Know Thy Reader

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.

How to Build Empathy in Six Questions

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: “Where 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.

“Then what the hell are you doing here?” Graham asked. “Get 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 “talk” to their customers. They saw their lives on and off the platform. They walked a mile in their shoes—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.

“Get 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.

David Perrell, a writing coach and author, says, “Write for one obsessive person … Writing comes alive at the extremes.”

In other words, if you try to write to everyone, you’ll speak to no one.

The best writing happens when you write to a specific person or two. Not the perfect version of them, but the real them—their fears, flaws, dreams, and all. That person stands in proxy of every other potential reader. By focusing on your one reader, your writing will feel personal. Your readers will get the sense you actually know them, and they’ll start to think they know you, too.

Tim Ferriss used this strategy while writing The 4-Hour Workweek. After struggling to find his voice in the first draft, Ferriss decided to write to two close friends who wanted to escape the nine-to-five grind. To enhance the illusion, Ferriss literally wrote his next chapter in an email addressed to his friends. The trick worked. The 4-Hour Workweek became a number one New York Times bestseller.

The more specific you are about who you’re writing to, the stronger your writing will be. That’s why I recommend writing to someone you actually know. It could be a friend, colleague, or a customer willing to spend time with you.

Let’s look at an example:

Imagine, like Julianne, you’re building a wellness studio. You decide to add career coaching to your list of services. Your first task is to create a landing page to test your messaging and find a few early customers to try out the service.

Now ask yourself: Who am I writing to?

You want to work with creative entrepreneurs. But this is a large and diverse group. If you try to write to everyone, you’ll end up with a shapeless gray blob of a landing page. Your service will resonate with no one. If you focus on one obsessive person, your landing page will explode with life, clarity, and passion.

You choose to write to your friend Sandy, a veteran sales rep who wants to start a pottery business. She’s already started an online Esty store but dreams of opening a small studio in the heart of Ohio City, Cleveland. She’s nervous to leave the comforts of her full-time job and worries about money. She needs a plan—and a little courage—to make the leap.

Forget writing for all creative entrepreneurs. You’re writing for Sandy.

When you decide who you’re writing to, put their name at the top of your draft. Or, like Ferriss, draft an email to them. Do whatever you need to convince yourself you’re writing to one person.

Once you’re crystal-clear on your reader, let’s get to know them a little better.

2. What Do They Want?

We all have goals and desires.

Some of us want financial independence. Others want to travel. Some people dream of a simpler life, while others want adventure. Many people want to go back to the way things used to be—back to when they were happier, healthier, and had fewer worries in the world.

When your reader tells you what they want, listen to them. But keep in mind, this is not the most important thing you’ll learn about them, and it shouldn’t be the only thing, either. But knowing what your reader wants is a great starting point. You can use this information to pique their interest.

Think about Sandy, your friend who wants to open a pottery studio. What are her goals? Does she want to build a pottery empire or a small lifestyle business? What does success mean to her?

Humans are never satisfied for long. Virtually everyone wants more of something. It’s your job to identify the thing they want and help them get it.

But there’s a big difference between what your reader wants and what they need.

3. What Do They Need?

Most people are very good at telling you what they want: money, free time, adventure, independence.

But most of us are less adept at knowing what we need. Our needs, both physical and psychological, sit just below the surface of our consciousness. We don’t know we need something until we get it, or it’s suddenly taken away.

Let’s talk about your friend, Sandy. She wants to leave her corporate job and open a pottery studio. But what does she need to make this happen?

Amazingly, there are only eight things humans really need. Copywriter and author Drew Eric Whitman compiled a list of these needs in his book, Ca$hvertising (cringey name, great book on copywriting.)

He calls them The Lifeforce 8:

1. Survival

2. Sustenance (i.e., food and water)

3. Freedom from pain and fear

4. Sexual companionship

5. Comfortable living (i.e., peace of mind)

6. Achievement and winning

7. Caring for loved ones

8. Social acceptance

Then there are secondary motivations, which are less powerful but very common in our developed world. Whitman calls them “learned” motivations. There are nine in total:

1. To be informed

2. Curiosity

3. Cleanliness of body and surroundings

4. Efficiency

5. Convenience

6. Dependability/quality

7. Expression of beauty and style

8. Economy/profit

9. Bargains

These lists help explain why Tata Nano failed so spectacularly. Mr. Tata appealed to the weakest possible motivator—bargains—while ignoring primary needs like achievement and social acceptance. The Volkswagen Beetle, on the other hand, appealed to comfortable living, social acceptance, convenience, dependability, and self-expression. Affordability was hardly mentioned—it wasn’t necessary.

Now, back to Sandy. What does she need? Start at the top of the Lifeforce 8 list and work your way down. Right away you’ll see fundamental needs to address: survival and sustenance. For humans, a lack of money signals danger. Sandy needs to know she will not go hungry or lose her home if she starts her own business.

But that’s not all. She’s used to a certain level of comfort from her nine-to-five job. That’s at risk of going away when she quits. She’s not even sure she’ll succeed. It would be easier to not try at all. And what will her friends and family think if she starts a pottery studio? Will they accept her decision or call her crazy and irresponsible?

As you already know, becoming an entrepreneur is a loaded decision. It’s wrapped up in multiple fundamental needs that Sandy must satisfy before taking the leap. Your landing page should address each one of these needs specifically and explain how you help clients overcome them.

Your reader won’t tell you what they need, so it will take some digging to uncover. But once you do, you’re well on your way to building massive empathy.

Next, you need to identify and address what’s standing in their way.

4. What Stands in Their Way?

You now have a clear idea of who your reader is, what they want, and what they need. Now let’s find out what’s standing in their way: the obstacles, blind spots, villains, and forces of nature that may stop them from reaching their goals.

By recognizing the obstacles standing in your reader’s way, you’re saying to them, “You don’t have to fight this alone. We’re on the same team. It’s us versus the world, and we’re going to win.”

That’s the definition of empathy: to understand and share the feelings of another—especially in the face of uncertainty.

Most obstacles fall into one of two categories: villains and mountains. Villains are forces trying to hurt your reader. They can be internal or external, but the pain is usually immediate and acute. Mountains are challenges for your reader to overcome. They are opportunities for your reader to grow and become the best version of themselves—to achieve something great.

What stands in Sandy’s way from opening her pottery studio? Her villains are self-doubt and a well-meaning family member trying to hold her back. She’s also worried about competing with a more established pottery studio in town. Sandy’s mountains include growing her savings from six months to eighteen months, finding a studio space, and learning how to market her new business.

The best way to address your reader’s obstacles is to turn them into advantages, just like Bill Burnbach did with the Volkswagen Beetle. You can help Sandy harness her self-doubt and use it as motivation to learn more quickly. Show her how to turn that “competing” pottery studio into a collaborator.

Make a list of all the potential villains and mountains standing in your reader’s way. Next, you’ll help them turn those obstacles into opportunities.

5. How Can I Help?

The first four questions you just answered were research. Now it’s time to turn those insights into action.

Your reader is facing down villains and mountains on the way to achieving their wildest dreams. What can you do to help? Remember the lesson from Tata Motors: you are not a savior. Instead, think of yourself as a guide. You provide maps to scale mountains and swords to slay villains.

The Airbnb founders had dozens of mountains and villains to address (twice as many as a typical business, since they were building a two-sided marketplace). They had to help guests overcome the mountain of uncertainty when choosing an Airbnb. They provided professional photography as a map for each listing. Airbnb’s hosts had to face villainous guests stealing or destroying their homes. Chesky and Gebbia gave them a weapon to defend themselves in the form of damage protection.

Sandy’s villains include her own self-doubt and her mother, who guilts her into staying at her current job. As a career coach, how can you arm Sandy to take on these villains? Your weapons probably include positive self-talk exercises, scripts for having difficult conversations, and a journal for tracking her progress. Sandy’s mountains require a different form of assistance. You can help her create a map—a timeline or plan—to build new skills and reach her goal.

Go back to your list of mountains and villains from the previous step. Brainstorm different maps and swords you can provide to help your reader succeed.

6. Why Should They Care?

Whether you’re writing a landing page or an investor memo, your reader will always ask themselves the same question: “Why should I care about this? Why should I spend my precious time on you?”

This question should look familiar—we asked the same one earlier in Sell With Storytelling. I’ve added it again because it’s so important. You’ve done the hard work of building massive empathy for your reader. Now it’s time to distill your insights into a single sentence.

For this question, let’s use a tried-and-true exercise to get to the heart of the matter: The 5 Whys.

Imagine you’re talking to Sandy. You write her an email about your new career coaching service for creative entrepreneurs.

Sandy responds: “Why should I care about that?” (1x)

Using your audience research—what you know about Sandy’s wants, needs, obstacles, and potential solutions—try to craft a single sentence answer to her question.

You: “My coaching service will help you make the leap from corporate life to full-time entrepreneur.”

Sandy: “Why should I care about that?” (2x)

Keep digging to find a deeper answer to the question. The goal is to go 5 Whys deep.

You: “To live the passionate, creative life you’ve always wanted.”

Sandy: “Why should I care about that?” (3x)

You: “So you can live a life of no regrets.”

Sandy: “Why should I care about that?” (4x)

You: “Because life is short. Live it to the absolute fullest.”

Sandy: “Why should I care about that?” (5x)

You: “So that you live a life that inspires others to live their best lives.”

There it is. Is it the perfect answer to Sandy’s question? You won’t know for sure until you get feedback from actual customers. But it’s a whole lot better than just “Become a full-time entrepreneur.”

Building empathy for your reader is hard work. That’s why it’s so worthwhile—few other founders are doing it. You can stand out from the crowd just by knowing your customers better than your competitors.

As Paul Graham said, “What the hell are you doing here? Go talk to your customers.”

And crash on their couch, if they’ll let you. It will be time well spent.

Free Tool #4 BONUS: Empathy Builder Template

Empathy for your customers and readers is crucial. Go to www.greatfounderswrite.com/bonus, enter your email, then click on “Empathy Builder” to get the free template. Use this framework to write copy for your landing pages, sales emails, paid ads, or content marketing.