How to evaluate a startup

Tony's Guide to Startup Evaluation

I was job hunting this year and I really liked Tony's writeup about heuristics to evaluate a startup with. Here's the tldr;

For early-stage, look at Team
For mid-stage, look at Market
For late-stage, look at Growth

Early-stage startups are still looking to find product-market fit, so you should be thinking "how competent is the team and how likely are they to handle change?"

Mid-stage startups have shipped their MVP and what matters now is the quality of the market. This includes

1. Size
2. Is it growing?
3. Unit economics/metrics of the market
4. Capturability and defensibility

Late-stage startups are looking to expand and grow in their market or adjacent ones (think Uber and UberEats, Google and Gmail). At this point, the company's growth is the important metric because it is no longer easy to fake. You can see growth based on Google Trends and LinkedIn (actively & aggressively hiring).

Reverse Interviewing

Gergely Orosz has a great article about reverse interviewing the teams you'll be spending a lot of time with, in which he lays out questions to help engineers learn about their potential teams.

Team-Based

1. What are the last three projects/features you've shipped?
2. What product are you most proud of working on? Why?
3. What is the biggest struggle you have/had at Uber? Why?
4. What are you most excited about for the next six months?
5. Tell me about the team. How would you describe the team dynamics?
6. Assuming I joined, what advice would you give to be successful?
7. What are things that you have seen new joiners struggle with?
8. Has anyone left the team? If so, what was the reason?

Engineering

1. Can you show a non-trivial code review? (look for comments, general vibe, automatic build pipeline deployment, staging environment, tests)
2. What separates a good day from a bad day for you? What tends to cause them?

Business Strategy

• how do you measure progress?
• what are your plans for the next year?
• what is your exit strategy?
• where do you want to be in 5 years

Financial

• runway, burn rate, revenue?
• what are your hiring plans? (runway and equity is completely dependent on this)

WLB and Benefits

• What are your usual working hours?
• What's the PTO/vacation policy?

Compensation

• salary
• equity

Product

• what are your biggest concerns/threats about the business?
• how is it better than competitors

Team

• What's your work methodology? (agile w/ 2 wk sprints, etc.)
• What is mentorship like?