Concepts / Transitioning from a Failed Startup to

Transitioning from a Failed Startup to

The source recommends picking three vertical AI startups whose product you most respect and applying directly to each founder

  • Programming

The Question Behind Your Outreach

A founder who wants to move into an AI startup role often assumes the usual route is to send an application through a recruiter. This article looks at a different path that the source recommends. As you read, keep one question in mind: when you want to reach an AI startup founder, who should you contact, and how should you contact them?

The source makes two linked points. The first is about the route: skip the middle party and go straight to the founder. The second is about the role itself: moving from founder to the FDE role is not subtle, so the preparation for that move has to be deliberate. The sections below take each point in turn and trace how the decision plays out.

Tracing the Two Routes to a Founder

Think of an application as a message that has to travel from you to a decision-maker. The number of hands it passes through determines how much of your story survives the trip. The source describes two possible routes and makes the difference between them concrete.

What do you think happens?

Before looking at the diagram, how many steps lie between you and the founder when you apply directly?

  • Zero steps

  • One step

  • Two steps

  • It depends on the company

Reveal answer
Answer:

One step

A direct application has one step: you reach the founder. The recruiter route inserts a middle party between you and the founder, which adds a step.

YouYour applicationYouYour applicationFounderDecides on your storyRecruiterMiddle partyFounderReceives it second-handone stepfirst handsecond hand
How does the path differ when you apply directly to a founder compared with applying through a recruiter? Each column is one route, and the arrows show every hand the application passes through.

The diagram shows the source's reasoning in structure. On the direct route there is a single link, from you to the founder. On the recruiter route the message must pass through a middle party before it reaches the founder. The source advises skipping that middle party because founders know what your story is worth. The source does not describe the recruiter's mechanics in detail, so the lesson is the step count and the advice that follows from it, not any claim about how recruiters behave.

Choosing Three Vertical AI Startups

The source gives a concrete starting method: pick three vertical AI startups whose product you most respect, then apply directly to the founder of each one. The method is selective by design. You are not asked to send applications to every AI company you can find. You are asked to start with a short list of products you genuinely admire.

Why the Role Shift Is Not Subtle

The second idea in the source concerns the role transition itself. The source says that the translation from founder to the FDE role is not subtle. A founder's experience does not map cleanly onto the expectations of that role. Because the gap is real, the source says preparation has to be deliberate rather than assumed.

This matters because a founder may assume that running a company is itself the qualification. The source does not say that founder experience is irrelevant. It says that the experience must be read against the target role, and that the reading has to be done on purpose.

Finding the Gaps in Your Founder Profile

The source gives a specific method for preparation: read the book again with the target role in mind, so that you can identify the gaps in the standard founder profile. This is the second of the two actions the source names. It asks you to reread material you already know, but with a different question. Instead of asking what the book teaches about founding a company, you ask where your founder profile falls short of what the target role expects.

Before

Question: what does this chapter teach me about building my company?

Reading the book as a founder, asking what it teaches about running a company.

After

Question: where does my founder profile fall short of the FDE role this chapter points toward?

Reading the same book for the target FDE role, asking where a founder profile falls short of that role's expectations.

The source also says these gaps must be addressed explicitly. A gap you have not named is one you cannot prepare for, and a standard founder profile carries gaps by default when it moves into a different role. Naming each gap gives you something concrete to prepare against before the interview process, and something concrete to speak to during it. The source does not list the stages of any interview loop, so this article does not describe them. The point is that the gaps you identified in your reading should be the ones you address directly.

Mistakes Candidates Make With Outreach

  • Common mistake

    Defaulting to a recruiter because it is the usual route

    What it looks like

    Sending every application through a middle party without considering the direct route.

    Why it fails

    The source recommends skipping the middle party because founders know what your story is worth.

    Do this instead

    Apply directly to the founder of each chosen startup.

  • Common mistake

    Applying to every AI company you can find

    What it looks like

    Sending applications to a long list of AI startups regardless of how you feel about their products.

    Why it fails

    The source's method is selective by design. It asks you to start with a short list of products you genuinely admire.

    Do this instead

    Narrow the list to three vertical AI startups whose product you most respect.

  • Common mistake

    Assuming founder experience transfers without review

    What it looks like

    Believing that running a startup automatically prepares you for the FDE role.

    Why it fails

    The source says the translation from founder to the FDE role is not subtle, and experience does not map cleanly onto the role's expectations.

    Do this instead

    Reread the book with the target role in mind and identify the gaps in the standard founder profile.

  • Common mistake

    Leaving gaps unnamed when preparing, which makes them harder to address when they come up

Applying the Method to Your Own Plan

MEDIUM

Write down ten AI startups you know, then apply the source's method. Remove any whose product you do not genuinely respect, keep only vertical AI startups, and choose three. For each of the three, write one sentence explaining why you respect the product and one sentence naming a gap in your founder profile that the target role would expose.

Hints
  • The source's selection is driven by product respect first, so start by removing products you do not admire.
  • A gap is any place where your founder experience does not map onto what the target FDE role expects. The source asks you to find these by rereading the book with the role in mind.
  • Keep the three chosen startups fixed in your notes so you can plan a direct application to each founder.

Key Takeaways

  • The source recommends applying directly to the founder of each target AI startup, because the recruiter route inserts a middle party and founders know what your story is worth.
  • Start with a selective list: pick three vertical AI startups whose product you most respect, and apply directly to each founder.
  • The move from founder to the FDE role is not subtle, so preparation has to be deliberate rather than assumed.
  • Reread the book with the target role in mind to identify the gaps in the standard founder profile, and address those gaps explicitly.