This is all great. One thing I wanted to call out in particular is Thomas' take on investor verbal agreements. YC has a thing about this: it's called the Handshake Protocol.

The idea is: you and your investor agree on (1) an amount to be invested, and (2) a valuation or cap. Maybe you shake hands. Then, after the meeting, you memorialize the deal in an email. The deal is then socially binding: reneging on a Handshake Protocol deal is a big thing, gets noted in Bookface, whatever.

There's nothing magic or even interesting about the protocol; all it does is eliminate a form of ambiguity that professional investors are facile with and founders aren't. Investors are very good at saying "yes" and meaning "no"; they want the option to invest without the commit. If you don't put it to them directly, they'll take the option! The Handshake Protocol puts it to them directly: "are you committing?"

Most of the time, you're going to get a "no" answer to that, which is exactly what you want: clarity, so you can make decisions.

https://www.ycombinator.com/handshake

> there are two separate personas that you need to “create”: The user persona and the buyer persona.

Even more important: stop using personas, start using actual people. I've experienced many startups make unforced errors by conflating people into personas. A better way is to tag people with attributes, such as specific interests, explicit concerns, tasks to be done, usage goals, learning preferences, and the like.

When you switch from personas to actual people, it opens up many more product experiments-- many of which are surprising and may even feel counter-intuitive to founders. Increase your startup chances of success by carefully connecting with your actual users.

I resonate a lot with these reasons. I definitely know I am not the most optimal employee, but often times the people I clash with are people that I cannot respect. Either

- They think they're higher than me (you cannot collab like that)

- They want it their way, despite there being multiple ways to Rome, and will cut off the conversation with orders, not arguments

- They pretend to be technical and are only making the bureaucratic back-and-forth worse. You can definitely tell when someone knows what they're talking about

Sadly a lot of companies will reward these type of people by putting them in the high seats.

I see a pattern where companies end up becoming consulting firms with a bit of proprietary tech. Then all their efforts are put into a handful of clients. The companies call them “design partners” but they’re basically clients.

Seems like a particularly risky trap for bootstrapped companies desperate for revenue. At the same time the best companies I see out there are relentlessly customer focused.

How do you draw the line between “design partner” and becoming someone’s consultant.

Excellent writeup from someone who clearly cares about hitting the intersection of "good for customers, good for himself and investors, and good for employees".

We'd be much better off with people thinking and acting in line with this!

Maybe a simple question I didn’t see here: paying yourself a salary?

How true is it you’ll need to persist under extreme duress unable to pay yourself a salary? Relevant for us with kids / families where we provide the family’s income.

Great article. Few suggestions:

- If you are bootstrapped, you can build dual use technology. - All of this is predicated on the idea that building software is hard, you need 8 years to build a product that people like. Maybe this is all going away in the AI world in a couple of years.

This is really well written and clearly from someone who has loved through it. I think just about all of their observations are correct (except for getting a coach - incredibly detrimental in my experience).

If you have a thing people want that you spent a decade making that isn't easily replicatable, the rest doesn't matter.

If you don't have that, the rest also doesn't matter. Unless you're obsessed with money, in which case, you are very confused and should not be guiding anybody to anything.

Guides regarding minutiae from lottery ticket winners are tiresome. I think anyone over 30 has learned what these 'guides' amount to from looking at Paul Graham.

Great article! One question: you talk about market size, but you don’t address the existing competition in the space. In my opinion, two equally sized markets can have very different levels of competitive pressure.

Is that something you factor into your playbook? Or do you simply not find it relevant to judge whether to enter a certain space?

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why did the author put the tickers for the companies he sold to?