The first truth of entrepreneurship and investing: The biggest new ideas are contrarian. They go so deeply against commonly held assumptions that they seem not only risky but flat-out ridiculous. They’re the kind of ideas that draw a lot of “Nos.” And this makes sense: The fact that an idea goes against conventional wisdom is…
Most of us love a great founding story. Whether it’s the founding of a corporation or the founding of a nation, we’re drawn to the dramatic stories where everything began. But I came to realize something, as I reviewed the past four years of Masters of Scale interviews in preparation for writing the new Masters of…
For the past four years that I’ve been hosting Masters of Scale, I’ve had the opportunity to meet entrepreneurs across many industries and from many walks of life. Their stories and insights have helped me change and broaden my own thinking in so many ways. But what these conversations also made me realize is that for…
The word ritual probably doesn’t conjure images of board meetings or product reviews. But effective business leaders create rituals for their organizations that can focus, clarify, and inspire. In the latest Masters of Scale episode, I discuss the power of ritual with Shishir Mehrotra, who tapped the power of rituals to grow YouTube, and now runs Coda.io,…
I was delighted to learn that WaitWhat, the startup company that makes my podcast Masters of Scale, is up for a few Webby Awards. There’s a popular choice vote that finishes tomorrow, Thursday. Initially, I resisted posting about it and encouraging people to vote; it felt too self-serving. But then I found out that Jessi Hempel is also up for a Webby…
Successful entrepreneurs have to find a way to combine both incredible patience and explosive speed. Sounds paradoxical? Perhaps, but that same, seemingly conflicting combination has powered the success of fashion designer Tory Burch. In this episode of Masters of Scale, you’ll hear how Tory’s remarkable story combines patience and speed. You’ll hear how Tory went from a tomboy who…
How I’m working with Harvard Business School Online to teach the counterintuitive truths of scaling up As a founder, you rarely have enough time to step back and strategize. Entrepreneurs feel the pressure to execute, often prioritizing daily firefighting over long-term planning. You put your blinders on and stay laser-focused on what’s directly ahead. But…
I strongly believe in the power and importance of diversity. That’s one of the reasons why Masters of Scale was the first American media program to commit to a 50/50 gender balance for its guests. But a nuance that is often missed is what it’s like being the person who provides that diversity. Sallie Krawchek, my guest…
Since launching the Masters of Scale podcast, I’ve interviewed more than 50 amazing entrepreneurs, and helped them share their experiences and lessons from building iconic companies. Now, for the first time in the history of the podcast, the tables have been turned. My friend June Cohen, the co-founder of WaitWhat, the company behind Masters of Scale, steps out…
When people think about Google’s greatest assets, they usually picture Search, Android, or Gmail—market-leading products that hundreds of millions of people use every day. These are great products, but I believe that Google’s most overlooked “crown jewel” is actually a management training program. Of course, calling Google’s Associate Product Manager (APM) program a training program…
One of the great paradoxes of entrepreneurship is that you have to pursue an opportunity with 110% commitment, but be willing to pivot at a moment’s notice. As the great philosopher Kenny Rogers pointed out, you’ve got to know when to hold ’em and know when to fold ’em. Stumbling over this paradox caused my…
If software is eating the world, it’s using the marketplace model as the fresh cracked pepper to flavor its meal. Services from Uber to Amazon’s Mechanical Turk promise to layer clean, systematic APIs on top of messy human interactions for greater efficiency. Yet while economics papers might model human beings as Homo Economicus—a hyper-rational utility maximzer—in the real…
Companies need different kinds of leadership at different stages. And there’s a very specific kind of leadership needed in an organization that’s changing fast — so fast that the office you leave at night is different from the one you walk into the next morning. I believe to lead this kind of organization to scale,…
Over the last 20 years, I’ve worked on or invested in many companies that scaled to 100 million users or more. And just about every entrepreneur I meet with has that ambition as they get started. But here’s the thing: You don’t start with 100 million users. You start with a few. And in many…
There’s a myth amongst entrepreneurs of the “lightning strike” — the “aha” moment when an idea just comes to you. In reality, it’s rare to find a successful scale entrepreneur whose big idea landed on their lap. It’s more likely they were already on the hunt. If you want to find your big business idea,…