Take second best, Put me to the test

Things on your chest, You need to confess

I will deliver, You know I’m a forgiver

Depeche Mode, Personal Jesus

This week is Holy Week and Passover all in one. Throw in there a trip to the moon during a full moon, and things are feeling pretty mystical. For Christians, the week is all about the journey from triumph to betrayal to crucifixion to resurrection–the literal path that Inc. Magazine used to write a story about Schoolhouse (more on that later).

For Jews, it’s passover. Slavery. Wondering. Deserts. Liberation.

Both stories matter.

At the core, they are about liberation.

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But before we get to the juicy Inc. story that everyone is gossiping about, we have to look at the other news in the world of entrepreneurship and business this week – cosmically timed:

Glossier announced it would close all but 3 stores and lay off roughly a third of its corporate workforce.

Allbirds closed all stores and sold for pennies on the dollar.

These brands were held up as pinnacles of successful entrepreneurship in the late 2010s. Even if you didn’t take venture capital and follow their path, your path as an entrepreneur in this millennium was shaped by them. It was sold to you that social media, digital advertising, and a strong “following” (hello Jesus!) were the keys to the kingdom of success.

But, as always, when I’m right, I’m right. And I’m going to take this holy week to get meta and quote myself from 2023:

We exchanged our integrity for certainty.

An entire cohort of entrepreneurs followed the lead of brands projected to them from an unformed media. I felt the same way when I read the “well-researched” Inc. piece about Schoolhouse. It may have been well researched, but it missed the most critical parts of the story.

Inc. took the most time-tested mythology in the holiest book and turned it into a story of small, well-meaning entrepreneurs meeting big, bad private equity. I think it should be known that this Substack you are reading right now is only available to you on a platform funded by TCG – the same group that is the villain in the Inc. story.

I have a personal connection with this story. I have never worked with or met anyone at Schoolhouse or Food52, but I did work with a client who was approached in a similar, not the same, manner as Emily Henderson. And so I knew this moment was on the horizon.

What is unfortunate about the Inc. article is that it missed the nuance we so desperately need to be surfaced in this time if we truly care about the future of creativity and commerce.

It’s deeper than a story about growth at all costs. What the moves of Glossier, Allbirds, and Parachute show is that it’s all the same story, and that’s a story about pattern matching and pride on both sides.

What is important to know about marrying investment with growth is that most investors are not operators. They are pattern matchers. It makes sense for numbers people to deploy techniques that make them feel safe. Investing due diligence is all about minimizing risk. Safety. But what investors didn’t realize when they were pattern-matching in our era is that the pattern was a mirage.

Operators tend to do the same thing: find people who share your values. Pattern match. But what are your values, and how do you know who shares them? Schoolhouse seemed to be wooed that Food52 was a “superfan” – flattering, I’m sure. They described the partnership as a natural fit. But what did that mean from an operational perspective? And how did those operational values align with TCG operational values?

The problem with branding your way to values is that those values ring hollow when it comes to operations and growth.

Both are an “outside - in” approach to growth. And if you’ve taken my business growth class, you know that doesn’t work.

This week, in the midst of all of this news, Tiger Woods crashed his car again. I use Tiger in my culture class to contextualize the dangers of building from the outside in. I feel for Tiger. As the child of an alcoholic, I know the lasting scars addiction leaves on entire families. But he said it so clearly in his 30 for 30 documentary years ago: Beware of building from the outside in. He knew his downfall was the brand he spent so much time trying to uphold.

I cannot stress enough how different it is to think about operations instead of brand.

If this week is showing us anything, it is that most brand strategies over the last decade were built around attention rather than loyalty. Followers, clicks, viral moments, likes: all of this is focused on grabbing attention, not building loyalty.

What is unfortunate about Schoolhouse is that they unknowingly traded the hard work they had done to cultivate loyalty to a pathway that operated with the lens of attention. They didn’t speak the same language, even if they thought they shared the same values. This isn’t a story of crucifixion. At its core, it is the Tower of Babel.

Schoolhouse spoke the language of operations. The rest of the group spoke the language of attention.

I want to close with an inspiring story. This week, quietly (had to do it!), another entrepreneur sold his legacy business for $29 Billion. His name is Nathan Kirsh. I imagine not one soul who reads this knows his name—I hadn’t even though I had been there myself. He is the founder of Restaurant Depot! Shout-out to all my restaurant workers who have made a last-minute trip to the depot in a pinch.

Kirsh started Jetro in Brooklyn in 1976. If you haven’t made the trip there yourself, it’s quite certain that any restaurant you have ever eaten at has an account at their local depot. What is interesting to me about the differences between these legacy brands is that Kirsh’s story could be seen as boring in today’s world. It’s why you’ve never heard of him. There are no clicks, no likes. No viral moments. No following. But everyone uses them. They were reliable. Dependable. Loyal.

I hope this era is over. For consumers. For creatives. For capitalists. It is not working. Not because one party is good and another is evil, but because, as Tiger has been screaming at us, building from the outside in doesn’t work. Branding is not what you thought it was.

The opposite of brand isn’t boring. The opposite of brand is bedrock.

Operations will deliver. They are also a forgiver! Reach out and touch faith!

RESCHEDULE: SUBSTACK LIVE! WHY DOES AI FAWN?

TBD! If you tried to join us yesterday, know you did not miss it. We will be rescheduling this event - stay tuned!

I will be joined by one of my favorite colleagues, Luis Mojica, to talk about why AI fawns, how we can stay embodied, and his new book! I love these conversations with Luis, and this one is sure to be fun and insightful!

APRIL WORKPLACE 2.0 WORKSHOP: Stop Generating. Start Creating.

Details: Thursday, April 30th 12 pm-1pmET via Zoom

It’s free - email me to register: holly@pyramid.work

By April, most entrepreneurs have spent Q1 producing content, activity, and output that look like building but belong to someone else’s playbook. In this workshop, we’ll audit what Q1 actually revealed about your business culture, trace what is genuinely and distinctly yours, and prune what doesn’t belong. You’ll leave with a recommitment to Q2 building from your own wellspring, not someone else’s template.

For those of you who joined in January and February, we will have the opportunity from 1 pm-1:30pmET to review the progress on your accountabilities.

I don’t want him [David L. Johnson] to get caught up in what are by now received ideas. I want him to foster his own voice and listen to where it takes him.

Hilton Als, The New Yorker

I only met Agosto Muchado once, very late in his life. Ryan, my husband, photographed his work for his last gallery show before he landed in the biennial.

I was taken by Agosto’s warmth and humility that he conveyed, and was inspired by just how prolific his body of work was. We were sad to learn that he passed over the weekend, but it also felt moving that it happened while his pieces were still up at the Whitney.

I appreciated Hilton Als critique of the show, especially on the cusp of Agosto’s passing.

I dramatically gasped when I read the phrase facsimiles of facsimiles. What I have called the derivative era has come for the art world. In the world of entrepreneurship, we’ve been stewing in it for over a decade. Though Als relates it to ChatGPT, it started in entrepreneurship with blanding and grids.

What is interesting about this path is that it is chosen by the individual themselves. We willingly lay down our own vision, point of view, and culture to reproduce what we feel is the best thing to get us to where we want to be. It’s not only disappointing on the consumer end, but it is actually what stagnates a company. If you find yourself sinking money into digital ads, it’s because you’re in the facsimile lane.

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To step out of that lane is to step into your own awareness of yourself and your personal history. To create without that context is to surrender the one thing that will serve as a wellspring of inspiration and ideation: your values and your purpose.

Entrepreneurship in the 21st century was a novelty to most people. It was the unconsidered pathway that is now becoming the norm. But it is long, and it is hard to find clarity in a world where generating something gets confused with creating something.

Don’t get caught up in received ideas! Be like Agosto: foster your voice:

• Know your values

• Respect your purpose

• Let them lead you to the vision only you know is possible

SUBSTACK LIVE! WHY DOES AI FAWN?

WEDNESDAY, APRIL 1 (APRIL FOOLS!) 12pm-1pmET

I will be joined by one of my favorite colleagues, Luis Mojica, to talk about why AI fawns, how we can stay embodied, and his new book! I love these conversations with Luis, and this one is sure to be fun and insightful!

APRIL WORKPLACE 2.0 WORKSHOP: Stop Generating. Start Creating.

Details: Thursday, April 30th 12 pm-1pmET via Zoom

It’s free - email me to register: holly@pyramid.work

By April, most entrepreneurs have spent Q1 producing content, activity, and output that look like building but belong to someone else’s playbook. In this workshop, we’ll audit what Q1 actually revealed about your business culture, trace what is genuinely and distinctly yours, and prune what doesn’t belong. You’ll leave with a recommitment to Q2 building from your own wellspring, not someone else’s template.

For those of you who joined in January and February, we will have the opportunity from 1 pm-1:30pmET to review the progress on your accountabilities.

ON JOY!

I recently got to share my Present Joys with Michelle & Joyce over at Present Studio. I love receiving their joys every week on their Substack, and I admire the beautiful work they put out in their studio. If you want to know what I’m doing on a Friday evening, read on. En-joy!

Present Joys

Present Joys Featured Guest: Holly Howard

This week we welcome Holly Howard, founder and CEO of Pyramid.Work, an AI-powered strategic growth engine for the entrepreneurial economy. We have been longtime admirers of Holly and her unique perspective on entrepreneurship, capitalism, and life! Holly is not your average business sage—she’s embraced many identities of her own (dancer, premed student…

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18 days ago

For him, the camera was but an instrument for expressing his intense awareness of life.

ICP on Eugène Atget

Many years ago, maybe somewhere around 2010, my husband had gone to the Chelsea flea market to browse. He saw a photo that caught his eye. He picked it up, and on the back of the frame it said, “Ruby Jester.” As a photographer, he was pretty familiar with historical photographers, and this name didn’t resonate. But nevertheless, he thought the photo had something to it, so he went and got $25 cash and came back to buy it.

Later that night, as we were watching TV and eating our homemade strawberry shortcakes, fingers coated in whipped cream, he decided to open the frame. We were excited with anticipation. The frame was janky, and we could not find a trace of a “Ruby Jester” anywhere on the internet. So he slowly peeled back the layers of the frame until the back of the photograph was exposed. And there it was, “Berenice Abbott.”

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A little high at the time, we thought we were being punked! I remember getting up off the couch and exclaiming, “Oh my god.” To find a Berenice Abbott print for $25 at a flea market was pure magic. And my husband knew right away, it was Eugène Atget, one of his all-time favorite photographers for whom Berenice championed in his life and death. Atget was regarded as a forefather of modern photography, taking photos around Paris in the late 1800s. They are haunting. Magical. For a young photographer who just moved to NYC a few years earlier, the moment was unbelievable for my husband.

On Saturday, after BLTs at Shopsins, we wandered over to ICP to see the Atget show that is up. What we found were the origins of the photo that now hangs in our entryway.

After talking to appraisers throughout the years, the mystery was finally solved. There it was in its original context. How the print made it into a frame stamped Ruby Jester and then to a flea market in Chelsea is a mystery we might never solve. And frankly, don’t want to.

In the midst of building a new company, I have spent a lot of time reflecting back on the moments of magic and mystery in my own life: why certain things came through out of nowhere that completely changed the trajectory of my life. I had just spent Saturday morning talking to someone about this (more on that soon). In some ways, I can look at the entire course of my life and see nothing but magical moments: getting into a Joffrey training program 2 days before graduation and dropping out of college, thereby changing the entire trajectory of my adult life. When I went back to Columbia to get my pre-med degree, I was in the School of General Studies, for the “non-traditional students.”

Nothing has served me more in life than being non-traditional. What once felt like a liability, “behind, off track,” has now revealed itself to be the gift of “seeing a different path when others don’t.”

As I have been actively fundraising for Pyramid, while building it, I am reminded of Tony Tjan’s book: Heart, Smarts, Guts and Luck.

I have thought a lot about how much luck actually plays in our pathways in life if we allow it. I have had to reckon with myself about how much I can “make something happen” and how much I should actually rely on the right things (time, people, opportunities) aligning. Luck is not without action. It is not about sitting back and waiting. There is a cheesy phrase that luck is just preparedness meeting the moment. In many ways, I think that is true.

My husband studied Atget for years as a young photographer and was able to see in that photo what the vendor and nobody else at the market could at that time. He knew the details subconsciously, and he took the action when the piece called to him.

We’re also in the midst of March Madness right now. Magic and Madness — the two polar-opposite experiences of building in the unknown.

When I think about basketball, I think about drills. I love going to games and seeing giant men tiptoe through rope ladders laid out on the floor. But there are no champions without footwork. Drills.

Drills are the tiny acts you repeat day after day to hone your skill, your knowledge, your self-awareness. We live in a time when drills are overlooked because they are full of friction, pain, and uncertainty. In entrepreneurship, we practice our drills when we repeatedly check our P&Ls, when we actively cultivate new and existing relationships consistently, and when we say no to an opportunity that isn’t aligned with our values.

Drills, when done with consistency and reverence, can make us feel alive because they can make us present to the opportunities around us that aren’t obvious. But they are hard. They, themselves, are not the reward. They are the portal into the unknown.

Atget drilled. He took his camera out daily. It changed his posture in the long-run. But he drilled. Over and over again.

When you build in the unknown, the known quantities are the drills. Luck, magic, and madness are just a result of being able to sustain yourself for things to align.

Every day, I get up and face rejection, misaligned colleagues, and a lot of uncertainty. But I can look at that Atget and remember the magic of the drills. I have had enough experience to know that grinding is what happens when the magic has been cast out of the creative act.

Do your drills. Let the magic in. Embrace the madness: the intense awareness of life.

Back during the pandemic, I decided to pursue a master’s certificate in religion at Harvard Extension. A certificate isn’t as big a commitment as a degree, and I could do it remotely. Check and check. It was an investment of both time and money, and the question I got most frequently from clients, family, and friends was: “Why?” “What are you ever going to do with that?” “How is this going to help your career?”

It’s funny how we’re constantly focused on outcomes. But I knew then, and believe even more so now: everything is religion.

Some people study religion to become more religious. That was not my intention. To me, the gift of studying religion is understanding the motivations of the world: Where does purpose come from? Why does it matter? Where do you find it?

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Today, I bring this up to bookend my newsletter from Monday about dopamine capitalism. Before Adam Smith was known for economics, he was a moral philosopher. He was most influenced by David Hume—a philosopher considered so dangerous in his time that he was occasionally barred from universities. Hume didn’t believe in the rationality of God; he believed in the humanity of it.

This was the soil Smith grew in—a world where economics was a branch of moral philosophy, rooted in our innate “sympathy” for one another. To Smith, we weren’t just calculators; we were a collective. Standing before Raven Halfmoon’s piece at the Biennial on Sunday, I felt that same Smithian pulse. Her work isn’t an individual achievement; it’s an ancestral collaboration. It’s an exchange that values the soul of the maker as much as the clay itself.

But somewhere along the way, we deviated from that humanity, and I put that on Milton Friedman.

What we rail against when we see an infographic about capitalism ruining the world is not the concept of exchange itself, but the result of capitalism when manipulated by Post-War economists like Friedman. It’s not that the Robber Barons who built America didn’t damage capitalism through Social Darwinism; Andrew Carnegie literally wrote the Gospel of Wealth. But that philosophy eventually collapsed and was replaced by something considered much more “rational,” though equally damaging: the idea that “shareholder value is the only rational metric.”

The sterile “rationality” of it is what made it acceptable, as opposed to the outright cruelty of Social Darwinism. We traded the human soul for a spreadsheet.

The week before the Biennial, I was at the Beacon Theatre to see Mavis Staples. Queen! One of the biggest surprises of the night was seeing my fellow music therapy colleague, Kyshona, opening for her. My heart literally exploded to see Kyshona’s trajectory over the last 20 years, from our days at Beth Abraham to the stage at the Beacon. It reminded me to stay the course.

Mavis herself was on fire. At 86, she took us there. For the last song, she conjured the spirits of all the Staples Singers and took us to that place of transformation. She has stayed the course.

I have thought a lot about that phrase, “I’ll take you there,” as it relates to modern capitalism. To engage in the exchange of goods and services for money isn’t actually rational. At its deepest, unconscious level, it is about transformation. How do you want to be changed? How does your customer want to be changed? It is why we choose, for better or worse, where our money goes.

We starve artists because we live in a society that puts supreme value on the “rational.” That is not the way Smith intended capitalism to be. The majority of the wounded men who run our societies determined that rationality was “safe.” It is as detached from feeling as they are from their own souls.

At the core of all of this—religion, art, and economics—is the question of Why? If we are to emerge economically viable, institutionally sound, and creatively cathartic, we have to have clarity on purpose. Purpose isn’t a “nice-to-have.” It is the catalyst for change. As my colleague Michael Bolognino recently wrote:

MB's Substack

Resilience, now.

Today I gave a workshop "Resilience, now." at my alma mater, Tufts University -- and given the state of the work world and world at large, here are ten perspectives that are available to you *right now* as tools to dust off and reclaim your resilience…

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a month ago · 7 likes · 1 comment · Michael Bolognino

Workplace 2.0 is recognizing that purpose is the foundation of what “takes us there.” Artists starve because we think the economy is about objects and productivity, not about transformation and impact.

I think about Milton Friedman and his peers—men who lived through the terrifying instability of the mid-20th century. In that context, I can see why he clung to the “rational.” Efficiency and shareholder value are clean; they are measurable. They provide a sense of control in a world that felt dangerously out of hand. But that rationality was also a defense mechanism—a way to avoid the messy, unpredictable, and vulnerable reality of being human. By trying to make the economy “safe” from our feelings, we ended up stripping it of its soul.

Today, we find ourselves in a similar moment. The world feels out of control again, vibrating with that same post-war instability. But we have a choice that Friedman’s generation didn’t feel they could afford. We can choose to lean into the messiness.

We have to recognize that the answer to a world in flux isn’t more control—it’s more creation.

Control is an attempt to freeze the frame; it’s a preservation of a status quo that has already set the world on fire. Creation, however, is the only way through. It requires the same “Sun Twin” spirit Raven Halfmoon invokes: the recognition that we aren’t just producing objects for a market, but participating in a transformative, ancestral lineage.

If we are to emerge whole, we have to stop hiding behind the safety of the “rational.” It’s time to stop matching old patterns and start creating the ones that will actually take us there.

Stay the course! Take us there!

BOOK CLUB NEXT WEEK!

NEXT WEEK, we will meet via Zoom to discuss our first book: Against the Machine by Paul Kingsnorth. It’s dense but super thought-provoking. If you like Wendell Berry, this is your jam.

Location: Zoom

Date: Thursday, March 19th, 12 pm-1 pm ET - on the cusp of the Spring Equinox

RSVP: This is a free event; please email me to register. I will send out the Zoom link the week of the event.

The first person I learned about money from was my dad. He was a CFO and naturally inclined toward numbers. He was also our family accountant and kept a strict ledger of our spending. He is the first person I had to ask for money. It started on Friday nights. By the time I was in high school, I needed $20 for gas, a cup of coffee at Denny’s, a pack of cigarettes, maybe to chip in on a baggie of weed, and gummy bears to wash it all down. The money sat in his money clip, on top of the refrigerator. I’d casually say as I was headed out the door, “I’m taking $20,” and then try to get to the garage before he objected.

Money was tied to approval and performance my entire life. Dad was always the gatekeeper. The irony is that for a chunk of my childhood, my father was unemployed due to his love of Gordon’s vodka and Old Style. It was my mom who carried our family when my dad couldn’t. But the mindset in our house never changed.

Today, March 9th, marks the anniversary of Adam Smith’s The Wealth of Nations; 250 years, just like America. It’s no secret that what we’re experiencing right now isn’t quite how Smith had envisioned capitalism. I like to imagine that if Smith were able to hop into a time machine, he’d be horrified in 2026, as we all are.

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Smith was a moral philosopher who asked us to think about how to take care of the lives of ordinary people. Recently, I have been thinking about how much of our consumer economy is built on dopamine: social media, gambling, crypto, porn, news feeds, and processed food. I am not sure how those are taking care of the lives of ordinary people.

I’ve been thinking a lot about what it means to be an entrepreneur in 2026 when so many processes are tied to dopamine: digital ads, stats, feeds, lists, followers, mentions, hits. The dopamine trap is all around us. It keeps us distracted and, most importantly, it profoundly disconnects us from our purpose.

The problem with purpose is that it doesn’t offer dopamine spikes. Purpose comes with moments of questioning. It comes with the dullness of doing your taxes. It forces you to create in the unknown; to self-validate without a requisite “like”. It is the antithesis of dopamine capitalism. Purpose calls you to embrace the ordinary. Just like Adam Smith.

Part of what I needed that $20 every Friday night in high school was my own dopamine dreams. Back then, I had to chase it. I had to contort myself for approval and perform for my share. It is weird to think that as an adult, I’d choose to do the same.

Purpose will never make you chase it. But it will refill you, like the bottomless coffee at Denny’s.

I remember where I was on July 17, 1999. I woke up on my bestie, Sean’s, sofa in Chicago. We had gone out late on Friday, July 16. Probably Wicker Park. Maybe Red Dog or Double Door. It was late, so on Saturday we woke up likely closer to noonish. It was late enough that the news of JFK Jr. and CBK had already spread our way. Analogue style. I remember smoking the first morning’s cigarette, thinking about how crazy it was that this was true. At this point, they were just “missing.”

I have been deep in Love Story these past few weeks, watching the first four episodes twice through. Listening to the audiobook and also reading the book. Furiously texting friends about each detail. The soundtrack! I know the show doesn’t do either one of them justice, but it does do the 90s justice.

What I think about the most, revisiting that time, is the transition from analogue to digital. This was the beginning of the end in many ways. I can’t imagine the sheer hell CBK lived in being hounded by the media. I can’t imagine what it’s like to have story after story fabricated about who you are and feel a loss of control over that narrative.

I can’t imagine the mental gymnastics she had to do to keep her sense of self when the signals being sent out about her were at odds with who she actually was. What I have thought about most as I read more in depth is about signals. And the static that blocks those signals.

We live in a much noisier world. And though I don’t think anyone reading this lives at the level of public exposure as someone like CBK, I do think a lot about the amount of signals everyone receives on a daily basis in our digital world and how conflicting those signals can be, especially as an independent entrepreneur. You and you alone get to decide what matters to you, and that can be overwhelming and scary.

How do you choose what you tune into? What signals you choose to tune into can be a matter of progress or stagnation in almost every case. The loudest signals aren’t always the right signals for you. How you decide about what you hear through the static and what you tune into will dictate the experience you have of your business and the type of success you have.

In January, we had a workshop about what you’re going to measure in 2026 and that is fundamentally defined by your values, purpose, and vision. The signals you need to tune into are also aligned to your purpose, values, and vision. If you are taking revenue, subscriber counts, customers, and product launches as your foundational signals, it’s highly likely you’re missing the drivers that matter most to your business. Stagnation isn’t due to the market; it’s due to the static blocking your ability to tune into the signals that keep your momentum going. Revenue growth is due to attunement to the right signals for your business.

In the end, disorientation cost JFK Jr., CBK, and her sister their lives. It was tragic. The same goes for the loss and stall of creative visions due to static that blocks our true signals. Remember, when nothing means anything anymore, you and you alone decide how to bring meaning to what you do. Move through the static. Identify your signals. And tune out the noise. You will make it to your destination.

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BOOK CLUB RETURNS!

In March, we will meet via Zoom to discuss our first book: Against the Machine by Paul Kingsnorth. I’ve started this! It’s dense but super thought-provoking. If you like Wendell Berry, this is your jam. The Atlantic referred to it as “cranky,” so naturally I’m intrigued.

Location: Zoom

Date: Thursday, March 19th, 12 pm-1 pm ET - on the cusp of the Spring Equinox

RSVP: This is a free event; please email me to register. I will send out the Zoom link the week of the event.

Culture is the family of the family. If the family has various sicknesses, then all families within the culture will have to struggle with the same malaises.

Clarissa Pinkola Estés, Women Who Run With the Wolves

When you step into the tech industry, one book that often gets pushed at you is Peter Thiel’s Zero to One. It was the bible of startup culture for over a decade. As we sit today, with social media companies on trial in LA, it has not aged well. But it’s still held up as the bible. I would wonder why that is, but I already shared the answer a few weeks ago.

When I first formed Pyramid and talked to a few people about my vision, the most common statement I received was that I was “too ambitious.” When I started fundraising, it was recommended to me that I read Zero to One. I was encouraged to essentially emotionally manipulate investors to give me their money by creating scarcity, limited opportunity, and FOMO—all considered best practices in fundraising(!) while we simultaneously watched the destruction of the minds of millions of children become warped by their investments.

Naturally, it sent me back to the drawing board. And then something happened when I was resetting my pathway. I went through menopause. Not perimenopause, but the full year of menopause. I was 47. That made me early to menopause and late to start-up culture—an intersection no one talks about.

There is a liberation that comes with menopause. In many ways, I felt like I fell off a cliff. Unexpected, unready. I went back to Women Who Run With the Wolves. I thought a lot about what I desired for the next phase of life. I thought about how much freer I feel in who I am and what I know about the world. I thought about the sickness in every corner of the tech industry and most of our society, mostly predicated on a philosophy of 0 to 1. And I thought about Estés.

I found in Estés what Theil couldn’t offer—a mirror rather than a playbook. Where Thiel encourages you to build through force, competition, and will, Estés invites you to intuition, instincts, cycles, and imagination. There’s a reason her book is more relevant 30 years on, and Thiel is a character on South Park.

Pyramid, is a mirror. It’s the tool that will give you the structure your instincts always deserved, but never had. I’ve spent a year learning how to build it on my own before going back out to finish the fundraising. That has been the gift. (If you’re interested in Beta Testing it [or investing!], email me as we’re going to start this spring!) It is the tool to guide you in your practices, your path. It is the container for a new culture. As Estés said, culture is the family of the family. The tech we’ve used is fundamentally sick, and we’ve all struggled with its malaise. Pyramid is my commitment to build something healthy enough to pass on.

BOOK CLUB RETURNS!

In March, we will meet via Zoom to discuss our first book: Against the Machine by Paul Kingsnorth. I’ve started this! It’s dense but super thought-provoking. If you like Wendell Berry, this is your jam. The Atlantic referred to it as “cranky,” so naturally I’m intrigued.

Location: Zoom

Date: Thursday, March 19th, 12 pm-1 pm ET - on the cusp of the Spring Equinox

RSVP: This is a free event; please email me to register. I will send out the Zoom link the week of the event.

When I moved to Williamsburg in 2002 with an ex-boyfriend, it didn’t take long for us to separate. Juicy details abound, but suddenly, I found myself living alone in South Williamsburg. My landlord, Clifford, was Puerto Rican, and he told the story of buying our building for $1 at auction in the late 90s and rebuilding it himself. He was so generous with me that when my ex moved out, he lowered the rent for years so that I could live there on my own—I made 40K per year. Clifford was, in many ways, my guardian angel for my early years in NYC. I felt safe under his roof.

Most of our block, and that section of Williamsburg, was populated by Puerto Ricans or Dominicans. Tina, who lived at 227, would hang out of her first-floor window most days, watch the neighborhood, and gossip! While right outside my door, I was usually greeted by Miguel (seated right) and his crew. They were a constant presence, and through the years, we grew to be buddies on the block. I felt I had people looking out for me when I was pretty lost.

So when Bad Bunny brought South Williamsburg, Toñita, and that community to the Super Bowl, it was joyful to see.

I have thought a lot about that word, calorcito, and what it means more than ever right now, and what we might learn from Ms. Cay.

Recently, I’ve seen a lot of panic about AI search and how it’s the next strategy to game. Sure, you can baseline try to fix your AI search, but it isn’t a winning strategy. It’s mostly a distraction from the real metrics that matter: human connection. The robots will always be one step ahead of keeping you twisted in knots trying to win the game. In Workplace 1.0, we were very confident in the data big tech reported to us as winning metrics. We lost our inner knowing that eyeballs do not make relationships. Data is cold. Relationships are built on warmth.

Calorcito - warmth - is about the daily practice of knowing someone. You do not know someone through metrics and demographics. You know them by being curious about who they are, how they live, and what they need. You nurture them, you genuinely care who is on the other side of the transaction you’ve engaged in. How you make someone feel will matter more than how many ads they see or how often ChatGPT randomly predicts your business in its responses.

Toñita didn’t optimize for discovery; she optimized for memory in a way that only she can. She is ahead of Workplace 2.0.

Where is your time focused? On your digital strategy or your relationship building? Do you believe more in the wisdom of Sam Altman or Ms. Cay?

The robots can help people find you. But only calorcito makes them stay.

TWO FREE EVENTS IN FEBRUARY!

Substack Live with Frederick Woodruff

Wednesday, February 18th at 1 pm-2 pm ET

I’m bringing in one of my favorite astrologers to help you understand what Saturn-Neptune in Aries actually means for entrepreneurs, leaders, and anyone building something that matters.

Frederick Woodruff will give you the context: What’s this cycle we’re entering? What does it mean when dreams hit reality? Why does this moment favor independent builders over institutional followers? You can listen to the conversation I had with Frederick last year here.

Tune in on the 18th where Frederick will lay out the weather report for us and be ready for the 19th!

The Delta Workshop: Making Decisions at the Crossroads

The day after we understand the cosmic context, we’ll learn how to use it.

Saturn-Neptune in Aries is going to ask you hard questions. When your dream hits financial reality, how do you decide? When your vision meets operational constraints, what do you do? When there’s no right answer, only your answer, how do you choose? I’ll help you bring yesterday’s newsletter to life for you. You too can think like a Nobel Prize-winning economist.

We’ll work with real decisions. We’ll see you at the crossroads: real moments where dreams meet discipline, and you need to know what YOU would do, not what someone else thinks you should do.

This workshop will give you:

• The Purpose-Values-Vision framework for decision-making under uncertainty

• How to use your values when you’re questioning “best practices.”

• Why your practices, not “best practices,” are what will carry you through the next era.

Location: Zoom

Date: Thursday, February 19th, 12 pm-1 pm ET**

What to bring: A real decision you’re facing right now, something where your dream is meeting reality, and you’re not sure how to choose. It could be about pricing, partnerships, pivoting your offer, saying no to an opportunity, or anything else where there’s no clear “right answer.” We’ll work with live examples. Please bring your purpose, values, and vision as well.

RSVP: This is a free event; please email me holly@pyramid.work (or just respond to this email) to register. I will send out the Zoom link the week of the event.

**If you attended January’s workshop and set your metrics for the year, you can also stay after to share progress or check in on accountability. We will set aside 30minutes for this. If you missed January’s workshop but still want to complete the worksheet, you can do so here.

The cosmic weather shift is upon us! I hope you’ll join us for some fun sessions and serious skill-building.

BOOK CLUB RETURNS IN MARCH!

In March, we will meet via Zoom to discuss our first book: Against the Machine by Paul Kingsnorth. I’ve started this! It’s dense but super thought-provoking. If you like Wendell Berry, this is your jam. The Atlantic referred to it as “cranky,” so naturally I’m intrigued.

Location: Zoom

Date: Thursday, March 19th, 12 pm-1 pm ET - on the cusp of the Spring Equinox

RSVP: This is a free event; please email me to register. I will send out the Zoom link the week of the event.

The following year, I joined a gym in South Brooklyn, mostly run by former Soviet athletes. I was in search of a pool, and it was a dream to find. I didn’t think about how much I would love my new community of mostly expats from Russia, Ukraine, and Belarus. On most days, I’ll rise at 4 to make it to the pool for an open swim. This means that the first thing I hear when I step into the world is добро утро or dobro utro! Dobro utro! Dobro utro! Dobre utro! At first, most of our fellow swimmers were skeptical of my husband and me, clearly not fluent in Russian and unable to engage in the morning gossip. But it didn’t take long for them to take a liking to us; mostly, I believe, because all of the ladies over 70 are in love with my husband. (When he skips a swim, I hear “Where is your husband?!”)

I have always been at home in the water thanks to my mom (the Fish). I started in competitive swimming young and later switched to competitive diving. On Tuesdays and Fridays, if we choose to swim, it means we train alongside the young swimmers, again mostly the children of expats, who are training for competitions as serious as the Junior Olympics. Observing their practices reminded me that ex-Soviet sports training is truly a love language for me. It can go too far, but when it’s boundaried, it’s the best. I love the alchemy of reverence and intensity. The sheer commitment to transcend one’s own physical limitations. I see it as another form of prayer.

Swimming is where I do my best thinking. I wear earplugs so it’s immensely quiet for one hour, no noise except that of the water. It allows me to hear my thoughts and workshop most of my day. I write most of my newsletters while I’m lap swimming, only to transcribe them when I’m out.

So it makes sense that Pyramid was born in the water. It was April 25, 2024. I was lap swimming.

If you followed along with my journey over at Ask Holly How, you would have heard me talk about my desire to one day open a school. I started planning this school in earnest back in 2019. I have always known that we are lacking modern business education. That most programs out there are antiquated and not aligned with who the modern entrepreneur actually is or wants to become.

On April 25th, 2024, I was in the water and noodling about what this school could be. Everything I’d tried up to that point felt too bland. I didn’t want to make another business program, another online academy. Nothing felt worthy of what I actually wanted to create: something that could unify creativity and commerce in a way that honored both.

I was doing freestyle in the deep end when, right before touching the wall, I dove the way I used to in my competitive diving days, hitting the bottom of the pool (it makes my husband roll his eyes). And in that descent, it came to me.

The business triangle had been my framework for over a decade. But suddenly I saw its limitation as something you looked at, something you worked with as a tool. What if instead of working ON a triangle, you could step INSIDE one? (Reverse of the E-myth!) What if there was a three-dimensional space that could actually hold you—the entrepreneur—and hold your entire business?

Task managers hold your time. Project management software holds your tasks. But nothing holds the company itself. Its essence. The bridge between you as an entrepreneur and the company you create: your vision, your values, your purpose, and every decision that flows from them.

The word surfaced with me: Pyramid. A triangle brought to life. And

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sacred—da Vinci, Egypt, Hilma af Klint. A form that’s held meaning across centuries and civilizations.

I showered, hopped into my car, and before I pulled out of the parking lot, I secured the domain: Pyramid.work. This would be the school. The next evolution of this work.

Little did I know what a journey it would be! And now I’ll start sharing it with you. All of the twists and turns of the last two years and what’s on the horizon for 2026. The Scheme will be dedicated to what it’s like to build something now. And because when I’m right, I’m right, I’ll close by saying that Pyramid, like both the teams in the Super Bowl is a study of what it’s like to go on a journey:

TWO FREE EVENTS IN FEBRUARY!

Substack Live with Frederick Woodruff

Wednesday, February 18th at 1 pm-2 pm ET

I’m bringing in one of my favorite astrologers to help you understand what Saturn-Neptune in Aries actually means for entrepreneurs, leaders, and anyone building something that matters.

Frederick Woodruff will give you the context: What’s this cycle we’re entering? What does it mean when dreams hit reality? Why does this moment favor independent builders over institutional followers? You can listen to the conversation I had with Frederick last year here.

Tune in on the 18th where Frederick will lay out the weather report for us and be ready for the 19th!

The Delta Workshop: Making Decisions at the Crossroads

The day after we understand the cosmic context, we’ll learn how to use it.

Saturn-Neptune in Aries is going to ask you hard questions. When your dream hits financial reality, how do you decide? When your vision meets operational constraints, what do you do? When there’s no right answer, only your answer, how do you choose? I’ll help you bring yesterday’s newsletter to life for you. You too can think like a Nobel Prize-winning economist.

We’ll work with real decisions. We’ll see you at the crossroads: real moments where dreams meet discipline, and you need to know what YOU would do, not what someone else thinks you should do.

This workshop will give you:

• The Purpose-Values-Vision framework for decision-making under uncertainty

• How to use your values when you’re questioning “best practices.”

• Why your practices, not “best practices,” are what will carry you through the next era.

Location: Zoom

Date: Thursday, February 19th, 12 pm-1 pm ET**

What to bring: A real decision you’re facing right now, something where your dream is meeting reality, and you’re not sure how to choose. It could be about pricing, partnerships, pivoting your offer, saying no to an opportunity, or anything else where there’s no clear “right answer.” We’ll work with live examples. Please bring your purpose, values, and vision as well.

RSVP: This is a free event; please email me holly@pyramid.work (or just respond to this email) to register. I will send out the Zoom link the week of the event.

**If you attended January’s workshop and set your metrics for the year, you can also stay after to share progress or check in on accountability. We will set aside 30minutes for this. If you missed January’s workshop but still want to complete the worksheet, you can do so here.

The cosmic weather shift is upon us! I hope you’ll join us for some fun sessions and serious skill-building.

This shift will reward entrepreneurs who build from their own foundations, not borrowed ones. The cosmic weather is shifting away from "best practices" and toward your practices. Away from following and toward pioneering. Away from dreaming without doing and toward dreams that require discipline.

This is the infrastructure moment for the creative economy. This is why Pyramid exists right now. This is the shift from Workplace 1.0 to Workplace 2.0.

And we’re going to help you work with it.

Understanding the Cosmic Weather

Substack Live with Frederick Woodruff

Wednesday, February 18th at 1 pm-2 pm ET

I’m bringing in one of my favorite astrologers to help you understand what Saturn-Neptune in Aries actually means for entrepreneurs, leaders, and anyone building something that matters.

Frederick Woodruff will give you the context: What’s this cycle we’re entering? What does it mean when dreams hit reality? Why does this moment favor independent builders over institutional followers? You can listen to the conversation I had with Frederick last year here.

Tune in on the 18th where Frederick will lay out the weather report for us and be ready for the 19th and 20th!

The Delta Workshop: Making Decisions at the Crossroads

The day after we understand the cosmic context, we’ll learn how to use it.

Saturn-Neptune in Aries is going to ask you hard questions. When your dream hits financial reality, how do you decide? When your vision meets operational constraints, what do you do? When there’s no right answer, only your answer, how do you choose? I’ll help you bring yesterday’s newsletter to life for you. You too can think like a Nobel Prize-winning economist.

We’ll work with real decisions. We’ll see you at the crossroads: real moments where dreams meet discipline, and you need to know what YOU would do, not what someone else thinks you should do.

This workshop will give you:

• The Purpose-Values-Vision framework for decision-making under uncertainty

• How to use your values when you’re questioning “best practices.”

• Why your practices, not “best practices,” are what will carry you through the next era.

Location: Zoom

Date: Thursday, February 19th, 12 pm-1 pm ET**

What to bring: A real decision you're facing right now, something where your dream is meeting reality, and you're not sure how to choose. It could be about pricing, partnerships, pivoting your offer, saying no to an opportunity, or anything else where there's no clear "right answer." We'll work with live examples. Please bring your purpose, values, and vision as well.

RSVP: This is a free event; please email me holly@pyramid.work (or just respond to this email) to register. I will send out the Zoom link the week of the event.

**If you attended January’s workshop and set your metrics for the year, you can also stay after to share progress or check in on accountability. We will set aside 30minutes for this. If you missed January’s workshop but still want to complete the worksheet, you can do so here.

The cosmic weather shift is upon us! I hope you’ll join us for some fun sessions and serious skill-building.

Holly

Someone recently told me they’re rethinking AI because it is biased (a comment I hear a lot). It makes me chuckle, not because they’re wrong, but because they think bias is an AI problem. Everyone is biased. I’m biased. Your peers are biased. That consultant who promised to remove bias from your processes? Especially biased.

A few years ago, there was a flood of HR software that claimed to “take the bias out of hiring.” Total scam. But companies bought them anyway, not because they worked, but because outsourcing to an algorithm felt safer. When things went wrong, you could say “the system decided.”

Software is biased because the humans who build the software are biased. Best practices are biased because the people who deem them best practices are biased. And here’s what everyone’s favorite Nobel Prize-winning economist Richard Thaler would tell you: bias isn’t a bug in human decision-making. It’s a feature.

Last week, I was teaching the culture module in the business growth program, and I always show this photo of Thaler to talk about behavioral economics:

I teach Thaler early because a foundational grasp of behavioral economics is vital in entrepreneurship. We, it turns out, aren’t as rational as old men would like us to believe. Much of Thaler’s work centers on status quo bias and loss aversion: we choose familiar failure over unfamiliar success. (Thaler also just happened to be on Jon Stewart’s pod yesterday for a very funny and bit rambling conversation!)

This is why best practices are so comforting. They abdicate our responsibility for loss and keep us from the discomfort of imagining something new. We say we want to change the economy, capitalism, workplace practices, but we’re scared of stretching into unvalidated approaches. That is extremely Workplace 1.0. It’s why we never become the change we wish to see in the world. Instead, we wait for others to make that change first.

That’s the path the Vikings took in the winter of 2025.

The Vikings weren’t being irrational when they cut Sam Darnold. They were being human.

They chose the status quo: the established pattern that says playoff performance predicts future performance. The safe and defensible answer. The answer that meant if it didn’t work out, they could point to decades of data and say, “We followed best practices.”

But here’s the thing about status quo bias: it doesn’t feel like bias. It feels like analysis. It feels like being smart. The Vikings’ front office didn’t think they were making an emotional decision. They thought they were looking at the data, following the playbook, doing what successful franchises do.

That’s what makes status quo bias so insidious. It disguises itself as objectivity. The next time you’re about to follow a best practice, ask yourself: Am I optimizing for not being wrong? Or am I optimizing for being right?

Am I choosing this because it’s what worked before? Or because it’s what would work for ME?

Am I outsourcing my judgment to someone else’s playbook? Or am I trusting what I actually see and know could be possible even if it stretches my leadership?

Seattle asked different questions.

Not: “What does the data say about playoff chokers?”
But: “What do we see in THIS player?”

Not: “What would a championship team do?”
But: “What would work for US?”

The Vikings optimized for not being wrong. For looking legitimate. For having a defensible decision when it failed.

Seattle optimized for being right. For their context, for this player, for what they actually needed.

One approach follows the status quo. The other creates possibilities. That’s Workplace 2.0.

And now Sam Darnold is going to the Super Bowl. With the Seahawks.

Tomorrow I will be announcing our February Workshop and a very exciting Substack Live! Stay tuned, make your taco dip, and go Seahawks!

For the past two months, I’ve been trying to work my way through Ken Burns’ The American Revolution. Right now, I find it a bit too intense and violent to take much in at a time. But last week, Burns was speaking at The Met, so we went to see him talk about his process which was a great way to re-engage with the work. I know he’s on tour so if you get a chance, I recommend it.

What was helpful about this lecture was to look at the history through the art the used. No cameras back then, so little material to provide concrete truth. The irony of today when there are too many cameras and too much material and we still can’t agree on concrete truth. One image that took me was a watercolor they commissioned from Greg Harland showing that:

When I started grad school years ago, we had to give our reason for enrolling. I said "to confront my ignorance.” It’s a passion of mine, to reveal to myself that which I wasn’t aware of. It try to keep it an active practice or I can feel my world and my brain shrinking. Full disclosure, I thought the Revolutionary War ended with the signing of the Declaration of Independence. I’m quite sure, my father, who was a history major at Princeton is raging at me from his grave.

I’ve never heard Burns speak, but he is feisty! He as a fierce defender of history and it was inspiring to witness. As we’ve been working our way through the series, I continually ask my husband what he thinks the people who died for America would think of it now. I like to say, “do you think they died so people could scroll tiktok?” Imagine. There are so many letters witnessing the revolution from every perspective listed above that watercolor. Though we like to try to simplify the narrative about white men, not paying taxes (still true today!), there was so much more imagination of possibility from every group. In the discussion at the Met, possibility is a word they agreed on.

Which brings me to The Secret Mall Apartment. If you haven’t seen it, call in a sick day and indulge yourself. I’m pretty sure this is the type of activity that anyone who actually sacrificed for the idea of America would be pleased with. It is about possibility. It’s also about the space that’s meant to hold up the facade, but not be seen. That is the story of America. The mall wants you to believe in the 4th of July brouhaha. The secret mall apartment, invites you into the truth of possibility, into an opportunity to think about how you see your role, your contributions, and how you live within someone else’s reality, someone else’s imagination.

We’re all scheming (VISION) in one way or another. The question is how (VALUES) you’re doing it. Are you setting up shop next to the food court because those “best practices” indicate that’s the way it works? Or are you secretly subverting common wisdom and creating possibility for yourself and others to creatively thrive?

What we lose when we simplify mythology, is the ability to expand our awareness and grow. We get caught up in the bias of the binary. In our over simplification, we fail to see the space of possibility that’s been there all along, waiting for us to emerge.

Cherry on Top🍒

Your 2026 Doesn’t Need a Better Plan. It Needs a Better Vision.

Ally here! In January, the air shimmers with the promise of a fresh start, the vast expanse of the new year laid out before us like an untouched field of newly fallen snow…

Read more

2 months ago · 11 likes · Alex Daly & Ally Bruschi

REMINDER! Workplace 2.0: The Delta

I’m hosting the first Workplace 2.0: The Delta workshop to help you clarify what you’ll actually measure in 2026. And most importantly, why. IT’S TODAY!

We’ll go beyond the basics (revenue, followers, team size) to align your metrics with your specific purpose, values, and vision. Because if you’re measuring the wrong things, you’re optimizing for someone else’s definition of success.

What we’ll do together:

• Audit what you’re currently measuring (explicitly and implicitly)

• Identify gaps between what you say matters and what you’re tracking

• Design 3-5 personalized metrics that reflect YOUR vision and values

• Build accountability structures that support revelation, not perfection

I like to establish clear accountabilities in January and see where I land in December. It’s not about perfection. It’s about revealing what’s actually true.

Location: Zoom

Date: TODAY! Thursday, January 29th, 12 pm-1 pm ET

What to bring: Whatever metrics you’re currently tracking (revenue, hours, followers—anything) and honesty about what’s really driving your decisions.

RSVP: This is a free event; please email me to register. I will send you the Zoom link. If you registered and did not receive the link already, please respond to this email directly or check your spam folder first!

A few years back, during the 45th administration, my husband and I returned home to Minnesota for Christmas. Weed had accidentally been legalized, so when we landed, we picked up some gummies for the stay and made our way south. On Christmas Eve, we decided to attend mass with my in-laws, but I thought it would be a good idea to take an edible beforehand. The church they attend is out in a corn field, a tiny chapel that glows in the abyss.

As a lapsed catholic, and being slightly buzzed, I decided it was best to sit in the last pew behind everyone. I ended up seated behind a very vocal Trump supporter. In between verses of Away in a Manger and Angels We Have Heard on High, I spent most of the service reflecting on whether I could find it in my heart to see this man in front of me as a child of God—whatever that actually means.

I never got there. Instead, I went home and chaotically binged my mother-in-law’s homemade raspberry jam with Cheeze-its—highly ;) recommended!

Minnesota is heavy on our minds. This past Saturday, we went up to The Hill Collection on W. 24th to see Robert Bergman’s Portraits. Bergman was raised in, and still lives in Minnesota. David Levi Strauss curated the show and hung Bergman’s portraits alongside traditional masters.

That phrase, “who is worthy of being portrayed,” feels heavy right now. Who is worthy of dignity? Of being seen as human? Of protection?

I’ve been thinking about that church pew recently. The rage. And now, how the dignity that Alex Pretti extended to so many veterans was never reciprocated.

I’ve been thinking a lot about rules. Where they come from, why we live by them.

I’ve been thinking about what it means for America to be on the cusp of its 250th. 250 years of asking “who is worthy?”

Looking without vision is an act of voyeurism. And voyeurism is a cheap thrill with reactionary consequences.

So the question I leave you with, today, this year, and for as long as you grace this earth is, what does it mean to look WITH vision—to let what you actually see change the world you build?

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REMINDER! Workplace 2.0: The Delta

I’m hosting the first Workplace 2.0: The Delta workshop to help you clarify what you’ll actually measure in 2026. And most importantly, why!

We’ll go beyond the basics (revenue, followers, team size) to align your metrics with your specific purpose, values, and vision. Because if you’re measuring the wrong things, you’re optimizing for someone else’s definition of success.

What we’ll do together:

• Audit what you’re currently measuring (explicitly and implicitly)

• Identify gaps between what you say matters and what you’re tracking

• Design 3-5 personalized metrics that reflect YOUR vision and values

• Build accountability structures that support revelation, not perfection

I like to establish clear accountabilities in January and see where I land in December. It’s not about perfection. It’s about revealing what’s actually true.

Location: Zoom

Date: Thursday, January 29th, 12 pm-1 pm ET

What to bring: Whatever metrics you’re currently tracking (revenue, hours, followers—anything) and honesty about what’s really driving your decisions.

RSVP: This is a free event; please email me to register. I will send out the Zoom link WEDNESDAY.

Behind my workspace at home hangs this portrait of Beth Gibbons. I have thought about how intensely private she is. A bit different from the narcissists I wrote about in The Scheme on Monday. So I was excited to see the latest episode of Bandsplain come out today—a 4 hour discussion of Portishead’s origins in Bristol. But what does Beth Gibbons and Bandsplain have to do with hiring?

When we’re hiring—whether actual W2 employees or 1099 contractors—we’re building a team. And teams require alchemy: different perspectives, different skills, different ways of seeing. But somewhere along the way, we started optimizing hiring for efficiency instead of humanity.

Social media was the first poison, contracting our openness to others by reducing people to profiles, curated highlights, and professional personas. Sprinkle a little AI into your hiring mix, and you’ve got a recipe for sterile sameness.

Alchemy is messy. It requires friction, difference, the unexpected collision of perspectives. You can’t algorithm your way to it. You can’t automate chemistry.

But here’s the paradox: alchemy needs a container. Without structure—clear hiring processes, defined roles, grounded leadership—the mess becomes chaos instead of creative tension. The work is building containers strong enough to hold the alchemy without crushing it.

Humanity is one of the hardest parts of being an entrepreneur. In recent years, we've confused creating structure with being controlling. Or we've swung the other direction, becoming so enmeshed with our teams that boundaries dissolve. AI feels like a lifesaver because it promises to remove the messy human part entirely. Oh, the mental load this will relieve if I don’t have to psychologically engage with humanity!!

This isn’t to knock AI as a tool; it’s to highlight how it’s being misused. Instead of using AI to flatten humanity, as this NYT article describes, use it to help you create your container. Then do the human work yourself. That container includes:

• Having a clear job description for the role

• Having a clear job posting for the role (different from the full job description)

• Having a clear interview protocol and process to follow

• Having inspired questions that open dialogue about performance and culture

• Having a clear onboarding and training protocol supported by standard operating procedures that take the guesswork out of how to function within your company

• Having the courage to communicate with someone when you feel things are off track

• And having the respect to reinforce when they are rising to the occasion

AI can be a profoundly helpful tool to help you build this container, the structure that holds both you and your team. But if you’re outsourcing your thinking about how to evaluate someone based on a few bullet points and an algorithm, you have a much deeper reflection to sit with.

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Here’s what Yasi taught me about building a team—the alchemy that made Portishead extraordinary wasn’t efficiency or predictability. It was Geoff Barrow’s hip-hop sensibility colliding with Beth Gibbons’ raw vulnerability and Adrian Utley’s jazz background. It was three people who shouldn’t have worked together on paper, held in a container of shared vision and deep respect. (PS Geoff and Beth met at a free business class - lol ;)

That’s what hiring should be. Not finding the perfect algorithmic match. But creating a strong enough container—clear roles, processes, values—that different kinds of people can come together and create something none of them could have built alone. That’s the work in hiring, too. Stay human. Build the container. Let the alchemy happen.

I was extremely flattered because I knew I obviously deserved it. Of course, I wanted it. I was seething with jealousy when he got it. Seething. But I played it cool. Sean and I have a long history. We met on the first day of high school at the bus stop. He was in his Chicago Bulls t-shirt, and I was likely in biker shorts (#slay).

It wasn’t quite grade school, but it was early enough in my life that Sean left a big impression on me. He was handsome. He was funny - the ultimate meme queen. He drove a chocolate brown Volvo. His abs were better than mine.

So I’ve always been susceptible to his shenanigans. But Sean's joke hit different this week because while he was texting me about fake Nobel Prizes, Muchado was actually, genuinely offering hers to Donald. Not as a joke. As a real gesture that she seemed to think was meaningful.

And that's when I read Adam Grant's piece in the New York Times about why we keep falling for narcissistic leaders.

The piece highlighted something I've been watching play out everywhere, not just in politics, but in business, in startup culture, in the endless parade of charismatic founders who burn through teams and leave destruction in their wake. It also happens a lot in the “expert economy” too. Gurus offering certainty when the world is deeply uncertain.

Yesterday, on MLK day, my husband and I spent a lot of time talking about purpose. What is our (individual) purpose? What is the purpose of any of this? I said, if I think about what I care about the most, it is ultimately about calling bullshit. Truly. I think I have a skill, better than anyone I know, to detect a fake. And fake leaders are all around us. They are those start-up martyrs working 100-hour weeks to bring you the next sub-par technology. They are those charismatic social media personalities who know how to manipulate you through infographics.

As Adam Grant says, part of why we fall for them is because of how we feel about ourselves. But here’s the thing. The world needs more, not fewer, leaders. Just because we’re appalled by the leadership we see doesn’t abdicate our responsibility to provide ourselves, our families, our teams, and our communities with the leadership they need to change.

Fake leaders trade in vague promises and borrowed wisdom (and borrowed Nobel prizes). But the antidote isn’t cynicism, it’s self-awareness. It’s last week’s lesson about specificity. It’s knowing why you’re here. How you want to behave and what you’re creating in the absence of external validation. It is the opportunity to know yourself more clearly and deeply. The clearer you are about yourself, the less you need a narcissist to tell you who to be.

Book Club Returns!

In March, we will meet via Zoom to discuss our first book: Against the Machine by Paul Kingsnorth. Full disclosure, I haven’t read this yet and will be reading it alongside you. The Atlantic referred to it as “cranky,” so naturally I’m intrigued.

Location: Zoom

Date: Thursday, March 19th, 12 pm-1 pm ET - on the cusp of the Spring Equinox

RSVP: This is a free event; please email me to register. I will send out the Zoom link the week of the event.

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Workplace 2.0: The Delta
January: What Are You Actually Measuring?

This quote always gets me going. As we head into the new year, I’m hosting the first Workplace 2.0: The Delta workshop to help you clarify what you’ll actually measure in 2026. And most importantly, why!

We’ll go beyond the basics (revenue, followers, team size) to align your metrics with your specific purpose, values, and vision. Because if you’re measuring the wrong things, you’re optimizing for someone else’s definition of success.

What we’ll do together:

• Audit what you’re currently measuring (explicitly and implicitly)

• Identify gaps between what you say matters and what you’re tracking

• Design 3-5 personalized metrics that reflect YOUR vision and values

• Build accountability structures that support revelation, not perfection

I like to establish clear accountabilities in January and see where I land in December. It’s not about perfection. It’s about revealing what’s actually true.

Location: Zoom

Date: Thursday, January 29th, 12 pm-1 pm ET

What to bring: Whatever metrics you're currently tracking (revenue, hours, followers—anything) and honesty about what's really driving your decisions.

RSVP: This is a free event; please email me to register. I will send out the Zoom link the week of the event.

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My husband and I have a saying that we throw to each other when we’re confronted by current events: “Nothing means anything anymore.” I think about it constantly. When there’s no “back to normal,” it forces you to think about what you use to orient yourself: to your own inner voice and to the larger world around you. As I have written many times before, we are each living inside someone else’s imagination as well as our own. When nothing means anything anymore, it forces us to evaluate our own capacity to imagine what brings us meaning and how we sustain an orientation to that in such a noisy world.

The antidote to this meaninglessness isn’t more noise, more opinions, more general declarations about what matters. It’s specificity.

Specificity negates judgment. George Saunders on The Daily.

Our truest compass in the world is comprised of three pieces: our vision, our values, and our purpose. These aren’t just the “nice to haves” or “soft skills” of entrepreneurship. They are our navigation system in a rapidly changing world. The depth of our relationships to these pieces determines how effectively they guide us. Specificity is key in that relationship.

This weekend, I went to the closing reception for my friend Reverend Joyce McDonald’s work at the Bronx Museum. Joyce calls herself a testimonial artist. Her work is based purely on her lived experience—and what a life it has been. The results are a body of work that conveys her values: family, devotion, and grace. Her purpose with the clay is pure. When she creates, she speaks clearly, deeply connected to her own vision of the world she wants to be a part of.

Joyce’s clarity didn’t come from a workshop or a business coach. It came from being radically honest about the specifics of her life: where she’s been, what she’s survived, what matters to her now. That specificity is what makes her work powerful. It’s also what makes it hers.

Most entrepreneurs I work with struggle not because they lack vision, values, or purpose, but because those things remain vague. “I want to help people.” “I value integrity.” “My purpose is to make a difference.” These aren’t compasses. They’re the fog.

The work is getting specific. Not borrowing someone else’s values from a LinkedIn post. Not adopting a vision because it sounds good. But doing what Joyce does: looking clearly at your lived experience and naming what’s actually true for you.

That’s what Pyramid is about: building the practice of specificity so your vision, values, and purpose can actually guide you. In the end, it isn’t the organization that propels you forward and allows your creativity to flow. It’s orientation. Without it, everything else dissolves into fog.

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Where I’ve Been, Isn’t Where I’m Going

Hello! If you’re receiving this email, it’s because you’ve either subscribed to Pyramid Schemes directly or you’re a former Ask Holly How Newsletter Subscriber. For those of you in the latter category, as I mentioned in December, all of my writing will shift to this Substack. And here we are.

This is just a welcome email. A moment to step into the joy and sorrow that is already 2026. This newsletter will be different from my previous work. I’ll still be sharing philosophical takes on culture and work, but I’ll also be providing more practical advice on building sustainable work here. Not in a LinkedIn Lunatics sort of way (unless that is your vibe and I salute you and support you living your truth!).

When I was home over the break, my husband picked up a copy of David Foster Wallace’s This is Water. I remember when he gave this speech, but it was good to reread it and especially while on break. My aim with Pyramid is to create a space for the creation of work where you choose: you choose how to construct meaning from the experience you are having. Entrepreneurship is a privilege. How we orient ourselves within it is our choice. We can be a lunatic (s/o if that is your vibe) or we can be awake to the water we are living in.

The purpose of this evolution is to bring this work to a wider audience and to give us more opportunities to connect both online and in person. There’s also something much, much bigger brewing that I’ll start to tell you about next week! You can expect free monthly workshops, quarterly book clubs, and Substack lives with some really great guests. For now, this is to say hello. And if you have any book recommendations or workshop topics that interest you, please drop them in the comments! I’m glad you’re here and ready to scheme with me.

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