No one beat a path to my door

“Build a better mousetrap, and the world will beat a path to your door.”  ~Ralph Waldo Emerson

It is December 1999 — I am on top of the world. Two months prior, my first venture-backed company sold for $193 million. My second startup, ShoppingList, just closed another round of financing, raising tens of millions. We were pooh-poohing 9-figure acquisition offers. We were partying like it was… the end of the millennium! And I was insufferable.

It would take less than twelve months for everything to come crashing down. 

You may have heard of the dotcom boom and subsequent crash. Starting ShoppingList remains the pride of my life: I convinced over sixty smart, hardworking and adventurous souls to join me with just a dream and many promises. But having to lay off these same kindred spirits just two years later and ultimately having no choice but to shut down the company along with those promises was the most painful time of my life.

Still, I am grateful for it was through this tumultuous period that I started forging a worldview that guides me to this day: Yes, do build a better mousetrap — just don’t expect the world to beat a path to your door.

With millions raised, ShoppingList splurged on expensive radio campaigns and partnerships with AOL and Yahoo! where we actually had to pay them to put our content on their shopping sites (you had to be there to understand this upside down dotcom logic!). We were justifiably proud of these efforts. We became one of the world's top 500 most popular websites for an instant in time! 

However, we were blind to the sad reality: despite our reach, customers (retailers and manufacturers) weren’t signing up. Forget profits; even our revenues were less than $500k. A pittance compared to what was invested.

ShoppingList had a traditional marketing strategy. We were in secretive “stealth mode” and didn’t talk about ourselves without employing a legalistic NDA before launch. While engineering was furiously coding up the site, marketing was just as frantically staking out our positioning and lining up advertising campaigns and PR interviews. 

This traditional strategy may have had a ghost of a chance if we, in post-dotcom parlance, already achieved Product Market Fit. But of course, as a brand new startup, our product wasn’t what customers wanted in all different kinds of ways. Our engineering and marketing teams were toiling for months to an idealized product vision. And because we never really questioned that the product vision was flawed, we hired many good folks and spent millions of dollars only to find out that oops, what we imagined wasn’t real.

It wasn’t just the expenses. The easiest way to motivate and coordinate tens of people working on a project is to have a shared vision and plan. If a plan changes every day, folks naturally get frustrated. So, riding high on dotcom fumes, we were basically aping big company practices without big company profits to sustain us. Of course, we were doomed!

It was only years later, with the benefit of perspective and reading other more perceptive founders like Steve Blank and Eric “Lean Startup” Ries that I came to realize there were better and more fun ways to start Internet businesses for way less money!

In 4-6 months, this is what we did at ShoppingList:

But nowadays, this is what we do:

Today, at Next Small Things, we start with a small idea, doable by just 2 of us in a few weeks. It’s the exact opposite of raising millions of dollars, hiring a big team, and having a fixed plan approved by an official board of directors! The launch of the product is just the start, we try to improve the product every day with two guiding questions: 1) is this what users want? 2) how do we get more users?

The first question has become conventional wisdom and I don’t have much to add. It’s in trying to answer the second question that we have had a few unique successes. 

The Internet is the first read-write mass medium. Business schools still have not quite caught up to the fact that customers/users/readers can talk to each other in real time while using your product! 

Every user interaction can thus be a chance to create a virtual billboard with your product. Often, it’s a billboard for something users themselves want to publicize (to each other) but your service gets a free mention for helping put up the billboard.

From this lens, you can see there is a thread to some of the most successful services on the Internet. When you imagine a video, do you also see the iconic YouTube play button? Did Facebook’s Like button become even more memorable than its logo? 

When user interface designers decry, “you are putting lipstick on a pig”, it’s because they are expected to doll up a product after it’s already been coded. User experience is best designed when each workflow is just being crafted. It’s sorta the same logic for building an audience. If we apply this “billboard” lens for every user interaction in our product as they are being designed, it’s easier to come up with engaging ways your users can help publicize your product for you, all the while doing what they want to get done on your product!

Our own @ThreadReaderApp invites users to make a request to us publicly on Twitter. We reply with a link to a blog-like article of the tweet thread they want unrolled. But, to us, a key element of the experience is that everyone on Twitter can see our user perform the unroll. It’s an integral part of user experience!

Building an audience is one of the biggest stumbling blocks to starting a successful Internet business. We have found that thinking about distribution at the same time as we are designing and building the product goes a long way to deciding whether to do a project and if we do decide, ensuring the project’s success. 

When I look back at the string of failures and the handful of small successes we have worked at over a decade at Next Small Things, the successful ones all share this sense that we have answered “how do we get more users” well.

There are days when I recollect wistfully about the go-go dotcom days when I believed I could be building the Next Big Thing from merely a brilliant idea, strong ambition, and millions of other people’s money. Then, that familiar uneasiness seeps back in as I recall the anguish of disappointing so many and how I pissed away millions. In a blink, I am brought back to reality and I know the next small thing is a more fulfilling journey.