10 of the Most Counterintuitive Pieces of Advice From Famous Entrepreneurs

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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.

advice from famous entrepreneurs - paul grahamPaul 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.

advice from famous entrepreneurs - leo babautaLeo 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.

advice from famous entrepreneurs - dave goldbergDave 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.

advice from famous entrepreneurs - elon muskElon 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.

advice from famous entrepreneurs - jeff bezosJeff Bezos: Change your mind a lot

When Jeff Bezos visited the 37 Signals office, he shared this counterintuitive advice with 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.

advice from famous entrepreneurs - tim ferrissTim 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.

advice from famous entrepreneurs - nate kontnyNate 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?

advice from famous entrepreneurs - reid hoffmanReid 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

advice from famous entrepreneurs - chris guillebeauChris 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.

advice from famous entrepreneurs - richard bransonRichard 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.

Image credits: Time, GrowHack, Wired, Quarterly.co, Nate Kontny, , The Power of Less, Forbes 1 and 2, Lightworkers, TechCrunch

  • http://gabejohansson.com/ Gabe Johansson

    Love this! It definitely does go against the expected advice, especially Leo’s tip. Thanks for the share!

    • Belle

      Glad you liked it! Thanks for reading :)

  • http://anotherguy.us/ Tim Stiffler-Dean

    I love that you guys keep writing these articles. I’m starting up my own company right now (and using Buffer, too!) and all of the tips and pieces of advice from your various experiences and meetings with other successful people have been very valuable to me.

    The one thing I would say about not going all in – it’s best to keep your full time job while building your company in the background only if the full time job isn’t keeping you from being financially stable. If you’re a one-man team and your company will get you enough money to keep yourself more stable than if you kept your full-time job, then quitting that job is definitely an alright choice. What do you have to lose, after all?

    • Belle

      Thanks for the comment, Tim! You make a good point—if there’s only you to think about, you can probably get to a point where you don’t need to split your time much faster than if there were 2 or 3 people in your team.

    • ALI BEN SSERUGO

      Iam also stating mine in uganda.

  • http://www.seftonmedia.com/ Steven Sefton

    What a great blog! This post has taught me a few things. I especially like Chris Guillebeau’s point on making the strongest possible guarantee. If you deliver your work on time, with integrity and with results then no-one will be asking for a refund anyway.

    • Belle

      Thanks Steven! Great point, too. I think customers care mostly that you’re doing your best to back yourself and provide a top quality experience.

  • Lydia Anthony

    “Don’t set goals”…Every summer, starting in my student days, I used to create an ambitious list of goals to try to motivate myself to stay productive during all that free summer time. Ooh, but it felt like work, and usually I’d get to the end of the summer and realize with a sigh that I hadn’t accomplished a single one. I started making the goals fewer, and more and more basic, but it didn’t help. This summer I tried a radically new approach. On my whiteboard, where “Summer Goals” used to be, I wrote “What I Did This Summer” The only rule on what went on there was that it had to be something that A) was finished, and B) I was proud of. I’ve already got a smattering of things on there that feel like real accomplishments, and I’m constantly looking at the list thinking “ooh, what can I wrap up and add there?” It’s also encouraged me to write and remember events in my life that are more meaningful than “goals” to be achieved. I look forward to the end of the summer when I can look back and be truly proud!

    • http://www.seftonmedia.com/ Steven Sefton

      Such a cool idea Lydia. You like to see accomplishments rather than ticking away goals. I can see how this would work well. You should write a post on this and share it with us.

    • Belle

      Wow Lydia, this is an awesome story! I love this idea, especially the two stipulations you’ve chosen. I might even try this out myself! Thanks for sharing.

    • Heinrich

      Lydia, Thanks so much for sharing this. Not only do I fully symphesize with your approach, but I will share your story with all my students who are obsessed with goal setting procedures. Not everything works for everybody. Some love and need clear goal setting and so be it. But for all others, your story gives relief. Not only that you don’t need to, but even that there is lots of merit in not doing so.

    • http://straightalkingstudent.com Aman

      I like this idea. For day to day tracking of what I’ve actually done I’m using iDoneThis which is pretty minimalistic but provides concrete evidence of accomplishments instead of general goals.

      • Belle

        We love using iDoneThis at Buffer! It’s a great way of keeping track of what you’ve done :)

    • Summer Guest

      But, wait! If people look at your whiteboard, they can say: “I Know What You Did Last Summer”

    • http://www.swipesapp.com/ Yana from Swipes

      Really nice and encouraging approach :)

    • Harry

      very true, lydia. i’ve had the same experience with goal setting such that i may not bother myself anymore. i think its better to note your accomplishments and then see how you can build on it to get to where you want!

    • Tim

      I didn’t set goals for two summers and if you watched my life as a movie for those two summers it would look like Dazed and Confused II & III.

      I think it is important to set goals. If you aren’t achieve them it probably means you just don’t care that much about it.

    • Sandeep Rastogi

      great, easy way to go

  • gr8loans

    Another awesome piece, Joel! Thanks fro sharing!

  • http://kuratur.com/ Kuratur

    The hits just keep coming on the Buffer Blog :-)

    I find particular inspiration in Guillebeau’s comment that, “most people are honest.”

    And I love Branson and Kontny encouraging people to rely on their own instincts.

    It was interesting to see Belle mentioning more than once that these comments made her feel relieved, because that’s definitely how they make me feel.

    • Belle

      Thanks for reading, glad you enjoyed it! It’s definitely a great feeling to know you don’t have to do things a particular way, and going against the grain can really work out :)

  • Fiona

    And…be a man, apparently.

  • charlotte

    If i see another one of these lists without a single woman on it I will scream

  • Julie Harris

    Great post! One question: Where are our female entrepreneurs?

  • Heinrich

    This is awesome! My most successful lecture is called “From start-up to f… – up” and is build on cases of failure. Including my own failed entrepreneurial venture. Your collection here, Belle, takes it a level higher. Not just learning from failures (or successes, of course), but actually starting to use your own brain and make authentic decisions. Stop looking for recipes, be bold to go against “wisdom”, be bold to be a true entrepreneur. Thank you for sharing this!

  • Erika Dickstein

    I love this list but couldn’t you find a single female face to put up there? I have plenty of ideas on inspirational women entrepreneurs.

    • Belle

      Great point Erika! I’ll definitely try to add some female entrepreneurs next time. If you know of some good examples, I’d love to hear them. Thanks!

    • http://AAPastor.com/ Daniel K. Eng

      Agreed! I was thinking the same thing, Erika!

    • Fl!p

      I had exactly the same reaction. Thanks for articulating it!

    • Vocabulary Library

      I don’t care if it is male, female, or transgender.. the message and its relevance matter most.

      • Erika Dickstein

        Sigh, you just keep thinking that.

        • Red

          I sure hope he will. The messenger is of no relevance. It’s the message that counts. Who cares if it is a woman or a man?

          Hypocrite.

    • http://www.aleydasolis.com/ Aleyda Solis

      Totally agree! Thanks for commenting about this Erika, is about time that we create awareness about this. What is even sadder though is that the post is written by a woman!

    • Alyson Weiss

      This was my first reaction too! Thanks so much for voicing it. The list is great, the advice is great, but it’s completely unrepresentative.

  • Ger Kelly

    Solid article – better than the usual entrepreneurial advice peddled around the web.

    I’m building an app where people can get a taste of life running a tech startup – if you’re interested please check out http://www.hipsterCEO.com

  • e

    Great, but you could not find even ONE woman?!?!?

  • Dan Polaske

    My favorite is change your mind often. The world is constantly changing around us, and we are constantly gaining new knowledge, its crazy to think our opinions and views would not change as well.

    • ALI BEN SSERUGO

      Dan i aggree with you.

  • http://widism.com/ Clayton Elliott

    I agree with all the above. Although the opposite of some of the advice could still end up in success, there is def strong evidence to support that the above approaches to business do lead to wide variety of success stories.

    Enjoyed this post thoroughly :)

  • http://www.my-foothold.com/ Cindi

    I would love to hear the perspectives of women innovators, maybe a follow up?

    • Katie Rosebraugh

      I was thinking the same thing Cindi!

    • Trish

      From a Female Entrepreneur…….Got tired of the “Real World”. My only GOAL is to follow my passion of keeping people safe and training (background is construction safety, Quality, OSHA authorized trainer and First Aid/CPR training ). Folks in my networking group and clients keep sending me work to do safety training, site safety, audits, Policy prep and gap analysis, First Aid/CPR training… No money has been spent on marketing, no office politics and I can fire clients. Best part is that I get to INSPIRE clients and meet my “goal”.

      Out of the blue came an incredible contract for 2 months work equal to what my “job” would have paid in a year. And they’re talking about this rolling into more projects with them over several years.
      Of course, I let God worry about life’s challenges and just take care of the opportunities He brings my way. Different take than those above I guess.

  • ALI BEN SSERUGO

    It is very bad that most my fellow ugandan have not viewed those points but iam going to share it.

  • http://www.my-foothold.com/ Cindi

    I don’t think I’m the only one who feels this way: http://www.my-foothold.com/bad-bufferapp-com/

  • vadimoss

    Leave at 5:30 is not too controversial especially when you log in from home. It’s just a sign of being well organized which by itself leads to a better outcome in general.

  • http://EnlacesyMarketing.com/ Fernando Rivas

    WOWWWW!!! Spectacular post!!!!!!!!!!

  • http://www.katebrodock.com Kate Brodock

    Love these, thanks Belle! Definitely passing this along. (Though next time, include some women in here).

  • Memea

    Wow – not one female among the entrepreneurs. Great advice but I would have liked to see some variety as opposed to 10 white men.

  • Tim Geoghegan

    If this advice is counterintuitive to people, that’s probably the biggest problem facing those particular people.

  • tom_m

    Man, I do all of these things…Except not working long hours =) Still easier said than done! Good article.

  • Grace

    Striving is what makes us happy. If you are not working towards something then you are simply existing. I can definitely understand how goals can make you stressed but not having goals is like a ship without a destination. You end up drifting aimlessly through life which can leave you feeling unfulfilled. I’ve learned to be less stringent with my goal setting. Instead of adhering to a strict set of goal setting rules, I set my goals as intentions and let them go. But deep down I always know which way my compass is pointing. And every step I take in that direction fills me with happiness.