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  


The dad was a football man, former college player turned member of a top-rated HS officiating crew, but at an early age his son initially took to the sport of baseball instead.  Not possessing knowledge of the sport near that of football, he sought ways to learn the ins-and-outs as quickly as possible so he could teach his son. Reaching out to colleagues and friends, the dad discovered a renowned 3-day coach’s clinic about an hour from home. The best in game, top college and MLB coaches staffed intimate seminars for groups of ~40 discussing everything from mental preparedness and proper warmups to situational hitting and pitching strategies. For several years the father took time off from his busy corporate schedule and attended the clinic with his son, each year met with the same excitement and anticipation. They achieved their goal of continuing to learn about baseball, and more importantly, strengthened their father-son relationship and expanded the son’s perspective on the world around him.

Lesson 1: Never stop learning (continuous improvement). There’s always more to learn. One is seldom the smartest person in the room and those who think they are often aren’t. Surround oneself with the best possible talent and together everyone will be more successful.

The main ballroom was standing room only, packed wall-to-wall with 200 H.S. coaches from around the country. The father and son duo had skipped an earlier seminar to spend time testing the latest gear from vendors – but primarily so they could score 3rd row seats for the most anticipated presentation of the event. The sound of tobacco and bubble gum chewing men frantically clicking their pens and sharing exaggerated stories of victories and standout players of times past while waiting for the session to start was unforgettable. Then without notice a hush fell across the mildly rambunctious crowd and the discussion on the philosophy of coaching baseball began…

dad pic.jpg

He strode onto the stage with uncanny charisma, authority and confidence. Simply put, when it came to college baseball he was legitimately THE MAN. Inventor of LSU’s renowned homerun power hitting offense dubbed Gorilla Ball and, more impressively, winner of 5 NCAA championships along with 11 NCAA World Series appearances, the guru himself Skip Bertman stood before the crowd. In the previous season his LSU Tigers were a favorite to take the national title for a second consecutive year but were eliminated early in the post season shocking the baseball world. He spoke of how his staff employed all the usual tactics after a devastating loss: working harder in the offseason, “recommitting oneself” to the game, reducing distractions and so on. Everything good coaches do in any sport.

But then one day during an off-season practice suddenly it all became clear to him. An assistant coach hit a ground ball to their star infielder who scooped it up and threw it over to first base, routine play like always. Skip muttered to his assistant, “That was pretty good.” What was immediately clear was that he had allowed his staff and all-star cast of players to accept “pretty good” as their normal way of working. They’d become complacent and simply figured that “pretty good” from the best players in the country would be good enough to win a championship. The “pretty good” mentality stealthily crept its way into the program, Skip was honestly upset about it and he took full responsibility. The hall of fame coach’s closing remarks left the crowd silent and were the buzz of the remainder of the conference: “If you learn anything during this seminar, it should be that sometimes pretty good is in fact good enough. But, pretty good isn’t great. Everyone else works hard. Everyone else has good players. So to be a champion, it often takes being something great. Don’t let ‘pretty good’ infest you and your teams.”

Lesson 2: Humility. As the crowd exited, the father’s words to his young son were as unforgettable as the coach’s. “You see that man? He’s the best at what he does in the entire country. He just stood up here in front of all these people and admitted he made a mistake. No one’s ever too good to admit they screwed up. What’s important is you learn from it and don’t make the same mistake twice.”


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