The Longform Startup

A paradigm shift in the way we measure failure and success.

I’ve spent the last two years running what many people might call a failed startup. We failed to capitalize on our ‘first-to- market’ advantage, we never raised capital, and our user base didn’t grow in 10x multiples, achieving hockey stick or viral growth, leading us to the magical word TRACTION. We did not iterate much on how the product looked and felt to the public. My startup was not and is not a household name for the tech and media community. Most importantly, we failed to create a self-sustaining company where our team could afford to work full time as mission driven founders, focusing on solving the challenge we set out to solve.

But in the midst of this journey, I learned a whole lot about failure, and it feels pretty substantive:

1. Failure is a perception, not a fact or inevitable truth. Shout out to Nietzsche for getting it: “All things are subject to interpretation. Whichever interpretation prevails at a given time is a function of power and not truth.”

2. My previous understanding of failure was unclear; it’s pretty hard to know when it’s happening, and pretty easy to think it’s happening when it’s not.

3. Our general understanding of failure in the technology and media industries might not be very clear either.

Catchpool is still up and attracting thousands of users. We have little to no churn (unsubscribes) on our twice/week emails with five links each. Our invited curators on site go through bouts of sharing, and bouts of silence — kind of like humans do with many other habits. I like to think of our site as the deliciously cooked vegetables on the dinner plate; we don’t always want them, but when we get and leave space for them, we’re generally satisfied, not only by the taste, but also by what they’ve replaced.

So, what happened, and why does it matter to you — the reader?

Catchpool was and is bootstrapped, built by a team working together mostly for free, because we care about solving the same problems, and have grown to know and like each other more and more over the years.

While we explored raising capital, we never “ran the process,” because we saw the market tightening up, and weren’t sure about whether our product as it existed at the time was actually the right product. We didn’t go forth confidently, raising capital based on a heady or pie in the sky vision, with the aim to figure it out later. We were more conservative, mostly because I let the amount of times I was told that “media isn’t investable” or that “our returns would never be large enough to satisfy VCs” inform my beliefs about our potential, both in our product and in myself. But I also believe we had an incredibly smart business adviser, and a great MBA intern that grounded me, both encouraging me to keep building but also keeping it real in regards to our fundraising.

Part of me thought that word of mouth and referral marketing would get us the traction I wanted. Yes, that’s idealistic, but I’ve run a business based on referral before, and the quality of our subscribers and followers continue to this day to delight and surprise me.

The truth is, I was turned off by digital advertising in news media, confused by how data-driven digital marketing and growth hacking worked, and hesitant to use any of my strategic press relationships to get attention for a product I didn’t feel completely confident about.

Also, I had no idea how we would manage quality at scale, if and when we reached it, and quality is pretty much our main driver.

You might be thinking, “if this product was good enough, the users would have shared it organically,” right? Well here’s the thing about Catchpool: We built an experiment, secretly and not so secretly meant to push back on some of the assumptions we’ve made about social interactions and content sharing on the web. We were trying to build a platform that would be a deft response to everything that’s annoying and terrible about a world in which viral, clickbait content dominates. We saw how anxious our feeds made us feel (and as yogis and meditators, we’re very sensitive to this), and said, “Where’s our mindful platform? Where’s the platform that makes us feel like it’s the weekend, and that we can relax, enjoy, and breath while learning?” There has to be a better way to stay engaged in the world, without letting our devices own our attention and overwhelm our time.

So, our mindful approach was to do this: in a world where we’ve always attached likes, numbers of reads/watches/listens, follower counts, and pushed fairly heavily on measuring influence, we built a product with NONE of the numbers. We were tired of the type of quantitative metrics and popularity competitions driving news platforms and social media, and wanted to see if building something different would attract a different type of content consumer and sharer, one who didn’t have the time, interest, or energy to grow their followers on other social platforms, or who felt that those other platforms weren’t for them. A consumer and audience not as focused or excited by validations through likes, reposts, or an increase in followers. Think doctor, lawyer, artist, teacher, i.e. non-early adopters, and folks not in tech or media. Did that user even exist (actually I know they do, and they read the weekend paper — but what about digitally)? And would we be able to get them without gaming or hacking the system?

It turns out, that user is hard to get (they exist, but they’re not so easy to find, and they aren’t as into sharing publicly). It turns out that the mechanisms that created a need for a mindful content platform also ultimately hindered its growth. And as such, without scalable user growth, it seems as if we failed, especially to people who aren’t familiar with our team.

The Opportunity from Failure.

Failure is funny; it’s hard to recognize while it’s happening, but ultimately it’s a huge opportunity for growth. No, not the growth in users I referred to above, but the kind of personal and team growth rarely afforded while a company is “going viral.” Of course I saw all of the articles proliferating across the internet about how failure is powerful, sexy, and sometimes even a necessity. But let’s be real: that doesn’t really internalize until it happens, and you get through the other side, and have that 20/20 hindsight. In the middle of it, it’s a constant battle — and I wasn’t quite sure if it was happening to us.

How does one define failure anyway? Is it simply the opposite of how we determine success in the technology and media world?

“I‘ve not failed. I’ve just found 10,000 ways that won’t work.”

-Thomas Edison

My concept of failure has changed because I’ve realized how we measure failure in tech is generally a belief and judgment, grounded in previous models of understanding, both from society and from one’s own personal experience in the industry. But does that framework really make a better product, or a better company?

This interpretation and framework is used to decide whether or not a product is successful, if a team should keep trying new approaches, execute a pivot, or if they should quit. Somehow I was able to step outside of that framework for long enough so that in the midst of our perceived or real or somewhere-in-between failure, my concept of failure (and ultimate understanding of it) began to change.

Failure is a perception, not a fact or truth. In the same way that many of our beliefs in science are theories, not facts (though they feel like they are inevitable truths), I could argue that the same applies to startups. What if the way we measure success and failure (based on previous successful models, on goals we set for ourselves, on raising capital, traction, and public awareness) is simply perpetuating one system and interpretation, at the same time inhibiting alternative modalities of innovation in the way we build products, community, companies, and ultimately solve problems?

As one of my favorite authors and bloggers, James Clear, wrote in a poignant and inspired post on the dangers of comparison, “we are often terrible judges of our own work.” Though he is an author and creative, I would argue that this extends to entrepreneurship. How are we creating our own paradigm for failure, and how do we put into practice a more effective, less comparison-oriented model to building our products and companies? After all, what we compare ourselves and our companies to are other people’s personal and professional images, not the actual knitty gritty of what’s going on behind the scenes and how they got to where they are. It’s just like social media, where we only see one facet of a life. What I’m most concerned with is this: how is the overuse of comparison inhibiting a resilient technology ecosystem?

What questions could we be asking?

Let me give you a personal example of running into a perspective driven by comparison: last year, we (the Catchpool team) applied to an accelerator and made it to the final round, only to be told that we had “team risk” based on our equity structure which was non-traditional, predicated on the team being salaried and going full time if and when we had more capital.

Today, a year later, we still work together — for free. While I understand where that accelerator was coming from, I believe they succumbed to pattern matching (shout out to Chris Dixon for his post teaching me about it back in 2012). They didn’t ask us why we worked together for free. They didn’t ask us about our relationship outside of work, and how we felt it had grown or developed over the years.

To me, and to Catchpool, the team’s whole relationship in and out of work is the crux of our company ethos. That ethos begets the product. It informs our hunger to keep going, and to pivot, theoretically speaking. No investor yet has asked me about why I think our users still open our emails or share on our site in the absence of social mechanisms. That would be one of my CORE questions, especially after telling them that was our original goal of the whole experiment.

What questions are we forgetting to ask because of pattern matching, and our comparison-centric models of success and failure?

How to navigate the promise and challenge of capital.

Pattern matching wasn’t just a problem in our meetings with that accelerator. It was also ever-present and sometimes detrimental to our team in funding talks, with angels and later stage investors. We often look to the ability to raise outside capital as a great early indicator of a startup team and product’s potential for success; but I found in bootstrapping my own startup, and in witnessing the trajectory of well-funded media startups, that capital as this indicator is hard to believe. Capital, while often necessary, can also be a startup’s enemy — it can force a change of focus and even a change of Mission. It’s dependent on so many other factors besides team and product — like that of pattern matching. Of course, it can be powerful and help solve Problems. But, let’s acknowledge that it’s not always so great, nor easy to raise, even when it seems like such an obvious and important problem is being attacked by a talented, diverse, scrappy, lean, hungry team.

So, we failed get into the one relevant accelerator for us, and we also clearly failed to raise capital. In the midst of this particular adventure, I learned a few things about capital in technology and media:

1. I believe an infusion of outside capital can be incredibly powerful for a small startup, but it can also drive the team towards cash flow positive without the deep understanding of product market fit that often takes time and perspective.

2. It can force a team to make decisions that aren’t in line with their ethos.

3. It can cause a team to come from fear rather than abundance because of investor pressure.

4. It can cause a team to sell rather than raise, and leave a lot of potential and returns on the table.

5. It can cause a team to get so focused on comparison that a tangential and possibly even better opportunity or niche is missed.

I’ve experienced it all firsthand, in working at another startup (that did exit, but not in the way I expected), in working as a journalist, and while watching my friends build companies. And it all definitely informed my beliefs about fundraising. From this experience, I began to think a lot about time and timelines.

About Time.

Here’s what I’ve learned about time throughout my experiment in starting a startup: When we create space for quality, we’re choosing to treat our time with more deliberation. As I’ve written about before with my piece Peak Content, I believe that we actually have the opportunity of a generation to reframe the way we produce, distribute, and consume content. I believe that people don’t feel great about their content habits on the internet. But it’s ultimately all about our time — how we manage it and what we choose to do with it and why. After all, it’s one of the scarce resources that shapes our behavior.

Can we create more space in our lives, not just for quality content and time spent on the internet, but also for failure and for exploration? Would we be able to grow more, both personally and in our businesses? Would having a more longform experience (like that of reading a longer, more substantive article or story) but as applied to building our companies and teams deepen the impact of our products, and create more lasting solutions? While building lean is important, I’m arguing for the longform startup. It can’t be mutually exclusive to balance rapid iteration with time for exploration.

What if investors fueled a little more cash into their startups, expressly for the purpose of experimentation and reflection and a little extra time to fail forward and grow? I’ve learned SO much because we’ve had time. What if 10–20% of the capital a startup takes on is dedicated to experimentation and to a cushion in case what’s supposed to happen doesn’t happen. Would a little more abundance of time literally help entrepreneurs reach new heights, pivot better, build resiliency, and fail less or better?

Could we be so stuck in pattern matching, and in our ways of measuring success in technology and in media, that we’re missing the “forest for the trees?” What if we’re not taking enough time, from a funding perspective, a lessons learned perspective, a team collaboration perspective, or from even a pitch perspective? Without enough time, can we even ask the right question(s) and let those questions have time to do the work?

The problems of pattern matching and time are partially why we’re seeing smart folks argue that your media business will not be saved. It’s why we’re seeing media businesses sell early, or fail earlier than other technology businesses. Yet, aren’t some of the biggest businesses in the world all media businesses now?

Right.

“Change is the essence of life; be willing to surrender what you are for what you could become.”

-Reinhold Niebuhr

In the end, I still love news and media and work in the industry because I believe it’s part of the equation of making sure we strive for an equitable world and a better relationship with our planet. Currently, I’m out to question the assumptions we make on the internet about human behavior. I’m out to push people to question what drives them, to question their personal motivations, search for bias, and to live a life that is both deliberate and delightful, on their own terms. I’m out to help empower people to make choices that make them feel good, inspired, and enlivened. Tall order, eh? Sure, but I’m ordering. And I’m looking forward to failing some more, and growing from the experience, both personally and with my business, because I know now how much there is to be gained, and what there is to experience and subsequently become.

So, even though Catchpool has failed according to the normal measures in the startup world, what didn’t fail was our true experiment — could we build something that people would use without being motivated by the popular motivators? Yes. Could we build something incredibly cheaply and scrappily and delight a small group of people? Yes. Can we do a lot more with the product, and will we? Yes — because we had time.

I’ll close with this: sometimes, giving your product time to organically grow, means you as a founder and team of humans actually have time to organically fail and grow. How deeply are failure, experimentation, time, and growth actually intertwined? I started working on the idea of Catchpool at age 26. I’ve grown and learned a lot in the last three years, and as it turns out, my interests have changed. So has my product leads’ interests, and luckily, they’ve grown in concert. The world has changed. So our product will change. We’re excited about it. REALLY excited.

What if we actually build in more time for teams to grow, not just their product and their audience, but as individuals whilst building their companies? How would our products and our impact on the world change if we allowed great founders and teams the space to mature as individuals and progress together — to have a longform experience? Is that a team you’d like to be on? It’s a team I’m on and let me tell you, it’s good. As my product lead astutely notes, “It’s not investors jobs to fund our personal growth,” but I say there has to be a balance between rapid iteration and product development with authentic growth and orientation towards true purpose and potential — Mission. That’s the longform startup.

I’ll leave you with one of my favorite clichés but also adages…

“With age, comes wisdom.”

It’s in everyone’s best interest to take enough time to grow…to grow in wisdom, to cultivate knowledge from understanding the world through mindful media consumption and technology habits, through human connection, teamwork, empathy, leadership and maybe someday, grow into a real success made all the better by failure. That would be true progress.

As always, if what I have to say resonates with you, feel free to email me at erica at catchpool dotcom, where I respond to most notes.

And, a thankful shout out goes to Lori White, Crystal Chang, Michael Jaconi, and Leslie Berger for the edits and for the patience and love.