Leadership


A shortened, better edited and with nicer pictures version of this post first appeared on TechCrunch. But if you want it in it’s full V1 glory read on …

You’ve never been a CEO but might like to be one some day. But how? Nobody sees you as a CEO since you’ve never been one? I wrote this conundrum and the need to take charge of how the market define your skills in my much-read blog post on “personal branding.”  If you don’t create the message about yourself, the market will. And if you want to be a CEO one day you need the messaging to reflect that.

The strange thing is that once you’ve been a CEO even one time the market will see always see you as a CEO but nobody really wants to give a new-comer chance.

Of course you could start your own company. For many people that’s the right answer. As I talked about in “Is it Time to Learn or Time to Earn” – overwhelmingly the best economics go to those that start successful companies. But not everybody has the right skills to build a highly successful and valuable startup from scratch. In fact, I would argue that most people don’t.

The decision tree for being a startup CEO begins with whether you can sustain 12-18 months of little or no salary while you define your market, do research, build v1 of your product, raise seed funding, attract your initial team, get your first customers and test whether you have initial product / market fit or enough momentum to be able to raise a large round of capital.

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Obsession. The drive to succeed at all costs. When second place isn’t good enough because we live in winner-take-most markets. The desire to be better than anybody else in one’s field.

This blog started from a series of conversations I found myself having over and over again with founders and eventually decided I should just start writing them.It would often make my colleagues laugh because they’d hear me like a broken record and then the next week read my ramblings in a post.

Last week’s obsession was about obsession itself.

10 days ago I saw the film, Whiplash, which is one of my favorite films of the year. I would be shocked if it doesn’t win at least one Oscar. I won’t have any spoiler alerts here, don’t worry.

The protagonist in the film, Andrew, is a drummer and the story is his experiences in his freshman year of one of the most elite music conservatories in the country. He wants to compete to be the lead drummer in the competitive ensemble and study under Terence, an obsessive instructor who is hell bent on winning competitions for the school.

I absolutely loved the film. I loved the music.

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One of the vivid memories I have from being a startup CEO is the feeling that most people in your company have a look in their eyes that like they can do your job as well as you. How hard could it be? You just assign out tasks to all of us.

In the early days the CEO is the jack-of-all-trades, doer-of-all, famously the “chief janitor” or coffee maker. But if you level up, raise capital and grow customers, revenue and staff – life changes. Eventually you need a VP of Product to handle your product roadmap, a CTO for engineering leadership and VPs of sales, marketing & biz dev. Most companies that are scaling have CFOs, heads of HR or talent. The “span of control” for a growing tech startup is probably 6-9 people. The “doers” in your organization.

This is when your job function truly starts to match the definition of “leader” because that’s exactly what your role is. You set direction. You hire great people. You help them prioritize their objectives and review the results. You course correct. You motivate, cajole, reassign tasks, hire, fire and push the organization forward.

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Just back from vacation and also some work travel and want to get back to blogging so expect a few posts over the next couple weeks.

During my absence I posted a couple new episodes of Bothsides TV recently. I’ll try to get write-ups shortly but for now here is an overview of my interview with Nanea Reeves – President and COO of textPlus. I could have listened to her for hours as many of her lessons were ones I hadn’t heard before such as how she used online gaming when she was younger as a way of both teaching herself tech as well as learning to lead remote teams.

Just so you know I work directly with Nanea and her arrival last year at TextPlus as President & COO has been transformational for the company. I’m sure I would speak for the entire board and management team in asserting this. I’ll try to do a future blog post on some of my insights in watching Nanea enter the role and how the founders enabled her success.

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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.

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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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