On episode 10 of Friday Lives, host Anya Razina speaks with bestselling author Chris Guillebeau. After traveling to every country in the world and sharing his perspective on traveling and life in his blog The Art of Non-Conformity, Chris wrote some bestselling books about learning to follow your own path and entrepreneurship — The $100 Startup, The Money Tree, Side Hustle: From Idea to Income in 27 Days, and many more. In addition to being an author, Chris gives advice about starting a side hustle on his podcast Side Hustle School.

He and Anya discuss entrepreneurship, motivating yourself, and how live streaming can support your side hustle. Chris also shares a bit from his travel experiences.

🤔 How Chris got started

Chris’s journey started with travel. He loved experiencing new cultures, seeing new places, and meeting new people. He was an aid worker in West Africa when he decided he wanted to see 100 countries, then every country in the world. He started The Art of Non-Conformity, a blog to document his quest and his unique take on traveling and how to see the world. In addition to travel, Chris loves entrepreneurship, and he’s worked for himself almost his whole life.

His blog’s success eventually led to his writing a series of books, producing a podcast, and speaking at events worldwide. From all of his success, Chris is most grateful for his opportunity to connect with new people all over the world.

✍️ How to start a writing career

Chris has had a successful writing career as a New York Times Bestselling Author, but how did it start? He had a desire to share his ideas and perspectives about the world. He’d been living as a digital nomad and wanted to spread his message about his lifestyle. So he started a blog.

Chris encourages anyone who has something to share or an idea to express to start writing. If you invest as much time, energy, and patience in your blog or your writing as Chris did, you’ll find like-minded people and eventually become part of a community that supports you.

🤑 Money doesn’t grow on trees?

Chris admits that success isn’t automatic and that money may not grow on trees — at least not at the start. His approach to success in his newest book, The Money Tree, is to plant seeds that will grow into something profitable. He emphasizes that everyone is an expert in something, and success only means recognizing the skills you have and finding a way to package them into a product or service for others.

Most people out there actually know something already that's valuable and interesting to other people. So it's just a matter of finding a way to take that thing and transform it or adapt it into some kind of product or service people can pay for.

🖤 Finding the intersection of doing what you love and providing value to others

Although combining your passion with being productive sounds simple, it’s not so easy to apply in practice. Finding that perfect balance is a process, and each step in the process requires effort. Chris thinks people struggle with turning their passions into productivity for two reasons:

  1. People tend to skip steps. They don’t focus enough on finding their skills, and it leads to more effort later.
  2. Self-doubt creeps in easily for many people. Imposter syndrome is real when you’re just starting something, or you compare yourself to others and doubt you can ever do the same.

Chris emphasizes moving forward, one step at a time, even when you don’t know where the journey ends.

We're all making mistakes. Everybody's on a journey, but the real power is in taking those steps forward.

💸 Should entrepreneurs start slow or invest?

Entrepreneurs and startups always get the advice that they should invest their money when starting out, or “spend money to make money.” In his book, $100 Startup, Chris notes that this isn’t the only approach to starting your own business. He didn’t think there was enough advice out there focusing on starting slowly or investing with much smaller sums of money.

His advice is to do what’s best for your business. If you need to invest heavily for the type of business you want to run, then do it. But many people don’t want a Silicon Valley startup business plan and would rather pursue stability and self-reliance. If freedom to run your own business is what you want, you have to ask yourself what you can do to make money first, without costing a lot. Also, pitching to investors is deferring the success or failure of your business to someone else.

If the objective is freedom, what is the best way for it to get to that? And I think the best way is to not spend money, but to choose, to find a project that you can start right now, where you are, without spending money.

👉 What are the key features of a successful side hustle?

Chris highlights five factors that make for a good side hustle:

  1. Not a hobby. A side hustle is not just an activity you do for fun; it also generates income.
  2. Not part of your job. A side hustle is a separate activity from your day job or full-time job.
  3. Starts quickly. If you’re like most people starting side hustles, you don’t have a lot of free time. Your time is valuable, so a good side hustle will be something you can start up quickly.
  4. Simple. You should be able to explain your side hustle in one sentence — no backstory, no context, just one simple idea.
  5. People can pay for it. A big problem with starting side hustles is figuring out how to monetize. Determine what your deliverable is — what will people pay for when they buy from you?

📹 Incorporating live streaming into your side hustle

For those starting a side hustle, live streaming can be a great way to build a community and generate leads, or it can be the product itself. Live streaming is a great way to connect with your audience; they can see and hear you in real time, rather than just reading words you wrote and published on a blog. They can also ask you questions and get immediate responses.

To use live streaming as a product for your side hustle, you can stream a course or tutorial and sell subscriptions to it.

🙌 How to commit to daily content creation

When Chris started the Side Hustle School podcast in 2017, he committed to making a new episode every day, for one year. The podcast continued well past one year, and he’s almost to 1500 episodes. Many people would find a daily commitment to creating content — whether it’s a blog post, podcast, video, or live stream — a daunting challenge.

But Chris has a secret for accomplishing a new podcast episode every day. For him, it’s easier to do something on a daily basis than on a weekly basis. When something is weekly, you have to set aside time to work on it, and it doesn’t fall into a good rhythm. When something is daily, it’s much easier to incorporate into your schedule and find time for. Creating content becomes an essential part of your day, like eating lunch.

[Podcasting every day] is good for the audience as well for the community. It shows them that this thing is there every day and they can depend on it.

🎙 Staying positive on your podcast or live stream

What do you do if you've had a bad day and you have to host your daily podcast or live stream? Chris says he doesn’t transfer the negativity to his listeners and instead focuses on the cool story or person he’s showcasing on his episode. He thinks about how listeners can learn from his episode rather than feeling bad about having a bad day. He also drinks lots of coffee.

🔥 Success stories from Side Hustle School

Chris highlighted a few of his favorite side hustle stories as examples of how to turn your niche or hobby into a profitable activity.

  • One man’s side hustle was creating archery tool kits. He loved archery and developed a kit for bow strings that hadn’t been done before. He now earns a sizable income from his side hustle while still holding his full-time day job.
  • A high school student did bug bounties and was able to earn around $100,000 over the course of a few years. Bug bounties are when companies pay ethical hackers to find bugs or weaknesses in their systems or websites.
  • Chris featured a gaming live streamer as well, to delve into the business side of live streaming games and how that kind of side hustle can be profitable.
  • One person started a side hustle drop shipping live crickets to reptile pet owners. He wasn’t passionate about reptiles or a pet owner himself, but he knew there was a need for pet owners to get crickets to feed their reptiles. Because he was drop shipping, he never had to actually handle the live crickets himself.

👀 How to price side hustle services

How much you charge depends on the industry or niche you’re operating in, but Chris does offer a few general side hustle pricing rules to stick to:

  • Figure out your hourly rate at your day job and seek to earn at least that much for the time you spend on your side hustle. Ideally, you would earn a higher hourly rate for your side hustle than your full-time job, as you’re putting your spare time into it.
  • If you choose a side hustle that other people are already doing, such as coaching or consulting, look at their rates and try to set yours accordingly.
  • Most service providers tend to start out undercharging. If you’re able to raise your rates and your customers or clients still buy from you, it means your rates were too low to begin with.
Your goal is to always charge the maximum that you can, but still have people accept.

🔗 Idea vs. execution

Is there such a thing as a bad idea? Or can you pull anything off as long as you execute it properly? Coming up with good ideas is valuable, but implementing them is more valuable. You shouldn’t worry about somebody trying to steal your idea because anyone looking to steal an idea probably has no clue on implementing it.

It is possible to come up with a bad idea, and the way you can tell is by examining feasibility. If you have several ideas, think about which one you can implement the most quickly, with the most profit potential. The ideas that don’t allow you to do that are probably bad ones.

🤓 Setting yourself apart in a crowded field

When you want to get into a niche or industry that already has a lot of people working in it, such as graphic design, you need a way to make yourself stand out. Instead of being a general graphic designer, be a graphic designer exclusively for live streamers or for the pet industry. If you want to earn your desired rates in a field where people charge anywhere from $20 an hour to $200 an hour, you have to pinpoint your specific service offering.

The number-one thing you can do is to say, ‘I'm not just a general designer. I am a designer that does this specific thing for these kind of people.

🤷 Reasons that stop people from starting a side hustle

Chris hears a lot of reasons why people are unmotivated to live stream. He shares three common ones:

  1. Not enough time. Look at choosing to invest your time as a way to improve yourself. Aim to make the use of your time as efficient as possible.
  2. Not enough money. It’s possible to get started without much money at all. Chris’s work focuses on helping people see opportunities that don’t require a huge monetary investment.
  3. You tried before and it didn’t work. Everybody tries things that don’t work. The goal is to not let it set you back and focus on something new or different instead.

No matter how many reasons hold you back, always look for one reason that motivates you to start your side hustle.

Maybe it seems scary, but it's actually going to be really good for you, when you actually move forward with it.

⏰ How do you find time to do a side hustle?

Finding the time to pursue your side hustle is a personal challenge — not everyone will schedule their time the same way. Maybe it takes giving up something else, like watching your favorite 30-minute TV series, so that you can spend time on your side hustle. When you only have a little bit of time set aside, it’s a great way to motivate you to be more efficient. For live streamers, streaming to multiple channels at once with Restream is a great way to make better use of your time as well.

Pick out the number-one thing you need to do during your 30 minutes or one hour a day that you focus on your side hustle, and get it done.

🔴 Switching from a podcast to a live show

Like many people, the COVID-19 pandemic in 2020 inspired Chris to start live streaming. He’d planned a book tour for the release of The Money Tree in April, but obviously he was unable to do it. Not being able to go into communities and meet with people was disappointing for Chris because connecting with others is his favorite part of his work.

He decided he needed to change and find a way to connect with people again, so he started live streaming every day, for 30 days. After that, he streamed once a week.

[Live streaming] was definitely a learning curve for me. But I'm really glad that I did it. I think it establishes a close relationship with people.

😎 Do entrepreneurs and side hustlers benefit from live streaming?

According to Chris, anybody can benefit from live streaming if they have a message to share. No matter how niche your business or side hustle is, you can still find a community for it. If you want to add live streaming to your strategy, just ensure that you’re providing value and can support doing live streaming in addition to your other business activities.

🛩 Chris’s traveling story

Chris has always loved traveling, and was able to experience living in different countries from a young age. At some point, he realized he’d been to 30 countries already and decided to set a goal for himself. He’d visit 100 countries to be able to reach that milestone and get to see new places. Once he got to 100, he decided to go for all 193.

For Chris, his journeys were never about notoriety. He started his blog because he wanted to share his experiences, but he wasn’t trying to break records or attract fame. He just wanted to achieve his personal goal. He’s used this mindset throughout his life and emphasizes personal goal setting and taking things one step at a time in his books and podcast.

I wasn't trying to be like the fastest person or the youngest person or anything like that. It was more that I'm curious, I like to work towards specific goals and milestones, and I like to travel. So why don't I put these things together?

💫 Let’s wrap up

As a bestselling author and entrepreneurship coach, Chris Guillebeau had some great insights to share on this episode of Friday Lives, including tips for starting a side hustle, how to incorporate live streaming as an entrepreneur or side hustler, and how to stay positive when you go live. The biggest takeaway from his conversation with Anya is how to turn your talents and passions into resources that work for you. Hopefully Chris’s advice was the motivation you needed to get going on your side hustle!