Daddy, Why is That Man Homeless?

...323 days to go...

A few years ago, I headed to Northgate Mall with my then six-year-old daughter Natalie to pick out a home theater system for my new apartment in downtown Seattle. It was a cold, overcast January day, and as we walked from the parking garage toward the store we passed a homeless man dressed in heavy coats and a blanket. He was holding a sign that said “homeless - every dollar helps”. Natalie, who questioned everything at that age, asked the obvious: “daddy, why is that man homeless?”

I stopped, hesitated, then knelt down to her level, offering a platitude about how some people got down on their luck sometimes and gave her a dollar to offer to the man, which she hesitantly delivered. When she got back, I could see she was clearly unsatisfied with my answer. “Jeff Bezos has over a billion dollars. Can’t he help that man get a house?” I realized at that moment that six-year-olds have a remarkably clear understanding of wealth inequality, and that I was about to get schooled in economics by someone who still needed help tying her shoes.

I don’t know what happened to the man, but the scene stuck with me because even a kid could easily see the hypocrisy. Of course we could have given him more than a buck, right? And of course the richest society in the history of the world could have helped him find a place to live… right?

At the time, I felt I lacked both the time and money to improve anyone else’s life. I’d recently started a new job as a consultant that required me to travel three or four days a week and work around the clock. And I was in the middle of a contentious divorce so I didn’t really know what my finances would look like.

The memory gnawed at me over the years, until two things happened that convinced me I should - and could - do something to help.

First, my finances improved, from both landing a job at Amazon and - by marrying Jen - becoming a two-income family. Amazon paid both of us well enough that we now fall in the top few percentage points of Seattle household incomes. It’s fairly easy to argue those richer than us should be more charitable (and they should!), but if we can’t help, I suppose the pool who can starts to look pretty small.

Second, the torrent of political chaos unleashed last November affected me strongly. Jen and me, along with our baby Rosie, had travelled to Phoenix to canvas for Kamala Harris. Rosie turned her cuteness dial to 11, and was surprisingly effective at opening doors and getting undecided voters to speak with us. Who’s going to slam the door on a baby wearing a democracy t-shirt?? I’m fairly certain our efforts generated at least two additional swing state votes for Kamala, but obviously it was not enough.

The outcomes - including the “feeding of USAID to the wood chipper” and the rollback of over $1 trillion in aid to the nation’s poorest in the form of Medicaid and SNAP food benefits as part of the “Big, Beautiful, Bill” - have convinced me that now is a critical time for action.

Third, Amazon made some decisions which I felt I could no longer be a part of. I worked for a “stealth team,” so unfortunately I’m not allowed to share too many specifics. I can talk about stories already in the press, however, such as this one discussing Amazon destroying millions of brand-new products. I observed and objected to similar activities but was overruled. Several decisions made by Jeff Bezos also contributed to this feeling, including his realignment of the Washington Post editorial page (he also owns the Post) to “exclude viewpoints opposing the pillars of personal liberties and free markets” and censor the Post’s planned endorsement of Kamala Harris. In ways large and small, all of these decisions at Amazon appeared to prioritize profits over even fundamental decency. And because I feel the company I worked for (and perhaps even some of my own personal decisions) caused some harm, I’d like the next phase of my life to do some good.

So I took my “promotion to consumer” in May, 2025 and set out to see how much I could help people like the one Natalie and I met that day and gave a dollar to. Because, to answer Natalie’s question: Jeff has not done that much to help that man get a house.

I don’t want Rose to have to ask the same question, and if she does, I definitely want to have a better answer.