100 Gratitudes, One Hundred Dollars, and the $29,000 Birthday Swim

“With great power comes great responsibility.”

We live in a world of abundance, and this is the year that I finally became worth nothing. Out of all the things that I worked through and built this year, the entire time I still had a bed to sleep in, a family close by, a job that I went to everyday and plenty of food to eat. A pool to swim in, places to run, a city to call home.

When I returned from WDS this year, I was humbled, quiet, confused, and a bit sad: despite all of the engagement, inspiration, and learning, I still wonder: Am I doing things worthwhile? I’m not sure yet. Is there more to do? Absolutely. Have I reached all of my capabilities? I don’t think so. Can I do more? Yes. There’s so much more I want to do.

But while I sit trying to figure it out, other people walk hundreds of miles trying to find the most precious resource of all – water. A drop of clear liquid, the power of life. Some people, however, don’t have the luxury of $100. Of food, water, or a roof over their head. Of a bed to sleep in at night. Of sanitation.

So today I’d like your help with a few things. Three things, in particular.

FIRST: GRATITUDE AND THE HUNDRED LETTERS

When I got home, I sat down and started writing a hundred letters to people I’ve been grateful for meeting and crossing paths this year. A hundred letters.

I also listed out a hundred gratitudes for the overwhelming number of luxuries and opportunities present in my life. I sat, a quiet shadow in a crowded street, anonymous behind a cup of coffee, watching people laughing, wandering, and jovially interacting in front of me. Loving the life I’ve been blessed with, and focusing on each of the little things that mean so much. You can see it here.

So, your assignment, Part 1: What are you grateful for? Who are you grateful for? Tell them. Today.

SECOND: THE $100 INVESTMENT

The rumors are true. Chris Guillebeau put together a WDS conference that raised $100,000, and promptly turned around and gave away $100 to each of the 1000 attendees. He told us the parable of the man … and then asked each of us: What would you do with $100? How would you invest it? Would you make a project, a book, surprise someone, invest it?

I already have quite a few ideas. But I want to ask you: What would you do with $100? How would you invest it—in yourself, in your ideas, in your projects, in someone else, in something else?

Part 2: What would you do with $100? Let me know in the comments. 

THIRD: THE $29,000 BIRTHDAY SWIM.


There are an over 8 million people in the world without access to clean water. As I wonder what to do about the extra $100 I received from attending one of my favorite conferences, full of abundance–some people are just trying to live. The irony is not lost on me. I am grateful.

This year, as part of a promise we each made at WDS, I’m donating my 29th birthday to Scott Harrison’s quest to bring everyone clean water. It won’t solve all of the world’s problems, but it’s a start. And as my contribution, I’m asking 1000 people to donate $29 for my birthday. Instead of a birthday present, or a gift, or a meal out with your friends or family: would you join 1000 voices and donate to my birthday water campaign?

I’m asking 1000 people to donate $29 for my birthday.

I’m not sure how I’m going to do it. One thousand people. That’s a lot.

The catch? If I actually raise $29,000, I promise that I’ll do a birthday swim – in my birthday suit, nonetheless – from Alcatraz to San Francisco. 1.5 miles in cold water with nothing but a swim cap. (It will not be a spectator event, for anyone questioning out there! I will make sure to have confirmation from several sources). It will be freezing. I will be very, very cold. But a little cold and a little bay muck is nothing compared to the lives lived on other countries in this world. But only if I raise the $29K.

If I actually raise $29,000, I promise that I’ll do a birthday swim – in my birthday suit, nonetheless – from Alcatraz to San Francisco.

I’m also looking for companies and start-ups interested in donating.

Start-ups know the power of a little bit. Of a nudge. Of belief, and of what $29 can do.  It’s about the power of micro-communities, of people invested in the success of other people, and the power of 1000 voices. We have everything in SF. We’re all working our tails off, but let’s pause for a minute, skip that extra bottle of wine, and let’s do something for people who are just struggling for the right to live.

They also know the power of crazy ideas and audacity. We may be working day and night on our favorite start-ups and next projects and side-hustles, but we are able to do so because we have housing, transportation, internet, infrastructure, water, food, and other basic amenities at our fingertips.  I’m not saying this is the best way to fix the problems of the world… but it’s a small step, and it’s do-able, and it makes a difference.

Specifically, I’d like to get at least ten San Francisco Start-ups to donate $290 to $2900.

If you’re a business owner or a start-up fan, consider making matching pledges for anyone that contributes in their name. If you donate and mention your favorite San Francisco Start-Up, I hope that they’ll match your dollars to make this a reality.  As a San Francisco resident and native, and someone who loves and is invested in the power of the start-up community in San Francisco, I’d love for their help. GetAround, RelayRides, Uber, Lyft, DropBox, Twitter, Zaarly, FourSquare, 37SignalsEverest, Task Rabbit, The New Hive, ThumbTack, and all you other crazy start-ups out there: Let me do the hard part. I’ll swim the bay for you. All you gotta do is help out with $290 towards clean water.

Because to show my love for the start-up world, for San Francisco, and for the power of water, I’m willing to do something a little crazy. I’ll swim my suit off (literally) for the love of start-ups and for the love of water.

Sometimes, it takes a little crazy.

Actually, all the time it takes a little crazy.

Join me.

So, part 3: It’s a little crazy. And I don’t know how I’m going to do it. I’m asking for $29. Or $290. Or whatever you want to donate. Surprise me.

With love,

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