A few weeks ago, I moved onto my friend Orion’s ranch, perched on a hilltop above Zipolite, Oaxaca and the Pacific Coast of Mexico. We’re off grid, channeling energy from solar panels into a Tesla battery that he smuggled across the border. I’m a seven min ATV ride from the beach, and I end most days with a run on the sand, grateful to watch the sun descend, and excited for it to reappear tomorrow.

I am still somewhat shocked to be here, and if April 2020 Dan learned where December 2020 Dan had landed, his jaw would have dropped…

Official first mention of 2020, complete.

“Hey Adam — give me a call when you have a sec. I have some good news for you.”

We hadn’t chatted in a few months, but when I texted my former co-founder Adam that message last week, he rang me within 30 seconds. The good news I shared with him? He owns .5% of my growing company, even though it’s been 2 years since we actively worked together, and we really only spent 6 months closely collaborating.

Here’s how it went down:

In May, 2016, I signed the incorporation documents for SlingShot Inc. I’d spent a few months tinkering…

A dramatic representation of my credit score over the last five years.

If you believe the hype, there are two ways to start a company:

  1. Pound the pavement and raise money from venture capitalists, giving away control and equity in your company and setting up expectations of venture profile growth.
  2. Generate revenue that exceeds expenses, and grow that profit to support yourself, and eventually others.

For most entrepreneurs, it’s not that neat, and it’s not that clean. I thought there might be value in sharing my personal story of financial engineering, privilege, mental health, startup failure and success, and a credit score that has swung from 830 to 690 over the last…


I am approximately 400 kilometers into my walk across the island of Cuba. I continue to feel stronger and stronger, physically and mentally — though there have been very significant challenges throughout the journey.

I will be coming back to the US for two weeks at the end of March to resupply (I also need to exit and re-enter Cuba, due to Cuban visa requirements). I hope to see some of you then!

This email has three sections:

1. The boring stuff
2. An update on my walk across Cuba.
3. Three previous emails sharing the genesis and beginning of my…


This email has three sections:

1. The boring stuff

2. An update on my walk

3. A link to photos from my walk

4. A brief report on travel in Cuba (US media is wrong on many fronts)

The boring stuff:

1. If you would rather not receive future emails, no worries! Reply with “unsubscribe” and I will remove you immediately, with my apologies for the inbox invasion!

2. Please do not forward this email to anyone without my permission (feel free to ask me, I will be thrilled you took the time and interest!). …

Yesterday I learned why Elon Musk says starting a company is like chewing glass

“Running a start-up is like chewing glass and staring into the abyss. After a while, you stop staring, but the glass chewing never ends”. -Elon Musk

Yesterday I received the note every entrepreneur dreads, coming from a great potential lead investor after three weeks of due diligence:

we really like you, we love your mission, but have questions re: the model and early days status, so we’re not over the hump. Let’s keep talking in the next couple of months, and we’ll do everything we can to help you along the way.

(This last part is why they are great…

My journal notes, one week after I arrived in Havana:

Seven days have passed since my plane took off from Cancun and touched down here in Cuba at José Martí International Airport.

The view from Supercake, my apartment building in Centro Habana

We seek comfort and context through comparison; past experiences bring order to new, complex situations. This city shares so many physical, sociological, anthropological, and spiritual characteristics with New Orleans, my favorite city in the world. But Havana is truly singular, unlike any other place I’ve ever visited, and I find myself struggling to put pen to paper.

I’ll skip descriptions of colonial architecture, classic cars, salsa music, and beautiful women. They are all marvelous and described elsewhere more…

Writing in my journal — first days in Havana.

In August 2014, I quit my cushy San Francisco startup job to ride a bicycle from Seattle to the Florida Keys. Before setting off, I told myself and others that, should money and motivation remain at the end of my journey, I planned to find a boat headed to Cuba.

The bicycle tour was truly epic — across Washington, through Idaho and over the rugged mountains of Montana, Wyoming and Colorado, till the dry, flat plains of Oklahoma, Texas, and Louisiana.

Then, upon reaching New Orleans in late November, a series of deeply personal, powerful, spiritual moments were set in…

Me, hitchhiking

Here’s what that time of my life taught me.

I opened the summer of 2005 with grand plans — but really, I needed to dream big just to maintain my sanity.

The preceding five months had been spent in wintry upstate New York, locked in the perpetual grind of my first semester of college. When I wasn’t in class, I was out drinking; when I wasn’t out drinking, I was slumbering in the heat of my dorm room.

My interactions with others were dull and lacked depth; I couldn’t seem to make relationships stick. At a university where girls outnumbered boys 3 to 1, proposing a date seemed out…

Lessons learned from my first Kickstarter project.

Last week, Queen Latifah gave me a big hug backstage on the set of her #1 rated day-time talk show and told me I smelled good. Nicest lady ever.

My journey to the Sony Lot began on Kickstarter — a platform I lovingly refer to as “entrepreneurship on steroids”, because it’s a 30 day crash course in building a business.

Hopefully, my experience can offer insight as you Kickstart your very own passion project. This by no means a step-by-step instruction guide; to really dig in, check out Soma Water’s Hacking Kickstarter.

Just remember: the most important step is step…


Adventurer. Founder, @bolt_travel (www.joinbolt.com) unlocking impossible experiences around the world. Formerly growth / biz dev @Lyft, @Getable, @subwaysets

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