I believe creativity and coming up with ideas is a critical skill to have. So, I am always interested in books that has specific techniques for coming up with new ideas. It’s why I loved ThinkerToys by Michael Michalko, A Whack in the Side of the Head by Roger von Oech, and now Why Not by Barry Nalebuff.

Barry Nalebuff is a professor at Yale where for thirty years he has taught negotiation, innovation, strategy, and game theory. He is the co-author of six books on a variety of the above topics. Why Not is a book that offers a framework for problem solving and ingenuity. What’s interesting to me is not Barry’s stories (he co-founded Honest Tea), but the techniques for creative ideas.

The Croesus Strategy (rhymes with Jesus)

Croesus was a Greek ruler who had a significant amount of wealth. The Croesus Strategy is therefore simply: when faced with a problem, how can you solve it with money? Or to give you a better technique, if Bill Gates encountered the same problem, what would he do? (Or in some cases, why wouldn’t he have that problem?).

In the book, Barry offers the problem of telemarketers calling you in the middle of the night. While you could disconnect or turn off your phone, you may potentially important or emergency calls from family and friends. And even if you block one telemarketer’s number, another telemarketer with a different number could call. So he applies the Croesus Strategy. Bill Gates never encounters this problem. Why? Because he likely has an assistant filtering his calls, and only going to Bill when the call is important.

The idea is not to hire an assistant, but rather how you can get 99% of the benefit at 1% of the cost. How could you get all the benefits of having an assistant without spending a full-time salary on an assistant?

One way is to use a call answering machine. The call answering machine filters out unwanted calls, and means that you can call back on your own terms. However, what a call answering machine doesn’t do well is let you know when a call is an emergency you need to answer.

Thinking about filtering, any time you sign up for a new web service, you fill out a captcha (enter the letters and numbers you see, or choose all the traffic lights in this picture). One way you can filter out unwanted calls is by providing a special code to friends and family. If they call you and have the code, they can get through.

The Croesus Strategy on Medium writing

The value of any technique isn’t about knowing the technique, but about applying it to problems you have. One of those challenges is Medium writing. Applying the Croesus Strategy to Medium writing, what would it look like for Bill Gates to write articles? And rather than try to Google this, instead, imagine let’s go through the technique.

First, I imagine that like any writer, Bill Gates needs three key things: coming up with ideas, writing, and editing. To keep things simple, I’ll leave out things such as figuring out what platform to publish on, marketing/sharing the article, and such.


  • I imagine Bill Gates would hire dedicated researchers to help him come up with ideas. With Bill, I know he does a significant amount of reading so I imagine ideas aren’t hard to come by, but if he takes notes in the margins of his books, he might have someone writing those into a database or on index cards so he can see all the ideas to form connections or write articles combining these ideas together. A 1% cost, 99% benefit solution might be to capture ideas yourself onto index cards or a database so you can see the different (and similar) ideas in a single location.
  • Another way to get ideas is to have an assistant comb through great articles, noting down which ones align with Bill’s interests or preferences and then distilling those articles, again into a database or index cards. You can use a service such as Pocket or Instapaper to help you do this, or even Readwise to give you the notes from your Kindle highlights.


  • Maybe Bill writes his articles, but I’d like to think that with him earning so much money, it would be easier to dictate or hire a writer to write for him. If you are someone that thinks by talking, you can use a service such as Google’s speech-to-text software to help you transcribe your thoughts onto paper. Record on your smartphone, and go for a walk, and you get to combine two killer activities into one.
  • Rather than hire a full-time assistant to write your articles for you, you could hire one-off services from Fiverr. Anywhere from less than $10 to $200, you can get an article written or written and edited for you.
  • James Altucher takes best-selling fiction books, hires a virtual writer to replace words with synonyms to avoid copyright, and then publishes the book. Although I don’t recommend this method, you could take viral posts, replace them with your own content, copying other’s methods and structures that they have learned, with no cost.


  • Bill would at least hire someone to fix any grammar or spelling mistakes, come up with great ideas for his title, and then structure his article so that it logically flows. There are some free services that can fix grammar and spelling, such as Grammarly or Pro Writing Aid. I like to use headline analyzers (AMI’s headline analyzer is my analyzer of choice) for article titles, and although it doesn’t help you come up with great titles, it can at least tell you whether a title you come up with is worth considering. Article structure takes experience, but the low-cost way to do this is to copy another article you like or to search the many free resources on how to structure articles.
  • Another low-cost way is to use a free text-to-speech service to read your writing aloud. For some reason, when someone is reading my writing, certain mistakes are obvious to me.

The idea is not to be exhaustive, but to show you that by thinking about the expensive ideas, we can move forward with different ideas to get us 99% of the benefit at 1% of the cost.

Share the Pain

Another technique Barry describes in Why Not? is sharing the pain. Sharing the pain occurs when there is a problem and there is a certain ‘pain’ associated with it. For example, companies that pollute have to pay fines that are used to reverse the damage of the pollution created. Previously, companies would pollute and not have to worry about what happens to the environment. Governments however, saw what the pollution was doing and introduced fines to help reverse the damage, thus sharing the pain of pollution with the companies that caused it.

Share the Pain on Medium writing

There are several ‘pains’ associated with Medium writing:

Coming up with ideas / research. Any writer knows that research can be tedious, whether it’s listening to podcasts, reading books or articles, or trying to live life and then document that in a valuable way for readers. Since all writers have this same problem, why not create a database that can be populated by writers and researchers and accessible by many writers? You could charge a monthly subscription fee to access the database, and you could also see what others may have written using the articles or research, and which resources they used.

Writing the article. Again, since many writers may have this same problem, you can look to an automated solution. One way is to use AI to write an article. You can use AI to generate the article, and since the key to any article is in the editing process, you would just need to edit the article to your liking.

Editing the article. Here’s an idea, first write several articles you know will need to be edited. Then find a friend or fellow writer and offer to trade editing duties with them. They have several articles lined up that need to be edited, and you have several articles that need editing. While you are editing their articles, they are editing yours. The benefit of this is you get a different perspective and you can trade feedback, benefiting both of your writing.


The two techniques are: the Croesus Strategy (what would Bill Gates do?) and Sharing the Pain. The techniques are designed to get you coming up with different ideas. These ideas are likely ones you wouldn’t come up with on your own. And while they may not be applicable to all problems, they give you a good nudge whenever you are stuck coming up with new ideas.