“I’m staring down the barrel of having to do a massive layoff at my company and tear down tons of work and decisions we’ve made. This feels awful. Is there any way to look at this situation as a positive, and if so, what should I be optimizing for (other than hair loss)?”
I’m thinking about using some of my equity to make a big move in my startup, but I’m worried about losing too much equity in the process. When is the right time for me to give up some equity and when should I hang back and look for a better situation?
Good hell, I feel like no matter what I do, I keep making the wrong decisions! I feel like I’m not cut out to be a Founder. There has to be someone out there that’s killing it while I’m hiring the wrong people, talking to the wrong investors, and going after the wrong customers. What am I missing here?
My startup is long since out of money and I’m doing everything I can to keep the show going. I feel like I owe it to my investors, staff, and customers to make this work even though at this point everyone has pretty much abandoned me. They would tell me if I should stop killing myself, right?
At some point after we’ve been so diluted by investors, are we really “Founders” anymore, or are we just glorified employees with a little bit of stock? At what point is it no longer worth sticking with our startup and may be worthwhile to just go start something else?
Are there any benefits to being a Founder who came from nothing? What kind of behaviors or expectations might they have which are an advantage at a startup company and why?
What do we Founders “owe” our employees? For all of the work they invest, what return should they rightfully expect on that effort? Who determines that payback, and how do we determine what’s sufficient?
How many follow up emails should I be sending prospective investors? How do I toe the line between being consistent on my follow up and just being a straight-up stalker? I don’t want to miss my opportunity but I’m not sure how this game is played exactly.
I’m meeting with lots of investors and I can’t seem to get a straight answer on where they stand. I’m either getting my teeth kicked in or getting strung along! Why can’t investors just give me a simple yes/no without me feeling bruised or confused?
How does someone “grow” in an organization that may never surpass a dozen people? My team wants is always comparing their growth path at my startup versus a big company — how do I become a better alternative?
Why are we perfectly comfortable using money as the metric for startup success at the expense of pretty much every other aspect of our lives? When we use money as the only metric, what other compromises are we making to get there, and frankly, is it even worth it?