Jared Simon – HotelTonight

Hey, I’m Chris. I wrote this article and I’m also the founder and Editor of DailyTekk. Lets connect on Twitter, Instagram, Snapchat and YouTube. Check back daily!


Jared Simon is the Co-Founder and COO of HotelTonight which provides last-minute hotel deals, tonight.


Great relationships with hotels are our lifeblood, but are very difficult to build when they’re constantly getting bombarded from companies like ours. Conventional wisdom would say we needed to put our account managers out in the cities where their accounts are, but we knew by doing that, our account managers would look and act the same as everyone else. By going against the grain and hiring everyone here in our SF HQ, we were able to build a real and consistent culture and vibe that has differentiated us in a very crowded space.


With any marketplace, the challenge is lining up both the supply and demand so they’re both there on day one. We set ourselves an aggressive 10 week launch schedule, and then set out to acquire both groups. On the customer side, we built up a social media following based purely on the mystery of what it was we were going to offer, so on day one there was enough pent up interest that we actually made a few bookings. That inspired the supply side, and then we were off to the races.


It was actually never very difficult to convince customers and hotels that we had something valuable to offer. Early on, the biggest obstacle was investor skepticism that there was actually a market in same-day hotel bookings. Many investors weren’t in the demo and just didn’t get it. So we decided to bootstrap until we had launched and demonstrated significant traction. After that, raising money for expansion became significantly easier.


Although I loved the camaraderie I found working in larger companies, I got frustrated that what I thought were lots of great ideas I had would get stifled in the politics and endless budget cuts. They might have been crummy ideas, but they never even got trial run. I went this route to prove (if only to myself) that I’ve got something big to contribute to the world.


The key lesson I’ve learned from startup fundraising is that you’re very seldom in a position where everyone you talk to sees eye to eye with you on your vision. You’ve got to push through all the people who don’t “get it,” to find the one who does. Everything works better when you have that meeting of the minds. We’re fortunate to have found that dynamic with some of the best VCs in the world (Accel, Battery, First Round, USVP) and some amazing travel industry angels.


Head to the most beautiful trail I can find (there are plenty here in SF) and go for a long run with loud music in my headphones. Then a quick shower and I’m right back in the zone!


The perspective that comes from lots of near misses, combined with a little luck, is all that separates us from the “average Joe.”


As many successful entrepreneurs will tell you, immediately before this, I was a not-so successful entrepreneur :)


I wish I had taken been more willing to take the road less traveled much earlier in my career. I’m having the time of my life, and it’s a shame I had to go through a bunch of years of not having the time of my life before I started taking some risks and having more fun. But then again, maybe I needed that perspective to truly appreciate what I’ve got now!


Starting a new company the week after getting married was crazy. Kids, don’t try that at home. Luckily, I quickly discovered that I have the most patient wife on the planet. She’s also a big HT fan, which doesn’t hurt :)

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