Questions and answers about starting and scaling startups
Do I need to be a “jerk” to succeed at a startup?
Startup founders and executives at growing startups often ask this question for a few reasons: A new generation of Silicon Valley critics (I’m looking at you, Valleywag) is slapping the label “jerk,” “asshole,” or even “psychopath” on any startup leader […]
How can we make faster and better decisions at my startup?
A common complaint at fast-growing startups is, “why are we having so much trouble making decisions?” Frustration around decision making typically starts after the company has reached a breaking point where it has become too large to just let decisions arise […]
Is it possible to stay healthy while starting a company?
Startups are all-encompassing. Many people avoid them because of the horror stories of 100 hour weeks and personal stress they have heard coming from founders. But there are plenty of counter-examples. I’ve worked at startups as an exec or co-founder […]
Why do angels and VCs not seem to care about profits?
The behavior of tech investors baffles many people – why do they put money into businesses that have no profits in sight? Tech investors do care about profits. A company that cannot eventually generate profits has little value. But tech […]
Why are startups able to outmaneuver large competitors?
Someone asked me this question on Quora recently, asking specifically about how mobile security startup Lookout was able to beat all of the established incumbents in the security space, especially McAfee and Symantec. It is a very interesting question since it speaks […]
Why are so many acquisitions such a disaster?
Acquired startups face a bunch of challenges in the first place: Many of them would have failed anyway, without the acquisition – most startups fail, and many acquired ones were nowhere near the critical mass required to give them their own momentum. […]
How does a non-technical person get a job at a startup?
You need two things: a story and someone to listen to it. The story is, “a startup that needs X can use me because I’m awesome at X.” So what is your story? A few possibilities: “I can sell and hustle like crazy. I’ve spent my life in sales jobs (waiter, […]
What are some signs you are working at a “sinking ship” company?
Large Company Edition New opportunities are framed in terms of how they impact the existing legacy businesses, not how they impact the customer and the future. Mediocre employees are not fired since you can’t recruit better ones anyway. You benchmark […]
What are the biggest “people” problems that a startup faces?
Almost all startup problems, especially after a company starts to scale, are people problems. Most fall into a few areas: Turning recruiting into a discipline – it is very hard to recruit great folks. I talk to companies all of the time […]
Why is Dropbox more popular than other programs with similar functionality?
Well, let’s take a step back and think about the sync problem and what the ideal solution for it would do: There would be a folder. You’d put your stuff in it. It would sync. They built that. Why didn’t […]
Is it true that the best startup ideas seem terrible at first?
The best startups seem obvious in retrospect – this is because by the time we found out about them as users they had already reached critical mass. It is possible to create a good startup with a good idea, but great startups are often the result […]
Why are software development estimates regularly off by a factor of 2-3 times?
Let’s take a hike on the coast from San Francisco to Los Angeles to visit our friends in Newport Beach. I’ll whip out my map and draw our route down the coast: The line is about 400 miles long; we […]
Do I really need to do 1-1’s with my team members?
I get this question a lot – most startups are just scrambling to ship products and close deals before they run out of money. Spending a few hours a week sitting in meetings can feel like a big-company practice that […]
How do I know if my software idea is large enough?
It is relatively easy for software entrepreneurs to find customer problems they can solve, but it is hard to know which ones are large enough to truly build a viable business. A starting point is to accept that the upper […]
If you want to be Big Time don’t act like Mr. Big Time
Last month a venture capitalist I haven’t met reached out to me asking for a meeting. He sent me a one-line email that said, I’d like to meet you. He didn’t ask me if I wanted to meet him. He […]
It is “all about the people.” But do you act like it?
Chris Dixon wrote an excellent post that I believe will be influential: http://cdixon.posterous.com/things-id-do-if-i-ran-a-big-vc-firm One item Chris touches on is investors making more of an effort to know and help the teams in their portfolios so they can work with them […]
Should I start my career at a big company or a little one?
I did a talk at the Computer Forum at Stanford a couple of weeks ago that I thought went well: it was a seminar for engineering grads and undergrads about career paths and how to navigate them. I thought I’d […]
I want to get into the startup world – what should I read?
“Those who know, don’t say. And those who say, don’t know.” – Da Mayor, Do the Right Thing, Spike Lee Several folks have come to me lately who are fleeing sinking ships strategically assessing career opportunities, and many ask me […]