Here's why investors shouldn't give entrepreneurs advice, according to an investor who made early bets on Uber, Warby Parker and 80 others

Scott Belsky

Scott Belsky is an entrepreneur and angel investor who's made more than 80 investments.
He's written a book on the struggles entrepreneurs encounter during the difficult, bewildering years when their companies are striving to make an impact.
Among his key takeaways: Investors should stop giving entrepreneurs advice in their hours of need. Instead, they should craft questions to help guide them.

As both an entrepreneur and longtime angel investor, Scott Belsky has carefully considered the journey of the typical startup founder. After Belsky's software company, Behance, was sold to Adobe in 2012 for a reported $150 million, he took over as Adobe's chief product officer.

Now, Belsky is reflecting on the experience he's gained as both an investor and a startup advisor in his new book, The Messy Middle, which deals with the long, often bewildering period in which a struggling startup strives to make an impact.

"One of the reasons I wanted to write this book was that I felt that I'd been privy to so many journeys," said Belsky. "There's been so many 1 a.m. phone calls, or texts from a founder that say, 'Hey, do you have a few minutes today?' That's when you know they're either contemplating an M&A, or that they're shutting down — these major moments when they're struggling to know what to do."

When asked what advice he offers up in those hard moments, Belsky said that his role is to help the founders figure things out for themselves.

"The only way to help someone out in these moments is to ask questions that the entrepreneur might not have thought about," said Belsky. "Great advisors prompt the right questions. An entrepreneur has to choose what path they climb, but as an advisor, you have to illuminate the situation. Are they making decisions out of fear or ego? Asking the right questions is probably the greatest contribution an advisor can make."

But there's lots of advisors who overstep their role — many entrepreneurs deal with investors and board members who either offer up too much advice, or believe that they know the best path for the company.

This, says Belsky, might be sign that the entrepreneur should seek out other guidance.

"A lot of bad investors are probably the ones that hand out the strongest advice," said Belsky. "It's easy to be an investor and sit back in your chair and say, 'Here's what you should do.' But most investors don't know what to do —or they've never gone through the task of executing. The best investors know better than to give out advice. They pose the right questions at the right time."

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