Building a Successful Startup Is Like Playing Smart Poker

You don’t want to be the gambler. You want to be the grinder.

Don’t follow the system

One of the first things I have to teach new entrepreneurs is that there is no system for success. It doesn’t matter what type of company you start, the customers it sells to, or the price point of the product. If the entrepreneur follows a system or a template or a checklist, the startup is going to fail or, at best, stagnate.

Opportunity always beats acceleration

Opportunity is a slow and steady slog. Acceleration is a fast and sexy sprint. But if there is no defined opportunity, acceleration will just drive you into the ground. Or if the opportunity is misguided, acceleration will move you very quickly in the wrong direction. Both of these things will lead to failure.

Don’t bet on the macro

There are very few macro changes in the economy, the business world, or society that will impact every company equally — and we happen to be living one of them right now. The last economic shift of this magnitude was probably 9/11 or maybe the Great Recession. So think of it as a tectonic shift every 20 years, with the occasional near-miss every 10.

There is no such thing as overnight success

Windfalls are amazing, and they’re the lifeblood of all entrepreneurial strategy. They can be financial windfalls, marketing windfalls, positioning windfalls and even hiring windfalls. But no windfall sticks without putting in a shitload of work to build on the momentum until the next windfall comes along.

I’m a multi-exit, multi-failure entrepreneur. Sold ExitEvent. Building & GetSpiffy. Former Automated Insights. More info at

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