Ep. 32 — YouTube for Tour Operators. How Rob generates 90% of his bookings from YouTube.

DC tour operator builds his business by providing hacks on Youtuberators

In the competitive DC market, Rob attracts guests by providing hacks and tips to visitors. His YouTube audience drives approximately 90% of his bookings.

Rob Pitingolo – TripHacks DC

At A Glance

DC tour guide serves up hacks and tips via Youtube to fuel a thriving tour business.

Tour Style: Walking

Tour Niche: Our nation’s capital, Washington DC (District of Columbia), with a lot of facts and Jeopardy-style trivia to add an additional layer of fun

Booking Platform:

WordPress plugin ‘Team Booking‘ with Stripe payment integration. Bokun.

Website: WordPress

Tour Customization Level: High.

Rob offers standard public tours, which can be paid and joined per person but specializes in customizable private tours. Private tours are paid per tour (up to 10 people), not per person. The content and pace are personalized to the group’s interests and desired speed.

Special Skills:

Rob’s business model offers not just a tour and information about DC landmarks but actual trip hacks for his website visitors and tour guests.

The Vision

Rob has worked his professional office job in Washington DC for years. (Still does.) But he wanted something he could do as a side hustle for extra money.

For five years he worked as a tour guide for a large DC tour company, knowing all the time that he’d rather work for himself. In 2016, inspiration struck while wandering around Youtube.

The Trip Hacks DC Story with Rob Pitingolo and Tourpreneur Host Shane Whaley

Rob Pitingolo had some unique inspiration in 2016 to move from working part-time for another tour company to opening his own tour company.

It all started when he found a Youtuber making videos about an area he was planning to vacation. Commentators on the videos kept asking if the Youtuber gave tours. She did not.

“I thought, ‘Well hold on a second, I am a tour guide. And I can make videos and follow this concept.’ So that’s what I did… A few months later, I dusted off a video camera that I had in my house, and I just started making the videos about Washington, DC, and everything went from there.”

Rob Piringolo – Trip Hacks DC

Rob always presents himself as a tour guide but then concentrates on delivering useful hacks, tips, and advice for people looking to visit the DC area. And it works. Currently, Rob has over 13k Youtube subscribers.

YouTube for Tour Operators – Rob’s Secret Sauce Revealed.

  1. Rob’s Youtube videos are not promotional. They are informational. Each video concentrates on a hack or useful information about DC. The videos are not about his tours. They are about his city.
  2. Rob limits his call to action in his videos (i.e. selling people on a tour with him) to the very first 10-15 seconds and the last 10-15 seconds of his videos. The majority of each video focuses completely on serving people with good information.

Washington DC for under $20 – a great example of the content today’s tour operator is putting out on YouTube. Notice how he is not hammering us to ‘book his tour’.

What exactly does Rob advise other tour operators do to generate bookings from YouTube.

Rob’s top tips for tour operators who want to create videos for YouTube.

  1. Save your money. Making videos customers respond to does not require expensive equipment.
  2. Focus on the audio. A good microphone makes all the difference. Rob recommends Rode brand.
  3. Record inside whenever you can. This eliminates wind noise.
  4. Invest in a gimbal for smooth video.
  5. Use good editing software. Rob uses Sony Vegas (Vegas Creative).

But exactly how did Rob get his videos noticed? How did he grow an audience of over 13.1k?

To address these questions, Rob and Shane discuss how to…

  1. Be consistent
  2. Invest the time
  3. Be patient; it pays off
  4. Be binge-worthy
  5. Understand the Youtube search algorithm (spoiler alert: it’s not like Google’s.)
  6. Know what video type is going to convert for you. About his, Rob says…

ROB’S SUCCESS TIP: To know what will get viewers and likes, you must know what people are already wanting to know. What are they searching for? The data is out there. Find it. Use it. Build your videos around it.

How Tour Operators should operate in a competitive city.

Rob is in one of the most competitive markets, yet he’s ranked #9 on Tripadvisor out of 209 companies. What does he do about that?

This subtle yet crucial difference may be reducing the number of interested patrons. Ben recommends Olga make impactful changes to her website’s headline (the top, first large text on a website that a viewer sees).

“My philosophy when it comes to competition is that if there’s competition, it’s because there’s demand.” — Rob Pitingolo, Trip Hacks DC

Rob and Shane discuss:

  1. You don’t need to be new, just be the best
  2. Tripadvisor algorithms
  3. Google owns Youtube, what that means for tour operators
  4. How to make SEO improvements, including using Ahrefs
  5. Conduct your due diligence before engaging any SEO service

To help you accomplish this, you need someone to view your website with fresh eyes. To be frank, business owners are too close to their own operations to suss out potential issues and gut reactions. After all, you know exactly what you do and what you mean to convey. That makes it difficult to see how others might not “get” what you do.

Considering going full time and/or hiring help.

Rob still works his regular full-time job because he wanted to grow slowly. Shane encourages new tour operators to do the same. But in the meantime, if your business is growing well, you’ll likely need help.

Rob and Shane discuss:

  1. Using your network to find help
  2. Videos doubling as recruitment tools

Legal hurdles for tour operators and Bokun for tour operators.

Like most new tour operators, Rob had to get his website and get licensed. He tried to register with Tours By Locals but there were already too many DC tour guides listed. So he was forced to get an LLC, a tour license and insurance, all on his own.  

Rob and Shane also discuss Rob’s experience with Bokun (a booking platform) by Tripadvisor.

Parting Words of Wisdom from Rob Pitingolo of Trip Hacks DC.

“Get some experience in the industry as a tour guide. I started my business after having almost five years of my own tour guiding experience.

And it just saved me so many headaches that I know that I would have run into if I wasn’t already familiar with the industry.

Rob Pitingolo – Trip Hacks DC

Got questions for Rob? He is a member of our Tourpreneur Insiders Facebook Group. Come and join us and like-minded tour operators and tour professionals over at the group.


Listen in on valuable advice in this speed round as Shane asks Rob:

  1. What is a habit, trait or characteristic you believe contributes to your success?
  2. What is your biggest weakness?
  3. What is one question that you ask or look for during the interview process when hiring tour guides?
  4. What is your biggest challenge in your business or what keeps you awake at night?
  5. What is one book you recommend other tourpreneurs?
  6. What podcast do you recommend for other tourpreneurs?
  7. What is one thing you feel tour operators do not do well enough, or often enough?
  8. What is one piece of technology you have adopted that has had the biggest impact on your business? And why?

Links and Resources Mentioned on this Episode of Tourpreneur – a podcast for tour operators.

Links Mentioned in this Episode

Trip Hacks DC

Trip Hacks DC Podcast

Trip Hacks DC Youtube

Trip Hacks DC Instagram

Trip Hacks DC Facebook

Trip Hacks DC Twitter

Rode – audio microphones

Vegas Creative – video editing software

Adobe Creative Cloud – video editing software

Ahrefs – SEO tools to grow search traffic, research competitors and grow your niche

Team Booking – WordPress plugin for booking and calendar coordination 

Bokun – Tripadvisor’s tour booking platform

Tours By Locals – tour guide vetting and listing website

Side Hustle – book by Chris Guillebeau that Rob recommends

Side Hustle School – Rob’s appearance on Chris Guillebeau’s podcast, Episode 508

Spectacular Failures – podcast with Lauren Ober that Rob recommends