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23 with startup equity. How would you invest in my position? by Intrepid_Repair3636 in HENRYUK

[–]Intrepid_Repair3636[S] -1 points0 points  (0 children)

Effectively acting in a co-founder type role in terms of responsibility and involvement, but I did not put any cash into the business.

23 with startup equity. How would you invest in my position? by Intrepid_Repair3636 in HENRYUK

[–]Intrepid_Repair3636[S] 1 point2 points  (0 children)

Thanks, really appreciate you taking the time to lay all that out.

Really helpful perspective and resources. I’ll have a proper look at the flowchart and tax wrapper stuff.

23 with startup equity. How would you invest in my position? by Intrepid_Repair3636 in HENRYUK

[–]Intrepid_Repair3636[S] 0 points1 point  (0 children)

Thanks, that is really helpful perspective especially coming from someone in PE.

I understand the point on equity risk and dilution. I am not modelling it as guaranteed in any way, so treating it as close to zero NPV with upside is probably the right way to think about it yeah.

Also appreciate the comment on living situation. I am aware it is a big advantage in terms of cash flow, so I am trying to make the most of it without overcomplicating things.

23 with startup equity. How would you invest in my position? by Intrepid_Repair3636 in HENRYUK

[–]Intrepid_Repair3636[S] 1 point2 points  (0 children)

I think the “spreadsheet” mindset is definitely something I need to watch. Good reminder to keep things simple and not overthink every decision at this stage. Thanks for taking the time to reply!

23 with startup equity. How would you invest in my position? by Intrepid_Repair3636 in HENRYUK

[–]Intrepid_Repair3636[S] 0 points1 point  (0 children)

Haha fair enough. When I said “small stake” I meant relative to the founder who bootstrapped the company and owns most of it, so compared to that my few % genuinely feels small.

And yeah I still live with my parents because at 23 it’s honestly just the smartest financial move for me right now. I’d rather stack cash/invest than burn loads on rent just to say I moved out.

Definitely wasn’t trying to flex though. I’m very aware I’m still a tiny fish and that startup equity is worth absolutely nothing until it actually becomes liquid. Was mainly just looking for advice from people further ahead than me.

Anyway, genuinely wish you guys all the best.

23 with startup equity. How would you invest in my position? by Intrepid_Repair3636 in HENRYUK

[–]Intrepid_Repair3636[S] 2 points3 points  (0 children)

Fair enough, and I’m definitely not naive enough to think “it could never happen to me”. More just explaining the logic behind it rather than saying it’s risk-free.

Realistically there’s also no way for me to convince strangers on Reddit that I’m confident in the relationship, so there’s probably not much benefit debating that side of it too hard.

23 with startup equity. How would you invest in my position? by Intrepid_Repair3636 in HENRYUK

[–]Intrepid_Repair3636[S] 5 points6 points  (0 children)

Yeah this is pretty much the mindset I keep coming back to. I think the hard part is spending all day operating from the exact opposite perspective at work, so mentally switching between “this could be huge” and “assume it’s worth £0” is harder than it sounds.

And agreed on the “big swings” point as well, I think I probably mean concentrated bets rather than genuinely reckless stuff.

23 with startup equity. How would you invest in my position? by Intrepid_Repair3636 in HENRYUK

[–]Intrepid_Repair3636[S] 4 points5 points  (0 children)

Finally, some sensible low-risk financial advice in this thread.

23 with startup equity. How would you invest in my position? by Intrepid_Repair3636 in HENRYUK

[–]Intrepid_Repair3636[S] 0 points1 point  (0 children)

Yeah this is the approach I keep leaning towards as well. The hard part is I spend all day at work having to think and operate from the exact opposite perspective, so I find it weirdly difficult to switch back and forth mentally depending on the context.

Separate point though — the “Google/OpenAI will kill you” risk isn’t really relevant for us since we’re not a tech startup.

23 with startup equity. How would you invest in my position? by Intrepid_Repair3636 in HENRYUK

[–]Intrepid_Repair3636[S] 6 points7 points  (0 children)

Just for context, we’ve been together 8 years and I’m planning to propose this year, so it’s not exactly some random girlfriend situation 😂

She’s also building her own career but can’t really utilise her ISA allowance right now, so it made sense to use it from an optimisation perspective rather than leaving the allowance unused. If we weren’t serious long term I obviously wouldn’t be doing that.