If you want more like this, I share deeper breakdowns on my Substack.
In this episode of Non-Founder Crew, I’m breaking down one of the most overlooked skills in startup careers: how to properly evaluate a startup before you join it.
Most candidates spend interviews answering questions while barely asking any of their own. But joining a startup is an investment of your time, energy, and often your financial future. In this episode, I’ll walk you through the exact questions I believe every startup candidate should ask before accepting an offer.
We’ll cover the core business metrics that actually matter, including ARR, burn rate, runway, churn, CAC, and customer retention, along with what good answers and major red flags sound like in practice.
I also explain why evaluating AI startups requires a completely different lens than traditional SaaS companies. We’ll unpack concepts like inference costs, AI retention challenges, and what creates a real moat in an increasingly commoditized market.
Finally, I break down the equity questions most people forget to ask until it’s too late, helping you better understand what your offer is actually worth before you sign.
Highlights:
(
00:00) Why startup interviews are the wrong way around
(
01:10) Joining a startup is an investment, not just a job
(
02:10) Why evaluating AI startups requires a new playbook
(
03:10) Why most candidates avoid asking hard questions
(
04:10) My experience joining the wrong startup
(
05:00) Why founders should welcome tough questions
(
05:40) When and how to ask these questions in interviews
(
06:20) Question #1: ARR and growth targets
(
06:55) Question #2: Year-over-year growth trajectory
(
07:25) Question #3: Burn rate, runway, and cash in the bank
(
08:20) Question #4: Churn, ACV, and CAC
(
08:50) Question #5: Why customers churn
(
09:20) Question #6: The company’s biggest challenge
(
09:50) Why traditional SaaS metrics fail for AI companies
(
11:00) AI Question #1: Gross margins and inference costs
(
12:30) AI Question #2: Gross retention and the “AI tourist effect.”
(
13:45) AI Question #3: Moats and model commoditization
(
14:45) Understanding startup equity and compensation
(
15:20) Equity basics: Strike price and fair market value
(
15:40) How to evaluate stock options and ownership percentage
(
16:00) ISOs vs NSOs, vesting, and acceleration clauses
(
16:15) The question that reveals how founders think about equity
(
16:40) Why AI startup valuations can make equity risky
(
17:05) How founders respond to your questions matters most
(
18:10) Final thoughts and newsletter signup
Resources: Steal Our Free Interview Question Sheet. Download our Non-Founder Crew sheet for quick access to every question from this episode: From SaaS, AI, to equity and more.
https://bit.ly/3PNCfyk