Why Grit Wins: How Determination Unlocks Success in Vacation Rentals

The Hustle and Heart of the Short-Term Rental Grind: Why Grit is Your Secret Weapon

The short-term rental industry is booming, but don’t be fooled by the curated TikTok posts about becoming an “Airbnb Millionaire” easily in a couple of months. Building a successful business in this space is a marathon, not a sprint and I hate to give it to you straight…you need to grind! As Angela Duckworth, author of the influential book Grit: The Power of Passion and Perseverance, argues, it’s not just raw talent that separates the thriving founders from the rest. It’s grit, that powerful blend of passion and perseverance that fuels the drive to overcome inevitable setbacks and navigate the ever-changing landscape of the industry.

The Early Days: Embracing the Grind 

Jessica Livingston knows a thing or two about grit, determination and success. She was the co-founder of Y Combinator, the startup incubator that has launched 5000+ companies and created 90 $1B or greater companies.  Jessica famously emphasizes “determination” as the most important trait for successful founders:

“If I had to say, the most important trait of the most successful founders… is determination. That is by far the most important quality. More than intelligence! More than previous success… Determination is the most important thing.”

In the short-term rental world, this determination translates to embracing the grind of the early days. I can personally attest to this. When I first started Vantage, we had zero properties – zippy – but high goals. Every week, I’d wake up at 5 am on Mondays and drive the 3 hours down to Ocean City. I would then spend the entire week in a cold, dark condo by myself, as I felt I had to be in the market to build this company into something I knew it could be. The drive home was every Friday night. I did this for five years straight. 260 weeks. Away from my wife and two young daughters. I missed many birthdays, anniversaries, and school events. It sucked, and I’m not proud of it in the sense of wearing it as a badge of honor. It was simply what I had to do to get through the startup grind. I know many other people in this industry that have made those sacrifices as well. 

But as David Friedberg, entrepreneur, angel investor and co-host of the popular “All-In” Podcast, says, 

“There is no giving up. You do what it takes. Persistence is one of the biggest predictors of success.” 

Those early days were a test of that persistence. There were moments of doubt, but the unwavering belief in the potential of Vantage kept me going.

Building Your Resilience Muscle: The West Point Advantage

As Duckworth highlights in Grit, challenges are inevitable. Regulations change, unexpected repairs arise, and economic downturns can disrupt even the most meticulously planned strategies. Here’s where grit becomes your armor. It’s the unwavering belief in the potential of your short-term rental business that pushes you to adapt, learn from mistakes, and find innovative solutions.

Grit over Talent

Just like The Military Academy at West Point admissions, where top test scores and physical fitness aren’t the sole indicators of success, the same applies to the short-term rental industry. Duckworth’s research on West Point cadets found that grit, a powerful blend of passion and perseverance, was a more significant predictor of thriving in that challenging environment, even more-so than GPA, SAT scores or even the highly refined West Point admission scoring system. 

The Power of Perseverance in Action

Similar to West Point cadets overcoming the grueling “Beast Barracks” training, grit empowers short-term rental entrepreneurs to navigate obstacles. This unwavering determination allows you to adapt to changing regulations, solve unexpected repair issues, and find creative solutions during economic downturns.

The Power of Community

The journey of a short-term rental entrepreneur doesn’t have to be a solo act. Surrounding yourself with a community of fellow founders, mentors, and industry experts can be a game-changer. Join one of the many Masterminds that are out there like the one that Tristan Webb facilitates through STR Directors. Sharing your struggles and triumphs with those who understand the unique challenges of the space can provide invaluable support and fuel your motivation. 

Looking Ahead: The Rewards of Perseverance

The road to success in the short-term rental industry is paved with grit and determination. But for those with the will to see it through, the rewards are immense. This was certainly true for Vintory. In the early days, just like with Vantage, it was a constant hustle. I would wake up between 4-5 am every day to do all of my “work.” Then, from 9 to 6, it was a whirlwind of meetings with partners and sales calls with prospects. This became so ingrained in my routine that even today, years later, I wake up at the same time out of pure muscle memory.

Those early days were intense. It was just me and one or two other team members. In that first year, I made it a point to meet with every single new partner onsite in their market. That’s 34 on-site meetings in just one year (on top of conferences and running the normal “day-to-day” operations).  While going on-site with every new partner may seem excessive now, the value of those meetings was immeasurable. As Brian Chesky, co-founder of Airbnb, says, “In the early days, do things that don’t scale.” That’s exactly what I did by prioritizing those in-person meetings. They allowed me to truly understand the pain points of our partners in their own environment. This understanding proved invaluable and became the foundation of the Vintory inventory growth system. It’s also so refreshing to have many of those partners still on our platform and the relationships and friendships that have grown over the years. 

The Final Climb: The View from the Top is Worth It

The road to success in the short-term rental industry is undeniably challenging. But for those who embrace the grind, cultivate grit, and leverage the power of community, the rewards are substantial. You don’t have to be the smartest or most talented person in the room; you just have to want it more. It’s about getting back up when you get knocked down, understanding that failure is not a permanent condition. The hustle might be real, but the sense of accomplishment and the positive impact you create make it all worthwhile. You’ll build a business that not only provides financial security and professional fulfillment but also contributes to the ever-evolving travel and hospitality landscape.

Short-Term Vacation Rentals: A Community of Grinders

I’ve been fortunate to meet many short-term rental managers over the years, and one thing that always strikes me is their sheer determination. We’ve all been there – the early mornings, the late nights, the constant problem-solving to ensure our guests have a five-star experience. This industry is filled with countless stories like mine, founders who have poured their hearts and souls into building something special. It’s a community of grinders, people who never give up and are always looking for ways to innovate and improve. The grind never stops; it just changes. Early on, it’s about sales and relationship management, then operations, and later, scaling and sustaining growth. We’re all still involved and passionate about day-to-day success, wearing multiple hats, but over time, we layer in top talent to support the mission. That’s the kind of spirit that fuels success in this dynamic industry.