Dragonfly Talent Partners: Job seeking is investing, a checklist of 12 questions to think like a founder.

Ask questions like an investor, think like a founder.

Written by: Richard, Dragonfly Talent Partner

Compiled by: Luffy, Foresight News

If I need to find a job again, I will use this checklist. If you are interviewing at a startup, you should steal this checklist.

In my career, I have been fortunate to hear the genuine thoughts from various people, including founders, operators, recruiters, interviewers, internal staff, investors, and job seekers. This is the framework I formed in my mind after listening to the opinions of different parties.

1. Founding Team and Structure

Start with "person":

• Who is the founder? Are there any successful cases, risk signals, or does the founder fit the market?
• Have they worked together before?
• Who are the early employees? Are they a complement to the founders or a duplication?
• Are there high-level advisors or board members?

Ultimately, even if the company undergoes significant changes (which usually happen), you are still betting on "people." Sometimes it's not the first idea that succeeds, but the team that makes the idea happen.

2. Capital and Development Path

You are exchanging time for equity, and you need to understand its value:

• Is it backed by venture capital or bootstrapped? How long can the funding last?
• What stage are we in? Pre-seed? Series A?
• Who is on the equity structure chart? Are the investors truly providing help, or are they just tweeting?
• When is the next round of financing? What is the plan?

If they cannot provide a clear answer, you should not blindly join.

3. Products, Technology, and Progress

What are you actually joining?

• What is the real function of the product?
• Currently launched content vs conceptual products?
• What is the roadmap for the next 6-12 months?
• Tech Stack: Modern Architecture or Temporary Patchwork?
• Is there user retention or churn data?
• Is the customer paying? Are there big clients? Or is it just a pilot?

Especially in AI, infrastructure, and the cryptocurrency space, you need them to genuinely solve problems, rather than 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 market are they entering?
• What is the market entry strategy; product-led growth (PLG), sales-driven, or a hybrid model?
• Is there a repeatable growth engine?
• Can you see a reliable income growth path?

No market entry strategy = show; having ambition without distribution = fantasy; having vision without execution = PPT. Choose your favorite.

5. Mission and Coordination

If you joined early, it's best to really believe:

• Can the team clearly articulate an inspiring mission?
• Is the vision coherent or just a collection of buzzwords?
• Is the team aligned on the final goal?

You don't have to "change the world," but you should believe in what you are building.

6. Regulatory and Legal Risks

In the fields of fintech, cryptocurrency, medical technology, and AI, it is particularly important to pay attention to regulatory and legal risks.

• Are there any known or potential regulatory obstacles?
• Is it operating in a gray area?
• Are there any pending legal issues?

A sudden subpoena might turn your "rocket ship" into ruins.

7. Indicators and Focus

Clear motivation for creation.

• What metrics do they track weekly / monthly?
• Is it truly based on data, or just a feeling?
• Is it measuring something important or something easy to measure?

Sometimes there are no indicators, and that's okay. But you should still be able to discern what the focus is. Jensen Huang and NVIDIA do not have formal OKRs; they are simply building with obsession.

8. Culture and Recruitment

You are not just joining a company; you are also joining a team project.

• What are the clearly defined and truly practiced values?
• Is there early personnel turnover? Why?
• How do they make hiring decisions?
• Do you want to learn from these people?

Additionally, consider: asynchronous or synchronous culture, remote or offline. If you feel the culture is harmful or superficial? Trust your instincts.

9. Founder's Mindset

How will they react when things go off course (which will definitely happen)?

• Are they open to suggestions, or are they defensive?
• Did they survive from failure, or are they just riding the wave of the bull market?
• Can they attract and retain high-quality talent?

The best founders are not perfectionists, but relentless learners.

10. Risks and Vulnerabilities

No company is invincible.

• What are the top three survival risks?
• Where are the weakest links: technology, market entry, funding, talent?
• What is the plan to reduce risk?

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 founder.

• Are they attracting talented individuals or just anyone?
• Are former employees still fans?
• Will you bet on this team again?

A strong team will give you room for error, while a weak team will magnify every mistake.

12. The Role Itself

Return to the specific role:

• Does this role match your level?
• Is it suitable two years ago? Will it still be suitable three years later?
• Are the compensation and requirements consistent?
• Is the job definition clear, or do you still need to write the JD from scratch?

Typically, early / inexperienced hiring teams only realize what they need when interviewing candidates. Be prepared to adapt to their actual needs or walk away.

The practical actions I will take for my next job search

• Background checks on founders and hiring managers. Who says only they can do this?
• Use the product or request a demonstration. Would you pay for it? Or do you think someone else would pay?
• If possible, talk to the clients and ask about their real pain points.
• Study the equity structure table and financing history; what signals can be seen from it?
• Search for past podcasts, blog posts, and tweets from founders and the team.
• Are smart people paying attention to this team?
• In-depth exploration: GitHub, Twitter, Discord, Farcaster, AMA

These actions are not radical, but informed. The best thing you can do for yourself is to make fully informed decisions.

Final Thoughts

Joining a startup is like writing yourself a check with your time and career. Therefore, ask questions like an investor and think like a founder. Raise the right questions, conduct your own due diligence, and make informed choices rather than emotional ones.

Work is a transaction, and a career is an investment portfolio; please choose wisely.