San Francisco Sleepathon… is coming!

Sleepathon in San Francisco

Majesty and Misery

A few months ago I was compelled to write an ‘open letter’ (

I suggested I’d organise a ‘sleepathon’ in San Francisco in aid of the homeless. The response has been amazing – if we can get just a few more people to sign up, it looks this event will happen in September!

If you’re bothered by the homeless problem in San Francisco and want to help, please share this letter and sign up here

Why a Sleepathon? San Francisco is one of the most extraordinary places in the world. The scope of opportunity, innovation, energy and entrepreneurship remains unparalleled.

Yet despite this and the wealth that has accumulated, the city disappoints if measured by the way it looks after its less fortunate. The American dream here is enjoyed by a few, sandwiched next to the American nightmare.

After writing the last letter, I’d expected little or no response, perhaps criticism. After all, who am I to suggest such an event? What good would it do? Shouldn’t we leave the problem to the State, or to those more experienced? Is it hypocritical for a bunch of privileged people to have a jolly one evening? So familiar are the problems on Market Street or in the Tenderloin that many people believe the scale of the issue is beyond tackling, or worse still, feel apathetic or no longer notice. Yet it makes me feel a bad Samaritan, impotently witnessing desperate scenes whilst ‘living the dream’.

Amazingly, my last letter struck a chord and responses flooded in, including interest from some very high profile residents willing to participate. Given that support, I’m willing to invest a few weeks of my time this year to try to make it happen.

I envisage a night in a safe space – a park, a hall or a public area where people stay for the whole night. A night of fun, with music, an auction, talks by those who understand the problems and a hackathon in which participants can brainstorm ideas that might help. Perhaps even a little bit of sleep if we’re lucky, alongside friends and supporters.

We might all be a bit tired the next day. Let that be a badge of honor, demonstrating a willingness to do something. At the very least, we will have learned a little and had some fun – at most we might raise some money and awareness.

Please sign up to join us here – – and please, please do forward this on. If people don’t sign up I’ll take that as a lack of desire to make this happen – no hard feelings, but in the spirit of entrepreneurship there’s no point dedicating a lot of effort if there’s little interest.

Please do get in touch if you’ve any thoughts or questions. I look forward, I hope, to spending a night with you in September.



Sleepout Crowd

A sleepout in the UK




A few months ago I wrote this ‘open letter’. The response was amazing and I’d like to see if I can make this event happen in September in San Francisco – so I wanted to repost this here and then I’ll follow on with more details shortly.

If you’re interested in joining (or if you’re not in San Francisco, at least helping out) please a) sign up and b) send this on to friend, family and lovers in California. Thanks!

Dear Greg,

After reading your post last week, I need your help to organize a Sleepathon – (anyone can sign up here).

I am a homeless man, living in the Bay Area. But I’m also not that dissimilar from you – I am an entrepreneur with a new business, currently on 500 startups. Fortunately for me, my homelessness is a choice.

When I read your post last week, it deeply upset me. So this weekend, I went down to Market St this weekend to talk to a few people on your behalf.


Sadly, this guy pictured can’t join one of your hackathons as his hands are in really bad condition, which is why he’s homeless as he can’t find work. He was also wearing a number of medical bracelets – he is a very sick man.

Despite having very little, he offered a flower as a sign of peace as well as a hug. He was dirty, as you rightly noted many of the people in the area would be. But in my mind a hug outweighs the inconvenience of a bit of dirt.

The people I spoke to seem to differ in opinion about the feeling that ‘it’s a privilege to be in that part of town’. They think the opposite, as this article indicates – they see it as a curse to be squeezed next to the rich.

In your open note, reported here you said:

“It’s a burden and a liability having them so close to us. Believe me, if they added the smallest iota of value I’d consider thinking different.”

Greg, they see it as disturbing having you so close to them… At least you get a comfortable bed at night, whereas they often have no-one to turn to and nowhere to go. It’s way worse for them because it’s far, far harder to look up at someone who has all the opportunities that life can offer from rock bottom, without opportunity or hope, than it is to look down and watch your step. Many of them are very sick, physically and mentally – you might want to read this article by Russell Brand who eloquently writes about the struggles with addiction here.


Which leads me to my request for help. You organize hackathons – it’s time to do good by your position. You are clearly disturbed by the presence of so many homeless people. So, rather than chastise you for your remarks, I want to ask you to help them.

I too am disturbed by the number of homeless, desperate people in San Francisco. As an entrepreneur with the capacity and opportunity to help, I would like to do something about it.

I propose we organize a Sleepathon, building on your success organizing such events. Imagine a night where we encourage as many people as possible, the extraordinarily privileged tech entrepreneurs especially, to sleep out for the night and raise money for the homeless. Could we get Mark Zuckerberg, Ev Williams, Kevin Rose and others to join us to sleep out for just one night? If we got a thousand people to join us and asked their friends and colleague to sponsor them, imagine what we could do.

Perhaps we could find somewhere a little more comfortable than Market St for you, like Dolores Park? Have you noticed how cold it’s been the last few weeks? Some homeless people froze to death. These are people’s parents, children and siblings. Perhaps we can organize the event for the spring, when it’s a bit warmer too – giving us some time to get ready? Who knows, like my current ‘homeless’ situation, perhaps it could even be fun?

Let’s use the unfortunate nature of your recent publicity to raise awareness, money and show support for these poor souls who haven’t been caught by the same protective layers of society that helped you and me.

Are you with me? Sign up here to register interest.

Yours in anticipation,

Tom Savage

PS – PLEASE SHARE THIS letter if you want it to happen – I’ll organise it if there’s enough interest (even if you don’t get in touch, Greg!)

Trapped in Escapism

In flight...

SimpleTom in flight…

One of the wonders of the modern world is opportunity.

As an entrepreneur, I’m continually excited by what is possible. Aided by lightning fast connectivity, jet engines, computing technology and a plethora of beautifully indexed information available at our fingertips… the world is our oyster, lobster and winkles too.

In a single week, an indefatigable person could dine in a San Franciscan Michelin-starred restaurant, walk through an African slum and give a talk at Davos. Another might kitesurf, skydive, go to a sex party, take mind-altering substances, play a gig at Glastonbury. Why stop there… why not combine the two?

It’s all possible if you read enough Tim Robbins, Tim Ferriss, Hello magazines or believe the latest Hollywood blockbuster. It’s just so disappointing we can’t clone ourselves because life is too short, you’ll get all the sleep you need when you’re dead and time is money.


I wonder where the being there for your friends, reading Bill Bryson on the toilet, doing some community work, empathy, writing, having an evening to think, meditation, going for a walk, sleeping well, responsibilities, calmness and, of course, simplicity fit into all this?

Have we made opportunity and escapism a fetish that undermines our ability to live healthy, happy lives?

This evening, back in London town, I have a couple of hundred restaurants and bars to choose from within a couple of mile radius. I’ve a few dozen applications, websites and guidebooks to help me choose them from and 7 devices in this house I could use to do so. I can tickle almost any gastronomic whim. With the means, I can go anywhere and do almost anything. Boy, isn’t it great to have all these options. I need to have options, otherwise my life is stale and we’ve wasted all this development and human endeavor.

I think not.

Do we even notice the joy of drinking a cup of tea, with leaves that have slowly grown and been picked by a 5th generation farmer on an Assam mountain-side? How many gastronomic delights are wolfed down, or sensations are given almost no attention, despite their wonder?

On a personal level, whether affected by these external forces, or driven by my own upbringing (being a professional musician aged 8-12, with all the discipline, restrictions and constraints that accompanied, was not at all healthy) – I’ve started to recognize that I’m trapped in what seems like a global pattern of escapism.

In fact, I’m really rather brilliant at it.

For me, the manifestation has meant that over the last 10 years, I’ve lived in lots of places, met loads of people, holidayed and partied across the globe. I’ve started a number of projects and finished very few. I’ve dated some wonderful people who I usually abandon because like all good entrepreneurs, I need an exit strategy, or just because if I’m not about to escape or if I don’t have an obvious alternative or escape plan then [alarm bells] my options are limited.

How sad. The kaleidoscope of opportunity has cauterized continuity and community.

Don’t get me wrong, it’s often been fun. But, I’ve noticed loneliness in myself and others who pursue these tantalizing escapes, scrapes and adventures. In the midst of being Peter Pan and chasing freedom, I’ve too often found myself alone, somewhere between one place and another, one relationship and another, and one piece of work and another. When the music stops, the escapee can find themselves without a place to sit. When I read stories of billionaires and their multiple homes, wives, yachts, interests and hyper-dysfunctional families, I am reminded that choice is a burden. When I look closely the eyes of those chasing ‘the capitalist dream’ at ‘exclusive’ events, I’ve started to notice the fear, loneliness and desperation behind the tanned, moneyed pearly-white smiles – which seems to get worse the closer these dreams get to fulfillment.

Recently, I’ve noticed a shift in myself to want to settle and to take on responsibility and commitment, even if it means I’m not as free. I’ve noticed that freedom comes from these commitments rather than from opportunity. With a solid and stable home, meaningful consistent work, regular friends and monogamous relationship, I sense we have the foundations upon which to be even freer, rather than chasing the elusive idea that freedom comes through keeping our options open.

Let Go – Simply Letting Things Happen and ‘Down Time’

Are Simplicity and Starting a Startup Compatible?

The answer… honestly – No, not really.

This is a really beautiful opinion piece in the NYT about those people who say they’re ‘busy’ whenever you speak to them.

I heard that the founder of Green & Blacks chocolate, I forget his name, hired such brilliant people around him that he only came in once a week to make sure everything was going according to plan. What a legend. What trust. What simplicity.

For the rest of us, the startup world is one of obsession and comes at the expense of emotional or simplicional health.

That’s not to say it’s not all bad. There’s something wonderful about focus, learning, meaning and being immersed. There’s a clarity and simplicity in the single-mindedness that a wannabe entrepreneur has on that mission.

But it’s not all good.

In my case, I look back at the last 10 years and realise, my extended sabbatical in Kenya aside, that the entrepreneurial grip has me so tight that I’ve not had energy for other things. That’s not to say I haven’t done a lot of other amazing activities – my innate sense of mischief and wanting to maintain a social life mean that I find it difficult to do nothing else but work – parties, festivals, holidays and dinners have all been attended, and enjoyed.

Yet there has been a price paid, which has been my inability to tear myself (and my ego) away from the pursuit of the entrepreneurial dream, emotionally – meaning that I’ve often felt half-there, half-not-there when out of the ‘office’.

I’m not sure I’ve truly been able to let go (this is a link to one of my best friend Jim Kroft’s song – Let Go, which encapsulates this emotion perfectly – ).

What I would give for the ability to immerse myself in the work and then enjoy the down time. Each fully. Is it possible? Did Steve Jobs ever have down time, so singular was his mission and focus? I read articles that said he worked as hard when he was ‘on holiday’ with his family as he did when he was ‘at work’. Is that the price of ‘putting a ding in the universe’.

It is partially bravery and fear. The ability to trust, like Mr Green & Blacks. Is it a desperate need to achieve and the ego, which means that everything feels undone, or still to do… despite achievements.

Time to allow things to happen to Let Go.

Tech Startups and Simplicity

Over the last few months, I’ve immersed myself in the world of the internet startup, funny little world that it is (to many within, it is there whole universe – please remind me of this as I delve deeper into the labyrinth).

Never has so much money and time been spent on so many lines of code that to most of us, make absolutely no sense at all.

Those that win, win big and fast – creating young billionaires/millionaires. But like every ‘hot’ market, the higher-profile-characters are a lucky few – many, many more toil unhealthy hours in the pursuit of e-recognition and riches.

There are obvious challenges to the simplicity-seeker here, for example:

– The reduction of in-person interaction, relying instead on the virtual

– An unhealthy desire for riches which, when obtained quickly, result in a lottery-win style appreciation and mass envy even though there is evidence of little contribution to overall happiness and some rather outrageous spending habits

– Building technology to solve problems that before we built all this technology weren’t problems – solutions layered on problems, layered on solutions

– Waste – mind-boggling amounts of people working on algorithms and sites that serve no purpose initially or eventually – the Mary Celestes of the web, of which there are many millions more than there are Facebooks. Although in fairness, the same can be said of many other areas of life

– The work ethic, which seems to promote the ‘every-waking-hour-in-front-of-a-screen-is-the-only-way’ approach

Yet there are also some fascinating lessons for simplicity:

Today, simplicity rules when it comes to web startups – in design, user-experience, products and even methodology.

The advice of the moment is to build only what you need to – be lean, create only a minimum-viable product (MVP) before you launch. My favourite simplicity quote, ‘perfection is achieved not when there is nothing more to add, but nothing left to take away’ (Antoine de Saint-Exupéry) is never more relevant than in the tech scene at the moment, where people are being encouraged to kill features, rather than add them and to make startups as simple as possible in order to test assumptions.

Entrepreneurs are being advised to run their businesses like a meditative mind – removing all unnecessary noise and focusing instead on the present moment.

Consumers too, are demanding simplicity in terms of user experience (UX) and some of the greatest successes are those that have enabled us to simplify.

Google – their home-page design is one of the simplest of the web (and the most popular)

Dropbox – as simple a file-sharing service as possible

Apple – a UX which works, is intuitive and has a simple elegance

This article, which I mentioned long ago in a similar post, talks about simplicity as a source of competitive advantage:

Technology is good. But my sense is that many people are developing it for all the wrong reasons in ways that are unhealthy and make little sense.

Over the coming months, perhaps years – if things go according to plan – I will be further immersing myself in this somewhat bizarre, much-feted world and, I hope, retaining an iota of my simplicity ideology and a balanced life.

Technology enables me to work almost without interruption from my house (although I write this from London) – the question is whether or not I’ll get there as often, whether I can build something that makes the world a little simpler and whether or not I can achieve a balance in my own life as I go.

Beautiful Technology

Simple Wealth

Simplicity does not mean you have to abandon material wealth. I’m still a firm believer in the idea that money is important when you earn it and use it correctly. Having more money than you need is a wonderful thing, if you understand what it is good for and what it is not.

Here are a few things I would like money for:

  • Living in a nice home. It doesn’t have to be big and ostentatious – but comfortable, warm, homely and not in danger of being repossessed. Preferably in a nice neighbourhood which is lively, safe and fun – it doesn’t have to be a posh neighbourhood, one with a strong community bond is best. I’ve always enjoyed my neighbourhoods when they’ve been less wealthy, offering a mix of people from different backgrounds.
  • Adventures
  • For starting up ventures and projects that help people
  • To enable you to do what you are passionate about
  • Good, healthy food
  • Experiences – the arts, festivals, city breaks, and interacting with nature
  • Freedom – to be spontaneous, or not to earn for a while if needed.
  • Learning and courses – from language to yoga, acrobatics to therapy. To afford the time, materials and lessons to learn.
  • Health – to have enough money to afford healthcare when needed.
  • Buying time – for love, for friends, for sharing, and for being generous when people need your help
  • Going to see people who you love
  • Books, music and films

What money is not for…

  • Showing off and ostentation
  • Watches, personalized number plates – items of zero utility
  • Labels – purchases whose only means of differentiation is the brand name, rather than the quality of the material
  • Club / First class travel – if you can’t last a few hours without creature comforts, you’ve lost your freedom to explore the world as it is, rather than as you’d like it to be
  • Expensive bars and eating in expensive places with people you don’t like – when the experience is more about being somewhere, than with someone, you’re missing a trick
  • Magazines, newspapers, and subscriptions.
  • Unnecessary gadgets and applications
  • Hit men

Think back to periods of your life when you had much and when you had little. Do you remember your possessions, or what you were able to do with them? Do you remember the car you drove or the journeys you went on?

Can you remember your best holiday ever – did you travel executive class (club or first) to get there? Given what a wonderful holiday it was, would you have rather spent an extra two to three days in a great hotel/bnb on arrival and taken some unpaid leave than have spent the additional £2k+?

I was once given the opportunity to live in an $8 million house in San Francisco with seven people in the nicest neighbourhood – instead, I went to live with three people in a $500k apartment. I’m reasonably sure I had a better time in the latter than I would have in the former, purely because of the neighbourhood, the experience and the people.

Paddling down the Mangoky River in the heart of Madagascar - a priceless adventure