Move from one start up to another?

  • Last Updated:
  • Jan 31st, 2015 6:30 pm
Nov 16, 2014
6 posts
Toronto, ON

Move from one start up to another?

Hi RFD members

Just wondering if any of you has had success moving / working from one successful start up to another still to be profitable start up?

I joined a start up ~2 yrs ago with an ex-boss - to make things short, it became a successful business as the boss was a more senior person in the old firm that we had worked for- able to pull clients. It is definitely a going concern now (eg profitable business) where I am receiving a good salary (and some equity - eg not significant but still some equity - albeit not sure if it's the same "class" as the boss'). Unfortunately, with success breeds "arrogance" and this boss is getting more and more "difficult to deal" with in terms of "micromanagement" and personality/mood/age. He seems even more set in his ways as he ages...

I understand his situation, in that, with a successful business, there's more to lose and therefore, he micromanages even to the point that my inputs are sometimes ignored - some inputs which would really not impact the clients a lot he will not consider (eg but which may be good for our efficient operations, increase profitability longer term at the expense of short term pain, etc). This makes me feel "de-motivated" as it wasnt like this at the start. These days, when I would recommend we do something, he would counter and state his view and him being the "boss", I leave it at that. It wasnt like this at the start and he even was so enthusiastic as to call me a "partner", shareholder, etc. He also has majority control so even if I have shares in the company (i got it for free, so I'm not banking on it if I leave), I am a minority and treated more as employee than partner. (statements like: eg. "you dont deal with clients so you don't know what youre talking about", "your lawyer doesnt know our business so we will proceed with this agreement", etc). Should I move to another start up of another ex-colleague who was my mentor in another firm? In short, while pay is good, I find that I'm having a hard time motivating myself to give new ideas etc given that he will just decide to do whatever he pleases anyway...

Fortunately (or not), I have the option to join another ex-colleague who was my mentor and started up his own firm too. While his is less successful than ours (eg still in the red), it'll be most likely breakeven this yr. He is less successful now since he is less senior that my current boss in the old firm we all worked for. My working relationship with my ex-colleague/mentor is way better than where I am now. Unfortunately, the risk I have to take is that I have to re-do all this again and take very little/zero income in the next 6-12 months (at least). In case one is curious, the reason why I have these options is that my old firm "blew up" and everyone more senior than me started their own "gig" (I couldnt since I didnt have any clients btw LOL)... I went with, what I had thought to be the better and more senior person then. Truth be told, I guessed right in terms of the success of the business so far. What I was /or seem wrong about is the reading in terms of the working relationship.

Any advice or thoughts that I need to consider is much appreciated. I am cognizant that my old mentor who I had a good working relationship with might also have changed as he is running his own show these days, nonetheless, it may (or may not be worth the risk). Thank you for any ideas I need to further consider (over and beyond foregoing $ vs working relationship/quality of office life).
1 reply
Jan 20, 2010
38 posts
I know very little about start up companies, but based on what you have written here is my 2 cents worth.

If I was you I'd make sure this time around if I chose to move on, that I do the following:

- Obtain a significant share or holdings in the company ( make that part of the contract)
- Get legal advice signing on to the company i.e. who owns the name, the brand, types of compensation for contributions that bring in money, ideas, products, improved workflows...). Also get advice on whether or not you could buy your partner(s) out if the situation ever arises etc. Put these into your work contract too.

Keep work relationships as work related as possible. Yes I know that there are oftentimes spill-overs into the personal life, but maintain the focus on trying to improve your working life in every situation. Also keep in mind that you are now a seasoned contributor to start ups, use your past experiences to better gauge your route to success in that environment. All the best