For much of 2017, we had LGBT refugees from Iraq and Uganda living at our house in the Bay Area. I sent out some private reflections and anecdotes about the experience to some friends. For those especially interested in the topic, feel free to email me and I can share with you.

Here are the thoughts on philanthropy that I’ve been mulling over after the tremendously fulfilling experience of hosting refugees.

Maximizing Philanthropic Utilitarian Impact vs. Emotional Satisfaction

My favorite charity to support is Give Directly. Give Directly sends money directly to some of the poorest people in the world with no strings attached. Backed by research, I believe Give Directly is one of the most efficient ways for your dollars to help those who need it most.

The challenge as a donor to Give Directly is that you don’t feel anything when you give. The money leaves your bank account and ends up in some stranger’s bank account. Then you move on with your life. Whereas when you host refugees, you feel very emotionally involved in the experience. But helping one refugee in the Bay Area is not making a dent in the global refugee issue in general, arguably one of the most important humanitarian issues of the next decade. The “systems”/impact part of my brain struggles with this.

What I realized this past year is that our experience hosting the men was a perfect 1-2 punch. By being extremely hands-on with three refugees, we generated the emotional propulsion to care deeply about the refugee issue more generally. We then used that emotional energy to engage at the systems level: learn how the systems work, research which organizations are helping, and begin to take steps to engage in philanthropy that would be more scalable.

Doing only Give Directly or any other type of super utilitarian and analytical but ultimately feeling-free giving would be emotionally unsustainable. Doing only refugee hosting or food bank handouts, or any other type of non-scalable, super local volunteer activity would undershoot on our potential to maximize impact. Do both — that’s what we learned.

Are the Financially Poorest People the Absolute Neediest?

When I donate to charity, in my own small way I try to prioritize helping the financially neediest on a global scale. For this reason, I haven’t given much to America-centric non-profits.

That said, the refugee experience has prompted me to re-evaluate an element of this belief. To what extent is financial poverty the truest proxy of neediness? The LGBT refugees from Iraq had phones, Facebook and Snapchat accounts, and exposure to most modern technologies that we have in California. In financial terms, they were/are richer than teenagers living in, say, the slums of India. At the same time, they’ve been disowned, indeed had their lives threatened, by their own family. And exiled from their country. And rejected by their religious community because of their sexual orientation. Who’s needier?

You Can Care About Complete Strangers. You Can Love People who Aren’t Biologically Related to You.

Complete strangers walk into your house. From a different culture, speaking a different language. They shack up with you. You help them. They help you. You argue with them. You laugh with them. You begin to care about them. You begin to love them.

I now have a glimpse, I think, into how and why people adopt children. You really can love people who aren’t biologically related to you. In our own ways, we truly grew to love the refugees who lived with us.

A few weeks ago, I continued my education on an issue I’m passionate about — criminal justice reform and the prison system — when I participated in a Defy Ventures event at a California maximum security prison. It was an incredibly powerful day.

About 50 VCs and entrepreneurs, mostly from LA, trekked to the prison north of Los Angeles, under the organizing leadership of Mark Suster and Brad Feld and the non-profit Defy Ventures. Defy Ventures, in their own words, “transforms the lives of business leaders and people with criminal histories through their collaboration along the entrepreneurial journey.” Catherine Hoke, founder/CEO of Defy, is one of the most passionate entrepreneurs I’ve ever encountered — and I’ve encountered many passionate entrepreneurs.

From 9:15am-8pm we gathered with the inmates in an indoor gymnasium. The gym looked and felt like any other — except for the multiple signs on the wall that said “No Warning Shots Will Be Fired in the Gym” and for the gunner who paced back and forth from a ledge near the roof of the building, holding an automatic rifle.

The schedule was non-stop. Shaking hands, talking 1:1, listening to their business pitches. Many of the inmates were nervous: some told us that the opportunity to meet us was the biggest opportunity they ever had in their life. We were also nervous: we were in a max security prison. A day full of personal interactions with “criminals” forces you to abandon stereotypes and understand these men for who they are: human beings, flawed like all of us, but human.

The most powerful hour of the day occurred just after lunch. Inmates and volunteers lined up in two lines facing each other. There was about 7-8 yards separating the two lines, and a line of tape on the floor in the middle. We stared at each other across the line. Catherine posed a series of questions and asked us to step to the middle line if the statement was true for us. Example: “If you grew up in poverty, step to the line.” Almost every inmate stepped to the line; almost no volunteers did. “If your parents have been incarcerated, step to the line.” Almost every inmate stepped to the line; almost no volunteers did. And so on. It became abundantly clear very early on — and clear in the most visible way, as people physically stepped forward and back during the questions — that most of the inmates were dealt a set of cards in life that made “failure” a likelihood.

We were asked to maintain eye contact with the inmate standing directly across from us in the lineup. I didn’t know the backstory of the person I happened to line up across from. Then the question: “If you were arrested under the age of 17, step to the line.” He did. Then: “If you have been incarcerated for more than 20 years, step to the line.” He did. Those two questions stopped me cold. He made a mistake as a teenager, and has spent 20 years in the slammer. Are you kidding me? I choked up. Meanwhile, he maintained a steady, compassionate gaze, reaching out to shake volunteers’ hands whenever they stepped to the line.

Afterwards, I went up to him and learned his story. He was in for attempted murder — he had been out with a group of guys one night and one person had a gun and the prosecution proved there was intent to kill. I asked about his time behind bars. He said he spent several years at Pelican Bay, the notorious supermax prison in California, where the entire prison was on complete lock down for three straight years — meaning everyone was confined to their cell 23-24 hours a day. I can’t imagine the effect such isolation has on the human mind. By the end of our conversation, I couldn’t shake the feeling that this guy had been completely screwed by “the system” — the length and conditions of incarceration seemed utterly unjust.

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A year ago, I visited San Quentin State Prison and spoke to a group of 20 inmates about The Startup of You. They had all read the book and our 90 minute discussion was a mind blow — it opened my eyes to a population of people and a political issue to which I was totally blind. I wrote about my experience in this blog post.

I’ve been thinking about the criminal justice system ever since: how unjust the system is to so many, how prisons mete out punishment and yet often fail to cultivate rehabilitation, the philosophical basis for believing in redemption and second chances, among other topics.

My interest has led to me on several paths:

• A friend and I spent a bunch of time brainstorming business ideas that would serve prisoners and their families. There are more than two million Americans locked up and many of them are gouged by predatory companies that supposedly “serve” their families. Specifically, a small number of telecom companies monopolize the phone systems inside prisons and charge ridiculous fees for inmates to call their families. Is there a way to disrupt them
• I watched the Netflix documentary 13th, which is about the mass incarceration problem in America and how it’s connected to race. The film’s title is a reference to the 13th amendment which banned slavery. The film argues that mass incarceration is a modern version of racially-charged enslavement. I highly recommend the documentary.
• I’ve been reading Shaka Senghor’s moving memoir Writing My Wrongs, about his 19 year incarceration for murder and ultimate redemption. Shaka did a tour of duty as an MIT Media Lab Fellow and delivered a popular TED talk. I’ve gotten to know Shaka a little bit and find him inspiring.
• I donated money to The Last Mile and am headed back to San Quentin in a few weeks to speak to another group of men who are reading The Startup of You.

Speaking of The Last Mile, they have pivoted to a model that may, from my perspective, make it one of the most interesting programs in the prison reform marketplace of ideas: they’re teaching inmates how to code! They have set up computers in prison that let inmates code despite the computers not being connected to the internet. Coding instructors on the outside pipe in via live video chat to teach the inmates. Imagine if inmates could get paid for coding while on the inside (prisons as the new low-cost outsourcing option for companies!). And when they get out, the men possess one of the highest paid skills in the modern economy. Coding skills may be the most reliable path to economic self-sufficiency today.

Anyway, thank you to Defy Ventures for all the work you are doing to tackle one of America’s most morally pressing issues. And thank you to Brad and Mark for inviting me on the unforgettable trip.

Marc is an inspiring human being. His 20 minute commencement speech at USC this year nicely sums up his life story and how he became committed to his model of integrated philanthropy.

There needs to be a MacArthur Foundation that focuses on emerging talents. It should give no-strings-attached grants to emerging talents in the same way MacArthur does for established talents. The grants would be given regardless of type of talent, though it would emphasize those demonstrating extraordinary creative potential yet who do not have much money. (I support economic affirmative action at young levels; I do not support racial affirmative action.) The current MacArthur genius grants are terrific in that they're given to individuals instead of causes or projects, but oftentimes the people don't really need the money or recognition. This "Junior MacArthur" program would involve placing riskier bets on still unproven individuals who nevertheless display great potential and tremendous self-direction. Grantees would use the money however they see fit to make the world a better place.

The first grantee should be Colin Marshall. Colin is a talented artist. He is one of the clearest thinking writers on the web. He runs a successful radio interview program. He runs a site about podcasts. He writes columns. He writes essays. He writes blog posts. He makes films. He tweets prolifically. He's 25 years old.

But there's a problem: his work doesn't generate much money. It's always been hard to make a living as an artist or self-employed intellectual. Especially so when Colin, by his own admission, knows nothing about making money:

Kinda trippy that I've biologically persisted nearly to the age of 25 without any idea whatsoever of how to make enough money to buy a car, isn't it?…I react to the mechanics of moneymaking with the same befuddlement that many of these well-heeled vehicle owners do when they stare at the dark, occult forms under their hoods.

At present, Colin has to spend some portion of his day doing bullshit work:

…[W]hatever one could call my "creative daily routine" turns out to be highly variable, since I have to wedge it in around "regular work," that is to say, the stuff that pays me cash bucks but is not broadcasting/interviewing, writing/essayism, film/video or sound/music. (I'm not sure how much sense it makes to organize life this way at my age, but bear with me.)

He knows the bullshit work could, if he's not careful, become the real work:

I've seen more than a few people fall into this basic scenario: get some McJob or cultivate an unengaging "fallback" career to support whatever it is they "really" do; grow dependent on the entity providing said McJob/fallback; build up a lifestyle whose monthly expenditure requires said employment; gradually, imperceptibly forget about real endeavors in the name of shorter-term concerns; become some hideous institutional creature, like a blind fish that feeds whatever nutrients happen to float across the ocean floor.

In any event, some extra money would go a long way for him:

…I personally reside at the point on the curve where an extra few grand — or, say, a double sawbuck left in the ATM — can greatly widen the smile on my face. Maybe this is a bad sign for someone my age, but when I saw Sibilance link to a WSJ article about how a 22-year-old girl managed to make it in NYC on $30,000 a year, my reaction was not "Woah, how'd she swing that?" but a series of elaborate fantasies about all the things I could do with the impossible dream of $30,000. Hell, what couldn't I do? That's "thousand" with a T, people. (And yes, when I think about how Ira Glass famously made "only" $60,000 a year for a long time while working hard on the radio, my inner voice becomes Robin Leach's.)

Of course, Colin could (and should) learn more about how to monetize his talents. But beyond a basic increase in entrepreneurial savvy — which would not require selling out by the way — beyond that, it becomes difficult to do the kind of work that he does (esoteric film reviews, for example) without spending a huge amount of time trying to raise money or work dull side jobs.

If Colin could focus on his art and not worry about the cash bucks, the world would be a richer place. I realize there are a million other people who think of themselves as falling into this category. Many writers, for sure. I'm highlighting Colin because a) he's a friend, b) he's young, c) a small amount of money could go a long way for him.

Bottom Line: Someone should start a program that gives no-strings-attached grants to high potential individuals under 30 with extraordinary creative potential (yet little money), and a demonstrated ability to self-direct and self-manage. Person-driven philanthropy.

Peter Thiel has launched his foundation — The Thiel Foundation — which seeks to "defend and promote freedom in all its dimensions: political, personal, and economic."

In his essay for the Oslo Forum, Thiel writes, "Like explorers or inventors, the first one to stand up for the truth faces the biggest challenge, but creates a model for the second and third, who benefit from his example. The world needs more refuseniks, rejectionists, resisters, gadflies, doubters, critics, objectors, muckrakers, and prisoners of conscience."

He goes on to talk about the "contrarian heroes" who stand up against violence:

In human rights, a conceptual breakthrough generally involves no new knowledge, but rather the rigorous application of a principle we already knew. Libertarians talk of the nonaggression axiom, Christians of the golden rule, Hindus and Buddhists of ahimsa; and this commandment to love others is written on the heart.

Some societies suppress sympathy for the other more or less entirely. More advanced societies typically honor this principle loudly but narrowly. Contrarians who apply it have discovered and exposed the evil of slavery; conscription; persecution of speech, belief, and worship; collective guilt; war; and torture. And they’ve frequently been rewarded for their discoveries with a spot on the list of victims.

Contrarians have also discovered that these evils are driven by common temptations—tribalism or utilitarianism—and entail a common expedient, violence.