Small Bets

Daniel Vassallo
133 ratings

Enrollment Open

Sign up now and you'll join the Small Bets community immediately.

• You have lots of ideas, but you don't really know if any of them will work.

• You're willing to take a risk, but you also don't have unlimited time to experiment.

• You want to work for yourself, but self-employment feels too risky and unpredictable.

• You want to work on your own terms, but you don't know where to begin.

• You want to quit your soulless job, but you also have a family to support.

• Maybe you're already working for yourself, but it's not working out as anticipated.

If you identify with any of the above, keep reading 👇

What You'll Get

When you enroll you get access to 3 things, all inclusive of the one-time signup fee: The community, the cohort course, and the guest classes.

🏛   The Community

You will join an active community of 3,000+ people where we discuss ideas, get feedback, share wins, and help each other. We will be your support network as you venture out in the unpredictable world of business.

You get lifetime access to our private Discord server, and there are no recurring fees.

🎓   The Cohort Course

Every month, you have the option to join the main cohort course: Building a Portfolio of Small Bets. This course is a presentation of a few important ideas that will help you become self-employed, but most importantly stay self-employed. You will learn how to tame uncertainty, filter signal from noise, take prudent risks, build a safety net for yourself and your family, find ideas and opportunities, persuade customers to give you their money, and last but not least, design a lifestyle based on your true preferences. These are all ideas that I lived first-hand as I was navigating my own challenges, and now I can help you apply them to yourself.

We will meet 3 times a week for 2 weeks over Zoom, where I'll present the core ideas and we'll discuss how they can be applied. Each cohort is limited to 45 people to ensure a high level of interaction. There will be no homework or required reading. Everything you'll need to learn will be delivered during the 6 live sessions. This will be a very information-dense program.

The course is repeated every month at different times of the day so that it covers every timezone. You are free to join any cohort, and you can even join multiple times. All sessions are recorded and available forever. There is no extra cost to join the cohort course, and you'll be able to book your spot from the Discord server.


Cohort size: Around 45 people.

Sessions: 6x live Zoom sessions over the course of 2 weeks.

Session length: 1.5 hours + optional after hours.

Content availability: All live sessions are recorded and available forever.

Instructor: Yours truly.


☂️  Making the unpredictable, predictable: Understanding the role of randomness in business. Taming uncertainty when working for yourself. How everything you have learned about succeeding in your career is invalid when randomness plays a big role. And how there's only one viable strategy for dealing with highly random payoffs.

🌲  Acquiring information under uncertainty: Probabilistic learning. Learning everything you need to know about a business, without actually knowing anything for certain. Identifying what business ideas are likely to work. Why you can succeed without knowing how you're succeeding. And why that's not a problem.

🏕️  Bias for survival: To thrive, you must first survive. Understanding the difference between survivorship bias and a bias for survival. How to avoid going bust. Learning how to succeed by not failing.

🏆  Learning from small wins: Why small wins teach you a lot more than any failure. Why you should start with the lowest hanging fruit. How to find your own low hanging fruit. And how success brings with it other success.

🍸  Recognizing luck: Exposing yourself to randomness. Making randomness your friend, not your enemy. The cocktail party approach to serendipity. Being able to recognize good luck when it happens. And how your best ideas are often the ones you can't even imagine yet.

🤩  Emerging from the unknown: How to build credibility on the internet. Going where people already hang out. Free market research. Why you should make yourself known. How people prefer doing business with other people they like. And how to be top-of-mind.

💰  Making money: How to insert yourself into money-making opportunities. How to persuade others to give you their hard-earned money, and not regret it. Why you should charge less. And why you should monetize your hobbies.

🎢  Dealing with variable income: Why variable income makes you smarter. How to activate a new part of your brain. Why small stressors breed creativity. How to avoid overworking. And why variable income gives you more peace of mind than stable income.

🏹  Lessons from hunter-gatherers: How the world you live in is completely different from the world you evolved fitness for. What your ancestors can teach you about life, work, and satisfaction. Why procrastination is a feature, not a bug. And why it would be foolish to ignore your gut feeling, even in the modern world.

❤️  True preferences: Understanding dose–response relationships, and how they apply to everything you do. Change the dose and frequency of something you like doing, and you’ll almost certainly start disliking it. Why you might be chasing the preferences of others without knowing it. And how to discover yours.

🏖️  Lifestyle design: From a life built around your work, to a work arrangement built around your life. How to incrementally move toward a lifestyle designed to match your true preferences. And how to live a life you're proud of.

🏫   The Guest Classes

Every month you can expect 3-4 live classes from guest speakers who will teach you a relevant topic based on their first-hand experience. The lineup is subject to change over time, and most of these classes will be repeated. You can join as many guest classes as you want, and these are all free of charge once you're in the community.

Current lineup:

Publishing Books & Courses on the Side by Hassan Osman

Creating an Income Stream through Real Estate by Louie Bacaj

Gumroad Crash Course by Daniel Vassallo

Getting Started on YouTube by Aprilynne Alter

What to Expect When You Go Self-Employed by Catherine Cusick

Intro to SEO by Jordan O'Connor

A Stoic Guide to Dealing with Uncertainty & Adversity by Mahmoud Rasmi

The Art of Podcasting by Espree Devora

Twitter Etiquette by Daniel Vassallo

Understanding LinkedIn by Justin Welsh

Starting a Newsletter by Louie Bacaj and Chris Wong

Making Money on Medium by Nick Wignall

Domain-First Development by Peter Askew

Self-Sponsor Your Own US Green Card by Archie Agrawal

Make $500 on Upwork by Monday by Sean O'Dowd

How to Get The Attention of Highly Influential People by Benjamin Carlson

Photography for Creatives by Steven Foster

Explaining Ideas Visually by Janis Ozolins

Building a Media Business by Arvid Kahl

And more to come.

Praise from Members

"I just joined @dvassallo’s course for cohort 5. The Discord is FULL of amazing makers. It’s like a curated group of the best from Twitter, plus more interaction and value."

Dan Rowden (@dr)

"Taking this course and joining this Discord has been an incredible learning journey. Top notch, creative, generous, engaged people coming together to figure out how to design work around life. Makings solopreneurship not so solo."

Miche Priest (@MichePriest)

"I trusted the Small Bets community and nervously became a creator on Gumroad. Three weeks later, I am humbled by the power of the internet. Over $11,000 in sales from my first info product that I was charging $15 for at first."

Louie Bacaj (@LBacaj)

"Just finished this course by @dvassallo and it's by far the best course I've ever taken, Daniel explains and dissects the process of building a portfolio of small bets thoroughly, from product ideas, randomness and luck, making money and lifestyle design."

Enrique Benitez (@bntzio)

"Just had a killer session in @dvassallo's cohort course in which I learned how to vet business ideas. Highly recommend it for those who, like me, dread the 9-5 and have way too many interests to ever want to go back."

Jason Akinaka (@jasonakinaka)

"Just finished @dvassallo's awesome cohort course. It's 9+ hours of pure informativeness & inspiration."

Takamichi Okubo (@takaokubo)

"This course by @dvassallo will show you: How to think about starting a business; How to reduce the risk of failure; How to use randomness to your advantage. Truly one of the best courses I've taken."

Hassan O. (@AuthorOnTheSide)

"Yesterday was my 1st session at @dvassallo's A Portfolio of Small Bets & I already feel wiser. School & corporate life are predictable worlds. Real world is an unpredictable world. Can't navigate the 2nd with the mindset gained in the 1st—we need a different strategy."

Basak (@hellobasak)

"For a decade, I was on a set life path. Then I decided to change it all and start from scratch. This was hard. For many months, I was lost. Till I did @dvassallo’s Small Bets course. It was one of the most transformative experiences of my life."

Gaurav Singh (@gauravsingh961)

"Proud to say I’m a graduate of the very first cohort! Definitely worth it."

Trevor O'Hara (@trevorjohara)

"You don't need another course but this by @dvassallo legit freed me from self-sabotage and procrastination. It's value dense, affordable and the community is still small and quite active."

Monica Lim (@monicalimco)

"I joined the Small Bets course by @dvassallo in April and can highly recommend it. The content is really great and inspiring. The outstanding part is the Discord community which is very active — you get lots if inspiration just by consuming the participants content alone."

Andreas Lehr (@shakalandy)

"Because of this course I finally fulfilled a lifelong dream of publishing my own book! Highly recommended."

Ergest Xheblati (@ergestx)

"Just launched my first small bet after being in this community. The lessons learned gave me much more confidence about taking risks and investing my time."

Aaron (@aaronbatilo)

"The gift that keeps on giving. You’ll never regret signing up!"

Haifa Altwaijry (@altwaijryhaifa)

"This is an awesome community. I came because of the course, stayed thanks to the community."

Daniel Rojas (@drojasug)

"Feel very privileged to have attended @dvassallo Portfolio of Small Bets course. So refreshing to hear such authentic and insightful content being shared with an interesting and diverse cohort. Highly recommended!"

Alex Konewko (@alexkonewko)

"There is no better community of solopreneurs on the internet."

Vineet Thanedar (@vinthanedar)

"Small Bets is my new idea generator. If you need inspiration and a supportive community, this is the place to be. Been into so many discord groups but only this one I actually participate in."

Shivam Dewan (@shivamdwn)

"And as a class instructor, I can easily say that the Small Bets community has been one of the most engaged groups of people I've had the pleasure of teaching! Great community there."

Aprilynne Alter (@AprilynneAlter)

"Small Bets is the most high value engaged helpful business community on the internet. We pay a one time small fee for life time access to quality connections and impactful education that transforms our lives."

Espree Devora (@EspreeDevora)

And here's an in depth review of the cohort course by Peter Elbaum:

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30-day money back guarantee

If you're not 100% satisfied with the purchase, or it's not what you were expecting, just reply to the download email within 30 days, and you'll get a full refund. No questions asked.

Last updated May 22, 2023

No recurring fees. Pay once, and you'll get:

Lifetime access
Cohort Course
Runs every month
Guest Classes
3-4 classes per month


(133 ratings)
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Small Bets

133 ratings
I want this!