Startup Interview 101

The pitch is tough to pass up: work really hard (like you do anyway), talented colleagues, fun office environment, change the world and get rich doing so. But before you swing for the fences there are few things you need to know to ensure the homerun isn’t actually strike three.

The questions below should each be answered by the interviewer in 30-seconds or less; if not,  RED FLAG.  Of course he/she may be having an off day, but the well-run companies of any size have consistency in message top to bottom and it transcends from words into actions. Unfortunately many startup executives can’t answer these questions succinctly, even the ones who’ve received funding. But, it is absolutely possible.

One founder was asked his vision and the answer was “be a billion-dollar online mattress company.” He’s well on his way. Another was asked and the response was “I want to make suits and fashion available to men anywhere in the US.” 1,200 stores later he succeeded. A third was asked and the feedback was “I want to end metabolic disease.” Nearly a billion-dollars in protein bars and powders later he is succeeding. These responses take 3 seconds. You’d be amazed at how many take 5 minutes…

1.  What is the ideal state, grand plan? Not a vision, a clear depiction. HINT: Unacceptable answers include, “we’re just riding the wave,” or “startups start then pivot, having an end goal is contrary to what a startup really is,” or “I don’t know that’s the fun part.”    

2. What is version 2.0 1-2 years from now? HINT: Unacceptable answer includes “we’re going to keep doing the same thing we do now.”

3. How do you make money? HINT: Can often be more complicated and fragile than actually appears.

4. Why don’t the big guys do what you do, what is preventing them? HINT: They're too big and bureaucratic doesn't always count, too easy of an answer. Look for some novelty. Novelty means the idea has some legs. 

5. If not included in answer to Question #2 - what are other streams of revenue you can utilize quickly?

6. Why should a customer buy from you and what is so impressive to make them stop buying from someone else?

7. Is there $100M demand for your product now or in the next 3 years? Why or why not?

8. Discuss your philosophy of people management. HINT: Likely the best answer is something like “we hire the best talent that fits our corporate and individual team culture then enable them the best we can to succeed.”

9. What gets you excited, totally completely amped, every day you go to work? HINT: Arguably the best question I’ve ever been asked in an interview…and have only been asked it once.


Joseph Nolan is a Los Angeles-based marketing and digital executive with over a decade of experience at leading companies in retail, ecommerce, entertainment and health/fitness. Opinions expressed on are his own. Please direct business inquiries and suggestions for future posts to