Steve Milo is the founder and CEO of VTrips, a growing and innovative vacation rental management and lodging reservation platform which leverages a proprietary technology system to maximize occupancy, revenue growth and profitability. Steve Milo is considered an industry thought leader regarding the evolution of the highly fragmented Vacation Rental lodging industry to a transactional driven medium and is a key note speaker on the subject at conferences in North America and Europe.

In the following interview Steve shares some of his insights into entrepreneurship

When did you first discover your entrepreneurial spirit and How is your entrepreneurial career developing so far?

I discovered my entrepreneurial spirit in college at the University of Virginia with a necessity to pay for my tuition and expenses. Rather than work at the cafeteria, I began placing ads in collectible publications and sold comic books out of my dorm room. Eventually, there was so much UPS traffic going back and forth from my dorm room that I was summoned to the Dean of Students and kicked out of my dorm room for running a commercial activity. I found a small office and hired a full time employee and created a thriving business that became Another Universe.

What has been the biggest success and biggest failure stories you went through?

My biggest success to date is evolving VTrips from a small regional property management company into a national technology enabled property management company. In terms of failure, I still believe Another Universe was ahead of its time as a content and ecommerce site in the mid 1990s aimed at the comic book, science fiction and fantasy collector market. We had such a front runner advantage with everything except for capital and access to capital as we were based in Virginia and not Silicon Valley. We sold the company to Fandom in 1998 which imploded within 24 months.

Why did you get into vacation rentals business? Tell us something about VTrips.

I got into the vacation rental business over 10 years ago as a hobby while I was still working at a large ecommerce site. I was fascinated with the opportunity of vacation rentals, and the lack of sophistication of local property managers in the area. I was in the right place at the right time, as cloud based technology was just emerging and we became an early customer of Escapia which was created by Chris Kemp who later went on to work as the CTO of Nasa. VTrips has evolved into a technology enabled platform which leverages software to maximize operational and revenue efficiency for vacation rental properties.

Are you thinking about going international with VTrips? If yes, which countries would you be focusing/targeting and why?

Although the opportunities are immense in the United States, eventually we will move to international. Our first country would be Canada just due to logistics. Because we are not venture backed, we are very thoughtful about the operational and logistic costs of moving international. Canada would be the ideal first step.

Looking back, what did you learn and what would you have done differently?

I regret not being far more aggressive with expansion during the recession. We began to expand through M&A during the recession but it was really focused on rolling up the North East Florida region. There was so much opportunity to expand into markets outside of our area.

In your opinion, what are the hurdles that keep people away from starting an entrepreneurial career? What advice would you give to the new entrepreneurs?

In general, people are scared about leaving a job at the same time as funding a new company. My advice would be to start a new company by moonlighting. It is possible by working nights and weekends to build a base company to a point where it is not as risky to move into it full time.

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Devathon has built software for companies backed by world’s leading investors like Betaworks, Greylock, Andreessen Horowitz, Accel, KPCB, Lightspeed and many more.


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