Tag: Tourism

Physician Assistant Peru-ses Machu Picchu Treks

What It’s About

A traveler and a guide team up to start their own tourism business.

[podcast_details]

Words of Wisdom

For those interested in starting a travel side hustle, Kevin suggests, “Become an expert in your field and travel region that you are looking to service. This will make you and your company a better resource for your potential customers that are interested in your service.”

Fun Fact

Although the delicate nature of Machu Picchu means numbers are heavily restricted, it is still one of the world’s most popular tourist attractions. In 2018 over 1.5 million people visited the site throughout the year, an average of 4300 per day.

Notes from Chris

Episode 1408
Kevin Groh has always loved to travel. In 2015 he was working as a Physician Assistant when he decided to visit Machu Picchu. The ancient city is nestled high in the mountains of Peru, and getting there is a formidable four-day task taking adventurers through the majestic scenery and exhaustive mountain passes. The conditions require that anyone trekking there must be accompanied by a guide.

For Kevin, that guide was a local named David Villagra. David grew up in a farming town nearby and worked for a local tour operator. However, he’d always dreamed of starting his own company to guide visitors from around the world through his own backyard.

In fact, he’d tried once before, and failed. Guiding is a serious business in Cusco, the historical city near Machu Picchu, and competition is fierce. Without any experience in marketing, he couldn’t compete with the larger local businesses. As he explained this problem to Kevin on day two of the trek, Kevin’s mind began to wander.

He had seen first hand what a fantastic experience the trek was, and put forth an idea. If David could handle all the logistics in Peru, he’d find a way to market to tourists in the U.S. In a handshake deal on day four of the hike they agreed to start Cachi Life, a travel company specializing in tours of the region.

David would arrange permits for the hikers, local porters, equipment and food. Kevin would build a web presence and handle all the marketing. Once Kevin returned stateside, he got to work.

With each happy customer the word of mouth spread, and Cachi Life soon had referral business coming in on top of the new business being funneled by their content marketing. By the beginning of 2020, the side hustle was making sixty thousand dollars per year!

But… you know the next part of the story. COVID-19 became a cloud covering the summit, making the next steps more a little foggy. The Peruvian border was closed for several months in 2020. This means that the tourism industry has taken a huge hit. A hit extended to Cachi Life.

While upsetting, Kevin still has his day job and knows tourism will be back in full swing before too long. In fact, the region is already reopening this month to visitors from select countries.

He’s been taking the time to increase the amount of content he produces to keep Cachi at the forefront of discussion. Furthermore, to attract people who may want more of a DIY approach to exploring Peru he and David are creating a Peru travel guide that they hope will help produce additional, non-tour related income. As soon as it’s feasible, they also plan to expand their tours to Bolivia and Mexico.

 

 

MENTIONED IN THIS EPISODE:

  • We’ll be able to travel again some day! Start dreaming about going to Peru at Kevin’s website, CachiLife.com.

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
"Become an expert in your field and travel region that you are looking to service. This will make you and your company a better resource for your potential customers that are interested in your service."
—Kevin Groh #SideHustleSchool

Sponsors & Gratitude

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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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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

Globetrotting Sommelier Leads Popular Wine Tours

What It’s About

A wine bar owner puts a cork in his business, finding more fruit in hosting tours.

[podcast_details]

Words of Wisdom

While he hasn’t had any formal training, Heath is confident about one thing: service is something that people always notice. This nugget has allowed him to launch his own business, but also to travel around the world doing something that he loves. Now that’s something we can all raise a glass to.

Fun Fact

Heath’s business was born out of two simple questions: how would he like to eat and drink around the world, and how he could get others to pay for it.

Notes from Chris

Episode 1088
Heath Porter has been a sommelier and a food and beverage professional for more than twenty-five years. It was his passion for food and wine that led to the birth of his then-hustle, now-full time work at Heathen Wine Tours.

What inspired his love of wine? Well, Heath grew up in a dry county in North Alabama, where alcohol was not allowed. From his late teen years onward, he moved around to work at wine bars and holiday resorts in Hawaii, West Virginia, and Miami.

Traveling, meeting and tasting with winemakers was simply part of his job… a part that Heath very much enjoyed. He acquired a great deal of experience—so much so that guests, who were impressed by his tastings and classes, began to ask about the possibility of tagging along on his next wine adventure.

Heath didn’t think much about it at first. But finally, one day he simply said he would book a group trip if they would give him a credit card number. To his surprise, his regulars did so. This wasn’t cheap: at around $2,000 per person, Heath booked a trip to wine country Santa Barbara, California for his party of ten.

With tremendous positive feedback from his guests—and some of them remarking that he should charge more than he did—he organized another trip to Italy. As the guests returned to request yet another trip, he found himself visiting Spain and France … and then Chile. All of this took place from 2014 to 2018, while he was still working full-time at his last wine bar.

His first thought was to plan trips to places where he knew the most winemakers and owners. The idea was to be able to bring his guests to cellars and vineyards where they could eat and drink like family. This obviously required some degree of familiarity and comfort with others – something which Heath had cultivated over many years in his career.

Soon, friends of friends were booking tours. Those that attended enjoyed the experience so much that for the first five years about 80% of Heath’s business was from repeat customers.

In 2018, he realized that he likely had enough trips booked to look at doing this full-time. While his first trip had made him just a couple of thousand dollars after expenses, he had viewed it mostly as a fun experience he did apart from his real job. Now, he looked at what it would take to make the tours more of a steady gig.

As with other luxury products and experiences, it wasn’t easy for Heath to price his products. He did so by making comparisons with similar tours and then making sure that he could offer better value—typically by offering more while charging less. This he says, is what has allowed his business to take off. In fact, a tour he organized to essentially serve as an advertisement ended up netting him over $10,000.

On average, Heath is able to make a 40% profit margin on most tours. At the end of each one, he raises a glass or two in celebration … and then he gets ready for the next trip.

 

 

MENTIONED IN THIS EPISODE:

  • Heathen Wine Tours: Want to go on your own wine tour? Learn more about Heath and his business at his website.

SEE ALSO:

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

Yours in the revolution,

cg-sig-newsletter

Resources

WEB HOSTING @ $2.49/MONTH

Want to build any kind of website for your hustle? If so, you'll need somewhere to host it! This is the reliable company I've used for many websites. It's cheap, flexible, and offers support 24-7.

Get your own hosting plan for just $2.49 a month!
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
"The one thing that always prevails is service. That goes for any business in the world: service is always something people will notice and come back for."
—Heath Porter #SideHustleSchool

Sponsors & Gratitude

Try ShipStation for 60 Days FREE!

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

To get a 30-day trial AND an additional month free, click the microphone at the top of their page and enter the word HUSTLE.
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

Adventurous Couple Turns Travel Itineraries Into Cash

What It’s About

An adventurous couple turns Romanian travel itineraries into cash.

[podcast_details]

Words of Wisdom

Sometimes it takes a while to get up and running. At the same time, in this story, we can identify a few things they would do differently if starting now that might save them some of that time (e.g. – fewer packages, track what’s working, focus on lead generation). Start small, pay attention to what works, and then use that knowledge to expand your offerings!

Fun Fact

There are a ton of reasons to visit Romania, but road trip enthusiasts would be remiss if they didn’t check out the beautiful, 56 mile stretch of road known as the Transfagarasan Highway. Built between 1970 and 1974 by military forces following the 1968 invasion of Czechoslovakia by the Soviets, it was considered a strategic military route to cross the mountains in the event the Soviets attempted a similar move into Romania.

Notes from Chris

Episode 959

Besides packing, many consider the return trip home one of the worst parts of travel. The return trip signals the end of an adventure, sometimes a return to a less exciting routine. For others, the journey—lacking the anticipation that comes with starting a new adventure—just seems like it takes far too long.

Returning from a weekend trip to the mountains, Bucharest, Romania-based Corina Preda and her husband, Florin, shared some of these thoughts.

Driving back to the city meant a return to the hustle and bustle of their busy schedules and jobs in human resources and the pharmaceutical field. While they had little to complain about, they would have loved a few more days away.

Driving along the country Romanian roads, they were already looking forward to their next adventure and discussed ideas for what they wanted to do next. They both immediately said “traveling,” which is not surprising since it’s something they’ve both loved since they were kids.

But then one of them suggested, “Wouldn’t it be great to have a business in travel?” Excitement filled the car, and soon they decided on starting a travel agency offering guided trips and custom experiences of their beloved Romania.

Corina loved researching and planning itineraries, and Florin loved sharing cool places and things with people, so the idea was perfect! Not only did they love showing off their home country, but a travel business could earn extra money and allow them to travel more themselves. It was a win all around … or at least it might be.

They quickly discovered that travel agencies in Romania require licenses and training. These education requirements for licensing took several months, and Corina and Florin used this time wisely. Whatever time wasn’t spent at work or in class was spent developing their new business.

Finally, their training was complete—and Secret Romania was officially open for business.

Things, in the beginning, were slow to start, but today, in Secret Romania’s fourth year, this duo are consistently bringing in €1,300 euros per month, roughly $17,000 per year in US dollars … and also known as “a lot of money” in Romania.

These extra funds allowed Corina and Florin to save money and to take more trips of their own. The bonus income from their side hustle also gives Florin more flexibility to reduce his work schedule, which he loves.

The work continues. Corina and Florin are excitedly looking ahead, refining their marketing efforts and optimizing their website to showcase their homeland. Most of all, they never stop learning and never stop thinking about their next adventure.

 

 

MENTIONED IN THIS EPISODE:

  • Secret Romania: Learn more about the secret wonders of Romania over on Corina & Florin’s website!
  • WordPress: Corina and Florin used WordPress to set up their site, and here you can learn how to install your own WordPress site in 5 minutes

 

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

RELIABLE WEBHOST FOR $2.49/MONTH

Want to build any kind of website for your hustle? If so, you'll need somewhere to host it! This is the reliable company I've used for my past 5 websites. It's cheap, flexible, and you can get support 24 hours a day.

Get your own hosting plan for just $2.49 a month!
Learn More

Quote of the Day
"Finding time and motivation to work after you get home from your full-time job can be challenging. To help, set a long-term goal and visualize it every time you find yourself ‘not in the mood’ to work."
—Corina & Florin Preda #SideHustleSchool

Sponsors & Gratitude

Don't Do Business Without It

Side Hustle School is brought to you by American Express.

No matter what you do in business, from working nine-to-five to working five-to-nine, it’s easier when you don’t go it alone. Get the powerful backing of American Express—don't do business without it! 💳 Visit American Express

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

Anchors Aweigh! Graphic Designer Leads Guided Sailing Tours

What It’s About

An Aussie sails away to Croatia on a strong current of profits.

[podcast_details]

Words of Wisdom

Although starting out, Chris said he did have to get creative to get noticed by Google’s search engine. He did his best to get linked to as many websites and blogs as possible. It was about saying, “Yes.” If the opportunity to get interviewed by a blog or company came along, he’d take it.

This “Yes” mentality paid off in 2018 when he attracted the attention of Shark Tank Australia and found himself pitching his brand on national TV. That spot earned him some mentoring from the Sharkies!

Fun Fact

Although it probably wasn’t fun at the time, Chris’ first tour nearly didn’t happen because of a PayPal fiasco. PayPal froze his account right before he had to use his funds to pay for the boat. They weren’t going to release the funds until the tour was delivered—but he couldn’t deliver the tour without the funds! Fortunately for both Chris and us, he secured a loan from friends and family to get his first tour off the ground and into the water!

Notes from Chris

Episode 884

Approaching his 30th birthday, Australian Chris Tabone felt it was time for a change. An established graphic designer for nearly ten years, he decided to take a year off to travel the world. But after nine months of hostel stays and banana pancakes, money was in short supply and Chris was thinking of ending his globetrotting then and there.

Not quite ready to cut the adventure short, he applied for a tour guide position and got the job. It only paid $78 a day, but his meals and accommodations were covered. Plus, he’d get to travel all around Europe for free!

He ended up staying in the role for several years, learning a lot about the industry. After a while, many of his typical passengers (who were in their 20s) started asking him what tours he would recommend when they returned in a few years.

They were getting too old for youth accommodations but also didn’t want to end up on a cruise ship that served Baked Alaska after ballroom dancing and bingo. This was when Chris spotted a gap in the market. The demographic of young professionals in their late twenties to late thirties just wasn’t getting much love from the guided tour industry.

So, he decided an experiment was in order…

The next off-season, Chris went back home to Melbourne and put pen to paper, figuring out how he could create something for this age group.

Then, he leveraged his large network of industry contacts and made the decision to sell sailing tours in Croatia for the following summer. These Mediterranean trips were big winners and they appealed perfectly to his demographic.

Using his background in design, Chris put together a website, created social media accounts, and started contacting all of his old passengers through Facebook. He was able to convince 40 of them to trust him with the idea that he could take them on a spectacular adventure—only now with his own company, Koda Sail.

the Koda Sail tours run between $1,200 to $1,500 per person (up from ~$900 per person on his first tour). He’s upgraded his selection to four boats that run during the summer months. The tours run for seven days and specifically target young professionals.

The business currently brings in just under $300,000 a year, with word of mouth still being his number one marketing tool.

For Chris, it’s full steam ahead with no plans of taking his hands off the rudder anytime soon. He plans to add a new destination every year, starting this year with Turkey. Italy, the Greek Islands, Asia, and the Caribbean are also in the works.

 

 

MENTIONED IN THIS EPISODE:

  • Koda Sail: Set sail over to Chris’ website yourself to learn more about this seafaring side hustle!

 

SEE ALSO:

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

Yours in the revolution,

cg-sig-newsletter

Resources

WEB HOSTING @ $2.49/MONTH

Want to build any kind of website for your hustle? If so, you'll need somewhere to host it! This is the reliable company I've used for many websites. It's cheap, flexible, and offers support 24-7.

Get your own hosting plan for just $2.49 a month!
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
"Really think through everything and don’t rush into making decisions, especially financial ones, that could jeopardize everything you’ve worked hard to achieve. I feel like I’ve been successful because of calculated moves that have been done with lots of patience."
—Chris Tabone #SideHustleSchool

Sponsors & Gratitude

Don't Do Business Without It

Side Hustle School is brought to you by American Express.

No matter what you do in business, from working nine-to-five to working five-to-nine, it’s easier when you don’t go it alone. Get the powerful backing of American Express—don't do business without it! 💳 Visit American Express

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

Amsterdam Bike Tours Become Passive Profit Center

What It’s About

Frustrated by mediocrity in the tourism industry, an Amsterdam local sets something in motion.

[podcast_details]

Words of Wisdom

For anyone looking to start a similar business, Vince says it’s paramount to get some time under your belt working for an established company first. Learn your trade and look for the areas that you would improve and do differently; this will give you the starting point for your own venture.

Fun Fact

Vince was in San Francisco a couple of months after he started the business and met with fellow featured Side Hustler, Alexandra (from Ep 158), to get her tips and tricks for a tour-based business!

Notes from Chris

Episode 837
Vincent Linssen’s world travels had left him broke and looking for a fun way to earn some extra cash. Despite returning home to The Netherlands to a full-time job at one of Amsterdam’s major financial firms, he found himself in need of some extra cash to cover his expenses.

Vince had always wanted to be a tour guide and felt he’d taken enough walking tours in other cities in the world to have a go himself. It was a time in his life where he had nothing to lose, so he figured he may as well give it a shot.

He joined a company where he could give tours of the city on big yellow bikes. For two months, Vince gave ten tours a week, scheduled around his day job, and received a crash-course in the art of big city tours. However, he didn’t appreciate the way certain parts of the company were organized—and he felt he could do a much better job.

A few weeks later on his morning commute, Vince tuned into episode 158 of the Side Hustle School podcast and heard about the Urban Hiking tour company someone had set up in San Francisco. It gave him an idea!

By the end of the episode, his side hustle Amsterdam Experiences was already coming to life.

The income for Amsterdam Experiences depends a lot on seasonal demand. Between March and November, they can earn profits of up to 20,000 EUR per month. But, in the winter months, this can drop down to just a couple of hundred.

Despite achieving such success, Vince and Stephan still work their day jobs and have instead hired tour guides to help them scale the business. Because of their high TripAdvisor rating, many tour guides find them and offer their services. But they also look for guides through their personal networks.

Vince says a good tour guide should be local, friendly, and good at improvisation. If you can think on your feet, tell a good story, and hold a group’s attention, you’ve probably got what it takes!

For anyone looking to start a similar business, Vince says it’s paramount to get some time under your belt working for an established company first. Learn your trade and look for the areas that you would improve and do differently—this will give you the starting point for your own venture.

Looking ahead, Vince and Stephan want to delegate and automate their operation. They both have lofty goals—like starting a tech company to fight global warming on a large, systematic scale—so they want to create a “set it and occasionally check on it” strategy.

They’re not just spinning their wheels … they’re building a real business.

MENTIONED IN THIS EPISODE:

  • Amsterdam Experiences: Get an insider’s perspective of everything that makes Amsterdam such an amazing place over on Vince’s website!
  • Squarespace: The website building platform that Vince used to create his website
  • Urban Hiker Climbs to Steep Success in San Francisco: A project manager turns a passion for her city into a substantial side income of $50,000 a year. This is the episode that inspired Vince to get started!

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
"I noticed that those who are successful have a few things in common: they show grit, dedicate serious time to it, and have a partner to support them. It’s a very competitive market, so you have to be different and/or better than the competition in some way."
—Vincent Linssen #SideHustleSchool

Sponsors & Gratitude

Try ShipStation for 60 Days FREE!

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

To get a 30-day trial AND an additional month free, click the microphone at the top of their page and enter the word HUSTLE.
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

Interior Designer Starts Boutique Airbnb Alternative

What It’s About

An interior designer creates an upgraded, Airbnb experience for the trendy and fabulous.

[podcast_details]

Words of Wisdom

Whenever something like this takes off, it often creates additional opportunities in the margins for people like Allison to flourish. Even though she’s trying to do her own thing, she’s using the platforms of Airbnb and others. Arguably, they have enabled her to pursue this alternative vision. Pay attention!

Fun Fact

Allison learned a lot about entrepreneurial grit and salesmanship when she lived in New York. Not only did she sell copiers on Wall Street, but she was taking classes towards a degree in interior design at NYU in the evenings.

Notes from Chris

Episode 833

Though formally trained in advertising and marketing at Southern Methodist University in Dallas, Allison Crawford’s real passion was somewhere else: interior design. Even as she sold radio advertising in Austin, moved to sell copiers on Wall Street for a while, and then moved back to Texas to direct the marketing efforts of a car company, she was always learning about interior design. While in New York, she took night classes at NYU.

But rather than working for an interior design company, Allison created her own gigs on the side by flipping houses once she moved back to Dallas. It was grueling work: finding a house, bidding for it, renovating the property, designing the interior, and then—finally—selling it, hoping to profit.

It was a bit less thrilling than she’d hoped, and when one deal went sour and Allison ended up losing a lot of money, she decided the house flipping game wasn’t where she belonged.

She did, however, really like the part where she handled the interior design of the properties.

When a handful of friends offered to pay Allison for her skill, a lightbulb went off: she should try starting her own home design service.

Just a few months later, in 2015, Allison Crawford Design debuted. She built a portfolio of happy clients in a matter of months, and took her hard-earned cash to Los Angeles for the annual “Design Week” festival.

Still, this wasn’t the final answer either…

In Los Angeles, she learned a lot and made valuable connections, but the festival itself wasn’t where the most dramatic change happened. That happened in her Airbnb.

Let’s just say Allison’s first short-term rental experience on the platform was less than ideal. And it made her wonder: “Why isn’t there a chain of properties that fill the void between common home rentals and boutique hotels?”

She went home at the end of the week curious and eager. And what she found was intriguing: no other company owned, designed, and marketed boutique short-term rentals all under one umbrella. Lots of companies do one, or maybe two of those things—but never all three.

Allison knew she could do it. She’d bought and sold homes, she was an interior designer, and she was an experienced marketer. Allison had a trio of skills that nobody else seemed to be using all together—so she jumped in.

By Summer of 2017, HOTELette had its first property in Nashville. Not long after, she added two more properties in Austin and Dallas. She’s now looking at a fourth location in 2020, a furniture line, and maybe even a reality TV show.

Allison’s not one to take all the credit. She says she has an incredible team behind her that she’s put together over the last three years: three city property managers, a digital shop manager, an assistant, a bookkeeper, and marketing manager. Drawing others into the dream of Hotelette—from customers to contractors—has been a lot more rewarding than selling copiers or flipping houses.

 

 

MENTIONED IN THIS EPISODE:

  • HOTELette: If you’d like to learn more about the boutique experiences Allison is creating, head on over to her website!
  • Airbnb, HomeAway, & VRBO: Three of the property rental platforms that Allison used to get HOTELette 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

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

RELIABLE WEBHOST FOR $2.49/MONTH

Want to build any kind of website for your hustle? If so, you'll need somewhere to host it! This is the reliable company I've used for my past 5 websites. It's cheap, flexible, and you can get support 24 hours a day.

Get your own hosting plan for just $2.49 a month!
Learn More

Quote of the Day
"I think that it’s important to celebrate the small victories with your team. Getting a business up and running isn’t always glamorous, and consistent reminders of our progress and growth keeps driving us forward."
—Allison Crawford #SideHustleSchool

Sponsors & Gratitude

Don't Do Business Without It

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To infinity and beyond,

Chris Guillebeau

ABC News Reporter Dishes Out Profitable Pizza Tour

What It’s About

Breaking News — a reporter helps others get a taste of the best pizza Chicago has to offer.

[podcast_details]

Words of Wisdom

I think the key to long-term success here is getting listed in guide books and city directories and all of the promotional tourism materials that are distributed every year. For most of those things, getting listed and endorsed can take a while, but once you’re there, you’ll just be renewed every year.

Fun Fact

Working as a food reporter since 2003 with 13 James Beard Awards under his belt, Steve felt that he had to set the record straight about Chicago’s pizza scene. So, like any great reporter, Steve spent time in the field gathering research. He spent the better part of a year sampling pizza from 185 locations which led to a shocking revelation: Chicago is a “thin town” with the majority of pizzerias specializing in tavern-style pizza that’s thin, crisp, and square-cut—not deep-dish!

Notes from Chris

Episode 809
Steve Dolinsky wears many hats. He’s the food reporter for Chicago’s ABC 7 news team. He runs two podcasts, and he offers media training outside of Chicago for chefs. He’s a veritable curator of culinary experiences. He’s also the new owner of Pizza City USA Tours, offering weekly pizza tours, by both bus and foot.

Why did he start this side hustle when he’s already got so much going on?

Well, he had a book coming out in the fall of 2018 called Pizza City USA. Oh yeah, he’s also an author. Steve figured, “Hey, why not start a tour business to help bring the book to life?”

There was only one other dedicated pizza tour business in Chicago, and a lot of pizza … not to mention a lot of visitors passing through.

He knew that Chicago pizza had been reduced to the deep-dish and stuffed cliches. But hold the pepperoni—there’s more to midwest pizza than only deep-dish and stuffed.

What about thin? Tavern? Artisanal? Neapolitan? Roman? Sicilian? Detroit? Steve dared to challenge the status quo with these questions. He estimated there were at least 10 distinct styles in his Chicago pizza roundup.

So, he decided to launch a weekly tour that highlighted these differences, showing guests four styles of pizza in three hours.

He started with a Saturday bus tour to four neighborhoods. Next, he added three walking tours that each focused on a single neighborhood.

Throughout the tours, Steve dazzles guests with his encyclopedic knowledge of Chicago history while leading his groups into the belly of the beast… the fiery kitchens themselves to show people exactly how the pies are made.

Here, one can expect to engage in lively discussions with the owners and gain a better understanding of the families behind the sauce.

So far, business has been pizza-rific with Steve adding five tour guides to the mix. This salty bunch are affectionately referred to as “doughcents” (experts who know Chicago pizza and would love to tell you all about it). They were trained by Steve and help lead other tours, as well as private events.

In the colder months he offers bus tours only (after all, this is Chicago we’re talking about). When warmer weather returns in the spring, he’ll bring back the walking tours as well as a 3rd Thursday Pizza Crawl.

What’s next for Pizza City USA Tours? Steve’s considering a 2nd edition of his book, as well as working towards consistent sell-out tours. Once he achieves that, he’d like to add another walking tour. That would be a slice of heaven.

MENTIONED IN THIS EPISODE:

  • Pizza City USA Tours: Take a slice out of Chicago’s pizza scene—learn more over on Steve’s website!

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
"It’s important to get media placements. If no one knows about your offering or business, it doesn’t matter how good it is. People have to hear about you."
—Steve Dolinsky #SideHustleSchool

Sponsors & Gratitude

Try ShipStation for 60 Days FREE!

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

To get a 30-day trial AND an additional month free, click the microphone at the top of their page and enter the word HUSTLE.
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

Boston Designers Open Authentic Arts & Crafts Shop for Visitors

What It’s About

Two friends bring the best of Boston local to 20 million the world over!

[podcast_details]

Words of Wisdom

It’s no small thing to start a retail shop and operate it for three years while you’re also running a design agency. And this is why it’s good to start with a pop-up shop. Also, leverage your contacts! You can’t do something like this on your own and without a lot of resources … $25k isn’t much for a project like this. Their greatest asset was the relationships they had.

Fun Fact

Here are a couple facts about Beantown that you may not know:

1. You won’t find any “Happy Hour” signs in the local Boston pub. The typical post-work drink deals have been banned since 1984.

2. A favorite American sweet snack for decades, the Fig Newton, is actually named after the Boston suburb of Newton, Massachusetts.

Notes from Chris

Episode 676
Susan Battista and Fritz Klaetke love Boston almost as much as they enjoy working with each other. They’re both senior partners at the creative agency Fritz founded in college, Visual Dialogue. Over the years, the pair have started a number of side hustles outside their day jobs.

It was on a trip to Fritz’s native Detroit that they would find their next big idea. Wandering down the high street, they came across a unique little shop which showcased local artist’s creations. They had trinkets and t-shirts and tasty treats which really represented the region’s history and culture.

They felt that their beloved Boston needed a similar type of shop. Every tourist-centric shop focused on cliche stuffed lobsters and your usual sports t-shirts. There was nothing which represented and championed the life, history, art, and culture of this beautiful and important city.

When the pair returned home, they began to look at why a shop like this didn’t exist, and it quickly became clear. The cost of rent in Boston’s most trafficked locations was too high for local artists to sell their goods, which forced them to sell hours away in far-off suburbs, away from the eyes of most visitors.

Susan and Fritz decided to create a shop which brought out the best of Boston to those visitors. They would set up a store somewhere with high visibility and enable artists to share their wares. They gave the concept a name—1630 Boston, after the year the city was founded—and set about putting their plan into motion.

To test their idea, they decided they would create a pop-up shop. They’d run it for a weekend in a prime location and see if they gathered interest. If not, they could walk away knowing they tried.

They looked to their client base at Visual Dialogue and approached a property management company they’d been working with. They were able to land a weekend-long spot—in a location which usually costs $20,000 a month—on Boston’s Newbury Street.

With the property in place, the official date of the pop-up was set to five weeks away, in November of 2015, which gave them a strict deadline to hit. They had no inventory, no POS system, no merchandising and no website.

When the weekend finally rolled around, the pop-up was a resounding success. Local people and tourists alike were drawn to the shop to see what they were selling, both out of curiosity and a desire to buy. The pair had an antique bell on their desk which they rang every time they made a sale, and they found themselves ringing it a lot. That is … until someone asked if they could buy it.

With the initial success, Susan and Fritz knew they had an idea they could move forward with.

The startup costs for 1630 Boston were around $25,000. This was made up of money they saved, and what they reinvested back into the business. And their profits average at approximately $10,000 per month.

Looking to the future, 1630 Boston is going to build more of an online store presence to increase their reach and make Boston’s art, culture, and history available to people all over the world.

MENTIONED IN THIS EPISODE:

  • 1630 Boston: Learn more about Boston’s nearly 400-year history through the products on Susan’s website that showcase the history, intellect, pastimes, and local lore of New England’s cultural capital

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
"Shadow someone who is doing what you’d like to do so you have a better sense of ‘all the hats’ required."
—Susan Battista #SideHustleSchool

Sponsors & Gratitude

Get Your Logo Today With Logojoy!

Side Hustle School is brought to you by Logojoy, an online tool that uses artificial intelligence to help you design a beautiful, custom logo.

Try Logojoy today and get 20% off any logo package when you visit logojoy.com/hustle.


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

Food Tour Guide Chomps Down on $100,000 Profit

What It’s About

A Mile High food tour hits the right spot.

[podcast_details]

Words of Wisdom

Today’s story is a great contrast to Ep. 508 because there are two ways of building this kind of business: either it’s dependent on you, or it’s built around a brand. In Ep. 508, Rob is doing all the tours himself. In this story, Jessica is building more of a tour business so that she can go to Mexico and still get paid for tours taking place in Denver. The question is: which is better for you?

Fun Fact

Not sure exactly what Denver has to offer in the food spectrum? The Mile High City’s tastes date back to the era of pioneers who spent their nights roasting buffalo and potatoes over campfires along the South Platte River. While they still have a soft spot for anything involving meat and potatoes, hatch chile peppers are a staple along with smothered burritos.

Notes from Chris

Episode 648
Jessica Baumgart had made a lot of active choices. The Denver, Colorado native was working in marketing when she and her husband took a year-long career break traveling through 5 continents. They did this after saving up for several years and downsizing most of their possessions.

When they came home, Jessica didn’t want to jump straight back into the same kind of work. She needed something new, and she found it in at least two new opportunities. The first was a full-time business she started teaching private cooking classes. On the side, she moonlighted for a company that provided guided food tours.

She discovered that she liked leading tours for strangers more than she liked cooking for them. Maybe it was because someone else cleaned up—maybe it was because she got to connect more instead of slaving away in the kitchen. Whatever it is, she liked the tour guide biz, and she had some ideas on how she’d do it differently if it was her own project.

8 months later, she made it her own project, launching a new brand called Savor Denver Food Tours*. Each tour lasts about 3 hours and covers 6 tastings around the city. It followed the same format of other tours, with good food and rotating locations—but this iteration had her own spin. It focused more on local chefs and local ingredients, to truly give a memorable and unique experience.

5 days after her website went up, Jessica received her first booking. She says she was caught off guard at how quickly it got started. All of a sudden, her planning became real.

After 3 months, she was guiding tours 7 days a week… and desperately trying to hire other guides to take some of the stress off her plate so she could turn it into a real business.

It’s now been almost a year since Jessica launched Savor Denver. How fast can you grow a tour business in one year?

Well, the proof is in the pudding (or decadent hatch queso)!

She currently hosts around 350-450 guests per month, and the business is on track to gross $200,000 with 50% profit margins. The best part? She accomplished this spending only $3,000 in startup costs!

As Savor Denver grew, she was working less and less on her day job/other business of cooking lessons. She finally decided to let it go and focus full-time on the tours. She recently added a cocktail tour to her repertoire and hopes to launch more neighborhood tours in response to demand.

*Producer side note: since the airing of this episode, Jessica changed her business name from Savor Denver to Delicious Denver Food Tours.

MENTIONED IN THIS EPISODE:

  • Delicious Denver Food Tours: The Mile High City has so much to offer in the way of food—be sure to check out Jessica’s website if you ever find yourself in the neighborhood! (note: Jessica has changed her business name from Savor Denver Food Tours to Delicious after the original recording)

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
"I absolutely love having control of my time. Although it’s not always straightforward, it’s amazing to be able to go to the gym when I want, walk my dog, work in my pj’s or travel as much as I want. I also get to visit every restaurant I’ve ever wanted to try in Denver and write it off as a business expense."
—Jessica Baumgart #SideHustleSchool

Sponsors & Gratitude

Try ShipStation for 60 Days FREE!

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

To get a 30-day trial AND an additional month free, click the microphone at the top of their page and enter the word HUSTLE.
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

Hit the Streets With These Chicago Walking Tours

What It’s About

The tours are “free,” but this creative Chicago guide still earns $2,500/month from them.

[podcast_details]

Words of Wisdom

Jeff has found his ‘free’ business model to be more beneficial than tours that charge per person. However, he stressed the need to maintain a five-star rating and grow his reviews. This is critical. Just like he was skeptical on his first walking tour, some people question his service’s legitimacy because it advertises as free. The rating assures guests that he’s a legit business.

Fun Fact

There’s a lot of interesting (albeit sordid) history in Chicago, and Jeff’s Free Chicago Walking Tours takes advantage of that with his Chicago Crime & Gangster Tour. On this tour, you’ll learn how the Chicago mafia came to power as well as take you to some lesser known, infamous Chicago mob hangouts!

Notes from Chris

Episode 643

Jeff Mikos has been the manager of a pet care business for a large grocery cooperative. He’s also dabbled in real estate, with two rental properties, including one he manages himself.

A few years back, Jeff and his wife had an experience while traveling that ended up turning into an accidental side hustle. On an extended trip through South America, they stumbled upon a free city walking tour in Santiago, Chile. They were skeptical at first—how good could a free tour be?—but they decided to try it out. They ended up enjoying it so much that they sought the tours out in every city they visited.

While on a tour in Quito, Ecuador, Jeff’s idea sprouted legs and took a walk of its own. He thought that implementing this model in his hometown of Chicago might have a walking chance. Jeff did some research and discovered this model had a low barrier to entry. “Who wouldn’t want a free walking tour?”

Jeff got to work!

He and his wife spent an entire weekend passing out brochures to every hotel and hostel in the area. Jeff racked up more steps than his pedometer knew what to do with but said it was hard to determine the ROI because there was no way to track it. (There weren’t any coupon codes or anything else that separated signups from one source versus any other.)

Once his site was published, people began signing up. He remembers looking at his wife and thinking, “Huh, we’ve got guests!”

Since its creation, Free Chicago Walking Tours went from nothing to a 5 star TripAdvisor tour company with hundreds of reviews. Jeff has maintained that five-star rating, earning a Certificate of Excellence from TripAdvisor. They walk a fine line!

So far, they’ve led more than 15,000 guests on the tours, and it’s regularly bringing in more than $2,500/month in extra income. It’s not a ton of money, but at this point, the business is low-maintenance—not completely passive income, but close.

He’d like to expand his operations to include additional cities in the midwest. He supplements his income with the private tours and hopes to be running even more tours next year.

 

 

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

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RELIABLE WEBHOST FOR $2.49/MONTH

Want to build any kind of website for your hustle? If so, you'll need somewhere to host it! This is the reliable company I've used for my past 5 websites. It's cheap, flexible, and you can get support 24 hours a day.

Get your own hosting plan for just $2.49 a month!
Learn More

Quote of the Day
"Time’s up. Stop reading the blogs. Quit talking about it to your friends and family. Put down the books… You’re going to learn and have better questions the books and blogs can help answer once you start doing something."
—Jeff Mikos #SideHustleSchool

Sponsors & Gratitude

CRAZY ENOUGH TO WORK

This week, Side Hustle School is brought to you by Crazy Enough to Work, a popular podcast and film series. 📈

When the rest of the world is still zigging, some companies know when it’s time to zag. Elizabeth Banks has teamed up with State Street Global Advisors to make a series of podcasts and films that uncover the bold moves mid-cap companies make to thrive and survive. Listen 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