10 of the Most Counterintuitive Pieces of Advice From Famous Entrepreneurs

We all love to take advice from people who’ve previously been through the same situations as us or who are further along a similar path to us. For entrepreneurs this is particularly useful, since it’s such a difficult, unknown path to tread sometimes.

Funnily enough, some of the advice I’ve come across through reading interviews and articles from famous entrepreneurs is often counterintuitive to what I would expect them to say. I thought it would be interesting to gather some of this advice into one place, so here are ten of the most counterintuitive pieces of advice I’ve come across from famous entrepreneur.

Paul Graham: Don’t think big

Empirically, the way to do really big things seems to be to start with deceptively small things.

Paul Graham’s advice is something I was really surprised about at first, but it actually makes a lot of sense. No great outcome is achieved without lots of smaller steps to get there, and it’s almost certain that these smaller steps can lead to change your direction somewhat.

Empirically, it’s not just for other people that you need to start small. You need to for your own sake.

Graham points out how big companies like Facebook and Apple have come a long way from relatively small and humble beginnings. It’s hard to argue with logic like that.

I think the way to use these big ideas is not to try to identify a precise point in the future and then ask yourself how to get from here to there, like the popular image of a visionary. You’ll be better off if you operate like Columbus and just head in a general westerly direction. Don’t try to construct the future like a building, because your current blueprint is almost certainly mistaken. Start with something you know works, and when you expand, expand westward.

The popular image of the visionary is someone with a clear view of the future, but empirically it may be better to have a blurry one.

Leo Babauta: Don’t set goals

“These days, however, I live without goals, for the most part. It’s absolutely liberating, and contrary to what you might have been taught, it absolutely doesn’t mean you stop achieving things.

It means you stop letting yourself be limited by goals.”

Goal-setting is a pretty difficult practice to argue with, particularly for those of us who focus on life-hacking and productivity a lot, as goal-setting is pretty much ingrained for us.

Leo’s advice is to stop setting goals so we can live without the frustration and regret of chasing goals and never achieving them.

If you live without goals, you’ll explore new territory. You’ll learn some unexpected things. You’ll end up in surprising places. That’s the beauty of this philosophy, but it’s also a difficult transition.

It might sound like this is an easy way to get nothing done, but Leo says he still feels productive, even without goals:

What do you do, then? Lay around on the couch all day, sleeping and watching TV and eating Ho-Hos? No, you simply do. You find something you’re passionate about, and do it. Just because you don’t have goals doesn’t mean you do nothing — you can create, you can produce, you can follow your passion.

Dave Goldberg: Leave the office at 5:30

We’ve all heard of young founders and CEOs putting in long days and pulling all-nighters to get more work done. In some ways, this has become a pervasive view of Silicon Valley and how startups are run.

Dave Goldberg, CEO of SurveyMonkey, shows that it’s possible to get out of the office by 5:30 and still build a billion-dollar business.

Goldberg leaves work at 5:30 PM every day to spend time with his family. While he does get back online after he puts his children to bed after 8:00 PM, he sets an example that makes it easier for the company to build and maintain its workforce. A CEO who spends time with his family every day demonstrates to other employees who have families that it’s okay to be home for dinner and live a life outside the office.

Goldberg realized how important having a company culture of work-life balance was if he wanted to hire, and keep, top-tier employees:

Early in his tenure, he put culture into action by recruiting the current SVP of Product and Engineering, Selina Tobaccowala, when she was four months pregnant. Making SurveyMonkey a place where team members can actually have a family life made it possible for Goldberg to close the highly sought after recruit, even given the competitive hiring market.

Elon Musk: Seek out negative feedback

Elon Musk has had his fair share of negative press in the past, but surprisingly he says this can be really useful:

Always seek negative feedback, even though it can be mentally painful.

His advice is to pay attention to negative, constructive feedback, even if you’d rather ignore it.

They won’t always be right, but I find the single biggest error people make is to ignore constructive, negative feedback.

In fact, Musk even advocates asking for negative feedback from others:

Don’t tell me what you like, tell me what you don’t like.

Dharmesh Shah agrees with Musk, saying you should actively seek out negative feedback to test your idea and your willingness to follow it through:

Seek out the most critical opinions of your plan that you can find. The natural tendency for a first-time entrepreneur is to fall in love with an idea and then look for friends and colleagues to support it. After all, who wants to have a fledgling idea crushed by naysayers? But these are exactly the types of folks you should be looking for.

Have them shred your plan and designs from top to bottom. If you find yourself agreeing with them and having doubts, then your plan (and possibly you) may not have the mettle to make it. But if you are able to defend it with conviction, repeatedly, then you probably have both the moxie to last through the long, tough grind you’re facing, as well as a plan that just might work.

Jeff Bezos: Change your mind a lot

When Jeff Bezos visited the 37 Signals office, he shared this counterintuitive advicewith Jason Fried:

He said people who were right a lot of the time were people who often changed their minds. He doesn’t think consistency of thought is a particularly positive trait. It’s perfectly healthy — encouraged, even — to have an idea tomorrow that contradicted your idea today.

This is a really surprising one for me, but I was definitely glad to hear it! It can sometimes feel like sticking to your original plan is the most important sign of dedication and perseverance, but Bezos points out how important being open to changing your mind can be.

He’s observed that the smartest people are constantly revising their understanding, reconsidering a problem they thought they’d already solved. They’re open to new points of view, new information, new ideas, contradictions, and challenges to their own way of thinking.

This doesn’t mean you shouldn’t have a well formed point of view, but it means you should consider your point of view as temporary.

Tim Ferriss: Don’t go all in with your business

If you’ve ever felt like starting your business as a side project must mean you’re not fully committed and it’s going to fail, you’ll love this piece of advice. I felt relieved to read Tim Ferriss’s advice to maintain a full-time income while building a business:

Work backwards from a target monthly income goal, design your business to support that, then minimize the amount of moving pieces and automate it. All that can be done with a full-time job, and I discourage people from cutting all ties and losing full-time income to focus on a business. You don’t have to make that leap. People tend to think it’s employee or entrepreneur, but there’s a broad spectrum and you can very slowly and methodically move from one end to the other.

Daniel Blumenthal from TripAdvisor agrees with Tim, and says that although learning on someone else’s dime before going all-in with your company isn’t the popular approach, it’s probably the best one.

Work in a great company that will teach you how to scale. Work at a startup to see how the game is played. Build your connections. Pay off some student loans. For God’s sake, finish school. Then go for it, and don’t give yourself an excuse for why it was ok for you to fail.

Nate Kontny: Stay in the building

You’ve probably heard about how important it is for entrepreneurs to ‘get out of the building’ when starting a new company. The point of this is to talk to real customers and work out how to solve their problems so you can build something people want.

Nate Kontny has a very different idea about how to ensure you’re building a great product:

If you want to create something that truly makes a dent in the universe, you need to have a thorough understanding of a problem. When you’re building stuff only for other people, that’s tough to accomplish. Innovations like the Swiffer take Proctor and Gamble deep and lengthy periods of research where they hire teams of ethnographers to study their customers. You think you really understand someone’s business after 30 minutes over coffee? I didn’t.

Nate says that looking at your own habits and problems is a better place to start:

But you know who you can research with much greater depth 24 hours a day? Yourself. And you have plenty of problems.

Want a good place for inspiration? Look at your credit card statement. Each one of those line items, represents some job or problem that’s important enough you coughed up money for it. That’s a great list of tasks you have in life. Analyze them and the steps involved. Which one can you make simpler?

Reid Hoffman: Be embarrassed with your first version

LinkedIn founder Reid Hoffman argues against perfectionism and having a big launch with a finished product:

It’s the emphasis [on] time. It’s getting out and getting in the market and learning and moving, [which are] much more important than the ego satisfaction of ‘Oh, I want to do it completely behind a cloak and then [remove] the cloak and everyone knows how wonderful and what a genius I am cause they think the product is so wonderful.’ That’s actually rarely the winning strategy. The actual winning strategy is ‘I’m moving, I’m getting out there and I’m adapting at a fast rate.’

Hoffman says we should focus on shortening the time to getting feedback from users so we can start iterating immediately based on real user feedback:

…the key things to shorten the [length of time for] getting to the market with a minimum viable product… I had learned from SocialNet and PayPal. As opposed to waiting for a perfect product, you actually want to be launching the minimum viable product, the thinnest possible product, and then you iterate and develop

Chris Guillebeau: Provide the strongest guarantee you can

World traveller (literally—he’s visited every country in the world) Chris Guillebeau doesn’t advise playing it safe when it comes to guarantees for your customers:

Provide the strongest possible guarantee, and stop worrying. I don’t mess around with guarantees. My Frequent Flyer guide guarantees that customers will receive at least one free plane ticket (25,000 miles) in exchange for $49, or I don’t get to keep their money. Everything else is guaranteed for life, or for as long as the bank that processes my Visa transactions will allow me.

This might sound nuts for a small, new business when you’re still unsure of how long you’ll survive or how big you’ll grow, but Chris is convinced that giving your customers a strong guarantee is worth it.

Some people ask: with such a generous guarantee, what’s the refund rate? Answer: less than 1%.

But don’t people take advantage of you? Answer: most people are honest, so why worry about the dishonest ones? Life is too short.

Richard Branson: Go with your gut

Even at this high-point of his career, Richard Branson is still convinced that gut-feeling is his best indicator of an idea worth pursuing:

I never get the accountants in before I start up a business. It’s done on gut feeling…

It’s an unconventional approach to advocate mixing emotions with business, but I love that Branson does so:

Engage your emotions at work. Your instincts and emotions are there to help you. They are there to make things easier. For me, business is a ‘gut feeling’, and if it ever ceased to be so, I think I would give it up tomorrow.

Branson’s convinced that fun is important in business, and that creating things he cares about is a far better use of his time that working on a business that his accountants say will be viable.

Like all startup advice, counterintuitive or not, a lot of these tips might be wrong for you or your company. Or, they might be exactly what you needed to hear. Sometimes it’s so easy to get caught up in what we ‘should’ be doing that we forget there are others who have gone against the grain and had it work out for them.