41–50 of 69 posts
(1) the grass is always greener on the other side (2) serial entrepreneurs are more common than parallel ones (3) don't you have a performance requirement with your investors? (4) does your shareholder agreement allow any of this? (5) have you talked this over with your investors? (6) it all depends on the cap table (7) you could always sell your stake in the current company or engineer an MBO (8) doing another compa…
(11) Ambition is the enemy of consistency beware
You know the answer to this, talk to your most friendly board member/investor. If he's not receptive to trying an experiment, it's doubtful anyone else will, at that point you either decide to stick with the current business, or leave and start the other business. Just because he doesn't like the experiment idea doesn't mean he may not stake you in the new venture. Also if you were not hand picked as the CEO, you might find that leaving is met with happiness. Just like you the board/investor always think there is something better to be had, so they might be happy to get an upgrade at CEO, or think they can get an upgrade.
As the CEO of a funded company, you should know that the "we will partner with you" line is handwavy BS 99.9% of the time.
This statement is not a measure of potential money coming in the door. Rather, it's usually code for "we would like you to pay us to build your website/social presence" (if said by an agency owner) or "we would like to do some sort of advertising joint venture" (if said by a content marketing-driven company.)
Have you gotten anyone to actually toss a credit card at you across the table for this idea? If not, you have no customers and no proof this idea will work.
P.S. I would be less blunt if talking to a new founder. Often they get really excited about these garbage "partnership opportunities." But you, as the CEO of a funded startup, should know better.
(1) the grass is always greener on the other side (2) serial entrepreneurs are more common than parallel ones (3) don't you have a performance requirement with your investors? (4) does your shareholder agreement allow any of this? (5) have you talked this over with your investors? (6) it all depends on the cap table (7) you could always sell your stake in the current company or engineer an MBO (8) doing another compa…
I had the misfortune to work with a CEO who not only started a second company but used the VC's from his first company to start the second. His first was in a similar state (making money, but not out of the woods). didn't end well for either startup A or B. Focus is critical, unless you are Jack Dorsey I guess.
Well Twitter can't ship product, and many people within Twitter blame @jack. See for eg that article about the woman who setup their original abuse proceedures. Plenty of quotes in that which show how he stops anything getting fixed.
Maybe Musk might be a better example.
Seems, to my completely inexperienced point of view, like its time to hire your replacement. Establish a board with yourself on it (probably alongside investors), hire your replacement, and let them run your first company. Use your position on the board to keep in touch with and help direct the running of the company, while freeing up time to work on a second venture.
One thing you didn't really describe is how long you've been in your company, and what you accomplished. Are you a founder? Were you hired as a CEO? How long were you in your position, ect?
If you're a founder, at some point it's expected that you'll leave to start another company. If you replaced the founder, it's expected that you'll drive growth in a defined marketplace.
I think you need to find out what the board expects you to do with the current company, and see if it's a good time to transition your interests.
Though most people here would disgaree with me, and even me myself 5 years ago would have vehemently disagree with my current self, I am of the view that you should consider running both businesses.
The critical insight that fosters this view is that after a certain amount of time being a CEO you realize that the growth of the company is not entirely in your hands. Market forces play an indeterminate but critical role in the growth of a company. Consequently, it maybe the case that your current business might actually benefit from you stepping away and letting it mature by itself.
After having run a particular genre of company for a bit, you start getting a feel of what will move the needle and what will not. If there is incremental growth to be had and little scope of exponential rampup, you might be better off baking something else. There is a chance that this business will turn around by itself over time or maybe by focussing on something else, you get a better perspective on your existing business to take it to the next level.
I am currently ramping up on a business that I started on the side 5 years ago. It wasnt really a business, it was an experiment. But it took a life of its own. A couple of months back, I realized it had the potential to be a big business and I was well placed to capitalize on it. Now I am ramping up that 'experiment' so that it employs a handful of people. The 'experiment' will pay for these people and I will again let this idea bake for another year and focus on something else.
I am coming around to the view that this is best way to work for 'serial' entrepreneurs. Most people who arent serial entrepreneurs, that includes almost everyone who have been a founder for less than 10 years wont see the wisdom in this. Unfortunately, this will include your investors and other employees. The only way to get them to fall in line is if you can get them to fall in line without requiring them to see the wisdom of your action. It might be impossible in your current setup, in which case you need to restructure so that you can operate optimally.