Today I'm announcing something my team and I have been working on for the last year:

The Outliers Summit 2026

It’s two days with the most unreasonably ambitious people I know, hosted alongside my friend Andrew Yeung and in partnership with AngelList. 

It will be held on November 5 and 6 in New York City and includes sessions with: 

Going to be one hell of a time :)

Important: Early-bird pricing ends August 12 (two weeks from today), after which prices go up 30%. 

As of writing this Wednesday evening, there are 87 early-bird tickets left across all tiers, and only 41 single-day passes.

Once we hit our ticket cap or the deadline, our early-bird offer will expire!

Click here to learn more »

Every tax strategy and personal finance tip I've shared has been about protecting or multiplying the income or wealth you already have.

I still believe that a Solo 401k, for example, is the best retirement account in America. But it does nothing for you without the self-employment income. 

Direct indexing, PTET, QSBS, the mega backdoor Roth, they are all leverage applied to income you’ve already built.

Which means the highest-ROI financial move most people can make isn't a tax deduction. 

It's getting close to people building incredible things so growth doesn’t feel so insane.

Quick context: I started my career building viral apps from my dorm room. I went on to build Teachable and eventually sold it for $250M. I raised ~$100M (mostly from Twitter DMs) to build a private venture fund post-exit, until I became obsessed with helping high earners optimize their tax bill through smarter investing strategies and that became my second startup Carry. Now I’m building USVC to help broaden access to the companies building the future. 

Everything that’s financially gone well in my life traces back to starting or investing in a business, which I believe is the best risk-adjusted path to real wealth in this country.

And many of those decisions came after getting close with someone who made it look more achievable.

Two years ago, Andrew Yeung and I partnered up to build something special. 

We called it the OOO Summit, short for Owners, Operators, Outliers. 

Over 600 people came to the first one in 2024. Last year we hosted 800+ at the main event and thousands more across the events of the week.

We’ve featured the likes of Guillermo Rauch, Andrew Yang, Sahil Bloom, Sam Parr, Alex Lieberman, Packy McCormick, Nathan Barry, Steph Smith, Justin Welsh and Kyla Scanlon.

This year, we're changing the name and expanding our main event capacity to 1200!

The world has changed dramatically in the last year. 

The people showing up are not only business owners and operators. There are entire categories of work that did not exist when we picked that name. Multi-hyphenates. Hybrid creators. Solo builders. People running companies of one with agents doing the rest. Careers nobody has a title for yet.

We realized there was only one way to describe us: outliers. 

People who took the unconventional path and stayed unreasonably ambitious.

Most people optimize for the path they were handed. Outliers bend it to meet their vision.

And beyond a name change, the Outliers Summit is also meaningful different in structure: 

November 5: Build Like An Outlier. Tactical sessions across the disciplines that actually matter in the AI era. Think of this as the “everything I know I should learn but haven’t made the time for yet” day. The goal is to leave having built the thing yourself: an app, an agent, an audience, a brand.

November 6: Think Like An Outlier. Candid, off-the-record conversations about the bets and mindsets that separate outliers from everyone else. Think of this as the “stuff people won't say (or can’t say) on a podcast” day. The goal is to leave inspired to take on the challenges that come with building. 

And we’re excited to share our first wave of confirmed speakers as part of our launch:

I’ve gone to a lot of conferences in my day. 

Most of them are a trade show with a keynote attached. You pay $2,000, watch someone read some slides, and leave with a tote bag. Boo!

Two things make this one different.

The room is intentionally filtered. 

More than 4,000 outliers from over 3,000 companies have come through our summit in the last 2 years. 

From that group:

It’s an awesome crowd and it’s always super cool to see what people go on to do afterward. 

We have a strict no-theory rule.

If you've read any of my early issues of Silly Money, like How to Grow on Twitter, How to Raise Venture Capital, or How to (Not) Invest Life Changing Money, you’ll know I care deeply about being in the details. 

There are far too many armchair experts these days, typing ferociously from a keyboard when they’ve never actually done the thing.

Outliers Summit is the version where you build and get inspired in a room full of like-minded individuals.

I'll be honest: producing this is one the hardest, most stressful things on my calendar every year. 

And I’m grateful to Andrew and his team at Fibe for spearheading with all the logistics. They are truly top notch.

But there is truly nothing like being in a room full of builders bringing their vision to life. That's why we keep doing this.

Click here to learn more »

$149 for two days in that room is an absurd price for the value we aim to bring. 

It's less than most people spend on a dinner they'll forget.

Three things to know before you buy:

When the allocation is gone or the clock runs out, the early-bird window closes for good.

We are living in the strangest/best moment of our lifetime to build something that makes a real impact. 

A person with an AI stack and a distribution channel can now do what took a 20-person team five years ago. In fact, we’ll even have someone share how they are running $20M+/yr business with only a few employees and a bunch of OpenClaw agents.

That door is open right now. 

And while the people walking through it are trading notes in group chats, the rest of us are reading about it a year later.

November 5 and 6 is where those conversations are happening in person.

In just 14 days, this opportunity 30% gets expensive, and the best tiers often sell out before the cheap ones do. 

So if you've been circling the unconventional path, the fastest way I know onto that path is two days around people already on it. 

Everything I write about here, all the tax strategy and the account structures and the entity optimization, gets dramatically more useful once you do.

I'd love to see you there.

— Ankur

P.S. If you want to support this launch, please show some love on my announcement posts on LinkedIn and X. A like, comment, or share helps more than you know. Thank you 🙏

P.P.S. If you run a company that wants to get in front of 1,200+ founders and operators, partnership tiers are open and allocated first come, first served. Details on our website.

I'm writing this as myself, not as some investment adviser or broker-dealer. I'm not a tax professional. This is purely educational, not investment, legal, tax, or professional advice. Financial decisions involve risk. Please do your own research or talk to a licensed pro before acting on anything you read here. Full transparency: I'm a co-host of the Outliers Summit and have a financial interest in ticket sales.