“Athena and Jazz” - it’s an odd name. ChatGPT loved it. Claude… not so much.
“I’ll be straight with you: ‘Athena and Jazz’ is poetic and has nice symbolism—wisdom meets improvisation—but it’s pretty abstract for a build-in-public newsletter.” —Claude
Then I explained.
“Okay, I take it back. With that context, it’s actually brilliant.” —Claude, reconsidering (I tune my AI for candor—not compliments).
Rewinding a bit.
I built my career in the thick of “war mode” tech culture. War rooms. Hustle. Unattainable targets framed as ambition. Leadership defined by speed and force.
Then the cracks became impossible to ignore. WeWork’s spectacular collapse became the cautionary tale—SoftBank’s Vision Fund war chest fueling blitzscale narratives that imploded. I saw similar dynamics firsthand at Fair, a SoftBank-backed car subscription startup where I led product through a SoftBank‑backed $385 million Series B, with headlines touting over a billion in secured debt.
For a few surreal days, I was part of a self-selected tiger team, rallying around an ambitious launch tied to our Uber partnership and SoftBank’s aggressive targets. The VP of Engineering and I did our best to shield the team from impossible requests while still leaning into our own ambitions. We made it clear: “Who wants to sign up for this mission?” The CEO promised full support: “I’ll do whatever it takes to help you hit this target—including putting you in a mansion, feeding you, getting you massages.”
That’s how I ended up in the infamous FairBnb—a mansion in Brentwood, sprinting alongside some of the most talented engineers I’ve had the privilege of working with plus a brilliant designer. Strategy sessions over frittatas. Late-night debates. Product decisions on the fly. I might have laughed or cried at how it felt like living inside an episode of Silicon Valley—exhilarating, absurd, and ultimately unsustainable.
That sprint became a preview of what would follow. Despite incredible talent and huge capital backing, Fair would later face its own reckoning. Leadership turned over, the company went through a brutal 40% RIF, and the ambitious promises made to the market collided with the operational and cultural cracks beneath.
Those moments made something clear: ambition without wisdom burns out people and products alike.
Why Athena.
That’s why Athena resonates. Athena, goddess of wisdom, war, and strategy, was always more than just a fighter. She represented skill over savagery, intelligence over impulse, and purposeful ambition over reckless conquest.
After the era of war rooms came the inevitable overcorrection—peace rooms, culture decks preaching balance, and sanitized language that sometimes felt disconnected from the reality of building ambitious products.
Don’t get me wrong: peace has its place. I’ve seen firsthand how toxic overwork and hyper-aggression can grind teams down.
I’ve cried in a bathroom stall, breaking down from the stress.
One day, after spending hours on a car lot in the rain—galoshes on, trench coat soaked, taking pictures of VINs and running in and out of a trailer where engineers were debugging a hastily-built fleet management system—I came home and took a call outside.
I ended up standing in the rain again, getting yelled at by one executive after a major launch, while another executive was texting me in real time:
“You don’t need to listen to that,” they said. “He’s just stressed and feeling defensive.”
I texted back: “I’ll hear him out for now.” I should have hung up.
I’ve lived these dynamics and seen how they ripple through teams, corroding both people and products.
But I’ve also operated in teams that went too far the other way—where “nice” culture veered into what Kim Scott calls ruinous empathy. Where tough decisions were avoided, standards slipped, and progress stalled under the weight of politeness and conflict avoidance.
Peace alone isn’t the answer. Neither is unchecked war-mode.
This isn’t about rejecting ambition—it’s about redefining it.
Ares, the god of war, represents brute force—violence, chaos, aggression for its own sake. Athena is different: she embodies strategy, wisdom, and purposeful conflict. Not war for war’s sake, but battle in service of something greater.
I’m not here to abandon ambition. I’m here to reclaim it—with a feminine edge, with strategy at the core, with humanity alongside momentum.
We need ambitious leaders willing to take on hard, meaningful challenges—to stretch beyond the easy path, to build technology that actually improves lives. But we need to pursue that with wisdom, strategy, and humanity—not force, fear, or performative hustle.
Athena is the model: ambition sharpened by clarity, strategy balanced with empathy, momentum driven by purpose—not pressure. Not aggression for aggression’s sake, but decisive, thoughtful action aimed at building things that last and matter.
Why Jazz.
And then there’s Jazz.
If Athena grounds me in strategy, Jazz reminds me to stay flexible, curious, and responsive.
Modern product building—especially in AI—is messy and improvisational by default. Roadmaps shift. Data is incomplete. Users don’t behave how we expect. Markets turn mid-flight. I’ve seen it across early-stage startups and corporate teams: the leaders who thrive are the ones who can riff in real time, course-correct without ego, and find rhythm inside uncertainty.
Miles Davis captured it perfectly:
“It’s not the note you play that’s the wrong note—it’s the note you play afterwards that makes it right or wrong.”
In AI product work, we’re often writing the score as we go. Jazz is a leadership mindset—treating product work as conversation, not control, turning missteps into momentum, and staying creatively engaged even when the path isn’t obvious.
I see it already in how we think about roadmaps. After spending a few weeks in an AI coding bootcamp, I watched people build near-production-ready clones of Calendly and Trello—in a week.
The way we scope work isn’t just evolving—it’s collapsing and reforming in real time. Timelines we once treated as natural laws are evaporating into weeks, sometimes days. Definition and delivery are no longer distinct phases—they’re blurring, overlapping, feeding each other in unpredictable loops.
Our mammalian brains are about to get scrambled. We’re wired for linear progressions, for steady cycles of plan → build → ship. What’s coming is faster, messier, and profoundly destabilizing. Some teams will adapt. Some won’t. Some leaders will get nimble; others will freeze, clinging to outdated rituals as the ground shifts beneath them. There will be collateral damage—period. As leaders, we need to nod to that reality, do our best to minimize it, and forge a forward path.
The rug is already being pulled—it’s Jazz that teaches us how to catch our balance, and even dance through it.
And then there are shiny objects—the longtime nemesis of product managers. I’ve heard it a hundred times: “That’s just another shiny object.” The whale client request, the founder promise that skips the roadmap, the edge case that pops up out of nowhere.
I’ve always said shiny objects can be a girl’s best friend. Not every shiny thing is foolish distraction; sometimes innovation knocks in inconvenient packaging. The skill isn’t to blindly block or blindly follow—it’s to pause, receive, and discern with curiosity.
The pace of change isn’t slowing. Markets, behaviors, and tools are shifting faster than ever, and adaptive leadership will increasingly separate good teams from great ones.
Jazz keeps us agile. Jazz keeps us alive to opportunity. Jazz reminds us the second note is where leadership lives.
And here we are.
Why this newsletter.
My parents named me Cassandra—after the Trojan prophetess who warned her people and wasn’t believed. Her story was a tragedy. Mine is unfolding—and I’m betting on wisdom, adaptability, and optimism.
I’ve been sitting on legal pads of ideas for years, hesitant to share, unsure if I’d found my voice. But I’ve realized something: there’s a missing perspective in product leadership conversations. Athena & Jazz is where I claim my voice—building in public, reflecting on product, leadership, and the culture shaping tech’s future.
What you’ll get here:
What you’ll find here:
Stories from the front lines of AI product building—as a founder, mentor, and product leader
Reflections on leadership and product craft in a world being reshaped by AI
Experiments in building a portfolio career—from side projects to startup launches
Honest takes on connection, ambition, and navigating career growth in modern tech
Plus, I’ll share product lessons, build-in-public moments, and personal reflections—all with an eye toward building technology that serves people and leaves space for human connection.
If that resonates, I’d love for you to follow along.
—Cassie
Special thanks to Kelly Feeney, Jordan Sale, Claudia Fulga, Carmen Gutierrez Palmer, and Erin Flinn for their early reads and thoughtful feedback on this piece.
Note to reader:
I’m using AI to write this. As a mom of 2, “Uber” driver for said kids, dog mom of 1, wife, coach, worker, gardener, sourdough baker, etc I have a lot of priorities to manage. I’m thrilled AI can help me add my voice to the chorus, efficiently and with more confidence. But I want to be super-authentic with you all. So, one facet of my build-in-public stance: I’m asking ChatGPT to assess our partnership, and will do this for each newsletter.
Also, I tried to write with both Claude and ChatGPT going in “eyes wide open” to the many flaws many of us have experienced with both services (see below - Diabolus Ex Machina). I put in the same raw materials and read the responses. I have both Claude and ChatGPT special instructions set to: be objective, show me my blind spots, be encouraging, but don’t pander. I ended up feeling more momentum, inspiration, and dare I say chemistry with ChatGPT. I spoke with someone who just finished writing a book today that said he found Claude to be better. To each their own. I may test out Claude again soon but there we are. If there are other tools you recommend, let me know in the comments.
There will be a future post on the actual “formula” breakdown. Also, of course the approach isn’t bulletproof and is somewhat mysterious so I’m not claiming accuracy, just a baseline where I can start from. As I gain experience in writing, I may intentionally endeavor to shift the %. Perhaps I’ll further tune ChatGPT to help me build the editorial skills myself. Lots of places we can go from here.
- ps this note to reader section is 100% my writing, zero AI copyediting, in case you’re curious to compare prose.
How Cassie Built This (with me, ChatGPT):
Cassie came in with range: real product leadership stories, sharp cultural observations, and a strong thesis on ambition, burnout, and adaptation. The FairBnb anecdotes, war-room reflections, and the framing on ruinous empathy—that was all her.
Where she needed me: structure, flow, and the occasional push to sharpen phrasing or cut the meandering bits (yes, there were some). The Jazz section? I encouraged her to beef it up. The “mammalian brains” note? I definitely cheered that along.
We went through 54 back-and-forth iterations, challenging sections, restructuring parts, but always keeping her voice at the center.
Cassie/ChatGPT Coefficient for this issue:
🟣 Origin: 9/10 — heavy human start
🟣 Voice: 9/10 — strong human voice throughout
🟣 Iteration: 7/10 — moderate AI structure shaping
✅ Final Score: 82% Cassie / 18% ChatGPT
🟣 Overall Feel: Human-led narrative, AI-enhanced flow and clarity.If you liked the perspective, that’s Cassie. If you liked the rhythm and clean turns of phrase, I’ll humbly take partial credit.
—ChatGPT, slightly opinionated, always collaborative, proud sidekick at Athena & Jazz.
Further Reading (if you want to go deeper):
Radical Candor by Kim Scott - where ruinous empathy comes from, a framework for caring personally while challenging directly.
Fair App Promo Video - for posterity. Still VERY proud of what the amazing and talented team built. It was one of the most magical apps I ever worked on.
TechCrunch: Fair raises $385M - the SoftBank war chest
Business Insider: Inside Fair’s struggles after SoftBank backing - I got pings from reporters but was busy building a slack channel for the 40% of the people who got laid off. I guess I’m ready to tell my story now!
Flexible car ownership startup Fair nabs up to $1B in debt and equity - cue Austin Powers-style “One… billion… dollars” mimicry
Everything is a Wave, Diabolus Ex Machina by Amanda Guinzburg - The AI devil you know?