What Two New American Mayors Reveal About The Current State of Brand Transformation
An Unusual Case Study
Last week, my feed was wall-to-wall Mamdani. I don’t live in New York, and I’m not really interested in politics. But for some reason, I started to look more closely at what Mayor Carhartt was doing.
This also led me to examine how Daniel Lurie was approaching his new job as mayor of San Francisco. A study in different styles and political ideas, for sure. But the brand nerd in me was excited.
This article talks about what I learned from these two men about the current state of brand transformation.
Two Newbies
New York’s Zohran Mamdani was only sworn in on January 1, but he’s been dominating the zeitgeist for much of the last 12 months. Last week he showed up to make a speech in a snowstorm in a custom Carhartt jacket with a 1970s slogan embroidered in a vintage typeface.
Mayor Lurie has been in his job for 12 months longer. And he’s similarly been making headlines. As Mr. Mamdani was drawing a red line for NY’s slumlords, Lurie announced that he’d hired Jony Ive to rebrand his city.
Both statements piqued my professional curiosity.
These two decisions—the choice of jacket and the choice of designer—weren’t merely stylistic or aesthetic. They were declarations of strategic intent. They told us who each mayor is standing by and standing up for.
What they revealed isn’t a framework about aspiration versus capability. It’s something harder to learn and more uncomfortable for many brand owners to face: What total commitment actually looks like when you declare who you’re fighting for.
Over my career I’ve seen many brand leaders present customer-centric brand transformation plans, get board approval, and then systematically optimize for investor metrics instead.
I used to think this was strategic cowardice. I was wrong.
It’s structural: boards haven’t quite learned what Lurie and Mamdani already know about stakeholder commitment. And until they do, CMOs and CBOs will keep hedging—not because they lack conviction, but because their boards measure the wrong things and provide air cover for nothing.
The Question Most Brand Leaders Won’t Answer (Truthfully or Publicly)
Who are you fighting for?
Not, “who do you serve? Not, “who are your stakeholders?” These questions let you say “everyone” and feel virtuous about it.
Who are you fighting for? As in, whose approval do you need for this transformation to succeed?
Lurie’s answer is unambiguous: business leaders and capital providers. His success requires their confidence in returning to San Francisco. If tech workers don’t come back, if investment doesn’t flow, if corporations don’t reopen offices—his theory of transformation fails, regardless of how many services improve for existing residents.
“I’m calling companies around this country and saying, ‘What can we do to get you back here?’” That’s not rhetoric. That’s strategy. Capital first. Services follow.
Mamdani’s answer is equally clear: tenants and working-class residents. His success requires their political activation. His theory fails if they can't organize to get the heat turned on, hold slumlords accountable, or build enough power to move resources, no matter how much business leaders agree.
His first official visit after he took office? A rent-stabilized building in Flatbush where tenants had no heat in January. “Today is inauguration day. It is also the day that the rent is due.” That’s not symbolism. That’s strategy. Residents first. Power follows.
Neither mayor is pretending to fight for everyone. Both know that “we’re fighting for everyone” is how you end up fighting for no one effectively.
Here’s what I think makes both mayors remarkable: every choice they’ve made since Day One actively reinforces who they’re fighting for, with zero hedging.
Day One as the Total Commitment Test
Remember what Lurie did on Day One—not what he said, but what he did:
Before dawn: Walked the Tenderloin with the police chief. Not a photo op—an actual working tour of the neighborhood where people are dying from fentanyl overdoses. The message: safety first, because capital won’t return to a city that feels dangerous.
Inauguration: Civic Center Plaza, outdoors, 2,600 people, Steve Kerr opening remarks, cable car ride through the city. Ceremonial optimism designed to signal San Francisco is open for business again. The message: global stage, we’re back.
First cabinet appointment: Staci Slaughter from the SF Giants—someone who knows how to work with wealthy stakeholders and run complex operations for elite audiences.
Policy sequence: Fentanyl emergency (Day 1) → hospitality task force (Week 4) → business permit reform (Week 5) → CEO partnership launch (Week 10).
Ten weeks later: Partnership for SF announcement with 38 CEOs backing transformation initiatives. Then the Jony Ive reveal—months of secret meetings to rebrand San Francisco with the world’s most expensive designer.
Every single choice reinforces the same stakeholder: capital providers, business leaders, and investors. Not “also residents” or “everyone benefits eventually.” Capital first. Everything aligned to earn their confidence.
Now watch what Mamdani did:
Midnight, Day One: Sworn in at a decommissioned subway station by New York’s attorney general, using his grandfather’s Quran. You have to descend into the city’s infrastructure to watch him take power. The message: transformation happens underground, through the machinery most people never see.
First official visit: Rent-stabilized building in Flatbush with notorious slumlord, tenants without heat in January. The message: you matter first, not business leaders.
First appointment: Mike Flynn as DOT Commissioner, announced at 12:01 AM. Not after business roundtables. Not after investor briefings. Transportation infrastructure first, because it determines who can access opportunity.
First week: 12 executive orders focused on tenant protection. First new position created: Deputy Mayor for Economic Justice. Not “Economic Development.” Economic Justice.
First major event he skipped: Real Estate Board of New York annual gala. REBNY president complained publicly: “The fact that our mayor is not going to be here tonight is wrong.” Mamdani’s absence wasn’t an oversight. It was a declaration: I’m not seeking your approval.
Ten weeks later: The Office of Mass Engagement launches, staffed by the organizers who knocked on 3 million doors. Rental Ripoff hearings begin, organizing tenant political power building by building.
Every single choice reinforces the same stakeholder: tenants, working-class residents, and the people who keep the city running. Not “eventually business leaders benefit too.” Residents first. Everything aligned to build their political power.
This is the discipline most brand leaders lack: total alignment to a chosen stakeholder with zero hedging.
Both mayors know something most leaders don’t want to accept:
Stakeholders can tell when you’re hedging. And when they sense hedging, they withdraw the support your transformation requires.
If Lurie tried to organize tenant political power while courting CEOs, business leaders would sense the mixed signals and withhold investment. If Mamdani tried to court real estate developers while organizing tenants, residents would sense betrayal and withhold political activation.
You can’t fight for both simultaneously and maintain the trust of either.
The Five Tests That Reveal Who You’re Really Fighting For
Lurie and Mamdani have the discipline to align rhetoric with resource allocation. You can watch their choices and know exactly who they stand by.
Five tests reveal whose approval you actually need, regardless of what your transformation deck claims:
1. First Hire Test: Does this hire help you serve your chosen stakeholder?
Lurie hired Staci Slaughter—someone who works with wealthy stakeholders and runs complex elite operations. If you’re fighting for capital confidence, you need someone who speaks that language.
Mamdani hired Mike Flynn for DOT at 12:01 AM—before any business roundtables. If you’re fighting for working-class residents, you start with infrastructure that determines who can access opportunity.
Your answer: Did you hire a chief brand officer before a head of customer success? A creative director before a chief operating officer focused on outcome delivery?
The first hire reveals whose needs you’re actually prioritizing, regardless of what you told the board.
2. Budget Test: Does this spending serve your chosen stakeholder?
Lurie spent big hiring Jony Ive and his all-star design team, Partnership for SF CEO convenings, and elite brand consultants. If you’re fighting for capital attraction, you invest in aspiration architecture that makes the city compelling to investors.
Mamdani invested in The Office of Mass Engagement, Rental Ripoff hearings, and organizing capacity in every borough. If you’re fighting for resident political power, you invest in capability infrastructure that makes tenants able to demand accountability.
Your answer: Did you spend more on agencies, rebranding, and creative production than on customer research infrastructure, capability-building tools, and outcome measurement systems?
The money reveals whose outcomes you’re actually optimizing for.
3. Stakeholder Sequence Test: Did you brief your chosen stakeholder FIRST?
Lurie’s first strategic briefing went to 38 CEOs. His transformation requires their confidence before anything else works.
Mamdani’s first visit was to tenants without heat. His transformation requires their political activation before anything else works.
Your answer: Did the board, investors, or analysts get your first transformation presentation? Or did frontline employees, customers, or the people your brand affects most go first?
The sequence reveals who needs to believe in this for it to work—and therefore whose trust is non-negotiable.
4. Metrics Test: Do these measure value creation for your chosen stakeholder?
Lurie measures capital attraction: approval ratings among business leaders, investment flow, tech worker return rates, and business confidence indices.
Mamdani measures capability delivery: heat turned on, evictions prevented, tenant organizing capacity built, and political power indicators.
Your answer: Are you measuring brand awareness, consideration, preference, or NPS? Those measure value for capital providers (they want to know you’re building brand equity).
Or are you measuring capability utilization frequency, outcome achievement rates, switching costs, and relationship longevity? Those measure value for customers (they want to know you’re helping them accomplish goals).
Both metric sets are valid. They just reveal different stakeholders.
5. Failure Mode Test: When this fails, will it be because you didn’t serve your stakeholder well enough—or because you tried to serve everyone?
If Lurie fails, the post-mortem will say, “Beautiful rebrand, elite partnerships, capital flowing to luxury developments, but Tenderloin residents are still dying. Failed to translate capital attraction into service delivery fast enough.”
That’s a failure of execution within his chosen strategy, not a failure because he chose wrong.
If Mamdani fails, the post-mortem will say, “Impressive organizing, tenant mobilization, and democratic engagement, but couldn’t deliver heat and housing fast enough. Failed to convert political power into resource delivery.”
That’s a failure of execution within his chosen strategy.
Your answer: Write your transformation’s failure post-mortem now. Does it say “great brand work that didn’t move business metrics” or “great capability work that couldn’t scale”?
Or does it say something like, “tried do both aspiration architecture and capability delivery, confused everyone about priorities, built neither effectively”?
That’s hedging failure. And it’s the most common failure mode.
You can’t fight for both simultaneously and maintain the trust of either.
Three Brands That Prove The Value Of Total Commitment
These aren’t theoretical tests. Three brands in the last three years have shown what happens when boards give their brand leaders the air cover to commit completely—and the results are measurable enough to change the board conversation.
GM Super Cruise: The Patience Play
What they committed to: Making hands-free driving indispensable over rushing features to market for competitive optics.
What it cost: Mapping 750,000+ highway miles before launch. Slower rollout than competitors who shipped faster with less capability. Years of investor pressure asking why they weren’t moving faster. The discipline to keep expanding capability rather than cutting corners for quarterly wins.
What it proved: Renewal rates climbed from 2% in early trials to 40% as customers experienced the capability over time. That’s not aspiration—that’s dependency formation you can measure. 625,000+ active subscribers. 700 million+ hands-free miles driven with zero crashes attributed to the system. $234 million in revenue in 2025, with $400 million projected for 2026.
CEO Mary Barra stated the strategy explicitly: “Our customer-focused strategy with Super Cruise is to continuously refine and expand its capabilities to make it indispensable.”
Why boards should care: Dependency formation follows a curve. The metric isn’t awareness or consideration—it’s “do customers renew when the free trial ends?” That’s a number you can defend in any board meeting. GM’s board provided air cover for the patient build. The renewal rate proves they were right.
Hopper Travel: The Counterintuitive Trust Build
What they committed to: Building customer reliance on predictive intelligence over maximizing immediate conversion rates.
What it cost: Their app told 70% of users to wait rather than buy immediately—leaving short-term revenue on the table every single day to build long-term credibility. Every e-commerce playbook says “convert now.” Hopper’s strategy says, “earn trust by telling customers when NOT to buy.” That’s terrifying to explain to a board focused on quarterly bookings.
What it proved: Push notifications convert 3x higher than when customers initiate searches themselves. 25% of tickets sold are for trips the user didn’t originally search for—the AI recommended them and customers trusted the recommendation. $7.5 billion in gross bookings in 2024. Over 60% of users are purchasing protection products (Price Freeze, Cancel for Any Reason) because the trust relationship supports it.
The system processes 300 billion flight prices monthly with 95% accuracy up to one year out. But the strategic insight isn’t the prediction accuracy—it’s the willingness to tell customers “don’t buy yet” when that’s the right answer.
Why boards should care: Trust converts higher than urgency when you’re building longitudinal relationships. Hopper’s board had to believe that telling customers NOT to buy would eventually generate more revenue than conversion optimization. The 3x lift on AI-initiated recommendations proves they were right.
Morgan Stanley: The Proprietary Moat Build
What they committed to: Eliminating friction between advisor knowledge and client communication over implementing flashy consumer-facing chatbots.
What it cost: Building a custom system trained on 100,000+ proprietary research reports rather than using off-the-shelf solutions. Integration into advisor workflow instead of launching consumer apps that generate press coverage. Making the technology invisible to clients—they experience better advisor conversations, not “AI innovation.” That’s hard to explain in investor presentations where everyone wants to see customer-facing AI.
What it proved: 98% adoption among roughly 16,000-20,000 advisor teams. Document retrieval efficiency jumped from 20% to 80%. The firm reported a record $64 billion in net new assets in Q3 2024, with executives directly attributing gains to AI-enabled efficiency.
Jeff McMillan, Head of Firmwide AI: “Now, advisors can engage clients on topics they haven’t discussed before because the friction between knowledge and communication has gone to zero.”
Why boards should care: The switching cost is structural. Advisors leaving Morgan Stanley lose access to an institutional knowledge layer trained on decades of proprietary data that cannot be replicated elsewhere. That’s a moat you can measure. Morgan Stanley’s board invested in capability infrastructure rather than marketing innovation. The adoption rate and asset flow prove they were right.
Brand leaders optimize for what boards measure, and boards measure what keeps analysts happy, and no one builds anything defensible.
What Real Commitment Costs—And Why Boards Should Pay It
Both mayors are making enemies. Real enemies who are actively working against them. And both accept this as the cost of commitment.
Lurie’s costs:
London Breed, the outgoing mayor he defeated, said something that reveals the resentment his strategy creates: “It is easy to attach a white face to the work that a Black person has done.”
Lurie is getting credit for San Francisco’s recovery that he didn’t build. Breed and her team spent years addressing fentanyl, homelessness, and crime while facing brutal criticism. Now that recovery is visible, Lurie’s aspiration architecture—the Jony Ive rebrand, the global media—means he’s getting the credit.
The people who actually did the work resent him. Community organizers who spent years in the Tenderloin see an elite mayor hiring elite designers to brand their neighborhood’s pain. That resentment is real, justified, and growing.
But Lurie’s transformation theory requires capital confidence more than community organizer approval. So he accepts the cost.
Mamdani’s costs:
Real estate developers, business leaders, and capital providers are openly hostile. REBNY’s public complaint about him skipping their gala was just the opening shot. As Rental Ripoff hearings organize tenants to demand accountability, landlords are positioning Mamdani as “anti-business” and “hostile to growth.”
The business press questions whether he can govern effectively without capital support. Developers are threatening to slow new construction. Some business leaders are calling for state intervention to limit mayoral power.
That hostility is real, sustained, and expensive in political capital.
But Mamdani’s transformation theory requires tenant political power more than business leader approval. So he accepts the cost.
Most brand leaders can’t accept these costs because their boards won’t provide air cover.
CMOs and CBOs want customers AND investors to be happy. Employees AND the board to approve. Brand perception AND capability delivery. Capital attraction AND democratic organizing.
They want everyone to like them. They want every stakeholder group to feel prioritized. They want to avoid the resentment that comes from choosing.
But “everyone likes us” is not a strategy. It’s a failure to commit.
And stakeholders—all of them—can sense when you’re trying to please everyone. They sense hedging. And they withhold the support your transformation requires because they don’t believe you’ll actually prioritize their needs when conflicts arise.
Because conflicts always arise. Capital wants different things than customers. Investors want different timelines than employees. Short-term revenue wants different investments than long-term capability building.
When those conflicts emerge—and they will—whose approval do you actually need?
If you haven’t decided, you’ll make the politically safe choice that pleases no one and builds nothing.
If you have decided, you’ll make the hard choice, accept the costs, and build the stakeholder support that matters for your transformation theory.
But you can only make that choice if your board provides the air cover that makes total commitment possible.
Boards exist to protect leadership from short-term pressures that undermine long-term value creation. Somewhere along the way, they stopped doing that job.
What Brand Owners Can Learn From Two Young Mayors
Lurie and Mamdani don’t have boards of directors. They have voters. Every choice—Jony Ive, Carhartt jacket, skipping the REBNY gala—is a personal bet. If their strategy fails, they’re done. No quarterly earnings call to smooth things over. Just political death.
That terror forces clarity.
Most brand leaders have boards. Which should be an advantage—a group of experienced leaders who can provide air cover while single-minded strategies pay off. Boards exist precisely to protect executive leadership from short-term pressures that undermine long-term value creation.
But somewhere along the way, boards stopped asking, “Are we committed to the right stakeholder?” and started asking, “Why did brand perception only improve 2 points?”
The result: CMOs and CBOs optimize for what boards measure, and boards measure what keeps analysts happy, and no one builds anything defensible.
Until recently, there wasn’t enough evidence to make a different case. Now there is.
GM’s renewal rates went from 2% to 40% as customers experienced Super Cruise—that’s measurable dependency formation. Hopper’s counterintuitive “wait to buy” approach converts 3x higher than customer-initiated searches—that’s quantifiable trust. Morgan Stanley’s 98% adoption directly contributed to $64 billion in net new assets—that’s ROI you can defend to any board.
Commitment to a chosen stakeholder, with total operational alignment, creates a competitive advantage you can measure.
The question isn’t whether commitment matters anymore. The evidence proves it does.
The question is whether boards will provide the air cover that makes commitment possible—and whether CMOs will make the case that justifies it.
Lurie and Mamdani have 18 months to prove their theories. They’re risking everything personally.
You probably have less time. But unlike mayors, you have a board who can say, “Yes, we’re redirecting the brand budget to capability infrastructure in Q2. Here’s why that’s the right long-term bet,” or “Yes, investors will be less impressed in the short term. We’re building customer dependency through outcome delivery, and here’s the evidence that pays off.”
These two mayors show what happens when a brand leader goes all in. The case studies show what happens to CLTV when brand owners are clear who they’re fighting for.
Lurie and Mamdani are twelve months into their bold experiments that will either prove or destroy their theories of transformation. The brands profiled above are three to five years in, with encouraging results.
The evidence is accumulating faster than boards are learning from it. GM took five years to move renewal rates from 2% to 40%. Morgan Stanley took three years to reach 98% adoption. Hopper spent years building the trust infrastructure that now converts 3x higher.
Most brand leaders don’t get five years. Most don’t get three. Or two. Or one. The boards who figure out how to provide air cover for their commitment are the ones who’ll have defensible positions when their competitors and investors wake up.
Lurie and Mamdani will know in eighteen months whether their theories worked. Your board shouldn’t wait that long.