif Shot Bloks, Hammer Nutrition Heed sports drinks, and Endurolytes
On expeditions, Jimmy listens to The Glitch Mob and José González
NOLS (National Outdoor Leadership School)
Patagonia Land Trust
Valley Uprising
Coming into the Country by John McPhee
Missoula: Rape and the Justice System in a College Town by Jon Krakauer
Let My People Go Surfing: The Education of a Reluctant Businessman by Yvon Chouinard
Musashi: An Epic Novel of the Samurai Era by Eiji Yoshikawa and Charles Terry
A Guide to the I Ching by Carol K. Anthony
Casamigos and Casa Dragones
Jack Black 25 SPF Lip Balm
Connect with Jimmy Chin

MERU | Instagram | Twitter | Facebook | Jimmy Chin

Show Notes

How do you pronounce “MERU?” [08:22]
How do you answer the question, “What do you do?” [09:18]
What is a first ascent and a first descent? [11:55]
Defining car-to-car time [17:25]
Why an outdoor athlete may start spending more time at the gym [19:55]
A typical week of training [21:06]
Most common beginning rock climbing mistakes (and corrections) [27:42]
Overcoming the fear of rock climbing [30:30]
Jimmy’s gear (shoes, boots, skis) [32:00]
Jimmy’s nutrition routine [33:11]
What does Jimmy listen to when he’s on expeditions? [34:50]
Goals for aspiring climbers [37:07]
Finding a good mountain guide [39:42]
Defining moments from Jimmy’s childhood [42:44]
Jimmy’s parenting style [44:44]
How Jimmy got started with photography [51:14]
Lessons Jimmy learned from Galen Rowell’s work ethic [58:38]
Dealing with fear and House of Cards [01:01:36]
How Jimmy improved his writing skills [01:09:31]
The first person who comes to mind when Jimmy thinks of success [01:11:52]
The books Jimmy gives as gifts [01:13:25]
Jimmy’s morning rituals [01:15:00]
Drinks of choice  [01:17:54]
A purchase of $100 or less that had the most positive impact [01:19:03]
What would Jimmy put on a billboard, and where would it be? [01:20:07]
What advice would Jimmy give his 30-year-old self? [01:21:05]

People Mentioned

Chase Jarvis
Laird Hamilton
Doug Coombs
Justin Boreta
Jose Gonzalez
Alex Honnold
Conrad Anker
Galen Rowell
Dean Potter
Steph Davis
Timmy O’Neill
Cedar Wright
Peter Croft
Ernest Hemingway
John McPhee
Jonathan Franzen
Jon Krakauer
Yvon Chouinard
Carol K. Anthony

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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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. I have used them for years to create some amazing designs. When your business needs a logo, website design, business card, or anything you can imagine, check out 99Designs.

I used them to rapid prototype the cover for The 4-Hour Body, and I’ve also had them help with display advertising and illustrations. If you want a more personalized approach, I recommend their 1-on-1 service, which is non-spec. You get original designs from designers around the world. The best part? You provide your feedback, and then you end up with a product that you’re happy with or your money back. Click this link and get a free $99 upgrade.  Give it a test run…

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:

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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