Doug Miles

Fintech entrepreneur, father of four boys, blue water sailor & CEO of Olden Street Machine Learning, Inc. Innovating the future of OTC capital mkts via ML.

[Lupen @0xLupenn]

A former Morgan Stanley trader walks into MIT with colleagues from Harvard Management sitting in the back row.

He shows why following the "optimal" portfolio strategy cost funds $57 billion in a single month in 2008 - and what Harry Markowitz's Nobel Prize actually got wrong.

Harry Markowitz won the Nobel Prize in 1990 for Modern Portfolio Theory.

The idea: find the combination of assets that gives you the highest return for the lowest risk. Plot every asset on a chart. Draw the efficient frontier. Done.

Goldman Sachs, Two Sigma, every major fund uses this framework.

But the professor shows a problem nobody talks about.

Watch the moment (around 1:05:00 in):

He shows a video of the London Millennium Bridge.

Engineers designed it perfectly. Accounted for every known force. Built with cutting-edge technology.

It started swaying violently the first day people walked on it.

What went wrong? When the bridge moved slightly, pedestrians instinctively adjusted their step to keep balance. Which synchronized their movement. Which amplified the sway. Which made more people sync up.

The bridge nearly collapsed because everyone was individually optimizing - and that destroyed the system.

This is exactly what happened in 2008. Every major fund ran the same optimal portfolio model. When markets moved, they all hit the same stop-losses at the same time. The selling synchronized. The whole system crashed.

Funds that were up 20% in January were down 40% by October. The math was correct. The strategy was optimal. And it nearly broke the global financial system.

The lecture also covers a result that sounds impossible.

Take two assets. Asset A doubles in year one, then drops 50% in year two. Net result: zero.

Asset B drops 50% in year one, then doubles in year two. Net result: also zero.

But a 50/50 portfolio of A and B, rebalanced each year, returns 25%.

Both assets went nowhere. The portfolio made money. That's the math of diversification - the closest thing to a free lunch in investing.

Then he introduces risk parity - the approach Bridgewater's Ray Dalio used to build a $150 billion fund.

Standard 60/40 portfolios put 60% of capital in stocks, 40% in bonds. But stocks are three times more volatile than bonds. So 90% of the actual risk comes from equities.

Risk parity flips this. Equal risk, not equal capital. Then lever up to hit your return target.

The Sharpe ratio - your risk-adjusted return - stays the same when you add leverage. That's the math that made risk parity famous and made Bridgewater the largest hedge fund on earth.

The lecture closes with Claude Shannon - the father of information theory, the man who invented the mathematics behind every computer and phone on earth - who spent his later years at MIT trying to solve portfolio optimization.

His debate with Paul Samuelson about the Kelly Criterion is still unresolved.

If Shannon couldn't crack it, the problem is still open.

MIT 18.S096, Lecture 16. Free on YouTube.

bookmark this if you're studying quantitative finance

[Lara Logan @laralogan]

It is spreading. As more people recognize this as a war against God, they are speaking out.

[TRUMP SUPPORTER @_Postive_Vibes]

Education Secretary Linda McMahon dropped a bombshell on Maine Governor Janet Mills by placing her under investigation for civil rights violations as a result of Maine allowing men to compete in women’s sports.

[Doug Miles @cfobook]

@John_F_kJr @JessieJaneDuff A.

[LibertyOrNothing @LibertyNut1]

‼️ THE FIRST WOMAN TO EVER LEAD THE INTERNATIONAL OLYMPIC COMMITTEE MADE THE DECISION TO BAN TRANSGENDER WOMEN FROM FEMALE EVENTS AT THE OLYMPICS !

DO YOU SUPPORT BANNING TRANSGENDER WOMEN FROM FEMALE EVENTS AT THE OLYMPICS?

🅰️ YES
🅱️ NO

[Doug Miles @cfobook]

@oelma__ Hardly

[Finn Mallery @fin465]

Mark Cuban's take on selling AI agents to small businesses is the most underrated clip online right now

here's the business model he says will take over the 2030s (bookmark this):

pick 1 industry. learn how it actually runs. become the AI team they never hired but desperately need.

you don't need a CS background or funding.

you need a tool like Origami to send a great cold outreach sequence, and the patience to understand 1 industry better than anyone else in the room

bonus move: find someone who runs a business in that industry, knows nothing about AI, but knows everything about how the business actually works.

team up with them. bring the AI layer, they bring the operating knowledge.

you lift their margins. you lift their valuation multiple. you keep a stake in the upside.

[Doug Miles @cfobook]

@Irina_exh 1939

[Doug Miles @cfobook]

@WakeUpPatriott Yes

[Norgard @BrianNorgard]

The next Louisiana Purchase? Here’s an idea: the United States acquires the Baja California Peninsula from Mexico for $1 to $5 trillion.

Every Mexican citizen living in Baja receives dual U.S.-Mexico citizenship, plus a $50,000 investment account.

Then America gets to work: world-class infrastructure, deep-water ports, desalination, nuclear energy, housing, universities, and industry. Tijuana and Mexicali could become major reindustrialization zones.

In return, the United States gains nearly 1,800 miles of some of the most spectacular coastline on Earth and the chance to build the great new economic region.

Is this a crazy idea? Of course. But so was the Louisiana Purchase in 1803.

[Sassafrass84 @Sassafrass_84]

Life Before Barack Obama hits different when you actually remember it.

No ISIS carving up the Middle East.
No BLM turning cities into war zones.
No Antifa burning down businesses while cops were told to stand down.
No “war on police” narrative.
No Russia Hoax witch hunt.
No expensive Obamacare disaster.
No full-blown Trump Derangement Syndrome.

We had problems, sure. But we weren’t drowning in manufactured chaos and identity politics.

Obama didn’t “inherit” this mess — a whole lot of it bloomed on his watch.

[Esan @esandurrani]

Introducing Honen

Turn your company context into interactive courses that self-improve over time

We partnered with NVIDIA to bring AI literacy to 250,000 learners

We're ensuring no person or company gets left behind

Get started at https://t.co/rH0oOr37Kv

[Dipanshu Kushwaha @Dipanshu_AI]

🚨 Claude just changed the game.

All you need is:

💻 A laptop or Mobile
🌐 Internet connection
⏰ 60 minutes a day

That’s enough to build a $7,200/month online income stream using AI.

No coding.
No expensive setup.
No years of experience.

Most people still use AI for fun…

But smart creators are quietly using Claude to:

• Create digital products
• Offer AI services
• Write viral content
• Automate work
• Build online income streams

Usually, I sell this detailed guide for $97…

But today you can get it FREE. 🎁

Inside you'll discover:

✅ The exact asset
✅ My full workflow
✅ The Claude prompts I personally use
✅ How to scale to $10K/month
✅ How beginners can start fast

Want it?

❤️ Like this post
💬 Comment “AI”
➕ Follow me to receive it in DM

⏳ Available FREE for 48 hours only.

[TRUMP SUPPORTER @_Postive_Vibes]

BOOM 💥 — USPS whistleblower Jesse Morgan confessed about the 2020 elections fraud:

"I transported 288,000 completed ballots from New York, straight to Pennsylvania. They were already filled out... I didn't know, so I decided to speak up."

[Khusboo Tayal @KhusbooT14835]

The engineer who built Claude Code just dropped a 28-minute video on how to write prompts that actually work

I've seen $300 courses that don't cover what he shows in the first 10 minutes

CLAUDE.md files, memory shortcuts, parallel sessions, prompting patterns

all in one video and completely free works whether you're a developer, a beginner, or someone who's been using Claude for months.

[✞🎀TrumpGirlOnFire 🔥 @TrumpGirlOnFire]

People are literally starving in America… …while 200,000 DEAD PEOPLE are cashing food stamps. Brooke Rollins just exposed the massive SNAP fraud — red states cooperated and found it. Blue states? They’re SUING to PROTECT the scam. This is Democrat priorities in one sentence.

[Misy7 @MisyDP]

Before buying a dog know what they were bred for. The genes are really strong. 7-week-old pups.

Happy Sunday everyone.

[GRANDPA’s FREE ADVICE @GOP_is_Gutless]

🚨 JUST IN: Marco Rubio DEPORTS Islamic Terrorists’ Family!

Marco Rubio just booted the family of “Screaming Mary”

Ebtekar — spokeswoman for the 1979 Iranian terrorists who stormed the U.S. Embassy, took 52 Americans hostage for 444 days, and subjected them to beatings, starvation, and mock executions.

Obama’s admin let her son, his wife, and their child into America with visas in 2014 and gave them green cards through the Diversity Visa Program in 2016.

Rubio terminated their lawful permanent resident status. They are now in ICE custody and facing removal.

“Her family should never have been allowed to benefit from the extraordinary privilege of living in our country. America can never become home for anti-American terrorists or their families — and under the Trump Administration, it never will.”

Finally — putting America First. No more terrorist families living here on our dime.

What do you think? 👇
#DeportThemAll #AmericaFirst #MarcoRubio #TrumpAdministration #NoMoreTerrorists

[John Kennedy @SenJohnKennedy]

82 years ago today, brave American heroes like CPL Edmond Elisar of Ascension Parish, Louisiana stormed the beaches of Normandy to liberate Europe from tyranny.

He was only 22 years old when he gave his life in service of our country so we could live free.

God made men like Edmond rare. Our nation must never forget his sacrifice.