Female Disruptors: Lindsay Paige Stein of The Roundtrip Collective On The Three Things You Need To Shake Up Your Industry

I think it’s important to be the industry disruptor, not the disrupted. In my opinion, every company, even if they are decades old, should be figuring out how to disrupt in some shape or form. It’s a positive thing when a company or start up brings something completely new to the table, creates more opportunities, and fills a need that makes the consumer’s life easier.

As a part of our series about strong women leaders who are shaking things up in their industry, I had the pleasure of interviewing Lindsay Paige Stein.

Lindsay is a young travel entrepreneur and Founder of The Roundtrip Collective, the first-ever program designed to help students to turn their wanderlust into their dream jobs. Lindsay has diverse background within all facets of the industry, from managing PR for travel companies, writing about her travels for top publications, running influencer campaigns, to landing paid partnerships for her own blog. Her mission is to take her experiences and mold the travel industry’s future generation.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

I’ve always been drawn to traveling the world. Studying abroad in Prague during college is really what lit the fire in me to pursue a career path in the travel industry. In college, I launched my own foodie travel blog before “influencers” were a thing, and my audience grew pretty quickly as I chronicled my adventures across the globe. I was landing partnerships and making money online before I even graduated. I graduated with a mass communications degree, focusing all of my internships in public relations and social media, but my blog actually set me apart from my competitors in such a niche industry.

After my college graduation, I moved to Tel Aviv, Israel by myself to work for a food tour company called Delicious Israel, managing their social media and PR efforts. My dad had passed away six months prior from ALS (Lou Gehrig’s disease) and my life was just beginning. I knew I needed to reset my mind and do something completely out of my comfort zone if I wanted to continue to pursue my passions, stay on track, and become the independent woman I always dreamt of being. Moving away and traveling for the summer opened so many opportunities for me. During that time, I was also applying to jobs in New York City in preparation for coming back to the states and landed an interview for a travel PR job. The morning after landing back home from Israel, I went into the city for the interview, got the offer, and the rest is history. I’ve now been working in the travel industry and getting paid to wander the world.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

I’m filling whitespace in the travel industry by launching a travel career program and community that hasn’t been done before. Some people called me “crazy” for starting a travel company in the middle of the pandemic, but there is a need for it, and I knew it was now or never. The business idea was born during quarantine when one of my travel videos went viral on TikTok and I started getting flooded with messages from college students asking about what I do, how they can work towards their dream travel jobs, and tips on how to get started. That’s when it clicked, and I knew I had to create this to tap into the Gen-Z market who are interested in learning more about career options in the industry.

The Roundtrip Collective is the first-ever program helping students turn their wanderlust into their dream jobs through online courses, mentoring, connecting with travel pros, travel/remote job listings, and much more. The community has increased 3x over already just one month since launch and I’m getting new sign-ups and dozens of DM’s every day, so I know we’re onto something.

I was in their exact shoes and would have loved a mentor who has been in the industry for years and has the connections. I realized there are no real resources like this out there, so my mission with The Roundtrip Collective is to mold the travel industry’s future generation and create a community of ambitious students at a time when we all crave community and connection.

I’m leaning into the rarity of my diverse experience within all facets of the industry, from managing PR for hotels, writing about my travels for top publications, running influencer campaigns for travel brands, to landing paid partnerships for my own blog. Now is the time for me to help students get ready to make their first foray into the industry strategically with all the tools they need in their back pocket to stand out in a competitive landscape, to prepare for when the industry revives.

Knowing that I am helping the younger generation fulfill their dreams like I did and seeing some of their success already in such a short period of launching the program gives me a true purpose.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

I think the funniest mistake I made was that I thought my initial email database (of 200+ students to start) would convert into 200 immediate sales. Now looking back, I learned I was being too naïve and know not to be let down when an expectation doesn’t go your way. Sales is a process of gaining trust and credibility, but with consistency, they will start rolling in!

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

Before launching this business, I invested in a business mentor and I owe so much of my success to her (shoutout to Dulce Toscano!). It was scary to invest in a mentor for the first time, but I knew I couldn’t do this alone if I wanted to do it right. She taught me how to create, launch, and sell my online travel career course within a month. She pushed me when I needed to stay focused and connected me with other female entrepreneurs who were all in the same boat as me, which kept me inspired and held accountable.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

I think it’s important to be the industry disruptor, not the disrupted. In my opinion, every company, even if they are decades old, should be figuring out how to disrupt in some shape or form. It’s a positive thing when a company or start-up brings something completely new to the table, creates more opportunities, and fills a need that makes the consumer’s life easier. In terms of disrupting an industry being ‘not so positive’, I’d say on the flip side if it does end up taking over it can affect the jobs and livelihoods of the employees who may work at companies affected by this disruptor. Like when Netflix first came out with streaming services that was a positive for consumers who can watch shows or movies from the comforts of their homes, but it ended up taking tons of companies out of business, like Blockbuster.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

“Take messy action over perfect inaction”: I repeat this to myself all the time when I get overwhelmed and don’t know where to begin. My business coach Dulce told me this when we first started working together, and it helped me tremendously. Far too often, when I’m dreaming up an idea, I contemplate it for days or weeks, determining how I can go about executing it perfectly. When I heard these words of advice, I started taking action immediately with small first steps. It’s important to simply start.

“Mental vacations are just as important as physical ones”: This was especially relevant advice for me, because I’m always on-the-go and never really learned how to “turn it off” with all of the side hustles and my full-time career. After hearing this advice, I now set aside at least one day a week to shut off social media and have a day for myself (even if that means binging Netflix all day!). It’s essential for my mental health and creativity to reset my mind.

“Don’t go where the path may lead, go instead where there is no path and leave a trail”: You don’t always have to take the road most traveled, you have the power to decide a new and exciting route, to explore all that the world has to offer and to lead the way for others. This was important for me and kept me inspired when creating The Roundtrip Collective. As an entrepreneur, there were times I felt imposter syndrome or questioned certain aspects, but this advice kept my mindset in check that my goal is to pave a path forward for the future generation and there is no wrong because it hasn’t been done. before.

We are sure you aren’t done. How are you going to shake things up next?

This is only the beginning for me! I’m a dreamer, so every day consists of me coming up with new initiatives and ideas for the future of The Roundtrip Collective. I can’t give too much away, but up next will likely be a new course and educational retreats for travel-loving students. My first priority is giving all my attention to our members and growing our community, but we have a lot of exciting things in the works.

In your opinion, what are the biggest challenges faced by ‘women disruptors’ that aren’t typically faced by their male counterparts?

Being taken seriously. Most of the time, women starting something completely new or industry-disrupting are looked over and have to work 10x harder to gain support in comparison to men starting a business. For example, people will often refer to female’s newest venture that’s unique as a “passion project” when in reality it’s actually a legit business that’s changing the game.

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

Rick Steves gave a Ted Talk called “The Value of Travel” back in 2011, and it has resonated with me ever since. I found his personal stories and outlook on travel very moving. He gave examples on how travel can change us and it made me want to inspire others to experience this empowerment and follow their passions of seeing different parts of the world like I am. He also talked about the power of connection and diversity, and that’s what I hope to create with my community.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Be passionate about your life. Learn to live without the fear of failing. Take a chance, you just might surprise yourself.” I love this quote because it embodies how I aim to live my life. Since I was younger, I’ve always chased my dreams and have been a go-getter to live a life that I’m excited to wake up to. From taking the risk of traveling to another country by myself after college to starting a travel company during a pandemic, I follow my gut and take risks because I don’t want to look back and regret not taking the chance.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

I would absolutely love to somehow help young women who have gone through hardships or are underprivileged experience travel. Traveling forces you to challenge yourself in ways you’ve never even imagined. It helps women gain confidence and is one of the most empowering experiences a woman can have, so bringing it to others who are not able to would be a dream come true.

How can our readers follow you online?

You can follow me on Instagram at @theroundtripcollective and @lindsaypaigestein. If you’re a foodie, check out my blog at @nomnomblog.

This was very inspiring. Thank you so much for joining us!