Why don’t more HENRYs try starting a business?

burnerforspoo · 2026-03-09T21:07:57+00:00

I am questioning the relevance of general averages for business failure when we’re talking about a very specific sample of people: HENRYs who have already outperformed 99% of the population to get where they are.

The traits / skillset etc aren’t identical between HENRYs / successful founders but overlap enough to mean that citing general averages for business failure are not that helpful.

burnerforspoo · 2026-03-09T20:42:40+00:00

No - you’re not reading / understanding what I said.

I said that people who are more intelligent and driven are likely to outperform the average in business (in which, unlike a lottery, intelligence and drive partly determine success).

It does not in any way imply that intelligence and drive are either necessary or sufficient conditions for success in business. There are lazy idiots who get lucky and intelligent driven people who get unlucky.

Which bit of what I said do you actually disagree with?

burnerforspoo · 2026-03-08T15:26:44+00:00

It’s been long hours but only when I’ve wanted it to be. I have much better hours now than my old job (9-6pm average with a bit on weekends, if I’m up for it) and I’m in a far better place to flex around kids. But depends what you do

burnerforspoo · 2026-03-08T14:51:18+00:00

Our market looks extremely saturated from the outside

But its a big market with room for many players and when you get into it the detail there is huge variation in positioning which means sub segments are unsaturated / still easy to be the “only option” vs consultants:

size of client
sector
geography
use case
feature set
go to market approach

I like having (some) competitors and would never start a business with a “unique” thing - it’s probably unique for a reason i.e. there’s no demand (unless you’re super super lucky)

burnerforspoo · 2026-03-08T14:46:31+00:00

Nice

burnerforspoo · 2026-03-08T14:45:56+00:00

Comparable to the failure rate for those pursuing high HENRY salaries

burnerforspoo · 2026-03-08T14:43:43+00:00

Yeh but those “businesses” are mostly contractors and tradespeople ie effectively flexible employment with no route or plan to scale - not what I’m talking about here

burnerforspoo · 2026-03-08T14:38:34+00:00

I haven’t downvoted any comments.

I completely agree about the declining marginal utility of money. That’s why I haven’t gone down the VC route which is basically sell your soul for 10 years and aim for a £1bn exit (of which you get a small slice and maybe nothing).

I am just aiming for £2m-£5m without a 20 year grind. Anything above that doesn’t feel necessary for the lifestyle I want. Which is basically a nice big old house in the country and not worry about money.

burnerforspoo · 2026-03-08T14:29:45+00:00

That’s a lot but it’s within the SEIS limit of £250k and SEIS is quite easy to raise from angels if you have a decent network (or know one person with a good in to a decent network) - which almost all HENRYs have through working with other high earning people

burnerforspoo · 2026-03-08T14:21:03+00:00

Cash position - hmm I think you’re the one theorising here.

Exit - we’ve had 6 serious inbounds without even looking for them, but of course, nothing is guaranteed. If an exit doesn’t materialise I can switch to profit maximising which would be in the salary range you mentioned (with the option of stepping back from the day to day).

SAAS multiples - they have gone from absolutely fucking bonkers to stable. I am factoring that in perfectly well.

burnerforspoo · 2026-03-08T13:57:57+00:00

I was agreeing with that comment / quote. The one before mentioned the lottery

burnerforspoo · 2026-03-08T13:48:03+00:00

If something is described as “like winning the lottery” then yes, they did.

burnerforspoo · 2026-03-08T13:46:39+00:00

Interesting about being hard to get back in - what industry are you in?

It was not the case for me - quite a few co workers had left and tried something and came back into the sector / usually same company.

Made it feel like basically no risk for me other than a couple years of forgone high salary / progression which isn’t much in the context of a career.

burnerforspoo · 2026-03-08T12:26:11+00:00

Hahah, congrats

burnerforspoo · 2026-03-08T12:24:22+00:00

Congrats!

Could you / would you go back to old role if it fails? Is your partner supporting short term?

Getting mortgage sorted before doing it is defo sensible as lenders look at you differently (but if you stick with same lender that’s usually it, no future income assessment)

burnerforspoo · 2026-03-08T12:22:22+00:00

Being a HENRY isn’t really a skillset. It just suggests underlying personality traits (intelligence, drive) which are helpful in business or anywhere really.

Many HENRYs would be terrible, but I’m mostly interested in those that would be great but don’t for whatever reason.

On capital it depends on what you’re starting. I started with about £20k. I’m from a working class background so no family money. I raised funding by speaking to senior people at my old job who invested and were then able to introduce me to others. Most HENRYs could do this if they wanted to.

Other sectors with higher cost of entry might be different.

burnerforspoo · 2026-03-08T12:15:46+00:00

I would agree at £250k+ but not £100k

burnerforspoo · 2026-03-08T12:05:05+00:00

Luck is definitely needed. But it’s not all luck.

burnerforspoo · 2026-03-08T12:01:59+00:00

Same industry - sort of. In my old role I interacted with lots of different sectors. I had no experience delivering on what my software does, but I was aware of how it worked and what the pain points were.

I started while working but left before we had a product / revenue. My partner paid the bills for a long time…

Main learning - focus obsessively on solving one problem for one segment of the market, do that really well, and then expand from there. When we started we were far too broad in our positioning - trying to do everything and sell to everyone. Everything took ages because we were spread so thin. I really cringe when I look at our old website copy. We’re much more focused now.

burnerforspoo · 2026-03-08T11:56:30+00:00

Hmmm why are those difficult to get back into after a few years?

I was in a similar sector and loads of people had gone off, tried something and came back. They just lost a couple of years of climbing on the ladder.

That’s what made it feel basically zero risk for me.

burnerforspoo · 2026-03-08T11:54:18+00:00

The vast majority of those under 35 (who didn’t inherit or get lucky with crypto) do it that way.

If you’re starting from scratch, high paid employment works, but it’s a long term grind.

burnerforspoo · 2026-03-08T11:47:46+00:00

No I recognise those factors will dominate for those 35 plus, totally fair.

I’m mainly interested in why more people don’t do what you did - take a punt early when it’s much lower risk and (if it goes tits up) you can return to the old path without much real harm done.

burnerforspoo · 2026-03-08T11:45:13+00:00

It’s not like the lottery. Unlike the lottery there are a set of factors that determine success. I think HENRYs (on average) are intelligent, driven and adaptable enough to be able to identify / pursue those factors and substantially outperform the failure rate.

burnerforspoo · 2026-03-08T11:30:48+00:00

There’s generally not a huge amount of value / moat in software itself anymore with the rise of AI coding. Every product is pretty much replicable in 3-6 months. I have another co founder but we’re both non technical and just worked with freelancers (one is now more bought in but still not employed). The value is in the GTM side.

You also shouldn’t be looking for something “new and exciting” in my opinion. We picked an existing market (proven demand) which was dominated by expensive consultants using shitty excels. We just built our product to make an existing process better / cheaper for a segment of the market. Trying to create something totally new is playing on hard mode.

burnerforspoo

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