Lessons Learned from 15 Years in the Trenches

By: Sean Keener, an EO Portland member and Special to Overdrive

Three things I might change if I were launching a startup today

So 2013 is underway, my wife and I just brought twin girls home from the hospital, I turned 40 and my travel startup—BootsnAll—recently launched its most ambitious product ever. With all of this in mind, I’ve done a fair bit of reflecting. In the past 15 years, I have learned a lot about building a successful startup, and I thought it would be fun to share a few stories (and lessons learned) in the process. So, here are three things I might change if I were launching my business today:

1. Pick partners that you want to help grow, and vice versa: For a few years, we were the number-one partner in the world for Hostelworld.com, the world’s largest hostel-booking engine. In 2004, I stopped by their headquarters to talk about how we could improve the relationship. It was one of the more awkward visits that I remember having. At one point, we were talking about the hostel-booking business with the two co-founders. They were cold toward me, to say the least. I didn’t understand why at the time. Looking back, I wonder if they were afraid of us? Not afraid that we were going to take them over, but in a “How did only a few guys generate so much business?” sense.

I later discovered that they didn’t want to cultivate a partnership together. They simply wanted more market share, and we didn’t fit into their plans. They systematically made life difficult for us and other affiliates. But to their credit, they became the best hostel-oriented search engine optimizer out there.

Lesson learned: From now on, I ask myself the following questions when working with partners: Are they trying to build a win-win? Or are they at the table because they “have to be”? The more info I have up front, the better.

2. If someone wants something, learn their “why”: Around 2002, TripAdvisor.com was a startup, not the behemoth they are today. Co-founder Langley Steinart emailed us about sponsorship on our site. They ended up buying a site-wide link from us for US$1,500 a month. When we sold the link, we didn’t fully understand the reasons why TripAdvisor bought it in the first place (SEO link juice, it turns out). I can’t remember how long we kept that link up, but I do remember taking it off once I realized that a site-wide link to TripAdvisor was worth more to us than US$1,500 a month. TripAdvisor was smart (they’re still smart)— we were up-and-comers, and had a lot of Google love that we parsed out to them. I don’t regret doing it; I just learned a valuable lesson along the way.

Lesson learned: If someone wants something from you, learn that person’s “why.” You may be able to get a lot more out of the opportunity than you think.

3. Give without the expectation of getting: One of the coolest parts of my business is that when we’re traveling, we’re often gifted things from others along the way, without the expectation to give something in return. It might be a meal, a beer, a conversation or a place to crash for the night. Since we started BootsnAll, we’ve lived via the “give before you get” vibe. It works wonders. We did start “getting,” and we turned that into even more giving. We’ve continued to give away free hosting and web application development over the years to dozens of non-profits, burgeoning travel writers and groups of people we just wanted to help out.

Lesson learned: Don’t keep track of everything that you give with an expectation of getting something in return. Not everything in life is 50-50, and that’s just fine. It’s the experience that counts, and knowing that you’re making a difference in someone’s life.

Sean Keener is the founder of BootsnAll, a travel startup that connects people with adventures all around the world. Fun fact: Sean delivered 200+ newspapers on a bicycle for 2.5 years to keep rice and beans on the table as his company was getting started. Read 13 more of Sean’s lessons learned.

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