Redeam Turns the Interview Tables on Tourpreneur’s Shane Whaley

How he made the leap from top digital travel sales executive to popular podcast show host and content creator

If you’re in the tours and activities sector of travel, it’s hard not to know of Shane Whaley. In fact, if you worked in the online hotel industry in the early 2000’s you probably know Shane. For 16 years, Shane was a powerhouse business development and sales leader, holding important executive roles at name-brand travel companies like, Priceline, and GetYourGuide. But in 2018 he deliberately chose to give up that fast-paced demanding life for the kind of work-life balance he knew he needed to honor. But what to do next? After careful consideration, he concluded that it was time to reinvent.

tourpreneur podcast

Shane’s new business, Tourpreneur, is a podcast series and daily email briefing focused on the real-life stories of tour operators and the kind of information that matters to them. Since Shane is the producer and host of the Tourpreneur series, he spends a fair bit of his time talking to and interviewing many people every week. Redeam decided to turn the tables on Shane and interview him to capture the story of his career pivot, which – it turns out — isn’t all that different from the subjects he normally interviews!

Here is Shane’s story.

Redeam: Shane, how did you go from leading sales efforts for online travel sites to hosting and producing a podcast show and daily news update? These seem like very different professions.

Shane Whaley: Prior to my career pivot, I had spent the past few years creating and hosting a podcast show as a hobby. I love spy novels, and I decided it would be fun to try to do a podcast in which I interviewed spy authors, fans, and intelligence experts. Little did I know that my pet project, Spybrary, would take off so well!

In the meantime, I felt I had unfinished business in the tours and activities industry. I’d always admired and been fascinated by tour owners. I loved talking to them but could never spend enough quality time with them when I was a busy executive. I had a burning curiosity to learn what made them tick – I wanted to hear their stories. I didn’t want to be the guru – I just wanted to learn from the actual owners. Since I had already cut my teeth learning how to do podcasting, when I thought of the kind of things I might want to do next professionally, a podcast show about tour operators made perfect sense. No one was doing that, there seemed to be a need, and it wasn’t a capital-intensive business to start. Tourpreneur officially launched a year ago in January 2019 – I launched the podcast and the Daily Brief at the same time.

Redeam: What were the reactions from people you shared your idea with?

Shane: Of course, I had my supporters, but there were also naysayers from the start. Some people said I was crazy; that no one would listen to my shows; that there wasn’t any demand for this topic. I had to bullet-proof my mind and put on my figurative noise-cancelling headphones as well as my actual ones. I am quite proud that in only a year’s time and with zero advertising, I’ve had tremendous organic growth of Tourpreneur. We have had 25,000+ podcast downloads with listeners in 110 countries, a 54% open rate on the Daily Brief — which astounds me — and over 1,000 subscribers. On social media, we have fantastic community engagement. One thing I’ve learned through this podcast is that tour operators – especially smaller ones of large metro areas — are yearning to talk to someone about their industry. There are few places they can go to learn how to run their businesses better.

Redeam:  Even though your idea might not have been capital-intensive to start, starting any business involves risk. How is your risk tolerance, and how did you move past any of your doubts?

Shane: I actually used to be a super risk-conservative person when I worked for large corporations, but now I’m on the other end of the spectrum! It’s almost counter-intuitive because I’m living off my savings right now, so you’d think I’d be holding back, but I’m not. I want to build raving fans, and to do that, I need to be all in. Running my own business is scary, but I like this kind of scary. I also love controlling my own time. I have actually been approached by big companies that want me to go to work for them, but I’ve turned them all down because I’m loving what I’m doing right now! I realize, though, I still need to be smart – I am building a business and not a hobby, after all – and this year I will be starting to take on sponsors.

Redeam: Apart from already knowing how to produce a podcast, did you know how to do everything else that running this business requires? What new skills did you need to acquire and how did you go about doing so?

Shane: I definitely had to learn a few things, the most important of which was how to become a good interviewer. I started watching more news programs to see how they interviewed guests and how they framed questions to get people talking. I had to learn how to ask hard questions (I still struggle asking financial impact questions, for instance) – I want my shows to be a conversation, not an interrogation. I had to learn how to prep for my interviews, especially because I’m always interviewing tour operators with different kinds of tours. I found that listening became even more important.

Then there was the whole running of this kind of content business that I had to learn:  Email list management, production flow, podcast editing and publishing, WordPress website creation and management, how to use social media and market a business through it — like running a Facebook Group or using Instagram. 

Redeam: What have been some of your other big obstacles or challenges?

Shane: The toughest thing for me is managing my time. There’s just so much to do. I’ve become very good at setting up weekly goals with a schedule. I’m actually more organized now than when I worked for big corporations! I have learned to outsource some of the work I don’t have to do so I can focus on my bread and butter. Another lesson I’ve learned is that what I worried about as an employee is completely different than what I worry about now as an entrepreneur. I used to worry about my staff and our deals and making our numbers; now I go to bed at night sometimes worrying if I’m wasting my time and my money.

Redeam: What has your emotional spectrum been like during this reinvention journey? How did you cope?

Shane: A rollercoaster! I have suffered from imposter syndrome, because I’m actually a shy, introverted person. Who am I? I’ve never run a tour business! I don’t want Tourpreneur to be the Shane Whaley Show. I want the guest to be the expert.

Some days I feel like I should just throw it all in and get a job, but most days I find the energy I need from all the heartfelt emails and messages I get from the operators themselves who tell me how much my show is helping them. I also keep in perspective that my objective in creating this business was to have a certain quality of life, not grow big and exit fast. In that regard, I’m a lot like the tour operators I interview.

I feel like it helps to journal. We should all journal. As an entrepreneur, it’s important to capture your highs because you’re always firefighting. Also, every morning I visualize the path for my Tourpreneur success…but I also visualize the pain to come – which I’m sure there’ll be – because that allows me to anticipate and overcome it. This is a tough industry – I’m not going to sugarcoat that in my mind.

I’m also trying to be healthier.

Redeam: While you’ve been on this journey, how did support from others matter and where did you find it?

Shane: Support has been a HUGE factor. For instance, early on I got an email from Rod Cuthbert, the former Chairman and CEO of Viator. I didn’t know him at the time, but he wrote that he loved what I was doing. Since then he has become something of a mentor to me. I also found support from many people at my former employer, GetYourGuide, and other OTAs and rez-tech companies. Douglas Quinby, Co-Founder and CEO of Arival, was another person who has helped me tremendously. A huge turning point for me was when Checkfront sponsored my Tourpreneur booth at Arival Orlando this year. That wasn’t an inexpensive endeavor for them, and it was a way for me to meet tour operators, many of whom personally thanked me for what I’m doing. It made me confident in committing another whole year of my life to this business.

Redeam: What’s been the most rewarding part of creating Tourpreneur?

Shane: My general happiness. I’m much happier because I’m loving what I’m doing, and I’m respected for it. The feeling of creating and leading a company is empowering. I also really get to know and help people. I get to teach tourpreneurship through the key things I’m gleaning. To be a tour operator doesn’t require any particular certification or advanced degree, so sharing the tips my guests tell me could help a business and make a difference between them just surviving or truly thriving.

Redeam: So, to wrap this all up, do you think that a career change like yours is for everyone? Can anyone reinvent?

Shane: Yes, if you have passion for the thing you’re reinventing into and if you’re willing to have failures along the way. But don’t do this on a whim or if you don’t have some money in reserves – if this is the case, start your new thing as a side hustle to see if it really works for you.

Redeam: Thank you so much for sharing your wisdom so candidly, Shane! We wish you much luck in 2020 and the years ahead!