• Alyssa Barton

Side Hustle: From Idea to Income in 27 Days - Book Notes

Updated: Apr 23, 2019

Guillerbeau, Chris. (2017) Side Hustle, From Idea to Income in 27 Days. New York, New York. Crown Business.

Chris Guillerbeau’s book, Side Hustle, maps out a 27 day plan to start up a lucrative side hustle. He covers brainstorming, concept testing, launch, and then adaptive management. This is a great roadmap for those of us wishing to start making more money, now.

I must be working too hard, because right off the bat I found myself challenged by what he says a side hustle should look like.

Guillerbeau says: “High-potential ideas have characteristics like these:

  • A simple path to turn the idea into reality that you can describe in one sentence

  • Something you know how to do or can easily figure out

  • Solves a problem or makes someone’s life easier in a specific way (and that they will be willing to pay for)

  • Is low maintenance and easy to deliver without a ton of preparation or follow-up

  • Will bring in income not just once but on a recurring basis.”

(pp 23-24).

What?! No long hours? Not high maintenance? Not complicated?! The concept of quick and easy money is a challenge for my "work hard/play hard" brain.

Lots of us have been trained to think that we have to work really hard putting in long hours at a job in order to see any reward. But to get Side Hustle – and to become a side hustler - you must believe in a reality where money grows on trees. You just have to see it, grab a ladder, and get picking. But this mindset was an initial roadblock for me that I had to get over to pull value from the book, since part of me still struggles to feel that making money should be so easy.

Amusingly, later on in the book, I was somewhat vindicated because despite Guillerbeau’s advice about “low maintenance” and “simple” hustles, some of the hustles he describes seem super time and energy intensive. Those side hustles could become primary hustles – a full time job. So I think the ultimate takeaway is that great product or service takes real thought and effort to develop, but thereafter, entrepreneurs should keep things as streamlined and uncomplicated as we can so that we can use our time optimizing productivity and profit. Stick to the “K.I.S.S.” concept - “keep it simple, stupid” – where possible.

The “Side Hustle Selector” advocated by the author for “Day 6” of Day 27 – a matrix to measure the optimal characteristics of your side hustle ideas – is a super simple tool. I’ve used similar matrices in life to weigh decisions about how to spend my time, and at work to decide what policy issues to prioritize.

From my perspective, after brainstorming and selecting your hustle, the next super important part of the process is laid out in “Day 7: Become a Detective. Study what other people are doing. Then, do it better or do it differently.” (P. viii).

I think this advice is solid, and makes a lot of sense for many businesses: we need to do recon on the landscape or area we’ll be operating in and the other businesses and competitors in that space. This will help us learn what kinds of strategies are effective, what isn’t so effective, what can we do differently to set ourselves apart, and what mistakes we might avoid. Networking, inviting folks to coffee to talk about their businesses and their world, is a great way of doing this recon – in addition to good old internet stalking.

The next essential step in the process: coming up with an offer. Per Guillerbeau, an offer includes a promise, a pitch and a price.

  • “The promise: how your hustle will change someone’s life

  • The pitch: why they should purchase or sign up now

  • The price: what it costs to purchase or sign up (and how to do it).”


The promise should focus on the benefit people will get from your product; the pitch should provide all necessary details, using urgency and persuasiveness. The price should include exactly what the customer needs to do to receive it – aka the “call to action” – such as clicking, tendering payment, waiting 3 days for shipping. (P. 82).

To create urgency:

  1. Use words like “now” and “today”

  2. Respond to customers as quickly as possible. “A study by the Harvard Business Review showed that when companies replied within one hour of the customer’s original request for information, they were seven times more likely to sell to them.” (P. 84) – this is research gold.

  3. Colors on your site usually aren’t significant, but there is one rule: red text communicates urgency.

  4. “Announce an upcoming price increase, but give people enough time to make a purchase or commitment before the change goes into effect.” (P. 84).

  5. Add a countdown timer to your checkout page.

With your pitch, “there should be a purpose for every word. In good copywriting, nothing is superfluous.” (P. 85). Use words that elicit positive emotions – like joy, surprise, or reassurance – and show enthusiasm and excitement about your offer. Testimonials can elicit positive emotions, while providing social proof and helping customers see themselves as part of the story. (P. 86).

A final factor to think about before launching is on “Day 10: Create Your Origins Story.” (P. 89). “A good origins story usually features a turning point or moment of transformation in which the character evolves in a significant way or receives a mission he must complete…You’ll be much more successful if you provide your customers with a history about how your hustle came to be.” (P. 89).

One thing the author does well in Side Hustle is telling stories. Guillerbeau shares dozens of stories that folks shared with him about side hustles, stories about things that worked and things that didn’t work for them. These stories make the book worth the read in and of themselves! They help solidify otherwise abstract concepts.

For example, I connect with the story of a dude named Tanner who was going to go on a cruise for the first time. In advance of his cruise he tried to do internet research about what to expect, but he couldn’t find anything useful. After his cruise, he created his own blog answering all the questions for new cruisers that he had before cruising, in a way that would have been helpful for him. Here you get an example of a concept that’s a relatively low lift (information he learned from his cruise), but that’s highly valuable and didn’t already exist (there weren’t other blogs or resources online where folks could find answers to these questions). He just had to put it together in a way that was easy to describe, and then set up a way to get paid.

Getting paid comprises the nuts and bolts of your side hustle. When worrying about what your business will look like and how it will function, remember, “[a]sking, “is this a feasible and profitable idea”? is a much more important question than “Which bookkeeping software should I use?” Logistical questions like these are all “figureoutable,” but without a plan for generating income, you don’t have a hustle.” (P. 101).

Guillerbeau provides many great pointers for building your side hustle toolkit to ensure that you get paid and can effectively manage your money. I won’t give them all away, but here are a few:

  1. “Pay for everything you can up front.” (P. 102).

  2. “Be fast with invoicing.” (P. 102).

  3. “Whenever possible, insist on a written agreement for service work.” (P. 102).

  4. “Set aside a dedicated hustle workspace, even a small one, in your home or apartment.” (P. 103).

  5. “Pay yourself first.” (P. 103).

When determining how to price your product or service, Guillearbeau coaches to remember that “without at least some idea of what you’ll charge for your offer, you have a hobby, not a hustle.” (P. 108). The long term goal is to maximize profit, but your short term goal might be to make sure your price is high enough to make the project worthwhile for you. (P. 108). For a service you’re providing, “[o]ne good rule of thumb is that your minimum accepted hourly income should be at least what you make per hour in your day job, and probably more.” (P. 110). Note: if you’re just “breaking even,” you’re actually losing money.

Main pricing tip: use a cost-plus model to set your price. “You want it to be low enough that you don’t turn away or lose customers, but high enough that you can still earn enough money to make the hustle worth your time.” (P. 144).

Another great pricing tip: make it as easy as possible for customers to pay you! (P. 144).

When it comes to ensuring that you iron out the wrinkles from your business process, I found the author’s tips about preparing a workflow to be really valuable. These questions may help you understand what needs to happen for your business to function properly:

  • “How will prospective customers or clients learn about your idea?

  • What will happen after someone purchases or signs up for whatever you’re offering?

  • What else needs to happen in order for your customer to pay for and receive your service or product?

  • How would you proceed if the book stopped here, but you still had to launch your hustle in the next twelve days?” (pp. 136-137).

Answering these questions requires envisioning exactly how your business will run – literally, how your work will flow – chronologically, from the start of your interaction with a customer until the termination of your relationship. Creating your business workflow will help you identify steps you may have missed or that you need to work out kinks on.

For example, let’s say you open a store selling hats, and get your website up to sell these hats. Well what happens after someone purchases a hat from your website? Will they receive a “thank you” email with a receipt, confirmation number, package tracking and information regarding when they should expect the hat? If yes, you’ll have to include steps in your workflow process to design these features of your site and test to ensure that the email confirmation process functions!

Here’s a graphic example pulled from the interwebs, showing an Android App developer workflow, courtesy of: https://developer.android.com/studio/workflow:

But back to the book - which does not discuss app developer workflows.

The advice presented in “Day 16: Spend 10 Percent More Time on the Most Important Tasks” is universally truthful. Don’t get caught up in trivial details – about your business, or your life in general! “Avoid the trap of the mundane by keeping your focus on just two things.” (P. 138). What two things, you might ask? The author says by working on how you will change people’s lives, and how you will make more money! (P. 145). Great advice all around.

He then walks through publishing your offer, selling and expanding sales and services, and testing and improving systems based on feedback and results (amongst other procedural steps!) I really enjoyed the piece about A/B testing, which I think is a great concept for people trying to launch things like a new product or website design. You can perform A/B testing in order to test the efficacy of your advertising or the acceptability of the price of your product. It requires that you create two versions of the thing you want to test, and then present one version to half of your followers, subscribers, or contacts, and present the second version to the other half. There can only be one variable. This allows you test for efficacy: what percentage from each group makes a purchase? This can help you groundtruth for the more effective website design or pricing. There are 3 big things to test for:

  1. Your product or service (what you offer)

  2. Your offer (how it’s presented)

  3. Your price.

(pp. 174-175)

In closing, I’d say this book is a great starter for anybody thinking about starting a non-specific side hustle. There are appendices and resources at the end that I found super useful, and the stories are compelling – they make you think outside of the box and spurred me to have some creative new ideas!

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©2019 by Alyssa Barton