Month: February 2019

Wasted Time

One of the fun things about rebuilding your life from scratch in your 30s is realizing how much easier self-improvement would have been if you’d started in your 20s.

An example: I’m officially at the halfway point of my eight week Orange Theory Fitness (OTF) “transformation challenge” and I gotta say, I’m feeling pretty pleased with how it’s going.

This past Wednesday’s workout included a 12 minute “run for distance” – i.e. a test to see how far you can run, without dying, in 12 minutes.

Now. Please remember that, as of December of last year (that is, less than three months ago), I had never in my life set foot on a treadmill. Moreover, I literally didn’t understand the mechanics of running for more than a few seconds at a time. I spent much of the treadmill time in that first OTF class trying not falling flat on my face.

Fast forward to this week and imagine my sense of achievement when I crossed the one mile mark of my run and the timer showed just a hair under eight minutes. An eight minute mile isn’t going to win me any road races – my cursory Googling suggests that eight minutes is an OK average per-mile time for a reasonably fit casual runner – but for me it represents gigantic progress. From zero to an eight minute mile in less than three months.

And yet, as I raced past that first mile, then looked up and down the treadmill line to see how my fellow runners were doing, I couldn’t help think what OTF must be like for, say, a 25 year old. Specifically, I couldn’t help comparing the energetic twenty-somethings pounding out their twelve minute runs with myself at their age.

Christ, when I was 25 I could barely cross the street without taking a rest. How much fitter and stronger might I have been today if, instead of drinking my 20s away, I’d have spent that time and energy in the gym?

A similar thought occurred to me last year when I went to visit my brother and his wife in Montreal.  Like most British people, I studied French for years at school. I scraped an A grade at GSCE level (age 16) and, in my mind at least, still retained enough vocabulary and grammar to comfortably navigate a French-speaking city. Bonjour! I would say, to the Francophones. Bonjour!, they would reply, veux-tu de la poutine?

And I would understand what they were asking!


Not in the slightest.

It turns out that language is a muscle like any other. If you don’t use it for 22 years, it atrophies down to nothing.

So on my return to San Francisco, I signed up for weekly French lessons. I’ve been taking the classes for about 12 months and am now finally at the point where I can talk in French, reasonably competently, for an hour about any topic that’s on my mind. As with the running, this represents huge progress. I’m both pleased with myself, and grateful for my tutor, Elisabeth. (Not for Elisabeth mundane topics like ordering bread, or asking for directions to the nearest swimming pool. In recent weeks we’ve discussed, en français, topics as varied as Brexit, the Yellow Vest protests, Netflix, and San Francisco income inequality.)

And yet. And yet.

As with OTF, I can’t shake the nagging frustration at how much more fluent I might be at this had I stuck with learning French after leaving school.  Or spent a few pounds on French lessons in my 20s rather than wasting those same pounds (and 20s) drinking,

The answer is much more fluent. Just as, duh, I’d be much fitter had I been running since my teens, or much smarter if I’d read as much in my 20s as I do today.

It’s hard not to see my 20s as a decade of wasted opportunity. The what-ifs never stop coming, and are only made worse when – as happened at OTF this week – I feel like I’m actually making progress with something.

And of course it’s a ridiculous, and unhelpful, way to look at sobriety. For one thing, it’s a waste of time. Wasting time worrying about wasted time must surely be the definition of compounding a problem.

For another thing, I still managed to pack a ton into my “wasted” 20s, including writing a weekly column for the Guardian, authoring a dozen books (one of which almost became a movie), and moving to the US. That’s pretty impressive for a guy who could barely bend down to tie his shoelaces without tumbling into a gutter.

Mostly though, it’s not a helpful thought process because it’s not true. The reason I’m so engaged in OTF or French classes today is precisely because I wasted all that time. I wrote about this back at TechCrunch : How the problem Silicon Valley’s obsession with living forever is that death is such a great motivator.

It’s only because I wasted so much time that I’m so driven to pack as much as possible into my 30s and 40s. The idea that a sober version of me would have spent that time learning French or running on a treadmill rather than, say, watching reality TV or eating McDonalds is just silly. There are plenty of out of shape sober people, and countless non-drinkers who lack the motivation to write a tweet, let alone a book. No reason to think I wouldn’t be one of them.

So instead of feeling frustrated at the time I wasted, I’m going to focus on feeling glad for the time I didn’t waste. Glad that ten years ago, at age 29, I decided to get sober, rather than waiting til I was 39 or 49.

If you’re 49 and just got sober, then you can be glad you didn’t wait til 59 or 69. Hell, I don’t care if you’re 99 years old when you quit: Every minute of sobriety you’re able to salvage and exploit is a fucking gift, and one that non-addicts can never truly understand.


Hi everyone.


I have a cold.


It’s pretty annoying.

Sniff. Sniff.

But it could be worse.

I used to feel sick every day. Lethargic, achy, usually with a headache. Sometimes I’d have heart palpitations. Or maybe my teeth would hurt, or I’d feel nauseous.

Those were the good days.

On the bad days, I literally couldn’t get out of bed before noon. Or 4pm. I missed meetings, and appointments, and friends’ birthdays, and flights. Those were the days when the symptoms until late at night, or even into the next day. Times when none of the purported hangover cures worked – not even hair of the dog. Drinking on a hangover just made me feel even worse, and made the next day’s hangover-hangover twice as bad.

I’m not sure if it’s because I drank more than most people, or if there’s some other physiological explanation, but my hangovers always seemed far worse than everyone else’s. Even on days when I wasn’t officially hungover, my baseline feeling was blurgh. Or perhaps urrrrrkkkkkkk.

I was not a well man.

Then one morning, a few weeks after getting sober, I woke up feeling great. Better than great. Spectacular. It was as if someone had crept in during the night and injected me with whatever that spider injected into Peter Parker. The sun seemed to shine brighter, food tasted better, and my skin and hair had lost their greasy sheen.

It took me a couple of days to realize out what was going on: There had been no radioactive spider; my body had just finally gotten over its decade-long permahangover.

This, I now remembered, was how non-alcoholics felt when they wake up in the morning. Un-sick, un-nauseous, un-palpitatey. Just bright eyed and bushy-tailed and ready to face the day.

Since getting sober, I rarely feel sick. I don’t have any allergies, I don’t suffer from migraines, I almost never get colds, and somehow I even manage to avoid whatever virus Eli and Evie bring home from school. It’s as if my body got so good at keeping me alive as a drunk that I now have a super-charged immune system. (Note to doctors/scientists reading this: I’m aware I’m starting to sound like Bill Shine’s wife. For the avoidance of doubt, I don’t think getting sober is good for the immune system.)

On the rare times I do get sick, it feels like a strange déjà vu. When Sarah and I went to Mexico for this past New Year, I was struck down for 24 hours with food poisoning. I spent those 24 hours mostly curled up in a ball in our apartment, only uncurling myself for frequent sprints to the bathroom. As my body purged itself of everything I’d eaten and drunk in the past 24 hours, I thought back to all the times I’d been similarly sick during my 20s, but put the symptoms down to a particularly nasty hangover. Had any of those episodes actually been food poisoning? Statistically I suppose they must have been, especially given how frequently I traveled and the crap I used to eat.

Come to think of it, how many other times had I misdiagnosed other actual illnesses or viruses as hangovers. Had any of those daily headaches been honest-to-god migraines? Might the heart palpitations have been something more serious?

A few weeks ago I wrote about how, when I was drinking, I automatically assumed that every argument was my fault. How jarring it was, on getting sober, to learn that occasionally other people can be assholes. It required re-learning how to argue and, more importantly, how not to argue.

Similarly, it’s good to be reminded that even non-drinkers can get sick, and that getting sober is just the first – definitely not the last, or only – step towards taking care of myself.



First off, thank you to Katie for the hat.

Now, let’s talk about my impeccable sense of style…

When I am an old woman I shall wear purple
With a red hat that doesn’t go, and doesn’t suit me,
And I shall spend my pension
on brandy and summer gloves
And satin sandals,
and say we’ve no money for butter.

— Jenny Joseph

In my early 20s, I discovered a great hack for getting away with being an alcoholic in London: Don’t dress like a drunk.

Back in those days, if you saw me staggering out of a nightclub or into a pub, chances are I’d be wearing a dress shirt with french cuffs, probably with a jacket. Possibly a cashmere sweater. But never, ever a t-shirt.

Understand, this had absolutely nothing to do with vanity, or style (I had plenty of the former but none of the latter) but rather it was a question of practicality. As readers of The Upgrade will know, back in those days I was something of a master of “blagging”: That is, talking my way into fancy parties or night clubs or conferences in order to score free booze and other entertainment. I also liked to hang out in members clubs, and other places where rich and important people could be found.

One thing I figured out very early: A blagger can be a drunk, or he can be dressed like a drunk, but never both.  I lost count of the number of times that I was whisked through a velvet rope with a story about a lost invite, or some very important message I had to deliver to a VIP, while my far more sober (but t-shirt clad) counterparts were left behind in the cold. A drunk man walking though a hotel lobby in a suit is far less jarring to a doorman’s eye than is a sober man in torn jeans. (This, by the way, is why I continued to carry a Blackberry long after everyone else moved to iPhones. I mean he seems jobless and wasted but he’s on a Blackberry…)

When I got sober, and stopped living in hotels, I also stopped spending money on clothes. Instead, every few months, I would trudge to H&M (the sartorial equivalent of a UN food bank) and fill a basket with the cheapest, blandest t-shirts and hoodies I could find. I no longer had to disguise myself as a functioning adult, so I fell easily into the uniform of Silicon Valley.

The great thing about shitty clothes that don’t really fit is that even if you start to put on weight (as I did when I moved to Vegas), they still don’t really fit. A hoodie hides a multitude of dinners.

Fast forward to present day. Or specifically to the start of last year, by which time my closet (actually, a couple of drawers) was entirely engineered for comfort. I hadn’t realized quite how out of shape I’d gotten until, around last March or April, I found myself with only one pair of jeans that I could still barely squeeze into. The true nadir: The night Sarah and I went for dinner Calistoga and I couldn’t order dessert because (I shit you not) I was worried I wouldn’t be able to fit into that last surviving pair of pants the next day.

Something – not just the pants – had to give.

As regular readers will know, Sarah and I have spent the past few months killing ourselves at Orange Theory Fitness and Soul Cycle. The net result, apart from exhaustion and endorphins, is that I’m back to my ideal weight for the first time in three years. The downside: Before long I discovered all of my clothes were suddenly far, far too big.

As I stood at that sartorial crossroads – this would have been November or December of last year – I found myself thinking back to the clothes I used to wear in London. I turn 40 in 2019. Forty! Isn’t it ridiculous that I dressed more like a grownup when I was a drunk manchild than I do now as a 10-years sober author/founder who hopes to be a role model to two children?

I look back at photos of my dad around the same age and every one of them shows him dressed like an unequivocal grown up. Yes, he had to wear suits for work every day, but even on vacation, he always dressed like an adult (and indeed, still does.) One of my earliest memories involves me staring at my dad’s well-ordered tie collection and his rack of shiny dress shoes (not to mention his dress kilt, for formal highland occasions) and somehow understanding that these were the trappings of responsibility and maturity.

Every time I walk past Uber’s HQ and see the flow of identically schlubby proto-trillionaire sociopaths flooding onto Market Street, I’m reminded that grown men in startup t-shirts and baggy jeans is how San Francisco got into this fucking mess in the first place. And then I’m horrified at the idea that someone might see me in my H&M hoodie and think I’m one of those irresponsible, immature assholes.

Also, did I mention I TURN 40 THIS YEAR? Like the old woman who can finally wear purple and a red hat that doesn’t go, I literally can wear whatever I want. Sarah has written about this too: How once she became a mother and neared 40 she could finally channel her inner rodeo clown, with amazing cowboy boots and yoga pants paired with… wellI mean.

Perhaps that sense of liberation is what subconsciously pushed me through the doors of Tailors’ Keep – a made to measure/tailoring shop hidden in the shadow of the Transamerica building. Consciously, what drew me there was a Google search for somewhere that could re-hem an old pair of trousers and undertake a few other long-overdue repairs.  The Yelp reviews for Tailors Keep were tremendous – and from there I found this article about them in the Wall Street Journal, and this one in the Chronicle.

Still, I walked into the shop intending only to get those pants adjusted. Really I did. But then I was confronted with shelves piled high with fabric samples, and ridiculously patterned linings and buttons! So many buttons! I mean, it couldn’t hurt to look.

Six weeks after that first visit, I was the proud owner of a new, perfectly tailored suit, and two shirts made to my precise specifications.

Sarah’s reaction to just the suit was enough to dispel any possibility of spenders’ remorse. In fact, the per-garment price tag was less than I used to spend in my drinking days on clothes that didn’t fit anywhere near as well.

A few weeks after that I returned to collect four pairs of pants in a variety of tartans and stripes. Next: More shirts, and almost certainly some more jackets… the foundations of an entirely new grown-up wardrobe, in fact, tailored to exactly fit my new healthy self.

My god, where has tailoring been my whole life? Never mind the fit, or the quality, or the value for money…  who knew that there was a place in which you can sit in a big comfy chair and point at swatches of red tartan or purple stripes or Lichtensteinycartoon linings and a man with a tape-measure will transform them into an honest to god jacket?  

As Ryan – one of Tailors’ Keep’s founders – measured me for the suit, I realized another benefit of tailored /made-to-measure clothing: Accountability. My suit was due to be ready during the first week of January – which meant an entire Christmas clusterfeast lay between fitting and that first try-on. There was simply no way I could risk being unable to fit into my fancy new clothes because I couldn’t hold back from a second slice of pie.

(NB: I know I know: Food/fatshaming is bad. But what’s also bad is being a former alcoholic who, like a lot of recovering alcoholics, suffers constant sugar cravings. A second slice of pie often means a third, and fourth. You do you.)

None of which is to say that I recommend tailoring as a cure for addiction, or as a cure for much else except a surplus of closet space and a healthy bank account. But as a reward for ten years of sobriety, never mind all these months of gym-going, it’s hard to beat a pair of ridiculous green pants and a jacket with functioning sleeve buttons.

It’s also nice to know what it feels like a grown up, at last.


A slightly late, slightly truncated update this week. I’m in Malibu (pictured above, at its best) on a work trip, racing to write the newsletter in the bar of a Sheraton, sheltering from a combination of lightning storms, flooding and mudslides, exacerbated by the recent wild fires.

Question One: Why would anybody, let alone anybody rich, choose to live in this fucking hellscape? One element conspiring against you might be a sign it’s time to move – but all of them?

I’ve had a busy week. Before flying to LA, Sarah and I hosted the employees of Chairman Mom for a “team retreat” at Cavallo Point in Sausalito. We used to host similar retreats for the Pando team, and they were always productive, and fun. There’s something about being out of the office that helps focus, and encourages big ideas. Also, the food is better.

Chairman Mom is the company Sarah and I started a year or so ago to help working women (in particular working mothers) get help with the hardest problems they face. If you’ve read Sarah’s book, you’ll understand the genesis of the idea. What you might not know is how well it’s going: The millions of dollars of venture capital raised, the thousands of paying users, and thousands more tough questions answered.

I deliberately haven’t written much about Chairman Mom in the newsletter, or anywhere else. Similarly, even when I do talk about the company, you won’t hear me describe myself as co-founder.

There’s a reason for that.

When Sarah and I decided to start the company (the first company we have actually founded together), I knew two things for absolute certain:  It was going to be the biggest, and most important startup I’ve ever helped build. And two: A company called Chairman Mom absolutely can’t have a male co-founder.

If you know how Silicon Valley works, you know how much bullshit female co-founders face. How they’re diminished and overlooked. How investors only direct their questions at the guy in the room. In the case of Chairman Mom, that’s less of an issue: Only the dumbest of investors could fail to grasp that Sarah is the CEO, or that the ideas described in A Uterus Is A Feature Not A Bug are the driving principles behind everything we do.

Still: It’s important to send the message loud and clear: From the top down, this is a women-led company.

But that’s not the only reason I rejected the co-founder title.

Post-#metoo, men – particularly straight white men – find ourselves divided into two camps. In the first camp are those of us who recognize it’s high time for women to take the microphone; for female CEOs to be funded; for more qualified women to be hired and promoted. If that means fewer opportunities and less stage time for we poor downtrodden dudes, then okey dokey. We’ve had hundreds of years to take advantage of the biases in our favor and it’s our fault if missed our chance.

The second camp – well, you know the second camp. The men’s rights activists, the whiny Lindsey Grahams, the sadsack mediocre middle managers who huff and puff and sulk about how promotions should go to the “best candidate,” regardless of gender – oblivious to the fact that if “meritocracy” was ever actually a thing, then those same sadsacks wouldn’t have deserved even a millionth s of their current middling, bitter station in life.

Y’know, Trump supporters.

I’m assuming, if you’re a man reading this, you fit into that first camp. So what’s a white dude to do? Stop trying to be a founder, or a CEO? Stop going for that next promotion, or applying for that new job?

That question hit twice as hard for me. My entire career has been one long cry of LOOK AT ME. From writing memoirs to founding NSFWCORP to… well… this newsletter, I’ve put myself and my ego to the forefront and profited handsomely from it. How should that change if I no longer want to be that guy but still want to do my job?

Should I not start (or co-found) another company?

Wrong question.

Right question: How should I start (or co-found) another company?

The answer was obvious: Work alongside Sarah to build Chairman Mom, a company where I can apply everything I know about building community, and subscription businesses, to solving an honest to god huge problem… but where putting myself in the spotlight would be an honest to God disadvantage.  

It isn’t just a moral imperative, and it certainly isn’t some noble chivalric gesture: It’s sound business. As Sarah outlines in her book, female-founded companies (especially those with diverse teams) consistently outperform male-founded, less diverse companies. Who doesn’t want to jump on that statistical freight train?

There are, of course, downsides to this approach. For example, the fact that Sarah is currently at the “Upfront Ventures Summit,” snacking on hors d’oeuvres and listening to speakers like Stacey Abrams and Deray McKesson and the freaking dude from Bird scooters, while I, her invisible, non-invited co-founder, am left to trundle around Malibu in a rental car, hunting for a Soul Cycle studio in the pissing rain.

And, yeah, it’s hard for an egocentric memoirist to rendered invisible in the press, especially after NSFWCORP where I was front and center for three years. (Amusingly, the one article in which I’m mentioned as a co-founder of Chairman Mom, the interviewer focuses more on my role as Sarah’s boyfriend.)

The upsides, though, far outweigh the downsides. With all that NSFWCORP attention came constant fights, the need to be on Twitter or behind a microphone, throwing punches and absorbing jabs aimed at our writers. As the face of Chairman Mom, it’s poor Sarah who has to deal with all that bullshit, just as she has to respond to the endless press requests and go to (hopefully not endless) investor pitch meetings. Meantime, I get to spend time actually building the product and managing our otherwise 100% female team. Which is to say, doing my job.

And here’s the best part: If all goes according to plan (/a miracle occurs) and Chairman Mom becomes Silicon Valley’s next billion dollar company, I’ll still get just as unspeakably rich as I would have done with “co-founder” on my business card.

Then I can use all that money to buy a gigantic house in anywhere but fucking Malibu.

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