Founder Story: Interview with Alex Alioto, co-founder and Head of Growth at Whimstay

Welcome to another installment of our Founder Stories series, where we delve into insightful interviews with startup founders and entrepreneurs. In addition, we engage in discussions with executives who are at the forefront of shaping the future of technology and leaving a lasting impact on a global scale.

Today, we have the pleasure of talking with Alex Alioto co-founder and Head of Growth at Whimstay, a travel marketplace set to disrupt the vacation rental industry. As the Head of Sales, he’s successfully onboarded nearly 600 property managers, managing over 100,000 properties, including industry leaders like V-Trips, TurnKey, and Vacasa, the largest Property Management Company in the U.S.

In 2018, Alex co-founded Whimstay, identifying a substantial market opportunity. As a co-founder, he is instrumental in driving the company’s supply-side growth. Prior to his illustrious tech career, Alex graced the New York stage as an actor from 1999 to 2011, showcasing his diverse talents and adaptability. With that, let’s get into the interview.

Thank you, Alex, for joining us to delve into the world of Web3 domains.

Introduction

Can you share a bit about your background and what inspired you to start your own business?

I studied theatre at the University of Michigan and then spent 12 years as a theatre actor in New York and toured across the country. Though I loved it, I eventually moved back to SF and started anew at Yelp. Turns out, the qualities that made me a good actor, like empathy and listening, translated well into sales and leadership. After learning a ton at Yelp, and a stint in consulting for several tech startups, my co-founders approached me with the idea for Whimstay, which was exactly the challenge my soul was yearning for.

What were you doing before you started your startup, and how did your past experiences contribute to your entrepreneurial journey?

Being an actor taught me resilience and how to ride the emotional rollercoaster – invaluable in startups. My time at Yelp honed my business acumen, particularly in developing a robust sales methodology. These experiences were fundamental to my current venture.

Inception and Motivation

What was the initial idea or problem that led to the creation of your startup?

Ben, one of my co-founders, was struggling with filling vacancies for his vacation rental properties. The only strategy seemed to be discounting expiring inventory and hoping for the best. We realized that every industry except ours had a way to deal with expiring inventory. We knew there was a market fit and the timing was perfect.

Can you describe the moment when you decided to pursue your startup idea, and what motivated you to take that leap?

I instantly said yes when my cofounders proposed the idea. I was seeking an endeavor that matched the high-risk, high-reward nature of acting. The idea of a ‘Hotel Tonight’ for vacation rentals instantly clicked, and I was ready to dive in.

Challenges

What were some of the major challenges you faced in the early days of your startup?

Looking back, our naivety was probably a blessing. We knew nothing about the industry but had a great idea and a lot of smartness on our side. That early ignorance allowed us to take the necessary leaps without fear, guided by the philosophy that “there is no ground.”

How did you overcome setbacks and challenges, and what did you learn from those experiences?

The biggest takeaway from facing setbacks is to keep going. If you have a great idea, market fit, timing, and a committed team, there’s no reason to ever stop. Perseverance is key, despite the challenges. Keep going.

Key Milestones

What are the key milestones that stand out in your startup journey so far?

Milestones like reaching 25,000, then 50,000, and up to 150,000 property listings on our platform were significant for me. The first time we hit one million bookings in a single month was another exciting achievement.

Can you share a moment or accomplishment that made you particularly proud?

Proudest Moment: Gradually gaining recognition within the industry has been a source of pride. Building something successful and meaningful, especially coming from a non-business background, is incredibly fulfilling.

Lessons Learned

What are some valuable lessons you’ve learned as a founder that you wish you knew when you started?

Starting a company is the hardest thing I’ve ever done. It requires resilience, equanimity, and a healthy appetite for risk. It’s about allowing life to unfold naturally and finding purpose in that process. It’s about trusting your intuition – it’s the same intuition that got you where you are.

Is there anything you would do differently if you could go back to the beginning?

I wouldn’t change anything. Every step has shaped our journey. Everything has happened the way it was supposed to happen.

Team Building and Leadership

How did you go about building your team, and what qualities do you look for in team members?

We look for team members who are smart, hungry, and willing to work tirelessly. Whimstay cannot be a paycheck, it needs to be a ticket – it’s a pathway to future opportunities and growth. Our team’s passion and commitment are what make us successful. This team is in it to win it, and I absolutely adore them.

Can you share insights into your leadership style and how it has evolved over time?

While I’ve always been a positive, supportive leader, I’ve learned the importance of balancing this with direct accountability. Hiring the right people is crucial – people who want to be held accountable and get better as a result. But the accountability has to be consistent. That’s always been my challenge. It’s a growth process for me – but it’s gotten better for sure.

Growth Strategies

What strategies did you employ to grow your startup, both in terms of customer acquisition and team expansion?

We let every person who owned their department – own their department. We foster a culture of trust and autonomy. For me, my focus has been on a strong, acquisition-focused sales strategy.

How do you approach innovation and staying competitive in your industry?

Staying ahead of the curve is our mantra. I listen to every podcast. I subscribe to everything I can. We’re constantly eager to learn and engage in team discussions to innovate and improve our services.

Community and Networking

How important has networking and community engagement been for your startup?

Networking has been pivotal in building trust and forming key partnerships. We’re also actively involved in advocating for short-term rentals, tackling industry challenges head-on.

Are there specific communities or networks that have played a significant role in your journey?

Our software and Property Manager partners have been instrumental to our success. They’re the backbone of our product and service.

Adaptability and Pivots

Have there been instances where you needed to pivot or adapt your business model? How did you navigate those changes?

We’ve been fortunate that our straightforward value proposition has remained solid, negating the need for major pivots.

How do you stay adaptable in the face of evolving market conditions? In a weird way, evolving market conditions have helped us.

Evolving market conditions have surprisingly worked in our favor. Our service provides value for travelers and offers a vital distribution channel for property managers.

Advice for Aspiring Founders

What advice would you give to aspiring entrepreneurs who are just starting their journey?

If you’ve got the right market fit and timing, and a great team, don’t stop. The journey will be a rollercoaster, but perseverance is key. Just keep pushing forward.

Are there resources or books that you found particularly helpful on your entrepreneurial path?

My resources lean more spiritual than business, with authors like Wayne Liquorman and Nisargadatta influencing me. Being a creative in business, understanding oneself is paramount for me.

Current Day and Future Plans

Can you provide an overview of where your startup is today and any exciting developments on the horizon?

We’re not messing around with our 2024 roadmap. Without spilling too much, expect significant advancements in features, functionalities, UX, partnerships, and audience growth. Just as mentioned, we have big plans on the horizon. Stay tuned.

More about Alex Alioto:

Alex embarked on his sales career a decade ago, transitioning from a 12-year tenure as a celebrated New York stage actor. His journey in sales began at Yelp in 2010, where he quickly ascended from Account Executive to Sales Manager within a year, thanks to his exceptional performance. At Yelp, he led teams that consistently outperformed in revenue generation and target achievement. Alex played a crucial role in developing Yelp’s National Franchise Sales organization and later spearheaded the Yelp Reservations SaaS product. Post-Yelp, he leveraged his expertise to consult for tech startups like SwoopMe and Hitch-Ride, enhancing their sales operations. In 2018, Alex co-founded Whimstay, a travel marketplace set to disrupt the vacation rental industry. As the Head of Sales, he’s successfully onboarded nearly 600 property managers, managing over 100,000 properties, including industry leaders like V-Trips, TurnKey, and Vacasa, the largest Property Management Company in the U.S.

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