What It's About
Tour guide “trip hacks” his way to $1,500/month using YouTube.
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.
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
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
- 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
- Florida Man Leads Scooter Tours After Watching Macklemore Video: Had a broken keyboard, bought a broken keyboard: this corporate refugee relocates to Florida and kicks off a new hustle leading adult scooter tours
- Renegade Museum Tour Guide Earns $2 Million: A man in New York City proves that with enough passion and innovation a side hustle can thrive in museums
Download Episodes By Months
Season 6 (2022): JAN | FEB | MAR | APR |
Season 5 (2021): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |
Season 4 (2020): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |
Season 3 (2019): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |
Season 2 (2018): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |
Season 1 (2017): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |
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!
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.
Quote of the Day
Sponsors & Gratitude
Side Hustle School is brought to you by CardsForTravel.com. Use travel hacking to see the world!
When you apply for their most popular, small business rewards card, you can earn 80,000 Bonus Points—enough for three round-trip plane tickets or $1,000 in travel credits. Check out this limited time offer! ✈️
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.
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,