Daniel Vassallo & The Art of Small Bets

Brendan Cahill
3 min readAug 20, 2020

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Who is Daniel Vassallo?

Daniel Vassallo made waves in the creator space when he published his blog Only Intrinsic Motivation Lasts: Why I quit a $500K job at Amazon to work for myself. After this blog post generate his first few thousand followers, Daniel began posting content that catered to his audience’s interests — namely audience building and AWS. He successfully launched his AWS eBook and course on how to build a Twitter audience on Sahil Lavingia’s creator platform, Gumroad. His current volume is well over 6 figures and he continually updates his audience on his various projects.

Below you’ll find the key points that will be covered in his podcast with The Creator School. Daniel was more than giving of his time, asked great questions and is always eager to connect with his audience on Twitter here. Enjoy.

Lesson 1: Create Your Audience, Then Actually Create

While it’s not impossible, if no one knows who you are you will have a difficult time selling your products as a creator. Creators should spend the bulk of their initial time building their audience. You don’t need to be on every social media platform. Just one that you can dominate.

Lesson 2: Small Bets

Don’t make imprudent and irreversible bets. Take parallel bets across multiple income streams towards the lowest hanging fruits possible. For example: trade time for dollars, build an info product, and build a subscription service concurrently and incrementally test to see which small bets are showing promise. Build a portfolio of small bets until they add up to something big.

Lesson 3: Luck Can Be Attracted

You can’t control luck but you can attract it by continually stacking odds in your favor: Having a financial runway to see out your jump into being a full time creator makes you luckier. Having an audience makes you luckier. Having valuable skills makes you luckier. Creator platforms discuss success as if it were a singular moment, but in reality is more like a marathon of odd stacking in your favor until something gives.

Lesson 4: Don’t Tweet Into The Void

If you have under a few thousand followers on Twitter you are better off building your Twitter audience by posting speciality interest niche blogs on news posting sites like Hacker News, Indie Hacker, Medium, Reddit and LinkedIn. Then, funnel those readers into your Twitter audience with a clear call to action in your posts.

Lesson 5: Story Time

People love to follow a story in progress. The more you document your experiments and bets the more authenticity you will build for your followers. Your content can be both your actual info products and the story of you creating them in parallel. You might consider writing

Lesson 5.5: Trying Is Success

The magic is in the trying. Most people live their life according to sunken costs. They sunk 20 years into a particular career and feel like it’s too late to change. But, why wouldn’t you want to design your ideal lifestyle? Why wouldn’t you want to at least try to reinvent yourself?

Bren

If you enjoyed this article, please give me a follow @brendancahill_ or @cr8rschool to see what else we’re up to.

P.S. If you enjoyed this, you might also enjoy Gumroad’s Creator Spotlight blog where Daniel goes further into depth specifically with how he leverages Gumroad to further connect with his audience.

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Brendan Cahill
Brendan Cahill

Written by Brendan Cahill

Exploring emerging trends in teaching, education, tech, business and beyond.

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