The Hard Thing About a Hard City: Why I Support Kathryn Garcia for Mayor of NYC

A Full Preview of Who's In and Out on My Ranked Choice Ballot

Kathryn Garcia wants to be Mayor of New York City.

No, I mean, she actually wants to do the job.

It’s not a platform for her to promote any experiments. It’s not something she’s doing because that’s the next logical step in a political ladder. It’s not an interesting career change for someone who made it rich doing something else.

She wants this job and I’m thrilled to publicly endorse her for it as my #1 choice. She is, by far, the most qualified candidate in the race.

I don’t agree with her on every policy.

Do I think we’d be better off with a radical transformation of policing in America? 100%

Have I heard one single transition plan from anyone with data to back it up on something I trust will work? Nope. Minneapolis voted to defund but then no one could agree on what that actually meant. If they can’t figure it out in Minneapolis, I’m not quite sure how they’re ever going to figure it out in New York.

But our police budget, which has grown by over 30% under de Blasio. The force is bloated with overtime and over-policing in some areas, like the performative anti-terrorist presence on the Brooklyn Bridge that should get replaced with technology and under policing in others, like when it comes to curbing gun trafficking.

If you’ve ever run a large group of people, you know that culture change isn’t done at the podium. It’s a surgical strike of tons of tiny little details around how people interact with each other. I don’t think working for Mayor Garcia will be easy for the NYPD—but I do think it will be too easy for the union to walk all over those seeking revolution, even if I think we could use one.

What happens when the union resists a 50% budget cut? Are you really going to risk a police strike? Watch how quickly the city loses the little will it has for real change after the first kid gets hurt during a police strike.

Kathryn Garcia knows the history of some of the city’s biggest union concessions—like the two-man Sanitation truck. There used to be three men per truck and the city cut the third person. They got the union to agree to it by splitting the savings between the city and the other two workers. Having a savvy negotiator who has dealt with public labor forces before will make change go a lot easier.

I trust her to hear out the community, gather all the data, and, unlike our current Towering Ineptitude, actually make a decision—one that she believes is right for New York, not just politically popular.

Kathryn is exceedingly practical. She works towards what is possible—and will push that envelop. That’s the thing about someone who is a government systems wonk. When you know the details of the machine, you can bend it to your will. You know the way to get just about anything done if you really put your mind to it.

Plus, she doesn’t make enemies along the way wherever she goes, unlike some local pols who can’t detach themselves from the microphone and the camera whenever there’s a good… um… cockfight to be had.

In fact, she recently won an endorsement from State Senator Liz Krueger, who sat opposite Kathryn on the debate over the East River waste transfer station. This is the kind of city infrastructure, like a jail, that has to go somewhere but can make a NIMBY out of anyone when it comes to your neck of the woods. The Assemblywoman obviously fought for her constituency, and Kathryn made the best decision for the Sanitation Department as a whole.

There wasn’t a lingering tension.

It was just two professional women doing a job… professionally.

I don’t think the average New Yorker, or several of the candidates running for that matter, really understands how difficult the job is—and how many different types of people you are trying to satisfy as New York’s Mayor.

It’s actually pretty impossible, but that doesn’t scare her.

She wants to hear from angry parents about public schools. She wants to field complaints about flooded streets. She wants to wade through the nineteen different permits that it takes to open up a business here in order to get it down to one. She wants to figure out how to finance the billions of dollars in much-needed NYCHA repairs.

Bike lanes.

Property taxes.

Policing.

Buses.

Charter schools.

All of it.

Whatever delusions of grandeur I might have ever had about holding public office in NYC have gone away after talking to thousands of voters by text banking over the last month.

New Yorkers are hard.

They want everything yesterday. They want the government to stay out of their way but they definitely want the government to come and ticket the car blocking the driveway, to stop construction noise, and to solve homelessness but definitely not to put low-income housing on their street. They want the trash cleaned up, but not late at night because of the noise, but also not during the day when they get stuck behind a garbage truck and no marine transfer stations in their neighborhood.

They want shootings to end, police defunded, police stepped up on their street, more mental health support, lower taxes, and don’t even get them started on school testing.

Oh, and while she’s doing all that, the new Mayor should focus on the abuse of parking placards.

Jesus—who in their right mind would even want this job?

Kathryn Garcia does. She knows exactly what the job entails and how to get it done. Getting it done is something she’s done her entire career—from getting GPS on plows to figure out which streets already had snow removal to banning the dirtiest heating oil. She launched composting and reorganized commercial waste hauling so that there would be thousands less miles driven by garbage trucks around the city every year. When COVID-19 hit, she built a food supply chain that got meals to the neediest New Yorkers—over 200 million meals have been served.

I didn’t know anything about Kathryn before I interviewed her for The Schlep to City Hall—a podcast I started about the Mayoral Race. At the end of the interview, I turned off the record button and immediately said to her, “You can do this job.”

“Yeah, I know.”

“No, no… Like, you actually know how to do it—and no one knows who the hell you are. You need to start showing up on all the things, on social, get video out there—all of it. People need to know who you are.”

“So come help.”

And so I did. I’ve been volunteering with the campaign, gathering donations, signatures, texting and canvassing because I believe that Kathryn Garcia would, by far, make the best Mayor out of all the candidates.

Here is my theory of the case:

Being Mayor is an incredibly complex job, If for no other reason than its scale. NYC has over 300,000 municipal employees. There are nearly a million kids in NYC public schools. It has almost as many people as the next three largest cities in the US combined. Almost 40% of its residents weren’t even born in the U.S.

It has a budget of nearly $90 billion and a GDP roughly equivalent to the entire country of South Korea.

Unlike being the Mayor of, let’s say, South Bend Indiana, it’s not exactly the kind of thing you can learn on the job.

So no matter what my political leanings might be, I have a minimum bar for experience that I’m requiring for my vote—especially when the devil is really in the details. A lot of people get wrapped up in the policies—but if you talk to anyone who works within city government, they’ll tell you that whether you won or lost the day for New Yorkers tends to have very little to do with your policies. It has so much more to do with the execution of a million small things that never make the headlines of the Daily News or the Post.

To me, an organization that hits on all these tiny cylinders at once needs to be led by a competent operator. Kathryn Garcia has proven throughout her career to meet that criteria.

Andrew Yang, on the other hand, has not.

Measured by any kind of objectivity, he has not successfully run anything in a decade. After selling Manhattan GMAT in 2009, he started Venture for America, which aimed to create 100,000 new U.S. jobs by 2025. At best, it has created 4,000, but even that number is suspect, as it measures the growth of companies VFA interns are placed at after their placement.

That would be like being an intern at Google in the summer of 1998 and saying you’re responsible for 139,000 new jobs since you started.

And, call it what you will—impromptu, inspiring, ambitious—but the one thing you cannot call his Presidential campaign was successful. He raised $41.6 million and quit the night of the New Hampshire Primary, winning no delegates.

I mean, even Tulsi Gabbard picked up two.

Andrew seems honest and well-intentioned. I think he really wants to be successful at something and generally wants to help people. Yet, he seems out of his depth when it comes to issues of gender and race and that just cannot fly in New York City.

It’s not simply around understanding economic equity, which I think he has some intellectual grasp of. After all, as he would put it, he can do the math.

Time and time again, he fails to start with someone else’s perspective in mind. This “Math” slogan perpetuates a racial stereotype that he never seemed to grasp before Dr. Christina Greer called him out on the FAQ podcast about it—one that sets teacher expectations of non-Asian students lower. It never crossed his mind what that stereotype meant for the confidence of a Black student in a math class with Asian students. After Dr. Greer mentioned it, he still didn’t quite seem to get it, instead trying to play it off like he was actually making fun of the math stereotype.

Huh?

It also seems to escape him, despite her repeated dismissals of it, how sexist his treatment of Kathryn Garcia is. He constantly mentions her as his #2 choice and someone who would fit well in his administration—someone he would call on as a deputy.

To be clear, she doesn’t need Andrew Yang around to run the city, and her adoption into a multi-racial family and her success in a male-dominated department within NYC give her the kind of perspective Andrew keeps failing to grasp.

You could call these comments gaffes—he’s certainly prone to them, but we’ve seen this before in his work history. Several women, former Venture for America employees, told the NY Times that he treated them unfairly when it came to compensation and employment. According to the same article, he once offhandedly remarked that the nonprofit fellowship program might simply not be the best fit for black applicants.

His tone-deafness even extends, amazingly, to Asian groups. He wrote a Washington Post op-ed ‘urging’ Asian Americans to show their ‘American-ness’ amid the COVID-19 pandemic in the face of hate crime—as if the attacks they faced were because they weren’t waving the flag around enough. Asian groups who understand the abuse that immigrants get also criticized Andrew for his pro-policing stances, including his call for increased funding for the Asian Hate Crimes Task Force instead of community-based alternatives.

I wouldn’t mind if Andrew decided to take a job in the city to learn how the system works. I think it would be great for him to be given a very specific project for him to shuttle through the bureaucracy—like his People’s Bank idea, which is a great one. It’s incredibly expensive to be poor and the financial system can especially be unfriendly to those who aren’t putting a lot of money into it.

However, he doesn’t need to be Mayor to do that. In fact, I don’t understand why he isn’t already trying to start the People’s Bank if he’s so entrepreneurial. Andrew seems deeply insecure to me and seems to want outside validation for his entrepreneurial efforts. He spent far more of his focus on fundraising from and connecting to influential people for Venture for America than actually making the program work well.

Even on UBI, Yang’s signature position, you have people like Chris Hughes who founded the Economic Security Project pushing the issue forward more effectively than Yang, actually making it happen in Stockton, California. Yang’s been campaigning on the idea for years has spent tens of millions of other people’s money on it, but has no such progress to show for it.

These aren’t the kinds of results that would fly in a Kathryn Garcia administration.

As for the rest of my ballot, before I share who I am voting for, I’ll tell you who has absolutely eliminated themselves from consideration.

Shaun Donovan was on my consideration list. He’s a bit like Kathryn, having worked for a long time in government, except that his government experience is sitting on top of such big Federal things that I think he’s too far away from the rolling up of sleeves. He says vague things like, “I rebuilt New York after 9/11” and I have no idea what that’s even supposed to mean. But, fine, I’m sure he would have been an ok administrator—that is, until he brazenly flaunted the election finance laws through his father’s $1 million donation to his campaign.

You see, New Yorkers try to keep money out of politics in our election by using a matching program. If you can raise $250k, through at least 1000 donations of no more than $250 each, with a cap of $2000, you can qualify for an 8:1 match of taxpayer dollars. Basically, if you can create a groundswell of support, you’re in the game.

According to The City, “In an affidavit filed with the city Campaign Finance Board, Michael Donovan acknowledged he’s discussed whom to raise money from with his son’s campaign finance director. The elder Donovan also said he got a preview of the multi-million dollar TV ad campaign funded by New Start NYC.”

This should have disqualified him from the matching program since coordination with your PAC clearly violates the city’s campaign finance system. This disregard for the law, and this abuse of taxpayer money is ethically disqualifying for me.

If you want your rich dad to fund your campaign, fine. But don’t ask the taxpayers for a handout, too. Ray McGuire didn’t.

Another candidate I won’t be listing is Eric Adams. Eric is a skilled politician—not that he’s accomplished much in his time in office. He’s just really good at playing the game, shaking hands, shaking money trees. He’s probably the best one in the race at it. He once said that he was going to “out white” Scott Stringer.

On paper, there’s so much to like about him—from balancing being Black in America while also serving on the NYPD, to how he turned his own personal health situation around through nutrition.

In reality, he’s incredibly problematic. He’s never met a podium he didn’t like and has never missed an opportunity to say something divisive or incendiary—like when he said that Herman Badillo, a Latino candidate for comptroller who married a Jewish wife, “Returns to his community when he needs votes. He should have returned there when looking for a wife.”

Or at an affordable housing opening for LGBTQ seniors, Adams said “I can’t celebrate a building that is not going to be inclusive.”

Huh?

Weirdness aside, he also has a super troubling history when it comes to pay-for-play. When Adams was Chairman of the NY Senate Racing, Gaming and Wagering Committee, he and others were accused of improperly awarding casino video slot machine rights at Aqueduct to AEG, who gave $14,500 in campaign contributions to Adams. It resulted in a wiretapping probe against him.

When his handpicked successor, IDC/Dem turncoat State Senator Jesse Hamilton was locked in a tight primary, Adams directed $1mm of public funds to his district for participatory budgeting projects--the only Brooklyn district at the time to get this funding.

The city’s Department of Investigation also probed Adams following complaints that he and his staff hit up local business and community leaders for cash to fund pet projects with money to be funneled through a nonprofit that didn’t yet exist.

There is so much smoke around the BP that I cannot believe he hasn’t been burned by the fire.

But that’s not even my biggest gripe with him. Eric Adams is a cop at heart who thinks that “good guy with a gun” is the answer to everything. After a synagogue shooting, Adams suggested that off duty and retired officers should bring their guns to church.

Right, that’s just what churches need—more guns. Even the best trained good guys, active duty police officers, only hit 18% of what they shoot at.

He’s even suggested that he would dismiss his security detail in favor of carrying a gun—because that’s Eric Adams’ view of the world—that you’re only safe if you have a gun.

I hate to break it to the so-called crime expert, but that’s exactly the mentality that young people growing up in impoverished areas of NYC think, too. The shooting in Times square yesterday wasn’t a mugging. It was a dispute between two brothers gone awry.

What kind of example is it going to set if the Mayor is flaunting a handgun for protection?

This is the guy that is going to get guns off the street? A pro-gun Mayor won’t solve NYC’s shooting problem.

As for Scott Stringer, it should be fairly obvious why I’m not listing him—but for anyone who thinks, “Well, he’s innocent until proven guilty” or “it was just an accusation”, they should look at his comments afterwards. He suggested that his accuser, an intern/volunteer for his campaign at the time was “a peer” and that their relationship was consensual.

If you can’t understand the power dynamics between the candidate in a campaign and an unpaid worker, then you’ve disqualified yourself to work in powerful positions.

Ok, so let’s start with my actual ballot. I haven’t actually decided on the order yet and will probably leave that to the last pre-election polls.

Before the Scott Stringer incident, I wasn’t going to rank Ray McGuire.

Honestly, I like Ray. He has an infectious personality and he’s been a champion of NYC for years. NYC is lucky to have him around and he has been a generous contributor to a lot of organizations.

That being said, I don’t see a banker being the right person to solving the inequities facing too many of NYC’s residents. Sure, Ray grew up poor, but that didn’t stop him from being a banker to the Koch brothers on a deal that laid off more than 2,000 workers and saw its roll of union workers cut nearly in half. The Koch brothers have done more to harm the poor in this country than almost anyone and if that didn’t sicken Ray to do business with them, then that poor background story just feels a bit far gone.

People compare him to Mike Bloomberg, but Bloomberg literally built the first Bloomberg terminal from scratch. Ray didn’t build Citigroup, he succeeded within it—and it’s fairly easy to be a leader of people with than organization when you can incentivize them with million-dollar bonuses.

That’s not how cops work. That’s not how Sanitation workers work. If Ray wins, he’s going to have to learn this quickly.

He’s a good man and I think he’d do his best to do right by New Yorkers. I wish he had more government experience or managing something relevant to running the city, but he’s got heart and will, and so I don’t mind including him.

I’m going to rank Maya Wiley and Dianne Morales as well—as they probably align most closely with my political views. I just don’t see them being able to make the change they want to see from a practical perspective. I’m concerned that we’ll wind up with something akin to another de Blasio administration—because a progressive Mayor who cared about inequity was what we were supposed to get in 2013. He lacked the management savvy in order to get enough done and this is exactly the area I have concerns about them.

Still, they both come from a lived experience that it is time more of our leaders came from. I’ll probably rank Dianne Morales over Maya, because Dianne did at least run something as a CEO, and while a small non-profit isn’t nearly anything on the scale Kathryn Garcia has led, she was still where the buck stopped and that’s important. You can hear my interviews with them on The Schlep to City Hall.

Last, but not least, there’s Art Chang, who stands right now as the longest of longshots, but this isn’t a horse race. We’re not trying to pick the winners, especially not in ranked-choice voting. We’re trying to get our voices heard.

Art is a fundamentally decent person, a solid leader, a true entrepreneur (much more of one, actually, than Andrew Yang is storied to be), and he’s also familiar with lots of aspects of how the city works, having spent time on the city’s Campaign Finance Board. He’s deserving of a bigger look than he’s gotten, but he’s not a big social media personality type guy.

In the last week, since the Stringer incident, Kathryn Garcia has gotten some amazing press coverage. There’s real momentum in the campaign and I can tell you that in my conversations with voters, there’s a noticeable difference in the number of people who are supporting her. It went from maybe 1 out of 20 respondents even knowing who she is to something like a full third to a half planning to give her strong consideration, if not a ringing #1 endorsement.

It was so clearly noticeable that I even threw a few bucks to buy her on the cheap at Predict-it. Three cents? Come on!

At this point in the 2013 race, de Blasio was a distant third being Weiner and Quinn. He was a TV commercial away from pulling ahead.

There’s lots of campaign left and it’s time to break some glass.

To that end, I’m continuing my fundraising for Kathryn. If you donate $250 here, and send me the receipt to charlie@brooklynbridge.vc, I will consult with you for an hour of my time on your startup pitch, VC career trajectory—anything you think I could be helpful with.

Thanks for hearing me out and keeping an open mind.