How to Build Empathy in Six Questions

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Holloway Editione1.0.0

Updated August 14, 2024
Great Founders Write
Common questions covered here
How did Airbnb's founders figure out what their customers actually needed?
What questions should I ask to really understand my customers before I write to them?
How do I write marketing copy that feels personal instead of generic?
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You’re reading an excerpt of Great Founders Write, by Ben Putano, writer, entrepreneur, and book publisher. He’s the founder of Damn Gravity Media, a publishing house that inspires and educates tomorrow’s great founders. Purchase now for lifetime access to the book and on-demand video course.

When Brian Chesky and Joe Gebbia, the founders of Airbnb, arrived at the YCombinator headquarters in San Francisco, they received a shocking piece of advice that would change their lives.

The co-founder of YC, Paul Graham, asked the founders a seemingly innocent question: β€œWhere do your customers live?” There weren’t many at the time, but they said Airbnb had a cluster of early adopters in New York City.

β€œThen what the hell are you doing here?” Graham asked. β€œGet on a plane and go talk to your customers.”

How could they refuse? For months, Chesky and Gebbia made the grueling weekly commute between San Francisco and New York. They talked with every early customer on the platform while living in Airbnbs themselves. This experience gave them invaluable insights, such as the importance of good photography for every listing. Airbnb began to flourish in New York, and later, across the country.

Could Chesky and Gebbia have learned the same lessons by calling or surveying their customers? No chance. By visiting the homes of their early hosts, the Airbnb founders did so much more than just β€œtalk” to their customers. They saw their lives on and off the platform. They walked a mile in their shoesβ€”or in this case, literally slept a night on their couch. Airbnb didn’t invent the concept of couch surfing, but they made it mainstream by nailing the tiny details, such as providing up to one million dollars of damage protection for each listing. Hosts didn’t ask for this, but through hours of conversation, Chesky and Gebbia realized they needed it for their peace of mind.

That’s the power of empathy.

β€œGet to know your customers” is such common startup advice that we can easily forget what it really means. It’s not about compiling demographics and creating fictional buyer personas. It’s about having intimate conversations to understand what your customers really want, need, and what stands in their way from getting it. To serve your customers, you need to know what they truly care about and what they don’t and prioritize ruthlessly.

The same is true when writing. Knowing your reader’s occupation and LinkedIn credentials isn’t enough. To build massive empathy, you need to sleep a night on their couch (or whatever your equivalent is).

Ultimately, there are six questions you need to answer to really Know Thy Reader:

  1. Who am I writing to?

  2. What do they want?

  3. What do they need?

  4. What stands in their way?

  5. How can I help?

  6. Why should they care?

These questions, of course, also apply to knowing thy customer. Because for founders, your readers and customers are often one in the same.

Let’s dig into each question.

1. Who Am I Writing To?

Julianne, my sister, recently broke free from the corporate world and started her own wellness studio. She teaches yoga, Thai massage, and Reiki energy therapy. As a new founder, Julianne is experiencing firsthand the challenge of not just delivering services, but attracting the right customers, leasing studio space, and managing finances.

But Julianne’s goal is not to build a wellness empire. Instead, she wants the freedom to do work she loves and to help people. She’s actively downsizing her lifestyle to fit this dream. She pictures a day when she lives in a tiny house and tends to her garden while teaching classes full of enthusiastic students on her own schedule. This is not the typical entrepreneurial dream, but it’s hers.

Why am I telling you this? Because Julianne is one of the people I wrote this book for. I had her name listed at the top of my first draft like I was writing a letter to her.

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