As a long-time founder/entrepreneur, I feel I should have most of the answers. I've been at this startup game long enough where nothing should be new to me. Sadly, I find myself with questions that someone with my tenure should have the answers to.

Maybe it's laziness, maybe it's embarrassment. Either or, they go unanswered.

Here are the questions, in no particular order, that I continue to ask myself:

  1. C-corp in Delaware. Is that still the way to go?
  2. Consumer messaging mobile-only apps, that are free. How the hell do they plan to make money?
  3. When your startup goes public, how does the founder make money? Do they sell everything and lose all ownership?
  4. How do penniless founders in SF (or anywhere for that matter) survive for so long?
  5. At what point are we not in beta?
  6. At what point are we not a startup?
  7. Is Google still a startup?
  8. Why is "making money" the wrong motivation to start a company in startupland? Is this why most startups fail?
  9. Do you really have to "disrupt" something to succeed? What does "Candy Crush" disrupt?
  10. What happened to Airtime? I really liked it when I met other startup founders that one night.
  11. Wouldn't it be better if funded startups moved away from San Francisco and New York to a cheaper location?
  12. Company name and domains are important or they're not important. Which is it now?
  13. WTF does Emoji mean? And, what does it have to do with running a startup?
  14. Why are there so many programming languages? Wouldn't it be easier if there were just one?
  15. Why does it take so long to code? Is there a coder union where everyone agrees to drag shit out?
  16. Is Founder's Card really worth the money, or is it just a card I pay for and never use to make me feel like I'm one of them?
  17. Does anyone recruit an advisor for actual advice or is it only for network effect and recognition?
  18. Can I end my work day at 5 PM or is that still sacrilegious by startup standards?
  19. Should I respond to an email immediately or pretend I'm busy and wait awhile before responding? If I wait, what is the appropriate amount of time so I still look busy?
  20. Speaking of emails, when do we add the disclaimer under the signature? After series A or when we go public?
  21. Are we all doing the illustrations for the Twitter pics now or are we back to real headshots?
  22. Is Google+ still worth the effort? Hell, is Facebook still worth the effort?
  23. What is the acceptable funding round where you can pay yourself an actual salary according to popular opinion?
  24. Does Fred Wilson still invest in startups? If not, should we still be reading his blog like it's the gospel?
  25. When did startups become a fashion instead of an industry?

What are your questions?

Published on: Nov 11, 2014