For many entrepreneurs the path to success involves one or more rounds of funding. Seed money, bootstrapping, and plowing profits back into the company simply isn't enough to achieve a critical mass of capital and resources.

So if you're a tech company, you should naturally turn to Silicon Valley investors, right?

Not so fast.

Jen O'Neal is the CEO of Tripping.com, a company she founded with COO Jeff Manheimer that is currently the world's largest search engine for vacation rentals with over 10 million property listings (that's four to five times more listings than Airbnb.) Tripping.com was the first meta-search site for vacation rentals, aggregating properties from sites like HomeAway, VRBO, TripAdvisor, Booking.com and others, letting users search, compare and book in one place. (Think KAYAK for vacation rentals.)

They've raised funding three times, including a just-announced Series C round of $35 million led by Princeville Global.

But the road to funding -- and generating over $500 million in gross bookings this year, a 600% increase over last year -- was anything but smooth.

I love origin stories. Tell me yours.

Originally we launched with a social travel model but when Airbnb caught fire, we noticed the vacation rental market was incredibly fragmented. The top four sites had between 18 and 20% of the market. These huge sites were a small percentage of the market and there were all these other sites scattered around the world.

To sum it up, we saw an extremely fragmented supply base. So we stepped back and thought, "Okay, in a super fragmented market, what model makes the best sense? We quickly decided to focus on meta search, rolling all that supply into a single platform and letting users compare prices.

So we launched in 2011, which turned out to be about three years too early for the market. Those years were painful, but then the market caught up in a huge way. We did our Series A in 2014, over the next year we grew about 3,000%, did our Series B... and now we've closed our Series C.

And now we're definitely the market leader. We have over 10 million properties on the platform, we get millions of visitors, and we're doing half a billion dollars in bookings with only 32 employees.

How do you generate revenue?

Sending qualified bookings to our partners. If we book a property listed on, say, HomeAway, they share a portion of the revenue with us. Our job isn't to compete with our partners. Our job is to send them good bookings.

But it took us awhile to get to this point. Early on we operated like a lead generation service. People couldn't book online: they would email the property owner who might email them back... bookings took an average of nine days... and if you decided to book the property you would show up and pay the property owner in person. That's how everything was run because bookings couldn't be paid online. So we operated in a PPC model, and that was tough.

When the technology caught up and made online bookings possible we were the first to allow direct booking.

We have younger employees who think it's funny that properties couldn't be booked online. They have no idea how recent that technology is.

Sometimes being first is not a great thing.

True, but for us it's definitely turned out to be. No one had data feeds, so we worked really hard to figure out a way to get all the rental data from all the different sites onto our platform. Our engineers worked with the sites to find a method and create an infrastructure that allowed us to build the feeds.

Now any property company that wants to work with us has to write to our API. And they're happy to do it because they know our infrastructure works. Building that took a long time... but it's why we now don't have a lot of competition.

When you decided to raise funding, instead of just finding someone who would write a check you took a different approach.

First, you shouldn't look to raise capital unless you have a strong strategic reason to raise. Start with your biggest pressing need -- and then determine which investors are best suited to fill that need.

So with our Series A, we had very little money for marketing and weren't in a great position to raise. We had heard about Recruit Holdings, the company that had acquired Indeed and are experts in SEO, and we talked to them about leading the round. As part of the deal they provided a dedicated SEO team to help us. That was incredibly important to our growth.

Our Series B was in 2015 when the entire industry started shifting to onsite bookings. We knew the industry would rapidly make the change to online booking, and hedge funds have an interesting view of the market, so what could we learn from them? We knew they could help us identify trends and spot opportunities before others do. Steadfast Venture Capital led our Series B and helped us navigate the waters at a time when the industry was doing a 180.

Now we're doing a huge amount of volume and are in a strong position and ready to freely expand internationally. The strategic need we now have is to find people who can open networks to us and who can help us extend into Europe and Asia.

So the actual capital is only a part of what you look for.

Bottom line, we're fortunate to have great investors and it's partly because we're surgical about who we work with.

There are lots of sources of capital. Many of the entrepreneurs I meet in Silicon Valley think they can only raise from the Valley. There are amazing investors outside of the area. I always encourage people, especially if you're growing a global business, to look outside the Valley, too.

You're in a great position now, but it wasn't always that way. How did you hang in there during the lean years?

It was definitely not easy to hang in there. We didn't get paid for years. Every dime we had we gave to our team.

Our philosophy has always been to skate where the puck will be. For the first three years we couldn't even see the puck, though. We weren't even holding a hockey stick. But you have to believe that it's all going to come together.

Every time we got discouraged we would look at the data and that kept us going. Logically, we thought we could see what was going to happen. We knew it would happen. We just had to hold on.

But it was definitely hard. I couldn't pay my rent one month and had to call my parents to help me. It's crazy looking back on that... because it wasn't that long ago.

And here we are today, with our latest round of $35 million and altogether we've raised $50 million. That shows investors believe in our vision. Within the decade vacation rentals as a category will be worth about $285 billion, and accommodations will be over 1 trillion for the first time.

That's why we can attract capital. When you believe, and the data supports your belief, you just have to stick with it.

Lots of companies are too early and don't stick with it, though.

I worked in tech for a long time before starting Tripping.com. I've experienced being too early. I was the fifth employee StubHub -- were way too early for the market. That gave me confidence that you have to stick with it. I also helped build viagogo. That helped me a lot.

And our market is bigger than theirs.

What's do you see ahead? And on the flip side, what keeps you up at night?

We want to be a multi-billion dollar company, and our investors can help us get there. For example, one of the reasons we work with Princeville Global is that their partners have worked with companies like Alibaba and played key roles in their growth.

As for what keeps me up at night... One thing is maintaining our great team. We're really big on "team," and we want our people to feel good and motivated and happy with what we're building.

The other is moving fast enough to seize the opportunities in front of us. We're by far the global leader, and I want us to stay there.

Big decisions can be paralyzing. Our philosophy is to be data-driven, use data to point us in the right direction... and then not be afraid to make decisions. You have to pull the trigger, monitor, and if a decision doesn't work, move on to something that does work.

That philosophy paid off for us early on. We found this huge gaping hole in the market that no one was filling. We couldn't believe no one else saw it. So we jumped in. It turns out they didn't see it, and we were right to jump in.

Never be afraid to make big decisions -- that's the only way you'll have a chance to accomplish big things.

Published on: Dec 16, 2016
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