Questions To Ask Before Quitting Your Job To Work At A Startup

August 5, 2014

corporate-to-startupTwice in my career I have left corporate jobs for startups. The first time I left was because I wanted to be in an innovative work environment where we would be inventing and creating technology that never existed. I tasted what it was like to work in a fast moving amazing technology company. I felt alive and the energy from my team was amazing. Before joining the startup here are the questions I asked myself:

Questions I Asked:

  • How much money was being raised through venture capital?
  • What was the burn rate?
  • How much equity would I be getting? How many total shares were there?
  • Do I believe in the CEO’s vision for where the company is going?

In hindsight where these good questions?

  • We raised $21M.
  • We burned through that money in less than 12 months. You’d think $21M would last a long time. It doesn’t when you’re hiring like crazy. I was one of the first few hires and we ended up hiring 90 people at our peak. Hiring and growing can mask how a company is really doing. From the outside it looks like you’re successful. The burn rate was out of control.
  • I got a ton of stock options. Worthless if the company doesn’t survive. The initial job offer had two options A) Higher pay, lower stock options. B) Lower pay, high stock options. I counter offered and asked for option C) Higher pay, higher stock options. If you think you’re worth it, ask for it.
  • I met and believed in the founder and CEO, I drank the Kool-Aid. I was in the inner circle.

Today I would ask a different set of questions:

  • Would I personally invest in this startup?

Joining a startup is akin to investing in a startup. You’re about to put a ton of your time into building up this startup. You’re investing more than what an investor is putting in. This question leads to more questions such as market potential, addressable market size, competitive landscape, founders’ backgrounds, customer validation, etc. If I wasn’t ready to invest money into the startup, I would’t want to go work there.

  • What are the credentials of the founding team?

If I don’t believe in the people that started the company, there’s no way I would go work for them. This is actually more important to me than what the startup actually does. Startup will shift direction and for lack of a better word, pivot. There are people that I would work for where I don’t care what the idea is, I would just join them because I believe in them.

  • What are the core values of the company? Do my core values align with those of the founders?

This question is more important to me than ever. If we don’t align here there’s no way I could go work for that startup. Startup pressure is so intense and when the founders are facing the darkest moment only their core values will stand the test. Who are they when they hit the wall. Is that something you want to be associated with. Is that something that you will be proud of their decision making. If not, don’t even bother working for them.

  • What kind of work culture do I want to work in?

You will be spending most of your day with the people in this startup. What’s the culture like? I want to enjoy working with the people I’m around all day long and the work environment. I personally want to work with people that have a goal crushing attitude, love to serve their coworkers and customers, and are always learning. We all have a choice in what type of work culture we want to be in.

  • Will this be a demanding, learning environment?

If you’re the smartest person in the room, you’re in the wrong room. I want to work really hard, that the only thing I know how to do. I also know that I have a ton more to learn. If I’m not in an environment where I’m always learning, I don’t want to be there.

What are some questions that you would ask?

If you’re looking to make the jump from corporate to startup and have questions like these, you should attend our event “Emerge from Corporate to Startup” on August 14, 2014 at 6pm.



6:00 – 6:30pm – Networking (Meet some startups who are hiring!) / Pizza and Drinks
6:30 – 7:10pm – Session 1: Emerging as a startup founder or co-founder / QA
7:15 – 8:00pm – Session 2: Emerging as an early stage startup employee / QA

Brad Carpenter  @bradcarpenter

Brad worked for Microsoft for over 20 years — he was a GM worked on Surface v 1.0 as well as managed the Keyboard Mouse Device Division. Brad has also been involved with multiple startups as CEO. He is also an angel investor and part of the Seattle Angel Conference board.

Don Gerould @dgerould

Don’s corporate life was spent at Citysearch and as a Senior Manager with Sales Operations at Amazon. Don’s last company was the Surf City Marathon. Don started his current company Cogent Equity more than 12 years ago and provides services including exit strategy planning and capital fundraising.

Sandeep Phadke @viaairlift

Sandeep was responsible for the Kindle rending engine at Amazon. Sandeep also worked for many years at Microsoft. Sandeep quit working for big corporate companies for life changing personal reasons. He is on his first pivot and now joining forces with another Seattle startup!


Shauna Causey @shaunacausey

Shauna started her career in Marketing and PR working for the Seattle Mariners, Q13, Comcast, Nordstrom and has worked at a handful of startups like Ants Eye View (acquired by Price Water Coopers), (acquired by Ebay), and UP Global (aka Startup Weekend). Mentor and advisor for startups.


Picture of thinkspace