How do you know a startup is doomed?
some obvious signs
Before we dive into today's story, a quick question:
Have you ever walked into your office (or logged into Zoom), looked around, and thought, “Is this thing... sinking?” Because same.
Today, we’re talking about a topic no one wants to admit out loud, especially not on a company Slack thread: How do you know a startup is doomed?
Not pivoting. Not struggling. DOOMED.
Let’s go…
📌 It always starts with a feeling
This week, I came across a Reddit post that hit way too close to home. A user (with a very relatable level of startup trauma) shared:
"I’m only at my second startup, and the first is still thriving. But I left for a better salary and work-life balance. I don’t really know what it looks like when one goes belly up."
That feeling? That quiet suspicion you don’t want to say out loud?
Others have felt it too, and they’ve shared the warning signs.
Here are some of the most telling.
📌 The ultimate business red flags
Executive exits disguised as “Next chapters”When a company starts announcing that its CFO is “taking a break to focus on family” and the Head of Product is “off to pursue exciting new ventures,” it’s rarely just about family vacations or passion projects.
These phrases are often corporate code for internal shakeups, strategy pivots, or declining performance.
One exec leaving might be a coincidence. Two or more within a short time? That’s a signal.
It often means leadership has lost confidence, a boardroom battle just ended, or the company is quietly bracing for a downturn.
For employees, it’s a cue to start reading between the lines, assessing team morale, and maybe polishing up that résumé. Publicly, the messaging stays rosy, but behind the scenes, the real story is unfolding fast.
Sudden silence about winsA sudden hush in internal communications is never a good sign.
If your CEO once celebrated every client win or product milestone but now skips over key metrics like monthly revenue or growth numbers, there’s a reason, and it’s rarely good.
Leadership tends to amplify success to boost morale and investor confidence. So when the usual hype around wins vanishes, it might indicate a dry spell, missed targets, or deeper financial trouble.
One Redditor put it bluntly: “If they’re not shouting about success, it means there isn’t any.”
Companies don’t go quiet when things are going great, they go quiet when there’s damage control underway.
This silence, especially during all-hands or town halls, can be the calm before the storm, like layoffs, funding issues, or worse.
Always listen closely, not just to what’s being said, but to what’s being left out.
No birthdays or offsitesFirst, it’s the little things: cancelled offsites, no more birthday celebrations, travel restrictions, and a quiet goodbye to bonuses.
Suddenly, the energy shifts.
Perks that once reflected a company’s appreciation begin to vanish without explanation.
Then comes the flood of all-hands meetings filled with vague motivational speeches about “weathering the storm” and “finding strength in adversity.” It starts to feel less like inspiration and more like damage control.
When a company replaces tangible support with constant morale-boosting monologues, it’s not just a budget issue, it’s a cultural red flag. It signals that leadership may be struggling behind the scenes, and rather than being transparent, they’re opting for spin.
The product roadmap seems too good to be trueWhen product teams parade flashy roadmaps filled with exciting new features, but none of them ever see the light of day, it's a clear red flag.
If updates are constantly “in progress,” timelines keep shifting, and bugs from six months ago are still haunting users, you’re likely witnessing a product team that's either overwhelmed or directionless.
It usually means deeper issues: poor prioritization, lack of technical resources, or leadership that’s out of touch with execution reality. Sometimes it’s all of the above.
When teams can't ship what they promise and can’t fix what’s broken, it’s not just about delays; it’s about trust. If no one believes in the roadmap anymore, it stops being a tool for alignment and starts becoming a punchline.
So, that’s it for today. If you enjoyed this edition, subscribe to hear from us every day!
And drop what startup red flags you always notice.
See ya 👋
