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Great Founders Write

Principles for Clear Thinking, Confident Writing, and Startup Success

Ben Putano

Writing is the ultimate accelerator for clear thinking, communication, leadership, and personal growth. It’s the tool used by world-changing founders from Benjamin Franklin to Oprah Winfrey to Jeff Bezos and countless more.
140 pages and 25 links

Holloway Editione1.0.0

Updated August 14, 2024

Introduction: Why Great Founders Write

Clear thinking becomes clear writing; one can’t exist without the other.William Zissner*

Benjamin Franklin believed true wealth came from hard work and steady progress.

He wasn’t just referring to money, but wealth in all forms: happiness, health, personal development, and relationships. He warned his neighbors against risky bets and get-rich-quick-schemes. In the last decade of his life, Franklin wrote this in his autobiography:

“Human felicity is produced not so much by great pieces of good fortune that seldom happen, as by little advantages that occur every day.”

Franklin put his own advice into practice, day-in and day-out, for eighty-four years. His scope of accomplishments is nothing short of incredible: Franklin was the continent’s greatest scientist, inventor, diplomat, business strategist, humorist, and political thinker. He invented bifocal glasses, discovered lightning was electricity, and built the country’s first media conglomerate. In politics, he helped unite the embattled colonies and proposed the federal model of government we know today.

“But the most interesting thing that Franklin invented, and continually reinvented,” said biographer Walter Isaacson, “was himself.”

How did the youngest son of a tradesman become a profitable poet by age twelve, the owner of a print shop by twenty-two, a decorated inventor and scientist in middle age, and a Founding Father in his seventies? No person, not even Franklin, is born with such a broad range of talents. He wasn’t a genius in any particular field of study. Instead, Franklin’s brilliance was his ability to continually transform himself.

That catalyst for Franklin’s transformation through the years? Writing.

“Writing has been of great use to me in the course of my life, and was a principal means of my advancement,” he wrote in his autobiography.

Franklin used writing as a tool for personal growth. As a boy, he devised an exercise for himself: he would read a volume of famous essays, set them aside for a few days, and then try to rewrite them from memory. He not only learned how to write like his favorite essayists, but how to think like them.

He also wrote as a means to grow his influence. Throughout his life, Franklin published letters and essays to the public on topics ranging from business and money to politics, civics, health, and war. Some of his letters were written under pseudonyms like Silence Dogood, an old widow, which helped him build empathy for people of all backgrounds. His straightforward and often humorous style won him countless friends and attracted only a few enemies, but even they came around to Franklin eventually.

Franklin wrote to grow his business. When he lacked the funds to start his own newspaper in Philadelphia, he instead wrote for the leading paper in town, The American Weekly Mercury. Franklin’s goal was to bolster sales of the Mercury while tanking the only other paper in the city, The Pennsylvania Gazette, thus thinning out the competition. His plan worked. Franklin’s essays, which he wrote under the pseudonym Busy-Body, forced a steep decline in sales for the Gazette, which Franklin then bought at a discount. He went on to build the most successful media conglomerate of the new world.

Most notably, Franklin used his writing to usher in a new nation. After decades of playing peacekeeper between Britain and the colonies, Franklin became an ardent supporter of American Independence. He wrote the Articles of Confederation—the predecessor to the US Constitution—and played an active role in the Revolution. He even wrote methods and procedures to help General George Washington train the Continental Army. But his greatest contribution to the cause was as an editor. Franklin suggested small but significant changes to Thomas Jefferson’s Declaration of Independence. Here’s biographer Walter Isaacson again:

“[Franklin] crossed out, using the heavy backslashes that he often employed, the last three words of Jefferson’s phrase ‘We hold these truths to be sacred and undeniable’ and changed them to the words now enshrined in history: ‘We hold these truths to be self-evident.’”

Benjamin Franklin was a great founder in every conceivable way. He founded businesses, clubs, non-profit organizations, schools, political parties, and eventually, a nation. As entrepreneurs, we have so much to learn from his example.

His most enduring lesson? Great founders write.

The Master Skill

Entrepreneurs are driven. It’s in our nature. We’re willing to risk our time, money, and reputations to bring our crazy ideas to life. We want to succeed more than anything else in the world—more than sleep, more than comfort, and sometimes even more than our health (though I don’t recommend it).

And why are we striving? For independence. Freedom. Wealth. Notoriety. To change the world. To provide a better life for our families for generations to come.

Whether your goal is to build a lifestyle business or the next global giant, you’re defined by your drive to succeed. To turn nothing into something. To create the world you want to live in.

But all too often, the success you crave stays just out of reach. It’s so close you can almost taste it. There seems to be an invisible wall keeping you from your destiny. You’d give anything to reach the other side. What’s stopping you?

It’s not an invisible wall in your way—it’s a mirror.

The thing most often holding us back from entrepreneurial success is ourself. We struggle to share our mission, build support, and empathize with the people we are trying to serve: our customers, shareholders, and teams.

Most importantly, we fail to understand the inner workings of our mind. We stunt our growth with negative thoughts and subconscious habits. We undermine our progress in ways we aren’t even aware of.

Yes, there are external barriers to success as well, and some people face more adversity than others. But even external battles are decided by individual actions: your ability to communicate, to rally support, to coordinate global teams, and to paint the vision of a better future for everyone.

These challenges seem numerous and disconnected at first glance. But they all have the same surprisingly simple (though not easy) solution:

Writing.

Writing is the master skill for life and business. It’s the most versatile and enduring tool ever invented. And today it’s more important than ever—especially for founders.

The Language of Business

Writing and entrepreneurship have been linked since the beginning of time—literally.

Historians believe writing was developed for record keeping in ancient Sumer (modern day Iraq). In fact, one of the oldest known pieces of writing, called the Tablet of Kushim, is a business receipt:

“29,086 measures barley 37 months Kushim.”

Kushim, the person who signed his name at the end, was not a royal figure or prophet. He was an accountant.

Business has evolved dramatically since the times of Kushim, but the importance of writing has not. If anything, writing has become only more important to the modern entrepreneur.

Thanks to software and the internet, nearly all the traditional barriers to startup entry have been torn down. You no longer need to procure expensive hardware, office space, or even a full-time team. You can build your entire company with on-demand tools and freelance contractors. You can even build a technology company without writing a single line of code.

Anyone can start a company today, and more people are doing just that. Competition is fiercer than ever. You are now competing in a global market, and technology is upending every industry. In the twentieth century, three- to five-year plans were the norm. Today, even twelve-month plans risk becoming obsolete.

The way we work has also changed dramatically. We spend less time in the same room with coworkers. Remote work was already growing in popularity, but the COVID-19 pandemic pushed this fringe trend to the mainstream.

YCombinator, often considered the world’s top startup accelerator, has had a front-row seat to this dramatic shift. Data from their startup-focused jobs platform illustrates the change:

“In 2019, just 15 percent of small companies and 10 percent of large companies on the platform were building remote organizations. In 2021, that shifted dramatically to 86 percent of small companies and 85 percent of large companies.”

What do these massive shifts in entrepreneurship mean for founders? There are three big takeaways:

  1. Writing is now your primary mode of communication, especially if you lead a remote or hybrid team. Even if your team works in-person, there’s a good chance your customers, suppliers, or business partners are dispersed around the globe.

  2. Most companies can no longer compete on logistics, distribution, or even technology. Instead, messaging is your most reliable competitive edge: what you do, for whom, and why they should care.

  3. You must be more adaptable than ever. You need the flexibility to change your strategy, build new skills, and lead in new ways. Most importantly, you need to build a deeper understanding of yourself. Writing and journaling are the primary tools for this self-development.

This shift to globalized markets and decentralized work is just the beginning. The future is becoming less predictable. What worked five years ago will not work today, and what works today may not work tomorrow.

Are you ready?

What Great Founders Have in Common

Many of the world’s most influential entrepreneurs are also prolific writers.

Media mogul Oprah Winfrey has kept a journal since she was fifteen years old. “It’s a wonder that I’ve managed to be a successful human being considering how pathetic I appeared in many of my daily musings,” she said in a blog post on her website. “It’s a testament to growth and grace that I’ve come this far.”

Jeff Bezos, the founder of Amazon, has built his entire organization on the back of meticulous writing habits. From shareholder letters to product meetings, writing plays an essential role in running the global behemoth (we’ll revisit Amazon’s writing tactics many times throughout this book).

Tim Ferriss—an entrepreneur, author, and podcast host—credits writing with transforming his life when he was a student at Princeton.

Despite being a neuroscience major, Ferriss took a non-fiction writing course taught by the legendary journalist John McPhee. It was in this class that Ferriss developed the minimalist mindset he’s famous for today. Ferriss recalls getting papers back from McPhee where there was more red ink than black. Whole passages were crossed out. “You don’t need this,” McPhee wrote in the margins.

McPhee didn’t just teach Ferris how to write; he taught him how to think. “Once I started taking this writing course, my grades in all of my other classes went up,” Ferriss said on his podcast.

And the power of writing extends far beyond business. The world’s first two-time Nobel Prize winner, Marie Curie, kept a diary throughout her career, particularly after the death of her husband, who was also her lab partner. She wrote to her late husband as a means to summon the courage to continue their historic work. “I am working in the laboratory all day long, it is all I can do: I am better off there than anywhere else,” she wrote.

(A few years later, Curie published a 971-page, Nobel-winning treatise on radioactivity. Talk about prolific.)

Writing enables the external storage of information that can be represented symbolically (e.g., letters, numbers, words, formulas, drawings) and which can then be analyzed, critiqued, reproduced, and transformed, among other potential actions …

Writing might be beneficial to cognitive skills because it requires focusing of attention, planning and forethought, organization of one’s thinking, and reflective thought, among other abilities—thereby sharpening these skills through practice and reinforcement …

Writing is a significant literacy activity in modern life that enables individuals to accomplish a variety of personal, intellectual, occupational, and recreational goals.

Writing has always been an important skill for entrepreneurs, but it has never been this important.

That’s why I wrote this book.

The Writing Book for Entrepreneurs

Great Founders Write is the book I wish existed when I started my first company. It contains all the lessons I learned the hard way—through the wins and losses of building multiple businesses.

I’ve worked at the intersection of writing and entrepreneurship for nearly a decade. I’m the founder of Damn Gravity Media, a publishing house for business, creative work, and personal growth books. We partner with founders and business leaders to share their stories with the world. Prior to that I ran WeContent, a content marketing agency for startups and tech companies. We wrote hundreds of pieces that helped our clients grow their audiences.

In preparation for this book, I spent eighteen months studying some of the world’s best entrepreneurs, including Sarah Blakely, Warren Buffett, Ryan Holiday, Jeff Bezos, and more. I also researched the best work on writing and human psychology from experts like Robert Cialdini, John McPhee, Natalie Goldberg, Stephen King, and William Zissner.

In addition, I learned from numerous entrepreneurs and writers you may have not yet heard of, but are equally impressive:

  • Amanda Natividad, a startup content marketer and trained chef;

  • Andrew Barry, the founder of a corporate learning development consultancy.

  • Andy Raskin, a strategic narrative consultant for CEOs and leadership teams

  • Arvid Kahl, a developer, entrepreneur, and multi-time author; and

  • Dickie Bush and Nicolas Cole, the founders of Ship30for30

  • Drew Eric Whitman, author of Ca$hvertising

  • Jay Acunzo, an author, keynote speaker, B2B marketing consultant, and podcast host;

  • Jamie Russo, author, founder, and former Senior Program Manager at Amazon Advertising;

  • Josh Bernoff, author of Writing Without Bullshit

  • Mac Conwell, a multi-time founder, currently building Rarebreed Ventures.

  • Meredith Metsker, a journalist-turned-B2B content marketer;

  • Shaan Puri, co-founder of The Hustle

The result, I hope, is a book that helps every entrepreneur discover (or rediscover) their love for writing.

Great Founders Write is divided into sections based on the four core principles of great writing:

  • Write with Purpose

  • Write with Empathy

  • Write with Clarity

  • Write with Courage

It’s designed to be practical and immediately applicable. We’ll dive deep into specific writing use cases, including marketing, sales, training, persuasion, communication, and more. I’ll also show you how to use writing as the ultimate personal development tool.

Finally, you’ll find free writing tool like templates, frameworks, and cheat sheets at the end of many chapters. You can access them all by going to www.greatfounderswrite.com/bonus and entering your email.

Writing is often considered an art form. This book is not about the art of writing. It’s about wielding writing as a tool for your own transformation into a better entrepreneur, leader, and person.

If you’re open to the slow, messy, but transformative process of becoming your best self, then this book is for you. Read on.

Part I: Write with Purpose

If you don’t know where you’re going, you might not get there.Yogi Berra*

Begin with the End in Mind

How Jeff Bezos Created a Culture of Long-Term Thinking

“What the hell is the point of this?”

We’ve all read blog posts, landing pages, or long-winded emails that have made us ask this question.

The writing is all over the place. Details are out of order. The writer pummels you with every half-baked thought in their cluttered mind. Worst of all, you don’t know why you should be reading it in the first place. You eventually (and rightfully) give up. You’ll never get that time back and refuse to waste any more.

This, my friends, is a failure to write with purpose.

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Writing with No Rudder

Nothing great is built alone. The best founders are able to rally support around their vision and purpose. They see the future so clearly and vividly, you’d think they’ve already been there. A powerful why is one of the strongest forces behind a successful startup.

But we often forget to identify an equally clear vision and purpose for our writing. We start writing without really knowing what we’re trying to say. And once we do find the point, we don’t edit our work to make it clear. The reader has to slog through lines of rambling just to understand why you wrote them in the first place. It’s exhausting.

Writing this way is like trying to sail a boat with no rudder. Getting to your intended destination is all but impossible, especially in choppy waters. This isn’t just an inconvenience for your reader—it costs your company precious time and actual money.

Josh Bernoff, author of the excellent book Writing Without Bullshit, calculated that poor writing costs American businesses $396 billion every year.

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Why Are You Writing This?

With any powerful tool, careful aim is vitally important. Writing is no different.

Bezos has a clear purpose for every shareholder letter: to reinforce Amazon’s long-term mission of market leadership. Most of the time, your purpose is more mundane, like rescheduling a meeting. Big or small, you need to know what you’re trying to achieve.

Start every piece of writing by asking yourself, “Why am I writing this?” It doesn’t matter if it’s an email or a book. In fact, the shorter the communication, the more important the question.

I often write, “Why am I writing this?” at the top of my doc or email before drafting. When I hit a writer’s block, it’s usually because I have forgotten the purpose of the piece, and I ask myself the question again.

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Defining a Powerful Purpose: Write Like a Developer

Sometimes you need your writing to resonate on a deeper level. You aren’t just firing off an email, but trying to convince a superstar designer to join your team. Or maybe you’re creating the landing page for a brand-new product that has the potential to triple your business.

When you need to define a deep, emotional purpose for your writing, don’t turn to visionary founders for inspiration. Talk to your software development team.

Software developers and product managers are masters of purpose-driven writing. They do it every day. You won’t find their work in Google Docs or on your blog, but in your task management system.

I’m talking about product user stories.

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Say the Most Important Thing First

How to Improve Your Daily Communication

Let’s talk about the most common form of writing in your work today: email.

It’s easy to take emails for granted. They’re so routine that we don’t even think about them as writing. They’re just busywork—something we do. But because emails are so ubiquitous, small improvements in the way we write them can make a massive difference over time.

Think about these three email subject lines. What do they have in common?

Subject: Updated health insurance policy

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The Inverted Business Pyramid

We can learn a lot about informational writing from our friends in the news media. Their job is to share information (ideally) without judgment or bias.

To do this, they use a time-tested writing framework called the inverted pyramid.

Inverted Pyramid (Journalism)

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Sell With Storytelling

How to Write Convincing Copy for Your Startup

Copywriting is sales at scale.

One great piece of writing can do the job of a thousand salespeople. Strong copywriting will improve every aspect of your business, from your website to sales emails to paid ads and job descriptions. It’s one of the most powerful skills you can learn as a founder.

But copywriting is especially hard for startups because no one knows who you are. Big companies have established customer bases who know, like, and trust them. They offer proven solutions to known problems. Startups often start at square one: convincing potential customers they have a problem worth solving. Even if the problem is well known, you have to convince customers to ditch their current solution and take a chance on you. Either way, it’s an uphill battle

As a general rule, people hate change. So how do you convince someone your product or service is worth the effort to switch? How do you build trust, sell your solution, and generate demand in just eight seconds—the average attention span of someone on the internet?

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Copywriting for Startups: ABC123s

The best copywriting combines sales and storytelling.

This is especially true for startups. You need to convince customers the world is changing around them, then present a new path to a more beautiful future. Along the way, you must build enough trust and urgency to trigger the action you want them to take.

While running WeContent, my content marketing agency for startups, I struggled to fit our clients’ narratives into traditional copywriting frameworks. So my team and I set out to create something new: a copywriting framework that positioned startups as the obvious solution to an urgent problem in their customers’ lives.

After two years of trial and error, we developed the ABC123 framework:

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Train Your Team For Success

How to Build Teaching Material to Scale Your Company the Right Way

I wish I had known Andrew Barry back in 2018. He would have saved me a lot of pain … and money.

Instead, I had to learn the hard way what happens when a fast-growing company fails to properly train their team.

WeContent was finally picking up steam. After months of cold outreach, I had just closed our best month ever—literally double the revenue from the month prior. But that also meant we had twice as many blog posts to write. I quickly got to work contracting three new writers and a freelance editor to meet the demand. The folks I found had good resumes and strong portfolios. I assigned them to my existing accounts so I could focus on our new, bigger clients.

Companies hired WeContent to teach complex tech topics through blog posts and white papers. The irony is that when I hired my new teammates, I failed to teach them the process that had made us successful. Instead of taking the time to train my team, I simply assigned article topics and deadlines for the first drafts.

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1. Building Blocks

Before you write a single step of your training program, let’s go over the fundamentals. We’ll call these Building Blocks because they set the foundation for your program. Your building blocks include resources, principles, and your employees’ levels of prior knowledge.

Resources

Your resources are the content, tools, and experts at your disposal.

There’s a good chance you’re not starting your training program from scratch. Look at your existing content to see what you can repurpose: your past training courses, customer knowledge base, case studies, templates, and frameworks.

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2. Key Learning Outcomes

With your building blocks in place, it’s time to start creating new material. But don’t just dive into the first module. Before you start writing, you need to identify your key learning outcomes.

Key learning outcomes, or KLOs, are what you want your audience to be able to do differently after completing each section.

Each section of your training program should focus on a single learning outcome. Learning outcomes can range from remembering factual information (i.e., definitions) to creating new solutions to complex problems. Your KLOs depend on your team’s level of prior knowledge. Less-experienced trainees should start with learning factual information, while veterans can jump straight into more challenging tasks.

For a great example of well-defined KLOs, check out The HubSpot Academy, a free online training portal for marketers, salespeople, and customer success professionals. For example, their course on website optimization is split into five lessons. The first video is simply titled, “The Importance of Website Performance.” The learning outcome for this video is crystal clear: after watching the video, the viewer should understand the importance of website performance for their company.

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3. Delivery Format

I was never very good or interested in science. But in the seventh grade I learned a lesson I’ll never forget:

The Scientific Classifications of Living Things:

  • Kingdom

  • Phylum

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4. Storyboarding

With your building blocks, learning outcomes, and delivery format in place, it’s now time to build the actual lesson. Barry calls this process “storyboarding.”

“We believe that the best educators are storytellers because they inspire learning with imagination, teaching us to visualize and think about things instead of simply presenting us with information,” said Barry.

Craft your lesson like you’re telling a story. Curious Lion recommends a narrative framework that looks like this:

5. Reinforcement

The last step of any good learning program is reinforcement. You’ve worked hard to teach your audience something new; don’t waste that effort by failing to follow up.

“[Reinforcement] is becoming increasingly important in a world in which remote work is the new normal for most companies,” said Barry.

As a trainer, give your audience a chance to practice what they’ve just learned. Use case studies and role playing to reinforce new behaviors. If the lesson is more hands-on, such as fielding customer support phone calls, give trainees real-life reps and review with them afterward.

Your team also needs time to talk with you or the expert. Build in Q&A time, facilitated discussions, coaching and mentoring, and case studies where the expert and learners work through problems together. For additional help and support, encourage your audiences to give feedback to each other. Help them set up a “buddy system” for peer-to-peer learning.

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Learning from My Failure, So You Don’t Have To

In the aftermath of WeContent’s blog post debacle, I took a hard look at the way I ran my business. It was clear I had set my team up for failure. Instead of training them on my editorial standards, I threw them into the ocean without a raft. The curse of knowledge bit me hard, and it almost cost me my business.

So when I hired a new freelance writer six months later, I made sure they’d be ready. I wrote a detailed creative brief for each article to serve as their training material. Coincidentally, this document included all the same steps as Curious Lion’s training development approach:

  • Building blocks—My client’s mission, brand positioning, value proposition, and product descriptions; word count requirement; and links to relevant prior research and blog posts

  • Learning outcomes—Blog post objective and target audience description

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Part II: Write with Empathy

[Empathy has] no script. There is no right way or wrong way to do it. It’s simply listening, holding space, withholding judgment, emotionally connecting, and communicating that incredibly healing message of ‘You’re not alone.’Brené Brown*

Kill Your Ego, Replace With Empathy

How to Destroy a Brand in Four Words

Ratan Tata—the president of India’s third-largest automaker, Tata Motors—was traveling home from work one day in 2003 when he noticed something that disturbed him.

It was a dark and rainy evening. While Mr. Tata was safe in his luxury vehicle, he saw a family of three dangerously riding through the muddy streets of Mumbai on a two-wheeler. In India, electric bikes and mopeds are three times more popular than automobiles, so this sight was not unusual. But it sparked an idea in Mr. Tata—an opportunity to help India’s burgeoning middle class … and mint a new fortune in the process.

What if Tata Motors created a car that was as affordable as a moped?

Mr. Tata became obsessed with the idea and made an impassioned pitch to his board. The company got to work soon after. Over five hundred engineers spent more than four years designing a vehicle that wasn’t just comfortable and safe, but extremely affordable. When the Tata Nano was unveiled in 2008, industry analysts hailed it as a miracle of business and engineering. Best of all, it cost just $3K USD. Pundits were already declaring victory for Tata.

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“The World’s Cheapest Car”

The logic behind the project was sound. There were millions of Indian families who needed an affordable car, and the Nano had everything they could ever want. But no one bought it. Ironically, the Nano was most popular among rich businessmen. They bought it as a toy—a gimmick to show off to their friends. You can imagine Mr. Tata’s frustration. He built exactly what the people of India needed—or so he thought. Was it possible he missed something?

Turns out, the Tata Nano was doomed from the moment it was announced. When Mr. Tata unveiled the Nano at the Auto Expo in 2008, it was accompanied by a horrendously out-of-touch slogan:

“The World’s Cheapest Car.”

In rapidly developing India, buying a vehicle was a status symbol for upwardly mobile families. It wasn’t just a practical purchase, but a highly emotional one. With those four words, the Nano positioned itself as a car for poor people. Any self-respecting person would rather keep their moped than drive “the world’s cheapest car.”

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Think Small

Could the Nano’s fate have been different? Luckily, we don’t have to imagine too hard. History gives us a near-perfect comparison—another small, affordable car built for the upwardly mobile masses:

The Volkswagen Beetle.

In the 1950s, Volkswagen aspired to break into the American market where big cars reigned supreme. They hired ad executive Bill Bernbach—one of the original “Mad Men” of Madison Avenue—to develop the Beetle’s first advertising campaign.

Bernbach was struck by the honesty of the Beetle. It wasn’t trying to be anything it wasn’t. It was small, well-built, affordable, and didn’t take itself too seriously. Bernbach’s first ad tried to capture this honesty and paired it with a bit of self-deprecating humor. It took America by storm:

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Could Empathy Have Saved the Tata Nano?

In 2015, after a massive decline in demand, the Nano team rebranded.

They scrapped their price-aggressive language and positioned the Nano as a fast, fun, easy car for free-loving young people (sound familiar?) Commercials featured young adults, laughing and carrying guitars, driving out of their way for their favorite street food. They drove to the beach, to parties, and cruised with friends down beautiful coastal streets. The ads focused on the experience of owning a Nano. But did it work?

The new campaign was a success from a creative standpoint, but it didn’t help the Nano’s sales. In 2018, Tata discontinued the Nano for good.

Marketing consultant Nauby Gupta thinks the new campaign was too little, too late. “[The Nano] has been positioned as a price-aggressive product,” he said in an article from Economic Times, “You can’t get away from that.”

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Know Thy Reader

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.

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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.”

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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?

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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.)

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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.

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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.

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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.

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Find The Win-Win Opportunity

How to Persuade Without Losing Your Soul

My junior year of college was an odd one.

Living in my fraternity house, I’d regularly stay up until 3:00 or 4:00 a.m. with my friends. Then I’d be up at 6:00 a.m. to head to work at Northwestern Mutual, an insurance and wealth management company. I was an intern, but not the type that made coffee runs and collected mail. I was a licensed insurance agent.

At 7:00 a.m., I’d be in the office for our agent meeting and to hit the phones. The first hour of every day was spent cold-calling strangers to talk about death and money. Like I said, it was an odd year.

But this experience taught me the art of persuasion. I was a college student (and not a very good one) trying to sell life insurance to doctors, lawyers, and families with small kids. Why would they even take a meeting, let alone buy something from me?

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Great Founders Persuade—Ethically

A founder’s job can be distilled to two tasks:

  1. To build

  2. To persuade

Founders build products, audiences, processes, and teams. For many founders (especially those without a sales background) this is where they stop. “Build it, and they will come” is still a pervasive mindset, even if the founder knows it’s not true. Deep down, they hope it’s true, because building is what they’re good at. Building is in their comfort zone.

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4 Steps to Ethical Persuasion

According to research by USC Professor Jay Conger (which first appeared in the Harvard Business Review), there are four steps to becoming more persuasive in the workplace:

  1. Establish credibility

  2. Find common ground

  3. Use vivid examples

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Practicing Persuasion

Persuasion is an art. Like all art, it’s rooted in empathy. Your goal is not to win, but to create a win-win scenario for you and others involved.

There’s one last thing to keep in mind about persuasion: it takes practice. As a life insurance agent, I would literally role-play sales conversations with my boss to hone my persuasion skills. We’d also review after meetings and phone calls to identify what I did well and where I could improve.

I recommend keeping a journal of your persuasive conversations. Record the details of the situation, what went well, and where you could improve. What objections came up? What did you learn about the other party that could help you create a better win-win solution? What facts or vivid examples could you add to strengthen your position?

When you really believe in something, persuasion will no longer feel like a necessary evil. It will feel like a natural step in the journey of building your vision.

Nurture Key Relationships

How to Write to Your Investors, Stakeholders, and Biggest Champions

Mac Conwell is a developer, two-time startup founder, and venture capitalist. In 2020 he started Rarebreed Ventures, a pre-seed fund focused on underrepresented founders—female founders, minority founders, and founders living outside the main startup hubs in the US.

For all of Mac’s skills as a developer and capital allocator, his greatest strength (in my opinion) is his storytelling. As we discussed the importance of founder-investor communications, he shared this story:

“When I worked for the state of Maryland venture fund, we had a high-flying startup who had just landed a major distribution deal. Things were going great, but then we didn’t hear from them for a while. I went about my business, working other deals and such. Then one day I got an email from one of the co-founders.”

Mac seemed visibly shaken at this moment, as if he was reliving the experience while telling me the story. For an investor, surprise emails are about as welcome as kidney stones.

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4 Habits of Great Relationship Builders

According to Mac, great founders share four communication habits that help them build strong relationships with their investors:

1. When in Doubt, over-Communicate

In the first story Mac shared with me, the founder suffered from a common problem: under-communication.

“Come to me with solutions, not problems,” is still the pervasive mindset in business, despite it being thoroughly debunked by organizational researchers. When times get tough, many founders and business leaders go quiet until they find a solution to share. They don’t want to look incompetent or panicky by raising the alarm.

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Great Relationships Start with You

Good communication builds trust, and trust builds relationships. This is true with your team as much as your investors. If you’ve chosen the right investors—those who bring more to the table than just money—then you want as close a relationship as possible to them.

“The more you communicate with your investors, the more value you’ll get out of them,” said Mac.

Yes, VCs have a financial incentive to see you succeed. But it’s you who needs to lead the relationship. Share your wins, losses, and challenges on a regular basis. Model the type of communication you want and that’s what you’ll receive in return.

Part III: Write with Clarity

Clutter is the disease of American writing. We are a society strangling in unnecessary words, circular constructions, pompous frills, and meaningless jargon.William Zissner*

Make Every Word Count

How to Turn Clarity Into a Competitive Advantage

Natalie is the CEO of an enterprise SaaS startup (real names have been changed to protect the guilty).

Every Monday morning, after making her coffee, Natalie checks her company’s Stripe dashboard to review their Net Monthly Recurring Revenue (Net MRR), the company’s North Star metric. It’s lower than she expected to see, so she shoots a direct message to her Head of Growth, Miguel.

“Hey Miguel, what’s the status on our Q3 Net MRR? We’re already a month in and don’t seem to be on track to reach the target. We need to keep up the pace or we’re going to get lapped. Let me know what I can do to help.”

Miguel is just getting ready for his week when he gets a push notification on his phone. It’s from Natalie. Miguel reads the message. Then he reads it again. What does she mean by “we’re going to get lapped?” He feels his adrenaline rising and his heart starts to race. As the head of growth, the buck stops with him. It’s his ass on the line if they don’t hit their Net MRR.

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Battling Chaos with Clarity

Being a startup founder is a stressful and lonely job. When the pressure is on, we tend to “act now and think later,” a survival instinct that keeps us safe from snakes … only to run straight into a den of lions.

In times of high pressure and uncertainty, one leadership trait is more valuable than any other: clarity.

Clear communication is the knife that cuts through chaos, giving you and your team a direction and a plan. It focuses your limited resources like a laser aimed at the single most important thing. Clarity brings sanity back to insane situations.

Meanwhile, a lack of clarity amplifies the chaos with every layer of management it passes through. Like a game of telephone, the message becomes so obscured it ceases to resemble the original intention.

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Clear Writing Starts with a Clear Purpose

There are many ways to ruin your writing, but the most common offense is not knowing what you’re trying to say in the first place.

Think back to Natalie’s message to Miguel. What was she trying to achieve? Was she trying to be helpful, or did she just want to put pressure on Miguel? From Miguel’s perspective, it seems like the latter. Message received loud and clear.

But let’s assume Natalie was trying to be helpful. In that case, her message failed. The unintended pressure on Miguel created uncertainty throughout the company.

Remember our powerful purpose template from earlier in this book? Let’s use it here to clarify Natalie’s message:

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Simplify

How to Write More Clearly and Confidently

You could spend a lifetime studying the English language.

Or you could follow these eight simple rules of clear writing and get 95% of what you need.

Bookmark this page and keep it handy. These rules will save you time and countless hours of wasted energy:

  1. KISS

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Never Skip Editing

How to Mold Your Writing Into the Perfect Message

It took me years to get comfortable reading my own writing. It’s a lot like hearing yourself talk on video. You feel exposed and a bit like a fraud.

Because of this, I would never edit my work. I would fly through the draft and hit send without a second thought. I told myself my writing sounded more natural this way. If “natural” meant sounding like an illiterate caveman, then I nailed it. In reality, I was just hurting my credibility and confidence.

My most embarrassing lapse in editing came shortly after college. I was in my first full-time job as a consultant for a non-profit. My boss knew I enjoyed writing, so he asked me to create a promotional flier for an upcoming event. I was excited about the project … so excited, I failed to edit. Over-confident and over-caffeinated, I breezed through the assignment and printed out the final version for my boss. He returned it fifteen minutes later with more red ink than I’ve ever seen. I made typos big and small. I even misspelled our organization’s name!

I was completely embarrassed, but it taught me an invaluable lesson about writing. I pinned up that red-inked flier in my cubicle as a reminder to always edit my work.

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The Four Edits

Before we get started, here’s a reminder from my editor: don’t try to write and edit at the same time.

Write first, walk away from the draft, and then return to edit. Reviewing with fresh eyes will make a big difference. Even a minute of intentional breathing is enough to reset your brain to prepare for editing.

First Edit: Substance

The first edit is all about the big picture. Forget grammar, punctuation, and word choice for now. Focus on the substance of your writing.

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Design for Easy Reading

How to Format Your Writing To Reach More People

Chris Do is an accomplished graphic designer, entrepreneur, and teacher with more than one million YouTube subscribers. One of his most popular video series is where he critiques designs sent in from fans. Some of them are pretty rough.

But no matter how bad a design is, Chris always follows the same thoughtful process:

First, he describes what he sees in the design. What’s happening on the screen or page? His goal is to get a sense of the work as a whole before critiquing the parts.

Second, he thinks about how the design makes him feel. This forces him to judge the piece emotionally before logic takes over.

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1. Give the Reader Direction

Good design gives your eyes a clear path to follow. We tend to notice bigger elements first, as well as elements in the forefront of the design. If you see eyes on a page, you’ll naturally look to where they are looking. A web designer can use these techniques to guide a visitor directly to the call-to-action.

Writing has a natural starting point: the top left. But after that is a long, meandering path that few readers are willing to take. In the world of business writing, no one reads every word. That means you need to direct your reader to the most important information.

Most readers skim writing before deciding to read it more thoroughly. Readers will jump to the biggest elements first: your headers and subheaders. These are your directional arrows. Don’t try to be clever—make your headers clear and descriptive.

Let’s take this section as an example. This chapter is titled, “Design for Easy Reading.” There’s no question what you’re going to learn here: writing lessons from the world of design.

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2. Create Focal Points

Good design also creates clear focal points. Poor design has no focus, confusing the mind about where to look first. This is exhausting to the viewer, and most will simply give up trying.

Good writing also has focal points. The most important information should be easy to identify. Readers in a hurry should be able to jump to the most important text and get the gist of what you’re saying. Poorly designed writing gives equal weight to every word. You may think every word is important, but your reader won’t. If everything on the page seems important, readers will decide that nothing is important.

When speaking, we naturally emphasize the most important points. We enunciate, talk more loudly, and even repeat ourselves. You can do the same thing when you write.

Italicize for emphasis.

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3. Create White Space

In design, what you don’t see is just as important as what you do see.

White space is literally the space in between design elements. It’s a critical piece in good design, and one that takes time to appreciate and master. Young designers often try to fit as much as possible on the page. Experienced designers know that white space is what makes their work stand out.

This principle is just as important in your writing.

Meredith Metsker, a journalist-turned-content marketer for SaaS startups, emphasizes the use of white space in her writing.

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4. Design for Clarity

Chris Do’s biggest pet peeve when critiquing design: Legibility!

Amateur designers often sacrifice readability for style. This type of design serves no one but the designer. “Legibility should supersede every other consideration,” said Chris.

For writers, this obviously means to avoid illegible fonts. But it’s also a reminder to prioritize clarity over style. And as we’ve seen, clarity is more than the words you choose—it’s about giving your reader a clear direction through good design. Never assume your words will be read, even when writing to a captive audience like your employees. Your reader’s attention is always earned.

Design your writing to be clear, interesting, and easy to read. Then watch your impact and influence soar.

Part IV: Write with Courage

It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again; … who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.Theodore Roosevelt*

Lead from The Front

How to Deliver Bad News, Take a Stand, and Do the Right Thing During Crisis

Over ten hours had passed when Robinhood CEO Vlad Tenev finally broke his silence. By then he had become the most hated man on Wall Street. Maybe in all of America.

The irony is that Tenev built Robinhood with a mission to democratize finance for all.

Earlier that day, on January 28, 2021, Tenev and his executive team made the decision to freeze the buying of Gamestop stock ($GME), along with several other stocks that were targets of a historic short squeeze.

Unlike past short squeezes, which were weapons of the financial elite, this one was orchestrated and led by regular people. Retail investors met and rallied through a Reddit forum called WallStreetBets (WSB). Soon, the entire world was in on the action, from nurses in L.A. to Elon Musk. In just a matter of months, $GME rose from $5 per share to almost $500. The frenzy pushed hedge fund shorters to the edge of bankruptcy, costing them billions of dollars in the process.

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1. Be Visible

Tenev’s first mistake was simply not showing up when people needed him. The ten hours it took for him to address Robinhood’s decision to freeze $GME trading is inexcusable. In that time, wild conspiracy theories raged all over the internet.

An internet sleuth discovered that one of Robinhood’s largest investors, D1 Capital, held a large short position against Gamestop. The fund had lost 20% of its value in a matter of weeks. Was this why Robinhood delisted Gamestop?

Later, an even more damning fact surfaced: Robinhood’s largest enterprise customer, Citadel Securities, had recently invested in a hedge fund who was on the verge of bankruptcy from the Gamestop short squeeze. Just a coincidence? Or was Robinhood forced to take action by a powerful institution?

The truth was much more boring. Robinhood faced a compliance issue that threatened to shut down the entire platform. While trading on Robinhood appears instant, transactions take up to two days to officially process. A rule called T-2 requires Robinhood to keep cash on hand to cover those trades until they’re completed. The Gamestop frenzy pushed Robinhood’s cash requirements to a hundred times their normal levels. On January 28, they had just five hours to either come up with the cash or get shut down by the government. By freezing $GME and other rallying stocks, they were able to lower their cash requirements and keep the platform afloat.

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2. Be Direct

During moments of crisis, be direct. Skip the formalities and business-speak. Give people the information they need.

Vlad Tenev should have been on the front lines communicating with customers during the Gamestop crisis. Instead, he directed his comms team to release an anemic blog post titled, “Keeping Customers Informed Through Market Volatility.”

The first problem with the article is the title. It’s as generic and bureaucratic as you can get. Using the phrase “market volatility” on the day of the largest short squeeze in history isn’t just an understatement—it’s misleading. Customers seeking answers on Robinhood’s blog overlooked the post because it didn’t directly address Gamestop.

The blog post’s problems continued in the first paragraph. Instead of addressing the $GME freeze outright, Robinhood led with their mission statement. Then they said how proud they were of themselves:

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3. Be Honest

During a crisis, any whiff of dishonesty will shatter your trust with customers.

Robinhood never outright lied during the Gamestop short squeeze, but they withheld crucial information from the public for an entire trading day— specifically, the reason why they froze $GME. This lack of transparency was dishonest in its own way.

Tenev should have immediately shared everything he knew with the public using a tried-and-true phrase from the history of crisis communication, “Here’s what we know.” There was no benefit of withholding information if they had nothing to hide.

As a leader, you won’t have all the answers during a crisis, but that’s no excuse for not sharing what you know. Customers don’t need perfect information, but they need something.

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4. Be Helpful

The “fog of war” is a military term that describes the confusion and chaos that covers a battlefield. It can be blinding and disorienting. During times of crisis, when the fog of war is thick, leaders need to help their people reach the other side in one piece.

Robinhood again failed this test in spectacular fashion. Not only did they fail to provide a helpful explanation for freezing $GME, but they sent readers on a wild goose chase to find their own answers.

Here’s a paragraph from Robinhood’s blog post on January 28:

Amid significant market volatility, it’s important as ever that we help customers stay informed. That’s why we’re committed to providing people with educational resources. We recently revamped and expanded Robinhood Learn to help people take advantage of the hundreds of financial resources we offer and educate themselves, including how to make sense of a volatile market.

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5. Be Accountable

Robinhood’s decision to freeze $GME turned a chaotic situation into a crisis. Yet the company never took responsibility for their role.

Without Robinhood’s zero-commission trading tool, the short squeeze would have never been possible. Did they ever consider something like this could happen? It’s not like they didn’t have warning signs—GME trade volume rose rapidly throughout the month of January, which meant Robinhood needed more and more cash on hand to cover deposits. In hindsight, couldn’t they have been more prepared?

Worst of all, Robinhood never took responsibility for fixing the situation. After announcing the stock freeze, they made no indication they were working to unfreeze them. Instead, they seemed to blame their customers for the freeze:

We’re determined to provide new and experienced investors with the tools and resources to help them invest responsibly for their long-term financial futures.

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6. Be Human

All of Robinhood’s missteps were exacerbated by communication that sounded like it was written by legal. (It probably was.) Here’s one of the more obtuse statements from Tenev’s Twitter thread on January 28:

As a brokerage firm, Robinhood has many financial requirements, including SEC net capital obligations and clearinghouse deposits. Some of these requirements fluctuate based on volatility in the markets and can be substantial in the current environment.

As a platform for the people, Robinhood failed to communicate like a real person. Instead they opted to hide behind corporate jargon and legal-washed messaging.

7. Provide Next Steps

Desperate Robinhood customers needed answers about their $GME stock. When would the freeze be lifted? What would happen next?

Ten hours after the freeze, Tenev offered some painfully vague next steps in his Twitter thread. He said Robinhood would open up limited sales of $GME and other stocks the next day. But what did “limited” mean, exactly? And could Robinhood freeze the stock again?

Robinhood failed to give any more direction to their customers or the public. This led anxious users to seek out new leaders—folks like Dave Portnoy, the founder of Barstool Sports, who called for the imprisonment of Tenev and his hedge fund overlords on social media. His position may have been extreme, but at least he gave his followers hope for a resolution.

At the end of his Twitter thread, Vlad Tenev offered an “apology” of sorts:

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What Courageous Communication Looks Like

We know what Robinhood did wrong, but how should they have responded instead? Luckily, we don’t need to hypothesize.

Public.com is a commission-free trading platform, just like Robinhood. On January 28, they were also forced to freeze $GME and other stocks during the squeeze. But their response to the crisis couldn’t have been more different.

From their very first message, Public.com’s response to the Gamestop freeze was the exact opposite of Robinhood’s.

In short, it was courageous.

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Build Your Audience

How to Attract the Right Followers to Grow Your Business

Building an online audience requires a different kind of courage than leading through a crisis. You’re choosing to put yourself out there, even when you’d rather be anywhere else.

And for those with the courage to build an audience, the payoff is massive.

Naval Ravikant, founder of AngelList, believes media is the most powerful form of leverage today (along with software). That’s because, unlike capital and labor, media is permissionless leverage.

Here’s an excerpt from The Almanack of Naval Ravikant by Eric Jorgenson:

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When a Bigger Audience Isn’t Better

Jay Acunzo is a father, author, keynote speaker, podcaster, and one of the best B2B storytellers in the business. Brands pay him $2,500 an hour to develop content that resonates with their audiences.

But Acunzo’s personal audience? Not as big as you might think. At around 20K Twitter followers, he’s a relatively small fish in the world of B2B marketing. This is by choice.

“I have a small but passionate, long-lasting, and very loyal audience from a lot of premium brands. So I can charge higher amounts for what I offer,” said Acunzo on an episode of the Creative Elements podcast with Jay Clouse.

Acunzo’s high-value audience allows him to charge more while earning higher profit margins and working with fewer people. He didn’t build a bigger audience, but a better one. That’s the definition of leverage.

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Five Principles for Building a High-Value Audience of Any Size

Building a high-value audience starts with creating high-value content.

This is not a lesson in going viral or hacking social media algorithms. Those tactics change constantly and are not entirely in your control anyway. Instead, I’m going to share five principles for building an engaged, passionate following of any size. These principles haven’t changed in millennia, and they aren’t likely to change anytime soon.

Let’s dive in:

1. Set the Right Goals

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Last Thing: Build Relationships With Your Audience

As a writer and entrepreneur, the thing I value most is the people I’ve met on my journey.

Building an audience can quickly become a soulless numbers game if you forget about the people on the other side. Take time to start one-on-one conversations and build actual relationships with others. If you’re on Twitter, DM someone who regularly comments on your posts. Ask them about their goals and how you can help. Jump on a call with an email subscriber who opens every one of your newsletters. Where do they live? What do they do in their free time? What obstacles stand in their way?

Building relationships is good for the soul and good for business. It’s very difficult to quit products or services when you’ve had a personal conversation with the founder. The more time you spend building relationships, the more fervent your audience will become.

Two people stand out to me as excellent relationship-builders: Mac Conwell and Arvid Kahl. You know Mac from the section Nurture Key Relationships. He regularly takes over two hundred phone calls a month with founders, limited partners, and aspiring entrepreneurs looking for advice. Mac’s spotlight has grown because of the personal relationships he’s built.

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Practice, Practice, Practice

How to Master The Craft of Writing

In architecture, a keystone is a wedge-shaped rock that sits at the pinnacle of an archway. It balances the forces of the opposing sides of the arch, holding the structure together with surprising strength. In fact, the more weight you put on top of the keystone, the stronger the arch becomes.

Entrepreneurship is a lot like building an arch. The keystone is your writing routine.

Good writing strengthens every other part of your business, from decision-making to marketing. It’s vital for keeping opposing forces and emotions in balance. Without a writing routine, your archway is more likely to topple.

My friend and fellow entrepreneur Andy Ellwood has maintained a writing routine for over fifteen years. Through journals and blogging, Andy has used writing as a tool to build a successful career at some of the fastest-growing startups in tech. It’s also helped him navigate personal challenges and reinvent himself several times over.

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13 Writing Exercises for Every Occasion

In this final chapter, I want to fill up your writing toolbox with some of my favorite exercises. There are tools for self-reflection, strategic planning, stress management, creativity, and more.

I’ve labeled each exercise with the following information:

✏️ Purpose: For example, personal growth, strategic planning, or writing craft

🕑 Time commitment: How long each session should take

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Master the Craft and the Tool

No matter what writing exercises you use, writing for yourself is one of the most powerful habits an entrepreneur can build.

Writing for yourself helps clarify your thinking, improve your judgment, flex your creative muscles, and build empathy. Writing is also a way to vent. When things are going wrong—when you’re overwhelmed by the stresses of building a company—writing is both cathartic and productive. That’s a rare combination.

Incorporate writing into your daily life with these exercises. Try them all to see which ones work best for you. Once one exercise becomes a habit, add another. And don’t forget to enjoy every minute of it.

As a founder, you write for your audiences, customers, teammates, and investors. But at the end of the day, the most important person to write for is yourself.

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Postscript: The Work Has Just Begun

You don’t start out writing good stuff. You start out writing crap and thinking it’s good stuff, and then gradually you get better at it. That’s why I say one of the most valuable traits is persistence.Octavia E. Butler*

This book has shown you the principles, frameworks, and tools to become a great founder through the power of writing. Now comes the hard part: turning your words into action.

Benjamin Franklin is considered one of the greatest writers in American history, but he was a doer first and foremost. He didn’t just write about his disagreements with the governing Penn family of Pennsylvania—he actively defied them and their corrupt policies. He built coalitions, proposed new laws, and spent decades in London lobbying the British Parliament. When King George failed to support the American cause, Franklin didn’t just write about the injustices of the crown—he took up arms against them.

When Arlan Hamilton saw the lack of venture capital funding for underrepresented founders, she didn’t just write a scathing viral blog post about it (which she did). She founded her own venture firm: Backstage Capital, the name an homage to her days as a touring band manager. Backstage Capital has since invested in over two hundred companies led by underrepresented founders.

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Acknowledgments

Wow, where to begin.

I’ve wanted to write a book for as long as I can remember, so I should start by thanking my mom, dad, and stepmom for encouraging my early interest in writing. You bought me my first books, drove me to and from writing competitions, and supported me through years of school. When I decided to become an entrepreneur and author, you encouraged me every step of the way. I love you all. Thank you for this life you gave me.

I also want to thank my sister Julianne, a fellow entrepreneur and my writing muse. You inspire me with your energy, wisdom, and strength. Thank you to my older sister, Kristi, who was the first writer and author I knew, and my brother, CJ, whose passion for life brings me joy every day. And a big thank you to Uncle Jeff, who sparked my curiosity for learning at a young age. Love y’all.

This book was far from a solo effort. I would have never finished it without my productivity coach, Victoria Lopez. You helped me stay motivated and on track for eighteen whole months. Can’t thank you enough.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.

About the Author

Ben Putano is a writer, entrepreneur, and book publisher. He’s the founder of Damn Gravity Media, a publishing house that inspires and educates tomorrow’s great founders. Ben lives in Chicago with his wife, Mary, and is an avid ultimate frisbee player.

This is a preview. Buy it now for lifetime access to expert knowledge, including future updates.
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