Capitalogix

When Worlds Collide: Timeless Wisdom & Evolutionary Technology in Trading with Matthew Piepenburg

Back in 2020, I had a Zoom meeting with Matthew Piepenburg of Signals Matter. Of course, being the height of the Pandemic, it was over Zoom. Even though it was a private discussion, there was so much value in our discussion that we decided to share parts of it here. 

While Matt's understanding of markets is based on Macro/Value investing, we use advanced AI and quantitative methods for our approach. 

As you might expect, there are a lot of differences in how we view the world, decision-making, and the current market environment. Nonetheless, we share a lot of common beliefs as well.   

Our talk explores several interesting areas and concepts. I encourage you to watch it below. 

 

Via YouTube.

To summarize a couple of the key points, markets are not the economy, and normal market dynamics have been out the window for a long time. In addition, part of why you're seeing increased volatility and noise is that there are so many interventions and artificial inputs to our market system.

While Matt and I may approach the world with very different lenses, we both believe in "timeless wisdom". 

Ask yourself, What was true yesterday, today, and will stay true tomorrow? 

That is part of the reason we focus on emerging technologies and constant innovation ... they remain relevant. 

Something we can both agree on is that if you don't know what your edge is ... you don't have one. 

 

Hope you enjoyed the video.

Let me know what other topics you'd like to hear more about. 

Onwards!

Via YouTube.

To summarize a couple of the key points, markets are not the economy, and normal market dynamics have been out the window for a long time. In addition, part of why you're seeing increased volatility and noise is that there are so many interventions and artificial inputs to our market system.

While Matt and I may approach the world with very different lenses, we both believe in "timeless wisdom". 

Ask yourself, What was true yesterday, today, and will stay true tomorrow? 

That is part of the reason we focus on emerging technologies and constant innovation ... they remain relevant. 

Something we can both agree on is that if you don't know what your edge is ... you don't have one. 

 

Hope you enjoyed the video.

Let me know what other topics you'd like to hear more about. 

Onwards!

The Benner Cycle: How Not To Predict Markets

When I first became interested in trading, I would often consult many traditional sources and old-school market wisdom.  I particularly liked the Stock Trader's Almanac. 

While there is real wisdom in some of those sources, most might as well be horoscopes or Nostradamus-level predictions.  Throw enough darts, and one of them might hit the bullseye. 

Still, it seems better than using astrology to trade. 

Want something easy to predict?  Traders love patterns ... from the simple head-and-shoulders to Fibonacci sequences and the Elliot Wave Theory.

Here's an example from Samuel Benner, an Ohio farmer, in 1875.  That year, he released a book titled "Benners Prophecies: Future Ups and Downs in Prices," and in it, he shared a now relatively famous chart called the Benner Cycle.  Some claim that it's been accurately predicting the ups and downs of the market for over 100 years.  Let's check it out. 

 

 

Here's what it does get right ... markets go up, and then they go down ... and that cycle continues.  Consequently, if you want to make money, you should buy low and sell high ... It's hard to call that a competitive advantage.

Mostly, you're looking at vague predictions with +/- 2-year error bars on a 10-year cycle. 

However, it was close to the dot-com bust and the 2008 crash, so even if you sold a little early, you'd have been reasonably happy with your decision to follow the cycle.

The truth is that we use cycle analysis in our live trading models.  However, it is a lot more rigorous and scientific than the Benner Cycle.  The trick is figuring out what to focus on—and what to ignore. 

Just as humans are good at seeing patterns where there are none ... they tend to see cycles that aren't anything but coincidences. 

This is a reminder that just because an AI chat service recommends something, it doesn't make it a good recommendation.  Those models do some things well.  Making scientific or mathematically rigorous market predictions probably isn't the area to trust ChatGPT or one of its rivals ... yet. 

We're seeing bots improve at running businesses and writing code, but off-the-shelf tools like ChatGPT are still known for generating hallucinations and overconfidence. 

Be careful out there.

Market Growth in the First Half of 2025.

According to S&P Global, the U.S. market cap rose by 4.7% in the past 6th months. This represents a modest gain compared to the average market capitalization growth of 12.2% during the same period.

Leaders in growth were South Korea, Spain, Germany, Italy, and Brazil.

 

via VisualCapitalist

We have previously discussed this, but in addition to investments in technology and artificial intelligence, global capital is also being directed toward emerging markets, where many businesses are being established.

At first glance, some may see U.S. underperformance, but it can also be read as a sign of relative maturity and stability. Another potential perspective is that U.S. companies have already experienced explosive growth in recent years, particularly in sectors such as tech and AI, suggesting the market may currently be in a phase of consolidation.

While it's always great to see explosive growth, people undervalue resilience and steady growth, especially in light of the volatile first quarter of the year. 

Time will tell! 

 

How Long You Have Left

We only have a limited time on this earth ... and a lot of it is spent on frivolous activities. 

How much time do you think the average millennial spends on their phones ... or a baby-boomer sits in front of the TV?

The answer is a lot.

Although this chart hasn't been updated recently, it still provides a helpful glimpse of the bigger picture. 

 

via Anna Vital

Nine years in front of entertainment devices - another 10.5 years spent working. You get the idea.

If you have goals you want to accomplish, places you want to go, and lifestyle aspirations to experience, this puts the idea of finding and living your passion into perspective. 

Do you have the time to waste it?

VisualCapitalist put together a chart projecting longevity based on 2020 mortality rates.

 

via visualcapitalist
 

According to this calculator, since I'm over 60, I only have about 20 years left.   I expect more!

There are some interesting statistical facts in this; for example, an average American baby boy can expect to live until 74 ... but if that boy turns 21, his life expectancy jumps to over 75. 

While these numbers appear high, there are two key considerations. First, COVID-19 heavily reduced these numbers because mortality rates increased. 

Also, remember that these numbers are based on 2020 averages, which may differ from your own (specifically considering your race, income, location, etc.). These numbers also don't take into account expected medical and technology advances, etc. 

Ultimately, I believe Purpose is one of the most significant catalysts of longevity. People often die when they retire ... not because they're done working, but because they're done striving. 

If you're not growing, you're dying!

What My Recent Surgery Reminded Me About Technology.

One of my recurring messages is to focus on what you want, rather than what you don’t want.

Likewise, I believe the best way to get through challenging periods is to focus on your resources or progress.

Anyway, two weeks ago, I had a minor surgery.

Let’s face it, very few people “want” to have surgery (even small ones) ... and, for those that do, it’s a sign that something else is bothering them even more.

As much as it sucked, I have a lot to be grateful for. The practical realities of time, technology, and progress made the procedure and the recovery process easier than at any point in our species’ history.

Procedures that used to mean multiple days in a hospital bed have you home in under 24 hours.  

It brought back memories of my knee surgery from 12 years ago... and reminded me of what technology makes possible.

Before my knee surgery, I wasn’t enjoying the prospect of the needles, the knock-out drugs, the cutting, or the recovery process. Frankly, I was scared.

 

 

History is littered with tales of once-rare resources that have become plentiful through innovation. The reason is pretty straightforward: scarcity is often context-dependent.

Imagine a giant orange tree packed with fruit. If you pluck all the oranges from the lower branches, you are effectively out of accessible fruit. From that limited perspective, oranges are now scarce. But once someone invents a piece of technology called a ladder, the problem is solved.

Here is a picture from inside my knee (unlike years ago, they didn’t have to slice me open to gain access for the picture or the repair): less damage, less time, less drugs, less recovery.

 

 

Bottom-Line: I walked over 2,500 steps the day after the surgery. 

Think how far diagnostics and surgery have come since then?

Whether it is 3D imaging, minimally invasive surgical instruments, or linking big data and elastic computing, technology is a resource-liberating mechanism. It can make the ‘once scarce’ the ‘now abundant’ (or ‘readily accessible’) ... and a lot less painful.

 

From ‘Doctor Klingon’ to Clarity — and What That Means for You

But where are we today – and how was surgery different?

It sounds like a joke, but the future of medicine is in your pocket.

One of the biggest differences for me was having AI available to help me feel informed throughout the process. From the beginning, where I wanted to understand the issue and potential solutions, to having AI available on my phone in the recovery room. For example, while waiting for the doctor to tell me “how things went,” I downloaded the surgical notes from the hospital portal, only to find that they were written in “doctor speak” Klingon. So I opened Perplexity in incognito mode and asked it to interpret the notes, and explain everything to me as if I had minimal medical knowledge but still wanted to understand what happened and what I should expect. The result was incredibly comforting, and I was able to use that to send updates to family and friends.

Meanwhile, try to imagine the extensive technology used by doctors and medical staff throughout the process to test, analyze, interpret, monitor, and treat.

Soon, we’ll be able to utilize real-time data for diagnostics and design treatment plans and preventive care tailored to an individual’s unique biology and lifestyle. As a result, personalized, predictive healthcare will become the norm. Likewise, the idea of tailoring treatment to your unique biology will be expected, not exceptional.

It’s also easier than ever to imagine the shift from reactive to preventive medicine. Surgery will become less frequent as AI and wearables catch problems before they require intervention. Likewise,. That means better care and better outcomes - at scale!

And it is all getting better faster than before.

Pretty cool! 

It brought back memories of my knee surgery from 12 years ago... and reminded me of what technology makes possible.

Before my knee surgery, I wasn’t enjoying the prospect of the needles, the knock-out drugs, the cutting, or the recovery process. Frankly, I was scared.

 

 

History is littered with tales of once-rare resources that have become plentiful through innovation. The reason is pretty straightforward: scarcity is often context-dependent.

Imagine a giant orange tree packed with fruit. If you pluck all the oranges from the lower branches, you are effectively out of accessible fruit. From that limited perspective, oranges are now scarce. But once someone invents a piece of technology called a ladder, the problem is solved.

Here is a picture from inside my knee (unlike years ago, they didn’t have to slice me open to gain access for the picture or the repair): less damage, less time, less drugs, less recovery.

 

 

Bottom-Line: I walked over 2,500 steps the day after the surgery. 

Think how far diagnostics and surgery have come since then?

Whether it is 3D imaging, minimally invasive surgical instruments, or linking big data and elastic computing, technology is a resource-liberating mechanism. It can make the ‘once scarce’ the ‘now abundant’ (or ‘readily accessible’) ... and a lot less painful.

 

From ‘Doctor Klingon’ to Clarity — and What That Means for You

But where are we today – and how was surgery different?

It sounds like a joke, but the future of medicine is in your pocket.

One of the biggest differences for me was having AI available to help me feel informed throughout the process. From the beginning, where I wanted to understand the issue and potential solutions, to having AI available on my phone in the recovery room. For example, while waiting for the doctor to tell me “how things went,” I downloaded the surgical notes from the hospital portal, only to find that they were written in “doctor speak” Klingon. So I opened Perplexity in incognito mode and asked it to interpret the notes, and explain everything to me as if I had minimal medical knowledge but still wanted to understand what happened and what I should expect. The result was incredibly comforting, and I was able to use that to send updates to family and friends.

Meanwhile, try to imagine the extensive technology used by doctors and medical staff throughout the process to test, analyze, interpret, monitor, and treat.

Soon, we’ll be able to utilize real-time data for diagnostics and design treatment plans and preventive care tailored to an individual’s unique biology and lifestyle. As a result, personalized, predictive healthcare will become the norm. Likewise, the idea of tailoring treatment to your unique biology will be expected, not exceptional.

It’s also easier than ever to imagine the shift from reactive to preventive medicine. Surgery will become less frequent as AI and wearables catch problems before they require intervention. Likewise,. That means better care and better outcomes - at scale!

And it is all getting better faster than before.

Pretty cool! 

Diminishing Returns in AI: The Most Common AI Mistake

At some point, more of the same stops paying off ... it is called the law of diminishing returns.

via Sketchplanations

Nature (and common sense) reminds us that equilibrium is important. For example, when you exercise too much, you get injured; when you drink too much water, you get poisoned; etc. 

This concept applies almost everywhere.

• It's why diversification is so important in portfolio construction theory. 
• Or, why you don't want to put all your eggs in one basket (concentrating your risk).
• And, my favorite, it's also why you shouldn't only eat vegetables.

A related nugget of wisdom from the extreme ... Too much of a good thing is a bad thing! 

And of course ... Be moderate in everything, including moderation.

A recent study on the effects of ChatGPT use on brain activity also supports this theme. 

via "Your Brain on ChatGPT: Accumulation of Cognitive Debt when Using an AI Assistant for Essay Writing Task" 

The study divided 54 subjects into three groups, and asked them to write several SAT essays using ChatGPT, Google, or nothing at all. They used an EEG to record the writers' brain activity. ChatGPT users showed the lowest brain engagement. Over time, ChatGPT users got lazier. 

As a result, the ChatGPT essays also ended up lacking original thought and sounding similar. 

 

The paper suggests that the use of LLMs could harm learning and retention. The group that wrote without any help showed the highest neural connectivity, and higher brain activation in creativity ideation, memory load, and semantic processing. This group was more engaged and curious, and expressed higher satisfaction with their work. 

 

The paper hasn't been peer-reviewed yet and has a small sample size. 

Ultimately, I think it's telling us something we probably could have already guessed. If you're not actually the one reading or writing something ... you're not going to absorb the information as well. Your brain isn't going to activate as well. And if you're not finding other places to train your brain, you'll get worse at critical thinking. 

 

A few weeks ago, I wrote about my research process and how AI has both bolstered and hindered certain aspects of it. I'm casting a wider net, but going less deep. 

So now, I’m exploring how to maintain a balance. I still want to leverage AI’s value, while reintroducing a layer of slowness and reflection into the process. Maybe that means manually summarizing some articles. Maybe it means pausing to journal about what I’ve read, or discussing it with someone. The goal is not to abandon the efficiency — but to ensure that efficiency doesn’t come at the cost of depth. - via "Is AI Making Your And Your Team Smarter?"

This isn't a call to avoid AI or to slow down its development. It's a call to deliberation and intentionality. Students are flaunting that they're using ChatGPT to shirk the system. Companies are releasing AI-written copy not only on their websites but also in press releases. Humans are falling in love with chatbots and leaving their spouses. 

 

Meanwhile, AI is also the underpinning of countless enhancements and increased productivity. 

 

The same thing happened with the Internet. 

 

At a certain point, overreliance becomes a crutch, not a tool. 

 

I bet AI makes unintelligent and lazy people lazier and less intelligent. 

I'm positive it can make YOU smarter and more effective if you use it in moderation and to support your unique abilities. 

Onwards! 

Nature (and common sense) reminds us that equilibrium is important. For example, when you exercise too much, you get injured; when you drink too much water, you get poisoned; etc. 

This concept applies almost everywhere.

• It's why diversification is so important in portfolio construction theory. 
• Or, why you don't want to put all your eggs in one basket (concentrating your risk).
• And, my favorite, it's also why you shouldn't only eat vegetables.

A related nugget of wisdom from the extreme ... Too much of a good thing is a bad thing! 

And of course ... Be moderate in everything, including moderation.

A recent study on the effects of ChatGPT use on brain activity also supports this theme. 

via "Your Brain on ChatGPT: Accumulation of Cognitive Debt when Using an AI Assistant for Essay Writing Task" 

My Artificial Intelligence Journey

Time seems to go faster as I get older. Likewise, technology seems to be advancing faster than ever, too.

Take AI as an example... even though I've been involved in this field for many years, I'm surprised by how rapidly it's improving now.

I suspect that part of the surprise comes from comparing the current pace of change to my memories of how long it took to improve in the past. Even though I had a sense of the quickening, the thing about exponential technologies is that there's a tipping point ... and clearly we're past that point on the curve.

I'm often met with surprise when I talk about my AI journey ... because it began in 1991, when it was still hard to spell AI.

Looking back, it makes a lot more sense to me than it did as I was moving through it. Here is a video about that journey and what it means for you and your future. 

 

Click here to view the transcript of the video.

Looking back on my life and career, one could argue that I got my start in AI with my most recent company, Capitalogix, which was founded over 20 years ago. Or, perhaps, we could go back further and say it started with my previous company, IntellAgent Control (which was an early AI company, focused on the creation and use of intelligent agents). By today's standards, the technology we used back then was too simple to be considered AI, but at the time, we were on the cutting edge.

Maybe we should go further back and say it started when I became the first lawyer in my firm to use a computer ... or was it when I first fell in love with technology? 

The truth is ... I've spent my whole life on this path. My fascination with making better decisions, taking smarter actions, and getting better results probably started when I was two years old (because of the incident discussed in the video).

Ultimately, the starting point is irrelevant. Looking back, it seems inevitable. The decisions I made, the people I met, and my experiences ... they all led me here.

However, at any point in the journey, if you asked, "Is this where you thought you'd end up?" I doubt that I'd have said yes. 

I've always been fascinated by what makes people successful and how to become more efficient and effective. In a sense, that's what AI does. It's a capability amplifier. 

When I transitioned from being a corporate securities lawyer to an entrepreneur, Artificial Intelligence happened to be the best vehicle I found to do that. It made sense then, and it makes sense now.

Like most things in life, it's easy to see the golden thread looking backwards, but it's a lot harder to see projecting forwards.

I wouldn't have it any other way. It certainly keeps things interesting.

Onwards!

Time seems to go faster as I get older. Likewise, technology seems to be advancing faster than ever, too.

Take AI as an example... even though I've been involved in this field for many years, I'm surprised by how rapidly it's improving now.

I suspect that part of the surprise comes from comparing the current pace of change to my memories of how long it took to improve in the past. Even though I had a sense of the quickening, the thing about exponential technologies is that there's a tipping point ... and clearly we're past that point on the curve.

I'm often met with surprise when I talk about my AI journey ... because it began in 1991, when it was still hard to spell AI.

Looking back, it makes a lot more sense to me than it did as I was moving through it. Here is a video about that journey and what it means for you and your future. 

 

Click here to view the transcript of the video.

Looking back on my life and career, one could argue that I got my start in AI with my most recent company, Capitalogix, which was founded over 20 years ago. Or, perhaps, we could go back further and say it started with my previous company, IntellAgent Control (which was an early AI company, focused on the creation and use of intelligent agents). By today's standards, the technology we used back then was too simple to be considered AI, but at the time, we were on the cutting edge.

Maybe we should go further back and say it started when I became the first lawyer in my firm to use a computer ... or was it when I first fell in love with technology? 

The truth is ... I've spent my whole life on this path. My fascination with making better decisions, taking smarter actions, and getting better results probably started when I was two years old (because of the incident discussed in the video).

Ultimately, the starting point is irrelevant. Looking back, it seems inevitable. The decisions I made, the people I met, and my experiences ... they all led me here.

However, at any point in the journey, if you asked, "Is this where you thought you'd end up?" I doubt that I'd have said yes. 

I've always been fascinated by what makes people successful and how to become more efficient and effective. In a sense, that's what AI does. It's a capability amplifier. 

When I transitioned from being a corporate securities lawyer to an entrepreneur, Artificial Intelligence happened to be the best vehicle I found to do that. It made sense then, and it makes sense now.

Like most things in life, it's easy to see the golden thread looking backwards, but it's a lot harder to see projecting forwards.

I wouldn't have it any other way. It certainly keeps things interesting.

Onwards!

Is Crypto Going Mainstream in 2025?

Humans are good at recognizing significant changes on the horizon, but not nearly as good at understanding the second and third-order consequences of those changes.

A great example is the Internet. As it spread, most adults understood that it would bring “big changes”. However, even as a tech entrepreneur at the time, I didn’t fully grasp what the rise of the Internet would cause or make possible.

I feel the same way today about the rise of AI. It literally will change everything.

Close behind that is what’s happening in Crypto.  

 

Where Attention Goes, Money Flows

I don’t claim to be a crypto expert or fan. Historically, I’ve been skeptical and resistant on many levels. Nevertheless, I've always argued the blockchain was here to stay. Now, even Crypto seems to be becoming an inevitability.

Governments are becoming supporters. Regulators are falling in line. Big banks and industry are building infrastructure. New giants are forming. Coinbase recently joined the S&P 500. Circle just had a wildly successful IPO. And the performance of stocks like these hints at the growing market appetite for crypto businesses.

Currently, Crypto’s market cap is over $3 trillion. At the beginning of Trump’s presidency, the cryptocurrency markets experienced a significant surge. Since Donald Trump’s re-election in November 2024, Bitcoin has surged 60 percent, reaching record highs. However, Bitcoin isn’t the only cryptocurrency experiencing a surge; even meme coins are seeing a massive increase in value. 

Nevada recently hosted a Bitcoin conference, featuring speakers such as Vice President JD Vance, Trump’s two eldest sons, Donald Trump Jr. and Eric Trump, as well as White House crypto advisor David Sacks. 

Despite the growth (and Trump’s support), there are still mainstream obstacles ... obstacles that may be addressed by increased investment in stablecoins. For context, countries such as the UAE and Vietnam boast higher rates of cryptocurrency ownership than the United States. 

 

Stablecoins Are Rising

A stablecoin is a type of cryptocurrency designed to maintain a stable value, typically pegged to a reference asset like a fiat currency (e.g., U.S. dollar) or a commodity (e.g., gold). This contrasts with other cryptocurrencies, such as Bitcoin, which can experience significant price fluctuations. They serve many purposes, but ultimately believe they’re an interesting way to store value on-chain and take steps into the crypto world. 

The stablecoin market in 2025 is dominated by a handful of major platforms and issuers, recognized for their scale, transparency, and integration into both traditional finance and decentralized finance (DeFi) ecosystems. The two largest and most respected stablecoin platforms are Tether and Circle.

 

    Tether (USDT)

•Market Position: Tether remains the largest stablecoin by market capitalization, with over $140 billion in circulation and controlling more than 60% of the stablecoin market.

•Key Features: USDT is widely used across centralized exchanges, DeFi protocols, and global payment networks. It is primarily backed by U.S. Treasury bills and managed by Cantor Fitzgerald, providing a reserve base comparable to that of major national treasuries.

 

    Circle (USDC)

•Market Position: USDC is the second-largest stablecoin, with a market cap exceeding $60 billion.

•Key Features: Known for its transparency, Circle publishes weekly attestations of reserves, which are held in cash and short-term U.S. government treasuries.

 

Stablecoin funding is projected to 10X.

 

CBInsights via Voronoi

When cryptocurrency started to gain popularity, I expressed concerns about how banks and governments would resist widespread adoption until they could introduce regulation and gain control over it. I remember confidently saying that, throughout history, governments have always protected the right to print and tax coin. That is still true ... it just means something different to me, now, than it did when I said it.

I’m starting to pay more attention to Crypto, blockchain, and other emerging DeFi technologies.

I’m seeing an increasing flow of talent, opportunities, and resources to this space.

For example, major payment players like Mastercard and Visa are allowing stablecoin transactions and even creating their own coins. 

I do believe growth in stablecoins will also result in growth in other forms of cryptocurrency as well. 

For context, here are the best-performing cryptocurrencies of 2024. 

 

via VisualCapitalist

I still won’t pretend to be knowledgeable about the various coins, but I recognize that they are becoming more common and useful as speculation markets. 

All in all, I believe we are witnessing the birth of another blue ocean, and we can expect increased attention and investment to continue.

Onwards! 

Trying to Understand Happiness ...

I am often amazed at how little human nature has changed throughout recorded history.

Despite the exponential progress we’ve made in health, wealth, society, tools, and understanding ... we still struggle to find meaning, purpose, and happiness in our lives and our existence.

Last month, I shared an article on Global Happiness Levels in 2025. Here are a few bullets that summarize the findings: 

• We underestimate others’ kindness, but it’s more common than we think.
• Community boosts happiness—eating and living with others matter.
• Despair is falling globally, except in isolated, low-trust places like the U.S.
• Hope remains—trust and happiness can rebound with connection and a sense of purpose.

Upon reflection, that post didn’t attempt to define happiness. This post will focus on how to do that.

While it seems like a simple concept, happiness is complex. We know many things that contribute to and detract from it; we know humans strive for it, but it is still surprisingly challenging to put a uniform definition on it. 

A few years ago, a hobbyist philosopher analyzed 93 philosophy books, spanning from 570 BC to 1588, in an attempt to find a universal definition of Happiness. Here are those findings.

 

via Reddit.

It starts with a simple list of definitions from various philosophers. It does a meta-analysis to create some meaningful categories of definition. Then it presents the admittingly subjective conclusion that:

 

Happiness is to accept and find harmony with reason. 

 

My son, Zach, pointed out that while “happiness” is a conscious choice, paradoxically, the “pursuit of happiness” often results in unhappiness. Why? Because happiness is a result of acceptance. However, when happiness is the goal, you often focus on what you’re lacking instead of what you already have. You start to live in the ‘Gap’ instead of the ‘Gain’. 

So, it got me thinking – and that got me to play around with search and AI, a little, to broaden my data sources and perspectives. If you would like to view the raw data, here are the notes I compiled (along with the AI-generated version of what this article could have been, had it been left to AI, rather than me and Zach).

Across centuries, philosophers have wrestled with a deceptively simple question: What does it mean to live a good life?

 

As entrepreneurs, investors, and leaders, we often chase performance, innovation, or edge — but underneath it all, there’s a quieter inquiry: Am I living well?

 

Happiness aside, across 93 influential philosophical texts spanning two millennia, one word consistently reappears: Eudaimonia. This is not happiness in the modern sense of pleasure, but a richer concept of human flourishing — a life filled with purpose, virtue, and meaning.

 

• Ancient thinkers saw happiness not as a mood, but as a life aligned with purpose and virtue.
• Some prioritized inner character; others emphasized harmony with the divine or nature.
• Debate endures over the role of external goods — wealth, luck, friends.
• During the Renaissance, the conversation shifted toward subjective experience.
• Across eras, the thread remains: Happiness is cultivated, not consumed.

 

Contradictions and Tensions

Thoughts on happiness contain paradoxes, contradictions, and tensions. Examining the boundaries between what you are certain of and what you are uncertain of is where insights occur. Here are a few to get you started.

 

• Virtue vs. External Goods: Aristotle acknowledges external goods (wealth, friends) as necessary for complete happiness, while Stoics claim virtue alone suffices. This tension challenges the simplicity of virtue-based happiness, suggesting a nuanced balance between inner character and outer circumstances.
• Subjective vs. Objective Happiness: Ancient philosophers often defined happiness as an objective state (living virtuously or intellectually flourishing), whereas modern definitions more often emphasize the subjective satisfaction varying by individual. This tension probes whether happiness is a universal or personal experience.
• Happiness as Pleasure vs. Happiness as Duty/Struggle: Epicureanism equates happiness with pleasure (absence of pain), but Cynics and Stoics emphasize enduring hardship and discipline as the path to happiness, which presents a paradox between comfort and resilience.

 

Three Metaphors To Help You Think About Happiness

Metaphors help make abstract ideas more concrete, memorable, and easier to grasp. Here are three to consider.

 

The Ship Captain (Stoicism)

• Metaphor: You can’t control the ocean (external events), but you can steer your ship (your mind). 
• Clarification: Highlights control over internal states despite external chaos.

The Team Soul (Plato’s Tripartite Soul)

• Metaphor: The soul is a team where reason is the coach, spirit is the player, and appetite is the goalie. Happiness is achieved when the coach directs the players well. 
• Clarification: Demonstrates the importance of internal harmony and self-governance.

The Garden (Aristotle’s Life Cultivation)

• Metaphor: Happiness is like tending a garden over time — it requires continuous effort, nurturing virtues (soil quality), and sometimes external help (sunlight, rain). 
• Clarification: This shows happiness as a process, not a momentary state.

Reach out – I’m curious to hear what you think!

Make Way For 2025's Biggest Unicorns

Billion-dollar startups are becoming increasingly common with VC funding surging, and an increased focus on exponential technologies. 

VisualCapitalist put together an infographic based on May's PitchBook that highlights the newest Unicorns.

If you are curious, PitchBook defines Unicorns as venture-backed companies valued at $1 billion or more after a funding round, until they go public, get acquired, or drop below that valuation.

Here is the list for 2025.

 

Pitchbook via visualcapitalist

Topping the list (and eclipsing every other company on the list) is Yangtze Memory out of China. They're focused on flash memory and solid-state drives. Yup, that's still a thing.

Also high on the list is Abridge, an American AI startup focused on turning doctors' conversations with patients into documentation. If you've ever talked with a clinician of any sort, you know how time-consuming documentation currently is. The combination of AI and longevity—or age reversal—is likely to become an increasingly hot area for investment.

Meanwhile, a rising tide floats many boats ... and with the continuing rise of funding in AI, you'll also find a growing list of AI unicorns, like Peregrine, Synthesia, AnySphere, Mercor, and The Bot Company. 

Although these individual companies are interesting, the larger trend is probably more significant. 

There have been 43 new unicorns in 2025 alone. And while the most profitable unicorns from 2024 are still OpenAI, ByteDance, and SpaceX, their competition is on the rise.

I've been a tech entrepreneur for decades, so I'm used to the constant march of progress. But this feels different. The pace is quickening!

We certainly live in interesting times!