Classroom: New for 2020!


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.

Fill out my online form.

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

CLASSROOM #11: Finding Time to Work on Your Hustle


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. We looked at the three elements of every compelling offer: a promise, a pitch, and a price, and then we examined the difference between what people say they want and what they really want.

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


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. We looked at the three elements of every compelling offer: a promise, a pitch, and a price, and last week we examined the difference between what people say they want and what they really want.

Essentially we’re going from thinking about ideas to designing real offers.

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.