What would you do: iterate on the problem or switch the customer segment

This is a tough one.

Firstly, congrats on being so self-aware. Based on that (and your focus on the problem over the solution) you're easily in the top 2% of IHers most likely to build a successful business .

Early stage startups/founders are terrible customers. Truly terrible. They need a lot of customer service and handholding, but can't afford to pay much and churn quickly.

Yet when it comes to enterprise/established companies, you seem pretty certain that you don't have the enthusiasm/passion necessary to build the business and make sales.

If you think that now, then you're almost 100% guaranteed to be correct.

I'd also be very wary of iterating around the product instead of the problem. If the square peg doesn't fit in the round hole, go build a different peg, don't wander off hoping to find a square hole.

My advice for your situation would be to spend more time with founders/early stage startups and see what problems they are willing to spend money on solving. Don't get tricked by the sunk cost fallacy.

Another approach would be to talk to high-growth startups/small businesses and see if they have the problem you're passionate about solving and have been working on already. Sales to them will be much closer to 'startup sales' than enterprise sales, so you just might enjoy it.

Good luck!

i don't like enterprises at all. you have to pretend and you can't be yourself and you have to do with a lot of overhead.

I don't know what industry you're in, so you might be totally right here. But I've seen a lot of situations where enterprise sales is downright pleasant. In fact, I'd say the businesses with the most pleasant relationships between the owners and the customers are typically B2B doing sales to a relatively small number of big customers.

I like to use myself as an example here. Doing ad sales for the IH podcast early on was great when I was talking to people at big companies and awful when I was dealing with small startup founders.

The people at big companies worked in departments whose entire purpose was to spend money on ads. Sales were easy and streamlined. They just wanted to get on the phone and talk about their kids and vacations. They often renewed and rarely checked in. Whereas startup founders were tough to sell to, super cheap, and checked in constantly to see if they were getting their money's worth.

If you don't like enterprises at all and want to focus on early startups, you should consider not only the business perspective, but your personal well-being. Would you commit yourself to working on something you don't like? Based on your own answer to that question, then you can act on the other.

You have now an idea that may work, but that wouldn't satisfy you. You can find a way of building a solution keeping in mind a quick exit from your side. For instance, you could transfer the business to someone else and you keep a role of advisor, etc.

Your sentence:

i'm also not sure how much money early stage startups are willing to spend on software as a service

And this sentence:

i'm good at startups. and working with founders. that's what the past has shown

Makes me wonder exactly what your insights on startups are. If you already validated the fact that startups don't spend on SaaS, then you should do something that is not SaaS, perhaps write a book. It wouldn't matter if you try hard to find a problem, you know people won't pay for a SaaS solution to it.

However, I do not agree 100% with your statement. Rational founders pay or not for SaaS services based on the value they deliver. If you have a service that will make me 20% more productive, I can act based on that. New services more often than not fail at proving their own value. Startup SaaS for other startups working on SaaS models start piling up in a circle. Someone needs to generate revenue out of it in order to sustain all the others.

Can you share some more details on why it is not a product for early stage startups?

You might be able to go for the hybrid model, where enterprise customer generate most of the revenues, that allow you to serve the founders. (if this can work).

Also you might want to revisit your view on enterprises, it seems like you had some bad experience there that biases your view. In the end you are selling to people and people in the enterprise need/want help just as much, it is probably only more procedural/long in the sales cycle.

The only advice i can give to you is to take your time and research your unknowns and try to make an objective decision at the point where you feel comfortable with your decision. No one knows your situation better as you do, all other advice could be invalid or irrelevant. Justin Jackson was writing about a somewhat similar situation, when he was about to make a decision, and asked for advice, please read it: https://justinjackson.ca/costs

Good luck!