Hey Reader,
The word quit tastes like metal in the mouth. It sounds like failure, but really it’s a dirty word for allocation.
This is not a pep talk or a eulogy, that’s not my job. Mine is just to ask you to hold up a mirror if you’ve stalled, and consider three honest paths:
- Keep Going (Beast Mode): The loops are kinda working. The smoke signals are kinda forming. You are confident this isn’t a delusion issue, the issue is it’s just not fast enough. (the dip)
- Redeploy (New Vehicle): You found the right problem but chose the wrong form. As in, you are 1000% right about the problem you found, but you started solution-first and now need to iterate, pivot, go adjacent, into delivering solution 2.0. (the pivaaaat)
- Clean Quit (Harvest & Hand-Off): Stop now. Preserve value. Move your momentum. It’s time if you can stomach looking like a failure for a week to look smart in a year. I get it, you and your startup are alter egos - it's not designed to be easy.
Whichever path you’re on, wherever you are. Quitting, not quitting, in revenue, doing OK, not doing OK - the point is always recognition and reality. Conscious choice to ignore is much harder.
And just to make clear. If you are heading down that path, it’s not treason, it’s divergence. It’s a different appetite for risk, a different time horizon, a different definition of done, a different season in your life. Shift from an emotional, guilt-ridden feeling of failure to a strategic, intentional act of charting a new course.
Also, if you happen to enjoy my content, would be hugely appreciative if you could pre-order my book.
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Starting A Startup: Build Something People Want
Every founder starts at zero. No one starts with a product, customers, revenue, or a real clue how it will all play out.
Failure is the result of not doing everything in your power to turn your nothing into something. It's that simple.
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This whole topic came from my buddy Jim, who said it pretty perfectly: when it’s time to quit, quit, quit again, and again not because he was suggesting a lack of commitment or resilience, but the opposite. When all the knowledge, insights, learnings, lessons, and network you’ve accumulated on your journey can no longer be accretive to your current journey, you are obligated to find a place to put that value… so go do it versus wasting cycles.
You can name it without assigning moral weight. Own your piece. Own your needs. Own the next decision. It is still all your fault...
The worst founders aren’t the ones who quit. They’re the ones who stayed two years too long defending a thesis they stopped testing…
QUIT MATH....
There is no framework-of-frameworks or binary answer to should you stop. Ish. With enough experience you can look objectively at a business, it's product, price, positioning, unit economics and make a reasonable call on its ability to win - what most angel investors would do when sizing the opportunity.
Sometimes a left-field door opens, some asymmetric moment that changes everything, some merger of luck, timing, signal, and competency to leverage.
But:
There is a massive gap between signal value, as in what the data shows and option value, how you feel and the opportunity for magic to happen.
This framework of quit math is for founders with some traction who are evaluating whether to continue. If you have no customers, or prospects who understand your product clearly but still choose not to buy, that’s a different conversation.
Compounding Signals: Is everything getting a little better or easier or clearer or predictable? Do new people who sign up perform better based on the changes you have made, sales close quicker based on your capabilities, organic or referral inbound starts to trickle in, sales start to happen without heroic moments.
Example: D30 retention increases (as in this month compared to last month more users are still active 30 days after signup, or fewer users are churning within the first 30 days). That’s a signal things are sticking.
Founder Energy: How are you doing? If tomorrow were Day One, would you still choose this problem. Do you still find yourself curious and pulled into the work of making this work (not just dutiful to the story you have told the world).
Runway & Learning Multiple: Are learnings per dollar increasing? (aka are you paying to learn faster or slower?) Is the same burn buying you fewer new truths or same spend but no new learnings (your learning per dollar is falling.)
Market Drift: Is the market moving towards you, or past you? Are there platform/competitor moves that make your wedge less necessary? Are you moving into being a feature not a company? A fun helpful tool, and buyers reclassify you as “nice-to-have.”
Perhaps, if two or more of these cold and you can see a clearly hotter wedge that you could ship in 30–60 days? That’s not quitting. That’s allocation.
Signals are direction, not a vibe. They should get a little more predictable each week. One-off wins don’t count, this is starting to look for some consistency vs anecdotes. If the good news needs a paragraph of context, it’s not a signal yet - that's fine, but that one deal likely doesn't represent the market.
Option value is the only override to unclear or bad signals: as in there’s a near-term door, within weeks, that is a stretch bet, that is going to use a chunk of runway that, if it works, could change something, hopefully everything, ideally on the slope (distribution, data, partner, wedge). And if you already have real pre-commitments vs building off another untested hypothesis as opposed to a last mile prayer pivot, and, if you can name that door, put an owner and a date on it, and you’ll know inside 30–60 days keep going. If not, harvest.
This is a committed distribution partner deal that's more than "we are chatting to stripe" and is instead we are on calendar and in the pipeline. This is a data breakthough that could unlock new utility, such as customers using the platform in a different way that has opened a new use case, or an unlock that transforms something from helpful to automated. This is a pilot where there is a real capability milestone that triggers contract. This is inbound from a buyer you’ve never pitched with real budget who found you.
This is not a warm intro with a “sounds interesting, keep us posted” or a feature you think customers will want based on internal vibes or a theoretical wedge that requires another 3 months of build and a deck to explain.
How could each path look?
If you’re staying in beast mode, you’re not trying to fix your vision. You’re fixing your loops. Pick one thing, one catalyst objective, that unlocks everything else in the next 30 days. Shorten your feedback cycles. More reps, smaller bets. Get out of slack and back to customers. Raise your standards in public, announce the next measurable milestone to your team and your customers.
If you’re redeploying, you keep the same insight but find a new form. Different wedge, different GTM, different buyer. Run a quick customer thread sprint, maybe re-interview your best fits, write down the "jobs to be done" they’re hiring you for, prototype the thing they basically begged you to build. Ship the smallest version that proves commercial intent.
If you’re doing a clean quit, you stop pushing the product and start harvesting value. This is exiting how you want to be remembered. Land your people, handle migrations, do all the work, announce last. Keep your reputation, relationships, and runway intact for whatever comes next - which is the goal. To preserve your founder equity.
If You’re Not Quitting
Good. Keep this as your Threat Model. Write the “Quit Note” you hope you never send. Then reverse-engineer it into goals you do need to hit.
Write the email to your customers, your investors, your employees, your LinkedIn community. What happened, what went wrong, where, how. Predict your own death and then use that as your guide.
...and if you are
Then recognize you failed, sure, but by choice because you finished learning what this vehicle could teach you.
If this is you, and you want some plan or theme to help you quit clean, lmk, I’m working on one.
If I can be of service, feel free to grab time.
LFG.
-- James
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