Policy Researcher Offers Private Tours of Nation’s Capital

What It’s About

Tour guide “trip hacks” his way to $1,500/month using YouTube.

[podcast_details]

Words of Wisdom

With the idea hatched, guidebook firmly in hand and a custom t-shirt printed, Rob was ready for business. To get customers he first thought to use TripAdvisor. Go where the tourists go right? But it’s not so easily done! Competition in DC for tour guides is fierce. There are currently over 150 companies listed in the tours section of TripAdvisor. With 22 million tourists visiting every year, it’s easy to understand why.

Instead of giving up or banging his head against the wall, Rob got creative—and it seems like it was the much better approach.

Fun Fact

While Washington DC is home to some of the world’s most famous monuments and memorials, there are also a multitude of fun facts about our capital and presidents that might surprise you!

The city itself uses letters instead of numbers to name their streets, but because DC was planned prior to the letter J joining our alphabet, there is no “J street” in the city. And although most of our recent Commanders in Chief have opted for a family dog, some of our past presidents have made more unconventional choices. Did you know that both Herbert Hoover and John Quincy Adams (allegedly) had pet alligators while they were in the White House?

Notes from Chris

Episode 508

There are two things that Rob Pitingolo loves: hanging out with people… and his hometown, Washington DC. So it’s of little surprise that, outside of his day job, Rob spent four years as a part-time tour guide. He got to meet interesting people and show them around the nation’s capital.

A big chunk of the DC population works in government, and Rob is no different. His full-time job is in public policy research. But in addition to the population of government employees, there are also a lot of tourists. The latter make up the lion’s share of the population during summer and spring.

Tourists give the city a constant hum of excitement. Sometimes it made Rob feel like he was on vacation himself. That’s why he spent a lot of his free time working as a tour guide. Not in his own side hustle per se, but for one of the biggest tour operators in the city.

Being a true “people person,” Rob most enjoyed the small, intimate private tours with only a few people. But, the problem with working for a large operation is that there are very few opportunities to give those tours. The real money for those companies is in volume. The chance to lead a group of only a few people rarely comes up.

Instead of begging the company he worked for to take on the limited amount of private tours on offer, Rob decided to take matters into his own hands! He took a step that America’s founding fathers would be proud of and inched himself closer to the American dream. How? He decided to start his own side hustle, and he called it Trip Hacks DC!

He’d offer private tours that he knew tourists would love.

To get customers he first thought to use TripAdvisor. Go where the tourists go right? But it’s not so easily done! Competition in DC for tour guides is fierce.

You can’t just add your company to the site and hope for the best. TripAdvisor prioritizes reviews above everything else—so if you’re new to the game, you’re at a real disadvantage. In Rob’s case, some of the top companies in DC had 100’s of reviews already.

This revelation led him to a hard truth. The difficult part of starting his tour company will be getting people to know he even exists. To paraphrase an old proverb. If a guide talks in the city and no one is around to hear it, is he really a guide at all?

Rob refused to head down the same path as everyone else and resort to fighting over TripAdvisor crumbs. He knew he had to think outside the box. So, he decided to try YouTube as a way to reach potential customers.

It turned out to be a great insight!

Using his own initiative, Rob is guiding himself to the bank, earning around $1,500 per month on average. Not bad for a little known public policy researcher from DC working on the side and doing it in his own way.


MENTIONED IN THIS EPISODE:

  • Trip Hacks DC: Did you know that among the many gargoyles adorning the National Cathedral, there’s a sculpture of Darth Vader’s head? I bet Rob knew that one! Learn more about him on his website
  • TripAdvisor & YouTube: The two platforms that Rob used to get Trip Hacks DC out to the masses

SEE ALSO:

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Resources

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

GET YOUR FIRST 1,000 EMAIL SUBSCRIBERS

Social media is nice, but building an email list is still the single best way to get customers and clients for your hustle. It's not hard to get started—sign up for a 30-day trial and join the list-building challenge! You’ll be up and running in no time. Learn More

Quote of the Day
"The best part of this side hustle is getting to meet everyone who finds my YouTube videos and decides to book a tour with me. It’s one thing for people to leave a comment and say the videos are helpful, it’s even more rewarding when they spend their hard-earned cash on a tour to prove it."
—Rob Pitingolo #SideHustleSchool

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Side Hustle School is brought to you by CardsForTravel.com. Use travel hacking to see the world!

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It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.
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There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!


To infinity and beyond,

Chris Guillebeau

Florida Man Leads Scooter Tours After Watching Macklemore Video

What It’s About

Texas man rolls his way to a successful tourism based side hustle in Florida.

[podcast_details]

Words of Wisdom

If anything can be said about Jordan, it’s that he’s incredibly resourceful. He used his knowledge and experience in web development as leverage to get both the Kickbikes he would use for his tours and starting spots that he needed. Everyone has some skill or experience that they can offer, and sometimes that can be something that helps you cut costs when you’re building your side hustle. What kind of skill or experience can you offer?

Fun Fact

20 years ago, Hannu Vierikko, a Finnish doctor and adventure enthusiast, invented the transformative Kicksled, an innovative new dogsled that forever changed the competitive mushing world. Looking for a way to train with his dogs in the summer months, the Kickbike was invented.

Notes from Chris

Episode 305

Jordan Crowder is an independent side hustler who wears tank tops and a pair of boardshorts to work most days, but back in 2013, he was working a typical job as a marketing and art director for a major corporation in Dallas, Texas. Wanting to break free from his golden handcuffs, Jordan worked his way into a full-time remote position with the goal of eventually moving his wife and two young daughters to their dream destination—a little stretch of paradise in the Florida Panhandle called 30A (fun fact: where The Truman Show with Jim Carrey was filmed).

Not knowing a soul on 30A, and having to support his family, he decided to not tell his employer that he was moving (in his words “Hey, I was remote, so what’s the difference?!”). Of course, he still did his job well, but in the back of his mind, he knew the clock was gradually counting down until a more permanent change would be required.

So, being the resourceful person that he is, he looked around his newfound paradise for new opportunities.

One thing he noticed during his research was that—like many beach towns—bikes, skateboards, and walking were the preferred methods of transportation on the 30A. Not one to just stick with the status quo, Jordan started looking into other unique methods and products that he could bring to this newfound adventurous pedestrian market.

Not long after that, Jordan had what he calls his “AHA!” moment…

You might be familiar with the music video for Macklemore’s “Thrift Shop,” in which the artist embracing the values of frugality and bargain-basement shopping, undertakes an anthropological exploration to a number of secondhand stores in search of formerly unwanted items. In that magnum opus, Macklemore famously promised to take your grandpa’s style…

In addition to all of that, in parts of the video the artist Macklemore is seen riding on an old school scooter, Jordan began to wax nostalgic about his early days spent meandering about on his old mongoose scooter. And when he went to find an adult version, he stumbled on KickbikeUS. Jordan was blown away and thought, “THIS IS AMAZING!!!!! It’s like some incredible Scandinavian team of designers and engineers were reading my diary!”

The 30A road ran along an absolutely amazing coastline dotted with a dozen vibrant, little beach communities that each boasted their own unique vibe and flavor, and Jordan thought that Kickbikes would provide the perfect vehicle for a fit and fun tour that would enable people to get ‘off 30A’ and see another side of this incredible place he called home. Thus, Jordan’s Kickbike tour side hustle was born!

He ended up leaving the corporation in Dallas in order to freelance as a web developer and marketing expert full time, and his Kickbike tours and online sales commissions are bringing in around $1,700-2,700 a month!

All in all, Jordan says that starting and running his Kickbike tours has been a fun ride, and he’s thinking about what comes next. Maybe he’ll roll his way into markets where the adult scooter trend hasn’t yet kicked its way down the road.

 

MENTIONED IN THIS EPISODE:

SEE ALSO:

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Resources

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! ✈️ Learn More

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

Quote of the Day
"Sometimes, to get the job of your dreams, you have to dream up the job, hire yourself, and then quickly prove you belong there."
—Jordan Crowder #SideHustleSchool

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Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.
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To infinity and beyond,

Chris Guillebeau

Busy Marketing Professional Fills Niche with Biking Wine Tours

What It’s About

A Canadian wine tour on bikes!

[podcast_details]

Words of Wisdom

Erin took action on her idea because she believed that if she didn’t launch something, someone else would.

As she put it, “If your idea keeps you up at night because you know you’ll be annoyed if someone else does it before you, it’s a good sign that you should pursue it.”

Fun Fact

Erin’s favorite tour so far was a private tour with her friends and family. While she was expecting a fun weekend with her friends, her boyfriend had other plans in mind and proposed at the last stop. Needless to say, both the bubbly and the excitement were plentiful.

Notes from Chris

Episode 208

Erin Bury didn’t think she had time for a side hustle. As Managing Director and a partner in a creative communications agency, she had a lot on her plate. But there was also an idea that wouldn’t go away.

Erin grew up visiting Prince Edward County, an up and coming wine region about two hours outside of Toronto. As she got older and of drinking age, her dad moved there and she would visit every summer with friends. They all loved touring the wineries but noticed that while there were limo tours available, unlike other wine regions there were no bicycle tours available. Erin knew this was a popular activity offered elsewhere.

She also believed that if she didn’t launch something, someone else would. As she put it, “If your idea keeps you up at night because you know you’ll be annoyed if someone else does it before you, it’s a good sign that you should pursue it.”

After a lot of planning on weekends and evenings, The County Wine Tours launched in May of this year. Their website is built on WordPress so they can easily maintain it, with online scheduling and payments processed by Checkfront. The tours are priced at $95 per person and so far they’ve been completely booked up on weekend days with anywhere from 2 to 10 people on a tour.

With anywhere from 5 to 10 inquiries coming in daily, Erin and her co-founders are excited that their great idea has gotten so much traction, so quickly. Their biggest problem at this point is managing demand on popular days. With the framework in place for public tours, they’ve also created private tours so people can book for a birthday party or bachelorette party, as well as corporate tours that companies can use as part of a retreat.

While it’s clear that there’s lots of room for expansion, they plan to ride out this season with their current bikes and then decide how many to add for next season.


MENTIONED IN THIS EPISODE:

  • The County Wine Tours: Learn more about Erin’s niche bike tour side hustle on her website!
  • Giant Bicycles: The bicycle manufacturer that Erin worked with to select a fun cruiser bike with custom accessories for her bike tours
  • Keyword Planner: This tool helps you reach the right customers with the right keywords and helps you to better build your SEO and ad campaigns
  • TripAdvisor: Setting up their TripAdvisor profile helped The County Wine Tours capture those “word of mouth” recommendations online
  • Checkfront: The online booking system and reservation software that Erin used

SEE ALSO:

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Resources

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! ✈️ Learn More

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

Quote of the Day
"It’s impossible to do it all yourself. I work on the business during the evenings and on Sundays, and I’ve outsourced functions like customer service, marketing coordination and accounting so I can focus on the high-level stuff."
—Erin Bury #SideHustleSchool

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Today’s episode of Side Hustle School is brought to you by ShipStation, the #1 choice of online sellers. 📦

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Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.
Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!


To infinity and beyond,

Chris Guillebeau

Food and Travel Writer Creates Food Tours in Marrakech, Earns $60k Annually

What It’s About

A lucrative food tour side hustle in Morocco run by an American expat and her local husband.

[podcast_details]

Words of Wisdom

Since her husband, Youssef, grew up in Marrakech, he already knew a lot of people and a lot of good places to eat. They also ate out fairly often, so they had plenty of non-touristy stops to choose from. The first step was coming up with a tour route that made sense. They wanted the tour to be a walking progressive meal, so they’d go to one place for appetizers, another for salad, another for the main course and a final stop for dessert. Making sure the order of the food and the route of the walking tour made sense was the most time consuming part initially.

If you’re struggling to come up with ideas, start with what you know! You’d be surprised what you can create utilizing skills or information you already have.

Fun Fact

Amanda and her husband Youssef got the inspiration for their food tours from watching tourists go into mediocre restaurants and then recalling their family and friends complain about the bad food in Morocco. They knew where the good food was and they could take people there. $50 in start up costs plus three years has resulted in a steady income stream and the financial freedom for Youssef to quit his job.

Notes from Chris

Episode 201

In January 2014, Amanda Ponzio-Mouttaki was sitting with her husband, Youssef, at a cafe on the main square in Marrakech, Morrocco watching tourists go into restaurants that they knew weren’t great. As an American expat married to a local, Amanda would give advice when she could and specific recommendations on her website, but she suddenly put these pieces together and realized she was perfectly situated to offer English speaking tours that would show tourists where the good food was hidden in Marrakech. And as a freelancer who writes about food and travels for food, Amanda had the skill set to pull it off.

With minimal marketing in place, Amanda started with really low expectations. She wanted to make $200 a month to cover schooling costs for her two kids and to give their budget a little more breathing room in general. However, they exceeded Amanda’s financial expectations in the first couple months, and within six months of launching they were bringing in $2,000 per month.

Amanda credits a lot of their success to finding something missing in the marketplace and then going for it. As she explains, “We were the right people at the right time to meet that need. We also made the decision to just focus on food and only do tours in English. We couldn’t be everything to everyone and so we’ve made a decision not to do tours in other languages. Specializing has been very powerful for us!”


MENTIONED IN THIS EPISODE:

  • Marrakech Food Tours: Learn more about Morocco and Amanda’s foodie tour service on her website!
  • MarocMama: Amanda’s Moroccan resource blog
  • WordPress: Amanda used WordPress for her website, and here you can learn how to install your own WordPress site in 5 minutes!
  • Keyword Planner: This tool helps you reach the right customers with the right keywords and helps you to better build your SEO and ad campaigns

SEE ALSO:

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Resources

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! ✈️ Learn More

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

Quote of the Day
"The key for us was finding something missing in the marketplace and being the right people at the right time to meet that need. We also made the decision we would just focus on food and we would only do tours in English. We couldn’t be everything to everyone and so we’ve made a decision not to do tours in other languages. Specializing, has been very powerful for us!"
—Amanda Ponzio-Mouttaki #SideHustleSchool

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Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Blue Apron. 👩🍳

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Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.


Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!


To infinity and beyond,

Chris Guillebeau

London Chocolate Tours Lead to Sweet Success

What It’s About

A niche chocolate, tourism-based side hustle in the United Kingdom!

[podcast_details]

Words of Wisdom

When Jennifer was considering the kind of side hustles she could start, she created a very simple list, and I encourage you to do the same! This exercise involves writing down all the ways you spend your time when you have a choice about it. This could include:

  • Hobbies, art or music, sports, video games, reading (novels, nonfiction, teenage vampire romance, etc.), travel, etc.

Basically, if your day was open, what would you do?

Fun Fact

Sometimes people don’t really know what they want. Jennifer used information from a customer survey to launch a Chocolate & Coffee Tour option that never really took off. After that she decided to use her own intuition and launched an Ice Cream Tour—it’s now her second best-selling tour.

Notes from Chris

Episode 194

Jennifer Earle runs chocolate tours with her company, Chocolate Ecstacy Tours. Sounds like a dream job, right? It definitely is now, but it took her awhile to get there. To really understand her story, we have to jump back to 2005 when Jennifer was temping part-time to make ends meet. She knew she wanted to do something on her own, but she wasn’t sure what kind of business she wanted.

So she started by writing down everything she loved and everything she was good at. That list included chocolate, meeting people, talking, eating and London. From there, she brainstormed potential ideas, and the standout idea was chocolate tours. She optimistically figured that everyone loves chocolate, so it should be any easy sell. And just as important, it was the right level of commitment for her—different enough that it was outside her comfort zone, but small enough that she wouldn’t have to take out a loan or spend too much money to get started.

After about a year of trying to make her chocolate tours into a full-time income, she decided she needed a “real job.” Over the next few years, she worked in various roles at three big companies. Jennifer got those jobs because she had her own food side hustle, which was a great added benefit, but the whole time she really just wanted to be working for herself.

Business slowly increased over the years, all the while Jennifer was working full-time and managing this on the side. In 2012 she brought in £16k ($20,581.04 USD) in revenue, and since £24k ($30,871.56 USD) was the average salary at the time, she felt pretty good about that. So good that at the end of the year she decided to quit her job and make the jump to full-time entrepreneur. Over the next two years revenue doubled each year and in 2016 she brought in £82k ($105,477.83 USD).


MENTIONED IN THIS EPISODE:

  • Chocolate Ecstacy Tours: Indulge in your chocolate obsession with the assistance of Jennifer’s website
  • Weekly Recap: Live Crickets, Tarot, and Reinventing the Bra: In our seventh weekly recap, we’ll highlight the lessons learned in this week of Side Hustle School. I’ve also included a quick exercise to help you generate ideas based on your interests
  • Dreamweaver: The program that Jennifer used
  • Keyword Planner: This tool helps you reach the right customers with the right keywords and helps you to better build your SEO and ad campaigns
  • TripAdvisor & Yelp Some of the companies that drove business to Chocolate Ecstacy Tours

SEE ALSO:

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Resources

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! ✈️ Learn More

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

Quote of the Day
"If you aren’t sure what to do, write a list like I did, and include what you love to do, what you’re good at, etc. then brainstorm ideas from there and evaluate potential businesses based on the type of lifestyle you have and want."
—Jennifer Earle #SideHustleSchool

Sponsors & Gratitude

Get a FREE Audiobook from Audible!

Audible is offering SHS listeners a free copy of the Born For This audiobook with a 30-day trial membership. 📚

Just go to aonc.co/bftaudible and browse the unmatched selection of audio programs and start listening.
Get it Here

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.
Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!


To infinity and beyond,

Chris Guillebeau

Pilot’s Side Hustle Takes Flight With Aerial Tours

What It’s About

A niche side hustle flying tourists in small, passenger planes so that they can have a unique view of the Pacific Northwest.

[podcast_details]

Words of Wisdom

A lot of Corey’s success comes down to his unique way of charging for tours. Instead of charging high premiums per person, Envi Adventures flights are priced per flight. Depending on the tour they choose, customers can expect to pay $99, $199, $265, or $349. A variety of price points opens the door to more people and in the end is more cost effective.

Fun Fact

Did you know 50% of travel companies have said that direct bookings have been generated from social media and 52% of travelers use social media to plan a trip? That means if you’re not on social, you could be missing out on a lot of customers!

Notes from Chris

Episode 193

If you live in an area visited by tourists, there are probably a lot of different options to make money by showing them around. From a young age, Cory Rust has spent large chunks of his time exploring the nature and wilderness of his hometown in Oregon. He’s seen the Gorge, walked beside the Columbia River, hiked through the forests and even started a small clothing brand based on local designs.

However, Corey wanted to take it a step further. He wanted to show people who were visiting the area exactly where they were and what they were experiencing. He knew tourists were already flocking to the local waterfalls, but couldn’t help feeling this was only a small percentage of what the place had to offer.

So, he set about creating Envi Adventures, with the goal of giving people what he called the 360-degree experience.

 

MENTIONED IN THIS EPISODE:

SEE ALSO:

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Resources

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! ✈️ Learn More

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

Quote of the Day
"Be patient and set your priorities. Take a piece of paper and write your idea on the top. Then, list out all of the things you think you need to do in order of importance. Leave space in between because you’ll add things. After that, just start tackling them one-by-one."
—Corey Rust #SideHustleSchool

Sponsors & Gratitude

Get a FREE Audiobook from Audible!

Audible is offering SHS listeners a free copy of the Born For This audiobook with a 30-day trial membership. 📚

Just go to aonc.co/bftaudible and browse the unmatched selection of audio programs and start listening.
Get it Here

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.
Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!


To infinity and beyond,

Chris Guillebeau

Harvard Med School Program Manager Gets Paid to Travel to Italy

What It’s About

A profitable side hustle that celebrates Italian culture and helps a Boston woman revisit her roots.

[podcast_details]

Words of Wisdom

Francesca’s “Aha!” moment came when she looked back at all of the free advice she’d given out over the years. She’d shared her family’s authentic Italian recipes with her friends, helped them book entire holidays and taught countless people about Italian culture. So, she asked herself the all-important side hustle question, “Can I charge for this?”

A side hustle should be something that you look forward to—not just tolerate. And some of the best side hustles we’ve featured on the show start out as something they do for fun. Is there something that you love doing that would make for a good side hustle?

Fun Fact

As a native Italian in Boston, Francesca started her side hustle as a way to travel back to Italy more frequently. This permits her to organize a few week-long tours, make connections by building private trips and helps with her constant craving for Italy! She is also a great cook, so she teaches Italian cooking at the adult education centers as well as private classes in her own home.

If you think limiting your travel business to one country could be a little too niche, you’d be wrong. Around 48.6 million tourists visit Italy every year. That’s 10 million more people than live in California!

Notes from Chris

Episode 171

Francesca Montillo’s side hustle was 20 years in the making. Ever since she left high school, she dreamt of starting her own travel business and sharing a small pizza-slice of her native Italy with the world. But instead of following her dream, Francesca opted for what she thought was the safe option.

After 20 years of waiting for the right time, she decided to finally go ahead and start her business anyway.

Putting a basic website online that she called The Lazy Italian, she wrote about her experiences, holidays she’d planned and recipes she loved to cook. She made sure to mention she was the real Italian deal, too.

Right now Francesca is making an average of $500 a month through her side hustle, although this number can get a lot higher when she’s got a big tour to work with.

Francesca’s ultimate goal now is to turn this side hustle into her full-time work in the next one to two years, and she plans to start promoting her tours to bigger groups. She also wants to stop running stateside cooking classes (no matter how fun they are) and instead turn her attention to writing a Lazy Italian Cookbook.


MENTIONED IN THIS EPISODE:

  • Lazy Italian Culinary Adventures:Book your own all-inclusive Italian excursion on Francesca’s website!
  • ServSafe:The online certification course Francesca took so that she could teach her cooking classes

SEE ALSO:

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Resources

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! ✈️ Learn More

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

Quote of the Day
"At first when I saw my competition it was upsetting, but then I realized that I was comparing my ‘Chapter 1’ to someone else’s ‘Chapter 15 or 20’—they had been in the business longer and yes, were doing better, but I was comparing apples to oranges."
—Francesa Montillo #SideHustleSchool

Sponsors & Gratitude

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There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!


To infinity and beyond,

Chris Guillebeau

Urban Hiker Climbs to Steep Success in San Francisco

What It’s About

An urban hiking tour company with low startup costs.

[podcast_details]

Words of Wisdom

The best part about this side hustle model is that pretty much anyone can start something similar. Research tourism in your area, and ask yourself if there is enough tourism in your town to start a tour. If there is, what kind of tour do you want to run? Are there already competitors in your area?

If it’s something that you think is feasible to do, plan out a couple tours and test them out with people you know!

Fun Fact

Most of the challenges Alexandra has had to face are related to her having to cancel tours due to rainy weather. Normally, this only happens a few times a year, but last winter the San Francisco area experienced the wettest winter ever recorded since they started tracking rainfall in 1895! That definitely slowed things down for Urban Hiker San Francisco before it picked up again this spring.

Notes from Chris

Episode 158

San Francisco-based Alexandra Kenin has a flexible job as a project manager and editor for a fully-remote company. It’s a dream job in the sense that she’s able to set her own schedule and go back and forth from focusing on those job responsibilities to building something for herself.

The company is in the tech industry, but Alexandra’s side hustle is completely different: it’s all about getting outdoors and showing city-dwellers and tourists a lesser-visited side of SF—the part of the city that includes scenic hills and hiking trails.

Depending on the season, Urban Hiker San Francisco: makes between $2,500 and $8000 per month, peaking in July. Overall, gross income is about $50,000 per year. Corporate groups are the biggest source of income. She typically earns $1000+ for each 2-3 hour event. Alexandra now has 4-5 contractors working for her, depending on the season.

More than 3,000 people have hiked with Alexandra and her guides, including a lot of foreign visitors. Sometimes it’s their very first day in the United States, so she loves being able to show off her city and provide a good introduction to the USA.

 

MENTIONED IN THIS EPISODE:

SEE ALSO:

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Resources

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! ✈️ Learn More

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

Quote of the Day
"Anyone who lives in a city could create a tour business, and it costs virtually nothing to start! All I spend on each hiking tour is my time, and it’s almost all pure profit."
—Alexandra Klein #SideHustleSchool

Sponsors & Gratitude

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Sign up by clicking the button below, and you’ll receive their most popular Trial Set—a 13 dollar value—for FREE when you cover the shipping.💈 Get it Here

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.
Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!


To infinity and beyond,

Chris Guillebeau

Renegade Museum Tour Guide Earns $2 Million

What It’s About

A man from New York City goes on a forgettable date but falls in love with the idea of creating his own museum tour company.

[podcast_details]

Words of Wisdom

A large part of Nick Gray’s success with his touring side hustle, Renegade Museum Hack, is the fact that he stays driven by a simple goal: showing people that museums are awesome. He took something that some people would consider boring, and found a way to engage his tour attendees in a more interesting way.

Is there something out there that’s considered boring that you could do better?

Fun Fact

While Nick spent his working weeks selling avionics equipment—a job he happened to be happy at—he started spending every weekend at the Met. He began offering free tours of The Met to his friends and family, which mainly consisted of showing them his favorite things. He says he was having so much fun doing the tours that the first time someone tried to offer him money at the end—around $20—he declined their offer.

Notes from Chris

Episode 100

For some, a trip to the museum promises to be a deep and meaningful experience rich with our cultural history. But for others, it can be considered on par with watching paint dry. As humans, we have this deep-seated love of storytelling that draws us in and helps us to relate and connect. Museums are a perfect environment for this, but sometimes that crucial storytelling aspect gets pushed to the back burner in lieu of education and facts.

In today’s story, a New York City man is seeking to change the way that people experience museums by offering unconventional tours that peel back the curtain of modern exhibits revealing the amazing stories behind the history.

He began offering free tours of the museum to his friends and family, which mainly consisted of showing them his favorite things, but these weekend tours quickly became a very full-time hobby. Given his newfound love for museums and desire to share it, he decided to set up a side business offering fun, non-traditional, “renegade” tours at the world’s best museums specifically for people who don’t think they like museums.

Several years later, it’s safe to say all of this has been a huge success. In its first year, Museum Hack made about $40,000 in sales, and in the following year this increased—no joke—twelvefold. 2016 marked his fourth year in business bringing in over $2 million in sales, and Museum Hack now has more than 50 guides, offering tours in New York, Washington DC, Chicago and San Francisco.

MENTIONED IN THIS EPISODE:

  • Museum Hack: Learn more about the unconventional tours that Nick and his team offer on his website—these aren’t your Grandma’s museum tours!
  • The Metropolitan Museum of Art: The iconic site where Nick’s love for museums blossomed

SEE ALSO:

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

Chris Guillebeau

P.S. If you have a moment, will you answer a quick survey for my podcast network? They want to know more about who’s listening. 🙂

Resources

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Learn More

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! ✈️ Learn More

Quote of the Day
"Do it for your friends first! I spent hundreds of hours giving my friends free museum tours so I could create an entirely new product, and this feedback from them in combination with their word of mouth advertising is what helped me launch my business."
—Nick Gray #SideHustleSchool

Sponsors & Gratitude

Get a premium Indochino Suit for just $389!

Side Hustle School is brought to you by Indochino, the company that’s reinventing men’s fashion.

Go to Indochino.com to get any premium Indochino suit for just $389, plus free shipping, when you use promo code HUSTLE at checkout. 🤵 Get it Here

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference! ✅

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.
Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!


To infinity and beyond,

Chris Guillebeau