Amy Hoy

Guest post: How to think like an entrepreneur, wherever you are

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This is a guest post by Amy Hoy (@amyhoy), the designer & co-founder behind Freckle Time Tracking, a former interaction design consultant to Fortune 100 companies, and a passionate crusader for creating no-nonsense products. In 2008, Amy moved from her home state of Maryland to Vienna, Austria. This article is a result of her entrepreneurial culture shock.

The mindset of the entrepreneur doesn’t come with a genetic code or a zip code, it comes with deliberate practice. You don’t have to come from an entrepreneurial family, or even come from an entrepeneurial culture.

You can cultivate your entrepreneurial mindset from anywhere… and you don’t have to do it alone.

Think like a Chess Grand Master

Did you know that there’s a measurable cognitive difference between Chess Grand Masters and novice players? Surprisingly, the difference isn’t in processing power, it’s in memory. Show a Grand Master a board in play, and she can memorize every piece in a couple seconds. Try the same trick with a novice, and you’ll be lucky if he manages a third.

Show a jumbled board — with no logic behind it — and suddenly the Grand Master and novice are equals.

Welcome to the chunking theory. A “chunk” is the cognitive science term for elements that can be bunched and remembered as a single piece of information. A Grand Chess Master can’t memorize any more random bits than a normal person, but she can reduce non-random chess piece positions to understandable moves (or chunks) — and memorize just as many chunks as a normal person can remember random pieces.

Then, working from there, the Grand Master is better able to decide what to do next. All because she spent hours and hours pouring over old chess games in her youth, one chunk at a time. Her fast memory and pattern-matching abilities work together.

She’s not stuck playing old patterns. A Grand Master uses her immense library of patterns to invent new strategies.

This is a recipe for startup success. Not sure what to do next? Need advice on pivoting to a different use case, for reaching your audience on a shoestring, for soothing ruffled cofounder feathers?

Well, if you just read and digest a thick stack of case studies, & biographies, you can put chunking and pattern-matching to work for you.

How to Create Your Own Chess Master’s Brain

Read. A lot. Don’t cherrypick things that seem to apply to you — read it all.

Read startup stories; read B2B stories; read books on strategic marketing, read books about pricing for the enterprise. Read productivity books for entrepreneurs and creativity books for artists.

Take notes. Draw comparisons from story to story, and to what you’ve personally experienced. What would you have done? How could you apply that to your business?

Learn from others’ experience, see the patterns, draw conclusions, chunk, chunk, chunk.

Then reap the rewards.

Your Contagion Network

But, you’re thinking, even if I train my brain — I can’t do everything alone. If only I lived in Silicon Valley or London, I’d have an instant network.

I won’t lie: who you know is important. But not the way you think.

What you should really worry about now is social contagion.

You’re Infected with Your Friends & Family

Did you know that, statistically speaking, your smoking, investing, eating, and exercise habits — even your overall happiness! — can be accurately predicted by looking at the habits of the people close to you?

Sure, it could be peer pressure — it could be a selection effect. It could also be simply that we tend to subconsciously look, think, and act like those we care about.  Normal, in other words.

What to do, then, if entrepreneurship is abnormal where you are? If you live outside a tech hub, were born to a risk-averse family (or society)? If you’re surrounded by normal people enjoying normal jobs?

You can override this negative social contagion by reversing it: Surround yourself with people you aspire to be like, virtually and physically. Create on purpose what you lacked by accident.

Expose Yourself to the Good Germs Long Distance

No need to pick up and move. Get intense from afar, with role models you might not ever meet in person:

  • read their books, blogs, tweets
  • analyze what they do (not just what they say)
  • hang up inspiring quotes or lists
  • hang up a photo of a particular role model you admire. What Would Seth Godin Do? What Would Jason Cohen Do?
  • take a few moments every day to think about their traits you admire

Cheesy? Hell yes. But who cares, so long as it works? And it definitely works. Research shows that simply writing a short essay about a friend’s act of self-control can increase your own self-control.

That’s cheese you can take to the bank.

Create Your Own Mastermind

Man cannot survive on netstalking alone. Once you’ve got a strong vision of what you aspire to, plant your feet on the ground by creating your very own mastermind.

A mastermind is a tight-knit group of people who get you, who’ve got your back… and who’ll kick your backside if you let yourself down. In other words, exactly the type of thing you need to keep going in a tough entrepreneurial climate.

First, aim for a local mastermind. You only need three people to start. Try all the usual suspects — HN, Reddit, Craigslist, tech meetups and hangouts, even small business associations. Your ideal members may be keeping a low profile.

If you can’t find find three locals, no worries. That’s what the internet is for.

This will be your group — it’s okay (even essential) to be choosy. Are you aiming for a juicy acquisition target? A paying SaaS? iPhone or mobile? Get specific.

Then it’s up to you to set the agendas, the regular meeting times, and the culture of productive prodding. That’s what makes a mastermind so incredibly powerful.

The Bottom Line: Be Proud

Being an entrepreneur is all about being different — even if you were born in a Silicon Valley garage. Being yourself in a risk-averse family, city, or country just makes you slightly more different than most.

To succeed, work hard — and embrace being different.

You didn’t choose to be an entrepreneur because it was the easy route.

  • Damon Oldcorn

    Very upbeat and from a different slant, should inspire a few.

  • David Hickson

    great post, reminded me a little of the book Connected (, which is all about not only the topology of network (the more embedded you are w/in it the more effective it becomes (btw can be a bad thing if network of pathogen!)) but also the quality of contagion (the info that flows from node to node).

    like the chess metaphor.

  • Roland

    It’s just about not giving up. If your startup fails, your team sucks, whatever: Draw the conclusion and don’t give up in general. Adjust your product, start over with another idea. Whatever it makes sense.

    And it is essential to find people doing the same or even better: Have gone through it already successfully.

    • Amy Hoy

      Oh yes, persistence is critical. But you also have to know when to give up – or when to admit minor defeat, change tracks, so you don’t fail entirely.

      And if you constantly make bad choices, but never give up, where will that put you?

  • Schmoo

    It’s of no use to the analogy, but intersting nontheless: There’s more to the ‘magic’ of a grandmaster than just the chunking – the face-recognition part of the brain is actually subverted to recognise board layouts, which is why to be amongst the best at chess you need to start early.

    • Amy Hoy

      Schmoo, so true! The brain is awesome. But is there evidence that shows that only happens in kids? There’s so much evidence of people (adults) being able to partially remap various brain functions after strokes, hemispherectomies, and so on… but I’d be intrigued to hear if there’s specific evidence for the repurposing of the facial recognition systems for chess only happening in a given window in childhood!

      • Yaz

        I don’t think there is a specific window during childhood. It’s just that a child’s developing brain is more easily able to adapt to new thinking, and the adaptiveness slowly degrades as we age. True, chunking is not the only aspect in the making of a grand master, but is a major capability.

        The idea that you should learn as much as you can, recognize patterns, and then create new strategies makes a ton of sense.

  • Balakumar Muthu

    Wow… that’s quite inspirational!

  • neomale


  • js4all

    Great, inspiring post. Thanks.

  • Anita Posch

    Amy, as I said: you’re a great writer!
    cheers, anita

  • Maintenance Man

    Wow. I realize that I do cherrypick readings that seem relevant to me. Who would have throught that I could benefit by reading it all once in a while? Nice insight.

    • Non-Maintenance man

      Maintenance man… now that you will have little time to do anything except catching up RSS feeds.. all the best at your job! :P

      • Amy Hoy

        Luckily, Maintenance Man understands that I meant “read things from all sorts of sources” not “read everything on the internet” ;)

  • Andreas Klinger

    put this to the main – now! :)

  • David S. Rose

    Very interesting! Your post calls to mind Bob Rice’s superb book ‘Three Moves Ahead: What Chess Can Teach You About Business (even if you’ve never played)’

    To my mind it is perhaps the single best entrepreneurial business book of the decade, using lots of tech startup examples from the author’s experience as an early stage angel investor.

    Thanks for an interesting perspective!

    • Alberto

      Thank you very much for that book tip David.
      Excellent post Amy!

    • Amy Hoy

      Thanks, David! I’m definitely going to buy that book. :)

  • Bob

    Wow, this article is pretty bad.

    First of all it’s “grandmaster” not “grand master”. If you’re going to use a word 10 times in your first paragraph you might want to check how it’s spelled.

    Secondly, “Show a Grand Master a board in play, and she can memorize every piece in a couple seconds.” simply isn’t true. That’s not how chunking works.

    Thirdly, well.. it doesn’t really matter. It’s already clear you fundamentally don’t understand what you’re trying to write about.

    • Amy Hoy

      Hi Bob, valid point with the grand master vs grandmaster. However, I’ve seen the experiment carried out with the moving board/memorizing pieces. It was performed with Susan Polgar for a documentary called My Brilliant Brian. They put a 2D representation of a board in play on a moving truck and drove it past her. She saw it for at most 3-4 seconds (moving) and then was able to completely recreate the board layout almost immediately.

      Is it chunking alone that makes that possible? Probably not, as Schmoo pointed out, grandmasters seem to also use the facial recognition capacities and apply them to boards.

      But, nevertheless!

      • Amy Hoy

        My Brilliant Brain, that is. My Brilliant Brian would be a completely different series.

    • Steve O'Hear

      Bob, lighten up over the grand master vs grandmaster. And I thought the metaphor was useful even if it was a simplified version of chess.

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  • Flag Poles

    Great comparison really. Inspiring, to say the least – thanks.

  • Kosso

    Great post +1

    I’ll encourage others to read this too

    We only get one shot.

    Everybody dies. Not everybody lives.

    Go for it. Aim high.

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  • Mike T

    Great post and nice to see I’m doing/exhibiting most of the things you suggest while living in one of those non-tech/risk-averse places. Maybe I’ve got a chance after all!

  • Art Conroy


    Right on. You got the right idea. The entrepreneur’s brain can be mapped…I have been doing this in the field and at Va Tech in a lab. Its a directed-graph model that originates from the frames we use to process sensory information. I had to coin a term to capture the essence of the model – semantic intelligence mental model. I made my millions using it in data derivatives simulation software on wall street. You can teach people to think like entrepreneurs, no question. Your concept of chucking is valid as well, although when you drill down into the neural processes it is a six phase process – frame, cluster, connect,relate, measure, compare…bingo, out pops a chunk or pattern. Also, I lived in Germany for many years and read, write, speak the language. It is a great linguistic template for making sure you do first things first…neurally speaking that is…have fun.

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  • American Flags

    This is very informative! Thanks for such a great resource!

  • bulk sms gateway

    This blog is a good one! Its original, thanks for the info! Is there a way I can tell my people about this post. If only we had more great blogs out there like this one!

  • flagpoles

    Opening your own business can be the most stressful, yet rewarding experience! Thanks for the insights.

  • Irene

    Wow. This is really amazing! I like the logic behind this. Gotta go. Need to train my mind. =)

  • Billy Kirsch

    Great post thanks. Yes, building a team or ‘mastermind’ is vital to thrive and survive the feeling of isolation entrepreneurs sometimes feel. A team, tribe, cirlce, mastermind whatever you call it, it’s important.

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