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Make Small Bets to Build a Successful Side Hustle in a Lot Less Time than You Think

by | Mar 21, 2022 | Entrepreneurs

The traditional path in life is the riskiest.

One job, one employer, no financial assets, no passive income, relying on gatekeepers, expecting a college degree to create opportunities.

Screw that.

It’s much better to bet on yourself with small bets. Now, you can do that or call me crazy. But not taking risks is a huge risk. The chance you’ll have regrets is high if you stay in the safe position.

Standing still is a risk in itself. It’s better to take risks and make mistakes so you learn powerful lessons.

If you don’t take risks you’ll be doing the same boring sh*t for your whole life and feel empty.

What many people do is take big risks. Huge mistake.

For example, a lady I know from my old job quit hers to start a business.

No backup plan, zero experience, not much in savings in case things went wrong. She ended up paying some rip-off consultant to tell her what to do.

He gladly took her money and led her along like a stray dog. Once all her funds dried up he left her out in the cold.

Now she’s back at her job.

Side hustles are the smart way to add risk. Side hustles focus on a series of small bets that produce evidence and make the path forward stupidly clear.

What stops us from taking small bets

Entrepreneur Sahil Lavingia created the term “self-reject.”

It’s where an opportunity to bet on ourselves and our side hustle appears. Instead of taking it we let fear take over.

Rather than take action and see what happens, we listen to fear and don’t experiment. No outside force is rejecting us. Nope.

We’re rejecting ourselves, which is tragic as hell.

Don’t self-reject.

The best small bet you can ever make

I say this a lot. Many people mistakenly think I’m trying to get writers to produce more writer babies. No way.

Publishing content — music, video, audio, writing, illustrations — is the best small bet you can make. Why?

Content gives you data. It’s signal that’s separate from the noise of the internet. It provides direction to your after hours side hustle.

Most importantly, content tells you what problems YOU can solve.

Once you know, you can make tiny bets in the form of potential solutions. This gives you access to possible future customers. Customers are how you monetize a side hustle.

Say yes to a lot of opportunities

It’s sexy as hell to say no. I give that advice all the time too.

Side Hustler Dakota Robertson says when you’re getting started and about to make loads of small bets, say yes to lots of opportunities to grow. Once you start growing and some of your small bets pay off, learn to say no, then.

Make the opportunities you say yes to manageable. Focus on low commitment but high willingness to go all-in if the results tell you to.

Offer a free product exactly like this

A small bet every creator should make is to put a free product on Gumroad and allow people to choose what to pay if they want.

Easlo on Twitter did this. I know several others that have done it. Free products with the option to pay helps you determine what value you’ve created (if any).

The idea is to keep publishing free content until one has enough positive data that you can bet on it with a more substantial product you charge $99+ for.

The platform arbitrage strategy any average person can do

The coolest side hustles are dumb.

A reader of mine, Andrei, pointed out you can buy an item on Craig’s List and then sell it again on eBay or Amazon for a profit.

This is known as platform arbitrage. Arbitrage is a word commonly used in finance that means to simultaneously purchase and sell something in different markets to make cashola.

Writers do platform arbitrage all the time.

They take a viral idea from TikTok and publish it on Twitter as a tweet. On one platform the value has already been extracted. But on a new platform the value hasn’t been used up yet.

Make one of your small bets platform arbitrage.

Just don’t be a dumbass and only use this strategy. It gets you started but it won’t give you long-term success indefinitely because it’s easy to copy.

The easiest small bets to make while working a job

These are the low-hanging fruit:


Use your 9-5 job skills to get one client in the same industry to pay you to do the same thing for them.

Or give yourself a promotion and consult to your one client as an expert. If you sell at your day job, consult to others on how to sell. If you’re a school teacher, consult to companies on how to do eLearning better.

Consulting is just adding a second employer to your monthly income and daring to be the expert in what you’ve already been doing for 5+ years.


Similar to consulting but less professional. The key here is you work on projects, but you’re not necessarily the expert giving advice.

There are loads of freelancing marketplaces to help you get started, whereas there are zero consulting marketplaces, so you’ve gotta use creativity to look for clients on LinkedIn.

Warning: marketplaces like Fiverr are great. Just don’t stay on them forever. Use them as a marketing channel and then get the hell out of there, otherwise you’ll be earning slave labor wages indefinitely.

Write eBooks with hidden upside

Publish them on Amazon Kindle or Gumroad.

A book is a small bet that, if it’s successful, is the opener for a more fleshed out offering. Many books become membership communities, courses, live events, podcasts, etc.

Create video courses

You’ve seen them on LinkedIn Learning, Udemy, Skillshare, and Teachable. A video course is a digestible way to learn a skill.

Yes you can learn for free via Youtube videos. The problem is Youtube videos aren’t curated and most aren’t actionable. People pay for video courses because it saves them time.

The teacher has taken the time and effort to only share the killer lessons. And hopefully they have some real experience, too, beyond curation (although many don’t, so avoid them like the plague).

Paid communities

Facebook Groups are trash. Just ask Sean Kernan haha (see here).

Any group of people can join a group chat and talk. That doesn’t mean it’ll be good or worth your time. With paid communities you’re paying, again, for curation and a way to save time.

It doesn’t have to be expensive either. I’m in a creator group that costs $90 USD per year. The small price tag gets rid of the crazies and the algorithm predictor psychos.

Why can’t you spend some time bringing people together as one of your bets?

The one many are still sleeping on

Whatever your side hustle is, it’s based on an interest. Every week you’re already consuming content because you love it.

Why couldn’t you summarize the best content you’ve discovered in a paid newsletter?

You can.

Newsletters, again, help people save time. If you can go beyond solely curation and add in a few of your own stories, you’ll crush it.

Do cohort-based coaching

You’re already a coach whether you like it or not.

You coach your dog not to poop on the Persian rug. You coach your partner to wash the dishes. You coach kids to be quiet and do their homework.

People want to be coached. Cohort-based coaching is simply coaching a group of people at the same time, live. It’s immersive. The hard part people want help with is being accountable to the stuff you’re coaching.

Passively listening is all rainbows and unicorns. Taking action is what makes the hair on your genitalia stand up.

Take coaching beyond the home.

The smartest time in history to make small bets is NOW

When there’s war, a high chance of a recession, fear, a lingering health crisis — you might think there’s enough risk already.

Don’t miss this crucial point: The people who make small bets with side hustles get unfair results during times like these.

While everyone is distracted with the news, the chance to get a head start with a side hustle increases.

A side hustle built with small bets makes you successful faster because the ability to fail and not lose everything is programmed in.

With small bets, you can’t lose. Small bets eventually produce giant gains in the near future.

De-risk your life with a side hustle.

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