Questions That a Founder is Too Embarrassed to Ask

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 or, 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 gospel?
  • When did startups become a fashion instead of an industry?

What are your questions? 


    • I can’t answer all of the questions, but here are a few from my perspective:

      C-corp in Delaware. Is that still the way to go?

      As is always the answer, “it depends”! The C vs. S question is one that people confuse all of the time. I am not a tax attorney, but as a corporate general counsel, I can tell you that Subchapter C of the Internal Revenue Code provides for “double taxation,” meaning tax on profits, and tax on the income to shareholders. Subchapter S provides for “pass-through taxation,” meaning shareholders are taxed only on income. In my experience, pass-through taxation is better and less expensive, and it is not permitted for companies with more than 100 shareholders.

      Delaware is desirable to some people because you do not need to disclose the identity of your shareholders, but guess what? Nevada has the same benefit! Also, regardless of what state you do business in, you will need to register your company as a “foreign corporation” that is doing business there, and odds are, you will need to disclose someone’s identity. Another reason that “corporators” often select Delaware is because the courts are very sophisticated about business disputes, but the truth is, it probably doesn’t matter and you can probably incorporate wherever you are actually working. Why hide? I can go into detail if you would like – http://www.gerstenmuir.com for more information or to reach me.

      Consumer messaging mobile-only apps, that are free. How the hell do they plan to make money?

      By acquiring all of the data on your phone and using it to learn about you and everyone you know, so that they can target you for marketing of things you didn’t know you needed before you have heard of them.

      When your startup goes public, how does the founder make money? Do they sell everything and lose all ownership?

      It depends – they might sell out completely before it ever goes public or they might be diluted with some kind of weighted average. Watch the Social Network for a pretty decent education on dilution!

      How do penniless founders in SF (or anywhere for that matter) survive for so long?

      Couch surfing? Air BNB?

      Why is “making money” the wrong motivation to start a company in startupland? Is this why most startups fail?

      I think most startups fail because running a business is really difficult and risky, and it is so much easier and more secure to work for someone.

      Wouldn’t it be better if funded startups moved away from San Francisco and New York to a cheaper location? Yes! http://www.forbes.com/sites/tompost/2014/03/13/the-best-places-to-launch-a-startup-in-2014/ http://www.entrepreneur.com/article/227436

  • Here are answers (opinions) for some of your questions:

    1. C-corp in Delaware. Is that still the way to go?

    Hacker news talks about this in this thread: https://news.ycombinator.com/item?id=244009

    2. Consumer messaging mobile-only apps, that are free. How the hell do they plan to make money?

    Advertising, user data, whatever. Monetization comes in many forms and normally you’d get help from investors or hire a CFO if it’s not obvious.

    3. When your startup goes public, how does the founder make money? Do they sell everything and lose all ownership?

    With an IPO a founders personal shares are valued, they can then sell them at that price or hold on to them. Founders normally keep executive roles so they receive a wage like any other job. Here’s more info about IPOs and why Mark Zuckerberg now receives a $1 salary: https://en.wikipedia.org/wiki/Initial_public_offering_of_Facebook

    4. How do penniless founders in SF (or anywhere for that matter) survive for so long?

    Successful startup founders tend to be smart and entrepreneurial, the ones that last find a way. Although I think SF cost of living is getting ridiculous.

    5. At what point are we not in beta?

    When you’ve found product market fit, when you’re on track and know what you’re doing, when you fix all those damn bugs. It’s different for every startup.

    6. At what point are we not a startup?

    A startup is loosely defined as a small new company. It’s a grey area.

    7. Is Google still a startup?

    No, but their marketing team has kept up that ethos.

    8. Why is “making money” the wrong motivation to start a company in startupland? Is this why most startups fail?

    Because you should have a passion for your idea, if your motivation is money you might as well work for an established company because the fact is: a lot of startups don’t make money for a long time and 3/4 don’t succeed. The ones that do succeed normally have founders that are willing to be there 24/7 to make it happen even though they making zero money. The guys from Buffer put it brilliantly: https://www.youtube.com/watch?v=Uh5mtmQZWv8

    9. Do you really have to “disrupt” something to succeed? What does “Candy Crush” disrupt?

    You don’t. It helps if your idea is original and better than the norm. E.g. the iPod disrupted the music industry because it was pleasant to use. Some location-based startups do well in their country because they’re a clone of another successful startup that isn’t expanding fast enough.

    10. What happened to Airtime? I really liked it when I met other startup founders that one night.

    I don’t know.

    11. Wouldn’t it be better if funded startups moved away from San Francisco and New York to a cheaper location?

    Startups and investors go to hubs because it makes business easier, but that doesn’t mean you can’t be successful if you’re based in a small city – look at MailChimp.

    12. Company name and domains are important or they’re not important. Which is it now?

    I think they’re important. Nobody wants to work at ‘megafucks’. https://farm5.static.flickr.com/4043/4421463879_ef53c0e421.jpg

    13. What the fuck does Emoji mean? And, what does it have to do with running a startup?

    Nothing, they’re smileys.

    14. Why are there so many programming languages? Wouldn’t it be easier if there were just one?

    Different languages are used for different things. You probably wouldn’t build a shed out of cement or a road out of wood, likewise there are different languages for different products.

    15. Why does it take so long to code? Is there a coder union where everyone agrees to drag shit out?

    Building things that are quality (e.g. organised, bug-free and scalable) takes time. Nobody will pay for something that looks and feels like a rush-job. At the same time some projects are bigger than expected and some programmers are faster than others.

    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?

    What is a Founder’s Card? Oh. Haha. Just DuckDuckGo’d it. Looks like a honeypot for people who found a startup as a get-rich-quick scheme. I don’t know if it’s worth the money.

    17. Does anyone recruit an advisor for actual advice or is it only for network effect and recognition?

    Much of the startup world, getting press, saying words like ‘disrupt’ and ‘scalability’ and ‘growth hacking’ (I’m guilty) is just about playing the game. You talk the talk and connect with the right people and it gives you an edge. At the end of the day, the only thing that matters is the product. The only thing.

    18. Can I end my work day at 5 PM or is that still sacrilegious by startup standards?

    Don’t sweat the small stuff. Founders are often expected to be addicts though, and the successful founders don’t seem to switch off. I don’t think a day goes by when Zuck doesn’t work?.He and his co-founders have probably worked most days since they launched TheFacebook.

    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?

    Answer an email when you get time, be genuine.

    20. Speaking of emails, when do we add the disclaimer under the signature? After series A or when we go public?

    I don’t know.

    21. Are we all doing the illustrations for the Twitter pics now or are we back to real headshots?

    Do what makes you happy.

    22. Is Google+ still worth the effort? Hell, is Facebook still worth the effort?

    Google+, nope. Facebook, kinda. Much harder to get established on Facebook now than it was for startups 5 years ago, unless you’ve got a lot of ad money I recommend looking at other newer social networks.

    23. What is the acceptable funding round where I can pay myself an actual salary according to popular opinion?

    Tricky. Talk to your investors and co-founders. Unless you want a really big salary I’m sure it’ll be fine. Consider your employees wages too.

    24. Does Fred Wilson still invest in startups? If not, should we still be reading his blog like it’s the gospel?

    He runs Union Square Ventures, one of the most successful venture capital firms ever, so he probably has some smart things to say. But read what you want.

    25. When did startups become a fashion instead of an industry?

    It feels like being a startup founder was always fashionable, and startups tend to be part of the tech industry which is fashionable because it’s booming (could say bubbling).

    I hope this helped, it’s all just opinion, please don’t read it as fact. I’m @billfranklinuk on Twitter if you want to chat about this some more.

  • Thanks for the comic relief.

    This post was too hilarious. The funniest part is that someone actually wasted their time responding your questions with some serious responses.

    (P. S. The opening post belongs in the Q. & A., not Stories, section.)

  • I like my Founders card benefits! Saved money on flights, hotels, and shopping. The Tory Burch benefit alone has made it worth it.

  • I disagree on the C Corp De:

    The Limited by Shares company in the UK, also known as Limited,

    is a valid workaround and more lean that the C Corp, apparently.

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