Startups Anonymous: 25 questions founders are too embarrassed to ask

By Startups Anonymous , written on July 2, 2014

From The News Desk

[This is a weekly series that brings you raw, first-hand experiences from founders and investors in the trenches. Their story submissions are anonymous, allowing them to share openly without fear of retribution. Every Wednesday, we'll run one new story chosen by Dana Severson, who operates StartupsAnonymous, a place for startups to share, ask questions, and  answer them in story-length posts, all anonymously. You can share your own story here.]

As a long-time founder, 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 embarrasment. Either way, they go unanswered.

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

  • C-corp in Delaware. Is that still the way to go?
  • Consumer messaging mobile-only apps, that are free. How the hell do they plan to make money?
  • When your startup goes public, how does the founder make money? Do they sell everything and lose all ownership?
  • How do penniless founders in SF (or anywhere for that matter) survive for so long?
  • At what point are we not in beta?
  • At what point are we not a startup?
  • Is Google still a startup?
  • Why is "making money" the wrong motivation to start a company in startupland? Is this why most startups fail?
  • Do you really have to “disrupt” something to succeed? What does "Candy Crush" disrupt?
  • What happened to Airtime? I really liked it when I met other startup founders that one night.
  • Wouldn't it be better if funded startups moved away from San Francisco and New York to a cheaper location?
  • Company name and domains are important or they're not important. Which is it now?
  • What the fuck does Emoji mean? And, what does it have to do with running a startup?
  • Why are there so many programming languages? Wouldn't it be easier if there were just one?
  • Why does it take so long to code? Is there a coder union where everyone agrees to drag shit out?
  • 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?
  • Does anyone recruit an advisor for actual advice or is it only for network effect and recognition?
  • Can I end my work day at 5 PM or is that still sacrilegious by startup standards?
  • 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?
  • Speaking of emails, when do we add the disclaimer under the signature? After Series A or when we go public?
  • Are we all doing the illustrations for the Twitter pics now or are we back to real headshots?
  • Is Google+ still worth the effort? Hell, is Facebook still worth the effort?
  • What is the acceptable funding round where I can pay myself an actual salary according to popular opinion?
  • Does Fred Wilson still invest in startups? If not, should we still be reading his blog like it’s the disciple?
  • When did startups become a fashion instead of an industry?
What are your questions?

[illustration by Brad Jonas for Pando]