FailCon: Startup Reality

November 3, 2011

I didn’t know what to expect going into FailCon, but it turned out to be the best conference I’ve been to. Why? Because it’s a startup event grounded in reality. It completely challenges the fantasy of overnight success. It turns out most startups take years to build, and that most successful founders have had multiple startups fail on the path to success.

Highlights Included:

  • Joe Gebbia of Airbnb talking about their years-long trough of sorrow. Rather than “fail fast”, they stuck with their vision for years before finding product-market fit.
  • Travis Kalanick of Uber talking about his previous startup, which dragged on for something like 9 years – with no pay until exit.
  • Vinod Khosla of Khosla Ventures talking about failure. Favorite quote: “My willingness to fail gives me the ability to succeed”.

Having recently launched a startup and entered the trough of sorrow, this event’s timing couldn’t be any better. Entrepreneurs need to know that the trough of sorrow is normal, and that it typically takes years to get to product-market fit. Ideally, entrepreneurs should know this before they get started. I worry that it’s not clear to many people getting started that, even in today’s market, their startup is likely to take 3-7 years to succeed, and is even more likely to fail.


TechCrunch Disrupt: The Volunteers

September 16, 2011

As an entrepreneur and recent transplant to San Francisco, volunteering at Disrupt was a dream come true. I was able to experience the energy of the bay area startup scene first-hand, gaining insights from leaders and learning from new companies as they pitched on stage. I was even able to meet many of the speakers, since volunteering often meant walking them backstage. But the biggest surprise was my interactions with other volunteers. As panels were taking place on stage, there was an army of entrepreneurs-turned-volunteers hustling behind the scenes. The true entrepreneurial spirit was alive and well at TechCrunch Disrupt, and you didn’t need a $2,000 ticket to participate.

While the average attendee probably assumed they were dealing with college students, almost everyone I met was an entrepreneur. After all, that’s why I was there. As the co-founder of a bootstrapped startup named LazyMeter, I decided to volunteer and save myself the $2,000+ for a badge or table. And clearly I wasn’t the only one who thought of this. I met a 16-year-old from Chicago with a growing startup – his ability to position himself backstage and approach anyone he saw put my networking skills to shame. I met a partner in a fund in Utah who brought his portfolio out as volunteers to save money. I met a senior at Brandeis University in Boston who won a business plan competition at Harvard and had the foresight to check out the startup scene a year in advance of graduation day. I shared passionate conversations with other volunteers about seeking independence and a good life for our families, the sacrifices we made, and why high salaries at corporations have no appeal.

As you walk down the hall at a conference like Disrupt, the crowd doesn’t look at your face – they look at your nametag. When they see “volunteer”, they keep on walking. This is a mistake. Don’t underestimate the people in green shirts. For all you know, they may be building the next big thing. All the volunteers I met had one thing in common: they had a vision, and they did what’s necessary to make it happen. If you can get backstage at TechCrunch, anything is possible.

When Data Is Wrong

September 2, 2011

I love data. When I was a business analyst at Microsoft, I enjoyed unearthing insights that moved the business forward. But data worries me too – it can be misunderstood, and it can be misused.

Sometimes data points to an obvious direction that may be incorrect. For example, I believe the quality of movies has deteriorated since studios started making changes to movies from audience surveys. The data is used to convince directors and writers their instinct is wrong. But what people say is the best ending may actually leave less of an impression – the result is less memorable movies, and ultimately people not wanting to go to the theater any more. Meanwhile, the studios look at data showing a decline in theater attendance and attribute it to home theater systems. And so, they turn to surveys even more.

While data is key to the success of any startup, it can also lead you astray. When we launched the alpha of LazyMeter, reviews were mixed – while 50% loved it the other 50% couldn’t figure out how to use it. The data told us that an analogy to a music player we were using didn’t make sense for a to-do list. The clear suggestion was to change from iconography to text; for example, to change our play button to the text “Today”. We resisted because the iconography is the point of the product – it’s what enables us to make task management faster than pen and paper. Switching to text also would have made us appear like the many other task managers we sought to replace. We followed our gut, not the obvious action suggested by the data, and went about finding another way to improve the experience for new users.

We added documentation. We played with tooltips. We tweaked the active and inactive states for the navigation buttons. All efforts improved our adoption rates, but they still left much to be desired.

And then we realized something. The problem was not that people didn’t understand how to use our product. The problem was they didn’t understand what the product was doing for them. We weren’t explaining our product on our homepage. ‘Play means today’ makes a lot more sense if you know LazyMeter is your to-do list, one day at a time. We did a simple redesign with a wordpress template, focusing primarily on messaging. And we haven’t heard from a confused user since. Responses immediately went from “I don’t get it” to “this is simple and intuitive”. Registration and adoption rates went through the roof – without any major changes to the usability of the product.

While it was critical to have data showing us where users were getting stuck, the obvious suggestion to change the usability would have been a mistake. It’s important to realize data can paint the wrong picture. If it feels wrong, dig deeper.

The Power of One

June 14, 2011

Most meetings are non-eventful. You say you’ll keep in touch, and maybe you’re introduced to others. While the entrepreneur may fantasize about someone jumping out of their seat with excitement, it’s more likely they’ll see someone that just wants to get through the day.

It’s natural to feel like the goal of meetings is to make everyone excited about your product. But I’ve recently learned the goal at the beginning should be to find one more person truly passionate about your topic. Someone as excited about the problem you’re solving as you were when you took the plunge. Someone so excited that they want to jump in with you. This is true whether you’re talking to a potential advisor, investor or user.

Move forward. As you share your vision more openly, don’t be disenchanted by meetings that go nowhere. It only takes a single meeting to change things. A single person can change everything for your startup. Suddenly, the less productive meetings make sense, and don’t matter. Remember that even the best pitches will often be ignored.

Make your goals achievable, and keep moving. Start with 1, and then seek 1 more. If you can get 1 advisor, you can get 1 more. If you can get 1 fanatical user, you can get 1 more. If you can get 1 customer, you can get 1 more. Forget the dreams of overnight success. You’re doing a startup, and that means you’re building from the ground up.

Land Ho: The Product/Vision Click

May 17, 2011

Even if you know the problem you’re solving, it’s possible that you don’t know exactly what you’re building. While common advice says to build your product and get to market, this advice glazes over a key step: getting out of your head. As you think through the detailed solution that your market demands, it’s discouraging to look at startups that have found their mojo. Their founders talk about their vision as if it takes no thought at all; their product and marketing are remarkably focused and harmonious.

For most startups, finding this harmony is a tremendous amount of work. Fortunately, there’s a recognizable moment when your vision and product click. Suddenly your whole startup falls into place. The vision leaves your head, and the product becomes its voice. With each deploy, you immediately know what to build next. Your marketing goes from wordy and disjointed to short and sweet. Users respond positively, some fanatically. It’s a beautiful moment, especially if it takes you months to get there.

At LazyMeter, getting from “we’re building a task manager that doesn’t suck” to “the cure for your overwhelming to-do list” didn’t happen overnight. It may seem like a small leap, but it’s brought laser-sharp focus to our product development. We’re still at the beginning and we definitely have our work cut out for us. But fortunately, when it clicks, the product takes on a life of its own, and the whole team knows exactly where it’s going. It’s as if you’ve been lost at sea, and finally spot land in the distance.

One Life

May 3, 2011

On Saturday, I proposed on a sailboat on Bainbridge Island. When I started searching for a boat, the task seemed daunting, but a quick search on airbnb didn’t just locate a boat – it yielded a sailboat bed & breakfast. How romantic is that? I found the perfect restaurant for the night using yelp, and emailed with the chef to arrange a special desert. A simple update to my Facebook relationship status saved me hours of phone calls, allowing me to turn off my phone and enjoy quality time with my new fiancé. The internet didn’t just help me with my proposal: I met my fiancé on

The experience made me think about who I’d be without the internet. In college, almost all of my plans were made by instant message – I’ve never liked using the phone, and I was lucky enough to live in the first generation that could get away without it. I found my first job out of college, at a startup in New York City, through craigslist (along with a sublet, an apartment, furniture and a mover).   I even found my job at Microsoft through craigslist. The job was in internet advertising.

The internet has shaped my life as far back as I remember. As a shy teenager trying to figure out life, I realized I probably wasn’t the only one, so I started a website called Teen World where I gave others advice. Over time, it grew into an interactive community for young adults called CheekFreak. Around 1,000 users visited each week to escape the real world and be themselves, and it was a huge part of my identity. I only made a few hundred dollars before I went to college and shut it down, but I don’t regret all the work. I still smile when I read emails from visitors, including several who said they were considering suicide before visiting.

When you get knee deep in your startup, you get lost in topics like fundraising, usability and dashboards. But let’s not forget why we’re really here: to shape lives. While many think task management is a boring subject, I’m excited by how it directly ties to people’s quality of life. What if I can increase your free time? What if I can help you feel better at the end of the day? The spark that gives birth to most startups is a selfless realization that you can help others. Making it sustainable is secondary, and it’s only here that most fail.

When you read that 90% of startups fail, remember that the definition is strictly financial. Don’t forget that you originally set out to help people. You’re only a true failure if you don’t improve 1 user’s life. Of the 90% of “failed” startups, I wonder how many founders consider themselves failures. I wonder how many have a letter from a user that still makes them smile. I wonder how many are proud of the lives they shaped. And I wonder how many wouldn’t say their startup shaped them.

Don’t Blow Your Load: Plan Your PR

April 18, 2011

You know the saying that everyone gets 15 minutes of fame? It also applies to startups. Most startups will get one shot at attention; after that, they risk being old news. So I’m confused when I see startups go on a PR spree before their product is ready for the resulting traffic.

The best PR is held back to coincide with a product’s release. I have seen several cases of eager startups generating a blast of coverage well before their launch. While there’s nothing wrong with building awareness, the problem is news sources often won’t cover you again. Plus, the passionate early adopters that tried to use your product before probably won’t return. While you can capture traffic with a mailing list, it’s a problem if you can’t bring such a large group back when the product is actually ready. This issue was experienced by Freshdesk when they had 25,000 visitors from a post on Hacker News. In a blog post, they said “We had 150 new signups – too bad we didn’t have the product ready. I think we could have had much more if we had the product ready instead of having people signup and wait for the beta.”

One of my favorite startup blog posts is How We Knew When to Launch Our Startup by Vinicius Vacanti, co-founder of YipIt. He clearly explains why startups should not seek PR until they retain users and (preferably) they refer others. He says “You are a fisherman, your startup is your net and your goal is to catch as many of these fish as possible. If your net (your startup) isn’t well-built and ready for them, the fish will swim right by you and they’ll never come back.” First impressions are critical, and you only get one. Robert Scoble recently wrote about why “first experiences matter and are mattering more every day” in response to the launch of Color.

People ask for access to LazyMeter every day. While we diligently track each request, most are still waiting for their invitation because we’re obsessed with their first experience. Instead of letting everyone in, we grant access to cohorts that are the smallest size needed to monitor first experience and gather detailed feedback. After seeing how the users respond, we improve the product and then invite the next cohort. This strategy has worked extremely well: we collect very actionable feedback and focus our attention on improving the product versus supporting many more users. While we regret that some have had to wait months for access, we prefer they have a better first experience – both with the product and individual attention – so that they’re more likely to become loyal users. We will launch and seek PR when we see our new users returning, and asking to bring their friends. Call us old fashioned, but we don’t put out until launch day.