Ask questions like an investor, think like a founder.
Written by: Richard, Partner at Dragonfly
Translated by: Luffy, Foresight News
If I ever need to look for a job again, I would use this checklist. If you are interviewing at a startup, you should steal this checklist.
Throughout my career, I have been fortunate to hear genuine thoughts from founders, operators, recruiters, interviewers, internal employees, investors, and job seekers. This is the framework I have formed in my mind after listening to various opinions.
1. Founding Team and Structure
Start with "people":
Who are the founders? Do they have successful cases, risk signals, or do they fit the market?
Have they worked together before?
Who are the early employees? Are they complementary to the founders or redundant?
Are there high-caliber advisors or board members?
Ultimately, even if the company undergoes significant changes (which usually happens), you are still betting on "people." Sometimes, it’s not the first idea that succeeds, but the team that makes the idea happen.
2. Funding and Development Path
You are trading time for equity, so know its value:
Is it venture capital-backed or bootstrapped? How long can the funding last?
What stage are they at? Pre-seed? Series A?
Who is on the cap table? Are the investors genuinely helpful, or just tweeting?
When is the next funding round? What’s the plan?
If they cannot provide clear answers, you should not blindly join.
3. Product, Technology, and Progress
What are you actually joining?
What is the real function of the product?
What is currently live vs. concept products?
What is the roadmap for the next 6-12 months?
Tech stack: modern architecture or a patchwork?
Is there user retention or churn data?
Are customers paying? Are there major clients? Or just pilots?
Especially in AI, infrastructure, and crypto, you need them to genuinely solve problems, not just hype and jargon.
4. Market and Growth Potential
Your equity is only valuable when the company grows:
How large is the market size?
What niche are they entering?
What is the go-to-market strategy; product-led growth (PLG), sales-driven, or a hybrid model?
Is there a repeatable growth engine?
Can you see a credible revenue growth path?
A large market without a go-to-market strategy = showboating; ambition without distribution = fantasy; vision without execution = PPT. Choose your favorite.
5. Mission and Alignment
If you join early, it’s best to truly believe:
Can the team clearly articulate an inspiring mission?
Is the vision coherent, or just a pile of buzzwords?
Is the team aligned on the ultimate goal?
You don’t have to "change the world," but you should believe in what you are building.
6. Regulatory and Legal Risks
In fintech, cryptocurrency, health tech, and AI, be particularly aware of regulatory and legal risks.
Are there known or potential regulatory hurdles?
Are they operating in a gray area?
Are there pending legal issues?
A sudden subpoena could turn your "rocket ship" into rubble.
7. Metrics and Focus
Clear metrics create momentum.
What metrics do they track weekly/monthly?
Are they genuinely using data, or just going by gut feeling?
Are they measuring important things, or easy-to-measure things?
Sometimes there are no metrics yet, and that’s okay. But you should still be able to discern what the focus is. Jensen Huang and NVIDIA don’t have formal OKRs; they just build with obsession.
8. Culture and Recruitment
You are not just joining a company; you are joining a team project.
What are the clearly defined and genuinely practiced values?
Is there early employee turnover? Why?
How do they make hiring decisions?
Do you want to learn from these people?
Also, consider: asynchronous or synchronous culture, remote or in-person. If the culture feels toxic or superficial? Trust your instincts.
9. Founder Psychology
When things go off track (which they will), how do they react?
Are they open to feedback, or defensive?
Have they survived failures, or are they just riding the bull market?
Can they attract and retain high-caliber talent?
The best founders are not perfectionists but relentless learners.
10. Risks and Vulnerabilities
No company is invulnerable.
What are the top three survival risks?
Where are the weakest links: technology, market entry, funding, talent?
What is the plan to mitigate risks?
You don’t need to avoid all risks, but you need to be clear about your situation.
11. Talent Attraction
There may be bias, but this could be the most important signal after the founders.
Are they attracting top talent, or just anyone?
Are former employees fans?
Would you bet on this team again?
A strong team gives you room for error, while a weak team magnifies every mistake.
12. The Role Itself
Back to the specific role:
Does this role match your level?
Was it suitable two years ago? Will it still be suitable three years from now?
Is the compensation aligned with the requirements?
Is the job definition clear, or do you need to write the JD from scratch?
Often, early-stage or inexperienced hiring teams only realize what they need when interviewing candidates. Be prepared to adapt to their actual needs, or walk away.
Practical Actions I Will Take Next Time Job Hunting
Background check the founders and hiring managers. Who says only they can do this?
Use the product or request a demo. Would you pay for it? Or who do you think would pay?
If possible, talk to customers and ask about real pain points.
Research the cap table and funding history; what signals can you glean from it?
Search for past podcasts, blog posts, and tweets from the founders and team.
Observe your surroundings; are smart people paying attention to this team?
Dig deeper: GitHub, Twitter, Discord, Farcaster, AMAs.
These actions are not radical; they are informed. The best thing you can do for yourself is to make a fully informed decision.
Final Thoughts
Joining a startup is like writing yourself a check with your time and career. So, ask questions like an investor, think like a founder. Ask the real questions, conduct your own due diligence, and make informed choices rather than emotional ones.
Work is a transaction, and a career is a portfolio; choose wisely.
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