Author: Sean Keener

16 Things I Might Change If I Was Launching a Travel Startup Today

2013 is here, my wife and I just brought twin girls home from the hospital, my 40th birthday is right around the corner, and BootsnAll is preparing for the launch of the biggest product in our 15-year history. With this in mind, I’ve done a fair bit of reflecting.

Over these 15 years, I have learned an incredible amount, and with all the change in the world and my life, I thought it would be fun to share a few stories and the resulting lessons from one and a half decades at a travel startup (I once heard somewhere that if a company is under $15 million a year in revenue, it is still a startup. BootsnAll is below that level and has been since we started in late 1998, so in my mind it’s safe to say we are still a startup).

It’s been awesome connecting personally with thousands of travelers over the years. I’ve been told many times “how we helped” in getting people on the road and helped change their lives. Been told many times “that we are bad, we suck, and we’ll never make it.” Through it all, over 100 million folks have been to our website(s) over the past 15 years.

So here are the 16 things I might change if I was launching a travel startup today:

#1. Go for it and ask for forgiveness later.

travel lessons

Is it ok to ‘Spam’ Lonely Planet?

In the first few months of our existence, we would spam participate in the Thorn Tree forums, and in our signature tag, we would leave a “Sign-up for BootsnAll” message. This was early 1999, and spam was a lot different than it is today. We got to the point where we’d download all the threads using Excel, export all the email addresses, do duplicate matching to make sure we did not email someone twice, and then Nick, Chris, and I (co-founders of BootsnAll) would break up the list and send a personal message to Thorn Tree participants one at a time. Wow – that was cumbersome, but it did provide a lot of sign-ups. And we found out people actually liked us!

This didn’t last long. After we did it a few times, a few people wrote back to us and told us it was “bad.” So we stopped, and I remembered feeling down at the time.

We then proceeded to start a Thorn Tree Newsletter that highlighted the top 10 threads of the week on the Thorn Tree. Lonely Planet sent us a cease & desist letter for the newsletter. I wrote them back and told them that we were linking to their best content! They didn’t get it at the time. We added a TM to the words “Lonely Planet,” and they let us be.

Lesson learned: Go for it and ask for forgiveness later (Mark Zuckerberg is the modern day bloke who popularized this one).

Alternative lesson: Don’t spam. It’s short term thinking that does not build meaningful relationships.

#2: Go to the bank to deposit more often than you withdraw

We all know this. Each one of us needs to spend less than we take in. This idea can be cheated for a period of time, but it always comes back to bite someone in the arse if not taken seriously.

Chris and I made sure that we didn’t withdraw more than we spent by doing a newspaper delivery route on our bicycles. We woke up at 3:45 am, 7 days a week, 365 days per year to deliver about 250 newspapers in Eugene Oregon for 2.5 years (as BootsnAll was getting started) The $800 to $1000 per month that we earned is what fed us and put a roof over our head so we could work on BootsnAll the rest of the time.

This idea can be cheated for a period of time, but it always comes back to bite someone in the arse if not taken seriously.

Some days were awesome. I remember riding my bicycle back to the office most mornings energized. On those mornings when the sun was just starting to come up and the sky was clear, it felt like it was worth it.

This being Oregon, there were rainy, cold days as well. Stepping over and around homeless folks to deliver papers as a 28-year-old after the dot com bubble burst was a humbling experience. Chris and I would get to the office many days at 6:15 am, cold and looking like a wet rat. It was a lot harder on those days.

My dad told me once to make sure you deposit more than you withdraw. With this in mind, we have paid all of our bills over the years, even during the lean newspaper delivery years. No matter how little, or how much we made, we always made sure our expenses were lower than our revenue. It’s funny to think that, in a country like the USA (and many other western countries) that runs a 1 trillion dollar debt every year, that we citizens think the US can run this way forever. One day, who knows when, it won’t end well for us Americans. Just like every other person, company, or country that doesn’t follow this rule.

It provides me a bit of peace – that I know I can live on $500/month and still be happy. As a bloke with a family now, I wouldn’t want to do it, but I could do it if I had to, and I could be happy. I know it. I will just aim to continue tweaking expenses as income goes up or down in life. It’s all possible, and a lot less stress.

Lesson learned: Spend less than you take in

Alternative lesson: This lesson can be cheated, but not forever

#3. You don’t always have to scale.

We personally emailed about 100,000 people, one at a time, on purpose.

BootsnAll version 1 had 6 pages of content. All were pages asking folks to become a member. Over the first 10 years, we intensely cultivated our community. All day, every day was the credo. We set-up a user database that allowed our members to contact each other via filters of where they were, where they were going, and what type of traveler they saw themselves as. We even had a “couchsurfing” application before Couchsurfing (sidenote: After we shut down our database, co-founder of Couchsurfing Casey emailed me a few times asking for promotion of his Couchsurfing site. Look what he and his pals ended up building!).

The answering of every single application built a bunch of relationships that remain to this day and gave us a chance to connect with each new member.

From day 1, we set-up a membership application that allowed us to screen every application by hand. We’ve had about 100,000 people apply to be a BootsnAll member over the years. We read 50 to 100 applications per day, and we wrote back to all that were accepted and not accepted with a personal touch. To this day, each application is still screened manually as a line of defense against spam. Lots of folks in the dot com boom, and web 2.0 boom told us, “You don’t scale.”

The answering of every single application built a bunch of relationships that remain to this day and gave us a chance to connect with each new member. Folks that became lifelong friends and travel industry friends like like Jen Leo, Rolf Potts and Sherry Ott.

Lesson Learned: Taking the time to connect with folks is a time consuming process, but by putting ourselves out there, we made a lot of friends that we still have to this day.

Alternative Lesson: Something that “doesn’t scale” is just fine.

#4. Just because something is easy, doesn’t mean that you should do it.

Travel lessons

Sometime in early 2002, we learned how easy it was to get a #1 rank on Google. I remember changing some title tags, the link from the homepage of BootsnAll to a page, and when Google updated their alogrithm, we were number one on that term. For a group of guys just getting started, this was a find! We immediately built content for what we wanted to be number one on. The first few things were Around the World Travel related. This helped us start to generate some revenue.

Over the next few years we were optimizing for hotels, cheap airfare to New York, and other stuff that I couldn’t care less about. We could get number one or first page on many of them. We made a lot of money this way for a few years. A #1 ranking could generate up to $500 per day in revenue, and we had a lot of them. This SEO stuff financed things like BaliBlog and WorldCupBlog/theOffside, and many other projects over the years.

I remembered doing all of this, but not being fully comfortable with it, but couldn’t put my finger on exactly why. Looking back, I just didn’t care about Cheap Flights to New York and related searches. I also knew because my heart was not into this part of BootsnAll, that it would not last forever.

Lesson learned: See the doors that open along the way, and be open to going through doors that you didn’t know existed

Alternative lesson: Just because something is easy, doesn’t mean that I should do it.

#5. Pick partners that you want to help grow, and vice versa.

For a few years, we were the #1 partner in the world for Hostelworld (the worlds largest hostel booking engine). In 2004 or 5, I stopped in Dublin (Hostelworld Headquarters) to visit them while I was on a RTW trip. I was eager to talk to them about “how can we improve this relationship?” (How naive I was).

It was one of the more awkward visits that I remember having. At one point, we were at a pub talking about the hostel booking business with the Affiliate Director and the two co-founders. The two co-founders were cold towards me. I didn’t get it at the time. But today, I wonder if perhaps 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 soon found out via their actions that they didn’t want to cultivate a partnership together. They wanted more market share, and we didn’t fit into their plans. They systematically made life difficult for us and other affiliates. But to Hostelworld’s credit, they became the best hostel oriented search engine optimizer out there.

They might take offense to that statement, but they were GREAT at what they set out to do. Almost the whole first page of google belonged to them. They bought, they set-up other domains, and they dominated the SERP’s hard core. All this domination led to HostelWorld being acquired for a reported $458 Million by private equity in 2009.

I congratulate them for this and never felt bad towards them. They built a beautiful business and systematically got more and more market share. I am not patronizing when I say, “Well done.” They killed it. BootsnAll was just a little bump/partner in the road along the way for them.

Lesson learned: Ask the question to yourself, “Are your partners actually trying to build a win-win? Or are they at the table because they ‘have to be?'”

Alternative Lesson: Pick partners that you want to help grow, and vice versa. It comes back to core values and having the same goals!

#6. If someone wants something – learn their “why”

Around 2002, TripAdvisor was a startup, not the behemoth they are today. Co-founder Langley Steinart emailed us about sponsorship. They ended up buying a site-wide link from us for $1500 US month. That was good revenue for us!

When we sold the link (which we thought of as a sponsorship), we didn’t fully understand the reasons TripAdvisor bought it (SEO link juice). I can’t remember how long we kept that link/sponsorship up on BootsnAll. I do remember taking it off once I realized that a site-wide link to TripAdvisor was worth more than $1500 a month to us.

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, just learned a lesson along the way.

Lesson learned: If someone wants something from you, learn that persons why.

Alternative lesson: Just do it and learn from it along the way!

#7. You don’t have to be one of the “cool kids” to succeed

We started during the first dot-com boom. Cool kids were everywhere, and we were not one of them!

The cool kids on the block were sites like,, and In travel there were a bunch of startups that were “cool.” They had money, wore cool clothes, and were “redefining” business. I can’t even remember the names of them anymore.

After 9/11, Web 2.0 came, along with the tech blog mafia – Techcrunch, Mashable, Engadget, and others. They created more of the cool kids concept. I remember hearing a lot of folks and bloggers say, “I gotta get listed on Techcrunch.”

They had money, wore cool clothes, and were “redefining” business.

In travel, there was/is the Phocuswright Conference. I think most would agree, that Phocuswright is a big influencer in defining who is cool in travel. As the world and travel changes via technology, it can be a bit much at times. They promote the new thing every year to draw speakers and conference goers. It’s quite a show. (Sorta like a U2 concert)

After leaving those conferences and being exposed to some of these ideas and companies, I often asked myself, “How can I do all of this, so we can be cool too?!”

After the 2010 version of Phocuswright and reading several years of the Tech Blogs, I was hanging with travel writer Tim Leffel, and he shared the same “ugh” feeling I had. Much of “the cool stuff” we tried to do then is now dead. Just like most of the cool kids. For every AirBnB and Instagram, there are countless pieces of roadkill.

Because of this mentality and “peer pressure,” there were times where I felt like BootsnAll was “missing out” on some trend. Many of our 100s of websites were an attempt at being one of the cool kids. Here is a snapshot of the graveyard (,,,,

Lesson learned: If you are chasing trends, you are too late.

Alternative lesson: Don’t chase trends; do what you think is best and can add value

#8. No one owns a community. You might just have access to them.

The term “community” didn’t have the cache that Social Media does today, but that is squarely where BootsnAll started. We had a member database, message boards, member meet-ups, and other fun things like stay at the “BootsnAll Hostel” (a floor in our house) for free. We cultivated a community of about 50,000 folks with about 1 million unique visitors per month by 2006.

Web 2.0 was well underway at this point. Myspace was the thing then, Twitter was just getting started, and Facebook still a year or so away from mainstream adoption. I saw the writing on the wall when I was in London in 2008. I was in an internet cafe, and Facebook was on EVERYONE’S screen. This was the end of us thinking that we owned a community. In fact, I don’t think anyone truly does own a community.

I started saying in 2008 that community is “everywhere” – it’s not owned. Twitter, Facebook, in the comments of popular travel blogs – BootsnAll, Lonely Planet, TripAdvisor, Travellerspoint, and Travelfish are just a few of places that community exists in the travel sphere.

A good example of this is Instagram and its recent change in privacy policy. Their actions said, “We own you and your shit”. But of course they don’t. Even Facebook with its 1 billion profiles doesn’t own the community, and odds are, in my opinion, they will eventually lose it (unless they move to a more cultivative philosophy). Sidenote: Check out as an alternative to Facebook who understands that the user owns their data and has built a framework where this can be sustainable.

Lesson learned: No one owns a community. You just have access to them, and the relationship needs to be cultivated and will change over time.

Alternative Lesson: Community is everywhere. In your home, your neighborhood, online, in comments on “blogs,” twitter, facebook and many other places.

#9. Life is short! Do stuff with people that you like to spend time with.

BootsnAll beginnings

BootsnAll was started because of friends. The friendship between Chris and I and the “friends” we met on the road. It was an obvious fit for us to go into business together. When we did in 1999, many folks told us that this was dangerous. We could lose our friendship. It was “dangerous” and “risky.” But I would do it again.

The reality of going into business with Chris and Nick was that there were some hard times. But would it have been different with folks who were not friends? I know I enjoyed spending time with Chris, Nick, and Anthony (our first colleague, also known as Ant), so why not work together?

Becoming financially stable made it better for sure. It’s easier to “agree” when things are going well. Not any different from any other relationship in life. But you also have to accept that there are risks involved.

Make sure that the folks you do choose to be with in business, life, travel, etc – are ALIGNED from a core value perspective.

One particular tough time was when Nick left the company in late 2007. Nick had been with us from the beginning. We set him up in Bali, and he had been blogging for 5 years there. He was burnt out, so it was a good vibes decision on his part to leave, and I understood.

But we did have the business side of things to take care of, and part of leaving meant Nick selling his shares back to the company. Nick wanted to maximize the value, we wanted to minimize it – the natural tug and pull of buying and selling a closely held company was a challenge. We eventually came to a reluctant agreement. I can’t say I am proud of how I dealt with it at the time. To Nick’s credit, he moved on quickly and has remained an awesome friend and confidant over the years.

Lesson learned: Do stuff with people that you like to spend time with. Life is short!

Alternative Lesson: Make sure that the folks you do choose to be with in business, life, travel, etc – are ALIGNED from a core value perspective. This makes all the difference and has been huge for Chris, Nick, and I. I still feel tremendous love and respect towards Chris and Nick after all these years.

#10. Learn to forgive yourself.

I’ve had my fair share of saying goodbyes over the years. Some were initiated by me, some by others. Colleagues quitting, me firing them. Friends I met on the road and saying goodbye to them. From my single days, saying goodbye to old lovers. Sometimes it was me, sometimes it was them.

Saying goodbye to someone, whether it be a colleague, friend on the road, or lover, is difficult. Each time I did it, I hated doing it. Each time it was done to me, I hated it, despite there always being justification.

Being said “no” to or quit on, or dumped – I’ve been on both sides, many times over the past 15 years – is hard. But at this point, I’m at peace with it when it happens. If someone wants to quit, dump me, or leave, I perceive it as a good thing. If I make that decision, it’s also good.

I want to be with people that “want to” be with me. I fully respect each person’s path in life. Sometimes they cross and are aligned, and sometimes the path diverges. Both ways are cool.

The hardest part of saying goodbye was firing people. I felt bad, and I still do in the bottom of my heart, as one of my core values in life is to build bridges with others. Firing, from the other person’s perspective, is rarely viewed as a building bridge sort of action. Of course, staying with someone, just because I always have, is not a good reason either.

Lesson learned: Don’t beat yourself up for making tough decisions. Forgive yourself.

Alternative lesson: Try hard to build bridges and find common ground. The recently departed Stephen Covey had a big impact on me and BootsnAll these past 15 years. Read his classic book.

#11. Take conventional paths, expect conventional results.


Chris, Nick, Anthony, and I all took a risk in 1999-2002 to give BootsnAll a go. It was not the conventional path. Many friends, family, and others laughed at us. “What is this website you are working on 12 hours a day, 6 days a week? All 4 of you live in a shithole, brewing your own beer, and barely making ends meet” was the mantra of many (not all) folks that knew us.

We all could have easily gotten a “regular” job. I was 25, Chris, 24, Ant 21, and Nick 35. We could have fallen into line – do what we were “supposed” to do. The original BootsnAll trip changed my view of the world. I knew I couldn’t “go back” and just do what most of my neighborhood friends from Chicago did. I had to try. I traveled around the world and saw so many different folks doing, living, failing, succeeding, loving, dying – just like me – except in a different place.

One idea that stuck with me over the years is No Regrets. For example, when we hired someone to build a BootsnAll member database in 1999, we paid for it with money we couldn’t spare. Before making the decision to go for it, I asked myself, “Would I regret not trying to build the database on my death bed?” The answer was yes. I would totally regret not trying.

The original BootsnAll trip changed my view of the world. I knew I couldn’t ‘go back’ and just do what most of my neighborhood friends from Chicago did. I had to try.

Tomorrow, BootsnAll is launching something that many folks told us could not be done. The amount of money, time, and man-love-hours put into it is beyond what I could have imagined even a few years ago. We are moving forward with the No Regrets philosophy. Let’s give it a damn good go. It’s been an awesome ride so far, and I look forward to even more rides!

Lesson learned: Take conventional paths, expect conventional results

Alternative lesson:Take alternative paths, and expect different results

#12. Being the first to market something doesn’t mean you’re the best, or that you will succeed.

Co-founder Nick O’Neill and I decided to open up a “branch” of BootsnAll in Bali shortly after the bombings in 2002. As far as I can tell, we produced the world’s first daily updated online travel guide ever. We had a lot of fun building it, going there, trying to work with folks in and outside of Bali. Nick built a very popular blog that had a ravenous reader base. It was not sustainable from a financial perspective; however, and the fact that we were first didn’t mean much. Looking back, I am not sure the world, or Bali, needed a daily updated guide.

We were perhaps the first to do this, and we stuck with it for 5 years. Looking back, I could have done a lot of things to monetize the site better, but I just didn’t have the time with BootsnAll website empire expanding so rapidly at this time.

Lesson learned: It’s a ton of fun to follow your dreams

Alternative lesson: Being first brings great memories and friendship and fulfills the above lesson of No Regrets, but not necessarily long term success.

#13. Give without expectation of getting

One of the coolest parts of Indie Travel is often times, as a traveler, we are gifted things from others along the way, without any expectation from the giver as to getting something in return. It might be a meal, a beer, a conversation, or a place to crash for the evening. During my travels, I was gifted many things along the way from unexpected sources.

When we started BootsnAll, and many times throughout the years, we have lived via this vibe. Our Message Boards with it’s 400,000 posts, answering individual applications, and helping people plan trips – we had no idea if it would ever get anything in return. I remember talking with Chris and Nick after 2 years and saying, “Even if BootsnAll doesn’t turn into anything more, it’s been totally worth it.”

The “Give Before your Get” theory started working. We did start “getting”. We turned that into even more giving. We have 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. Just 2 year ago, we were the Platinum Sponsors of Passports with a Purpose.

I am not perfect or trying to portray myself as Mother Teresa. There are times that I drive a hard bargain and continue to do so. But it still feels good to give without the expectation of getting. In fact, the #1 thing that drives me today is that folks get out there and do some Indie Travel via BootsnAll or otherwise. This is the best way to learn and get an education.

This lesson is closely related to VC Brad Feld, Give Before You Get post that he recently shared, and I see most folks that I enjoying spending time with, practicing this “lesson.”

Lesson learned: Don’t measure and keep track of everything that you give with an expectation of getting something back.

Alternative lesson: Not everything in life is 50-50, and that’s just fine.

#14. Let go of the side of the river

Even though Nick is not with us at BootsnAll anymore, his mantras and way of life still guide us in many ways. A story that Nick would tell, multiple times, but each time like it was the first, was being ok with letting go of the side of the river mentality.

 Be free, let go, and see what happens and where it takes you.

If you want to experience a river, you need to get away from the shore. See and be open to where the river takes you versus trying to control every aspect of life. Of course, we always related it back to travel. Be free, let go, and see what happens and where it takes you.

Lesson learned: Letting go to the side of the river WILL open up possibilities that you never knew existed (A great way to let go of the side of the river is to go on an Indie Trip for an extended period of time – you can do it!).

#15. Focus on Something – What can we be #1 in the world at?

I talked about BootsnAll’s lack of focus at my keynote speech at TBEX 2011 Vancouver (titled From Zero to a Million). Over the past 15 years, it seems like we have tried everything. BootsnAll bought about 1000+ domain names and developed a few hundred websites for ourselves in lots of different categories. Most of it was in the travel sector and was a learning experience, but looking back, many of them were a waste of resources.

Starting tomorrow, the culmination of over two years of soul searching and focus at BootsnAll will begin. We have come full circle. We created all sorts of random websites, but now we are coming back to our roots, back to what we love and believe in: Indie Travel.

Lesson learned: Long-term, it’s better to be the best at one thing versus just another commodity in a crowded field

Alternative Lesson: Trying lots of different things exposed us to lots of victories and defeats, which we learned from. If we focused too much during these first 15 years of BootsnAll, we may not have the opportunities that we have today.

#16. Are you playing not to lose or are you playing to win?

Travel lessons

Verne Harnish shared that statement with me and my EO MIT classmates in June of 2012. And he paused. It was quiet in the room after he said it. We were all thinking. I teared up because I knew that I was playing to win now, but I HAD played not to lose in the recent past.

The biggest playing not to lose lesson related to BootsnAll was after the financial crisis in 2008. Many of my decisions as CEO were made/controlled by fear. Fear of losing rankings, fear of losing employees, fear of revenue degradation (all three things happened anyway).

When I and the folks I am around are “playing to win,” I am in a positive mindset. I believe the financial crisis was a teaching mechanism for BootsnAll (and others) on not to let the news dictate your thinking.

Ask yourself this question and pause. “Are you playing to win, or playing not to lose?” Emotional? Feel anything?

With the playing to win mantra in mind,  we shared our 1st of its kind tool, Indie on January 8th, 2013. Indie is the only airfare engine in the world that can do instant pricing for 6+ leg trips with no rules, and online booking.

It’s built for independent, autonomous travel minded folks.

See what folks have to say about Indie.

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What lessons have business and travel taught you? Agree/disagree? I will be around to discuss below in the comments:

Photos: 427, Eole, paul bica