Startup Deathblows & Setbacks 🥺

When Elon Musk’s hyper-aggressive persona irritated millions of Twitter users, roughly 400k users sought out Post News

When we broke the news that Post will be shutting down on May 31st, my inbox filled up with questions from friends, family, colleagues, and curious investors. Most conversations were empathetic or inbound-ish in nature, but this one bothered me.

Friend: So what went wrong?
Me: Got 3 weeks and a comfy couch? 🤷

Friend: Couldn’t crack monetization?
Me: Actually we did. Really well too.

Friend: Well, what actually killed the company?
Me: *stares into space*

Their last question deserves a thorough answer, but before I’m able to casually drop truth bombs in a DM, I’ll need to flesh this out in a blog post. So friends, let’s talk about it. Hopefully we’ll learn something along the way.

Post is an impossibly heroic mission to save the fourth estate, launched by an extraordinary team well-versed in journalism, designed to create safe spaces for good faith political discussions around quality journalism & independent content. For many members, it’s a utopian safe space where fellow interwebbers can vibe like neighbors. For others, it’s the only platform to proactively help members build audiences for their content. But today, specifically for my team, Post has morphed into a tremendous source of grief.

This grief is unique to those with ambition; reserved for the wild ones who habitually engage in the relentless pursuit of world-changing dreams. At this stage of grief, we’ve not yet done the work to help ourselves articulate our experiences, so we mutter statements like “we almost had it” while we struggle to let go of the outcomes that will never be. But for those of us who learn from our mistakes, we embrace a renewed measure of self-awareness that demands introspection and rumination. So, in the spirit of therapeutic blogging, let’s talk about the moments that keep us up at night; specifically, the moments where undesired outcomes or unexpected situations present themselves. When these moments hit, I like to label them as either setbacks or deathblows.

Apparently there is a comic hero named Death Blow 😂

Setbacks can be grueling, but we don’t typically describe them as problems we can’t solve. They’re always manageable. Sometimes they’re innocuous and we call them bugs or defects. Other times they’re frightening and we call them blockers or outages. In either case, a team of smart people can always survive a setback. Mount up!

In contrast, a deathblow is more menacing in nature. They tend to create panic within leadership teams, and sometimes they’re easy to spot because you tend to notice when someone has accidentally deleted your production database. But most of the time the only reliable way to detect if you’ve got a deathblow on your hands is to pay attention to expressions of existential fear within your team, and more importantly, to recognize when these fears arise within you.

Unfortunately, most tech folk are only trained to handle setbacks by prescribing neat and tidy little technical solutions that solve a localized problem. Rarely are they trained or incentivized to go the extra mile by assessing how a setback might negatively impact other areas of the business, nor are they afforded extra time to take on that effort. Mature orgs embed extensive risk assessment protocols within the core of their processes, but most startups do not. At Post, our resource constraints forced us to rely mostly on our collective experience spotting deathblows in the wild. All things considered, I believe we did pretty well.

* CUE ROCKY MUSIC *

Startups are a collection of dominoes that must be cared for with every decision.

When Noam and I struggled and failed to convince any publisher to join Post’s earliest micropayment trials in 2021, we chose to believe that it was a temporary setback. When we determined that this event wouldn’t cause all of our dominoes to fall, we made plans to revisit publisher outreach after our platform was live and demonstrable. The following year, we persevered by securing partnerships with 25 of the best A-List publishers on our list, with hundreds more to follow in 2023. Although our initial failure stoked the fire of our existential fears, we took the time we needed to feel confident that it was not a deathblow. Instead we defined it as an early setback that would lead to smart pivots and strong victories. ✅

When we eventually had our first major outage due to (🥁 drumroll) DNS issues, it certainly felt like every domino had fallen clear off the table, but we rebounded quickly and kept the damage to a minimum. Bill and the engineering team understood that this was bound to happen, and cool heads prevailed. We also crafted a system upgrade during our triage that strengthened and stabilized our dominoes for reliability and scale. In this particular moment, expertise and experience prevented a deathblow. Love to see it. ❤️

But it wasn’t always hero ball. *cue Facts of Life theme song*

When Elon Musk’s hyper-aggressive persona irritated millions of Twitter users into searching for a new app to call home, roughly 400k users sought out Post News for a safe space to land. While that sounds like nothing short of an amazing market opportunity, it was actually our very first real existential threat. At the time we were only 70% of the way through our launch roadmap, with almost all of our critical trust & safety features still making their way through engineering cycles. The Elon exodus came too soon, and we recognized that missing this opportunity could be a catastrophe for the business.

With “if your product doesn’t embarrass you at launch, you waited to long” ringing in our ears, we were essentially forced to decide if we had built enough of a platform to retain some of the inbound users. After reviewing the potential dominoes that could fall from this decision, we made the call to launch early. We built a waiting list to throttle the system, and I began to mentally prepare for the chaotic change in direction that was just hurled upon my company.

Friend: Deathblow averted?
Me: Not exactly. 😬

We wholeheartedly believed that most inbound users would enjoy grabbing a front-row seat to witness Post very-publicly develop the last 30% of our roadmap. To that end, many of them were in fact completely in love with our mission and our service, and those users did become our biggest long-term supporters. Janete (head of product) also did an amazing job of incorporating the feedback that came from users watching us iterate in real time. But many more users experienced a disappointing first impression where expectations weren’t met, and many of those users never returned… despite our best efforts to catch up with (and surpass) Twitter’s primary feature set.

When the dust settled, Post leadership met to decide if we had just experienced an indisputable deathblow. We began to assess the domino effect. On the one hand, we didn’t really know if we’d blown the only chance we’d ever have at converting Twitter users in large chunks. (Spoiler: despite being the largest exodus, it wasn’t the only one). On the other hand, we were fortunate enough to have gained a large number of wildly enthusiastic users. Those users invited more users, and we did experience a meaningful level of launch growth. With crowd noise subsiding and a clear roadmap ahead of us, we felt like the moment had given us enough to bet on our future. It wasn’t a deathblow, but it certainly was one of our most significant setbacks.

In hindsight, the truest impact of our frantic exodus-launch is that it slowed us down and made it difficult to be both fast and great at delivering software. The unscheduled burden of managing a vibrant community forced us to mature earlier in our roadmap than we’d planned for; but our team adapted and gelled through constant and sometimes-tumultuous process changes. These changes eventually gave us the workflows we needed to juggle extraordinary startup chaos while continuing our pursuit of fast and furious software development.

In truth, it’s tempting to suggest that we did have a deathblow moment. There is an alternate universe where Elon waited another month to begin tweeting at his users, where Post was able to launch with 100% of our features ready to go. But even in that universe, 400k users wouldn’t guarantee growth. In our universe, there were many other internal and external factors that worked against our success; both self-inflicted and beyond our control. My takeaway is that we were blessed to avoid a universe where zero users adopted the platform. That growth allowed us to prove hypotheses and gain knowledge regarding micropayments, AI growth, and a host of other other successful efforts that we will carry with us into our next chapters.

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If you’re in the throws of startup pressure right now, I hope these questions serve as a guide to help you detect whether or not a deathblow is imminent.

1. Do we know if this problem will cause collateral damage to our brand, customers, or internal services? (What is the scale of the problem?)

2. Do we have the team and resources needed to holistically solve this problem?

3. What happens (at scale) if we ignore this problem?

4. Do we still have the confidence of our investors, stakeholders, and customers?

5. Can we solve this problem without endangering fundraising-related milestones?

6. Can we resolve this problem without eating into runway dedicated to our fundraising timetable?

Stay sharp my friends. Always review the dominoes. Don’t forget! ✌️

— Got a deathblow story? Share in the comments! —