VCs aren’t interested in a lifestyle business throwing them maybe a small dividend and a miniscule number of companies go public. Look at YC, they have invested in thousands of companies and only around 20 have gone public and only 3 have had positive returns since going public

https://medium.com/@Arakunrin/the-post-ipo-performance-of-y-...

Your identity is tightly fused with the company -- You speak about the company as your primary source of meaning, energy, and long-term purpose. -- Life outside the company is framed as something that would quickly feel empty or boring for you.

You retain control under the banner of high standards -- The VP of Engineering search stalled because no candidate met a bar that is implicitly shaped by how you think, operate, and decide. -- When leverage through delegation feels risky, responsibility naturally flows back to you.

You are the center of cultural gravity -- Culture, values, language, and priorities are largely authored and reinforced by you personally. -- Much of the organization's shared meaning still routes through your judgment and voice.

You delegate execution, but not full ownership -- Even when you are not directly involved, successes are framed as outcomes of foundations you previously built. -- This keeps you psychologically present in nearly every major win.

You created a parallel structure that still depends on you -- OCTO exists to do zero-to-one work, unblock hard problems, and pursue opportunistic bets. -- By design, it reports directly to you and sits outside normal org constraints, reinforcing dependence on your judgment.

You remain the default DRI for existential issues -- Reliability, support breakdowns, reorgs, executive hiring, culture, and innovation still escalate to you. -- This conflicts with the principle you explicitly endorse: if there is no DRI, don’t expect it to get done.

You have not made yourself truly replaceable -- There is no clear path for a future CTO with comparable scope, authority, and trust. -- The role, as it exists today, is inseparable from you.

Your personal fulfillment shapes strategic decisions -- The decision not to sell is framed largely through your motivation, energy, and desire to keep building. -- The company functions as a long-term vehicle for self-actualization now that financial stress is gone.

If this remains unchanged, the long-term risks are predictable: -- Senior leaders will eventually hit a ceiling. -- Innovation will bottleneck on your bandwidth. -- Strong leaders may leave quietly in search of real ownership. -- Succession becomes a deferred crisis rather than a designed transition.

Here are questions I would ask if I were on your board.

1. If you stepped away for six months, what would actually break? not emotionally, but operationally?

2. Which decisions still require your involvement today that should not? and why haven’t you let them go?

3. Is there any executive role at this company you could fully replace yourself in right now? If not, what does that say about how you’ve built the org?

4. Are you rejecting executive candidates because they’re weak or because they would force you to change how you operate?

5. What critical work only exists because it still routes through you?

6. Is OCTO a temporary incubator or a permanent workaround for your inability to decentralize zero-to-one work?

7. How many senior leaders are truly accountable without needing your implicit approval?

8. Are you optimizing this company for scale or for a version of the future where you still feel indispensable?

9. What would have to be true for selling the company to be the responsible decision, not the exciting one?

10. If the company needed you to be less central in order to become great, could you accept that?

It is like these people are hell bound to the work culture, diehard workaholics. They don't know anything else outside of a computer screen.

Honestly disgracefully.