This book has affected my views on philanthropy, social entrepreneurship, and the role that "winners" (often times the successful, IPOed elite that we idolize here in Silicon Valley) play in lobbying for/maintaining the system that actually drive the income inequality we see today. That is the reason for my stars. One less star because this book didn't exactly equip me with the ability to change my friends' minds (not enough evidence/case studies that I can easily cite), but I will still steadily try. I encourage my friends--especially those of you in business and tech who are inspired to do good, help people--to try this book. Feel free to be a skeptic, but at least hear what all the "billionaires should not exist" argument is about. Note: this book does not argue that view exactly, and argues something much more nuanced.


A few takeaways (non exhaustive):
1. Generosity =/= justice. You can give kudos to Mark Zuckerberg for declaring that he'll give away his wealth and solve inequality, but you cannot forget to question how he himself has fought for and benefited from policies that help him build his wealth. On a local scale, how has his company contributed to the immense displacement and gentrification in the Bay Area? On a larger scale how has his company profited off of breaking down democracy and spreading fake news?
One great example from the book documented the philanthropy of the Sackler Family, the family behind Purdue Pharma which developed and commercialized Oxycontin. Not only did they commercialize it, they also fought against policies to limit the distribution (and make it harder for doctors to prescribe to patients), and covered up its extremely addictive tendencies. Now, Oxycontin is the star of our current day opioid crisis and the cause of thousands of deaths in the US. Historically, philanthropy has often coexisted with exploitation, like the Sackler/Oxycontin case.

2. Technical/business innovations are no substitute for civic and political activism. Yet today, people often view activism and simple things like voting with skepticism, putting more trust into brilliant entrepreneurs to solve the world's problems. I'm convinced that this is no substitute. Going back in history, the plantation owners --very efficient entrepreneurs indeed--would not have opted to prohibit slavery; on a similar note, Uber, which ushered in the gig economy, prioritizing on-demand, low cost services at the expense of workers having stable income or benefits,--will never elect to pay its drivers more or give them benefits, because that will always reduce its bottom line. I'm not against the tech world continuing to innovate, but I won't forget it's the civil rights and labor activists who have fought for, and need to continue to fight for humane and just treatments of citizens. Ideally, the corporations will opt to fight this battle too, but that's unlikely in today's system.

3. Solutions to inequality probably aren't created behind closed doors, without the participation of those who are experiencing the inequality!

4. Always ask, "how did it get this bad anyway?" We (including myself) probably think that becoming elite in business thinking is the #1 tool for being effective at social good. (Also to be fair, many people I know in Silicon Valley aren't even concerned with social good, and underresourced individuals are not even a part of the finite "world" they are trying to make better. ) Thus, it's tempting to approach a societal problem with business frameworks and entrepreneurial thinking. But before that, we should learn more about the thing we're trying to make better, and simply read the socio/political/economic history of that thing before ANY solutioning.

You cannot separate a current-day impoverished man from the company that paid him too little to feed their family, the college that was too expensive to go to so they opted to work instead, or the property tax laws that forced his public school to lay off its teachers, including the one that would've inspired him to go into law, or become an engineer.

Winners Take All is the hardest book I have ever read. Not because it was inaccessible or esoteric, but because it forced a long overdue look in the mirror.

Being in the tech industry I’ve been swept up in thought leadership, heroic philanthropy, and the promise of innovation to impact lives at scale. For a moment I was becoming more convinced that maybe the market place was in fact the best place to solve our social ills. Maybe the right combination of philanthropies and technology could fix most of our biggest issues. With each page, I slowly realized the lie I was telling myself to justify my newfound privilege in society.

I saw myself in the story of Hilary Cohen, a young idealistic college grad swept by corporate furor over a desire to change the world and make impact at scale through the marketplace. I rationalized momentarily selling out with the promise of building skills so one day I may be better suited to truly make the impact I desired in the public sector. I could have my cake and eat it too.

I saw myself in the story of Darren Walker, the philanthropist who against all odds went from poverty to riches. We share the same central questions. How do you reconcile the incompatible identity transition from a poor upbringing to another of riches and opportunity? How do you navigate the new elite social circles life throws you in? Am I too comfortable in my newfound privilege?

How do you respond to the uncomfortable cooing and admiration? “Look at Cesar… Why can’t they all be like him? He had a single mother. He put himself through school.” Even the most well-meaning, do not understand the selfish ways we contribute to a society where we increasingly make stories like mine and Darren’s impossible to continue to emerge. The largest or most frequent donors to charity won’t change the fact that for my story to emerge again, the stars would need to align yet again, but in a more unlikely way.

When you join the club of winners in society and you champion causes that ignore the fundamental structures and systems in place that led to your victory, you become complicit in the oppression that makes your success possible. The slaveholder who would rather treat his property with love and care instead of working to live in a free world was every bit as complicit as the most brutal slaveowners. True progress demands a sacrifice of privilege and power.

Those of us who ride the wave of prosperity have a responsibility to think of the people for whom this change systemically fails. We have a shared moral obligation and commitment to the public good. My promise to the world is to never lose sight of that.