A tech startup recap, 12 months in

By Drew Meyers , written on October 12, 2013

From The News Desk

You hear it everywhere. Startups are hard. Really damn hard.

I  concur.

We're 12 months into Oh Hey World -- heck, 20 months if you include the time I researched the travel market from February until August of 2012. This is my honest assessment of our successes, failures, and stumbling points one year into our tech startup.


Before I get too far in, I want to detail the why behind Oh Hey World. If you don't know the why behind your work then it's destined to fail before you even start. My passion is in forming meaningful connections between people with shared passions. For me, this means creating in-person connections when possible (the holy grail), or over email or skype or phone at the very least.

My dream: two people with shared interests meeting eye to eye in the same room and  forming real relationships. This is where the magic in life happens. People need to look up in life from time to time to enjoy the moment, to enjoy the passions, ideas and company of others who share their interests in life. Our aim is to build a tool that creates this value for every person using it in a fast, simple way (more on that here).


At Christmastime 2011, I made a big change in my life. I left my job as a marketing director for Virtual Results, an internet marketing firm in the real estate vertical, and I flew to Asia with a goal to figure out what I wanted to do next. Within six weeks, I knew I wanted a startup of my own, and travel was the logical vertical since that's where my passion lies and all my money is spent. Yes, I'll admit it -- I'm a travel addict.

And with the seed planted to build a startup in the travel space, I did the first logical step: research. I spent February through August 2012 researching the travel space, talking to travelers, wireframing concepts, and overseeing early designs -- all the while looking for that ever elusive tech co-founder. In August 2012, I found that co-founder while at Startup Abroad in Bali. Eric was a natural fit with the vision -- he shared a passion for travel and coupled that with an extensive knowledge of the technology side of startups from building apps to consulting for Fortune 500 companies.

Product thinking

When I researched why more people don't travel, and even when I talked about travel with friends, I was met with two main obstacles over and over. The first was cost, and the second was some iteration of having no travel companions and/or being scared of the unknown. Using those two truths that resonated for people interested in travel, I first focused on the financial issues and looked at the perceived cost of travel, which stands as a barrier for many people. Before starting full development, we work-shopped the ideas and issues for several months before ultimately pivoting to the social side of travel. I pivoted to the second truth that resonated as a pain point in travel for two primary reasons:

  • Getting accurate cost data to comprehensively cover the globe would be a very slow growth business, without real hockey stick potential.
  • My own travel profile recently shifted from one where cost was the most important consideration when travel planning to one in which I was going to take the trips I wanted to take, with the people I wanted to go with -- and cost being a secondary factor. After working at Zillow for four and a half years, I knew what it takes to build a startup, and I didn't want to spend five years of my life (at a minimum) working on solving a problem I didn't really care about anymore.

We started off with the goal of helping travelers share their location with the people who care.


Our MVP was a one click check-in. At its simplest form: think FourSquare, but at the city level. One click sends your current city (ie "Seattle, WA") to all of the following:

  • Email recipients -- ie your parents, 3 aunts, 4 uncles, and 2 cousins.
  • Text recipients -- ie your brother, sister-in-law, and 3 best friends
  • Twitter
  • Facebook
  • Your travel blog via our WordPress plugin (this was a planned addition that was told to all our early testers)
On the other side of the one-click check-in and notification, it showed you the three tiers of people you may be interested in knowing who live nearby: your friends (based on your Facebook account), all nearby travelers checked-into the Oh Hey World community, and your friends of friends (based on Facebook graph).

MVP feedback

The aggregate product offering was interesting to just about everyone. But not interesting enough for the vast majority of people to change their habits away from what they were currently doing (text, email, phone). The travel bloggers were the primary crowd interested in changing their behavior.

With all that said, we pressed on anyway (mistake #.5) and started iterating on that bare-bones MVP. Like every startup before us, and every startup after, we made our fair share of mistakes.

Mistake No. 1

We designed for the desktop first. Certainly some of this decision was because I had been traveling abroad for the past several years. I had an iPhone 3Gs which was god-awful slow. My life did not revolve around my phone, and everything I did was still on a desktop. The mobile craze isn't nearly as pronounced abroad as it is in the United States because, while everyone has cell phones and texts like crazy, most people don't have smart phones -- partly due to expensive data costs. Once back in the US and gathering feedback, it quickly became apparent that this needed to be a mobile first, or mobile only, solution.

Mistake No. 2

So, we realized it had to be mobile. What better way to do mobile than a native iOS app? We brought Will Moyer on as our lead designer and got to work. Well, we designed and started building our iOS app before we knew exactly what specific use case we should be solving. Should we focus on conferences? Festivals? Arriving at a hotel? At airports? Train stations? Students? Retirees?

With about 75 percent of our iOS app built, we put the brakes on our iOS development in late 2012 and decided to iterate on our mobile web experience until we nailed the right scenario. The logic was simple: iterating in a mobile web environment is quicker and cheaper than iterating a native iOS app.

Mistake No. 3

We tried to boil the ocean in our attempt to create more value for encouraging people to consistently use the site. We built location aware lists and tag result pages to help people find others nearby. We built "welcome kits" to surface local travel advice. We built comments on check-ins to give it a more social feel. We built communities.

In short? There is a lot going on within the Oh Hey World user experience, and many people don't know the one thing they should be using it for.

That's obviously a problem.


Contrary to what you may be thinking right now, we didn't do everything wrong. The one true pain point we have solved is one I absolutely knew existed; travel bloggers keeping their "currently in" on their blogs up to date. I struggled with this constantly while traveling from 2010 until late 2012. My about page seemed to always have the wrong location, since I always forget to change it when I moved to a new city. Those using our site consistently today are those who have our WordPress plugin installed and are using it as an easier way to update their "currently in" module on their travel blog. That's a small, but influential group of people. They are the true content creators of the travel vertical -- traveling constantly, blogging, and taking photos. In their respective networks, they are all thought of as the "travel people" everyone asks for advice when they are planning a trip.

From this same crowd, we've also gotten great feedback on the digital nomad welcome kits we curated for Southeast Asia.


Oh Hey World was bootstrapped entirely out of my own pocket, largely from Zillow stock that I sold. In May, we got to the end of the road in terms of that runway to keep funneling my own cash into it and we took on a big consulting project building an iOS app. Eric and I worked on that for three months together, and Eric is still working on that project.

We have talked to a number of potential investors over the last six months, and the overarching feedback we've received is that while they like the product and design, they want us to come back to them with user traction. The whole travel industry makes money from hotel bookings, and Oh Hey World wasn't focused directly on that space -- our monetization potential was always a question mark as a result. As those in the travel industry know, the social travel space is an incredibly difficult vertical to enter, and many investors have lost money in the space already (many, many startups have tried to tackle it, and failed).

Potential pivots considered along the way

  • Relocation -- The information someone is looking to figure out about the place they are moving is largely the same as when they are traveling to a given location (entire thinking outlined here).
  • Conferences -- Help conferences build a better arrival experience for their attendees.
  • Hotels -- Digital concierge offering that allows their guests to check-in and ask the concierge desk questions via an app.
  • Tour companies -- Enable those who have booked tours to find out who else is going on their tour ahead of time.

People like the look and feel of the current product, but we are getting feedback such as...

  • It would be great if all my friends were using it
  • It would be great if everyone who cares about microfinance were using it
  • It would be great if a large number of people in Barcelona were using it
  • It would be great if there was great advice for every destination in Thailand
Hence, our largest challenge is filling the travel platform we've built with enough people and data to make it a viable offering for travelers looking for either advice or connections in any city.

Timeline & Status

  • Earliest MVP -- September 2012
  • Desktop MVP version -- October 2012
  • iOS TestFlight version -- November 2012
  • Mobile web revamp -- January 2013
  • Mobile web launch into a "limited" Beta -- April 2013
  • Launch into "unlimited" Beta -- October 2013
Currently, there are roughly 900 registered users.

High Level Learnings

  • Pick your poison. Don't boil the ocean.
  • Starting a company with 6 million in the bank before a line of code was written (Zillow's scenario in 2005) is a very different dynamic than bootstrapping.
  • However hard you think early customer acquisition will be? Multiply that by 25X.
Next step

Let's go back to my original "why" of connecting people with shared passions in person. We're going to nail our "location aware community" pages (early "Kiva" community can be seen here), and focus the entire experience around discovering and connecting with the people nearby in the communities that matter to you. The two types of people who we know are interested in this scenario are entrepreneurs and the "social good" crowd. Both types of individuals are keenly interested in connecting and meeting with other like minded people looking to make a dent in the world. We'll highlight 3-6 communities on the home page and target all messaging toward those specific passionate communities. Kiva and Mothers Fighting for Others, are the first two, and we will identify an additional 1-4 passion communities to target.

In the simplest sense, we're connecting a community of travelers who give a shit about making this world better. That's always been our core goal... sitting right there on our mission page, we just haven't focused directly on it since we thought we could somehow reach everyone at the same time with a location sharing platform rather than connecting passionate communities one by one. As you've often heard, targeting everyone with one product offering and message seldom - if ever - works. That was certainly true in our case.

To summarize, 12 months after breaking ground with our first line of code, we've learned tech startups are damn hard, and there are no shortcuts. As Steve Jobs said at the All Things Digital Conference in 2007...

If you don’t love it, you’re not having fun doing it, you don’t really love it, you’re going to give up. And that’s what happens to most people actually. If you really look at the ones that ended up successful in the eyes of society and the ones that didn’t, often times the ones that are successful love what they did so they can persevere when it got really tough. And the ones that didn’t love it, quit. Cause they’re sane. Who would want to put up with this stuff if you don’t love it?
Exactly. Short of finding the absolute perfect investor who believes in and understands the true power and monetization opportunity of engaged and intimate communities (inevitably in person interactions means money is being spent), we're going to bootstrap longer with consulting work to prove out additional user traction.

One thing I know? Even if it takes five years, and even if I have to do this on the side, the mission is one absolutely worth chasing. Connecting changemakers is what this world needs most right now. Great things happen when people get in the same room and talk; doers will accomplish more with a larger network of others who operate under the same mindset. There's nothing I want more than to enable those amazing connections to happen more often, and more easily, than they do now.

What if the next Pierre Omidyar or Bill Gates meets his co-founder via Oh Hey World and they build an amazing company together that helps the world, and funnel all their money into philanthropic endeavors afterwards? A short 10 or 15 minute discussion is all it takes to kick off that type of relationship.

That possibility makes the whole thing worth it by itself.