There’s an old joke in software development, “How much time does it take to design software?” Answer: As long as you have scheduled for the design phase.

I know. Not funny, “ha, ha” but pretty apropos.

If you’ve been involved with a number of software projects you already have an intuitive sense for this. We’ve all been involved with projects that seem to drift and drift and make progress. There’s a healthy balance between allowing a design team to dream up functional requirements, talk with customers, analyze competitors and for technical projects – research the latest cool-kid tools to play with.

Design with no constraints becomes a research project.

You see there is a creative tension along the spectrum of  time and scope. If you pull too hard at the scope end of the chain your time drifts. If you pull hard at the time end of the spectrum you end up shipping inferior product. As obvious as it seems I assure you that many projects I’m involved with don’t sit down and have hard enough conversations about the need to hit time-based deadlines – so dates slip.

CEOs are time-driven creatures. We feel pressure to hit milestones for a variety of reasons: Investor presentations, conference demos, customer sales meetings, competitive pressures, a need to drive revenue, business development commitments – whatever. CEOs who are tough but fair-minded set aggressive targets on “time” and communicate clearly with engineering why there is a deadline.

We live in an era of more product-dominant companies where a perfection complex for features and design delay business realities of shipping products.

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One of the hardest things for most entrepreneurs to know is how hard to push in situations where people tell you “no.”

But then again most entrepreneurs fail. There is that rare breed that doesn’t accept “no” for an answer. It is impossible advice to give because there is such a fine line between being persistent and being annoying and it’s something you probably can’t teach. I often describe “chutzpah” as being able to skate right up to the line of acceptability without crossing over it.

And being persistent I believe is the most important attribute for success in an entrepreneur (assuming of course that you have all the other requisite skills).

Years ago I started using the term “politely persistent” to remind people that you still need to be likable even if you have gumption.

I’d say less than 20% of of entrepreneurs fit into that bucket.

Of course at one end of the bucket are entrepreneurs who are persistent but just aren’t polite.

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Most people suck at presenting to big groups.  It’s a shame because the ability to nail these presentations at key conferences can be once-in-a-lifetime opportunities to influence journalists, business partners, potential employees, customers and VCs.

So I thought I’d write a piece on how not to suck when you give a presentation.

1. Show some energy! – No great presentation can be delivered like a conversation.  You’re not lecturing to a college class, you’re not at a cocktail party and you’re not chatting with a small group in a board meeting.  You’re on stage!

People are sitting in their chairs for too long – most of them squirming.  Many of them have their iPhones and laptops ready to command their attention the moment that you start sucking.  You’re on stage – act like it!  Get out of your comfort zone.  You need to be an order of magnitude more perky than you would feel comfortable with in a normal conversation.

Project your voice.  Use your hands.  Don’t mumble.  Speak quickly sometimes.  Speak slowly to emphasize a point.  This is called “vocal variety” and it’s critical.  Speaking in a monotone voice is, well, monotonous.

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CEO transparency. It almost sounds uncontroversial. A CEO should tell her staff everything! Right? Right?!?

Of course not.

It’s a hard topic to write about because it’s almost an accepted norm that total transparency is good. It is not.

For starters let me use “CEO” as a proxy to include her “inner circle” which might mean co-founders or might just mean senior execs of the business. I do believe in total transparency with your core.

The Mind of the Founder

You took the risk to start your company. You quit your day job and look the leap off of the cliff. It’s so much scarier than most people admit – even to themselves.

Scary why?

All of a sudden you know you’re going to be judged.

Your parents want to know why on Earth you’d leave a job at Google. “Honey? Aren’t they worth billions of dollars?” “Yeah, Ma. But I’m working on a large team of people trying to figure out how to make micro improvements to a paid-search algorithm. Fun stuff, I know, but it’s time for me to try something more stimulating.” “Oh, OK, Honey.

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My internal compass has always steered me strongly toward the belief that founders who can scale with their startup companies are better to back that founders who eventually need to hire a CEO.

I have talked about this publicly a great deal – how I prefer “missionaries” over “mercenaries.”

But lately I’m more swayed by the wise words of Reid Hoffman.

“Founder is a state of mind, not a job description”

We all love the mythical stories of our great founder heroes who drove startups from scratch and led their businesses many years later: Bill Gates, Larry Ellison, Jeff Bezos and so on.

Very few founder CEOs go into the job ever expecting to give up their seat. It’s your baby. Your idea. You took the biggest leap of faith. It becomes an extension of self rather than a job.

So give up the CEO role?

Fuck no.

But it’s actually not that simple.

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The one word the best entrepreneurs never accept.

I said it.

Now let me walk you through a broader story because avoidance of the word in and of itself will seem cliche. Stay with me.

When I was little I had a role model for entrepreneurship – my mom. She was a natural leader. She was president of the UJA in Sacramento. From this I saw civic involvement and leadership first hand.

She was a nurse but was never graduated from a 4-year college. Still – she can do the NY Times crossword puzzle better and faster than I. Even today.

She was a hustler. And a ball buster. And a natural sales person. She was never afraid of the word “no” even to the point of embarrassing me.

My youth was filled with her arguing with vendors if they tried to pull a fast one. As my wife will tell you – arguing is cultural – you grow up with it or you don’t. I did. It’s very Jewish. For better or worse. She’s learned to embrace it in me.

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