Startup Answers

Questions and answers about starting and scaling startups

Startup Risks and Careers at ESADE

The organizers at the ESADE Entrepreneurial Institute invited me in to speak to a collection of ESADE MBA and Master’s students. I spent some time in their “E Garage” startup lab, fielded lots of great questions, and had a great […]

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How should we plan at my startup?

  I encounter startup planning questions almost daily since most startups I work with struggle with the best way to plan and operate their businesses. I wrote this post somewhat in self defense – I needed a starting point to […]

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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 […]

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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 […]

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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 […]

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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 […]

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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 […]

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How do I avoid hiring “a–holes” at my company?

Fortunately there are not too many assholes out there, and I believe the startup world has fewer than its fair share, but a few assholes can do a lot of damage to a small company, so it is smart to […]

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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. […]

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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, […]

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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 […]

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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 […]

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What are the most common Saas pricing mistakes?

You will probably price your product too low. Don’t do that. Pricing is both art and science. It is possible to price too high, and it is possible to price too low, but several pressures lead to most entrepreneurs to […]

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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 […]

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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 […]

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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 […]

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What is a “Product Picker”?

“Product picker” is a term that I’ve heard Silicon Valley VCs use. I’ll explain the concept here since I think it really helps crystalize what kid of people a startup needs and how they should spend their time. Start by […]

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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 […]

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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 […]

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Should I “trust my gut” with hiring decisions?

A young startup founder who was struggling with a decision on a key hire recently asked me this question. I started to quote something that Jack Welch said on the topic. The founder interrupted me and said, “who’s Jack Welch?” […]

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Trip report from Failcon Zurich 2013

I am a very big fan of the Failcon (FailCon | Home) conferences. I spoke at Failcon 2012 in San Francisco and told the story of my last startup, ccLoop. I was then invited to speak at the inaugural Failcon […]

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Failcon 2012: “Social Proof is not Proof”

I hate failure. All entrepreneurs do. So do investors. So do employees and customers. We all prefer to work with and invest in successful teams. But hating failure doesn’t preclude embracing it, which is why I have always loved the […]

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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 […]

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Are you willing to chop holes in the floor?

Roger Ebert is one of my idols, and I follow him on Twitter religously. Ebert knows more about filmmaking than just about anyone, so when he tweets something like this, I pay attention: “The best video about filmmaking I tweet […]

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Don’t “Hire by Keyword”

“You have all these rules, and you think they’ll save you.” – The Joker, The Dark Knight I’ve recently followed a few discussions about “Hiring by Keyword:” A Quora post from a startup founder looking for a co-founder, but that […]

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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 […]

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Isn’t startup success largely about luck?

“90 percent of life is just showing up” – Woody Allen A debate always rages in the startup community: “are the successful people more talented than others, or have they just been luckier?” Successful people usually point to talent…they tell […]

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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 […]

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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 […]

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