Sleepless In Startupville: 23 Questions That Keep Entrepreneurs Up

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Sleepless In Startupville: 23 Questions That Keep Entrepreneurs Up

 

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

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.

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?

Posted by Dharmesh Shah on Mon, Dec 27, 2010

COMMENTS

Another one: "Do I need an advisory board, and if so what should it look like?" 
 
(My answer: In most cases, not anymore. They were all the rage in 1999, but nowadays if you're a compelling person and have a compelling business idea, the advice flows freely and you can reward people who help you the most.)

posted on Monday, December 27, 2010 at 10:56 AM by Peter Alberti


As for #17: I recently read that the founder(s) should be the Product Managers. Love this concept...

posted on Monday, December 27, 2010 at 10:57 AM by Peter Alberti


Here are some that I am facing: 
 
A variant of #2: Should I "think big" and raise money or should I "be realistic" and bootstrap? 
 
and 
 
If I raise money, how much of the business do I give away? Or said in other words, how much is my idea really worth?

posted on Monday, December 27, 2010 at 11:02 AM by Miguel Buckenmeyer


Another question - The market is there, the need is felt and the timing is correct, but is it really worth taking the risk to invest in the expansion right now. But the fear is that if not now then someone would be there tomorrow.

posted on Monday, December 27, 2010 at 11:34 AM by Rahul Bhavsar


Same issue as Miguel. I can raise money but most of my potential investors are family friends. Now their investment in me won't make them bash an eye lash in terms of the financial hit they will feel but my worry is this is the one to pitch to them ill get how do I know if this one is the one ?

posted on Monday, December 27, 2010 at 11:35 AM by Kellen Moriarty


5. Do I need office space to be seen as a “real” business?  
 
The answer is simple, working from home is a myth, especially when you do most of the work. Self motivation is not possible with your pijamas on and if you are not Hitler, there is no such thing as self discipline either. 
 
You need to hire at least one people (or work with your partner), provide them space and build a team. This is why you need an office. Don't care about what people say. Find a 30m2 office and work your ass off. Your biggest expense will be your breakfast and lunch bills, not the rent!

posted on Monday, December 27, 2010 at 11:36 AM by Gokhan Besen


Here is another one: During the bootstrap period do i optimize or maxmize? Should i pour all my resources and make it happen in a few months or do with small incremental amounts of resources and prolong it for longer time?  
 
 
 
 
 
Btw, a shameless plug for Vaayoo's mobile application framework. If you have a great idea and want to create a killer mobile app out of it, try Vaayoo: http://www.vaayoo.com/appsplatform/VaayooAppsplatform.aspx ..We have helped several non-tech entrepreuners turn their ideas into market-leading and money making mobile apps. You just need an idea..Leave the rest to us.

posted on Monday, December 27, 2010 at 12:07 PM by Ranjit Sawant


OMG you read my mind! I think I have asked myself nearly all of those questions. Ok, so when are you posting the answers? lol

posted on Monday, December 27, 2010 at 12:25 PM by Lauren MacEwen


I would like to answer the first question to show my presence here that an idea is gift from heaven. So we should trust on gift and focus on success by using that idea. Mostly people focus on failure so the got what they want. I am talking about positive thinking. 
Thanks & regards 
Lara William  
CompaniesManagement.Com

posted on Monday, December 27, 2010 at 1:42 PM by Lara William


What's the answer to question 12?

posted on Monday, December 27, 2010 at 2:03 PM by Nitin Pulyani


Put these up on Quora so we can all keep up!

posted on Monday, December 27, 2010 at 3:39 PM by Jasper


There must be an entrepreneurial motherboard that seems to root us all into the same thoughts or you're a very, very good psychic.  
 
Another one: between Twitter, Facebook, LinkedIn, blogs, ads, SEO and countless ways to market - what works best for my company and how do we get out there?

posted on Monday, December 27, 2010 at 4:55 PM by Kathy


I would like to give MY answer to Nitin Pulyani regarding question 12: If they aren't pulling their weight and performing the task/job they agreed to then they will drag the whole team down. Talk with them and either A: get a commitment to step up to the plate with measurable and mutually agreed to terms. If they don't perform you have no choice but to let them go or B: Perhaps they are overwhelmed or over their head. If there is a position or need that they can and want to fill then move them. I have found that sometimes we promote talented people to positions based on talents and performance but they don't like it or feel productive and would rather be in a previous position. 
 
My two cents worth. 
 
KJ

posted on Monday, December 27, 2010 at 10:03 PM by Kevin Jackson


My idea is good enough to help others but from where did I get funded for it ?? 
And why should people listen to me ??

posted on Tuesday, December 28, 2010 at 12:40 AM by Pradeep Kumar Kandala


 
1. Is my idea good enough to quit my job? 
If you had £500k in your bank right now, how much would you put into back your idea……..how much do you really believe in it. right now, if it gets passed that ask some of your more experienced friends (outside work probably) 
2. Should I try to raise outside funding? 
Only if you HAVE to. 
3. Did I make a mistake picking my co-founder? 
Yes if he is the yin to your yang and pulls his weight and delivers. Probably not if he is too much like you, and definitely not if he does not pull his weigh and does not deliver. Ask yourself could you do without him NOW. 
4. Is it wise to take angel investing from my Uncle Larry? 
Yes, just look Larry in the eye and tell him you will do your best BUT there are NO GAURANTEES……. 
5. Do I need office space to be seen as a “real” business? 
NO, you can do some fancy footwork when the investor prospectors come, but once you are over 3 people YES, but for YOU more than for 'face' 
6. I need help.  Is it ok to bring my spouse/sibling into the business? 
Depends………….. 
7. How much should I really worry about my company name? 
Worry about the reputation of your name, and what it means to customers…….worry about having a name that is unique if you want a ™, but other than that think of great brands and companies out of context…err.. Marmite, Nokia, sony, apple……..  
8. One of my co-founders needs cash to pay the bills, do we give him a salary? 
Whose bills? Do you get paid? everything must be equitable, and realistic for the company, and those involved. You must talk openly about it…… 
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? 
Ask the investors, why they did not invest (openly and nicely…..) and then adapt for the next group, you may even get an opportunity to fix something and come back. 
12. Someone from the early team is not as valuable as we though.  Should we let them go? 
"get the right people on the bus, and the wrong people off" quote from a good book. 
13. A customer wants to pay us a bunch of money for some custom features, what do we do? 
work out the ROI on doing it (Commitment to buy X volume on delivery?), and look at loss of opportunity in spending your time on this, also is this possible to sell on to others, will you learn anything? 
14. One of our competitors is getting all the publicity (and capital) -- but our product is better.  What do I do about it? 
Get a good marketer, and get on explaining WHY/HOW your product is better. 
15. I keep hearing about the importance of "work life balance", but don't know any successful entrepreneur that's pulled that off.  Is it a myth or am I doing something wrong? 
Myth 
16. One of our board members is a real pain in the ass, is there anything I can do? 
check the articles, and any shareholder agreements, and carefully find out who else thinks he is a pain in the arse. Then put a plan together for the companies benefit (not yours…..) 
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? 
First define what you want them to do, and then work with recruiters to find someone who can. Start with the Role not the candidate. 
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? 
First Why no longer passionate and if non retrievable then NO. 
21. There’s no startup ecosystem where I live.  Should I move somewhere there is? 
Find out what you need, and then look to see where you can get it. Nice warm and cuddly entrepreneur friendly places might make you feel better, butter honestly review if it will make your business better. 
22. How long should I work on my startup while I’m still employed by someone else? 
Only as long as you absolutely have to, and remember the most effective way to make a start up work is to have a PLAN B that is PLAN A, just with less time and less money and more pressure……….. 
23. I’ve been at it for a couple of years but nothing is happening.  What’s wrong with me? 
Nothing……but, now from what you have learned would you still answer question 1. with more than £100k………….. 

posted on Tuesday, December 28, 2010 at 1:20 AM by Richard Palmer


Question 1 is Key, and answer will tell you if you are ready to do this.  
 
The answer also depends on the tests, benchmarks, targets and requirements you set to answer the question.

posted on Tuesday, December 28, 2010 at 7:23 AM by Scopy


My answers (after 5 startups) 
 
 
 
1) If you have to think about this then probably not, or you can't afford to. 
 
2) Can you deal with the control they will want? 
 
3) If you're asking this, probably. 
 
4) No, unless Larry is an expert in what your doing or has a huge Rolodex 
 
5) No 
 
6) Maybe 
 
7) A lot 
 
8) No 
 
9) Find out from the non-buyer why they are not buying 
 
10) 
 
11) Assume you won't see checks 
 
12) Yes 
 
13) Take it, cash is king (try to build the additions to have utility outside just this Customer) 
 
14) Ignore them 
 
15) It's a myth 
 
16) Tell them they are 
 
17) Poach 
 
18) Competitors 
 
19) Will you be happy if you do? 
 
20) No 
 
21) Start one 
 
22) Until you can afford not to 
 
23) Wrong idea 
 
24) Outsource

posted on Tuesday, December 28, 2010 at 11:28 AM by Karl


I think those are reasonable questions, however; if we are talking about a startup, be it a small business or micro-business, many of those questions are a bit premature. Statistically, most startups in the U.S are sole-proprioterships where the founder has an idea that he or she will try and make a self-employed life doing something they love.  
 
 
 
That being said, I think it comes down to a few basic questions that are easier asked than answered, that is of course if one is willing to remove emotion from the equation, seek the facts, and listen to them objectively. 
 
 
 
I think in the planning phase, would-be entrepreneurs should focus on the basics. Does my product or service fill a want or need in the market, if so, who is my market and how do I tell them about what I have to offer them. 
 
 
 
I think much time will be occupied in answering those basic questions and will provide an additional bonus of completing a major section of the Business Plan, and answer the most important question of all.  
 
 
 
Do I have a viable idea worth spending any more time on. 
 
 
 
Good luck to all those who are thinking of starting a business. It is one of the greatest learning experiences I can think of.

posted on Tuesday, December 28, 2010 at 9:12 PM by MJD


thnak you for information. GüncelBlogu

posted on Wednesday, December 29, 2010 at 11:51 PM by byxmen


Great list of questions that I know are keeping up some entrepreneurs. Others that I have been asked are: 
 
Should I pay my employees first or pay my mortgage? 
 
Why can I not get a loan even though my credit is good? 
 
Why should I become 8a certified? 
 
Do I have to incorporate my business and why? 
 
Should I insure my business and how much should I get? 
 
Do I really need a website? 
 
Do I really need a business plan? 
 
 
 
Those are just some of the questions that I have been asked by small business owners and startup individuals. The answers to the first 23 questions and my list goes to the individual business owner and what their goals and needs are.  
 
If you are asking these questions, you need to be in touch with organizations that can help you address these needs. Seek out such organizations as Small Business Development Centers, SCORE, Women's Business Centers, and other business community type organizations who can provide the answers you seek through their technical support services. If you don't know where to go, check with your local chamber of commerce or the nearest Small Business Administration office. 
 
All the best for 2011!

posted on Saturday, January 01, 2011 at 12:25 PM by Karlene Sinclair-Robinson


Karlene brings up a very valid question for those who are thinking of starting a business, or even those who have an existing business. Do I really need a business plan? 
 
 
 
From the simplest Artisan-entreprenuer to the most complex multinational Corporation, I believe a business plan is vital for the long-term success of any company. 
 
 
 
An individual can possess some type of skill, and with a little luck, can do the right thing at the right time in the right place. And with those basic elements present, can even survive for a decade or so without a business plan. But when competition becomes an issue, the need for employes becomes necessary, and you find your accounting and finance system mismanaged among other things; the consequences of not having a plan will be felt. 
 
 
 
In my humble opinion, especially for those who are thinking about starting a business. Without a business plan, many vital business functions become ignored, mismanaged, or never conceived. And at some time in the future, that neglect will set an organization on a course to chaos or even failure. 
 
 
 
Additionally, formal sources of business financing are not available without a plan.

posted on Saturday, January 01, 2011 at 7:29 PM by MJD


Thank you for post. It is great article.

posted on Monday, January 03, 2011 at 3:25 PM by Misyon5ice


My Favorite one: 
 
 
 
If i did not quit my job and work on my idea, will i regret it in the future?

posted on Monday, January 03, 2011 at 4:50 PM by Jesal Sangani


Jesal, 
 
 
 
What are your thoughts on that question?

posted on Monday, January 03, 2011 at 6:22 PM by MJD


I'm not an expert entrepreneur, but my gut tells me if people you respect show a clear and genuine interest in your project, than it's worth it risking the downside to all these questions.

posted on Tuesday, January 04, 2011 at 2:19 PM by Nathan


I would like to say something about this blog. This blog is really informative and nice.

posted on Thursday, January 06, 2011 at 7:10 AM by Chij Gurung


Making a mistake picking the co-founder could set you up for never ending problems...

posted on Monday, January 10, 2011 at 2:36 PM by Printing companies in Gauteng


If there are 3 partners in a startup whose following is involved: 1-only monetary investment 2-whole time & effort 3-time as well as money. How should equity be divided among these 3 founders and how much to be reserved for future investors?

posted on Wednesday, January 12, 2011 at 7:50 AM by AnujaK


your blog is really informative thanks for posting

posted on Wednesday, January 26, 2011 at 12:55 AM by B.K panday


fix your web site 
 
 
 
Line: 28 
 
Error: 'document.getElementById 
 
(...)' is null or not an object

posted on Friday, February 18, 2011 at 12:06 AM by Didier


Just wanted to chime in with my thanks too.. great article 
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posted on Monday, February 21, 2011 at 4:23 AM by david hart


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