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Should I take the start-up offer??

danomitedanomite subscriber Posts: 3
edited October 2016 in Office Workers
Hey guys,

Apologies if this is in the wrong section, I looked around, and this seemed like as good a place as any.

I need advice. I received an offer from a start-up. I'm still evaluating the offer, but I'm having a hard time making a decision of taking it or staying where I am. Here's the story.

I've worked for my current employer for 13 years. It's been my only real job. I hustled my way up from being a temp support guy to being a senior product person making 6 figures. The company has been very good to me and overall I'm very happy. I'm on the product that should be the future of the business in many ways. This is a fortune 200 company. The building is brand new and beautiful, I love the people I work with, seriously, I'm starting to feel crazy for considering leaving while I'm writing this, but hear me out. The only real problem is that the guys above me are very senior, qualified, great guys who aren't going anywhere and my ambitious side is getting antsy about my next move because it's not clear.

Meanwhile, a growth stage startup down the road is run by a guy I've known for many years, and they've raised 20M+. They have 100 employees. They're in the same industry and vertical, but slightly adjacent to what I'm doing now. Anyway, they need product people and I would be the first. I see it as an opportunity to build out my own team. The salary, benefits, etc. are basically a wash compared to what I have now. The one intriguing yet risky piece is the stock options. I just emailed my would-be boss and asked questions to understand the value of the options (total percentage the options represent fully dilluted etc.).

Anyway, I think the draw for me in the start-up is change, chance to build my own team, and the shot at a home-run if the company really makes it big (I know this is beyond risky).

Am I crazy? Should I take it or not? What questions should I be asking? Thanks if you've read this far. I appreciate the therapy.

Below is my pro\con list. :D

Pros of start-up offer
1. Opportunity to learn something new by joining a startup
2. Get to run a native mobile app
3. Stock options that could be very valuable one day
4. Start up culture relaxed dress code young team hungry
5. Customers love the products
6. Learn from "Bob" who seems like a great guy
7. Seemingly clear path to a director or vp position
8. Catered lunch once a week
9. Marginally more salary

Cons of start-up
1. Unknowns
2. Have to learn new products processes and people. Starting over. I'm the new guy.
3. Less job security
4. No 401k yet
5. No HSA
6. No gym
7. Marginally more expensive health insurance\benefits
8. No vision coverage

Pros of current
1. Solid company very stable
2. My product is the future of the business
3. I know everyone and like most everyone
4. Fun travel opportunities
5. Great people I really love
6. 401k
7. HSA
8. My view and desk area
9. My computer and crap like that
10. My history with the company and connections
11. Pride of being with the same company for 13 years
12. Paid for phone
13. Total guaranteed compensation is a little better

Cons of current
1. Super stressful, tons of customer escalations
2. I don't feel like I'm winning a lot of the time and I don't have enough time to spend on building stuff
3. Unclear next career move up and next salary increase could be in the same position for a long time
4. Not much major upside potential, no chance at a home run


  • Charlie PCharlie P subscriber Posts: 84 Silver Level Member
    The fact that you are putting this much thought into the offer means that you should take it. In the end it's a personal decision, but one thing that is for sure is that if you don't do it you will live the rest of your life with the regret of not having tried. Do your homework and make sure that you are not positioning yourself for failure, but if it all looks good it seems like a no brainer. Again, it is your personal decision and don't let anyone force you in one direction or the other.
  • danomitedanomite subscriber Posts: 3
    Thanks for the reply Charlie. I appreciate it. The startup talks about me having the opportunity of building out the product team and leading it but I'd rather come in with a title of director or head of product as opposed to product owner so it's clear that I'm coming to the company to lead that team. I think I'm going to negotiate for it because I have 13 years experience in the vertical. Or am I pushing for something that is unneccesssry? I just want this move to make sense on my resume and career trajectory and be a clear move up as opposed to something that might look like a lateral move.
  • Ryan O'BlenessRyan O'Bleness administrator Posts: 1,137 Site Admin
    If I was in your situation, I would have the exact same worries, but the exact same level of excitement about the new opportunity. This is the kind of decision I would go back-and-forth on. Do you have a timetable on accepting the offer, or is that not an issue since they would love to add somebody with your experience to the team at any point?

    I think what you would need to determine first and foremost is what job would you be more passionate about? As Charlie mentioned, if you don't take this opportunity, and you feel stuck at your other job, you may spend a lot of time thinking "What if?" On the same token, if you take the risk, and it doesn't work out, you will have those same feelings of "What if?," so it is obviously a difficult decision. Do you know that whole line about "Pick a job you love and you'll never work a day in your life," or something along those lines? I am not sure if that is necessarily true, however, I will say working a job you love makes things much easier on you and your happiness. Trust me, I know from experience.

    Another question you need to ask yourself is are you a risk taker, or a dreamer who always plays it safe? The opportunity at the startup seems to outweigh the opportunity at your current gig, in terms of advancing your career. You also mentioned the salary would be similar, or you may actually make more at the startup, but you will accrue more personal insurance costs. No 401K, either. With that said, if the startup continues to see success, those benefits will likely come. There is nothing wrong with playing it safe, but there also isn't much adventure in it.

    The excitement and career advancement potential that the new opportunity brings seems to beat your current role by a tenfold, but the security of your current job combats all of the unknowns of a startup. At the end of the day, only you get to decide what is best for you, but I hope Charlie and I were able to help you look at it from a new perspective.
    Ryan O'Bleness
    Community Manager
    StartupNation, LLC
  • LifeRevivalUniverseLifeRevivalUniverse subscriber Posts: 76 Silver Level Member

    Just don’t think much about negative consequences. Personally I would regret that I didn’t try. Maybe you will not have such an opportunity later...

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