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Archive | In the Ring

Betting Against the American Dream (in San Francisco)

My friend Matt Pasienski, a Physics PhD, just announced he’s moving to Mexico and leaving San Francisco behind. Here’s what he wrote: The American Dream has moved to Mexico. If you work hard in Mexico you can buy a house, have a family, and live a good life. That’s not something I can see happening in San […]

You’re always gaining credibility… or losing credibility.

“Should we fire the CEO?” That’s the question at the heart of every board meeting. It’s the only thing I can really do as a board member, really. Even if I never say those words, the question is always in the back of my mind. -Anonymous Board Member & Entrepreneur A founder called me today. His lead investor was in the news […]

Getting Unstuck

“The only difference between Elite Entrepreneurs and those just getting started is the amount of time we stay stuck.” –Dan Martell Winning is all that matters. You only have to get to the top of the mountain once. How much time you spent falling down at the bottom beforehand doesn’t matter (other than the opportunity […]

Letter to a Fired Founder

A friend of mine just got fired from his startup. As a founder, he was classy, loyal and relentless. He behaved like a champion. But despite all this, he got shitcanned nonetheless. So I wrote him a letter: Hi, I know you must be feeling pretty shitty right now. Probably a little bitter too. I know I would. [!Name], I’ve […]

Ask for the Money

I have a technique for asking investors for money. At the end of the pitch meeting, I ask: “So… are you in?”  It’s that simple. If you’re a founder and you’re raising money for your startup, you need to ask for the money at the end of the pitch meeting. Cuz if you don’t ask, […]

No One Is Self-Made

Fatherhood has changed me. In my pre-fatherhood twenties, I thought of myself as a self-made man. I viewed the world through an individualistic, narcissistic lens and my accomplishments, I believed, were largely my own. I had taken risks and busted my ass to get whatever I got. I congratulated myself and began — quietly — to scorn those who had […]

Mission Driven Companies Do It Better.

Mission driven companies do it better. They execute better. They scale faster. They grow quicker. In my first company, we were anything but mission driven. And this caused us huge problems. If you had asked 5 people in the company, “What does your company do, exactly?” you would have gotten five very different answers. Each employee, each founder […]

Announcing Marketplace Talks: On-Stage Interviews With The World’s Best Marketplace Entrepreneuers

I’m proud to announce my involvement in Marketplace Talks, the world’s #1 meetup for marketplace startups, entrepreneurs and investors Once a month, I’ll interview a prominent marketplace entrepreneur (or investor) on-stage, in front of an assembled mass of other entrepreneurs, investors and startup people. I’ll do my best to dig into the business model, how it […]