Play it safe should be an oxymoron when mentioned together in the sentence with a startup. There are so many unknowns and unknown unknowns with regards to customers, employees, investors, technology and everything else in a startup, that forecasting is even more futile than usually. While most of the stories in the news on startups talk about either catastrophic failures or giant successes, it is the middle ground that it is the most frustrating. When you have no customers and no income, it is easy to admit failure and change course. And if your coffers are full of money or you are a hot startup with a long line of potential investors, you'll survive even if you miss your sales by 30%. But if you have just enough revenue and market traction to survive but not thrive, it is much harder to take risks. You've spent years of hard work on the endeavor and you're terrified to blow it up. But @cagan said it best: "If your key performance indicators have flatlined you are already a failure."
There comes a time in every company where the leader or founders have to decide whether they are going to take a big risk or play it safe. I met with a founder last week that was telling me about his frustration with his company. Things are going very well considering but he can't get the team to take risks.
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