June 1996 - the original BootsnAll Trip. Throwing ourselves into Life, BootsnAll.
July 1997 – On a hike in Yellowstone National Park, Sean & Chris come up with the original BootsnAll Code of Conduct.
December 1998 – Sean & Chris meet at the Bluebird Tavern in Chicago to discuss ‘BootsnAll’ as a community.
1999 – BootsnAll registered as a business and initial pages of the website are live on the interwebs. The Code of Conduct is one of them.
2000 – BootsnAll is the target of a buy-out offer from a San Francisco start-up at the end of the dot-com bubble. Sean & Chris decide delivering newspapers at 4am is a better way to fund the business.
2001 – Portland newspaper The Oregonian writes ‘Bootstrapping’ feature on the anti-dot-com, spending the entire day at the BootsnAll office, including delivering newspapers. With zero revenue, the impact of 9/11’s repercussions on the travel industry are minimal on the young company.
2002 – Co-founder Nick O’Neill moves to Bali, Indonesia to create the web’s first daily updated travel guide, Bali Blog.
2003 – BootsnAll has its first profitable month. The company moves from Eugene, OR to Portland, OR and launches its own consolidator airfare engine.
2004 – BootsnAll recognized as RTW travel expert/resource in National Geographic Traveler.
2005 – 30 BootsnAll members attempt to summit Mt Kilimanjaro on New Years Day.
2006 – Spending over a month in Germany, BootsnAll produces extensive coverage of the World Cup & subsequently launches TheOffside.com, the largest English language soccer blog network.
2006 - While on a trip to Great Britain, Sean sees everyone (100+ people) in an Internet cafe on Facebook. He contemplates and realizes that BootsnAll will not be able to thrive head to head with FBook and the growing Social Media companies.
2007 – Lonely Planet co-founder Tony Wheeler visits the Portland office & agrees to be interviewed in the basement ‘studio’.
2008 – BootsnAll’s 10 year anniversary party sees over 500 people in attendance.
2009 – Sean reconnects with independent travel with a 4 month trip.
2010 – BootsnAll launches the WhyGo writing program to develop partnerships with passionate travel writers to produce high quality websites about destinations or travel themes that are constantly evolving and growing over time.
Feb 2011 – BootsnAll sells the world’s largest English Language Soccer Blog Network (mentioned above) to SBNation.com
late 2011 – The WhyGo Writers Platform stops taking new applications, in an effort to focus on being the #1 company in the world for Indie/RTW Travelers. CEO Sean Keener said, “We can’t be #1 in online travel guide, and Indie/RTW Travel. We had to make a decision on where we can provide the most value for travelers”
February 2012 – Along with Vagabonding author, Rolf Potts, BootsnAll writes and releases the Indie Travel Manifesto - now located at https://www.bootsnall.com/manifesto
April 2012 – The web’s first comprehensive, 3rd party report on the State of Around the World Tickets is researched and produced 3x in 2012 by BootsnAll.
January 2013 – BootsnAll launched the world’s first 6+ stop instant pricing and online booking airfare engine, Indie. This effort was in large part a result of his outlook on media sites from seeing the rise of FBook and other social media in 2006
December 2013 – BootsnAll acquires AirTreks.
2013 through early 2020 - BootsnAll and AirTreks grow from about 10 colleagues to 50+. As the pandemic kicks off, and people stop traveling, the staff reduces to 7
March 2020 through 2025 - Media websites like BootsnAll are "out of favor" as a business model - travel bloggers and travel websites of old are not the place to be as social media continues it's ascent as the "attention grabber"
March 2026 Want to know more? Find out the whole BootsnAll story.