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A Portfolio of Small Bets – The Course

Who is this for?

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 what to do.

You want to abandon your grueling career, but you also have a family to support.

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.

Maybe you're already working for yourself, but things are not working out so well.

What will you get out of this?

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.

This course is a presentation of a few important ideas that will help you become self-employed, but most importantly stay self-employed. 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 will have a maximum of 35 people so that we can have a high level of interaction.

You will also get lifetime access to a private Discord server where we'll continue to discuss the topics of this course, both with me and among all the alumni.

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 course.


☂️  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.


• Cohort size: 35 people max.

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

• Session length: 1.5 hours + optional after hours.

Content availability: All live sessions will be recorded and available forever.

Community: Lifetime access to a private Discord server.

Instructor: Yours truly.


• Cohort 1 [Sold out]: Nov 1-12, 2021 (Mon, Wed, Fri) @ 10am Pacific Time

• Cohort 2 [Sold out]: Nov 15-26, 2021 (Mon, Wed, Fri) @ 4pm Pacific Time

• Cohort 3 [Sold out]: Dec 6-17, 2021 (Mon, Wed, Fri) @ 11am Pacific Time

• Cohort 4 [Sold out]: Dec 20-31, 2021 (Mon, Wed, Fri) @ 3pm Pacific Time

• Cohort 5: Jan 3-14, 2022 (Mon, Wed, Fri) @ 10am Pacific Time

• Cohort 6: Jan 17-28, 2022 (Mon, Wed, Fri) @ 4pm Pacific Time

• Cohort 7: Jan 31 - Feb 11, 2022 (Mon, Wed, Fri) @ 11am Pacific Time


If none of the upcoming cohort dates work for you, you can join the waitlist. You will be the first to know when a new cohort opens up.


A Portfolio of Small Bets – The Course

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