Notes from a failed startup. Or was it a hobby?


Perhaps we learn more when things go wrong….this post also could be titled, How to keep your startup from turning into a hobby.

I learned a tremendous amount in 2010 – 2011  about iOS development, but I learned even more about what to avoid the next time I form a startup. Towards the beginning of 2010 a friend and I formed the idea for a startup around a topic we both really enjoyed and know a lot about: travel. Specifically, we wanted to create in-depth guides that enriched the experience of travel beyond the checklist of tourist sites listed in most guidebooks. Our slogan: destinations in context.

My business partner was a domain expert: a highly experienced tour guide who had extensive contact over the years with customers. I had a deep background in technology and management experience in a non-profit environment. We made mistakes by not understanding the unique nature of a startup.

None of this is a list of regrets or complaints. This is not a lament, “If we had only done that, then…” No, this is all about learning for next time.

I do believe that my business partner and I shared a vision of our products and what the  company could accomplish. We were very excited and motivated by that. But I realized too late that we did not share an understanding of the process to grow the business.

There’s a wonderful description of a startup by Steve Blank: “a startup is a temporary organization designed to search for a repeatable and scalable business model.

We had a vague idea of our business model but didn’t put the effort into really thinking through the elements that comprise a business model.

Too much initial attention to branding. We placed enormous effort in devising a brand name. Months (!) of conversations across two continents resulted in brainstorming of nearly a hundred domain names. Finally, I simply gave in and agreed to one of my partner’s suggestions. I didn’t love the name but it worked fine. (So would have about a dozen others that were discarded, but that’s my view.) Somewhere there’s a classic statement, “Your brand is not your logo.” (Or something like that.) Your domain name is also not your brand. It’s an important element but there are so many more things that need deep thought when creating a startup.

Too narrow of a niche requires scaling to many destinations. The problem with travel content is that once you acquire a loyal customer then that customer is not likely to travel again for another year. And then they’re most likely to go to a different destination and probably not to the one other city we were writing about. See a post I wrote, “leisures travelers don’t scale“. We knew we needed to cover other destinations but we both didn’t grasp that the only way to sustain the business was by generating a significant number of guides to many different cities. That simply cannot be done with one or two people writing content, especially if the content is well researched and extensive. We did not understand the need to scale and the resources required. Mainly, we ignored scalability. Of course our startup failed.

Thought we knew the customer. We created a product that we ourselves wanted as travelers and assumed that there would be plenty of others like us that would want the same. I don’t think the product concept is bad even today, but we didn’t explore the product market fit adequately. This also links back to the narrow niche, the urgency to scale, and resources for doing so. We should have examined the possible customer segments and identified if there were products more easily scalable to a broader segment. “But that’s not what we want to do”, is a common phrase when a business is very focused on its product idea and not willing to see whether it really fits the market in a way that can work for the business.

In other words, we were not willing to pivot in our search for a business model. 

Perfecting & perfecting a 1.0 release. Our first product, an iPhone app that provided a guided tour of a prominent historic & cultural attraction in a major city, took almost a year to produce. As the actual developer of that app I can testify that it could have been completed in less than 2 months. I wanted to get a good enough app out on the market and improve it with incremental development while we continued pushing out other products. This was not the kind of app that was going to sell thousands or hundreds of copies in the first few months. Instead, we tweaked the design, the content, and functionality for months. My business partner, who was supposed to be focused on content, couldn’t restrain himself from adjusting every aspect of the design even though we had a professional graphic designer working with us. I ended up having to mediate conflicts with the designer (who was also my spouse). There was a need to create the perfect app, perhaps even the best iPhone travel app ever designed. Really, did we need to do that? In a bootstrapped startup did we need to spend all our resources in this manner?  We were too focused on perfecting the launch release rather than getting it out into the hands of customers, listening to customers and evolving the business strategy. The argument for the extensive 1.0 release ran like this, “If it’s not great, then people won’t buy anything else from us. I wouldn’t.” How did we come to that conclusion? Potential customers didn’t tell us that. It was an assumption without validation.

Admittedly, during the year of developing this product I didn’t work on it full-time, but about 80% of the time. Had to pay the bills with freelance work, plus I had a newborn child. And one month I stopped work completely on the product in order to earn an additional income; that was when the product was 5 months behind schedule. My spouse encouraged me to abandon it completely, but I wanted to finish at least this initial app.

A 50/50 partnership leads to no clear decision-making. We needed a CEO to make decisions, but probably neither of us would have worked for the other. The company would have dissolved within a week. Maybe that would have been the real test of the partnership and how well we would have worked together. But someone needed to guide the business, make decisions, and keep things moving ahead. A startup with 50/50 decision making does not work.

Ultimately, the money ran out. We had made the decision early on to bootstrap this startup and not seek external funding. (No one would have given us funding anyway with this business model.) In the last few months I had prepared spreadsheets with financial projections that would be needed to sustain the business and estimated the volume of sales required to meet those finances. After our first product launched (with sales far under expectations) we immediately moved into developing the next product. We did recognize the need to get multiple products on the market but we just didn’t examine if we had the right product or not.

Just before the end I invited my business partner to discuss a new strategy for the business, a pivot (if you will, though I didn’t call it that). After more than a year and a half of devoting the majority of my time to this business I had no more money left to put in. For me to continue I needed funding. We needed a strategy to continue and that meant a serious rethinking of our business and how we moved forward, particularly how we continued to finance the operation. Rather than rethinking the business my partner suggested that I take a job, save money and come back to work with him once I had a savings. The next week I took another job.

I learned a lot from that experience. A lot was my fault in not assertively pursuing strategies that I knew would be better for the company, but would those have survived the 50/50 decision-making?  Unfortunately, this startup ruined a friendship. My former business partner is still hard at work pursuing the same business. Maybe it’s working for him, but in hindsight, it’s clear that the strategy we employed could only support one person with a very modest residual income. That isn’t a startup, it’s a hobby.

City touring for those who don’t use tour guides


The ability of Google’s Field Trip app to let a person know what’s around them as they walk through a city has been a long desired feature for travel apps. Not everyone wants to employ a tour guide. But this type of ambient local discovery app is not going to present a major disruption to the walking tour business with a real guide. People hire tour guides for a different reason. (More on that in another post.)

This type of app will have a greater impact on travel publishing by further reducing the perceived need to purchase a guidebook. For a traveler comfortable wandering a city a Field Trip app is a great asset to have around. Personally, I find unplanned excursions to be a great way of exploring an area. In the copywriting on the companion site for the app Google re-enforces that theme repeatedly:

there is no path, only the one you make”

“Field Trip day is dedicated to the art of the wander, and discovery through exploration”

“There are no right choices, no wrong turns – but there are treasures to be uncovered just out of sight.”

“This is not a tour. There is no guide. It is discovery, pure & simple.

Odd it might seem then for a product that targets unplanned use is that Google sponsored organized Field Trip days when the app was launched. Perhaps that simply was as a means of gaining feedback via a public beta test (without calling it that).

Note that the positioning of this product is for the local explorer and not the traveler. People are more comfortable exploring the familiar but I can see the appeal of ambient local discovery apps to travelers with an adventurous spirit.

For a review of the Field Trip app see the article by Rachel Metz in Technology Review, and Metz points out that the app would be most useful on vacations when a person is more likely to have the time for random interruptions. As most of us go about our daily lives we really don’t have the time to be pestered by historical tidbits or the latest deal down the block. Fortunately, the ability to set notification levels and the type of data is built into the app.

I’m hoping we’ll see the capabilities of this app built into the future Project Glass. If so, then Google has a huge winner on their hands.

What could convince me to develop for Android


I’m an iOS developer, but I don’t have a religious affinity towards Apple. I do like Apple products. I really enjoy coding in Objective-C. Yes, really. Mainly, though, I’m an iOS developer because Apple presents the most profitable platform for developers at the moment. With the iOS SDK I can create apps that people will use, and I can earn a living from that creativity. Yeah, I like that. With the iPhone and iPad Apple is an exciting platform for a developer.

But that may not always be the case. I’m keeping a close eye on what’s emerging at Google (no pun intended). If an SDK is released for Project Glass then I’ll want to use it. I have no idea whether Project Glass is powered by Android. Presumably, that is the case.

I also would be very interested in developing for Kindle Fire if Amazon had a more robust SDK. I’m not interested in developing e-books (though as a former librarian I have a tremendous love for books and e-books). I’m more interested in visual alternatives to long-form narratives and, sadly, the Kindle platform doesn’t seem to support that very well in comparison to the iPad.

We’ll see what happens with Project Glass, but I’m sensing it’s time to brush up on my Java skills.

“Software development: the middle class job of the next generation”


I’ve never been entirely comfortable self identifying myself as a software developer. My degrees are in English and Library & Information Science. But I make a good living developing software. It’s rewarding, not just financially, but creatively as well. Indeed, it’s the creativity that keeps me developing with software.

There are various degrees of software development & just as many skill levels. In a way, software development is like writing. Anyone can do it with a bit of learning. But, like good writing, good software development takes a lot of practice and learning to do extremely well.

For most people software development is a mystery filled with odd incantations performed by pudgy bearded men in dark rooms.

The more we understand about software the more we grasp the limitations and possibilities of technology. After all, technology simply does what it’s programmed to do. There’s no real mystery behind these logical machines.

Unlike the 1980s when I attended college it’s now cool to aspire to a career in software development or entrepreneurship.  I’m still not sure if those skills should be emphasized in college curriculums. Analytical and critical thinking are the most important skills that anyone can learn in formal education. Obviously with the right teachers those skills can be incorporated into computer science coursework. Technology changes so fast that anyone wanting to achieve proficiency in software development must have the ability to learn on one’s own.

In episode 65 of This Week in Venture Capital Mark Suster talks with Eric Ries, author of The Lean Startup. Around the 1:05 mark Suster makes the comment that software development is the the “middle class job of the next generation”.  Suster briefly mentioned the routine aspect of software work that needs to be done. While I lust after the creativity of software development, every developer knows that so much of this work is in fixing bugs, updating code prepared by others, and simply maintaining code. Systems change constantly and manpower is needed to keep the code updated. That’s where a lot of the jobs exist. And for those positions you don’t need an extensive engineering background.

Ries concurs with the addition that computer programming and entrepreneurship are part of a new literacy for the next generation.

Suster makes what some may see as a controversial statement,  “I think we need to get to a place, and this is going to sound backwards, not every child in America is expected to go to a four-year university.” I would go further and say that perhaps the most intelligent children do not need a four-year college or university, provided that they already had learned how to learn.

Headset as disrupting factor in mobile


We all know that Google is working on a headset that will make computing hands-free. No one knows if Apple has anything like that under development. I suspect there is something happening in a locked-room behind a veil of secrecy in Cupertino. (If not, maybe Jony Ive could release a line of designer eyewear after he retires from Apple! May not be wearable computing but sure would be trendy.)

As one thinks more about Google’s Project Glass it becomes obvious that a headset of some sort is going to be a huge disrupting factor in mobile computing. I will go as far as to say that it is the future of mobile computing. Not putting a date to that but in a few years we all will have forgotten about how companies attempted to broaden their mobile advantage by increasing the screen size of the smartphones we pulled from our pockets.  The future mobile computer will be resting on our head and visual display will take on an entirely new dynamic.

A key question is whether Apple has the determination to create a product that kills the iPhone. Today that sounds crazy but we’ve all read The Innovator’s Dilemma. Google is clearly betting on a wearable headset and it might very well propel Google past Apple at some point down the road in a way that Android on smartphones never accomplished.

In the latter part of episode 56 of The Critical Path (starting around the 57 minute mark), Horace Didiu discusses this topic with guest James Allworth of Harvard Business School Forum for Growth and Innovation. Horace advises “nurture the disruptor…the opposite to whatever sustains you.”

Allworth brings up Google’s Project Glass as potential for disrupting mobile computing (1.03 mark): “I think wearable computing. There’s definitely something there…a lot of value in getting the information on a passive basis rather than the active basis of sticking your hand in your pocket when you need to find something out.”

“We have to do a jobs to be done analysis”, according to Horace, “to understand what people hire these products for, even if they’re not able to tell you… I use the term mobile computing as the overall theme of what’s happening as versus a phone…something that helps you get things done in your life…it’s the apps taking on the job, not the phone itself…Still opportunity above where we are. That we may have reached the ultimate communicator product but we haven’t achieved the ultimate personal assistant product.”

Allworth went on to examine the functionality of icons and how data is accessed by function based on icons. He doesn’t think that approach is going to last that much longer because it does not scale. “I think there’s something about the Google Glasses. It’s going to force them to really, really crack the interface. Because if you got this thing up in your field of vision 24 hours a day , seven days a week, you’re not going to want to scroll through applications. It’s going to have to get more intelligent in thinking about what’s the bit of information you need to know right now?” That ties in directly with the context functionality that Scoble is talking about as next challenges for iOS and Android.

Getting familiar with Google Glass


I mentioned that Google’s Field Trip app hints at the future of Google and its Project Glass. I wanted to learn more about Google Glasses. First thing I learned: don’t call them glasses…there’s not a lens…just a tiny display at the upper-right. Puzzling how that’s going to work…until you think more about it.

David Pogue in in an article titled Google Glass and the Future of Technology calls it an entirely new gadget category…”like a smartphone that you never have to take out of your pocket”. He also has one of the few first-person accounts of it’s like to wear Google Glass:

…the tiny screen is completely invisible when you’re talking or driving or reading. You just forget about it completely. There’s nothing at all between your eyes and whatever, or whomever, you’re looking at.

And yet when you do focus on the screen, shifting your gaze up and to the right, that tiny half-inch display is surprisingly immersive. It’s as though you’re looking at a big laptop screen or something.

If you wear glasses you can try a little experiment. Shift the lens of your glasses up a bit above your eye. Then glance up at the lens: it’s remarkably clear. Hmmm, I wonder if that’s the effect of Google Glass. Having worn glasses for my nearsighted vision since the age of ten, I’ve long been used to that bit of blurred vision outside of the frame. (It doesn’t take a huge stretch of the imagination to see how Google Glass could be adapted to also include lens for corrective vision.)

Beyond the hardware innovation the real advantage to users is that Google Glass presents the possibility of a hands-free approach to interacting with a computing device. While a touchpad is integrated in the earpiece it’s certain that voice control offers more advantages.

Earlier in the year Google released a video that gives a point-of-view perspective as to how Google Glass might work. Of course, that video is clearly just a concept rendering with a lot of help from motion graphic designers and not an actual recording of what it’s like to actually use the product.

At the Google I/O 2012 conference Sergey Brin shows the video capture capabilities of Google Glass (“being able to share what you’re seeing live”) by having a group of skydivers stream real-time video from their Google Glass to the auditorium.

Will people actually wear these things? That’s an obvious question, but we already do wear odd things on our bodies. Farhad Manjoo, writing for Technology Review, places Google Glass in a long line of “functional wearable objects—think of glasses, monocles, wristwatches”. Bluetooth headsets being among the latest in that line. And there’s those earplugs with thin cables that trail down into our pockets connecting to our smartphones.

Another first-person account with Google Glass

Spencer E. Ante writes of his experiences with Google Glass, “…long-term potential. The device fit well. It was easy to snap a picture or video without taking my smartphone out of my pocket. It was cool to see the information there in front of my right eye, though a little disorienting.”

Google Glass holds the potential for seamless access to the digital world without managing a gadget.

“leisure travelers don’t scale”


The quote “leisure travelers don’t scale” is from an interview with Rafat Ali (founder of paidcontent) at the Next Big Thing. (At the 6:35 mark in the video if you want to skip over him talking about his new venture Skift, though if you’re interested in the travel industry then you should become familiar with Skift.)

Skift also aims at informing the business traveler rather than the leisure traveler. The business person might travel several times a month. Anyone involved in a travel startup knows that it’s difficult to scale a business around consumers traveling to specific destinations. How many times does a person travel for leisure. Ali says “once, twice, thrice a year”. How many times does a person travel internationally? Only a few people do so even once a year.

Even if you build a loyal customer with your superb guide to the basket weaving of the Peruvian highlands, it’s going to be another year or more (if ever) before that fan buys your insightful, one-of-a-kind guide to the public sculpture of Odessa. Okay, that example is an extreme niche but it’s hard to grow a business by selling content to leisure travelers. You need content to dozens, if not a hundred or more, destinations if your travel content business is to sustain a staff of more than one based on revenue alone.

A core requirement in forming a startup is to spend time reflecting on the product you’re developing and, particularly, what problems are people buying that product to solve? Are there enough customers to actually build a business that can grow, or is the business so narrowly defined that it’s potential is little more than a supplementary income for one person? The latter is not a startup.

In the interview with Ali the moderator Scott Kurnit (found of about.com) asked a wonderful question, “Twenty years into the Internet, why do we get to do something new…why hasn’t it all been done…why wasn’t this done 5 years ago?”

As Kurnit suggests, it’s often because technology has changed (particularly with regards to mobile) or consumers have changed. Ali goes a step further and reveals the forumla behind his successful strategy, “I love businesses that are a layer on top of existing businesses.”

For those of us who lovel travel, Ali offers a vision at the 8.33 mark in the video as to why travel is important:  “travel is a lens that can bring understanding to the world”.

The challenge is creating a livelihood through a travel startup.

Field Trip app hints at Google’s future


Aimed at travelers & locals curious to learn more about their city, Google’s Field Trip app (Android only for now) serves up content based on your specific location within that city. The app launches today in six cities.

The app, oddly for a Google product, presents a very nice visual design. There’s  even a sleek made-for-tv commercial. What is Google up to with this app?

An insightful post on the New York Times Bit blog predicts that the app “reveals a lot about the big directions Google wants to go.”

Note the binocular/field glasses motif that also forms the icon for the Field Trip app.

Are those field glasses just ornamentation, clever use of graphics,  or a hint towards Google’s future attempt to disrupt mobile computing with Google Glass & wearable computing?

Where are the Apps for the Armchair Traveler?


Mobile developers & entrepreneurs occasionally forget that smartphones and tablets are often used in the home. The iPad makes an excellent lean-back device. We mostly recognize that tablets excel as devices for reading, watching, shopping, & other “passive” activities. Obviously I’m leaving out a wide range of tablet uses but for the sake of this particular analysis let’s focus on that passive behavior of consuming content.

People create startups based around ideas where they understand the possibilities. Are their untapped possibilities to provide valued products to users sitting at home in a cozy chair?

The Armchair Traveler

I continued to be astonished at the absence of apps aimed at the armchair traveler: the person sitting at home who is planning a trip or, very likely, just curious to learn about the world.

The Fotopedia apps are among the best examples of current apps that serve the armchair traveler by offering spectacular images by professional photographers.

A couple of print publishers that have surprised me by not doing more with apps are DK and Insight Guides.

DK’s Eyewitness Travel books are beautifully designed for appealing specifically the person who is not at that destination.  Those are great books for planning a trip & figuring out the sights you want to see. But they’re even better for getting a sense of a place without ever going there.

More than 10 years ago I was browsing in a bookstore with a friend when I brought the  DK Eyewitness Travel Guide: Japan

My friend, rather curiously, asked, “When are you going to Japan?”

I answered, “I don’t know. I just want to learn about it.” A decade later I’ve still not been to Japan, but I have purchased many DK guidebooks. Yet, as someone who has traveled a lot, I would never take one of those books on a trip. That’s not because I can get all sorts of information online these days. It’s because the books are simply not that useful at a destination. Better to have a Lonely Planet or Rough Guide.

Since DK truly understands the visual I was excited when they released an app for iPad. Sigh, as a long-time DK customer how disappointed I was at their iPad offering. It was okay but didn’t inspire me in the same way as the printed edition. That’s not because print has any intrinsic quality over digital in this case. I ended up deleting the app after not much use and am really hesitant to ever buy another app from DK. Hmmm, but I would still buy their books and will give an app by DK another chance at some point.

I mentioned Insight Guides, which is a very different type of publisher from DK. Whereas DK publishes visually rich, but content thin, volumes. Insight Guides produces in-depth, mostly historical accounts of destinations. Great opportunity for repurposing these products onto a new platform, but the publisher has taken the rather bland approach of converting to e-books. Well, that’s a step and the title offering should certainly exist as -ebooks. I’m not doubting that.

The holdback

What’s keeping publishers from creating more exciting apps for armchair travelers? Certainly the cost & complexity of app development is the major factor. Then there’s the issue of multiple platforms. Not only does technical expertise need acquiring, but also the platform requires a new way of conceptualizing the product. And that’s the really hard part.

Reading in Print Again


Last night as I climbed into bed I discovered that the battery on the iPad was empty. Urgh. No bedtime video watching or reading. Well, I could have used the iPhone but I prefer the larger screen iPad. So I went over to the bookshelf where I still maintain a fairly good collection of print books. It had been well over a year since I’ve read a print book. All my reading this last year has been on the iPad, using either the iBooks or Kindle apps.

My reading choice:

Great book!