“Failure is likely, but I’m not operating like it is”: How to balance hope vs reality

The chances of startup success are slim. Ninety percent are destined to fail. You know two things: that you’ve got a one-in-ten chance of success, and that you have to have the utmost confidence in your company.  

How do you balance hope with reality?

Chris Hutchins is an Entrepreneur in Residence at GV who previously co-founded Milk with Kevin Rose in 2011. Milk was a mobile development lab that was acquired by Google a year later.

Having originally started his career as an investment banker and then management consultant in New York, Chris convinced his then employer to relocate him to San Francisco, as his true desire was to join a startup.

“Back in school, I don’t think I knew that starting an internet company was a thing. That might seem crazy, but I didn’t really know that it was a possibility.

“If I could go back in time, would I do it a whole bunch differently? Maybe. If I was born today I would’ve known about startups in middle school or elementary school,” says Chris.

Chris talks through his early career

“Worrying seems crazy to me”

He has just founded Grove, a company he’s bootstrapping. For him, the threat of failure isn’t a consideration, and he’s ready to get right back into startup life.

“I’m operating like failure isn’t an option, but I’m also a very pragmatic realistic person. I know that failure is unfortunately the likely outcome for all these companies, mine included, but I’m not operating like it is,” he says.

Grove is building a personalised financial planning platform that helps people understand and manage their finances better. Chris says that existing online tools don’t look at someone’s full financial picture and often ignore components that should be considered, including company stock, savings goals and real estate.

Although there are advisers that take this holistic approach, they are typically aimed at “ultra-high net worth people, who may already work with someone like Goldman Sachs”, says Chris.

No time for worries

His goal is to build a platform that can be used by people with assets between $50,000 and $5 million. He’s confident that through technology Grove can bring the “private wealth” approach to a much larger set of people.

He says that he doesn’t have time in the day to worry, and that the only thing driving him is making the right choices for his company.

While he’ll be upset if Grove doesn’t succeed, he’s not going to think about it right now. What’s the point?

“I’ll worry about something when it actually matters. Will my company succeed? I don’t know. Worrying about it now just seems crazy to me. If it does succeed, then I wasted all this time worrying about it unnecessarily.

“I’ll find out later,” he says.

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