Hey y’all — do you feel like you’re killing it?
You know what I mean.
Crushing life. Living the dream. Or at least on your way there?
We become founders because we have a goal, a mission, or an otherwise motivating force to become, achieve, or accomplish something.
How we define success, though, can differ greatly.
This week’s issue is about a conversation at a dinner I had a few weeks ago, and why “killing it” isn’t actually a destination at all.
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Who’s Killing It?
A few weeks ago I had dinner with three founder friends.
All four of us were living very different founder lives:
One friend had exited his first startup and was spending a bunch of time with his family but concerned about finding his next defensible idea in our new LLM-powered world
Another had raised venture and was leaning into growth after a few years of grinding on product
The other had multiple past exits and was considering selling his current company but wasn’t sure if he’d be able to due to AI’s impact on SaaS
And I’ve built a little bootstrapped, cashflowing holdco and previously going the venture route
This isn’t to compare our four situations.
Objectively, all four of us have had some level of success but are still hungry to build and none of us had felt like we “made it” to the degree we eventually want to.
Most of our thoughts around that were rooted in a mix of personal ambition and wanting to provide more for our families.
As we talked, we realized we all felt that way, and it brought up an interesting question:
Since each of us didn’t think we ourselves were "killing it” like that, who did we think was?
These didn’t need to be people we personally know, because you never really know what’s going on in someone’s life, but the question was asking whose life seemed to be the epitome of what we would aspire to ourselves.
The answers were all over the map.
The friend who raised venture said the exited founder who was spending more time at home was killing it.
The exited founder said the multi-time exited founder was killing it.
Etc etc.
But after the initial back-patting, we really started to think about it.
What life do you want to build?
Is grinding on your business a means to an end, or the end in and of itself?
Some names started to come up.
One person mentioned a decacorn founder he knew who was legitimately changing the world while still having a family at home. The scale of his success was appealing.
Another mentioned a couple who lived in their boat with their kids in the Caribbean all year round and made money as influencers. The freedom and relaxed lifestyle was appealing.
And a third person mentioned that it might actually be the person working a 9-5 with no broader ambition (unlike founders, who can’t turn it off). Ignorance can be bliss.
And another one was an indie hacker who makes $50k MRR from a cabin in the woods and calls it a day, working 10 hours a week.
No universal truth came out of this dinner, but we laughed at how subjective it all was. Each “killing it” scenario mirrored what the others were missing.
I share this with y’all because the real insight is that what we aspire to isn’t a fixed destination at all. There is no universal truth here, in actuality.
Success is a moving target shaped by our values, needs, and what we’re missing ourselves.
Don’t try to emulate someone else’s life in the first place. Look at what lights you up and keeps you going on the hard days, and optimize for that future, just for yourself.
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