Side Hustle School Classroom


Class is in session! This new weekly series will have built-in structure to it, beginning with goal-setting and going all the way through the entire process of starting an income-generating project.

Not only that, but I also hope to work with a number of listeners to actually build that side hustle they’ve been thinking about … and we’ll do that in real-time throughout the year.

It’s all free, and there’s nothing for sale. This page will be updated each week as we add new lessons. Bookmark it!

Here’s a breakdown of what we’ve covered so far. Click on any of the topics below to see a summary and the link to listen to that episode:

CLASSROOM #38: Revisiting Key Lessons (Part II)


Today and two weeks ago, I thought we’d do a bit of a reflection on the year known as 2020. I don’t mean the year in general, but the Classroom series. My goal with this series was to complement the in-the-trenches stories with a number of more practical “go and do this” lessons for those who are just getting started.

We’re more than 1,400 episodes into the show now, and lots of people have joined in along the way. Others have come and gone, maybe focussing more or less on your side hustle depending on what else is going on your life. So when you need to do something specific, such as set up an affiliate program or review your offer before it goes out to everyone, or something else, you can get that info from this series.

So what have been a few highlights, first from my perspective but more importantly from the perspective of our listeners?


Listen back to these important, Classroom episodes:

  • -> Dealing with Unsupportive Family Members [Ep. 1269]
  • -> Create Content By Answering Questions [Ep. 1304]
  • -> The 6 Factors of Persuasion, Part I and II [Ep. 1199] and [Ep. 1206]
  • -> Who Are ‘Your People’? Understanding Psychographics [Ep. 1255]



CLASSROOM #37: Revisiting Key Lessons (Part I)


Today and two weeks from today, I thought we’d do a bit of a reflection on the year known as 2020. I don’t mean the year in general, but the Classroom series. My goal with this series was to complement the in-the-trenches stories with a number of more practical “go and do this” lessons for those who are just getting started.

We’re more than 1,400 episodes into the show now, and lots of people have joined in along the way. Others have come and gone, maybe focussing more or less on your side hustle depending on what else is going on your life. So when you need to do something specific, such as set up an affiliate program or review your offer before it goes out to everyone, or something else, you can get that info from this series.

So what have been a few highlights or key lessons, first from my perspective but more importantly from the perspective of our listeners?


  • Avoiding Mistakes in the Idea Phase [Ep. 1129]
  • Finding Time to Work on Your Hustle [Ep. 1171]
  • It’s Not Just What You Say [Ep. 1143]
  • Don’t Listen To This Boring Episode [Ep. 1178]



CLASSROOM #36: Troubleshooting—What If It Doesn’t Work?


Today, let’s look at the topic of troubleshooting. What if your idea, product, or service doesn’t work out? How can you allow this to be a minor misstep instead of a permanent failure? Better yet, how can you turn that misstep (or even a disaster!) into positive momentum for your next attempt?

First things first: face the problem! Don’t bury your head in the sand, and don’t just keep trucking along thinking that something will change on its own.

“They say time changes things, but mostly you need to change them yourself.”-Andy Warhol


No one has a perfect record in the world of ideas. The next time you experience a misstep, consider what you can do differently next time … and don’t wait long to get started.



CLASSROOM #35: Sourcing Products Using Alibaba


Today, let’s look at the topic of sourcing products using Alibaba and Alibaba Express. Specifically, I’m talking about buying something from overseas (most likely an East or Southeast Asian factory) and reselling it in your country. Is there an easy way to get started with this?

What is Alibaba and Alibaba Express?

The Alibaba Group controls the largest online marketplace in the world—and yes, that includes Amazon.

It’s a directory of manufacturers and items for sale in bulk, predominantly from China. You can peruse the listings, contact vendors, and place orders directly.

You don’t need to be a big business or even a business at all to purchase from these sellers, Alibaba provides a number of protections for both buyers and sellers (like eBay), and in a lot of cases, there are low minimum quantities so you don’t have to invest a lot upfront.

Alibaba is B2B only, Alibaba Express is B2C. There is some overlap, but generally, the prices will be higher on Alibaba Express—that’s because it’s easier and more consumer-friendly, with lower minimum order quantities. I’d recommend if you really want to get into this, you focus more on Alibaba, just be aware there’s a learning curve.

Listen to today’s episode to learn more…


Consider buying something for resale. Visit and identify at least two items you think you could purchase and then resell for a profit.





CLASSROOM #34: Dealing with Customer Complaints


Today, let’s look at the topic of … customer complaints. I get asked about this all the time, especially from anyone who wants to share some kind of message online. They’re worried about criticism, and if they sell something, they’re worried that people won’t be happy about it.

So let’s go through a few examples from the archives and consider how our case studies have dealt with some challenges, as well as what we can learn from that experience.

First, as I looked through the archives, I was reminded that so many moneymaking projects start out of a complaint or dissatisfaction.

  • – An operations manager who moves to a new state and wants to find a Mandarin-speaking nanny for her daughter, then ends up starting a network to connect people like her
  • – A programmer who was always forgetting his friend’s birthdays wrote a script that will check Facebook for him and post “Happy birthday” messages on his behalf – then he created a web browser extension called Birthday Buddy
  • – Tattoos to cover up surgical scars
  • – Two Women Create Swimwear Brand for D-Cups and Up

And so many more! So it’s obvious that complaints can be an interesting genesis or inspiration. But what about when someone is complaining about your business?


Think of two ways to make your customers happier.


CLASSROOM #33: Transitioning Between Projects


Today, let’s look at the topic of … transitioning between projects!

How can you transition between projects (or a job and a side hustle) without constantly losing your flow—and how can you start a completely new project without just creating more “stuff” to worry about?

There are two parts to this:

1) The daily or frequent transition between projects you’re actively working on (your day job and side hustle, your coaching call and that book you’re trying to write)

2) The transition between old and new projects (when you start something new and move on in some fashion from something old)


Understand your ideal working conditions, learn to transition in a way that makes sense to you. Also, spend more time doing deep work!


CLASSROOM #32: How to Ask for Referrals


Today, let’s look at the topic of … selling a food & beverage product!

The first thing to note is that this industry poses both unique challenges and opportunities. Let’s not make light of the challenges, because they aren’t small!

First, this industry is more highly regulated than lots of others. For many projects, you don’t need any special licensing at all, but for food, you usually do.

Before you do anything at all in this space, do some research about “cottage laws” in your area. These are regulations that initially come from British common law and have been integrated in other parts of the world, including the U.S. and Canada.

The idea is to make a distinction between the Joes of the world who are selling their oat bars and the kind of business that needs more inspections and approvals. They vary a lot, but often it has to do with the volume of product you are selling.


Interested in an F&B side hustle? Look up the local laws and regulations for your area. You might also want to see if there’s a food incubator or local organization that specifically serves aspiring foodpreneurs.


CLASSROOM #31: Selling a Food & Beverage Product


Today, let’s look at the topic of … how to ask for referrals!

Where can you find the most active, efficient, and relevant people to evangelize on your behalf … sometimes even for free? The answer is: they’re right in front of you: your existing, active, and happy customers!

Generally speaking, most people like to be helpful. They like to connect their friends and peer network with resources that could benefit them. So this group—your current customers or clients—are the most likely candidates to eagerly bring more people your way.


If you have customers, ask them for a referral! If you’re still working on your idea, consider how you can actively build this into your process.


CLASSROOM #30: Crowdfunding Basics & Best Practices


Today, let’s look at the topic of … crowdfunding!

Why consider a crowdfunding campaign? One: money, two: other forms of support.

Some projects are better suited for crowdfunding than others. Manufacturing is the classic category. There are hard costs, it’s relatively easy to show the path to completion and why you need the money, and backers like the idea of being part of making something.

These days there are consultants who advise crowdfunding campaigns, but without getting into a ton of detail, here are a few important things to know.

Crowdfunding Basics & Best Practices

  • 1) Be prepared to study up.
  • 2) Give yourself a long timeframe if possible.
  • 3) Line up early support.
  • 4) Carefully consider incentives and tiered rewards
  • 5) Communicate often – if it feels like you’re overcommunicating, great! Keep doing it.
  • 6) The most important days of the campaign are the first and the last.
  • 7) Having a good video is key.
  • 8) Set a real goal – take some kind of risk.


Think about something that is weighing you down or causing you stress, and consider if there’s something small (or big) you can do to remove it.


CLASSROOM #29: Set Up a WordPress Website


Today let’s look at setting up a WordPress website. This can be very simple, or like many simple things in life, can be made very complicated. Let’s try to stick with the simple.

The goal of this tutorial is to show you how to set up your first website in a short period of time and without spending a lot of money. Your site probably won’t be beautiful or amazing at first, but that’s okay—done is better than perfect, and you have to start somewhere.

The first year of Side Hustle School, I made a page about how to set up a website in 90 minutes. This turned into one of our most popular tutorials, so I wanted to revisit and update it here.


Set up your first website using WordPress OR make two improvements to your existing website.


  • Looking to purchase a domain name and setup hosting? Go to for this special offer for Side Hustle School listeners.
  • Once you’ve got your domain name and hosting, install a WordPress theme. Remember, is free – totally free! It’s different from, which offers paid solutions.


CLASSROOM #28: Create Content By Answering Questions


I was going to call this episode “Simple and Effective SEO Tips.” If you start to learn anything about SEO, you’ll find articles all about keyword research. This can be very helpful in understanding your ideal customer—what are they searching for? What specific words do they use? How do they phrase the searches?

Your goal is to find something a lot of people are searching for that doesn’t have much competition.

For example, if you sold a guide to solving the difficult NYT Sunday crossword, and you found a bunch of people searching “How do I solve crossword puzzles?” but not a lot of results, that would be great. You might want to create a page on your website title “How to Solve Crossword Puzzles.”

But let’s go beyond merely knowing how to create a page or two based on what you learn. One of the things you’ll notice is that people ask questions when they use search engines.

Well, guess what? If you’re struggling in coming up with topics to write about (or otherwise use for content creation), this is your answer.

You can create content based entirely around answering questions that people are asking. It helps you brainstorm, it gives you a task, and it ensures that what you’re working on isn’t going to be completely irrelevant.

Listen to this Classroom episode to learn more…


Look up one word or phrase using the Google Keyword tool and see what people are searching for. Does it give you any ideas?


CLASSROOM #27: Forecast Your Profit on a Napkin


Two reminders as we jump in today:

  • First: Your side hustle must have a clear plan to make money.
  • Second: if you’re having a hard time deciding on an idea, it helps to consider each of your ideas according to a few criteria. I’ve done a whole episode on this topic – you can access it on that page.

So how do you figure out which idea has the most profit potential? You can do that by making a projection.

By forecasting profit and expense with a simple estimate, you’ll be able to make decisions for your hustle with far more confidence.

Expected income – Expected expenses = Projected profit

Of course, to get the critical information of “How much money can I make with this idea?,” you’ll first need to make those estimates for income and expenses. To come up with your estimates for each factor, you’ll usually need to identify several other variables.

Listen to this Classroom episode to learn more…


Create a simple Profit Potential estimate for one of your ideas.


CLASSROOM #26: How to Avoid Getting Stuck


Today, let’s talk about how to avoid getting stuck.

I had a conversation with my publisher about this recently. A lot of people never start… somewhere along the way, they get stuck.

To be stuck means you’ve reached an impasse, an obstacle or limitation that hinders your progress.

To avoid this, you need to be able to think differently… and of course, you need to choose to take action.

This is as much of a mental block as a practical one. When you’re stuck, you go into a feedback loop that reinforces any negative thoughts you might have about yourself. That’s why it’s not just about oh, I can’t get people to follow me on Instagram or I can’t figure out how to set up my website.

Being stuck is usually more of an internal issue.

First, understand that a lot of people go through this in different ways. Here are five tips that might help.

  • 1) Identify problems in advance
  • 2) Always know the next step
  • 3) Impose an artificial deadline
  • 4) Look for an alternative way forward
  • 5) Try something totally different

Listen to this Classroom episode to learn more…


Try to head off a problem at the pass. Look ahead and identify something that might trip you up—then try to find an answer for it now.


CLASSROOM #25: Dealing with Unsupportive Family Members


Welcome to a new week and a new Classroom episode!

For the first half of the year, this series focused on everything you need to do to build your first income-generating project. Last week I did a recap or summary of what those episodes included. Going forward, we’re going to focus much more on marketing, or getting the word out about this new product or service!

Aside from questions about creating your first project, I hear more questions about marketing than anything else.

However, this week, I have something different for you. I want to talk about the question: What if your family doesn’t support your side hustle?

This is also a common question—not as common as the others, thankfully, but it’s true that not everyone has a supportive network around them all the time. You might be around people who don’t understand why you want to do this, or they think it’s not possible, or they’re just downright negative.

So what do you do?


Consider if there are any negative or discouraging voices in your life, and then consider what you can do to block them out.


CLASSROOM #24: Halfway through the year! Let’s review.


We’ve made it to the middle of 2020! Let’s review what we’ve covered in the Classroom series so far, and prepare to move to a major focus on marketing for the rest of the year.

We are now halfway through the year, and I thought it would be good to look back at the CR series. I want to make a few changes to it going forward.

On this newly updated Classroom page, you can scroll back and take a look or a listen to anything you might have missed or that seems particularly relevant to you.

I always encourage you to use your time well—if some of these topics are basic, then skip them. We still have two new stories or case studies each week, along with all of the interactive new features such as Q&A and TBT episodes.

People tend to have one of two problems:

1. They don’t have an idea

2. They don’t know how to bring that idea to life.

So a lot of what we looked at in the first two months of the year was about what makes for the right idea (a profitable one) and how can you develop the skill of identifying lots of ideas?

The second two months was mostly about how to get your idea ready – everything you need to do to create that product or service.

As you move from choosing an idea and then developing your product to focusing more on marketing, you’ll want to make sure you’re well-positioned to give people what they really want—not just what they say.

How can you reach the right people? That’s something else we looked at: your ideal customer, the single person out there who best represents many others who are going to line up around the block to buy from you … or crash your website with so many orders … or maybe just buy slowly, but in a way that allows you to grow and do more of what’s important to you.


CLASSROOM #23: Who Are “Your People”? Understanding Psychographics


You’re probably familiar with Traditional Demographics such Age, Location, Sex/Gender, Race/Ethnicity, Income. If you think of a market of 35-39 year-old women, that’s one target market based on traditional demographics. Of course, you could get more specific: 35-39 year-old women with college degrees who are interested in crafting and live in the Atlanta area, for example.

If you’re catering to a clear demographic, then this is easy. If it’s a local business like an ice-cream truck, you want to position your truck near a school, or at least in a residential neighborhood with a lot of families.

But many businesses aren’t like that. These days, it’s easy for anyone to market to people based much on interests, passions, skills, beliefs, and values. You could call these the New Demographics, or some people call them Psychographics.

How can you figure this out? In this episode, we’ll look at three examples and three lessons we can take from them.


CLASSROOM #22: Create a Powerful Origins Story


Let’s talk today about being your own superhero!Maybe you didn’t realize it, but you were born on an alien planet, bestowed with incredible abilities and the calling to help a lot of people—but you also had much to overcome along the way.

Okay, let’s back up a little. What is an origins story?

The phrase “origins story” comes from the world of comic books, whose artists construct histories of how superheroes or villains gain their powers and turn into the unique characters they’re known for. 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.

Unless you’re selling a completely generic product (and you probably shouldn’t be), you’ll be much more successful if you provide your customers with a history about how your hustle came to be.

Like a comic book superhero, your side hustle needs a history. When I review About pages on websites, I often look closely at the story being told. What’s this all about, and why does it matter?

Conveniently, there’s a formula you can use to make this easy. If you have the SIDE HUSTLE book, it’s on Day 10 in a simple fill-in-the-blank format.

But if you don’t have it, I’ll talk you through it:

I’ve always been interested in ________________________ ________________________________________________, so I decided to try __________________________________ _________________________________________________ _________________________________________________.

I was frustrated by _________________________________ _________________________________________________ and knew there was a better way. I made _______________ _________________________________________________ to help other people with the same problem.

I started this hustle because I noticed __________________ _________________________________________________. There didn’t seem to be anyone else doing anything about it (or the existing businesses were missing something important), so I made _______________________________ _________________________________________________ _________________________________________________.


CLASSROOM #21: Using Automation & Workflows


How can you make a manual process easier? It starts by answering the question: how can I do this better?

For example, I’ve been using a tool called Keyboard Maestro. I take a lot of screenshots, and sometimes I need to copy and paste the screenshot into a Keynote presentation or other program. I used to have to take the screenshot, save it to Dropbox, and then open the file manually before copying over the image to Keynote or whatever.

Finally I realized, this should be simpler. I used Keyboard Maestro to create a single button to do what was taking me at least six clicks before. Now I get really excited about taking screenshots!


CLASSROOM #20: Design a Smart Launch Strategy


Let’s talk about product launches and designing a smart strategy for them!

Disclaimer: I think it’s just as important to think long-term. I’ve seen a lot of people make the mistake of focusing only on the launch. This is especially true with books, where a lot of people buy the book in the first week, but then it sinks like a stone.

At the time I’m recording this, we’re also in the midst of COVID-19. And guess what? People aren’t responding to product launches very well. This is all the more reason why it’s better to think long-term.

That said, this Classroom episode is about launching, specifically how to design that smart launch strategy.


CLASSROOM #19: Pros and Cons of The Funnel Model


When someone places an order … what comes next?

First of all, there’s much celebration! But then presumably, there’s some amount of work.

A future episode will look at workflows in more detail. For now, let’s just consider some really basic steps you might need to take.

This is important because a clear process reassures buyers that they made the right decision. You want to communicate the message: “You’re in good hands. This was a wise decision that you just made.”

It’s also important because if you invest time and energy on the front end, thinking through product delivery, you can save a lot more time and be more efficient in the long-run.

For years I was terrible about this. I finally forced myself to not launch anything unless I had a clear plan for follow-up, delivery, execution.

So let’s consider how this might work for you. I’ll give you two examples, one for a product and the other for a service.


CLASSROOM #18: How Will You Fulfill Orders?


Today I want to talk about something you may hear about if you follow the world of internet marketing—and if you don’t know what that is, that’s okay … you don’t need to!

I could never build a proper funnel because of my personality. Is this a weakness? I’m not sure – I honestly go back and forth about it. But in the end, I’m not willing to sacrifice some of the things I enjoy doing in order to build the perfect multi-million dollar funnel.

This also requires some amount of scale. People who do this well almost always work with contractors and eventually employees. If that’s what you want, obviously that’s great.

But I know our audience, and I know that for every person who identifies with that goal, there’s at least one other person who would say “I don’t want that.”

That’s why I try to present you with a range of different ideas and examples, so that you can figure out what’s best for you.


CLASSROOM #17: Questions to Ask Manufacturers and Vendors


If you end up working with a manufacturer, overseas factory, or some other vendor—what do you need to know?

Throughout the history of the show, we’ve heard from a number of individuals who have braved the waters of international manufacturing. It’s much, much easier than you might think. These days, thanks to the wonders of technology and globalization in general, platforms like Alibaba allow you to quickly filter through thousands of options in search of the best partner for your idea.

One of my favorite stories is the dice-throwing pastor (Ep. 352: Role-Playing Pastor Rolls The Dice On $2800/Month Hustle) who is feeling burdened with all of his side jobs, then gets the idea to make and sell custom dice for fellow tabletop gamers.

So what do you need to know?

Most importantly, you want to ask specific questions.

The information you’re looking for is: are they reliable, will they be a good partner, are they financially solvent, etc. —but those questions will usually result in a positive answer regardless of whether that’s the real story or not. (“Of course I’m reliable!”)

I’ll give you a list of those questions in this episode, but here’s something else that’s critical: however you ask, you want to make sure they understand what you’re looking for.

A lot of manufacturers and vendors will just say “yes, we can do that” meaning “we’ll figure it out later.” You want to make sure they understand up front—otherwise you’ll have an issue with quality, timeliness, or cost … maybe all three.


CLASSROOM #16: The 6 Factors of Persuasion, Part II


Last week we started our conversation regarding persuasion talking about the first 3 parts; authority, commitment and consistency, and social proof. In today’s episode we’ll focus on the final 3 parts of persuasion; liking, reciprocity, and scarcity.

Remember: If you can learn some basic psychological principles of selling… understanding why people make purchasing decisions, it’s something you can apply over and over for the rest of your side hustling journey.

It’s a lot like learning some basic tech skills. You don’t need to be a programmer, but if you can learn your way around WordPress and how to set up an email campaign, etc. – you’ll have a major advantage over the previous version of yourself that didn’t know those things.

Think of it as Minimum Viable Knowledge, or high-impact knowledge. A little knowledge goes a long way.

And yes I did say selling! It’s okay to do that, after all. Sometimes I worry I’m too soft … it’s okay to make money. I want you to be able to sell your products and services, present your offers with confidence. Because, after all, if you’ve made something that can help people, you’re doing them a disservice if you don’t try to get it to them.


CLASSROOM #15: The 6 Factors of Persuasion, Part I


This week and next week we’re going to talk about persuasion. This is a topic that is so important it’s divided into two weeks. If you can learn some basic psychological principles of selling… understanding why people make purchasing decisions, it’s something you can apply over and over for the rest of your side hustling journey.

It’s a lot like learning some basic tech skills. You don’t need to be a programmer, but if you can learn your way around WordPress and how to set up an email campaign, etc. – you’ll have a major advantage over the previous version of yourself that didn’t know those things.

Think of it as Minimum Viable Knowledge, or high-impact knowledge. A little knowledge goes a long way.

Persuasion is the art of getting people to believe or act in the way you want them to. As applied to marketing, it’s effectively the art of making the sale … which begins with convincing people that they NEED (not want) what you are selling. The more they feel that way, the less effort will be required to get them to say yes.

How you do this is both an art and a science. Let’s talk mostly about the science. Cialdini and other researchers discovered a few specific characteristics that most influence purchasing decisions. All things being equal, the more of these characteristics you have in your offer (and the stronger they are—it’s not just about them being present), the more people will respond.

We’ll look at all of them in some detail, both what they are and how you demonstrate them in your offer, and any of your messaging (sales copy, emails, etc.). You want to think about these things as you create both your product and your pitch.


CLASSROOM #14: The Power of Your Own Small Army


This week I’d like to discuss a topic that is dear to my heart. It’s highly relevant to the current climate of the world, yet it’s always relevant (timeless!) to those who want to advance a message or sell a product or service without being overly sales-y and in a way that is relationship-focused.

I call this The Power of Your Own Small Army, and the best way to talk about it is through a story.

Way back in the day, when the cavemen began to emerge from the stone age and I set up my blog on WordPress, I didn’t know much at all about blogging. I followed people like Gretchen Rubin and Leo Babauta and a few others, but I didn’t have a lot of resources, I wasn’t really sure what I wanted to write about, and I certainly didn’t have a business plan.

So what I did was decide to build this movement, one person, at a time. The only business goal I had was getting people on my email list and eventually write a book … I didn’t really have anything to sell them.

Well, I set up that blog and people slowly began subscribing, and for every one of them, they got the usual “Thanks for subscribing” message. But then I also sent them another personal note that said “Hey, this is Chris – I saw you joined my blog The Art of Non-Conformity. That’s awesome! Let me know what you think and if I can help you with anything.”

I did that for about a year and a half or however long it took to get my first 10,000 subscribers. Finally, I stopped, but during that time I had gotten to know at least a little about probably 3,000 or more of that first group … which was very helpful!

Then when I went on my first book tour, I adopted a similar strategy by visiting every U.S. state and every Canadian province. I remember those gatherings very well, especially the smaller ones that didn’t have a lot of people. All along the way, I got the chance to have group and individual conversations that then set the path for the next few years of what I did.

This is all about a model I call the power of a small army.


CLASSROOM #13: Side Hustle Sprint! It’s Time to Break Out the Duct Tape


Last week was all about business licenses, bank accounts, and record-keeping.

This week I’d like to pose a question as a thought experiment: what if you had to launch a project in two weeks or less?

This is not just theoretical, at least for me: In my world, my new book THE MONEY TREE comes out in just eight days, so perhaps that’s why this topic has been on my mind. I try to live out the values I teach here on the show, and when it comes to publishing I have an unmovable deadline. Ready or not, the day arrives, and I have a limited window to make it really count.

So when it comes to working on a crunch to launch your project, there are a few questions you need to answer:

  • What do you really have to do?
  • What part of this are you currently procrastinating around?
  • What can you let go of?

The answers to these questions will drive the process for this exercise.


CLASSROOM #12: Don’t Listen to This Boring Episode


This week I’d like to look at a really sexy topic, or series of topics: Business licenses, bank accounts, and record-keeping … like I said, these are the things that get people really excited.

If for some reason you think these topics are boring, well, here’s the trick: if you get a few easy things right in the beginning, it will be much less stressful moving forward. Then you don’t really have to think about them again! I’ll give you eight recommendations in this episode.

Here are a few recommendations that just about everyone should follow —

  • Get a bank account that’s just for your side hustle.
  • Similarly, get a separate credit or debit card you use only for expenses associated with your hustle.
  • Be fast with invoicing.
  • Set aside at least 25 percent of your hustle income for taxes.
  • Legal structure: operating as a sole proprietor is perfectly acceptable for many hustles.
  • Right from the beginning, set up a very simple accounting system.

Two recommendations that are somewhat psychological, but still very helpful:

  • If at all possible, set aside a dedicated hustle workspace, even a small one, in your home or apartment.
  • Once you’re making money, pay yourself first.


CLASSROOM #11: Finding Time to Work on Your Hustle


This week I’d like to answer a question I hear over and over. No doubt some of this year’s callers will ask and have asked in different ways. We’ll consider those questions situationally as they arise, and I’ll try to offer some general advice here.

Here are 7 things you can do to help you find the time and energy to make progress…

1. Don’t “just start” … just stop. Stop doing things that waste time and you don’t enjoy. Make a to-stop-doing list.

2. Know what you’re going to do before you sit down to work. This will help you avoid getting sucked in and going away later asking yourself, “What did I actually do during that time?”

3. Maintain a “this matters” list. What helps you generate new business or otherwise make a measurable difference in your business? What helps you get closer to launch? What’s holding you back and how can you fix it? All of that goes on the “this matters” list.

4. Work on that list every day, even if only briefly. Do this before you do emails, social media, or any administrative tasks.

5. Outsource, delegate, or otherwise “disappear” one task each week. Ask yourself: does this task really need to get done?

6. Make small sacrifices without canceling everything you enjoy. Don’t skip your favorite TV show … but if you have 17 favorite shows, you might need to pull back.

7. Maintain boundaries with your friends and family. Ask them to give you the space you need!


CLASSROOM #10: The MVP of Minimum Viable Products


This week, let’s create a Minimum Viable Product: “a version of a product with just enough features to satisfy early customers and provide feedback for future product development”

Remember the lesson of thinking about offers. What is the promise, pitch, and price of each of them?

  • How will it change someone’s life?
  • Why should they buy now?
  • How much does it cost, and how can they make a purchase?


CLASSROOM #9: Give The People What They Want


In recent Classroom episodes, we’ve looked at different side hustle ideas—where they come from, categories of different ideas, how to decide between competing ideas, and so on. Last week we looked at the three elements of every compelling offer: a promise, a pitch, and a price.

Essentially we’re going from thinking about ideas to designing real offers. This episode seamlessly continues the thread line. It’s called Give The People What They Want (not what they say they want).

Alternatively, you could call it Give Them the Fish.

The other day (Ep. 1152) I mentioned the story of the spreadsheet guy, which originally came from The $100 Startup. This got me thinking about something else from that book: how important it is to understand what your customer really wants, which might be different than what you think, or even what they say.

It’s all the fault of the old parable: “Give a man a fish and he’ll fish for a day. Teach a man to fish and he’ll fish for a lifetime.” This might be a good idea for homeless fishermen, but it’s usually a terrible idea in business. Most customers don’t want to learn how to fish. We work all week and go to the restaurant so that someone can take care of everything for us. We don’t need to know the details of what goes on in the kitchen; in fact, we may not even want to know the details.

The customer is NOT always right. Listen to everything, but make your own decisions.

In fact, one of the most powerful things you can say to a customer or potential customer who is dissatisfied is “You know, it sounds like what we’re offering isn’t a good fit for you. I hope you find something else that serves you better.”


CLASSROOM #8: Three Elements of Every Strong Offer


In recent Classroom episodes, we’ve looked at different side hustle ideas—where they come from, categories of different ideas, how to decide between competing ideas, and so on. Two weeks ago we began building our Roadmap to Launch, and last week we looked at the first part of a series on branding.

This episode is called Three Elements of Every Profitable Offer.

  • The Promise: how your hustle will change someone’s life
  • The Pitch: why they should purchase or sign up now
  • The Price: how they can purchase or sign up

First – why think about offers? Again, it’s because consumers respond to offers, not just “here’s a product or service.” Even if you’re selling to companies (B2B), there’s still a person at the company making the decision. Don’t wait to think about these important elements.

The promise should change your customer’s life on some measurable level. Go big and keep your attention focused on the benefit people will receive from it. Then, craft that into a short statement that attracts attention and makes the benefit to customers immediately clear. “A short, daily podcast that brings you daily ideas for making extar money” is the promise of this show.

The pitch should provide everything someone needs to know, without getting bogged down in a bunch of irrelevant details. A key part of the pitch is timeliness or urgency. Your offer is great, but great isn’t good enough. Why should they take action right now?

Lastly, the price or CTA (call-to-action) tells prospects not only how much it costs but also what they need to do.

The call-to-action should tell prospective customers or clients exactly what they need to do. Examples of call-to-actions include: click this button, call this number, sign up here, etc. It should be easy and obvious.


CLASSROOM #7: It’s Not Just What You Say, It’s How You Say It


In recent Classroom episodes, we’ve looked at different side hustle ideas—where they come from, categories of different ideas, how to decide between competing ideas, and so on. Last week we began building our Roadmap to Launch: all the things you need to do before you can debut your project.

This episode is called, It’s Not Just What You Say, It’s How You Say It.

Why aren’t we talking about shopping carts? Instagram ads? Or – wait – why aren’t we building out those nuts and bolts we talked about last week.

We’re still all about nuts and bolts, and we’ll get to marketing much more in the second two-thirds of the year, but because branding and messaging are part of product design … it’s critical to think about the message you’ll be presenting.

This shouldn’t be an afterthought; it’s something you consider as you work off that roadmap and as you complete those tasks.

Here’s a key point: we make purchasing decisions based on emotion more than logic, and the way you appeal to emotion is by leading with benefits.

So from the beginning, you want to think about some of the questions we’ve covered already:

  • Is it a product or service?
  • Who is my ideal customer?
  • How will I go from idea to offer?

But also: what are the core emotional needs that I will meet, and how will I communicate that fact?


CLASSROOM #6: Roadmap to Launch (What Lies Ahead)


In recent Classroom episodes, we’ve looked at different side hustle ideas—where they come from, categories of different ideas, how to decide between competing ideas, and so on.

This episode is called Roadmap to Launch: What Lies Ahead. Let’s preview all that’s to come as we go from your idea phase to the preparation phase to the launch phase.

Benjamin Franklin said: “By failing to prepare, you are preparing for failure.” I don’t want you to fail, so that’s the last time I’ll use that word today.

So let’s assume you believe in the value of planning. Knowing what you need to do in advance will save you so much time as you go along. Often you have limited time and energy to work on your side gig. It greatly helps to be able to refer to a list and remember, “Oh, right – that’s what I need to do now.”

The first thing you should do is:

1. Visualize an outcome.

I don’t mean metaphysically speaking, I mean nuts and bolts. Imagine that your idea works as well as you’d like it to, and maybe even more. What does that look like?

Do you have customers? Clients? Are you selling your product online? Are you interacting with potential customers? Are you trying to grow your following?

Whatever it is, imagine the final outcome of that process. You have the customers, the clients, the followers.

2. Ask: what has to happen for that to occur?

This is meant to be very practical, so let’s keep it grounded. Are customers buying something from you online? Well, then presumably you need a website and a shopping cart. Or maybe you’re selling through a third-party platform—you still need an account there, and of course the product itself.

If it’s a service business, will you have a workflow of how to provide a consultation? (We’ll talk about that later.) Will you need an online calendar for people to schedule appointments?

There could be all kinds of things that you need, and you might not know what all of them are until you’re in the process. Still, if you visualize that outcome, I bet you can at least identify several of the major tasks that you’ll need to tackle in the coming weeks and months.

Focus on what’s essential, not what’s optional. If you try to accomplish all the things you could do, you’ll never get off the ground. What do you really need to reach your objective?

3. Write this down! Document your plan of action.

You need a plan of action. Use a journal or paper notebook, use your favorite digital notetaker, or even dictate your roadmap using a voice memo if you’re on the go and you like that method.

Nothing is set in stone, but this will give you something to come back to as we go along. It will be a checklist, a guidepost, and a to-do list.


CLASSROOM #5: Avoiding Mistakes in the Idea Phase


Last week we talked about deciding on an idea. I showed you a tool, the Side Hustle Selector, that you can use to eliminate ideas that aren’t a good fit for you at any particular time, as well as reduce your indecision.

Of course, no tool can help if you just want to remain stuck … so don’t do that! Join us on the road to implementing profitable ideas, which is what we’ll spend two-thirds of the year on. (Maybe even three-quarters, or whatever the next estimation is … but you don’t come to me for math lessons.)

Once you’ve got your idea, I want to save you even more time because I’ve seen (and experienced myself) that people tend to make the same mistakes over and over.

What are those common mistakes? Let’s jump right in. I’ll show you seven of them, and as a bonus – you’ll hear how to avoid them.

  • Trying to serve all the people, all the time. It’s not possible to do this well! Serve fewer people.
  • Not having a clear revenue model. Remember what I said about “How will your idea make money?” And if you don’t know, don’t proceed. Think long and hard about this question; it’s not optional.
  • Unclear messaging. Do you have an elevator pitch? If it starts with “It’s a long story…” or “It’s complicated…” that’s not good. Most likely, your idea isn’t complicated—you just can’t explain it well. Maybe you don’t know it well enough.
  • Not thinking enough about fulfillment. Later I’ll teach you about workflows, and designing a systematic process for how buyers can have a well-executed experience. For now, just think through how the logistics will work for whatever it is you propose to sell: how will you sell it, how will people pay for it, and what needs to happen for them to receive what they pay for?
  • Not having a good answer to the question “Why should anyone care about this?” This is one of those hard truths: the more you can be coldhearted about your own idea, the better job you’ll do in polishing it to make it more compelling and interesting. I want you to believe in your idea, but put on your skeptic’s hat now and then to really understand any objections or weaknesses.
  • Not asking, “What if this succeeds?” You may have already thought about the possibility that your idea fails. That happens … but you should also think about what happens if your idea succeeds and works really well? Will you have problems if its too successful? How can it grow if it takes off right away?
  • Not having any sense of urgency or scarcity. You want potential buyers to think, “I need to have this now,” not “That’s interesting, maybe one day I’ll come back and look at it.”


CLASSROOM #4: Deciding on an Idea


Last week we talked about different categories of side hustles, specifically identifying the difference between products and services. Before that we looked at where moneymaking ideas come from.

What if you have a lot of ideas? It might sound like a good problem to have … but of course it’s still a problem, especially if the presence of so many ideas prevents you from making decisions and focusing.

Side Hustle School is designed for busy people who don’t have a lot of time, so if you identify with that description, you know it’s not possible for you to take action on all your ideas.

So … what do you do?

Today I’ll show you a tool I’ve used and recommended for years. I first wrote about it in the book SIDE HUSTLE—so if you’ve read it thereof if you’ve heard me talk about this before, I’ll use all new examples here to keep it fresh.

Here’s how it works…

When you’re starting out, you might struggle with ideas. In the long-term, though, being able to identify potential ideas is rarely a problem. Side hustle success comes from making ideas happen!

In fact, you’ll often have more ideas than you can handle. What do you do if you have two or three different ideas? Should you try them all at once? Should you only pick one?

First, here is some general, all-purpose advice in two parts.

  • 1) Get clear on your goals! Make money soon, build an asset, explore a different creative skill? Your idea should connect directly to your goals. For example: long-term mission is different from pay off debt.
  • 2) Remove the pressure from the decision. You’re not selecting an idea forever. You’re selecting the right idea for you now.

Next, at the workshops I taught a while back, we used a tool called the Side Hustle Selector. I’m going to show you a stripped-down version here.

When you have more than one idea, consider three variables:

  • Feasibility – How confident are you in the ability to begin turning the idea into action in a short period of time?
  • Profitability – How confident are you in the potential to make money from this idea, also in a short period of time?
  • Motivation – How excited are you about this idea?

If you have two or more ideas, see how they rank in each of these categories.

  • It’s okay to estimate if you’re not sure, this is all about making a back-of-the-napkin evaluation.
  • Looking at the data can often help you decide between competing ideas, or at the very least, reduce the number of options you’re considering.
  • If they’re truly equal, well, just pick one!

In the episode, I’ll give you an example of how this works in the real world, and then an assignment for you to apply this to your own ideas.


CLASSROOM #3: Different Categories of Side Hustles


Last week we talked where moneymaking ideas come from. I gave you a number of examples, including some suggested by listeners (my favorite: call your dog on Skype service). We looked at four ways to find high-potential ideas:

  • Observation: paying attention to the world around you, perhaps noticing something that could be improved
  • Problem solving: making lists of problems and brainstorming solutions in the form of products and services
  • Asking questions: looking for the reasons, stated or subtle, for why people spend money (and deciphering what else they might buy)
  • Experimentation: just trying out whatever comes to mind

Most business ideas fall into two broad categories: providing a service or selling a product, one way or another. A product is something you sell, a service is something you provide. Products can be digital and services can be virtual, but most of what we’ll look at this year can fit into one of those two big buckets.


CLASSROOM #2: Four Ways to Identify Moneymaking Ideas


Let’s talk about finding ideas. We’re going to go on an idea treasure hunt. Get your idea butterfly net … this is like Pokemon Go but for ideas.

If you’re following in real-time, that’s great because each CLASSROOM episode will have an assignment. I want you to work hard, but I don’t want you to work too quickly. Everything we do will build as we go along. And if you’re listening later, you can just go back-to-back.

Let’s start with this important question: Where do moneymaking ideas come from?

Consider a few of the stories we featured just last month (there are hundreds of other examples; I’m just highlighting a very small selection):

  • Ep. 1066: Electrical Engineer Rides Demand to Dog Collar Empire
  • Ep. 1070: Friends Turn Gift Boxes into Prosperous Project
  • Ep. 1080: Musicians Tune Up Classical Concerts For Families
  • Ep. 1087: Software Engineer Scavenges For Profits

More often than not, these projects come about because someone noticed something and then decided to explore it.


CLASSROOM #1: Goals, Agenda, and Your First Assignment


Breaking news: everything is new!

For the first time in three years—and I do mean exactly three years—we are reinventing the format of Side Hustle School. I’ve been working on this for several months and I’m excited to kick things off.

Longtime listeners, here’s what’s not changing —

1. The daily format. It’s still every day (7x/week) and still short, less than 10 minutes per episode on average. I know you’re busy!

2. The message. We’re still all about helping people with jobs embrace the world of moneymaking side projects. Maybe you’ve never identified as an entrepreneur, but you understand the importance of having more than one source of income.

What’s changing is that 2020 is The Year of interaction.

In real-time this year, we’re going to do a year of Questions and Answers and instruction where I guide many of our listeners—perhaps even you—as they go from idea to income. It’s essentially live coaching—for free—and you can listen in and learn as we go.


Want to participate? It’s easy: write us at or simply ask your question here.