Don't Quit Before the Number
Everyone has a certain number of startups they need to start before one works — your only job is not quitting before you reach it.
- Difficulty
- Moderate
- Time to result
- ~ongoing to results
- Steps
- 4
- Confidence
- 85%
After founding six companies that each generated some revenue but never became a real success, Cortland Allen realized that failure isn't really caused by market size, funding, or timing — those are just obstacles. What actually kills a founder's chances is quitting the overall journey. His model treats startup success as a fixed but unknown 'number' of attempts; some people need only one, others need dozens (his own number was seven, with Indie Hackers). The framework reframes persistence: rather than trying to force any single idea to work, structure your life (frugal living, contract work, enjoying the process) so you can keep making attempts indefinitely without being forced to stop.
Origin
Allen coined this after his seventh company, Indie Hackers, finally succeeded — realizing in hindsight that the first six 'failures' were never really failures, just steps toward the number that worked.
Core principles
- 01Market, funding, and product obstacles don't end your journey — quitting does.
- 02You cannot know your 'number' in advance, so the only reliable strategy is persistence.
- 03Structure your life (savings, contract work, low overhead) to make it easy not to quit.
- 04Treat the process itself as worth enjoying, not just a means to an end.
How to run it
- 1
Reframe obstacles as terrain, not stop signs
Treat a too-small market, running out of money, or a slow build as an obstacle to route around, not a reason to abandon the overall journey.
- 2
Build a runway that lets you keep going
Live frugally and take on contract work when needed so a single failed company doesn't force you out of the game entirely.
- 3
Close individual companies without quitting the path
When an idea clearly isn't working, shut it down deliberately, but treat it as ending one attempt, not ending your entrepreneurial journey.
Pro tip Ask 'am I quitting this company or quitting my path?' before walking away.
Watch out Confusing 'this idea failed' with 'I should stop trying' is the single biggest reason people never reach their number.
- 4
Optimize for learning and enjoyment along the way
Treat each attempt as a chance to build skills and relationships, not just a bet to win or lose, so the multi-year process stays sustainable.
In the wild
Allen started and eventually shut down six different companies over roughly seven years, each earning a little revenue but never becoming a real business, before Indie Hackers — his seventh attempt — finally worked.
→ Indie Hackers was later acquired by Stripe and grew 100x in three years.
Common mistakes
Treating a closed company as personal failure
Viewing the end of one startup as the end of the entrepreneurial journey, rather than one data point on the way to the eventual working idea.
Grinding without enjoying the process
Allen describes years where he coded nonstop with no fun or learning outside the goal, which wasted time and nearly caused burnout without producing success.
Is it for you?
Best for
Repeat founders and bootstrappers facing early failed attempts who need a durable, long-horizon mindset.
Not ideal for
Situations requiring a fast, single make-or-break decision, such as a heavily funded venture with a fixed runway and investor deadline.
From the transcript
“even if you do quit a particular company, like I've quit lots of different companies, but like as long as you don't quit your overall…”
From the episode
Special: Acquired x Indie Hackers