Jan 21st, 2020

What a Super Bowl Ad Can Teach You About Leadership

A little while ago I found myself on a conference panel with David Barett, founder of Expensify. There is a lot to be said and learned from David and his uber-successful company — anything from his leadership philosophy (parts of which we have discussed here already). But the thing which stuck with me was his story about Expensify’s Super Bowl ad.

If you know anything about the Super Bowl, you know it is one of the most watched sporting events in the world and one of the most expensive and prestigious advertising venues. Spots during the Super Bowl TV broadcast are sold long before the game starts, at a staggering $175,000 per second of airtime. Typically these spots are booked by fast moving consumer goods, food and car companies — who are in the business of selling products largely to average consumers in average households. 2019 was the year David decided to add his expense-reporting software to this illustrious list of companies.

As much fun it would be to talk about the TV spot and its impact on Expensify’s business — this post is about the question how David got this all started in the first place.

See — David had this crazy idea (seriously, it is a crazy idea for a company as his to have a Super Bowl ad). He brought it to his team and he did something magical: Instead of having people, such as his marketing team, debate the merits of a Super Bowl ad, weigh all the pros and cons and essentially discuss “should or should we not”, David framed the question differently:

“How are we going to make a Super Bowl ad and make it work for us?”

By simply framing the question as a “how” question, he challenged his team to come up with their best and most creative thinking (and not engage in a “if/should we” debate). Question centered around finding the money to pay for it, to the ad itself, to the way you leverage the ad in ways which make sure, that the endeavor makes financial sense.

The next time you want to challenge your team, colleagues or even your family to do something outrageously ambitious — instead of asking if/should we, go straight to the how. It still might turn out that there is no conceivable way to get it done; but at least your discussion centers around creative solutions to the problem and not a debate which ends up being a simple yes/no.

Jan 9th, 2020

The One Percent-Rule

Today, my colleague Mafe sent me an excerpt from an article she read:

”We can call this The 1 Percent Rule. The 1 Percent Rule states that over time the majority of the rewards in a given field will accumulate to the people, teams, and organizations that maintain a 1 percent advantage over the alternatives. You don’t need to be twice as good to get twice the results. You just need to be slightly...

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Dec 3rd, 2019

Everybody Either Writes Code or Talks to Customers

Earlier this week I had a delightful conversation with Expensify’s founder and CEO David Barrett at the Digital CPA conference in rainy Seattle. We talked about all things culture, innovation and how to bridge those two spheres in front of a group of leaders and CEOs. When asked about his company (which is a/the leader in expense management software and a happy unicorn) and how he keeps people working on the right things (namely:...

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Dec 3rd, 2019

Know Everything There Is to Know

If you have seen my last post, you know that I recently read Blake Snyder’s excellent book on screenwriting “Save the Cat”. It is a great (and fun) read which made me think about storytelling in a different way (especially in the context of pitching a business and my specific craft: Storytelling from stage). Plus it makes you see movies through completely different eyes – the Blake Snyder Beat Sheet.

In the book, Blake...

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Dec 3rd, 2019

What Screenplay Writers and Startups Have in Common

In one of the best scenes of the 2001 documentary Startup.com (one of my favorite docus – watch it!), you watch as the founders of the staring startup govWorks pitch potential names for their company to random strangers in a döner kebap shop in NYC. It is a brilliant example of some of the best and most valuable things anyone who is building something new can do: Get out there and road test your stuff.

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Nov 22nd, 2019

Freedom in the System

As you scale your business, you start putting systems into place. They take the form of processes, procedures, rules and regulations. It is, in many ways, the only way you can scale beyond a handful of people. But if you are not careful, you create not only bureaucracy but will stand in your own way.

Take my recent experience with America’s beloved airline Southwest. For better or worse I have frequent flyer status on Southwest...

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Nov 16th, 2019

On Paradigm Shifts

I just returned from the Rise of the Rest Summit where I had the distinct privilege of meeting some of the most inspiring, hard-working and smartest entrepreneurs around. In the evening I had an inspired conversation with a blockchain/crypto-assets entrepreneur about public equity markets, why they evolved into their current state of affairs and how a future decentralized system might look like. In the midst of our discussion the entrepreneur tried to explain the...

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Nov 11th, 2019

The 90 Minute Rule

The other day I had the distinct honor and privilege to spend more than an hour talking with LinkedIn’s CEO Jeff Weiner on stage at a Singularity University program. We touched upon many topics, the highlights of our conversation being beautifully summarized by the one-and-only Stephanie Crowley Papaioanu:

Graphic Recording

Among the many great comments, the piece which stood out for me was Jeff’s answer to a question from...

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Oct 21st, 2019

Learn to Read Weak Signals

An exercise I love to do in my talks recently, is to show folks the following chart:

Mobile Phone Usage

What you are looking at is the usage of mobile phones vs laptops/PCs and other Internet-connected devices over time in the USA. The question is: Imagine we are at the end of 2008 and you only know about the data for this year. Mobile usage is the tiny, red chevron you see...

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Oct 7th, 2019

Welcome to BBS (Business Bull$#!%)

I am traveling a lot these days. And with travel come long hours in airports and sometimes airline lounges. And pretty much every time I find myself in one of those, working away (or just zoning out), I inevitably overhear someone talking loudly on the phone. You can tell within seconds that it is a “business call”. Words such as “strategic relevance”, “cross-reference” or “best practice” get tossed around. Clients get called names in a...

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