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Source: https://news.yale.edu/2017/02/10/grace-murray-hopper-1906-1992-legacy-innovation-and-service

Software is at the core of most high-growth venture-funded tech startups. Great software is built by great people, so the leader who attracts and manages those great people is foundational to any startup. A startup can’t be great without a great VP of Engineering.

Some startups are lucky enough to have a technical co-founder who has done the job or can grow into it, but most high-growth startups will at some point find themselves recruiting a VP of Engineering from outside of the company.

It’s not easy, but it can be done.

I’ve been a VP of Engineering (VPE) at several companies I founded as well as at a public company. I’ve been recruited as a VPE a few times, I’ve participated in hiring several VPEs, and I’ve participated in a couple of dozen other executive searches. …


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I am a creature of the San Francisco tech bubble.

I live in a city full of people who work at startups or at tech giants like Google. At their workplaces, talent is scarce, job security is high, and benefits like free lunch and laundry service are de rigueur. They are early adopters of technology, often carrying the latest gadget or debating a hot open source project. They are almost all college graduates, many are immigrants, and most of them make a good living. …


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Source: “It’s a Wonderful Life.

When I first started managing people in the mid-90s, I knew a lot of other up-and-comers who were also taking their first management positions in the pre-bubble startup world (picture the newly-minted Stanford MBA crowd). Over drinks, we’d share management “wisdom” with each other. The first nugget we all agreed on was, “I tell people who work for me that when they bring me a problem, they also need to bring me a solution.”

Intuitively, this felt right to us, and we were convinced that our gang of 20-something Bezos wannabes had cracked the code of management. Of course you want to challenge your team to solve problems and not to just come running to the boss to complain. “We want doers, not whiners!” …


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Photo by Gabriel Barletta on Unsplash

“The execution is more important than the idea!”

“The best startups are execution machines!”

“Execute! Execute! Execute!”

Since you are reading this post, you are probably a startup founder or team member who reads lots of startup advice, which means you’ve seen many admonishments about how your startup must “execute.” It’s no surprise — although you might find a few exceptions, most successful startups execute extremely well, in addition to having a great idea (or pivoting to one).

But a piece of advice being true doesn’t always make it useful. Telling a startup team, “you need to execute!” is like telling a basketball team, “you need to score more points!” (thanks, coach!). Startups need help learning how to execute. Most founders have never managed a complex organization; many have never even worked at one. Startups are so difficult that just surviving the week can feel like a challenge, much less delivering “flawless execution” along the way. …


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Photo by Markus Spiske on Unsplash

Did you know that Craig Newmark destroyed journalism?

Craig the Destroyer was mentioned, as he often is, on one of those “the state of journalism today” podcasts I listened to recently. Newspaper old-timers were telling tales of the good old days, before the late 1990s fin de siècle, when Craigslist knocked out one of the pillars of their business model, classified ads, ending their days of high margins and martini lunches forever. They’ve been cursing that schlubby, beret-wearing nerd perched in his foggy second floor Sunset District walkup ever since.

Even Newmark’s 2018 donation of $20 million to the CUNY School of Journalism did little to redeem him. It was met with eye rolls since, don’t you know, journalism schools wouldn’t need rich benefactors in the first place if guys like Newmark hadn’t gone and destroyed journalism in the first place. …


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Photo by Ant Rozetsky on Unsplash

This post is one of a series which covers common questions about where startups come from, how they work, and how to navigate a career in the startup world.

Q. I hear that people at startups work like crazy. Is that true?

Startup teams usually work hard, and if you drop by a typical startup office you’ll see something that looks a lot like it: an office buzzing with activity, energetic young people bouncing between meeting in always-booked conference rooms, and long hours late into the night and over the weekends.

That is not to say that startups work uniquely hard: a typical medical resident, law firm associate, PhD candidate, or Wall Street analyst probably works even more hours and has less day-to-day freedom. But it’s true that startups aren’t a great career for someone who wants an easy nine-to-five existence. …


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This post is one of a series which covers common questions about where startups come from, how they work, and how to navigate a career in the startup world.

Q. How much information should a startup share with its team?

Probably more than you think.

Startups are hard, and most fail. To have even a shot to succeed, a startup has to solve some very tough problems, all of which are easier with a culture of transparency:

Getting great people to join. Startups win when they have the best team. Competition for the best people is fierce, and the best people will only join a team where they can learn quickly, have autonomy, and are treated like adults. They simply won’t join a company if the leaders keep them in the dark. The best people are ambitious and want to learn quickly and contribute to the best of their abilities. …


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This post is one of a series which covers common questions about why startups exist, how they work, and how to navigate a career in the startup world.

Q. I know startup culture is important, but can you really control it?

Most startups know that culture is important, but they find it elusive: it seems hard to define and even harder to control.

But it doesn’t have to be that way.

To illustrate, imagine you start a company with two other co-founders. One of you is the CEO, one is the CTO, and one focuses on customer acquisition. You hire a few engineers, a designer, and an office manager. …


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The stacks of the New York Public Library (http://exhibitions.nypl.org/100/learn/fun_facts).

This post is one of a series which covers common questions about where startups come from, how they work, and how to navigate a career in the startup world.

Q. Why do startups exist? How can a billion dollar company pop up out of nowhere while established companies miss the same opportunities?

The five most valuable companies in the United States are technology companies less than forty years old. More than a hundred other public and private unicorn tech companies are valued at more than $1 billion, most of them less than ten years old.

Most people don’t understand why this happens, so they find themselves on the defensive. They miss new opportunities or see their careers stagnate as their companies are disrupted by newcomers. …


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Courtesy of “Oaky the Truffle Pig”

This post is one of a series which covers common questions about where startups come from, how they work, and how to navigate a career in the startup world.

The most important job at a technology startup is one that you probably haven’t heard of: the “Product Picker.”

To illustrate, imagine you are an investor and a company with two co-founders walks into your office to pitch you on their new startup.

The technical co-founder is a wizard. She has been building apps since grade school, has godlike status on Github, and can do anything from high-level architecture to hands-on coding. …

About

Michael Wolfe

Co-founder, Gladly. Advisor at Point Nine Capital. Five startups. Endurance athlete, SF dweller. Quora addict. Fanboy.

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