The Sunset Connection - Perspectives from SF's Sunset Neighborhood
The Sunset District isn’t just fog and quiet streets. It's one of San Francisco’s most dynamic west side communities, shaped by decades of migration, culture, and change. If you’re into Sunset real estate, San Francisco local history, or simply love discovering the stories behind the neighborhoods you pass every day, this podcast is for you.
I’m Jessica Ho: local realtor, community connector, and proud Sunset resident. Each episode, I sit down with the people who built this corner of the west side: small business owners, longtime families, civic leaders, educators, artists, and neighborhood legends whose stories rarely get told.
On The Sunset Connection, we explore:
- The people who shaped the Sunset District;
- The history behind the homes and institutions of west side San Francisco;
- Small business spotlights, community updates, and neighborhood culture;
- Human-centered insights into Sunset real estate;
- Conversations with Sunset legends and emerging voices; and
- The surprising layers of San Francisco local history hiding in plain sight.
Whether you grew up here, live here today, or are simply Sunset-curious, this show connects you to the people, stories, and spirit of a neighborhood that’s constantly evolving, but never losing its heart.
And if you’re curious about the market or just want to continue the conversation off the podcast, don’t hesitate to reach out
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The Sunset Connection - Perspectives from SF's Sunset Neighborhood
SF June Ballot Guide: What Is the “CEO Tax” Really? With Ryan Blake
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San Francisco voters are being asked to weigh in on earthquake preparedness, term limits, and two competing business tax measures that could shape the city’s economic future.
In this episode, Jessica Ho is joined by Ryan Blake of Platinum Advisors to break down Propositions A through D in plain English, including the debate behind the so-called “CEO tax,” downtown recovery, city budget pressures, and how competing ballot measures actually work.
Whether you already vote in every election or are just trying to make sense of the voter pamphlet, this episode aims to make the June 2 ballot easier to understand.
The views expressed by the guest are his own and do not reflect those of Platinum Advisors or its clients.
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The Sunset Connection — exploring the stories and histories that connect us.
Why These Measures Matter
Jessica J. HoOkay. Hello everyone and welcome back to the Sunset Connection. I'm Jessica Ho, a realtor with Sequoia Real Estate and host of the Sunset Connection. And today's episode is entirely focused on San Francisco's June 2nd ballot measure. What they actually do, the arguments for and against them. So in fact, the way that I wanted to kind of present the arguments in this podcast is actually in three segments. Which was we talked about prop A, then we talked about Prop B, but Prop C and D are actually two sides of the same coin. So without further ado, ready? Here we go. I know that ballot measures can sometimes feel confusing, overly technical, especially when you start reading campaign mailers, endorsements, rebuttals, and even the voter pamphlet. So my goal today is really just to make the conversation easier to follow and easier to understand so that everyone can make their own decisions. I invited Ryan Blake from Platinum Advisors to join me today and help unpack some of these measures and explain some of the broader political context around them. These measures also reflect larger conversations happening in San Francisco right now around recovery, public trust, governance, and what kind of city people want San Francisco to become. Ryan, thanks for joining me.
Ryan BlakeYeah, thank you for having me. So a little bit about my background. I started in 2010 as an intern for Gavin Newsom's lieutenant governor campaign. And then I proceeded to work on campaigns for nine years straight, which is much longer than a lot of people do campaigns. It's usually a few cycles and they get out. But maybe there's something wrong with me in that regard. Over the course of my career, I worked on around 20 different ballot measures on the campaign side. And in 2019, I left the campaign world and I joined Platinum Advisors. And so now I'm on the consulting and government affairs side, much more working with the people who are elected at City Hall on existing policy and things as they move through City Hall as opposed to when they're on the ballot and hoping they get either passed or trying to defeat something. I did want to say, just as a disclaimer, the perspective I'm providing today is that of my own and not a reflection of Platinum Advisors or our clients.
How Ballot Arguments Work
Jessica J. HoSo for anyone who's registered to vote in San Francisco for the June 2nd election, you should have received a voter information pamphlet and sample ballot. Can you explain why there's so many arguments for and against and what the difference is between the official and paid arguments?
Ryan BlakeYeah, I think that, you know, the what the way it works is every ballot measure gets a proponent argument for free. And then an opponent argument gets placed also for free, and then there's a rebuttal to each of those. And then after that are paid arguments. And anybody who wants to can write their reasoning why they believe in a proposition or disagree with the proposition, pay the submission fee, and have that published in the ballot book. And San Francisco has such a lengthy ballot most years. The fact that we only have four this year is actually quite the reprieve. Um, many years we get up into the high letters of the alphabet, and sometimes I've seen V and things like that. So All right.
Prop A Bond For Preparedness
Jessica J. HoSo let's start with proposition A. Very simply put, this is an earthquake safety and emergency response bond measure, and it would authorize the city to borrow money for various emergency preparedness and infrastructure projects throughout San Francisco. Um bond financing is something that the city uses to finance capital projects such as fire and police stations, affordable housing programs. The city receives the money by selling bonds to investors, and eventually the city pays them back for the original amount plus interest.
Ryan BlakeUm, so these bonds are part of our method of financing capital enhancements in San Francisco. So and other municipalities do the same thing. So if you need money up front for something, you issue a bond, you collect the money, and you build what needs to be built, uh, whether that's a new hospital, a seawall, a park, you issue the bonds and get that money. So then the bonds are usually repaid over 30 years. And the when the bonds that we passed 30 years ago finish, we reissue a bond package for the next 30 years. So that's without an increase to new taxes that you'll see in a lot of the language of these bonds. Um, and there's a whole schedule of which cause the bonds will be spent on in future years. So yeah, so this year it's emergency response preparedness. There's a whole schedule for things like parks and open spaces, public health, earthquake safety in the future.
Jessica J. HoThis measure requires 66 and two-thirds percent affirmative votes to pass. Um, and how it got on the ballot is that on February 3rd, the Board of Supervisors voted 11 to 0 to place Prop A on the ballot.
Ryan BlakeYeah, so the current funding breakdown on proposition A is the committee in support has raised $1.9 million, and there's no committee opposing it at this time. So um, but if you look at the supporters of the bond this year, it is a purely unified front. You have Mayor Lurie, every single member of the Board of Supervisors, Nancy Pelosi, the San Francisco delegation from the state legislature, uh Democratic Club, Sierra Club, League of Pissed Off Voters. It really spans the entire spectrum, except for that conservative piece of the pie in San Francisco, which is notable. San Francisco does have a population of registered Republican voters, um, but it is um a very small portion comparatively. So the the opposition argument in your voter information pamphlet is written by the San Francisco Republican Party. Um and the San Francisco Republican Party writes ballot arguments every election cycle. They're almost always the opponents of these bonds or parcel taxes that San Francisco passes on a regular cadence.
Jessica J. HoAnd since this is a sense of connection, I do think it's worth noting that even though there is no formal committee registered to oppose Prop A, several Sunset residents have submitted paid ballot arguments against the measure. I think it's interesting because it reflects something broader about Sunset politics. Even when there's broad agreement around certain things like earthquake preparedness throughout the city, there's can still be skepticism around government spending, accountability, and implementation. And honestly, one thing I think that struck me reading this section is that people were not really debating earthquakes because we all know the big one is coming, but they're debating whether they feel like there's enough transparency around how the bond money is prioritized or spent. And some questioned whether all the projects are truly emergency related. So if you live in the Sunset or West Side neighborhoods, it may be interesting to read some of those arguments directly and think through why some Sunset residents remain cautious, even on measures that otherwise appear widely supported. While Prop A is mostly about infrastructure and emergency preparedness, Prop B shifts into a very different debate: political power, institutional memory, and how much turnover voters want in city
Prop B And The Term Limit Fight
Jessica J. Hogovernment. Moving on to proposition B. This measure would change San Francisco's current term limit rules for the mayor and board of supervisors so that they can no longer serve two consecutive terms, sit out for an undetermined period of time, and run again later. I was very surprised that this ballot measure got on the on the ballot because of a vote by the Board of Supervisors themselves. So it was actually introduced by the Board of Supervisors, and seven of the members voted yes, while four voted no. And this measure will require 50% plus one affirmative votes to pass.
Ryan BlakeUm a quick overview of the funding that is that there's been $358,000 in support for this measure and $18,000 in opposition. So it's pretty overwhelmingly been funded in support.
Jessica J. HoOne thing that's surprised me is that the people who support or oppose this proposition don't typically align on the same ideological sides. And uh famously, Supervisor Aaron Peskin and Mayor Willie Brown did not get along. Correct. In fact, they were mostly opposed to each other's ideas for the majority of their tenure, and yet they are both opposed to this ballot measure. Um, do you think that is normal, Ryan?
Ryan BlakeUm, in San Francisco, I'd say nothing's ever normal. But um, yes, sometimes it's surprising seeing who endorsed who or which initiative. Um, I would say that relationships and timing are very key. Um, San Francisco often uses these imperfect designations of progressive versus moderate, and Prop B is the kind of measure that shows there's nuance to it. Um, in support, you have Mayor Lurie, Assemblymember Haney, State Senator Scott Wiener, and six of the members of the Board of Supervisors. Um, it's worth noting, in my opinion, that none of the current supervisors signed on to a ballot argument against Prop B, although we did have two of our former mayors, uh Art Agnos and Willie Brown, authored a paid ballot argument against that. But in opposition, you have some of the more progressive camps, but it's not a one-to-one match. You see relationships pull a few of the would-be supporters over to the opposition side.
Jessica J. HoI thought it was interesting that uh the argument for Prop B had to do with allowing newer people, newer voices to participate, whereas the rebuttal to the proponent's arguments say that this is a solution in search of a problem, that the current system as it is, even with the loophole, or doesn't actually prevent change. Another argument from the opponent side is that this limits democracy because if the voters really like someone, they might want to vote this person back in after four years. So what are your kind of thoughts on each of the uh arguments for and against?
Ryan BlakeYeah, I think I think it's it's really effective to use people call it the Peskin loophole, to use the Aaron Peskin situation as a case study for this. So former Supervisor Peskin served on the Board of Supervisors from 2001 to 2009. Then after David Shu was elected to the assembly, then Mayor Ed Lee appointed Julie Christensen and Peskin challenged her, which was in 2015. So he won in 2015 for a partial term and then was elected to a full term in 2016 and re-elected again in 2020. So all said and done, Aaron Peskin served for over 17 years on the Board of Supervisors in San Francisco. And it's also worth noting that he outpaced his colleagues in volume of legislation passed every year. Um and if you use this as a case study, either you see someone who was a, if you're a fan of them, they were a long-serving champion that left this undeniable imprint on San Francisco. If you didn't like Aaron Peskin, he was this unmovable opponent for nearly 20 years. Um, but speaking to what it actually does, I I think there is merit to both sides of this. We see, I think, a national sentiment, uh, especially amongst young younger voters and millennials, if we can call ourselves young still, uh, for younger representation in government. And with historic legacies, also comes elected officials who have been in power for decades sometimes. So now, with that experience, on the other side, comes seasoned political operatives that can often get things done more efficiently, faster, at a higher rate of success than, say, a freshman lawmaker could. So, does not allowing a termed-out supervisor to run for a third or fourth term after taking four years off mean that our board of supervisors will have this upswell of younger people being elected to it? Maybe. But it's not an exact science.
Jessica J. HoNow
Prop C Versus Prop D Explained
Jessica J. Howe move into what is probably the most ideologically and economically charged part of the ballot, and probably the section with the biggest implications for San Francisco's economic future. Now we're moving on to prop C and D. And even though you mentioned we only have four this cycle on the June 2nd ballot, actually Prop C and Prop D are related. So starting with Prop C, Prop C would make this the existing executive pay ratio less aggressive in several ways. It would raise the exemption threshold from 5 million to 7.5 million, meaning fewer businesses would be affected overall. And in fact, this will actually decrease the city budget by $30 to $40 million. And supporters argue that San Francisco's economy remains fragile and this is not the moment to dramatically increase business taxes. But opponents argue that proposition C would reduce city revenues, which it will at a time when San Francisco is already facing serious budget pressures. And then Prop D is effectively the competing measure, but it moves in the opposite direction. So the Prop D would substantially increase the tax rates on companies by eight times with executive to worker pay gaps. It would lower the thresholds because instead of having the highest paid executive and median worker pay be based on San Francisco workers, it would be based on all workers, which means that it would be, it would basically increase the net of or companies that would qualify for this tax. And it would also accelerate the timeline where higher tax rates take effect. And critics of this measure have described that multiplying these rates would make it more difficult for companies to operate and thrive in San Francisco, whereas supporters also argue that San Francisco cannot continue cutting services while wealth concentration keeps increasing at the top. Both of these propositions need 50% plus one to pass, and they were both put on the ballot by signature gathering effort. So both of these were not put onto the ballot by the board as supervisors. Um and interestingly, Prop D was put on the ballot on February 10th, 2026, and uh proposition D was put on the ballot like one day after. It is a little confusing, a little misleading, right? It's I mean it's it's we need to cut through some of that jargon sometimes to really understand what's going on. And for people who have been listening to any of the arguments in through their mail or through just the radio or whatever you get your information, you might have heard about property as a CEO tax, but in fact, it's not a tax on the CEOs, but a tax on the businesses.
Ryan BlakeSo I I do think that it is worth noting that local governments cannot impose income taxes. The state government and the federal government are have the ability to do that. But San Francisco cannot tax the incomes of individuals. So this is introduced as a CEO tax, but it uses the gross receipts mechanism on companies that have this disparity of average wages between that C-suite executive and the average global employee. Um, so I just think that's an important distinction to make.
Jessica J. HoSo with that being said, Ryan, break it down for us.
Ryan BlakeAll right. You have two camps here. You have the proponents of proposition D. They were the ones that came first with their idea, and that is mainly funded by labor entities. They've raised about 2 million. The response to that was more from the business community, and that um is saying yes on prop C, which is their alternative, and no on D at the same time. And that has raised about $5.1 million.
Jessica J. HoI also think just to mention what's really interesting is that if Prop D passes with more votes than Prop C, Prop C would have no legal effect. So that means that if Prop D, Prop C and Prop D both get 50 plus one, but Prop D gets more votes, then Prop C would actually lose still. So they're in effect competing measures.
Ryan BlakeYeah, yeah, it's a common strategy. I think we're seeing a few different common strategies when it comes to ballot initiatives at play here. Um, the the first one being is is ideally you keep something off the ballot if you don't like it. You can negotiate, you can come to a compromise. Um, if that doesn't work, a lot of the time you will see the strategy of someone putting their own similarly worded or just kind of within the same scope. And ultimately voters kind of have to choose between two things that now sound somewhat similar. Um and that's one of the ways to to pursue defeating something if you uh aren't able to negotiate keeping it off the ballot, or there's a potential that it's not viable to defeat it outright.
Jessica J. HoUh
Business Taxes And The Risk Of Flight
Jessica J. Hodo we have a sense of which companies may leave if this proposition D were to pass?
Ryan BlakeSo um if I can really quickly go back in time just a little bit. Uh San Francisco used to have a payroll tax for companies that just bit did business in San Francisco. So this was seen as a job killer. And in 2012, we moved to this gross receipts tax mechanism. It's known as GRT for short. Um, they did that to spur economic job creation because it taxed receipts and scales up the more a company makes, so it felt more equitable. Um, since that passed, San Francisco then tacked on multiple additional GRTs. Uh, this effectively doubled the tax obligation of doing business in the city. Um, in addition to it being more costly, it was incredibly complicated. So in 2024, stakeholders came together and mostly everybody was able to get aligned on a full overhaul of our business tax system. It simplified the amount of categories businesses were classified as, which are called NACE codes and A I C S, and consolidated some of the existing business taxes. San Francisco was also still struggling to rebound from the pandemic. So it was initially aimed to be revenue neutral, but in the end, it was around a $40 million annual total tax decrease. So that effort was supported across the board. Then mayor London Breed, then candidate now mayor Daniel Lurie were both in support of it. The then board Aaron Peskin board president Aaron Peskin, uh, supervisors Mandelman, Stephanie Melgar, Chan, the business community. There was no paid argument against the overhaul from 2024. So, and I think some of the displeasure with proposition D and Proposition C is that we all came together and we agreed that this was what was needed to help us get out of that hole that the pandemic put us in. And less than one year later, people were introducing things to start collecting signatures to change the tax code again. And that unpredictability and complexity is just as frustrating at times as the actual incurred cost of the tax and and having to forecast what is doing business in San Francisco gonna look like a year from now, and having no idea what the actual answer to that is when you're making big decisions on do you come to San Francisco or if you already are in San Francisco, do you want to go to Oakland or do you want to go down the peninsula or the business parks in San Ramon, which was there, there was a historic exodus when that was first built in the late 80s and 90s of companies doing that exact thing. You kind of can apply that same reasoning to um what companies could potentially leave today, whether it's the gross receipts or it's the job creation or the um offices that they're leasing downtown. Um, there is a cascading effect when companies are leaving San Francisco. And um as much as we enjoy the great services in San Francisco, um, the a lot of the services that we are able to provide are paid for by the industries that choose to be here.
Jessica J. HoOne
Downtown Recovery And Budget Stakes
Jessica J. Hothing that I think um is really interesting that I have experienced in my personal life or my professional life lately is I'm helping um one of my clients is trying to look for office space in Union Square. And I did not realize how many spaces were still vacant in the Union Square downtown area. Um, and so that is something like in 2026 is still an issue, even though the pandemic happened a long time ago, right? In 2020, six years ago. And I think there are multiple factors that impact that, including the rise of e-commerce, which we always knew was going to impact the amount of spice space or retail space that was necessary compared to before the internet was invented. Um, but there's also a lot of these return to work types of uh policies that may or may not be working to revitalize downtown. So that in addition to the CEO attacks are compounding issues too that I think need to be considered when trying to think about the situation as a whole. I think it's interesting too because the proponents of property are really using the argument that it will save vital vital city services because of the city budget deficit that we're experiencing and that it will potentially save public hospitals, mental health services, homelessness resources, fire safety and first response, caregivers for seniors. But the language of the proposition has nothing to do with those topics. It has just to do with increasing the tax on certain businesses.
Ryan BlakeYeah, I mean, San Francisco has the biggest budget per capita of any city, any city and county, because it is only city and county in California. But but if you compare it to other municipalities, we have way more per constituent. And what that results in a lot of the time, when you align that also with the liberal ideals of San Francisco as a city, is a lot of crucial services that help some of the most vulnerable people. And so when you have that large budget and this measure will contribute to it, you know, at there is a question. Correlation to those types of services that are being provided to the people of San Francisco. Um so so when you're making the case for why people should vote for this tax increase, uh it's a natural um point to be drawn to to make the case to persuade voters.
Jessica J. HoAnd as we all know, San Francisco is facing a pretty severe budget shortfall. Um and so I'm curious why the mayor is supporting props, which actually reduces the amount of funding for the general fund.
Ryan BlakeWell, I can't speak for the mayor, but um I I think that there's a few different schools of thought right now in San Francisco that San Francisco's downtown is still suffering, and and I think there's data behind that. I don't I don't think that's uh too much of the of someone's opinion. Um San Francisco downtown still needs a lot more help to get back to where it was before. The neighborhoods are thriving. Um but but in order to do that, there's a lot that could still be done. And so there's perspectives that if you make it easier for businesses and in the short term, maybe the price there's a price tag associated with it that you'll you won't collect as much money, um, but more businesses come in, your total net gain is still going to be positive. And so um, as I said in some of the earlier ballot measures, it's not an exact science. So it really depends who you ask. Some people think we should increase the taxes because it'll generate more taxes. People would counter that and say people will leave, and then they say we should do tax breaks and it will bring more people, and then more people will be paying those reduced taxes, and in the end we'll have more money. So um, you can find an economist that'll tell you both of those are sound cases. Um, it's really just um a matter of you know which perspective you believe in more at the end of the day.
Final Takeaways Before You Vote
Jessica J. HoThanks so much, Ryan, for joining me today.
Ryan BlakeIt was my pleasure. Thank you for having me.
Jessica J. HoA lot of things to think about. But hopefully um this episode has helped you understand what's going to be on the June 2nd ballot in terms of ballot measures so that you can make your own informed decisions before election day. Thanks again to Ryan Blake for joining me today and helping me break down these issues. I'm Jessica Ho, and thank you all for listening to the Sunset Connection. See you around in the neighborhood.
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