How to know if the founder is legit?

I'll give my two cents as a founder. It seems like it's a pretty early, pre-product market fit stage startup if they're hiring you as a head of tech. I'll be answering questions based off this assumption.

• They come across as overly confident, almost to the point of being condescending. Is this a common trait among founders, or should it be a red flag?

If they give off bad vibes (condescending like you said), it's likely that they're a bad person OR you aren't a good fit with their personality. If you're going to be head of technology then you'll be working with this person every day. In either case, you're going to have a rough time.

• They strongly believe the product will be successful. I think this is a positive trait for a founder, but I'd like to get your opinions.

I'd say most founders are confident in their product - why would they be pursuing this full-time if they didn't believe in their vision? However, there's a difference between being aware of their weaknesses, knowing what they don't know, and the direction of the company, versus being oblivious to everything bad that happens. I can't really judge which "confident" your founder is - do you think the founder is aware of their competitors, the path to product market fit, what their win conditions/risks are?

• They think all backend jobs will be obsolete in two years due to AI. While speculation is fine, I believe there should be a balance with reasonableness.

• They tend to underestimate the complexity of engineering feats. For example, they think developing services like DynamoDB and S3 was easy for Amazon because of their large workforce, which I find undermines the actual engineering challenges.

I'm lumping these bullets into the same category - the founder doesn't seem technical or is at least technically weak. As mentioned above, you'll likely be working with this guy every day. If he thinks that it's easy to build out large scale infra in a short period, what makes you think that he won't tell you to do the same? Nothing wrong with a nontechnical founder - good nontechnical founders need to be good at sales (which is quite rare). But...

• They talk more about the history of AWS, the life of Elon Musk, and famous quotes rather than focusing on their own product.

If they're talking more about everything else other than their own product, chances are they aren't doing a good job on selling you on the job. If they can't even convince you to think that this will be the next unicorn, what makes you think that they can convince customers to pay for their product?

So unless you're super desperate for a job, I would recommend you decline this offer. The founder seems technically weak and, from what I've seen, is pretty bad at sales. Being good at building and sales are the two main things you need in the early stages of startups.

Onto the next part of your question:

• What aspects should I be looking at?
• What questions should I be asking the founder or team?

There are a few questions like this on Taro that I suggest you look at. Just search "startup" on the search bar. Here's a popular thread you might like:

https://www.jointaro.com/question/UCG4XxyEOTjjyg4pEuwY/how-to-evaluate-a-startup/

I'll add one thing to the list - Ask them about how often they're talking to customers and what customer feedback. If they're not talking to customers enough (like at least 3-5 calls/week) then they're not doing it enough. Early stage startups breath by customer feedback so if they aren't breathing then they're dying.

Early-stage startups require deep trust. Even if the founder is very confident, there's a good chance the company will pivot in a macro or micro way. So your instinct to evaluate the founder (and not the product) is spot on 💯

I'd go so far as to say, if you have no connection to the founder, I would not join. My advice:

• Ask for references on the founder. In the same way that companies may ask for references on you, you should absolutely do the same with the founder. Ask them for folks they've worked with, and also do your own backchannel reference checks. Ask people what the person's strengths and weaknesses were. Would they want to work with them again?
• Startups should be "hell yes" or no. Given the doubts you listed, the default answer should be no. Join if you feel like something is exceptional about this opportunity, or it'll set you up well for what's next.

How can I determine if the startup is likely to succeed?

If you ever figure this out, please tell me so we both do Venture Capital investing and become very, very wealthy 😅💸

What I'd look at is the background/pedigree of the founders. Are they a repeat entrepreneur, with a prior exit? Are they famous in a specific field. If so, their chance of success is much, much higher.

I also put some thoughts in this very popular discussion: How to evaluate a startup?

As a founder, the most important attribute is humility.

This is tricky as founders do indeed need to have confidence: They need to be able to sell a vision to investors, employees, and of course, themselves!

However, there's a difference between being confident and being arrogant.

Humility is critical as what's going to happen with 99% of founders is that their initial idea is going to suck. There's 2 ways this can manifest:

1. The idea is completely off-base and the founder needs to pivot
2. The idea has legs, but the v0 is so janky that it needs to be polished a lot before it can become market-viable

No matter how it sucks, the founder needs to have an open-mind so they can evolve their idea to something worthy of product-market fit. They need to be a feedback sponge, particularly with user feedback.

Many people (including founders) say they're excellent with feedback when they really aren't. I have seen so many product owners get weirdly defensive when they get anything less than a glowing 5 star review.

As a cofounder behind Taro, I'll be the first to say I've been humbled many, many times. Here's a concrete example: Courses. Our users were asking for them both directly and indirectly for almost an entire year. Despite this, we didn't take the feedback too seriously, making excuses because it would take too much effort and there's no $10 billion+ course company. We went on a bunch of random side missions with much worse ideas before finally doing courses. I'm happy that we eventually figured it out, but we were frankly 1 year late with courses.

Going back to the founder you're talking about, it's clear to me the humility isn't there. They are clearly non-technical as they are looking for a "Head of Technology", but they have incredibly strong and extreme technical opinions (that back-end AI one really stands out as I think AI has made back-end engineers more effective, not less). The bare minimum to be humble is to be cognizant of areas you aren't familiar with and be open about that, eager to learn from experts within the space.

What questions should I be asking the founder or team?

This one's easy: "What's the biggest thing you've learned so far working on your startup?"

If 0 humility comes across in their answer, drop them. They should be talking about what mistakes they made, not something like "We realized that investors don't know what a good idea truly is" (I've seen many salty founders say this).