What’s the Hardest Startup Lesson You’ve Had to Learn?

Running a startup gives you a crash course in everything from customer development to figuring out how to work at Starbucks without getting kicked out. We asked startups: what’s the hardest lesson you’ve had to learn?

The insights varied, from marketing and funding to more personal lessons about community and failure. Here are some of the best ones.


“When you estimate the time it will take to bring your product to market and the cost to develop it, at least double both of those to start getting close to reality.”

– Mark Snow, CEO of SafelyFiled


“Just because you build it and are excited about it, doesn’t mean you will hear anything but crickets when you first start out! Launch is only the very beginning.”

– David Winchell, founder of WHO I CHOOSE


“It’s important to build out your recruiting pipeline long before you need to hire. I’m always recruiting. Even though we don’t have immediate hiring needs, I make a point to try and get out there and get to know awesome people.”

– Sonia Sahney Nagar, cofounder and CEO of Pickie


“Deal isn’t done until the money changes hands.”

– Chris Chattin, CEO of Netcamps


“The passing of Jody Sherman here in Vegas and the reality that startups don’t really get the support they need until it is often too late.”

– David Gosse, CEO of Tracky


“Prioritize, prioritize, prioritize. It takes an obscene amount of willpower, but it’s unquestionably best for the business if you can focus your energies every day on the one to three things that will most move the needle for your company.”

– Bernie Yoo, cofounder of Bombfell


“Sometimes ‘big’ companies are afraid of the ‘little’ guy.'”

Lucky Orange


“I, we, all of us make mistakes on a daily basis. . . . Make the mistake, own it, and move on – FAST.”

– Rick Gilchrist, cofounder and COO of iDEAXIS

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Written by:
Kira M. Newman is a Tech Cocktail writer interested in the harsh reality of entrepreneurship, work-life balance, and psychology. She is the founder of The Year of Happy and has been traveling around the world interviewing entrepreneurs in Asia, Europe, and North America since 2011. Follow her @kiramnewman or contact kira@tech.co.
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