--- title: "Sleepless In Startupville: 23 Questions That Keep Entrepreneurs Up" description: I frequently talk to entrepreneurs at pretty much every stage in the process When I get together my fellow startup folks there are some recurring image: https://www.onstartups.com/hs-fs/file-13149286-jpg/images/startup-sleepless.jpg --- # Sleepless In Startupville: 23 Questions That Keep Entrepreneurs Up Written By: [Dharmesh Shah](https://www.onstartups.com/author/dharmesh-shah) December 27, 2010 - [strategy](https://www.onstartups.com/topic/strategy) - [life](https://www.onstartups.com/topic/life) Sleepless In Startupville: 23 Questions That Keep Entrepreneurs Up Written by [Dharmesh Shah](https://www.onstartups.com/author/dharmesh-shah) on December 27, 2010 - - - - I frequently talk to entrepreneurs at pretty much every stage in the process.  When I get together with my fellow startup folks, there are some recurring “themes” that seem to keep coming up.  Here are a bunch of questions that entrepreneurs ask themselves late at night.  Some of them are real doozies.![startup sleepless](https://www.onstartups.com/hs-fs/file-13149286-jpg/images/startup-sleepless.jpg) Of course, having *answers* to some of these would be useful — but that’s where you come in.  If you’ve got ideas on any of these, please share your experiences and insights.  If a particular question is of interest to you, let me know somehow, and I’ll put it on the schedule for a full blog article.  You can either leave a comment here, or tweet it, or post to the [OnStartups Facebook page](http://facebook.com/onstartups). Note:  I sat down and wrote all of these in one sitting in a “stream of consciousness”.  I could have kept going for hours.  Turns out, we entrepreneurs have *many *questions that keep us up at night. **23 Questions That Keep Entrepreneurs Up At Night** 1. Is my idea good enough to quit my job? 2. Should I try to raise outside funding? 3. Did I make a mistake picking my co-founder? 4. Is it wise to take angel investing from my Uncle Larry? 5. Do I need office space to be seen as a “real” business? 6. I need help.  Is it ok to bring my spouse/sibling into the business? 7. How much should I really worry about my company name? 8. One of my co-founders needs cash to pay the bills, do we give him a salary? 9. I’m passionate about our vision, but it’s been really hard getting users.  Should I pivot? 10. What should I charge for my product?  Will I be able to change my price later? 11. I have investor "interest", but no checks.  What should I do? 12. Someone from the early team is not as valuable as we thought.  Should we let them go? 13. A customer wants to pay us a bunch of money for some custom features, what do we do? 14. One of our competitors is getting all the publicity (and capital) -- but our product is better.  What do I do about it? 15. I keep hearing about the importance of "work life balance", but don't know any successful entrepreneur that has pulled that off.  Is it a myth or am I doing something wrong? 16. One of our board members is a real pain in the ass, is there anything I can do? 17. How do I recruit a great product manager?  What does a product manager do anyways? 18. I’ve already tried to hire every super-smart person I know.  Where else do I look? 19. Things are going reasonably well, but not great.  Should I try to sell the company? 20. I’m no longer passionate about the idea, do I stick with it? 21. There’s no startup ecosystem where I live.  Should I move somewhere there is? 22. How long should I work on my startup while I’m still employed by someone else? 23. I’ve been at it for a couple of years but nothing is happening.  What’s wrong with me? **Bonus**:  24. I love my company, but most of my time is spent doing things I don’t love.  How do I fix this? What do you think?  Care to add some more quetions to the list — or try and answer one of these?  Which question do you think is the most common — or the most difficult to answer? ## Related Posts [The Classy Way To Get Media Coverage For Your Startup guest October 30, 2012 The following is a guest blog post by Nicholas Holmes. Nicholas is the co-founder of MediaGraph, a public relations platform that enables small businesses to manage their own media… Read Post ** ](https://www.onstartups.com/tabid/3339/bid/91423/The-Classy-Way-To-Get-Media-Coverage-For-Your-Startup.aspx) [Adam Smith Video On The Story Of Xobni November 17, 2009 As noted in my previous article on startup marketing, I had the opportunity to speak at the MIT Startup bootcamp recently. My friend, and an all-around great guy, Adam Smith (founder… Read Post ** ](https://www.onstartups.com/tabid/3339/bid/11043/adam-smith-video-on-the-story-of-xobni.aspx) Subscribe ### Get OnStartup News and Updates in your Inbox. ```json { "@context" : "https://schema.org", "@type" : "BlogPosting", "author" : { "@type" : "Person", "name" : "Dharmesh Shah", "url" : "https://www.onstartups.com/author/dharmesh-shah" }, "datePublished" : "2010-12-27T16:38:00.000Z", "headline" : "Sleepless In Startupville: 23 Questions That Keep Entrepreneurs Up", "image" : [ "https://www.onstartups.com/hs-fs/file-13149286-jpg/images/startup-sleepless.jpg" ], "mainEntityOfPage" : { "@id" : "https://www.onstartups.com/tabid/3339/bid/34265/Sleepless-In-Startupville-23-Questions-That-Keep-Entrepreneurs-Up.aspx", "@type" : "WebPage" }, "publisher" : { "@type" : "Organization", "logo" : { "@type" : "ImageObject", "url" : "https://www.onstartups.com/hubfs/mjtw-assets/logos/onstartups-logo@2x.png" }, "name" : "OnStartups" } } ```