2026-06-11 02:03:00
Why we misunderstand odds and why it matters
Everyone has a weakness. A blind spot. A vulnerability.
For Achilles, it was his heel. Superman had kryptonite. Ted Williams struggled with pitches low and away.
But what about the average person?
I often think our Achilles heel is our inability to understand probabilities. And increasingly, it’s making us more stressed than ever.
I was reminded of this recently after speaking with a young man who is navigating the college admissions process. He had been accepted to several very good universities, but not his first choice, which happens to accept fewer than 6% of applicants.
In an attempt to alleviate some of his angst, I asked him a simple question:
“How many high schools do you think there are in the United States?”
He guessed 12,000.
The actual number is closer to 25,000.
I then asked him how many valedictorians there are in the U.S.
He understood the point. Roughly one valedictorian at each high school, so 25,000 in total.
Considering that the Ivy League enrolls approximately 15,000 freshmen each year, in theory, 40% of all valedictorians don’t have a spot. Once you account for international students, even fewer do.
Yet every year, students and parents across the country are devastated by rejection letters from elite universities.
This phenomenon isn’t limited to college admissions. It shows up practically everywhere. Companies, marketers, and advertisers know it and often exploit it.
Youth travel programs charge thousands of dollars and promise pathways to scholarships and college admissions despite the long odds.
Sports franchises convince us to invest our hearts and wallets every season despite the tiny probability of winning a championship. (As a long-suffering Washington Commanders fan, I can personally attest to this.)
Investment managers pitch market-beating strategies despite the fact that most fail to outperform the S&P 500 over time.
Which reminds me of a story involving Charlie Munger.
Munger once asked an investment manager what annual returns he promised clients.
“Twenty percent,” the manager replied.
“Twenty percent annually is impossible,” Munger shot back.
The manager shrugged.
“Charlie, if I told them a lower number, they wouldn’t give me any money to invest.”
So what’s the solution? Should we all have paid closer attention during the probability chapter in high school math?
When I began writing this piece, I would have answered with an unequivocal yes.
Then something occurred to me.
Ironically, our greatest weakness may also be one of our greatest strengths.
After all, how else do you explain entrepreneurs starting companies in garages, explorers venturing into the unknown, or America’s Founding Fathers risking everything to declare independence from Great Britain?
Viewed purely through the lens of probability, many of humanity’s greatest achievements look irrational.
No rational calculation alone would have inspired those leaps.
Something else was required.
But what?
Passion.
And that leaves us with an interesting tension.
When should we trust the odds, and when should we challenge them?
When the pursuit matters as much as the outcome.
If you love learning, study hard. Chase your dream school. Take the APs and advanced classes. But if the acceptance letter never comes, your efforts will not have been in vain. The education you gain and continue building throughout your life will matter far more than the name at the top of your diploma.
If you pour countless hours into a sport you love, but never earn a scholarship, it won’t have been a waste. You will have experienced victory and defeat, learned what it means to be a good teammate, and chased a dream.
Your favorite team may never win a championship, but the memories of rooting for them will last a lifetime.
And if an investment you believed in fails, you will have learned a lesson every successful investor eventually does: even the best are wrong much of the time.
The key is understanding why you’re doing something.
If you’re chasing a dream because you genuinely love the pursuit, the odds matter less.
If you’re doing it solely for status, recognition, or some promised outcome, disappointment is almost inevitable.
My takeaway?
Understanding probabilities is essential for maintaining perspective in a world filled with unrealistic expectations and carefully curated success stories.
But if you find something you truly love, don’t let the odds become your Achilles heel.
Instead, understand the probabilities, then decide whether the dream is worth pursuing anyway. And when others choose to chase theirs, root for them too.
After all, many of humanity’s greatest achievements began with someone willing to pursue a dream despite the odds.
2026-05-20 03:35:00
What defines Collab Holdings future success isn’t the capital; it’s the stewardship.
Few investors understand both the rigor of private equity and the nuance of what makes a brand actually matter to people. Parker Hayden does, and he is joining Collaborative Fund as a Partner to lead Collab Holdings.
Collab Holdings exists to be a home for enduring companies, and Parker is the right person to lead that work.
Over more than two decades, Parker has deployed over $3 billion across dozens of transactions. His track record includes investments in some of the most culturally significant consumer brands, among them Supreme, Beats by Dre, CAVA, OGX, and 66° North. He has served on more than 15 boards and has handled everything from sourcing through exit, including public offerings and strategic sales.
Before joining Collaborative, Parker oversaw the portfolio at Redesign Health. Prior to that, he led direct investing at Mousse Partners. He spent more than a decade at The Carlyle Group on the Consumer and Retail U.S. Buyout team and began his career at Morgan Stanley.
At Collaborative, we look for partners who recognize that the best businesses are built for the long term. Parker’s track record as an investor and a board member speaks for itself.
We’re glad to have him.
2026-04-15 19:00:00
A few months ago I was in Northern California, visiting a company we’ve known for years. They make one product. They’ve made it the same way for decades. Their customers are borderline religious about it. The business is profitable, growing steadily, and has been for a long time.
Over dinner, the founder told me something I’ve now heard in some version from at least a dozen founders over the past fifteen years.
“I have investors who need to sell. I don’t want to sell. And there’s no one in the middle.”
She didn’t want to go public. She didn’t want to get rolled up by private equity. She didn’t want a strategic acquirer who’d strip the thing down to a margin optimization exercise. She just wanted to keep building the company she’d already built, with a partner who saw the same horizon she did.
I didn’t have a great answer for her. Not yet.
I think about this problem a lot, partly because it keeps showing up, and partly because the conditions that created it are getting worse.
Right now, an enormous amount of capital is flowing toward AI. That makes sense. The technology matters and the opportunity is real. We’re investors in AI ourselves. But one consequence of that concentration is that a whole category of great businesses is being quietly starved of the right kind of capital.
These are companies that make real, physical products people love. Products you can hold, taste, wear, give to someone you care about. They tend to be profitable. They tend to have customer bases that behave less like “users” and more like communities. And they tend to be run by founders who measure their work in decades, not funding rounds.
You know these companies when you encounter them. You probably own their products. A cast iron pan you’ll pass down. A pair of socks guaranteed for life. A soap that’s been made the same way since your grandparents were alive. A bag built to outlast you. They don’t chase trends. They set a standard and hold it, year after year, until the standard becomes the identity.
If you were starting LVMH today — not as a luxury conglomerate, but as a home for brands built on craft, obsession, and generational loyalty — what would it look like?
That question has been rattling around my head for a while. It’s what led us to build Collab Holdings.
Collaborative Fund has spent fifteen years backing companies at the intersection of strong values and strong economics — Blue Bottle, Sweetgreen, Kickstarter, OLIPOP. The thesis has always been the same: companies that align what’s good for people with what’s good for business tend to outperform over time.
But venture capital, even mission-aligned venture capital, has a structural limitation: the clock. A ten-year fund needs liquidity on a ten-year timeline. For software companies growing at triple-digit rates, that works. For a beloved consumer brand growing steadily with healthy margins and fanatical customers, it can be a slow-motion disaster. The fund timeline kicks in, and suddenly there’s pressure to juice growth, dilute the product line, “explore strategic alternatives.” The thing that made the company great becomes the thing that gets sacrificed.
There’s a real gap in the capital stack, and we think we can fill it.
Collab Holdings is a new private equity strategy, purpose-built to be a long-term home for extraordinary consumer brands. No forced exits. No ten-year clock. Success measured by cash flow and customer devotion, not by how quickly we can engineer an exit.
This isn’t a roll-up. We’re not consolidating brands under one umbrella to extract synergies. We’re looking to partner with founders who’ve already built something they’re proud of and give them the capital structure to keep doing it; for five years, ten years, thirty years.
We think the best brands are built by people who refuse to compromise. Who understand that the most valuable thing they own isn’t their revenue — it’s the relationship they have with the people who buy their products. Who believe that protecting what makes something great is how you make it last — and that making it last is how you make it enormous.
Historically, that conviction hasn’t had a capital partner that matches it.
Last month, I came across a letter Warren Buffett wrote to the president of See’s Candy in 1972. He’d just bought the company for $25 million. It’s produced billions in profit since — not because he optimized it, but because he understood what it was and gave it room to be that thing for a very long time.
That’s the instinct behind Collab Holdings. We want to be the kind of partner who understands what a company is — and gives it the room and the capital to keep being that, on its own terms, for as long as the founders want to build it.
If you’re building something like this — a company your customers love in a way that spreadsheets can’t quite capture — we’d love to hear from you.
Please meet: collab.holdings
2026-04-03 00:30:00
Adam Smith, the 18th century economist, wrote that it’s not uncommon to meet a mother in the Scottish highlands “who has born twenty children not to have two alive.”
That was life. And it hardly mattered whether you were rich or poor. Queen Anne of England had 18 children, not a single one of whom made it to adulthood. American president James Garfield died in 1881 in part because the best doctor in the country was not yet a believer in germs. Two weeks before his death, Franklin Roosevelt’s blood pressure was 260/150, and his doctors could hardly do a thing; basic blood pressure medicine didn’t exist.
If you could show any of these people a modern grocery store, they would faint from disbelief. They could not comprehend that the biggest challenge of grocery shopping is deciding which of the 19 brands of jelly to buy, or that in January you can buy papayas in Minnesota. But most shocking would be the pharmacy in the back, which they would find magical.
And what would their response be?
I don’t think it would be, “You are so amazing.”
It would be along the lines of, “You are so spoiled.”
They would watch us getting frustrated at having to wait in line at the pharmacy and scoff at how unappreciative we are for the magic pills that await us.
They couldn’t fathom that we complain about the price of food rather than being gobsmacked at the mere possibility of abundance.
The irony is that every generation toils and innovates to create a more prosperous world for their heirs. But when you watch those future generations interact with their world, your feelings can shift from pride to disappointment. Our kids won’t suffer in the same ways we did, and they won’t even appreciate it.
It’s a common problem. Wealthy families wonder how they can support their kids without them becoming spoiled brats. Whole societies have a long history of feeling disappointed in youngsters who look lazy and entitled relative to their elders.
I’ve been thinking about this as I contemplate money and my own children. Here’s where I’ve landed.
I had a conversation with a guy a few months ago whose immigrant parents came to America and worked tirelessly in low-wage jobs to make ends meet.
Those kids are now adults, and this guy – as I understood it – felt a sense of shame that as a college-educated white-collar worker he would not have to suffer the same way his parents did for him. His parents instilled in him the lessons of frugality and grit. Would his own children learn the same from him if they watched their father live a comparatively easy life?
He gave an example: when he was a kid, all books were borrowed from the library. Now his young daughter demands (and gets) to purchase $15 Taylor Swift books that pile up in her room.
My response was that if we talked to his immigrant parents, I would bet they would say: that was the goal.
The entire reason they worked so hard was to catapult the family’s standing to a point where one generation must grind to get food and the next can indulge in Taylor Swift books. The granddaughter’s spoiled appearance is not a side effect of wealth; it was the goal.
To put it differently: The goal of some parents is to work so hard that their kids and grandkids get to live a life that appears spoiled by the standards of previous generations.
Like wealth, there is no objective definition of what counts as spoiled – everything is just relative to someone else.
I can look at my own kids and see how spoiled they are relative to my own childhood.
But couldn’t my grandparents do the same for me? They had to worry about polio, scarlet fever, and a host of other things that never cross my mind.
And couldn’t their own grandparents do the same? Their transportation was limited to horses, and a bad crop could mean losing some of your children – a life inconceivable just a generation or two later.
What’s common to miss here is that when one generation’s life becomes comparatively easier than before, their life does not become objectively easy; they just move on to worrying about higher-order problems that were previously deemed not urgent enough to worry about.
One generation worries about how to get food and shelter.
The next doesn’t have to worry about food and shelter but frets about security.
The next has security but worries about disease.
The next tackles disease but worries about education.
The next gets education but worries about work-life balance.
On and on. It’s the classic John Adams line, which I’ll paraphrase: “I studied war so my kids will have the liberty to study engineering. They will study engineering so their kids can have the liberty to study philosophy, whose kids can have the liberty to study art.”
I hope my kids and grandkids won’t have to worry about cancer in the ways we do. I hope they have incredible technology that makes their jobs easier than ours. I hope that everyday frictions we deal with today disappear. I hope their energy is so abundant they consider it unlimited.
Is that spoiled? I suppose, but when you frame it like that you might think of a different word – perhaps “lucky,” or, “fortunate.”
Or perhaps, “beneficiaries of the accumulated hard work of those who came before them in a way that leaves them able to spend their days solving new problems.”
Which is what you and I are today.
2026-03-31 19:00:00
We are in the early innings of a fundamental shift in how we understand the human body. The current medical model is reactive and episodic — you feel sick, you see a doctor, you get a snapshot. But your body is a complex machine running 24/7, and it deserves a software layer that can actually keep up.
That’s the idea behind what founder Will Ahmed from WHOOP calls the Health OS: continuous monitoring, proactive intelligence, and personalized coaching — all built on one of the most comprehensive longitudinal health datasets in existence. WHOOP has collected over 24 billion hours of continuous physiological data from more than 2.5 million members. That data, combined with a new medical-grade device and a generative AI coaching layer, positions WHOOP to bridge the gap between consumer wellness and clinical healthcare in a way no one else can.
This is why Collaborative Fund is leading a $575 million Series G round in WHOOP at a $10.1 billion valuation — our largest investment ever. Below is a lightly edited version of the cover letter to our term sheet:
Dear Will:
From the time Nicholas Negroponte introduced us back in April 2013 and we met at Grey Dog Cafe to talk about Bobo Analytics, I’ve been a true believer in your mission. We invested early, making WHOOP one of the core positions in our second Fund.
Empowering people with meaningful insights into their health is one of the most significant ways to improve human life. WHOOP represents exactly why I started Collaborative Fund: to back founders who push the world forward. You and your team have built not just an exceptional company, but an outstanding global brand. The awareness-to-purchase ratio is the best in its class, and it keeps growing because the product delivers.
In 2020, during the chaos of Covid, I remember telling you how much I was relying on WHOOP to monitor my respiratory rate and spot early signs of infection. That experience only deepened my conviction. We followed on in the Series E through our Opportunity Fund. Then in 2024, after my father’s heart scare, I bought him a WHOOP so I could track his recovery each day. Now we compare stats all the time using the community feature. It’s something that brings us both peace of mind and connection.
WHOOP stands apart as the only founder-led company in the health and wearable technology space, and it shows. The craftsmanship and attention to detail from your design and product teams are unmatched. The user experience is elegant and intuitive. The new medical-grade device positions the company to expand meaningfully into healthcare and even Medicare markets, bridging consumer and clinical worlds in a way few others can.
You and the team are building a generational company. I feel lucky to have had a front row seat, and I’m confident in making a firm‑defining investment as WHOOP enters its next phase of growth.
This opportunity has the full commitment of Collaborative Fund. We have attached a detailed term sheet outlining our proposal.
We’re proud to anchor a global syndicate that includes the Qatar Investment Authority, Mubadala Investment Company, Macquarie Group, Abbott Labs, Mayo Clinic, and cultural icons like LeBron James and Rory McIlroy. Together, this group will fuel the company’s international expansion across Europe, the GCC, Latin America, and Asia.
WHOOP is at a true inflection point. The opportunity ahead is bigger than wearables, and bigger even than wellness. It is to build the software layer for the human body: a system that helps people understand what is happening inside them, respond earlier, and live with more agency over their health. With unmatched data, exceptional product instincts, and a long-term vision, Will and the team are in a position to define what that future looks like.
You can read more about the deal in today’s New York Times: Whoop, a Wearable Health Device Maker, Raises $575 Million
2026-03-17 23:33:00
Everyone wants to be successful. Successful in our careers, our families, and our communities. I’ve certainly felt this way, that is until this past fall after attending two events, the first being a speech from someone who is more than a decade younger than I am.
In October I attended The Mario St. George Boiardi Forum for Ethical Reflection at my high school, The Landon School in Bethesda, Maryland. The forum celebrates the values my friend George exhibited as a student-athlete at Landon and then Cornell University before passing away on this day exactly twenty-two years ago after being struck in the chest by a lacrosse ball during a game.
This year’s speaker was Connor Buczek, the head men’s lacrosse coach at Cornell, which had recently won the University’s first national championship in any sport in close to five decades. Of even greater significance, it happened 21 years after George passed.
Halfway through his speech, Buczek turned to this topic of success.
Now, if I am being completely honest, I was expecting Buczek to echo the narrative you almost always hear in these scenarios — work hard, follow your passion, etc. and you will dramatically increase your odds for success. So, when he instead implored the room to chase something other than success, I perked up. After all, hadn’t he just defined success by reaching the pinnacle of his profession at the ripe old age of 32?
In his words,
“We are all chasing success at some level. We all want to be good at what we do. We want to be well regarded by our peers. However, how you do this is really important. Success often happens in a vacuum. We are so dead set on the outcome — Am I going to get into this college? Play this sport? Have this leadership role or win this accolade? Yet, being successful in this world isn’t all it’s cracked up to be. Rather we should aim to be significant, which means accomplishing things together. We want to make an impact on the people around us and bring people along with us. Success is meaningless unless we are being significant.”
This was particularly relevant because George’s life embodied significance, as evidenced by the fact that by my count, more than seventeen of his friends and teammates from high school and college have named their sons “George”.
Which brings me to the second event I attended.
A couple months after the Ethics Forum, Landon hosted an annual event that honors two graduates – one for having a distinguished career (either through service to his profession, community, or country) and another for outstanding service to the school.
While the criteria for each award are uniquely different, each year it is often difficult to distinguish which alum is winning which award based on their resumes alone. This year, though, the award winners seemed more obvious… at least on paper.
The alum who won the award for a distinguished career served in the U.S. Navy after attending Stanford in the late 1960s, has been a successful venture capitalist for more than two decades, has been a NVIDIA board member for even longer, took three companies public, and sold a fourth to Sun Microsystems.
Meanwhile, the winner of the award for outstanding service to the school has been a physical education teacher at the school for more than four decades, while also leading the weightlifting program and serving as the offensive line coach for the football team.
Yet, for as different as these two alums’ careers seemed on paper, my new appreciation for this issue of “success versus significance” made me realize that their impact on people is more similar than I may have thought in previous years.
The first served his country, created many jobs as a founder, generated meaningful investment returns for countless investors as a venture capitalist, and has helped change the world as we know it during his time at NVIDIA.
Meanwhile, the second alum also touched a lot of lives, albeit in a very different way. A way that I hadn’t fully appreciated until he explained why he chose to pursue the career he did.
He explained by saying,
“The reason I chose this career is because after graduating from college, I came to the conclusion that I could have a bigger and more long-lasting impact on students through teaching physical education, coaching sports, and working with them as a strength coach than I could as a classroom teacher.”
I loved his rationale,
“See, helping a young boy avoid always being the last one picked in a game or helping an unathletic or small boy gain coordination, speed, strength, and most importantly confidence, brings long-lasting effects. As a mediocre athlete myself, I knew I had to work hard to improve physically in order to play. In doing so, I learned that self-efficacy is the most valuable lesson that I can teach because it helps kids develop work ethic, character, and the ability to handle challenges long after they leave the playing field.”
In essence, this alum’s goal was to help young men who weren’t as strong or talented as people like George have the opportunity to share the same field with them. To be their teammates. To be their friends.
Considering how many young men had passed through that weight room over the years, I knew he had helped hundreds, if not thousands, of young men over the years. What I didn’t fully appreciate was how. That is until I had lunch with another alum a few weeks later.
This alum graduated a few years after I did, spent more than fifteen years in the Marine Corps, and looks every bit the part, standing 6’2 and 190 pounds with a short and tapered haircut.
During our conversation I told this Marine the story about these two award winners and, as I did, I witnessed a huge smile emerge across his face. Naturally, I asked him why?
His response?
“Because when I was in high school, I was the smallest kid in my class at 5’ 6” and 125 pounds, and didn’t hit my growth spurt until I got to college. As a result, it was difficult for me to make varsity sports, but Marty saw something in me. So, with his help in the weight room, I ended up occupying the 126-pound weight class for the wrestling team. Later, after being cut from the varsity lacrosse team in high school, I went on to not only make my college lacrosse team as a walk-on, I eventually was elected a captain as a senior. Then, with more to prove after college, I joined the Marines. Marty’s confidence in me was a big part of the reason why. When I was the smallest kid in my class, he was the one who instilled in me the confidence to know I could do anything. I owe him a lot. It’s the reason he and his wife were at my wedding a few years ago.”
Impacting lives quietly along the way. George did it in his own unique way, as did the two other alums.
Now that’s significance.
