Using metaphors to enhance your storytelling

This metaphor is so powerful for three reasons:

The best metaphors can leverage emotions to communicate your message.

At the time of this quote, many people were scared of computers. Similar to the way a majority of people currently fear the impact of AI on society.

By comparing computers to bicycles Jobs was able to leverage the emotions associated with bikes. Bikes are used by kids, they are safe, fun and functional. They can help you get to and from places or can just be used for entertainment. They are in no way something to be feared, instead, they enhance your life.

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On top of the emotions, the comparison was realistic. At the time that bicycles were first released there was also significant fear around them. No joke, some doctors at the time thought that you would get a “bike face” from travelling at superhuman speeds. To this day there are lots of discussions around the potential infertility issues caused by bikes. Comparing computers to something that was once feared but now loved helped computers undergo the same transition.

Similar to the way that asking questions during a pitch can plant an idea in the listener’s mind, a great metaphor lets the connect the dots themselves making the concept feel more powerful as they did it themselves.

Overall if you can create a metaphor that leverages emotions, is realistic and plants an idea in the listener’s mind then you will be armed with one of the best storytelling tools a founder can have.

Someone just spent $236,000,000 on a painting. Here’s why it matters for your wallet.

The WSJ just reported the highest price ever paid for modern art at auction.

While equities, gold, bitcoin hover near highs, the art market is showing signs of early recovery after one of the longest downturns since the 1990s.

Here’s where it gets interesting→

Each investing environment is unique, but after the dot com crash, contemporary and post-war art grew ~24% a year for a decade, and after 2008, it grew ~11% annually for 12 years.*

Overall, the segment has outpaced the S&P by 15 percent with near-zero correlation from 1995 to 2025.

Now, Masterworks lets you invest in shares of artworks featuring legends like Banksy, Basquiat, and Picasso. Since 2019, investors have deployed $1.25 billion across 500+ artworks.

Masterworks has sold 25 works with net annualized returns like 14.6%, 17.6%, and 17.8%.

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_{*Per Masterworks data. Investing involves risk. Past performance not indicative of future returns. Important Reg A disclosures: masterworks.com/cd}