9 min 42 sec

Policy Researcher Offers Private Tours of Nation’s Capital

A public policy researcher starts a Washington, DC tour guide business and overcomes the hurdle of competitive TripAdvisor reviews.
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What It's About

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

Business Model
Skills Required
Public Speaking & DC Knowledge
Profit Potential

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.


  • 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


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

Yours in the revolution,


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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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