2025-08-14 05:54:00
A few things I’ve come to terms with:
There is rarely more or less economic uncertainty; just changes in how ignorant people are to potential risks.
You should obsess over risks that do permanent damage and care little about risks that do temporary harm, but the opposite is more common.
The only way to build wealth is to have a gap between your ego and your income.
Everyone belongs to a tribe and underestimates how influential that tribe is on their thinking.
A lot of financial debates are just people with different time horizons talking over each other.
It’s easy to mistake “I’m good at this” with “Others are bad at this” in a way that makes you overestimate how valuable your skills are.
It’s important to know the difference between rosy optimism and periods of chaos that trend upward.
If your expectations grow faster than your income you’ll never be happy with your money no matter how much you accumulate.
The inability to forecast the past has no impact on our desire to forecast the future. Certainty is so valuable that we’ll never give up the quest for it, and most people couldn’t get out of bed in the morning if they were honest about how uncertain the future is.
Having no FOMO might be the most important investing skill.
Few things are as valuable in the modern world as a good bullshit detector.
Most of what people call “conviction” is a willful disregard for new information that might make you change your mind. That’s when beliefs turn dangerous.
People have vastly different desires, except for three things: Respect, feeling useful, and control over their time. Those are nearly universal.
The market is rational but investors play different games and those games look irrational to people playing a different game.
There’s a sweet spot where you grasp the important stuff but you’re not smart enough to be bored with it.
A big takeaway from economic history is that the past wasn’t as good as you remember, the present isn’t as bad as you think, and the future will be better than you anticipate.
Most assholes are going through something terrible in their life. People hide their skeletons, which requires blind forgiveness of their quirks and moods because you’re unaware of what they’re dealing with.
History is driven by surprising events but forecasting is driven by obvious ones.
Pessimism always sounds smarter than optimism because optimism sounds like a sales pitch while pessimism sounds like someone trying to help you.
Every past decline looks like an opportunity and every future decline looks like a risk.
A comforting delusion is thinking that other people’s bad circumstances couldn’t also happen to you.
For many people the process of becoming wealthier feels better than having wealth.
Something can be factually true but contextually nonsense. Bad ideas often have at least some seed of truth that gives their followers confidence.
Every market valuation is a number from today multiplied by a story about tomorrow.
Comedians are the only good thought leaders because they understand how the world works but they want to make you laugh rather than make themselves feel smart.
People learn when they’re surprised. Not when they read the right answer, or are told they’re doing it wrong, but when they experience a gap between expectations and reality.
People tend to know what makes them angry with more certainty than what might make them happy. Happiness is complicated because you keep moving the goalposts. Misery is more predictable.
Getting rich and staying rich are different things that require different skills.
Money’s greatest intrinsic value is its ability to give you control over your time.
Past success always seems easier than it was because you now know how the story ends, and you can’t unremember what you know today when trying to remember how you felt in the past.
“Learn enough from history to respect one another’s delusions.” -Will Durant
There’s more to learn from people who endured risk than those who seemingly conquered it, because the kind of skills you need to endure risk are more likely repeatable and relevant to future risks.
Nothing too good or too bad stays that way forever, because great times plant the seeds of their own destruction through complacency and leverage, and bad times plant the seeds of their own turnaround through opportunity and panic-driven problem-solving.
Most people can afford to not be a great investor. But they can’t afford to be a bad investor.
What money can and can’t do for you isn’t intuitive, so most people are surprised at how they feel when they suddenly have more or less than before.
Your personal experiences make up maybe 0.00000001% of what’s happened in the world but maybe 80% of how you think the world works.
Unsustainable things can last longer than you anticipate.
“The thing that is least perceived about wealth is that all pleasure in money ends at the point where economy becomes unnecessary. The man who can buy anything he covets, without any consultation with his banker, values nothing that he buys.” - William Dawson
Napoleon’s definition of a military genius was “The man who can do the average thing when everyone else around him is losing his mind.” It’s the same in business and investing.
It’s hard to tell the difference between boldness and recklessness, greed and ambition, contrarian and wrong.
Woodrow Wilson talked about whether something was accountable to Darwin or accountable to Newton. It’s a useful idea. Everything is accountable to one of the two, and you have to know whether something adapts and changes over time or perpetually stays the same.
Risk has two stages: First, when it actually hits. Then, when its scars influence our subsequent decisions. The recession, and the lingering pessimism that does as much damage.
Tell people what they want to hear and you can be wrong indefinitely without penalty.
Optimism and pessimism always overshoot because the only way to know the boundaries of either is to go a little bit past them.
Reputations have momentum in both directions because people want to associate with winners and avoid losers.
It’s easier to lie with numbers than words, because people understand stories but their eyes glaze over with numbers. As the saying goes, more fiction has been written in Excel than Word.
It’s easy to take advantage of people. It’s also easy to underestimate the power and influence of groups of people who have been taken advantage of for too long.
You have five seconds to get people’s attention. Books, blogs, emails, reports, it doesn’t matter – if you don’t sell them in five seconds you’ve exhausted most of their patience.
It always looks like we haven’t innovated in 10 or 20 years because it can take10 or 20 years before an innovation is an obvious success.
When and where you were born can have a bigger impact on your outcome in life than anything you do intentionally.
Most people are good at learning facts but not great at learning rules – the broad lessons from events that will apply to future events.
Everyone is making a bet on an unknown future. It’s only called speculation when you disagree with someone else’s bet.
There are two types of information: stuff you’ll still care about in the future, and stuff that matters less and less over time. Long-term vs. expiring knowledge. It’s critical to identify which is which when you come across something new.
The same traits needed for outlier success are the same traits that increase the odds of failure. The line between bold and reckless is thin. So be careful blindly praising successes or criticizing failures, as they often made similar decisions with slightly different levels of luck.
When communicating, “know your audience” easily becomes “pander to your audience.”
Most financial mistakes come when you try to force things to happen faster than is required. Compounding doesn’t like when you try to use a cheat code.
There is an optimal net worth for most people, after which not only does happiness stop increasing but more money becomes a social and psychological liability. The number is different for everyone, but is probably lower than most people think.
Risk is what you can’t see, think only happens to other people, aren’t paying attention to, are willfully ignoring, and isn’t in the news. A little surprise usually does more damage than something big that’s been in the news for months.
Innovation and economics can be miles apart. Twitter directly influences geopolitics between nuclear states and is worth half as much as Progressive Auto Insurance.
Risk management is less about how you respond to risk and more about recognizing how many things can go wrong before they actually do.
There is too much marketing (waving your arms) and not enough branding (building trust).
A lot of people don’t realize what bet they’re making. Maybe they thought they were betting on disruptive technology, but it turned out they were betting on low interest rates. Or they thought they were betting on alternative energy, but it turned out they were betting on subsidies and tax credits. Many bets don’t work not because your bet was wrong, but because you didn’t realize the bet you were making in the first place.
Housing is often a liability masquerading as a safe asset.
Asking what the biggest risks are is like asking what you expect to be surprised about. If you knew what the biggest risk was you would do something about it, and doing something about it makes it less risky. What your imagination can’t fathom is the dangerous stuff, and it’s why risk can never be mastered.
A lot of good writing makes points that people already intuitively know but haven’t yet put into words. It works because readers learn something new without having to expend much energy questioning whether it’s true. The alternatives are points that are obvious and well known (boring) or something that’s non-obvious and unknown (often takes too much effort to understand and impatient readers leave).
Emotions can override any level of intelligence.
Small risks are overblown because they’re easy to talk about, big risks are discounted and ignored because they seem preposterous before they arrive.
If you have an idea but think “someone has already done that,” just remember there are 1,010 published biographies of Winston Churchill.
No one is thinking about you as much as you are.
John D. Rockefeller was worth the equivalent of $400 billion, but he never had penicillin, sunscreen, or Advil. For most of his adult life he didn’t have electric lights, air conditioning, or sunglasses. Everything about wealth is circumstances in the context of expectations.
Read fewer forecasts and more history. Study more failures and fewer successes.
There is an optimal amount of bullshit in life. Having no tolerance for hassle, nonsense and inefficiency is not an admirable trait; it’s denying reality. Once you accept a certain level of BS, you stop denying its existence and have a clearer view of how the world works.
Most problems are more complicated than they look but most solutions should be simpler than they are.
About once a decade people forget that bubbles form and burst about once a decade.
If something is impossible to know you are better off not being very smart, because smart people fool themselves into thinking they know while average people are more likely to shrug their shoulders and end up closer to reality.
You can’t believe in risk without also believing in luck because they are fundamentally the same thing—an acknowledgment that things outside of your control can have a bigger impact on outcomes than anything you do on your own.
“Reality will pay you back in equal proportion to your delusion.” – Will Smith
Risk’s greatest fuels are leverage, overconfidence, ego, and impatience. Its greatest antidote is having options, humility, and other people’s trust.
Once-in-a-century events happen all the time because lots of unrelated things can go wrong. If there’s a 1% chance of a new disastrous pandemic, a 1% chance of a crippling depression, a 1% chance of a catastrophic flood, a 1% chance of political collapse, and on and on, then the odds that something bad will happen next year – or any year – are … pretty good. It’s why Arnold Toynbee says history is “just one damn thing after another.”
People suffering from sudden, unexpected hardship can adopt views they previously would have considered unthinkable.
It’s easiest to convince people that you’re special if they don’t know you well enough to see all the ways you’re not.
A large group of people can become better informed over time. But they can’t, on average, become more patient, less greedy, or more level-headed during periods of upheaval. That will never change.
Good ideas are easy to write, bad ideas are hard. Difficulty is a quality signal, and writer’s block usually indicates more about your ideas than your writing.
More people wake up every morning wanting to solve problems than wake up looking to cause harm. But people who cause harm get the most attention. So slow progress amid a drumbeat of bad news is the normal state of affairs.
Everything is sales.
2025-08-04 17:19:00
A few short stories:
The CEO of Bronco Wine – which sells the Charles Shaw “Two Buck Chuck” wine at Trader Joe’s – was once asked how he’s able to sell wine for less than the cost of bottled water.
He replied: “They’re overcharging you for the water. Don’t you get it?”
Franklin Roosevelt looked around the room and chuckled when his presidential library opened in 1941. A reporter asked why he was so cheerful. “I’m thinking of all the historians who will come here thinking they’ll find the answers to their questions,” he said.
Everything we know about history is limited to what’s been written down, shared publicly, or spoken into a camera. The stuff that’s been kept secret, in someone’s head, taken to the grave, must be – I don’t know – 1,000 times as large and more interesting.
Years before the Wright Brothers flew, scores of other entrepreneurs attempted to build an airplane, tinkering with different models to see what might work.
One was a German inventor named Otto Lilienthal. On one flight in August 1896, Lilienthal’s glider was 50 feet in the air when it suddenly dropped to the ground like a stone. Otto broke his neck.
He died the next day, just after uttering his final words, a dedication to the progress of his field: “Sacrifices must be made.”
Gabby Gingras was born unable to feel pain. She has a full sense of touch. But a rare genetic condition left her completely unable to sense physical pain.
You might think this is a superpower, or an incredible gift. But her life is dreadful. The inability to feel pain left Gabby unable to distinguish right from wrong in the physical world. One profile summarized a fraction of it:
As Gabby’s baby teeth came in, she mutilated the inside of her mouth. Gabby was unaware of the damage she was causing because she didn’t feel the pain that would tell her to stop. Her parents watch helplessly.
“She would chew her fingers bloody, she would chew on her tongue like it was bubble gum,” Steve Gingras, Gabby’s father, explained. “She ended up in the hospital for 10 days because her tongue was so swelled up she couldn’t drink.”
Pain also keeps babies from putting their fingers in their eyes. Without pain to stop her, Gabby scratched her eyes so badly doctors temporarily sewed them shut. Today she is legally blind because of self-inflicted childhood injuries.
Pain is miserable. Life without pain is a disaster.
The night before the D-Day Invasion, Franklin Roosevelt asked his wife Eleanor how she felt about not knowing what would happen next.
“To be nearly sixty years old and still rebel at uncertainty is ridiculous isn’t it?” she said.
The original Ford Model T had more than 100 square feet of wood in it. Multiplied by millions of cars, it was a tremendous amount of lumber and produced a tremendous amount of scrap wood and sawdust.
Henry Ford, ever the entrepreneur, wondered what he could do with the scraps. He settled on turning it into charcoal.
Thus began the Kingsford Charcoal company, which today – 110 years later – has an 80% market share in the barbeque market.
BlackRock CEO Larry Fink once told a story about having dinner with the manager of one of the world’s largest sovereign wealth funds.
The fund’s objectives, the manager said, were generational.
“So how do you measure performance?” Fink asked.
“Quarterly,” said the manager.
The gap between ideals and reality.
Robin Williams was a genius who understood how the world works better than most. He was also a terrible student. Sometimes those traits appeared together.
During a macroeconomic class at College of Marin, Williams’ final paper contained a single sentence to his professor: “I really don’t know, sir.”
He failed the class. But if you ask me, his answer is the highest level of economic wisdom.
Michael Lewis published his first book, Liar’s Poker, in 1989. It was a huge hit. But his next book didn’t come for another decade. He later explained his hiatuses and why he fills his time with hobbies:
Writers can get in this mindset where they feel they have to write another book … the publisher’s on you afterwards and they’re ready to get you going again. And I just always feel that the book is going to be better if I start all over again, start completely fresh as if I’ve never written a book before and give myself at least the option of not writing books.
The best ideas happen when you wait patiently for them to come, which isn’t something you or your boss can schedule.
JFK and Jackie Kennedy didn’t have a great marriage. In 1955, two years after their marriage, Jack told his father, Joe Kennedy, he wanted a divorce.
Joe responded: “You’re out of your mind. You’re going to be president someday. This would ruin everything. Divorce is impossible.”
Jack reiterated that he and Jackie weren’t happy.
His father shot back: “Can’t you get it into your head that it’s not important what you really are? The only important thing is what people think you are!”
The first cars started showing up in American cities in the late 1800s. Not everyone was thrilled. In 1896, Washington DC banned cars on the grounds that they threatened the livelihoods of horses. The Washington Post reported:
The commissioners of the District of Columbia are determined that the horse whose occupation has so largely been taken away by reason of the use of bicycles shall not further be displaced by horseless carriage.
Change is hard.
Part of the Armistice that ended World War I forced the dismantling of Germany’s military. Six million rifles, 38 million projectiles, half a billion rounds of ammunition, 17 million grenades, 16,000 airplanes, 450 ships, and millions of tons of other war equipment were destroyed or stripped from Germany’s possession.
But 20 years later, Germany had the most sophisticated army in the world. It had the fastest tanks. The strongest air force. The most powerful artillery. The most sophisticated communication equipment, and the first missiles.
A catastrophic irony is that this advancement took place not in spite of, but because of, its disarmament.
George Marshall, U.S. Army Chief of Staff, noted:
After the [first] World War practically everything was taken away from Germany. So when it rearmed, it was necessary to produce a complete set of materiel for the troops. As a result, Germany has an army equipped with the most modern weapons that could be turned out. That is a situation that has never occurred before in the history of the world.
There’s a set of advantages that come from being endowed with resources. There’s another set of advantages that come from starting from scratch. The latter can be sneakingly powerful.
Ulysses S. Grant’s wife, Julia, did not like Abraham Lincoln’s wife, Mary.
When President Lincoln asked Grant to accompany him and the First Lady to Ford’s Theater on April 15th, 1865, Grant declined, joking with the president that it was a command from his wife that he stay home. Lincoln responded:
“Of course, General, you have been long from home, fighting in the field, and Mrs. Grant’s instincts should be considered before my request. I am very sorry, however, for the people would only be too glad to see you.”
Lincoln was shot hours later.
Historian Ron Chernow writes:
Grant would long wonder if his presence at Ford’s Theatre might have altered things and whether Julia’s dislike of Mary Lincoln had inadvertently modified the direction of American history.
Would Grant, with his acute battlefield instincts, have sensed the assassin’s tread? Would he have been more attentive to security concerns and brought his own security guard? Would the omnipresent [aide] Beckwith have sat outside the box, buffering his boss from harm?
So much important history hangs by a thread.
The Chris Rock I see on Netflix is hilarious, flawless. The Chris Rock that performs in dozens of small clubs each year is just OK. No one is so good at comedy that every joke they write is funny. So every big comedian tests their material in small clubs before using it in big venues. Rock explained:
When I start a tour, it’s not like I start out in arenas. Before this last tour I performed in this place in New Brunswick called the Stress Factory. I did about 40 or 50 shows getting ready for the tour.
One newspaper described Rock at the Stress Factory fumbling with material to an indifferent audience. “I’m going to have to cut some of these jokes,” he says mid-skit.
That isn’t bad; he’s still a genius.
But all success is like an iceberg: what most of us see is a fraction of what happened. And it’s stripped of all the hard parts.
President Clinton noted in his January 2000 State of the Union speech:
We begin the new century with over 20 million new jobs; the fastest economic growth in more than 30 years; the lowest unemployment rates in 30 years; the lowest poverty rates in 20 years; the lowest African-American and Hispanic unemployment rates on record; the first back-to-back surpluses in 42 years; and next month, America will achieve the longest period of economic growth in our entire history.
That wasn’t an exaggeration. But it marked the beginning of the worst decade for the stock market in modern times.
In January 2010, President Obama noted in his State of the Union speech:
One in 10 Americans still cannot find work. Many businesses have shuttered. Home values have declined. Small towns and rural communities have been hit especially hard. And for those who’d already known poverty, life has become that much harder.
That wasn’t an exaggeration. But it marked the beginning of one of the best periods for the stock market in modern times.
Gallup has been asking Americans for more than four decades, “Are you satisfied with the way things are going in the U.S. right now?”
The average percent of Americans answering “no” since 1969 is 63%.
What’s interesting is that Gallup asks a follow-up question: “Are you satisfied with the way things are going in your own life right now?”
There, the average “no” response is just 15.8%.
People tend to be optimistic about themselves but pessimistic about others. Social media probably supercharges that. Benedict Evans says, “The more the Internet exposes people to new points of view, the angrier people get that different views exist.”
2025-07-25 01:20:00
Is Ferrari a car company?
The obvious answer is yes, but not according to its CEO, Benedetto Vigna, who recently described the company’s business model saying,
“We are not – we are not – a car company. We are a luxury company that is also doing cars.”
That’s their differentiator. Their brand. Their “schtick.” And, it works, but not because it’s a marketing ploy. It works because Ferrari backs it up with its actions.
How so?
By adhering to its founder Enzo Ferrari’s “scarcity dictum” that declares,
“Ferrari will always deliver one car fewer than the market demands.”
Delivering one fewer than the market demands —
How many businesses can say they do that?
In my experience, very few. In fact, many do precisely the opposite.
Why?
Because more is almost always considered better. Size, scale, and growth are seductive. It is what attracts new investors and fresh capital. It is what grabs attention and headlines.
The trouble is that size and growth isn’t necessarily synonymous with strong performance.
Look no further than the past five years in the auto industry.
From 2020 to 2024, Ferrari sold fewer than 60,000 cars, but for an average price of over $450,000.
Now compare that with two of the largest car companies in the world by sales and revenue. Since 2020, Toyota has sold more than 52 million cars at an average price of $32,000. Meanwhile GM sold close to 30 million at an average price of $51,000.
As a result, while these behemoths have produced revenue north of a trillion dollars versus Ferraris of less than $30 billion, Ferrari’s net margins have been significantly higher at close to 23% last year versus an average of less than 6% for Toyota and GM.
The gap is even more pronounced on a gross margin basis.
The result has been drastically different stock price performance, as seen in the chart below (RACE = Ferrari, TM = Toyota, and GM = General Motors). Margins matter.
This isn’t limited to the auto industry. In fact, we see it everywhere from retailers to banks to technology companies, among others. Each is littered with failed growth stories, from Abercrombie and Under Armour, to Lehman Brothers and Countrywide, to GoPro, Clubhouse, and Peloton.
Most recently Burberry, the once iconic British fashion company, admitted that it too had fallen victim to unbridled pursuit of global growth. In doing so, it diluted its luxury image by becoming ‘too everywhere,’ which is why its new CEO is currently unwinding many of its most ambitious detours and refocusing on what built the brand. In his words, he wants to “lean into the assets that we already have and celebrate who we are.” Said another way, he wants to return to the Ferrari model.
If so, why don’t more companies follow Ferrari’s lead? Because as J.P. Morgan CEO, Jamie Dimon, is quoted as saying,
“CEO’s feel this tremendous pressure to grow. The problem is that sometimes you can’t grow. Many times, you don’t want to grow because growth can force you to take on bad customers/clients, excess risk, or excess leverage.”
Yet today, the euphoria surrounding growth, scale, and size is palpable. It’s practically all anyone talks about.
Every company wants to be classified as hyper-growth because doing so garners the highest valuations and attracts the most attention. To achieve this, many companies are chasing markets with massive total addressable markets (aka “TAMs”) and limitless opportunities. They prioritize scale and size over everything else. The trouble though, as Bill Gurley of Benchmark Capital recently highlighted, is that this has led to a dynamic akin to a “gavage.”
Never heard of a gavage?
Neither had I, but apparently it is the tube the French use to force-feed ducks to create foie gras.
Today, venture capital firms are doing something similar, but instead of force-feeding ducks with food, they are force feeding companies with capital. In doing so, this is forcing companies to invest in areas outside their circle of competence, hire people to sell products that aren’t ready for “go to market,” and to lose discipline more broadly. In Gurley’s words on a recent podcast titled “The Gift and Curse of Staying Private,”,
“It is forcing every company to go ‘all or nothing’ and ‘swing for the fences.’ It is no longer your grandfather’s startup business or your grandfather’s venture capital fund. It is a radically different world. And if you are a founder, you would like to be able to ignore all of it and build your company the way you want to build it. But if your competitor raises $300 million and is going to 10x the size of their sales force, or 50x it, you will be dead before you know it. You won’t be around. I think it’s bad for the ecosystem because it will remove all the small and middle outcomes and force businesses to just play grand slam home runs. But that’s what it feels like to me. And it feels like we didn’t learn anything from the days of 0% interest rates.”
Unsurprisingly, if this forced feeding of capital is causing companies to be less disciplined in how they allocate capital, there will undoubtably be a negative downstream effect on the venture and private equity funds that are backing them. In fact, we may already be seeing this in the form of diminishing returns and lower liquidity.
Amazingly though, even with the private markets already awash in capital, we are about to witness an even larger inflow in the form of individual investor capital. Look no further than the recent WSJ article titled, “Why Vanguard, Champion of Low-Fee Investing Joined the ‘Private Markets’ Craze,” that highlights how the champion of passive investing has been seduced into the world of alternatives.
Vanguard is far from alone though as KKR recently announced a partnership with the mutual fund complex, The Capital Group, in order to expand its alternative offerings to “non-accredited” investors. Meanwhile, Charles Schwab announced that it is entering the alternatives world in a meaningful way by advocating that they will be incorporated into its 401k and individual investor platforms.
This is nothing new for investors though. It happened to mutual funds in the 1980’s after the advent of the 401k, hedge funds in the early 2000’s following the dot.com collapse, emerging markets after a brutal stretch for U.S. stocks, real estate funds heading into the GFC, and energy funds when commodity prices spiked more than a decade ago. In each case, too much capital proved to be a drag on performance.
Venture capital, and potentially private equity more broadly, will likely be the next victim.
So, what should an investor do?
The simple answer might be to “avoid private equity all together,” but that’s too simplistic and short-sighted. To me, that answer feels like the equivalent of giving up on investing in retail companies all together because Burberry, Under Armour, and Abercrombie overplayed their hands. Afterall, if you did this, you would have missed the Hermes, CostCo’s, Ross Store’s, and Monster Beverage’s of the world.
As a result, it feels like the better course of action is to pursue the funds that aim to achieve Ferrari status. Those that have maintained the discipline to, in Enzo Ferrari’s words, “deliver one fewer (investment or fund) than the market demands,” while avoiding those that have gotten seduced by growth at all costs.
This said, it also feels like there might be even more unique opportunities, especially in the public markets, but that is for a future post.
2025-07-10 21:52:00
Recently, I had lunch with Emmett Shine, co-founder of Gin Lane and a thoughtful voice in the conversation around AI and design.
Among other things, we talked about the future of user interfaces and experiences in an AI-driven world. He said something that really stuck with me: “humans existed without screens for hundreds of thousands of years. They will exist without screens for hundreds of thousands more.”
Increasingly, I envision a world without phones or tablets or computers. A world defined by a more immersive, primarily hands-free technological experience. A future where our children will view screens the way most of us view cigarettes. “You used to look at a screen all day?” they’ll say. “Do you know how bad that is for you?”
Meta and OpenAI clearly envision this reality, too.
Meta has invested hundreds of billions of dollars into AR/VR headsets, Ray-Ban smart glasses, a neural interface wristband, and even holographic wearables.
OpenAI announced a $6.5 billion deal with Jony Ive to create an AI device that can unseat the smartphone.
Though screens remain ubiquitous, they’re already beginning to feel outdated. It’s a clunky, poor user experience for accessing the power of AI.
What does a screenless future mean for tech? To reach a truly screenless future, we’ll likely need three things: new hardware, more natural voice dictation, and a step change in motion detection. (Or, possibly, mind reading…but let’s not get ahead of ourselves. We’ll leave that to Elon.)
In the past few months, we’ve seen a flurry of startups in all three categories.
Stealth Hardware: The dream of a magical AI-powered pin still lives on, if only in concept for now. In addition to Meta and OpenAI, a number of startups have begun to explore devices that feel as natural as jewelry or clothing, and less like a mini smartphone strapped to your chest.
Genuine Voice: The days of “Sorry, I didn’t catch that” are numbered. Berlin’s Synthflow just raised $20 million to power AI agents that hold real-time conversations with sub-400 millisecond response times. Wispr Flow just announced a $30M round for their AI-dictation app (it works like a dream). During WWDC, Apple focused on their new Apple Intelligence features and highlighted improvements in voice. And, YC put out an RFP for voice technologies ahead of their Spring 2025 batch. It might seem like the die has already been cast, but there is still plenty of space for winners who focus on nuance like intonation, turn-taking, and empathy. Because the moment you think “voice is solved,” a better product will win.
Human-Level Motion Detection: Motion sensing has matured past rudimentary gesture controls. Ambient.ai has raised north of $50 million to deliver near-human perception in physical spaces. Imagine a watch that can sense gestures, like a wave, to lock your front door.
Together, these innovations form the skeleton of a screenless UX. Design is what will flesh out that vision.
What does a screenless future mean for design? Take the screen away and what’s left is tone: cadence, empathy, restraint. Personality becomes the new product. In a market where models and APIs commoditize by the quarter, trust still compounds the old-fashioned way: one human reaction at a time. Brand DNA becomes a moat not because it looks pretty, but because it behaves: saying sorry before it’s asked, cracking the joke that defuses anxiety, staying silent when silence feels like respect.
What does a screenless future mean for you? Our collective sci-fi vision of the future often features a sea of blinking lights and fluorescent screens in classics from Blade Runner to The Jetsons.
But there’s a peaceful quality to technology fading into the background. Counterintuitively, even if technology becomes ubiquitous, if it is also virtually invisible, it gives us space to get back to a life that is a little more, well, human.
Mark Weiser once wrote, “The most profound technologies are those that disappear. They weave themselves into the fabric of everyday life until they are indistinguishable from it.”
As AI makes that reality possible, the most powerful technology won’t demand our attention. It will give it back to us.
2025-06-27 21:05:00
First came the foundation models. Then the enterprise tools. Next comes the consumer wave: millions of tiny daily decisions, habits, and purchases getting rerouted through AI.
But how do you build with a giant, dynamically generated, shadow looming over you?
OpenAI has a formidable head start. And it’s not just massive…it’s everywhere. ChatGPT is likely to reach over 1 billion monthly users before the end of the year. In other words, nearly 1 out of every 5 adults across the world will be be interacting with Altman’s chatbot.
Giants tend to win by default, particularly in consumer applications where gravity is critical for building network effects. In the early 2000s, Google steamrolled everything from AltaVista to Yelp to MapQuest. But even Google couldn’t crack social (remember Google+?) or build an e-commerce engine to rival Amazon (how about Google Express?). Dominance in one vertical (even a massive one like search) doesn’t guarantee success everywhere else.
The opening exists where generalists can’t or won’t go deep. Here’s where consumer AI founders should build now:
**Complex, regulated industries**
Healthcare, taxes, insurance, real estate: these markets don’t reward “good enough answers” — they demand liability coverage, workflow integration, and regulatory compliance. Take the FDA’s AI/ML Software-as-a-Medical-Device framework: it requires pre-specified change control protocols, lifecycle oversight, and algorithmic transparency. That transforms OpenAI’s “ship fast” advantage into a liability.
This regulatory moat is why vertical specialists can win even while using OpenAI’s models underneath. Yes, OpenAI offers BAAs and enterprise privacy controls now, but compliance infrastructure isn’t just about data handling, it’s about audit trails, clinical validation, and regulatory relationships built over years.
You probably wouldn’t trust ChatGPT to file your taxes or dispute chargebacks on your credit card. And that’s good, because OpenAI doesn’t want to handle those risky workflows either.
**Bridging digital and physical worlds**
The next consumer breakthroughs won’t live in a chat window. They’ll orchestrate contractors, manage inventory, coordinate delivery windows, and handle angry customers calling at 9 PM. This operational complexity is OpenAI’s kryptonite.
Owning the last mile creates defensibility because it absorbs messy, real-world problems that general platforms avoid. This applies to everything from travel and hospitality to healthcare, homebuilding, and sports.
Doctronics is a good example. You might look to ChatGPT for general health advice, but are you going to trust it to diagnose that strange mole or handle a crucial insurance claim? At first blush, the Doctronics experience feels like any other chatbot — but the genius (and the reason ChatGPT won’t be able to compete with them) — is in the final step: AI triage leads to a telehealth session and, maybe, even in-person care if needed.
**Hardware with conviction**
OpenAI clearly eyeing hardware opportunities. But hardware remains brutal terrain, even for tech giants. Google needed acquisitions like Nest and Fitbit to go deeper into physical products, and most failed anyway. Meta, Amazon, and Microsoft have all poured billion into hardware, but still lead with software.
The opening for startups is specificity. A focused team building opinionated devices around a single, obsessive use case has room to run. While OpenAI optimizes for general intelligence, great hardware demands specific intelligence — the kind that comes from understanding exactly how people will hold, carry, and live with your product. WHOOP and Oura show the pattern in personal health: a tight loop from sensor to insight to behavior, repeated until it becomes an unshakeable habit.
I recently learned of a hardware concept in hospitality that adapts a restaurant or hotel experience based on your personal preferences. I’m eager to see other ways that hardware and software interplay in this next phase of AI, and particularly excited to see how new entrants approach wearables and integrated devices to finally divorce us from our screens.
**Creative tools that amplify taste**
OpenAI is not creative. No LLM demonstrates genuine originality: they remix and recombine existing patterns. As much fear exists around AI displacing creatives, the reality is that AI will become the most powerful creative tool ever invented.
The opportunity isn’t in replacing human creativity; it’s amplifying it. This requires understanding not just what creators make, but how they think, iterate, and collaborate. Approximately 1,000 thought pieces have been written this year about the importance of taste (I know, because I wrote one); but it’s true — foundation models can’t learn taste from training data alone.
This is why we launched AIR, a Brooklyn residency for founders building at the intersection of design and AI. We believe creatives will need to take the wheel in imbuing AI startups with creativity. And, let’s face it, Sam Altman is not known for his creativity or design instincts (the naming conventions at ChatGPT alone decry a lack of brand know-how).
******
OpenAI might own the majority of the consumer AI experience, but there’s plenty of room for new entrants to succeed, The lesson from history is clear: giants harvest the averages, but startups win the edges.
2025-06-26 01:31:00
Lately, it feels like every corner of my internet bubble is talking about venture returns—Carta charts one day, leaked DPI tables the next. I’ve seen posts on lagging vintages, mega-fund bloat, the “Venture Arrogance Score”, the rising bar for 99th‑percentile exits, and the PE-ification of VC.
But for all that noise, I haven’t seen much that actually walks through how returns metrics evolve over time in an early-stage fund. That’s a crucial gap. Many analyses focus on funds that are still mid-vintage, where paper markups can tell an incomplete or even misleading story.
So I pulled the numbers on Collaborative’s first fund, a 2011 vintage that’s now nearly fully realized. It offers a concrete look at how venture performance can unfold across a fund’s full lifecycle.
Fund 1 was small: $8M deployed across 50 investments. Check sizes ranged from ~$10K to ~$400K, averaging around $100K for both initial and follow-on rounds. It was US-focused, sector-agnostic, and mostly pre-seed through Series A.
Without further ado, here’s how the fund performed over its lifetime across a few core metrics:
Note: Distributions are net to LPs; contributions reflect paid-in capital. IRR data was not meaningful (“NM”) for years 1–5.
Below is a line chart of the returns data:
Note: IRR is shown as a dashed line corresponding to the secondary axis.
Contributions wrapped up by year 4, which is typical for early-stage funds. Distributions didn’t start until year 4 and peaked around year 10:
Returns were highly concentrated. Eight companies—Upstart, Lyft, Scopely, Blue Bottle Coffee, Maker Studios, Gumroad, Reddit, and Kickstarter—drove nearly all distributions.
Note: “Cost” is cumulative capital actually invested. “Cash Back” is cumulative proceeds received by the fund from realization events, and excludes (i) any remaining unrealized value and (ii) fund-level fees and expenses. “Multiple” is the quotient of Cash Back divided by Cost.
Together, these accounted for just $0.8M of invested capital but returned $37.6M—an average multiple of 45x. The remaining 42 investments, representing $7.2M, returned only $2.0M (a 0.3x multiple).
Within those eight, outcomes varied widely: one company alone delivered 73% of all cash returned. Adding the next three brought the cumulative share past 90%. Multiples ranged from 1.4x to 115x—illustrating just how concentrated and variable even a “winning” subset can be.
We believe the biggest risk in early-stage VC isn’t failure. It’s missing (or mis-sizing) the outlier. In Fund I, eight companies drove nearly all distributions. One check alone accounted for more than 70% of DPI. This is the power law at work.
Collaborative’s story now spans 15 years with four early funds in harvest mode. Three rank in PitchBook’s top quartile with two in the top decile by DPI. In each, a small number of companies drove the bulk of returns. Perhaps these will make for future posts.
Until then, I hope this serves as a reminder to take venture performance narratives based on unrealized funds with a grain of salt. Some trends are real and worth watching. But many of the loudest signals may fade or reverse as funds mature. Until they’re fully played out, their stories are still being written.
