Today we’d like to introduce you to Evan Haskell
Hi Evan, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
I was born and raised in Los Angeles, and from an early age, I was a very socially outgoing person. I didn’t care much for school but loved the social aspect and being the class clown—I’ve always enjoyed making people laugh. In sixth grade, my parents pushed me through the application process for private school, and somehow, I got into Campbell Hall in North Hollywood. The transition from a public LAUSD school to a private institution with a challenging curriculum wasn’t easy—I got suspended during my first week for ditching class because I thought that was a normal things to do. But in the end, I made it through—barely—finishing with a 2.4 GPA.
Applying to 20 universities with a 2.4 GPA was a very “humbling” experience, to say the least, for me at 17, with my whole adult life ahead of me. Watching my friends get into all the “big schools” they wanted, while I was left with only one acceptance out of 20, hit me hard—it’s like the universities didn’t want me or something (joke). I don’t blame them. The running joke is that I didn’t even get into the University of Arizona, where my grandfather was a donor. That was a pretty dark experience for me personally—it’s where I realized that what you put into life is what you’ll get out of it.
Ultimately, I chose San Jose State, but from day one, I knew I had a decision to make: commit fully to my academics and transfer, or pursue baseball. That year, I dedicated myself to my studies, earned straight A’s, and successfully transferred to the University of Southern California’s Marshall School of Business after my first year. Honestly, I felt like I beat the system a little bit—I had this epic high school experience, basically failed my classes and had fun doing it, went to a state school for a year, got my life together, and transferred to a top 20 school in the nation. Not bad. I definitely learned something about finding your place in life. There isn’t just one way to get where you want to go—there are many routes. Hard work, dedication, good relationships, and working smart are the keys to reaching any destination.
While at USC, I kept busy with a job at First Republic Bank (RIP), balancing work, school, and a healthy lifestyle. It was great—I got to earn money riding my bike to class, and I spent all of it traveling and taking weekend trips to Vegas with my friends. By the time I graduated, it was clear to me that I wanted to work for myself and travel while doing it. In 2012, I saw an opportunity in the short-term rental space because I had a feeling Airbnb was going to be the future of travel. I began leasing apartments in downtown LA, furnishing them on a shoestring budget, and listing them on Airbnb. Despite the basic setup, people were still paying rates comparable to the nearby Marriott, which told me I was onto something. I saw an opportunity to build a scalable business—that lightbulb really went off in my head.
Recognizing that business travelers would be the perfect demographic to build my brand around, I relocated to Silicon Valley and partnered with multi-family landlords who had vacant units. Over the next decade, I built what became the largest short-term rental brand in Silicon Valley, primarily catering to business travelers from companies like Facebook, Google, and Tesla, as well as professional athletes and celebrities. At its peak, the company had over 200 units in its portfolio across more than 25 markets, generating $8 million annually.It was an incredible journey, full of challenges, constant problem-solving, and growth. Reading The 4-Hour Workweek was a game-changer for me; I learned to streamline my workload, and during the peak and final three years of Urban Flat, I only worked about five hours a week, thanks to an amazing on-ground team. I always say I built the business to be a well-oiled machine—and the best businesses are! Never settle for decent; always strive to be the best in anything you do, in business and life, and you’ll be on the path to success.
When the pandemic hit, housing business travelers and pro athletes in Silicon Valley became unsustainable—in fact, it was going to kill my business. I decided it was time for a change, so after fighting to survive, I sold the company I had spent my 20s building. It wasn’t an easy decision, but I knew it was the right one. You always know in your heart when it’s time to make a change, whether in life or business, but sometimes it’s hard to pull the trigger and do it. In this case, the world decided for me, and ultimately, the universe always decides for you if you let it. The key is recognizing how you feel and making the decision before life makes it for you—that is strength, that is discipline, and that is maturity. It’s what separates the most successful from the rest. Freedom of choice should never be taken for granted—use it wisely.
This shift led to the launch of Synchronest with my business partner, Coburn Sheppick, in early 2022. We saw a gap in the short-term rental market, where most hosts—whether managing one home or a hundred—weren’t using the systems, tools, and strategies I had refined over the years. Synchronest started as an idea, but with a hypothesis, we got to work, landed our first client, and have been growing steadily ever since (we’re not the fastest-growing performance agency in the industry!). Today, Synchronest is a performance agency for short-term rental hosts and property managers, dedicated to helping them earn more, free up time, and scale their businesses seamlessly. Our services include managing clients’ revenue, optimizing listings, building websites, and serving as strategic advisors—we now have clients in over 70 markets worldwide. It’s a truly fulfilling business because we’re able to make a meaningful impact on our clients’ lives. I love what we’re doing because, in an industry full of “gurus,” we’re focused on building a high-quality brand that brings together high-quality people who can lean on each other to build better short-term rental businesses, ultimately enabling everyone to lead better lives.
Outside of work, I love spending time with my family, being outside, feeling the sun on my face, meditating, watching the Lakers or Dodgers (that’s the only TV I watch), and eating good food (what else do you do in LA?). I have two brothers, and my parents are still in LA, so I get to hang with the family a lot. I’m also in the process of building three houses in Santa Teresa, Costa Rica—a place I fell in love with during my travel days with Urban Flat. I currently live in Silver Lake with my amazing girlfriend and future wife, Dakota.
Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
My journey has been anything but smooth, and honestly, I’m not sure a completely smooth road even exists. I’ve always been torn between pursuing the opportunities in front of me—chasing the “American Dream” by pouring everything into building a business—and my desire for a simpler, healthier life by the beach in a more affordable place like Costa Rica. But I chose the path of entrepreneurship, and that path can be incredibly lonely, painful, and difficult. The good news is, I can change courses at anytime – I feel like when you think this way, you can’t lose. I’m happy with everything, and I’m happy with “nothing”, because I already have everything.
In the early days of starting my first business, Urban Flat, I litteraly pushed myself to the brink. I was working so hard that my relationships began to suffer, my health started to decline, and I wasn’t happy with how I was treating myself or others. That was a wake-up call. I realized I needed to focus on creating a healthier, more balanced lifestyle and use my time more wisely. That shift in mindset became a turning point for both my business and personal growth.
Meditation became a life-changing practice for me, and it still has a profound impact on my personal life today—you can probably catch me on the patio at Soho Malibu with my eyes closed most days; it’s just part of my routine now. Shoutout to my friends Jordan Rosenheck and Mel Nahas—they’re the ones who introduced me to meditation, and it helped me reshape my perspective and prioritize my well-being. Even now, building Synchronest is full of challenges—I’m constantly solving problems, putting out fires, and facing the struggles life inevitably throws at you. Recently, I overcame a lawsuit from a large corporation, which was frightening and a harsh reminder of corporate greed. It was a tough situation, but it reinforced my belief that no matter what life throws at you, it’s all about how you handle it.
At 35, I’ve come to accept that life isn’t a linear path—nobody said it would be, and it’s not easy (especially in this modern day and age). It’s full of ups and downs, but as long as you’re moving in the right direction (forward), learning from your experiences, and maintaining the right mindset, you can find happiness, fulfillment, and live a life full of immense love. If you’re in a rut, prioritize your physical health—get up and go for a run. This will drive better mental health, and from there, everything else starts to click.
As you know, we’re big fans of Synchronest. For our readers who might not be as familiar what can you tell them about the brand?
Synchronest was born from my 10-year journey of trial and error in the short-term rental industry, where I failed countless times so that other hosts wouldn’t have to. I saw an opportunity to help others avoid the same mistakes and instead implement the systems, strategies, and protocols I had to figure out on my own as a first mover in the space. Synchronest has carved out a new category we call a “performance agency”—we partner with property managers and self-managing hosts to help them unlock the full potential of their short-term rental businesses.
When a client partners with us, we start with a stage called “Elevate.” It’s all about positioning their business for success by optimizing every critical component—from branding and PMS software to listing presentation, marketing strategies, pricing, websites, digital guides, and more. This process typically takes about 30-45 days, and we have a specialized team of over 20 consultants who bring expertise in various fields, including pricing, operations, web development, and creative. We’re in the people business—we don’t build software; we just know which ones are the best, partner with those companies, and help our clients put everything together at a high level. This is the key to our success because it’s much easier said than done, and we’ve mastered that craft. There are levels to the game—and our clients perform at the top.
After the Elevate phase, we focus on ensuring long-term success for our clients. We manage their dynamic pricing using specialized software and our proprietary AI models, provide ongoing advisory support, and help them continue to grow. We’ve built a strong community of hosts across 70+ regions worldwide, and we’re expanding quickly. The key to our success lies in our ability to deliver high-quality work that translates into a fast ROI, leaving our clients not only satisfied but excited about the future of their businesses. We’re also focused on building a community of good people, bringing them together, and, eventually, we’ll host live events and have some fun things to look forward to—all dedicated to our clients.
Can you tell us more about what you were like growing up?
As a child, I was always outside, always curious, and always building something. I just loved being active and exploring the world around me. It’s funny how life has a way of connecting the dots because I ended up in the hospitality industry, but there were signs early on. I vividly remember sitting in the back of my parents’ car, flipping through the “For Sale” section of the LA Times, admiring beautiful properties and dreaming about owning them someday.
That fascination with properties stuck with me. Fast forward to my adult life, and it’s almost as if that early passion was guiding me toward the path I was meant to be on. It feels like I was called to this industry, where I get to work with beautiful spaces and help others enjoy them just as much as I did while dreaming as a kid. A lot of people ask me how I knew this was the industry I’m supposed to be in, and, funny enough, I think it chose me. It’s important for people to connect with themselves, think about their childhood, what brings them joy, and go there—the money will follow. Start with passion.
Growing up in Los Angeles played a huge role in shaping who I am today. The city’s diversity exposed me to so many different cultures, backgrounds, and perspectives, which allowed me to see the world through a unique lens. I grew up in the hills near Mulholland and Beverly Glen, and while LA is known for its city life, I was always an outdoors person at heart. I played sports like baseball and basketball, spent summers at Cheviot Hills Park, and was fortunate to have a grandmother with a beautiful beach house in Carlsbad, where I’d go at least six times a year. Those experiences really fed my curiosity and love for exploring.
As the oldest of three brothers, with one five years younger and the other nine years younger, I always felt a strong responsibility to be a leader and a role model. I saw it as my duty to learn through trial and error and then share those lessons with them—a role I still embrace to this day. I’ve always been a social person, and high school was a time I genuinely enjoyed. If I could press a button and go back, I would, simply because I loved those years so much.
Attending USC was an amazing experience, although sometimes I do wonder what it would’ve been like to go away for college, as I’ve spent almost my entire life in LA. Watching my brothers head off to the University of Arizona and Indiana University for that “real” college experience, while I was doing laundry at my parents’ house, sometimes made me wish I had ventured out of my comfort zone. Plus, USC isn’t located in the nicest part of town. However, being at USC gave me something far more valuable than just a degree—it connected me with a fantastic community of friends and forged lifelong relationships that make up the famous Trojan network.
When I was a student, people always said the Trojan network was powerful, that it was something I’d benefit from for life. At the time, it was hard to fully understand what they meant, but now, more than a decade after graduating in 2011, I see it clearly. The connections I made aren’t just valuable from a business standpoint; they’re genuinely great friendships that have lasted over the years, and I’m grateful to be part of such a strong and supportive community.
Contact Info:
- Website: https://www.synchronest.com
- Instagram: synchronest_hospitality
- Facebook: https://www.facebook.com/synchronest
