Jana Kleitsch, CEO of Wanderlust Society, writes about the other F word—failure.

In this Underwire exclusive, Jana Kleitsch, CEO of Wanderlust Society, writes about closing her company.

With her trademark humble intelligence and composure, Jana hits on the wrongs and rights of her three-year journey through the travel industry, including:

  • The importance of marketing and early lead generation
  • What not to do with a team of product geeks
  • Fundraising for introverts
  • Key insights to keep personal health in check

I’m writing on my failure and what went wrong. Britt wants me to be more raw, she thinks I’m not being honest enough because it hurts too much.

But for me the failure wasn’t one catastrophic sweep. It wasn’t one big misstep that doomed Wanderlust Society. It was death by a thousand little cuts, and not very many big breaks.

Last spring I read Phil Knight’s memoir, Shoe Dog, and one phrase stood out to me. “If you’re not growing, you’re dying.”

Wanderlust Society was not growing. We had no funnel. Instead of working on the funnel, we were working on features like search. Instead of seeing if our landing page resonated, we were adding a Chrome browser extension. And our marketing? Non-existent.

We had been dying for quite some time. I had hoped we could turn it around with some press… and that did give us a spike, but it wasn’t sustainable or repeatable without a PR budget, or marketing.

Venture Capitalists like to use the term “fail fast.” We were failing slowly. What does “fail fast” even mean? The quote seems ridiculous and venture capital-y.

We wanted to be “indie,” like Basecamp and Ruby on Rails. Between the two founders of those companies, Jason Fried and David Heinemeier Hansson (a.k.a. DHH), they have at least half a million Twitter followers. They weren’t building a product with people miraculously discovering them. They were publishing books, speaking on podcasts, and writing big ballsy articles that got attention. I even paid to attend two of their conferences. They have a megaphone.

At Wanderlust Society, we liked building. Our entire team hailed from Amazon, and at the megacorp we had to worry about the usability of our features. As a User Experience Designer there, I was not at the level to decide if a project should be done or not done. I was not responsible for driving traffic to said features. I never had to worry if someone didn’t want our solution, I only had to worry if it was usable, then A/B test it to see if the feature incrementally lifted sales.

In my first startup, Bridalnet/The Wedding Channel, we built it and they came. We were the original online wedding planning portal site, and the brides came in droves. We realized that brides were spending up to four hours looking at dresses on our site! We had content and people clicked. If there was an article about the wedding industry, we were in it. We were the Seth Godin purple cow. We were the next big thing.

My co-founder, now husband, Andy Kleitsch’s superpower was business development. Our url was on hundreds of pages of bridal magazines monthly, and we owned the search word “wedding” on Yahoo. There was a lot of low hanging fruit for us to grab, and we were all over it, grabbing as quickly as possible to create an empire.

Now the world is different. The days of the low hanging fruit are over, and everything that is on the web has so much competition. Unless you are doing something so radical, new and different that the press wants to constantly report on it, marketing is needed.

We neglected marketing. We neglected the funnel. We focused on building. We had a giant hole on the team. But we could build and were building, This false hope of, “Just one more feature to make the product better,” was killing us slowly.

What should we have been doing? Testing landing pages. Testing messaging. Getting crisp on what our value proposition was/would be BEFORE we started building. Once we did start testing landing pages and social media ad campaigns, we discovered a business model in that Society Members were willing to pay for customized itineraries. But by this time our runway was exhausted.

I also had the idea that if you had a good product, you wouldn’t need the brute force hustling that we used in my last startup. Back then, my husband was my business partner and he recently reminded me of the time I brewed him a pot of coffee, put him in a room and said, “Don’t come out until you’ve made a sale.” We were ALL IN. The company was sink or swim. Pay the mortgage this month or I had to get another job to pay the bills. So I did. I worked two jobs and it honestly about killed me. I did not want to go down that path again, where my health was declining and my bank account dwindling. I especially did not want to take this approach when I have two kids who I want to watch grow up. I wanted to take a more academic approach this time. Focus on the product.

What would have helped? Money. I didn’t feel like I had the cojones to pitch vaporware like it was going to be The Next Big Thing, and neither did anyone on the team, even the males with the real cojones.

We felt that our best bet for funding was to be able to build a prototype, and get some traction before raising funds. But honestly, no one was good at pitching or really wanted to quit building our product to pitch. We were really hoping we could build a product and “growth hack” it into success, but because the travel industry is such a crowded and mature space we could have used money to speed us along to develop our product, and hone our marketing.

So Wanderlust Society has failed.

Truth to be told, this is not entirely a sad story. Here are a few things that went right and that I’ll carry with me forever.

Amazing team
Before I started recruiting for Wanderlust Society I had a mini-manifesto. “Hire the best and the brightest and treat them accordingly.” I was able to surround myself with incredible humans, and create a work environment where everyone felt empowered to thrive. If not for a better business model, our team was ready to go the distance. I feel so much gratitude for these people, and that I got to spend my time with my team solving a problems we were passionate about — helping others take great trips.

I found a tribe
I may not have made a big pile of money, but came away with a gold mine of friends. The Female Founders Alliance, Janis Machala’s CEO Group, Startup Week and the F Bomb Breakfast Club were great places for me to meet other female founders. The women in these groups became confidantes, cheerleaders, and even users of Wanderlust Society.

My mental health is in check
Okay, I admit that I didn’t always sleep very well during this journey, but I always tried to log the hours in the bed, regardless if my mind was still racing. (Anyone have tips for this?) I made a vow to take care of my mental and physical health, because without either, you have nothing. I slept (attempted), ate, exercised, and made time for friends and family. Startups should be seen as a marathon, not as a sprint. Conserve energy wisely while you hustle.

I’m not in debt
Our team knew that creating a startup was a gamble. While we did put in massive time and effort, we kept expenses in check and were as scrappy as possible.

Massive personal growth
I married my husband, an extreme extrovert so I would never have to answer the door, the phone, or speak in public again. But running a company and being the face of it means pitching and articulating your mission statement and vision as much, and as often, as possible. I had to be comfortable with more public speaking. A female mentor suggested reading The Charisma Myth, which I now recommend to other people looking to build confidence with public speaking and leadership.

I also had to become somewhat proficient in areas I had not previously considered: research, pitch-deck building, social media, PR, marketing, blogging, and logistics management, just to name a few.

I probably learned more in the last three years than in the previous 30 years.

And finally, I’m hoping this massive undertaking will allow me to “fail up.” Perhaps future employers and colleagues will see I can pitch a vision, recruit talent, research, launch and market a product… and also know when to say, “Adios.”


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