Starting Your Side Hustle

Sun, Apr 12, 2020 6-minute read

Starting Your Side Hustle

This is a collection of notes from one of the world’s expert Side Hustlers, Chris Guillebeau. If you have not read his book The $100 Startup, you really should. It also includes important takeaways from other bloggers and authors. Wherever applicable references have been added.

Its also pretty important to define a side hustle. We are talking about small enterprises which take little to no time for setup, maintenance and daily running. We aren’t looking to start the next Facebook - though it could evolve into that but its not the intent from day one.

Notes From a Hustler

Side Hustle Questions to Ask Yourself

There is three (3) things you need to ask yourself about any chosen side hustle:

  • Does this solve a clear and urgent problem, or, does this thing make someone’s life easier in a specific way?
  • Will the idea generate income over a long time scale?
  • Is this something you like to do, or are you just doing it for the money?

If you can answer those questions in the positive sense then you have a potential option to explore.

Are There Bad Side Hustle Ideas?

Yep, and here is a list of things to look out for:

  • Part-time jobs dressed up as side hustles (freelancing),
  • Anything where you give up control of the income potential,
  • Something that exists solely on one platform or network,
  • If its not replicable (each iteration is a one-time deal),
  • Anything where you are simply trading time for money.


  • Rideshare
  • Gig economy options

The Three categories

Every hustle can be put into one of three baskets:

  1. Products,
  2. Services, and
  3. Everything else.


  • Something you give people,
  • Build once and sell once,
  • One, or multiple items for sale,
  • Books, gifts and other non-recurring items sold to a consumer


  • Something you do for people,
  • Often ongoing for either short or long periods,
  • Customer facing,
  • Courses, coaching and management are good examples.

Everything else

  • Anything where you are not selling an item or dealing with customers,
  • Affiliate commissions, arbitraging items between stores or in currency are examples.

Each of the three types will require slightly difference avenues of management and marketing. Knowing where your idea sits is important.

Idea Curation and Selection

This is the hardest part for someone like me, and probably most people. How do you first find a good idea, and if you have several, select the right one.

Patrick McKenzie said it best.

Some people profess difficulty at finding applications to write. I have never understood this: talk to people. People have problems — lots of problems, more than you could enumerate in a hundred lifetimes. Talk to a carpenter, ask him what about carpentry sucks. Talk to the receptionist at your dentist’s office — ask her what about her job sucks. Talk to a teacher — ask her what she spends time that she thinks adds the least value to her day. (I’ll bet you the answer is “Prep!” or “Paperwork!”)

That’s what it really comes down to, find a problem someone is having that you can solve. It could even be something you find annoying. Whatever it is, your next step is to assess it again the following criteria:

  • Feasibility: can I even do this thing, do I have the skills?
  • Profitability: will people buy this, or will my outlay be recovered by purchases. Include both time and financial outlay.
  • Urgency: is this a good idea in today’s world. Do people care about solving this problem today - many things have launched way before the masses respected the problem being solved.
  • Efficiency: can I achieve this quickly? What might hold me back?
  • Motivation: simply, do I really care about this? If not, you won’t have the gumption to stick out the tough moments.

Think hard on each point, write it out. Score it honestly and even discus it with close family or friends. They might see problems from a view which you are blinded to right now.

Finding Your Customer

This was a big takeaway; identify your perfect client in exacting detail and be ruthless in designing the product around them.

Ask yourself:

  • How old are they?
  • Where do they live?
  • Gender,
  • Race,
  • Country or region,
  • Unique characteristics, and
  • What challenges do they have.

Once you hone in on your target, design your product or services around them. Speak to them. Act as if the product/service is tailored (and it is) exactly for them.

You need to now speak to them, and if you have bracketed this person or persons correctly they should be hearing your loud and clear.

Idea Selected, Now What?

Time for action. What do I now need to get the ball rolling? Here is simple list for getting something out there.

  • Website with Sales, Product/Service, Contact and About pages,
  • Email list,
  • Social media,
  • Initial inventory (id applicable)
  • Payment processor

Focus only on the bare essentials. Don’t build out excess “functionality” based on what you think the customer wants. They will tell you.

A realy important part is designing your payment workflow.

How does your custome make a purchase - think this through carefully. Any hiccups on this road may lead to a lost sale, we are most likely to reject a product just before buying it.

Successful offers

At its core, each category is making an offering to its potential customer. Every successful offer has three things:

  1. Promise - why should you care about my widget,
  2. Pitch - why you need it right now,
  3. Price - and you can get it for n Now

How to craft the offer. Remember you are writing to a person, not a group or large swath of people. Each sale is form one person at a time, so speak to that person! You action words to describe the product, why its needed and why its needed right now. Always use numbers to explain statistics or prices. And, use stories that elicit happy emotions.

Pricing your Yourself

Simple, know what you are worth.

If its a service, work out what your time is worth and add a margin on that. And if its a product, calculate your expense for each item, time to create and add a profit margin.

Don’t be coy, a profit margin of less than 20% is probably going to be a profit of 0% in the long run.

Testing the Hustle

Rehearse, rehearse, rehearse. Double check your work in every aspect: does my website work on desktop and mobile, does my payment workflow work (have I manually tested in several times), does my landing page have spelling or grammatical errors?

No doubt after so long reading the same script over and over, you aren’t seeing simple mistakes. This is when its paramount we get friends or family to proof our work.

Does your offering have the following:

  • A clear offer,
  • Pitch, Promise and Price,
  • Can it be explained in one sentence (and understood),
  • How are your customers going to find you (don’t rely on one (1) method),
  • A simple payment workflow
  • And, do you as the creator have goal for this project for at least first 30 days.

Side Hustler

Creating a side hustle doesn’t have to be massive, or change the world but it needs to have several characteristics if its going to survive. Contrast each idea against this and see where you fall short, and if you can fix it.

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