I’m Ross Rankin and I’m sort of the grey hair here at TripLingo. I’ve been in technology for twenty years and startups for twelve of them. I started a company in the dot com heyday and had a “successful exit,” though I’m not sure for who…
All Roads Lead to TripLingo
For a number of reasons, TripLingo has been simply amazing. But let me start from the beginning.
After a year of suffering at my previous job, I decided to quit. I wasn’t happy, they weren’t happy, and the longer things continued the worse these feelings became. Even though I was working for a startup, it didn’t necessarily feel like a startup. So I started looking for events to attend, and at some point I was referred to both Start Atlanta and Startup Riot. I couldn’t have imagined what lay in store, but I registered for both.
Flash-forward through a month of networking and job-hunting: Start Atlanta was here. I did pitch an idea, but it was soundly rejected. However, I did like the TripLingo idea but I wasn’t in love. I just didn’t know enough, and even though the second pitch cleared up some of the fog, I wasn’t quite sold.
When the 12 ideas were selected, I made my decision based on the idea that I thought had the most clear revenue model, and my journeys with TripLingo began. See our previous post on StartAtlanta, but flash forward again and: we won. Now what?
I’m the guy in the green shirt.
After the win, we all gathered together and asked the question. Do we go forward as a team? The resounding answer was yes. Was that the adrenaline? The beer? The fatigue?
From my experience that weekend, I knew that Jesse was serious. I was getting serious too. I just need to hash out some details. A day later we sat down and did just that and all of a sudden I was now working on TripLingo full time. Honestly, it felt a little like fate intervening.
Fasten Your Seatbelt, Ladies and Gentlemen
Two days later, the rest of the team minus two was on-board and working part-time. And by “part-time” I mean 8+ hours per day. It was exciting. We met at Startup Drinks that week and celebrated, still high on our progress thus far and anxiously anticipating what lay ahead. I filed the incorporation paperwork and with the flick of a pen we were a real company, almost overnight.
Jesse’s fortune cookie at a team lunch: “Take a trip with a friend.”
An evening after Startup Drinks we planned our attack for Startup Riot. We had one goal: winning. We spent hours strategizing how to wow, woo, and work the crowd to get the votes we need. And we needed to do it on next to no budget.
We planned a startup centric app, coordinated shirts, created an infographic, and figured out a giveaway. Oh yeah, we also needed the perfect pitch. Just like Start Atlanta we broke into smaller teams and started working. Jesse and I worked on the pitch and presentation, yet another team on the app, another team on the data, and another team on the graphics and message.
Over the next couple of night, days, and weekends, we all pulled together, a brand new team and worked. And worked and worked. Everything personal was on hold, it seemed that even eating and sleeping were optional. The amazing thing was how unified the team really was with so little history; again it felt like fate. Just a week ago we were strangers and now we were a well-oiled machine.
The well-oiled machine in action.
The last night before Startup Riot was a late one. (Actually, they were all late ones.) We were having issues with the app and the website; the stress was amazing. It felt like we had been working all this time but were going to lose it all right at the end. Jesse was going through the tenth version of the pitch for the 50th time. Vince and Pratik were knocking out the bugs. James and I got the site presentable.
I went to bed very late and couldn’t sleep. Did our last minute fixes work? Is anything going to blow up in front of everyone? Was this the beginning or the beginning of the end?
The morning of Startup Riot, I got there early enough that I parked in the first spot and waited for entry to the Tabernacle. Finally, we get in and start setting up. I had deployed the web site the night before and it was fine. I got an email that there were a few typos. No biggie. I logged into the server to start fixing them. Then, out of nowhere, I lose my connection and can’t log back in. Nothing would work. Really- nothing.
I was frantically working trying to figure out what was going wrong. It was ridiculous. I was messing with security keys, ssh, .profiles, you name it. No dice. Then the news strikes like lightening: we’re third to present, our website is a critical part of our presentation, and I now have just 30 minutes to get this fixed or else fail in front of everyone.
I bailed on our original cloud provider (AWS) and move to another (Heroku). The Internet is crawling and everything seems to take an eternity. The sign up, the provisioning, the credit card processing, the deploy, the test… 15 minutes before our pitch the site finally pops up, working.
Jesse is backstage and our only line of communication is via phone. I shoot him a text: all is fine, knock ‘em dead. I start my apologies to the rest of the team for all the snapping I did at them for the last hour. I only had time to run up the stairs and grab a spot right before Jesse got started.
The pitch went nearly perfect. The rest of the event was networking, elevator pitches, and watching competitors present. Finally, just around 4pm, the moment had come and the final vote was called. The suspense was physically painful. The only time I had doubt the whole day was in that last five minutes. The rest is now history; after not much adieu we were announced as the winners!
StartupRiot Winner’s Representatives up on Stage. Jesse on the left.
We headed to Cyprus Lounge for some celebratory drinks. Naturally, afterwards we took a team to trip to a Karaoke bar and sang our throats dry.
Amazing. All of it. The win at Start Atlanta, the way our team came together, the enormous team effort for Startup Riot, and then: the payoff. The Startup Riot win. Warp speed, all of it.
Team TripLingo (TTL) Post-Startup Riot Win in Our New Lucky Shirts
Now all we needed was to build a company, finish a product, raise some money, and make some sales. Again, all at warp speed. Bring it.