An Inside Look at Drift's Content Marketing Strategy

Over the last month I’ve spent countless hours studying the content strategy that helped Drift build one of the most successful B2B brands in the technology industry. I’ve looked at more than 30 articles and documents from the company, interviewed people on their team like their VP of Marketing, David Gerhardt, and spoken with outside experts to learn what makes the company’s marketing so unique and effective.

In this article I’ll cover the following:

  • How Drift created the category of conversational marketing

  • How Drift measures, documents, and manages its content and team

  • How Drift hired their first content marketers

  • How Drift comes up with content ideas

Drift’s VP of Marketing Dave Gerhardt

Drift’s VP of Marketing Dave Gerhardt

Before we dive into content, picture these two scenes:

#1 In 2013 there were around 100 marketing technology companies. Just five years later in 2018, there were over 5000. Everybody's hopping on the boat, trying to tell their story and everyone sounds the same. It’s impossible to break through the noise.

#2 A few years ago, David Cancel was bored. He was a serial entrepreneur who had built and sold several companies. He was working at Hubspot, a large company that had bought his last startup. He was, as he says it, exercising twice a day, not really feeling like he was learning anything new or pushing hard. So he decided to spin off and do something new. Thus Drift was born.

But Cancel didn't want to create a conventional company. He saw where B2B tech was going: more and more players doing similar things, combining sophisticated levels of data and machinery to drive more leads, more volume, all the time. Yet he predicted all this marketing and sales automation was going to reach its peak, and people would again yearn for more human connections with companies. This was his plan to break through the noise.

One morning, Cancel called his Head of Marketing, David Gerhardt, who had followed Cancel from HubSpot to join Drift. Cancel told Gerhardt, “I think we should get rid of all of our forms.

Gerhardt's eyes nearly bugged out of his head. This was every marketer's nightmare. A campaign without leads. A landing page without a CTA. How the heck was he going to hit his numbers?

Screen Shot 2019-01-30 at 10.38.36 AM.png

But at Drift, they have a “disagree and commit” philosophy (more on that later). So Gerhardt went ahead and 'ungated' their content - no more need to fill out a form to get that PDF. And their entire strategy changed.

Instead of forms, they started initiating conversations, right on the page. Of course, they used their own “conversational marketing” software to do it. Immediately conversions skyrocketed.

Over the next few months Drift wrote articles, social media posts, and spoke about this strategy publicly at conferences. In doing so they took a page out of Salesforce's “No Software” playbook and turned a small strategy into something much larger, a category the company could own. The "No Forms" movement had begun.

At this point Drift gave up on the typical lead generation efforts like PPC and Display Ads that their peers spent the bulk of their time and money on and doubled down on content. Strategy as Michael Porter says is about making choices and saying no; Drift’s team had the discipline to do both.


  1. Don’t be afraid to be bold and break the rules.

  2. Promote the hell out of your success if it works.

  3. Create a category that you can own.

Next, I'll go through what makes Drift's content itself unique and effective, including how they break traditional marketing rules, how they continue to come up with new ways to hit their core brand messages, and how that is driving unprecedented success.

Breaking the Rules on Content

Focus on humans not data

Gerhardt told me that today “content is a commodity.” Before joining Drift as the company’s VP of Marketing, he was a Marketing Manager at Hubspot. While he was there he saw the internet become saturated with B2B companies producing content. Most of them mindlessly followed the industry “best-practices” (read: rules) and produced uncompelling content that lacked story or a unique voice.

Gerhardt saw an opportunity to do things differently. He believed that authentic stories and a unique brand could help Drift stand out. He didn’t want to build a faceless brand that hid behind esoteric press releases and generic blog posts. Instead he set out to build a brand that strangers on the internet could relate to.

How Drift succeeded in building this is described in their brand book and marketing manifesto, which has remained remarkably consistent up to today. Here are some of the key takeaways from those documents:

  • Only real humans: Drift doesn't do stock photography. They put their real employees and customers everywhere in their marketing. Their site and content is overflowing with customers’ faces, typically with some Drift additions. They'll often do some colored outlines or almost comic-book like illustration around their customers or employees. The most important thing to note here is that they are different. In brand building that is key.

  • Be good enough: they don't need high production quality to put something out. Sure, they'll spin up a great, polished marketing video from time to time, but the bulk of their marketing is fast, simple, and on iPhone videos. Gerhardt is particularly known for constant, hand-held videos, speaking directly to the screen, including directly on LinkedIn and Instagram stories.

  • ELI5 (Explain It To Me Like I'm Five): Drift uses simple, plain language throughout. They've practiced and honed their tone to be like an everyday conversation. It makes sense, particularly when your product is about facilitating conversations.

Some of this seems so simple, that it gave me pause. Does it really work? How do you know if it is working? So I asked Gerhardt how he measures success.

Measure in love.

Before speaking to Gerhardt I imagined him sitting behind the world’s most sophisticated marketing dashboard like a mad-scientist, pulling levers and calling shots. But when I asked him how he measures success his answer blew me away. He said, “We just know. We don’t have to search for it.”

Gerhardt says that their executive team inherently understands the power of good marketing. The podcasts, the videos, the amazing content—they all add value. Cancel and Gerhardt have talked to the best CMOs in the world and in all their conversations haven’t heard of a company that measures the true quality and love of a brand.

In a world of endless data, Drift’s content strategy is led by more intuition than hard numbers, simply asking, “Is this helpful?” or “Would we want to consume this content?” It may sound unscientific, but this first principles approach is working.

Of course, that’s not to say they don’t measure their progress at all. Gerhardt shared an internal snap of one of their Slack channels, aptly titled "drift-love".

They measure overall traffic and word of mouth over time, but it doesn't really guide their behaviour. Of course, their marketing keeps in mind overall revenue, churn, NPS, and standard metrics… but what they really track and what drives their decision-making is customer love. And Drift keeps growing.

It almost reminds of that song from RENT: “In five hundred twenty five thousand six hundred minutes. How do you measure a year in a life? How about love? Measure in love!”

Document, don't create

Drift also follows Gary Vaynerchuk’s “document, don't create" strategy of content marketing. They focus on documenting what they do and then share it quickly.

Here's one example in which they describe how to get more out of your product launches, based on how they do it. They followed up again this year with how to ship more effectively, an interview with their VP of Product. Drift has a literal Shipyard landing page, which profiles what they have recently launched, a series of new features. Drift is always sharing knowledge, and it builds up the profiles of their executives and their team, at the same time as drawing people into their brand and product.

Again, no press releases or faceless marketing. They’re more social media influencer than they are corporate marketer. More Casey Neistat than Don Draper.

Another good example is how they profile their #1 Drift Power User, who happens to be on their sales team, Eve. It is a great feature of one of their employees, with authentic interactions with their customers and users, that also details how she uses their product to grow their business.

A third solid example of how they do this is through their weekly podcast, Seeking Wisdom, which is co-hosted by Gerhardt and Cancel, and explores a number of different topics. One of their recent episodes talks very openly about how their team functions internally, for example through their use of Slack. They are always openly talking about what they are doing and how they do it.

Don't be original (everywhere)

So Drift's content is human driven, not data driven. And it's often documenting what they do, rather than creating net new content. But it's also often not original—at least the second, or third, fourth, or fifth time that you see it. And you will see it again: similar messages, over and over again, across different platforms.

Gerhardt talked to me about their philosophy on this. He said: “We make small bets, for example Cancel will write a LinkedIn post on how the future of X will be Y. If it blows up, we turn it into another medium.”  They'll take a conversation onto the podcast, for example. And then they'll turn that into more blog posts. It seems like Drift has had a least a thousand different conversations and variations of the ungating story, but each time it's a bit different.

Buffer, another content marketing giant, learned the same thing when they built their content marketing team. Rather than create original content, they focused on creating content they knew their audience needed and then made it better than anyone else. As a result they ranked for keywords with a high volume of traffic. Here are the figures their VP of Marketing gave me recently on the following landing pages:

Social media graphic sizes — 26,000 views per month

Free SEO tools resource page — 22,000 views per month

A guide on how to get verified on Twitter — 15,000 views per month

Were they the first to write a post on how to get verified on Twitter? No. Had their competitors already written it? Yes. But Buffer, like Drift, focused on creating a better content mousetrap. It worked.  

Radical transparency and showing your work.

Drift isn’t nearly as transparent as Buffer. For example, they don’t have a transparency dashboard that shares salaries at the company to the outside world. But as Gerhardt told me, they are "very transparent about the way that we work. Everyone shows their work every day."

Consider a typical scenario on a marketing team: a designer is asked to build a landing page, so they work hard and deliver it by Friday. But it's not quite what the team wanted or maybe expectations changed so it gets blown up and not used. But at Drift, the designer would mock it up, take a screenshot, and share it in the middle of the day as a social media post. Again their strategy is more social media vlogger than corporate marketer.

The Drift team believes in faster, daily iterations. One of their mantras is “innovate, don't invent,” which aligns with their philosophy around reusing content as well as borrowing and copying great ideas from other companies. In fact, when people are showing their work internally, they'll often ask "where do you find that? Who did you look to?" They want to see ideas validated by others, if they can. For example, Gerhardt remarked that on their new pricing page that they were happy to take inspiration from great leaders like InVision, another successful B2B company.

Don't farm, hire for fluency

One of the questions our customers ask us most frequently is how to build a content marketing team so I relayed the question to Gerhardt.

He told me it was originally just him cranking out blog posts. But over time, that wasn't scalable. When they finally started to grow their team, Gerhardt never wanted to build a content farm.

At this point what a lot of companies end up doing is hiring 5-6 people fresh out of college to crank out SEO heavy content like 5 ways to do X. While Drift certainly has some listicles, it's not the main focus of their content. The main focus is authentic, narrative driven content. The reason for that, as Gerhardt remarks, is that he's in a tough industry to fake. “We are marketers, doing marketing to marketers,” he said to me, with a laugh.

In making his first hire he looked for someone that was fluent in the language of marketing. He recruited Erik Delvaney, a former content strategist from Hubspot and tasked him with writing 3-4 high quality articles per week. Once he was maxed out, they started thinking about how to expand.

Eventually they hired Gail Axelrod from OpenView Labs, a marketing-focused VC firm. She was already well-known in the industry for her work and came with a lot of experience.

When Axelrod joined she set out to build a blog that felt more like a good business magazine than a content farm. She’d interview Cancel or other executives as if she were writing a story for Bloomberg. Or she’d ask customers like Slack how they were approaching a specific problem. She spoke frequently with her customer success team about the problems customers faced, both related to Drift’s product and not. Her and her team were constantly asking, “How can we turn this into content”?

It’s a far cry from the typical content marketer coming up with listicle ideas in a conference room.

Disagree and commit

One of the last questions that I asked Gerhardt was about his relationship with Cancel and how that affects their content. I wanted to know what they do when two very experienced marketers disagree on strategy.

Gerhardt said “Well, we disagree a lot. But he is… usually right.” We both laughed and then he continued, “One thing we do agree on is to always ‘disagree and commit.’ We borrow that from Amazon. Both parties can make their case, and then on the weight of the evidence and their argument, get mutual permission to move on and go out and do it.” (Compared to most teams that stall when people disagree).

But he told me that it’s important to note any disagreement is temporary. They believe in “Strong opinions loosely held.” As soon as the evidence shows they need to pivot, they do it. There’s no shame in changing one’s opinion.

What's next for Drift

In April 2018, Drift announced a $60M Series B raise from Sequoia Capital. That brings their total funding to above $100M. In press announcements they said they want to build “the Amazon of B2B.” Whether that will come true remains to be seen. But what's clear is that Drift is incredibly ambitious and some of the top investors in Silicon Valley believe that they can make good on that vision.

There’s no better example of that ambition or their commitment to excellence than what I think is the pinnacle of their unique content strategy to date. Today Gerhardt and Cancel are releasing a 300 page book about what they’ve learned building the company.

Gerhard told me, “We spent the last two and a half years creating this category of conversational marketing. Then about a year ago we realized that we need to write about it. We’ve pulled the stories and case studies on it.”

The book is category creation and content marketing at its finest. If you want to learn more about this unique company and their marketing strategy check out the book here.

And if you liked this story, subscribe the our newsletter for profiles of the best content marketing teams in the world.

Michael ThomasComment
The Simple Way To Produce 10x Better Content

Over the last 6 years I’ve published hundreds of stories. They have been read by millions of people and have helped my companies or my customers’ companies generate hundreds of thousands of dollars in recurring revenue. Below I’ve outlined how I run audience research interviews to come up with story ideas.

Traffic analytics for a recent post that we published on Campfire Labs’ blog.

Traffic analytics for a recent post that we published on Campfire Labs’ blog.

When I worked on the marketing team at Highfive there was one meeting every week that I dreaded. The story meeting. It should have been the most exciting meeting of the week, a chance to explore ideas, and think about exciting new stories that we could publish on our blog. But that was never the case.

Each story meeting felt like an exercise in guessing and then trying to meet our customers’ expectations. In hindsight it was absurd. Three marketers sitting in a conference room guessing at what the CIO or VP of IT at a company 100 times our size would want to read. Our goal was to hit the bullseye, to write the story that thousands of IT leaders would share with their network, but our strategy was to put on a blindfold, spin around a few times, and then throw some darts at the wall.

When our Head of Demand Generation, Michael Freeman, joined the company, he suggested a new way to come up with story ideas: “Why don’t we call them up and ask them what they want to read?”

Embarrassingly we had never thought to do this. Sure, we had developed personas based on customer interviews about the pain points our product solved, but we had never asked customers about the problems our content could solve.

Shortly after that we called the CIO of Hubspot, Jim O'Neill. Michael led the call and asked smart questions like, “It’s Sunday afternoon and you’re watching the Patriots game — what are you stressed about?”

Over the course of the next few months we called another dozen customers to ask them similar questions. In doing so we uncovered the cause of our customers’ stress and anxiety and asked questions that revealed their hopes and aspirations. It was a perfect formula for writing content that engaged them emotionally and added real value.

In her AMA on GrowthHackers, Camille Ricketts—the founding editor of First Round Review—explained how simple “Psychologizing your audience” can be:  

“Psychologizing your audience doesn't have to be some big ordeal…I would definitely ask them what kind of information they need. I think that's the key, it's not the content they WANT to see... it's information they feel they NEED to succeed. Where are the gaps they see in front of them, standing between them and their definition of success, or the metrics they want to maximize? How can you help them fill this gap? Really, you're looking to provide utility, utility, utility. I think where a lot of content strategies misstep is providing customer stories, or trying to demonstrate value without considering what their customers' goals are and how they can help with that first.”

After we interviewed our customers at Highfive, we learned that everyone wanted to figure out how to build the best culture on their IT team. With this in mind we launched a new series where we interviewed IT leaders at companies like LinkedIn, Pinterest, and Spotify. In order to write the stories we relayed the questions our customers mentioned in the calls. For example, “We recently talked to Mike at Hubspot and he said he wants to build a culture that can retain the best talent. How have you tried to solve that problem?”

Immediately our website traffic started growing. Whereas our blindfolded strategy netted a couple hundred views per post, our ask-the-customer approach netted as much as 20,000 views on some posts.

A few years after I left Highfive one of my friends, Matt Sornson, called me and asked for help writing a book. As Head of Marketing at Clearbit, he wanted to write about how high growth companies use data to inform their sales strategy. Before ever writing a single word we “psychologized” our audience. In the process we avoided costly mistakes and generated new story ideas.

Customers told us that some of the ideas we had originally brainstormed—like using data to inform email templates—would turn them off the book altogether. We had planned to lead the book with that topic. They also gave us five chapter ideas that we hadn’t considered like using data to coach sales reps or refine a compensation model.

Data-Driven Sales ended up being one of the most popular books in the industry the year that we published it. Hiten Shah, the Founder of Kissmetrics, wrote, “Every chapter shows exactly how a company overcame their challenges and tactical ways you can do the same. Most sales advice in SaaS is generic. This isn’t.” The book generated $30,000 per month in recurring revenue in the first six months.

After seeing the impact of this strategy we started offering to do this research for our customers at Campfire Labs. In every case it has led to important insights and successful stories. In my opinion it’s the best service that we offer our customers. But we realize that we can’t work with every company, so in the interests of transparency and helping people as much as possible, I want to share a simple step-by-step process to run your own audience research interviews.


Step 1 — Define your audience

The first step is figuring out what kind of readers you want to attract. If you have an already defined Ideal Customer Profile use that. If not, run a report on your best customers (most revenue, highest margin, fastest sales cycle, etc), then look at the buyers’ LinkedIn profile and write down demographic characteristics like their job title, industry, and company size.

Your goal is to interview 10-20 “Look-alike” customers or prospects. Imagine these people as nodes on a graph. You want to interview the nodes closest to your best customers, and this may not necessarily be the highest revenue-generating ones. It is worth considering attributes like sales cycle length, product engagement, NPS score, and margin if you have this information readily available.

Step 2 — Send 10-20 customers an email asking for help

Here’s a template you can use:

Hi {{first_name}},

(insert your version of the standard “Hope you’re doing well” stuff we all write in emails)

We’re working on a new series of stories on our blog that aim to solve our customers’ most pressing problems. In order to figure out how to offer the most value and write something that you actually want to read, we’re asking a couple of our favorite customers for help.

Do you have 20 minutes in the next week or two to jump on a quick call and tell us a bit about what you’d like to read?

If you’ve built good relationships with your customers this should be relatively easy. If you’re having trouble or worry about burdening them too much, offer a $100 Amazon gift card.

Step 3 — Interview your customers

When you hop on the call give your customer context on the project.

“Thanks so much for taking the time to talk with me, {name}. As I mentioned in my email, we’re working on a new series of stories on our blog that aim to solve our customers most pressing problems. To pick our topics, we are asking some of our favorite customers what they want to read.

In this call I’d love to learn what problems keep you up at night, what type of content you’re currently reading, and what you’re trying to learn this quarter. The goal of this interview isn’t to figure out what you want to read; I want to know what you NEED to read.”

Sample interview questions

  • It’s Sunday night and you’re watching Netflix — what are you stressed about? What are you worried about in the upcoming week?

  • What are you trying to learn at the moment?

  • What metrics are you and your team measured on that you’re currently thinking about the most?

  • What do you read in order to solve these problems / learn these things?

  • What are your favorite publications (both for pleasure and business)?

  • Are there articles or ebooks you reference often, or frequently send to friends and peers?

  • What is it about those pieces?

  • Can you send me the links to those pieces?

  • Who are some writers whose work you enjoy reading?

  • What do you read or watch for inspiration?

  • Are there common themes among the writing/content you find compelling? (For example, I like Malcolm Gladwell for his ability to make any topic compelling with story, but I realize some people prefer a writer like Paul Graham who gets straight to the point).

  • What types of topics would you like covered in content created by our company?

  • What types of topics do you not want covered?

It’s important to note that interviewing someone is not the same as having a conversation with them. In a 20-30 minute call it’s important to get as much as possible and sometimes that requires breaking the natural flow of the conversation. A couple things to note:

  1. If someone isn’t answering your question, try to politely interrupt (oxymoron?) them and rephrase the question. It’s always helpful to give an example of what you’re looking for.

  2. If you have everything from a question you need, move on to the next topic. Don’t follow their comment up with something like “Oh that makes me think of X.” Just ask the next question.

  3. Ask people to be specific. Passing comments like “I definitely don’t like this X type of content, but that’s obvious so anyway blah blah blah…” can be illuminating if you press for more detail. Say, “Sorry to interrupt, but can you elaborate on that point.” Or if someone mentions a writer by their first name and you haven’t heard of them ask for their last name so you can research them later. Then ask why they like that writer.

Step 4 — Document your findings

Make sure to record and transcribe your calls. Zoom is good for recording calls and Rev is good for outsourcing the transcription. Then create a folder in Google Drive, Dropbox, or whatever cloud storage service you use with the call notes.

Go through the transcripts and try to distill the insights. Look for common pain points, publications, and topics they want to read about.

Pay close attention to the language they use to describe things. You want to write blog headlines, social copy, and content in their words, not yours.

Create a separate document or spreadsheet and add all the pain points, topics, writers, publications, etc.

Step 5 — Turn your insights into story ideas

By this point your mind should be buzzing with story ideas. But if not, here’s a simple way to turn the insights into blog posts. Take every frequently mentioned problem and fill in these blanks:

How {customer} solved {problem}

Now take every metric your customer mentioned and fill in these blanks:

How {customer} measures {KPI}


How {customer} doubled {KPI} in {time period}

Step 6 — Create a style guide and updated persona

In addition to story ideas these interviews will give you more insight into how you should be writing stories. In the publishing world this is referred to as a “style guide.” As you hire more writers and work with people outside your company it becomes more important to document this with examples.

Look at the answers customers gave you to questions like “What type of publications do you like, and why?” or “What do you not want to read?”

I’ve interviewed people who say they want to read engaging narrative stories and people who say they hate Malcolm Gladwell’s storytelling style and prefer writers get to the point. Some readers like lots of data whereas others are overwhelmed by it.

Document these subtleties in a style guide and give examples for writers to reference (ideally stories that your customer gave you in the interview). Make a list of their favorite publications, writers, and stories they’ve bookmarked and aspire to write like that. Writing, like all art forms, is subjective, so figure out what your customer’s idea of a good story is and produce it.

Step 7 — Write stories and ask for feedback

Now that you’ve taken off the blindfold, go and write stories with confidence. Consider using some of the quotes from your customer interviews in stories. Then once you’ve published your stories, send each customer you interviewed an email and ask for two things: feedback and a social share. This follow-up will close the loop and ensure that each story actually solves a real problem.

The above process has helped me and my team write some of our best stories. In aggregate they have been viewed more than a million times and generated hundreds of thousands of dollars in recurring revenue for us and our customers. I believe using the process above anyone with a good product can achieve the same results.

Give it a try and let me know how it goes.

About the author

Hi! I’m Michael Thomas. After selling SimpleData I wrote stories for magazines like The Atlantic, FastCompany and Quartz and helped start a code school for refugees. Now I’m on a mission to fund ambitious social impact projects and help companies tell stories that inspire with new company, Campfire Labs.


Michael Thomas Comment
What I Learned Scaling From $5k to $25k Per Month

On November 6th, 2015 I boarded a flight bound for Buenos Aires, Argentina. In doing so I entered a new phase of my life. Over the last 4 months I had grown my company’s revenue from $5,000 to $25,000 per month. I had also hired a small team and freed myself from the daily operations of the business. For the first time in my life the amount of money I made was no longer tied to the hours I worked.

Freedom, was the idea that came to mind as the wheels lifted off the runway at SFO Airport.

In Part 1 of this series I wrote about the process of starting my business, SimpleData, and how I generated the first $5,000 per month in revenue. In this story I will share how I grew revenue 5x over the course of 4 months and scaled operations. Each lesson includes some backstory, practical tips, and examples you can use to scale your business.  

#1 — “You gotta be Henry fucking Ford, dude”   

Two months before I whispered the word “freedom” to myself on the flight to Argentina, I whispered a different word. Hell. It was 11pm sometime in September and I was feeling burned out.

When I quit my job to work on my business full-time I promised myself that I wouldn’t work late nights. I said I would go camping in the middle of the week. I would live the life of my dreams. But life has a way of altering seemingly flawless plans. In August I doubled revenue from $5,000 to $10,000. And as a solo-founder in a business without a scalable product offering that meant I doubled my workload.

A few minutes after 11pm I answered one last email and stared into space. What am I doing with my life? I thought to myself.

The next morning after hitting snooze a couple times on my alarm I woke up and made a coffee. At noon, after a few more hours of staring into space, going for a couple walks in my neighborhood, and pacing around my house, I called an advisor to ask for help. After listening to me vent about my frustrations he asked me to do two thought exercises that set me on a path to freedom and sanity.

Thought exercise #1
Go to the park with a notepad and answer this question: “What would you do if you had to scale revenue to $50,000 per month in 6 months and could only work 10 hours per week?”

Thought exercise #2
Imagine it’s 1-2 years from now. Make me a presentation explaining why SimpleData just sold for $10 million.

At first I thought the exercises were a waste of time. I had emails to answer, customers to please, and other pressing things to do. But that evening I went to a park by the beach and took out my notepad. One of the first things I wrote was “Hire someone to manage sales and someone else to manage operations.”

Then I hesitated.

For as much as I had talked about passive income and delegating tasks to other people, I couldn’t imagine handing over customers to someone else. I couldn’t imagine anyone else representing the brand.

At this point the genius of these exercises emerged. While they were both hypothetical situations, the answers I wrote down provided a practical roadmap of exactly what I needed to do, which was simple: get over my concerns and hire a team. Thinking about them in extreme examples, like scaling revenue 10x while working half as much, forced creative thinking and radical change.

A couple days later I spoke with Hiten Shah, the founder of Kissmetrics, who stated it more simply: “You gotta be Henry fucking Ford, dude. Turn this thing into an assembly line.”

Need help producing engaging thought leadership content like this? Visit Campfire Labs to learn about my new business.

#2 — Document the process

“Be Henry fucking Ford” is an inspiring quote to stick on the wall, but as a practical goal or strategy it wasn’t very helpful. Luckily, Hiten and a few other entrepreneurs gave me a list of books to read in order to turn my business into an assembly line.

The e-Myth by Michael Gerber introduced me to the idea that a business has three types of people.

Technicians — People who produce the thing a business sells. In his example of a bakery this is the person who wakes up at 2am to put the dough in the oven.

Managers — People who manage the technicians, set goals and manage processes. In the bakery example this could be a store manager that makes sure that costs stay low and inventory is purchased at the right time each month.

Entrepreneurs — People who set the vision for the company.

According to Gerber most entrepreneurs get stuck in the technician role forever. For some people, like a baker that loves their craft, that’s ok. But for others it becomes hell. I fell into that second category.

Rather than think about new products to offer customers or come up with new marketing strategies I was stuck answering my customers emails, managing our virtual assistants, and taking sales calls. I desperately needed to hire my technicians and managers.

But what role should I hire for?

In order to make that decision I needed to figure out what work I was doing to serve every customer. What activities was I doing everyday and what skills would be required to perform those tasks?

Per my advisor’s recommendation I sat down one day and thought about the step-by-step process of working with each customer from the first moment they hit the website to the moment they happily refer us to their friend.

Here’s the Evernote I put together.

If you’ve ever taken a programming class you may recall the first “algorithm” you built. The professor probably told you to document the steps required to make a peanut butter sandwich. Then maybe you wrote something like:

  1. Grab bread

  2. Spread peanut butter

  3. Spread jelly

But designing algorithms is all about specificity. Where did you find the bread? What type of bread is best? What happens if you grab the heel of the loaf? These are all things you need to tell the computer program. Documenting business processes is no different.

My business was simple: we asked customers what type of leads they needed and then told virtual assistants how to find them and sent them to the customer. Bread, peanut butter, jelly. Yet, the process outlined in that Evernote was 47 steps long.

This is the Evernote where I outlined the entire customer journey. Note: this is only the first half which documents the sales and free trial process.

This is the Evernote where I outlined the entire customer journey. Note: this is only the first half which documents the sales and free trial process.


You can also convey this information visually. Here’s a flow chart of the customer journey at Campfire Labs that we recently designed:

flow chart

#3 — Create specific job descriptions and scorecards

In this process I realized that my work was broken down into two categories: operations and sales. So I set out to hire two people.

Quickly I found someone that looked perfect. She had worked at Zirtual, a similar company to ours, and had a lot of experience managing operations.

That same week my parents came to visit me in San Francisco and my Mom gave me some of the best hiring advice I’ve ever received. She had recently started a flower shop and had run into problems managing people. When I told her that I was hiring someone she asked if I’d written a job description and scorecard to measure their work.

“Of course I have,” I responded.

“I don’t mean the job description you posted online. I mean an internal document for you to know after a month if she’s doing the job you hired her to do,” she said.

Reluctantly I followed her advice.

In my job description I had written, “Manage customer emails.” This was the equivalent of writing “Grab bread.” After a month how would I know if she was successful? How could I trust that it was getting done properly? I had no system for answering these questions.

With my Mom’s help I rewrote all the job responsibilities. For example, “Manage customer emails” became:

Manage customer emails

Check my email in the morning and organize by urgency, then take care of any easy emails or questions that she is trained to answer

Create tasks in Trello based on emails that I need to respond to

Success: if she helps me develop a system that keeps me in email for no longer than 30 minutes a day by the end of the first two weeks I’d consider that success. Secondarily, if she helps get the response time per customer down to 2-4 hours, that’d be a success.

By designing a job description and scorecard with this level of specificity I could confidently delegate the task and measure her effectiveness. For example, I could use a time tracker like RescueTime or Harvest to know how long I was spending in email everyday. Or we could set up a help desk software to measure response times and know how well she was communicating (most software has a feedback button at the bottom of every email conversation).

My Mom had helped me build my first assembly line and create a system to measure its output.

Over the next month I was able to document and delegate 90% of the business’ activities. I hired two people and freed myself up to work on the business instead of in the business as e-Myth author Michael Gerber says.


#4 — Continue doing things that don’t scale

While I was hiring the team that would eventually take over sales and operations I also spent a lot of time trying to grow revenue. By July I reached $5,000 per month. As I mentioned in Part 1,  most of that revenue came from “Doing things that don’t scale” and being scrappy. I sent really personalized emails, took friends out for coffee, and helped people with no clear idea of how it would help me. But by August I decided that it was time to start doing things that would scale.

That was a mistake.

The first channel I tested was Facebook ads. I spent a few hours one day writing copy and building profiles in the Ad Management tool. Then I entered my credit card, set the budget to $500, and waited.

In order to run a few tests simultaneously I tested ads on LinkedIn too.

Quickly I started seeing new people on the website and watched my Cost Per Click (CPC) closely. At first it seemed promising. $1-3 per click isn’t bad I thought to myself. At the time my conversion rate on the website was 5%. I did some back of napkin math and guessed it would cost $20-60 per new lead. And I was converting 25% of leads into customers paying between $500-2,500 per month. With those numbers I could acquire a new customer at $80-240 and make my money back immediately. But that’s not what happened.

After spending about $1,000 on ads and getting hundreds of targeted visitors I didn’t see a single conversion.

After a few weeks of testing I decided to go back to what had worked in the past and get scrappy again. I emailed an old boss and a couple friends and offered to help think through their outbound sales strategy. I started asking for referrals on sales calls. I sent hyper-personalized emails to companies that I respected.

And it worked.

My old boss introduced me to his new VP of Marketing and I closed a deal that ended up being worth $30k over the next 4 months. My friend introduced me to his Head of Sales and Marketing and I closed a deal worth $10k.

After seeing success again I started thinking about how to scale up the strategy based on what I knew best: outbound sales.

#5 — Double down on what you know best

After talking to dozens of prospects and customers I started to realize a trend in the people buying our product. One day I reviewed all my call notes to create a more targeted ideal customer profile. I wrote down two broad categories:

Startup founders that don’t have time to prospect but want to find new customers.

Sales teams that need to hit a high quota and find a way to accelerate lead flow, pipeline, and revenue.

This ideal customer profile gave me demographic information to look for (tech industry, small company, B2B, etc.) But I knew the real opportunity was combining this with behavioral data. The behavioural element is the buying signal which tells you whether or not they might need your service. I needed to find a trigger that indicated a company’s need for prospect lists.

Then it hit me. A company hiring a sales development rep (SDR) would likely need prospects for that SDR to email and call. And all of those companies list open positions on sites like LinkedIn, Craigslist, and Suddenly, I had a combination of demographic and behavioral data to run a targeted email campaign.  

The results were staggering: 22% of the leads I emailed replied and I generated $4,800 / mo in net new monthly revenue.

Here are the instructions I sent our virtual assistants and the email templates I used:

Step 1 — Go to Linkedin jobs section

Step 2 — Go to “Advanced Search”

Then enter the following:

Job title = “Sales Development Representative”

Country= “United States”

Please prospect the following job titles at all companies that are hiring an SDR:

  • VP of Sales

  • Director of Sales Development

  • Sales Development Manager

Email templates

Subject line: Your SDR position on LinkedIn

Hi {{first_name}},

I noticed your open SDR position on LinkedIn and wanted to reach out.

For the last year I was an SDR at Highfive. I learned everything I know from Aaron Ross and Max Altschuler. And during that time I realized how many hours I was spending building lists.

I decided to leave Highfive and start a company that enables companies to outsource their prospecting. As you grow your SDR team does that seem like something that would be useful?

Would love to get your feedback, and get you started on a free trial if it makes sense!


57% open rate

10.7% response rate

Subject line: Persistent founder

Hi {{first_name}},

“Energy and persistence conquer all things”

Quotes like that always get me fired up! Read that one this morning on GoodQuotes and thought I’d reach out to you again.

Do you have 7 minutes this week to touch base and see if there is a mutual fit between SimpleData and {{company}} regarding lead generation?

I also feel like a great sales email should have puppies in it so…

(image of cute puppies..)


48.1% open rate

2.7% response rate (ouch!)

Subject line: Should I call for help?

Hi {{first_name}},

I’ve reached out a couple times and have not heard back which tells me one of three things:

1. Everyone at {{company}} is all set on the prospecting front.

2. You’re interested in SimpleData, but haven’t had the time to respond.

3. You are being chased by a hippo and need me to call for help.

(image of hippo chasing man)

Please let me know, as I am beginning to worry…


46% open rate

8.9% response rate

The entire campaign led to about 10 conversations and $4,800 / mo in net new monthly revenue. Most importantly though, it was a repeatable strategy that could be delegated since dozens of sales jobs are posted on sites like LinkedIn, Craigslist, and others every day.

After documenting the activities in my business, hiring two people, and building systems to measure their output, I decided it was time for a stress test. In November I packed my bags and boarded my flight for Argentina. The 5 hour time difference meant that I would no longer be available to take customer calls or answer my team’s questions at all hours of the day. But more than anything it was a mindset shift, a clear separation between my time working in the business and my time working on the business.

At first I was worried. Would customers be upset if I didn’t respond immediately? What would they say when I told them I was unavailable for calls and introduced them to the salesperson I hired? Would my team make mistakes?

But there was a much more important question to ask. “What could I gain?”

Before leaving for Argentina I read a Tim Ferriss blog post that I’ve come back to many times since. In it he wrote, “Once you realize that you can turn off the noise without the world ending, you’re liberated in a way that few people ever know.”

The questions I wasn’t asking myself were: What would it be like to not wake up every morning to a flurry of emails? What would it be like to take a couple days off and drive up the coast of Uruguay? What would it be like to finally have time to write the stories I wanted to write?

When I didn’t answer my customers emails immediately some were probably unhappy. I’m sure we lost a few of them. We probably missed a few opportunities to close deals. But that was a small price to pay for a new life of freedom.

Over the course of the next year I worked on my business for about 5-10 hours per week. I spent the rest of my time traveling, reading books, and pursuing a childhood dream of writing for magazines (a process I wrote about here). By letting a few bad things happen I freed myself to achieve the big things that meant so much more to me than an additional $1,000 here or there.

In Part 3 I’ll break down how I sold the business one year later. Stay tuned for more.

About the author

Hi! I’m Michael Thomas. After selling SimpleData I wrote stories for magazines like The Atlantic, FastCompany and Quartz and helped start a code school for refugees. Now I’m on a mission to fund ambitious social impact projects and help companies tell stories that inspire with new company Campfire Labs.

Michael Thomas
How I Built A $5,000 Per Month Side Project

Passive income. The 4 hour work week. The dream. As a millennial there are few things that rank as desirable as finding a recurring source of income that doesn’t take much work (or a boss). In April of 2015 I decided to seek that out and build a side project that could pay my bills while I read books and traveled the world. Within a few months I achieved my dream and booked $5,000 in monthly recurring revenue (MRR).

It’s been almost 3 years since I started SimpleData, my passive income muse. I grew the business to $30,000 per month in revenue within six months, automated and delegated just about everything, and for all of 2016 I worked an average of 5-10 hours per week. My new freedom enabled me to spend five months living in Argentina and then Europe. It afforded me the time to study things like history, political science, and other liberal arts that I felt I missed after dropping out of college. This muse changed my life.

In January 2017—18 months after starting the business—I sold SimpleData. It’s hard to imagine what my life would look like today if I didn’t sit down at my computer one night back in 2015 and come up a plan to quit my job, make passive income and travel the world. This simple act put me on the path to financial independence and wealth. It gave me the time and money to volunteer and give back, which opened my mind to a set of questions I never thought to ask previously—about my responsibility to help people less fortunate than me, about the work that makes me happy, and what to do when those two things are in conflict. This path also led to depression, social isolation, and the hardest time of my life, which previously I’ve been hesitant to share. (Is there anything worse than a rich guy complaining about his life?)

In this 3 part series I’ll break down how I built and sold my business, including how I came up with the idea, found my first customers, scaled operations, and found potential acquirers. I’ll also share some of the more personal things that I learned along the way and how I learned to calm some of the demons in my head.

#1 — Monetize your brain

The thesis of the project was simple: take what was in my head and monetize it. In other words, build a business that leverages all of the skills that I had learned over the first three years of my career in entrepreneurship, marketing and sales.

When I started SkyRocket — my last (failed) startup — I solved someone else’s problem which meant the time-to-market was significantly longer and the investment had to be much larger. I had to stay up late in the night reading industry journals just to be on the same playing field as my competition. In my second go-around I didn’t want to do that.

With that in mind I decided to solve a problem in the sales development space. At Highfive I made a name for myself as a “saleshacker” by applying some basic web scraping and front end development to my job. I had carved out a niche by applying what I knew about technology to sales. This was my unique skill, and I wanted to monetize it.

#2 — Find the pain

Finding a skill that I could use as leverage pointed me in the right direction, but in order to actually make money I knew I’d need more clarity. I needed the specifics of what problem I would solve, who I’d solve it for and how it would make money. And all of that could be found if I were able to answer a simple question: what do people in sales development need, and is there any pain in the current process of achieving that?

As I thought about problems to solve I remembered a story one of Highfive’s account executives told me. She was $5,000 short of quota (her quarterly revenue goal) and the only way to hit it was to email and call as many people as she possibly could to see if they needed video conferencing. In order to get that list of people she stayed up until 1am and built a prospect list (a spreadsheet of people to reach out to). 1am is painful. 1am is opportunity for improvement.

When I took over the Sales Development effort at Highfive the first thing I did was hire a team in the Philipinnes to ensure I never had to stay up until 1am building lists — or build any lists for that matter. I made a couple videos with instructions, bought some tools and found a virtual assistant on oDesk named Jonathan. For most sales development reps building lists can take two hours out of their day. I had eliminated it entirely.

When I put two and two together I realized that sales development outsourcing was an idea worth pursuing. If I could prevent salespeople from having an end of quarter frenzy like my co-worker, I could probably make a buck.

Need help producing engaging thought leadership content like this? Visit Campfire Labs to learn about my new business.

#3 — Competition isn’t always a bad thing

In March of 2015 I decided that I would build a sales outsourcing side project. The goal would be to provide a turn-key service for sales teams to request leads. But there was a problem with the idea: the market was highly competitive. Whenever I told people about what I was building they replied, “Oh something like [competitor].” Most people I spoke with told me I shouldn’t build the business for this reason. That’s when I learned play #3.

Most people in the tech industry are brainwashed by Silicon Valley group think. These people believe that every business must have a billion dollar opportunity. This isn’t true, especially for side projects. In fact, when pursuing the passive income dream competition is your friend. Let me explain.

Competitive markets are by their very nature mature markets. And the more mature a market, the less time and money a business has to spend educating that market on the problem. Think about real examples. Coca-cola isn’t spending money on ads telling you why you should drink soda. They spend money telling you why Coke is better than Pepsi. Soylent — the future of food startup — on the other hand must spend money educating people on why they should drink their food. In order to succeed, Soylent will have to spend tens of millions of dollars and years in the market.

Creating a new soda to compete with Coke would take less time and money than creating a new food and beverage category entirely (like Soylent). Coke has spent billions educating people on why they should drink soda. And you could educate people on why they need to drink your soda. You could pick a small niche that Coca-Cola executives see as a rounding error ($1-10 million) Granted, the long term opportunity may be smaller. That’s besides the point. The passive income dream isn’t about making billions, it’s about making thousands per month and doing it quick.

So is it better to create a “future of food” side project or a soda side project? I put my money on the mature, yet competitive market.

#4 — Find a position in the market

By April I decided that competition wasn’t going to stop me from starting a sales outsourcing startup. But in the back of my head I heard the voice of one of my mentors — Highfive’s VP of Product Marketing. I recalled a lesson he gave me during a 1:1 at Backyard Coffee in Redwood City.

When you hear Volvo what comes to mind? Scandanavians, but more importantly you probably think “Safe car.” How about Honda? Odds are “Reliable car” came to mind. This is the basic idea of positioning. What comes to mind when people hear {company name}?

The concept of positioning is incredibly important when starting a business because it determines who will buy your product. A product with no positioning that sells to “everyone” is likely to sell to no one. That’s because people need to identify with your product and brand in order to buy.

To put this in context I’ll give an example of positioning in my life. I no longer buy Abercrombie and Fitch because they position themselves as the high end clothing brand for middle schoolers. I do buy from Urban Outfitters though because as Highfive’s VP of Sales liked to say, I’m a wannabe “urban hipster.”

Previously I thought positioning was just another business school buzzword. But it’s important. At it’s core, positioning means “Pick a niche to get rich.” Isn’t the entire point of a side project to get rich?

In order to find a unique position in the market you must look at the competitive landscape. When I looked at the lead generation space I realized that companies fell into three categories:

Platforms:, Hoovers and DiscoverOrg are all examples of companies that charge annually for a set amount of lead exports from their platform. These databases are sold to thousands of companies which means everyone is emailing the same person. This results in worse response rates for their customer. And the average cost is about $30,000 per year (billed upfront). Ouch. Bad data for a high price.

Service-as-a-service: LeadGenius is an example of a company that charges annually for a team that prospects for you. Great concept, but their business model is built to work for them, not the customer. The cost is about $24,000 upfront ($2,000 per month billed annually). Not so great for a startup on a tight budget with changing business needs.

Freelancers: oDesk and Elance are examples of platforms where you can hire your own virtual assistant team to prospect. Customers have to train their team and the billing is variable so your cost per lead ranges from $.50 to $5. Cheap entry point, but time intensive and unpredictable.

I knew that there was an opportunity to create a turn-key service with a pricing model that customers could love. And thus, the first pay-as-you-go lead generation service was born.

4 hour post img 1.png
4 hour post img 2.png

#5 — Reverse the Way You Want to Sell

At the end of April a friend of mine introduced me to someone who needed help building prospect lists. After work one day I prepared for my first official sales call. Fortunately I had sold mobile apps in college, and helped develop Highfive’s first call deck so I was able to take what I knew and build a five step sales process (see play #1):

~2 min — (Rapport) Ask how their day is going. Tell them how we were introduced and see if we have any common connections.

~1 min — (Our value prop) Give a 30–60 second pitch on what value SimpleData offers. (Note: the goal isn’t to sell them. You want to assure them this call is worth their time and then ask them questions.)

~5–10 min — (Context and qualification) Say the following: “I want to be respectful of your time and make the best use of it so I’d love to ask a few questions about what you’re looking for in order to steer the conversation in the best direction.” Then ask a series of “probing questions” that identify their pain points. Ask what products they currently use, what their sales and marketing goals are this year and how they currently go about building prospect lists.

~5–10 min — (Solution) Explain how SimpleData fits into their current sales and marketing process, how it can help them hit their goals, and how it makes their prospecting process more efficient. The key here is that you pitch the product in their language. If they say they are under pressure to hit quota, emphasize that your product helps sales teams under pressure to hit quota. If you repeat their question in a statement you’re on the right track.

~5 min — (Pricing and next steps) Tell them about our pricing and free trial program. Ask the prospect what would make a trial successful? In other words, what can I do to win your business?

It’s important to note that I didn’t do any selling until about halfway through the call. I speak with a lot of founders who have their first call process backwards. They get on the phone, build some rapport and then sell. Then they ask, “Does that sound like it will work for you?” This makes for an unpersonalized pitch that is hard for a prospect to relate to. When you say that you help small businesses do XYZ they think “We’re a mid-size company, so this won’t work.” Then the last half of the call is spent backpedaling and rephrasing your pitch.

I spent the first 15 minutes of my first sales call asking questions. When asked to describe SimpleData I resisted the urge to sell and instead offered a very high level value proposition. “SimpleData helps businesses spend less time doing busy work so that they can spend more time selling.” What person doesn’t want to spend less time doing busy work so they can make more money? My initial pitch was high level enough for anyone to relate to it. After this brief description, I peppered my prospect with questions that would give me the context to personalize a more in-depth pitch later.

Ultimately this sales process helped me land my first 5 customers. But you’re probably more interested in where I found them in the first place. That leads to Play # 6.


#6 Get Scrappy and Do What You Know

When friends ask me where I found my first 5 customers I have a hard time describing it any other way than responding, “I was scrappy.” Paul Graham would call this Doing Things That Don’t Scale. Here’s what that meant for me and how it lead to $5,000 / mo in revenue.

As I mentioned, my first lead/opportunity came from an introduction. That was made possible when I took a couple friends (who are salespeople) out for drinks to tell them what I was working on. Afterwards they both said they would try to think of people to refer me to. My first customer closed 2 days after the introduction was made (referrals always have a shorter time to close). My first customer came from the simple concept of asking friends for help.

My next two customers came from a less obvious channel. A friend told me about a service called Growth Geeks and suggested I create a profile for my service. I was hesitant at first because it seemed like a distraction, but I signed up nonetheless. After receiving a couple marketing emails from the company I sent this email to the founder:

4 hour post img 3.png

He responded that day and asked if I had time to speak on the phone. On the call I learned that he had a customer who needed 2,000 leads a month and they needed 2,000 leads a month for themselves. I used the same sales process as my first call and closed two deals in 30 minutes worth $3,000 / mo (25% of the $4,000 in revenue went to Growth Geeks). Suddenly I went from $1,000/mo to $4,000 / mo.

Later that week I decided it was time to double down on this side project. I spent a couple nights writing email templates and planning outbound email campaigns. By May of 2015 I had sent over 30,000 sales and marketing emails so I knew how to get high response rates (see play #1). I knew outbound email (also called direct sales) would be an effective customer acquisition channel. I also had experience with it so I spent all my energy over the next month on this channel.

I sent emails to about 500 people over the course of a month which resulted in ~20 free trial sign ups. Two of those free trials converted within the month and by the end of June I had $5,000 in booked MRR.

Many marketers (especially at startups) make the mistake of trying too many channels (social media, eBooks, webinars, paid ads, etc.) at once. The result is a lack of focus and steep learning curves. This delays what I’ll call time-to-ROI in a similar way that market maturity delays time-to-market. The marketer or founder would be wise to focus on a couple channels early and expand when one of the following conditions is met:

  1. You have exhausted the channel (e.g. you’ve emailed your entire customer segment)

  2. You have developed a repeatable process that can be executed by an employee or contractor.

In summary, here’s what channels those first customers came from:

Being scrappy — 3 customers ($4,000 / mo in revenue)

Outbound email — 1 customer ($500 / mo in revenue)

Content marketing — 1 customer ($500/mo in revenue)

#7 Don’t Lose Perspective

The last play in this playbook isn’t about market positioning, sales technique or growth hacks to help you find customers. But I think it’s the most important play.

Late one night after reaching my first $1,000 / mo in revenue I received an email. It was from my first customer and immediately I knew it wasn’t good. I had sent him 100 leads that morning before work and he emailed me to inform me that nearly every one of them was outside of his ideal customer profile. For my business this is the equivalent of a 24 hour server outage. My heart rate increased, I felt my palms get sweaty, and I stormed into my room to investigate what happened.

Eventually I solved the problem, called my customer, and refunded the $100. He wasn’t stressed at all. He realized he was an early customer and the road would be a bit bumpy. So while I was freaking out imagining the end of the world as I knew it, my customer was probably watching Netflix with his family.

That night I lost my sense of perspective. I had forgotten that this was a side project, that it was early stage, that all problems can be solved. And so I ruined one night of my life.

I’ve probably ruined 100 nights over the last three years due to similar problems — an email from my boss, a server outage during my last startup, rejection from an important prospect. In retrospect all of those problems were tiny and none of them were worth boiling my own blood over.

Today, I remind myself that work is a sport. It’s not life. Whether you’re working on a startup, side project or contributing to a larger company, the place where you work should be a place where you go to grow, interact with people, and have fun. It should never be a place where you experience unhealthy stress, anxiety or fear.

At the end of June 2015, with $5,000 per month in revenue and a new sense of confidence, I quit my job to work on SimpleData full-time. In part 2 of this series I’ll describe the path from $5,000 to $25,000 per month in revenue. In part 3 I’ll share the story of how I sold my business. If you want to read these stories, enter your email, and subscribe below.

About the author

Hi! I’m Michael Thomas. After selling SimpleData I wrote stories for magazines like The Atlantic, FastCompany and Quartz and helped start a code school for refugees. Now I’m on a mission to fund ambitious social impact projects and help companies tell stories that inspire with new company, Campfire Labs.

Michael Thomas
The Art of Pitching: How I Got Published in The Atlantic

Over the last two years I’ve written for national magazines like The Atlantic, FastCompany, and Quartz. In this post I’ve broken down the process I used to break into these publications. My hope is that it will help people like you get your ideas published and build your personal or company brand.

Two years ago, I returned to my hometown of Denver after five years away. I didn’t tell anyone except my family that I’d returned, and for the next two weeks I holed up at my parent’s house. No, I wasn't another discouraged millennial moving back into the basement – I simply decided it was time to achieve a childhood dream and get published in a national magazine.

During those two weeks I did nothing but read books and write magazine pitches. I told myself that I wouldn’t leave until one of my pitches was accepted. Over the course of 14 days I sent 14 pitches, and finally on August 9th my first story was accepted by Quartz. A couple weeks later my second story was accepted by The Atlantic. Then I landed another story with Quartz. A couple months later I started contributing to FastCompany regularly.

What inspired this crazy routine? To put it simply I wanted to share my ideas and experiences with millions of people. For years I had written blog posts about what I was learning as an entrepreneur. On average hundreds of people would read them — maybe thousands if I was lucky. I knew that if I wanted to build a personal brand and generate awareness for my company I’d need to get my ideas in front of a larger audience.

In hindsight, the path to success was relatively straightforward. The only thing that prevented me from doing so in the first place was myself. Self-doubt and the notion that only “real writers” could write for major magazines stopped me from taking the first step. Once I overcame my doubts and learned the process of pitching I started getting published in national magazines. With the prestige associated with names like The Atlantic I had the opportunity to meet with the founders of companies like Kickstarter. My stories started hitting the front page of Reddit and HackerNews. Last summer I achieved my goal and passed one million cumulative views on my stories.

Below I’ve outlined the exact steps and resources that I use to get published. My hope is that it will help you build your brand and get your own stories in front of millions of people.

Learn from the best pitches

Every profession or skill has its own element of “insider’s baseball.” In the publishing industry, there’s a proper way to pitch stories. To learn this, I started reading articles on how to pitch. At first all I found was fluff pieces, and light blog posts sharing truisms that told me what I already knew: “Keep it short, and tell a good story.” That was no help. What I needed was the exact formula and set of actionable steps to get editors to respond.

In one of the fluffy articles I read I saw a link to a pitch database called The Open Notebook. There I found a list of about 100 successful magazine pitches next to the published story that they became. It was an incredible find.

Before finding The Open Notebook, I hardly knew how to structure a pitch. Sometimes I sent entire stories (note: never do this). Other times I sent something along the lines of “I’d love to write a story about artificial intelligence. Are you interested?” (why I thought this was a good idea, I’m not sure.)

The Open Notebook enabled me to analyze the best practices of 100 successful pitches by some of my favorite writers. My number one takeaway was how to create a character-driven story hook.

A story hook with characters

One of the things that surprised me the most was how beautifully written some of the pitches were. They included characters, plots, and everything else that a real story has. In other words, the core of the pitch was storytelling. In hindsight that seems obvious, but at the time it was a revelation. I thought a pitch had to be formal and short. I learned that it should be a shortened version of the story that I’d eventually write.

Here’s an excerpt of a successful pitch that I wrote using that framework:

Over the course of 550 days, Casey Neistat became one of the Internet’s most famous celebrities. His daily vlog became one of the most popular and talked about channels on YouTube, attracting 6 million subscribers. He won GQ’s New Media Star award in 2016, produced one of the year’s most viral videos, and then crashed the Oscars. Then on November 19th he shocked the YouTube community that adores him so much and announced the end of his vlog.

In the first decade of his career, Neistat straddled the line between filmmaking’s established world and its less critically respected fringe. As soon as he achieved commercial success, premiering films at Sundance and selling a TV series to HBO, he pivoted. Over the next five years he straddled the line between the filmmaking world and tech. By 2014 he was spending all of his time producing viral hits like the video of him snowboarding in New York City. The next year he started a Snapchat competitor, Beme, which he sold for $25 million at the end of 2016. Each time the world expects Neistat to do one thing, he does the exact opposite and achieves wild success.

In his latest pivot Neistat wants to use his influence and filmmaking skills to make the world better. It’s cliche, he admits, but the man who achieved Internet fame by preaching platitudes like “Do what you love” and “Don’t worry what others think” has never shied away from the borderline trite. Up until now, Neistat hasn’t shared his plans. He has said repeatedly that he is excited about the democratization of technology, but how he’ll contribute is unclear. Neistat has agreed to speak with me to share some of his plans.

In this pitch I was able to hook the editor with a question: why did Neistat end his vlog? Rather than answer it in a sentence I provided more character development, sharing snippets from his career. The pitch also had inherent conflict that appeals to FastCompany’s audience (between the established media world and the independent creator movement). The pitch ended with a larger question: what will this character (Neistat) do next? In other words the pitch had every element of a good story: characters, plot, and meaning.

I learned much of what I know about storytelling a couple years ago from a video interview with This American Life’s Ira Glass.


Explain why it matters

One of the most important element of a good story is meaning. You can tell a story in which a character does something (plot) in a place (setting). But without meaning it’s going to fall flat like a bad joke. In fact, comedy is a great place to learn how to tell stories.

Andrew Stanton’s (writer/director of Toy Story) explains this brilliantly in his TED Talk on storytelling. He gives the following example:

A tourist is backpacking through the highlands of Scotland, and he stops at a pub to get a drink. And the only people in there is a bartender and an old man nursing a beer. And he orders a pint, and they sit in silence for a while.

And suddenly the old man turns to him and goes, “You see this bar? I built this bar with my bare hands from the finest wood in the county. Gave it more love and care than my own child. But do they call me MacGregor the bar builder? No.”

He points out the window. “You see that stone wall out there? I built that stone wall with my bare hands. Found every stone, placed them through the rain and the cold. But do they call me MacGregor the stone wall builder? No.”

He points out the window. “You see that pier on the lake out there? I built that pier with my bare hands. Drove the pilings against the tide of the sand, plank by plank. But do they call me MacGregor the pier builder? No. But you fuck one goat…”

The old man at the bar describes three events — things that he’s done in his town. Then he hooks us by suggesting that he has a nickname. By the third event we’re invested in the story and curious what his nickname is. I assume I don’t need to explain what the “Aha moment” in this story is. But the point is that every event in that story led to it.

Every magazine pitch needs its own “Aha moment.” It needs that moment where you go “Oh man, that explains why…” In telling a story you often need to engage in discussion around a larger event or trend, while connecting it to a truly interesting narrative.

Relevance > interest

One day, soon after returning to Denver, I randomly read about how America controls a majority of the airplane manufacturing industry. I wanted to know how and why so many prominent airlines were started here and what entrepreneurs like myself could learn from it. In my research I found an amazing story about how Bill Boeing started Boeing and United Airlines and launched the entire aviation industry as we know it.

Unfortunately a great story isn’t the only prerequisite to getting published. Timing and relevance to “the news cycle” is another essential ingredient. Here are the first two paragraphs from a pitch that led to one of my stories in The Atlantic to show you what I mean:

On Saturday SpaceX will send a communications satellite by the name of Amos-6 into space. The launch will be the company's 33rd and it is just one of 40 that SpaceX has planned in the coming years.

30 years ago, a private company shuttling more satellites into space than NASA would have seemed crazy to all but a few in the aerospace industry. By the 1990s space travel seemed a distant dream shelved by governments overwhelmed by swelling deficits. Today, the dream of visiting far off planets is alive again though, thanks to private companies like SpaceX.

Notice that I don’t even mention Bill Boeing or the aviation industry in the first two paragraphs? Instead I found an event that could make the story relevant to the day’s news. That answered the question “So what?” and created a timely reason for telling a history of aviation in America.

The next day Amos-6 exploded on the launch pad and my story suddenly became even more relevant. Hours after the explosion I followed up with the editor. He responded immediately and I landed the story.

Before writing for magazines I avoided daily news like the plague. As an entrepreneur it was full of noisy distractions. But in deconstructing the pitch process I learned how important it is to have a finger on the pulse of current events.

To really understand that idea put yourself in an editor’s shoes for a second. You get 30-50 email pitches everyday, and you have a boss breathing down your neck asking when the next viral story is coming. You have endless deadlines, hotshot reporters to manage, and a constantly shifting 24-7 global news cycle. Sound easy?

Prior to my first couple pitches, I didn’t take an editor’s interests into consideration. I was thinking about the pitch from my perspective – instead of thinking about it from theirs. Not thinking from the decision-maker’s perspective is a key mistake that people make in every facet of life from sales to job interviews. It really hit home for me when I received the following email from an editor after I pitched a story about how corrupt the early airline industry was and got this response:

Thanks so much for your pitch and sorry for the delay in getting back to you. This sounds like a great story but in the absence of interesting 'so-what' style lessons or implications, I'm going to pass. Let me know if you think I am missing something.

The key to pitching is always asking “So what? And who cares?” Your editor certainly will.

Pitch consistently

Once I thoroughly learned the structure of the magazine pitch, and got feedback from a few editors, I felt a new confidence. After sending my first pitch, and receiving a rejection, I asked for feedback. The editor — a writer that I really respect — told me that he really liked the pitch, but it wasn’t relevant to his audience. That response and other words of encouragement prompted me to I start sending pitches everyday.

Holed up in my parents’ house, I was able to create an entirely new schedule for myself.

  • Each morning I’d wake up around 7am, drink coffee and eat breakfast with my dad, and then start reading.

  • After about an hour of reading I’d feel eager to start jotting ideas down.

  • Then I’d take those ideas and start doing research to see if anyone had written about them.

  • From there, I was able to outline a story.

  • Later, in the afternoon, after making lunch, I’d research the story and get enough material to develop pitch.

  • By about 4pm, I’d have a fleshed out outline that I’d run by my Dad, who is an avid reader.

  • Next, I’d take his feedback and write up a pitch.

  • By 5pm each day I would send a pitch and then log it in my pitch tracker.

As someone who used to be in sales, I knew the power of tracking my “pipeline.” That’s where the idea for a pitch tracker came from. Each day I’d log my pitches, and when I heard back I’d update them. Simply seeing the pitches logged in a spreadsheet forced me to pitch everyday and track my progress. And I knew if I missed a day then I’d feel that same anxiety that woke me up in Iceland.

(I won’t write more about routine since I think this has been covered a lot already. But the long and short of it is this: pitch every day, work hard, and be persistent. It took me 7 pitches before I got my first story accepted).

Good pitching means writing well

Of course, I’d be remiss to not mention the importance of one last thing in the pitch process: which is that good pitching is also about writing well. I’ve already mentioned that storytelling is the core of any pitch. But so is good grammar and sentence structure. Your prose needs to be as readable as your stories are engaging. Of course, that is something that only comes with practice. There is no shortcut, no easy hack, to writing well. But fortunately there are about ten bazillion books on the subject. On Writing Well by William Zinsser is a particularly great one. John McPhee’s Writing Life Archive is equally brilliant (and free).

Another way to learn how to write well is simply by reading more. Every morning I read for about an hour. Every night I read for about 30 minutes before going to sleep. When I sit down to write I hear other, more experienced, author’s voices in my head. If a sentence isn’t grammatically correct I don’t notice it because I know all the rules of the English language. I notice because it doesn’t look like Michael Lewis’ writing or a story in The New Yorker. The way I see it, every time I sit down to read, my brain slowly unravels the English language. Then, when I go to write, it references that information.

About the author

Michael Thomas is the founder of Campfire Labs, the best way to hire the top 1% of writing talent. He previously founded and sold SimpleData, a lead generation company. Michael also writes for magazines like FastCompany, The Atlantic, and Quartz.

Michael Thomas
How to Write Longform Content That Goes Viral
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On September 25, 2013 Alex Turnbull sat down at his computer and hit publish on a blog post that he’d been thinking about for a long time. For the last six months his company, GrooveHQ, had written content that Alex would have described as “B content.” It was a lot of “10 things about xyz”, “Great quotes to live by” and that jazz: the type of content that your marketer friend shares on Facebook because her company makes her do it. 

When Alex hit publish he knew that he was doing something bold, something that would change the direction of his company. But he didn’t expect, in his wildest dreams that it’d receive the sort of attention that it did. That day he introduced a new GrooveHQ blog. He promised readers that he’d share every lesson he learned on his company’s journey to making $100,000 per month in revenue. 

On November 25th, 2014 at 2:14pm EST — slightly more than one year after Alex hit publish and began sharing the details of his Journey to $100k — GrooveHQ reached its stated goal. Another two years later Alex reported that his company had reached a $5,000,000 annual recurring run rate (ARR). 

Read enough of Alex’s blog posts and you’ll start to see a couple themes. The first theme you might notice is the occurrence of the word “value.” Alex is evangelical in his devotion to the startup philosophy that a company exists for one reason and one reason only: to create value for its customers. He gets on calls with all of his customers. He constantly asks for feedback. It’s evident that he goes to bed thinking about how to improve the lives of his customers, and wakes thinking about how he can help them achieve their goals. But that’s not necessarily unique in today’s world of tech. 

What sets Alex apart from his founder peers is his devotion to transparency. The GrooveHQ blog didn’t invent “marketing by transparency” as a movement or tactic, but ask anyone in the industry and his blog is the one people point to as the best example of it. 

In August of 2015 I decided to run a little experiment. I’d followed the success of the GrooveHQ blog and wondered if there was anything unique about Alex that made his blog posts such a success. Would it be possible to write my own story and get the sort of reception he’d received (or even a fraction of it). 

A couple months prior I’d started a side project. I’d learned my fair share of business lessons. For example, technical chops aren’t a necessity to launch a company; and it’s possible to earn $5,000 per month without working long hours. With some of those lessons in mind, I decided to write a couple blog posts.

One Thursday I took my computer outside, where I didn’t have any Internet access, and started pounding away at my keyboard. I wrote everything I’d learned over the last few months. I tried to explain what experiments I’d run, and describe some of the emotions of running a company. Then I tried to weave it all into a story. The next day I posted my story and waited. 

Within a couple hours I had 5,000 visitors to the site (more than 5 times the amount I’d received in the three months prior). By Saturday I had 15,000 visitors. My email inbox was filled with 200 free trial requests. That blog post, and the short series that followed it eventually earned my company about $25,000 in revenue. It was early traction that gave me the confidence to keep building. 18 months later, I sold that company, and those early blog posts were a big reason for my success.
When I launched a new company recently, I decided that I’d build it on the same content marketing acquisition strategy that I’d experimented with back in 2015. In the first few weeks I wrote three blog posts. They received a combined 30,000 unique visits, and all three hit the front page of HackerNews and Reddit /Entrepreneur. So in shameless Alex Turnbull fashion, I’d like to share what I’ve learned about writing content so far:

Tell human stories
Of the three blog posts that I’ve written, two have earned about 80% of the traffic. The other one received about 1/10th the traffic of those other two. And the reason seems pretty straightforward. While the top performing posts were stories about me — stories about my personal successes and failures — the other one was a story without a compelling narrative. It was too long to be useful (because it required 5 to 10 minutes of reading), and it was too short to engage readers in something of substance. 

One of the things that Alex writes about so frequently at Groove is the importance that transparency has played in his success. His blog took off as soon as he started writing stories about the real trials and tribulations that come with starting a company. He achieved success as soon as he stopped writing like a company, and started writing like a human being. But this is hardly a new concept. 

Every great story from the beginning of time has been a human story. From Homer’s Odyssey to Coelho's Alchemist, the narrative of every story is remarkably consistent: a human faces problems and solves them to achieve what they want. Sometimes the arc of a story is simple: the character faces one problem and solves it. Other times, the story unravels like a series of brackets opening in a math equation. Throughout the story, brackets are closed and new ones are opened. But regardless of style, every single story has this structure at its core. 

Think about even the simplest of stories that we tell each other in the office: 

This weekend I went up to the mountains because I’d heard the snow was good (character has indirectly stated that he/she wants to ski on good snow). But when I got up there the snow was awful and there were crowds all over the mountain (character has now directly stated the problem). So my buddy and I went to the backcountry and found powder below Lift 10 (character solves the problem). 

Now that’s a bad story because it’s too simple. There’s no complexity of emotion expressed by the character, no unexpected surprise, or punchline. But it’s a story with a beginning, a middle and an end. And that is better than 90% of the corporate blogs out there. 

For some reason when most marketers begin blogging they forget everything they know about storytelling. They post content like “The 10 things you didn’t know about XYZ” and stupid quotes that have already been written bazillions of times. Maybe it’s because they see the success of a Buzzfeed or Upworthy and don’t understand the intense engineering that goes into that stuff. Or maybe it’s because they’re lazy. But I will tell you from experience that posting content without story rarely works (more on the exception to this rule below). 

The problem with a blog devoted to quotes and fun facts is that it doesn’t hook anyone. People don’t fall in love with quotes, they fall in love with the characters that wrote them. Hell, a blog post about Winston Churchill’s best vacation would be better than a quote featuring his writing. 

As a general rule of thumb, your content will fall flat if it doesn’t have one or more of the following: 

  1. A character with complex emotions that other people can relate to

  2. A character that has expressed their desires

  3. A beginning, a middle and an end (chronological dates are a good starting point)

Write about other humans
One of the things that frustrated me so much when I first moved to Silicon Valley and began my career as a marketer was the fact that I hadn’t accomplished anything. If you’d told me that the key to marketing was telling great stories, it wouldn’t have helped. I didn’t have a story to tell. It was a loop that seemed impossible to break since everyone I asked told me that one way to achieve success was to write a blog like Alex’s. To that I replied, “Thanks for the idea, but I DON’T HAVE ANYTHING TO WRITE ABOUT SINCE I’M 19 YEARS OLD.” 

In hindsight this was a silly excuse. My mistake was thinking that in order to tell human stories I had to write about me. 4 years on, I understand that there are about 7 billion other humans that have interesting stories. 

In doing research for my new company I stumbled across a blog called IndieHackers. If you’re reading this by way of HackerNews you’ve probably heard of it. If not, here’s the five second summary: A guy named Courtland interviews people that have started successful side projects and companies. He asks them what challenges they faced, and how they overcame them (sound familiar?). The thing that separates IndieHackers from the pack is the transparency that Courtland requires every interviewee to agree to. In each story he accompanies the lessons learned with analytics screenshots. 

In just six months since started IndieHackers Courtland has interviewed an astonishing 75 entrepreneurs. As of December 2016, his site receives 200,000 unique visitors each month, which is pretty remarkable considering that most “professional marketers” (emphasis on the quotes there) aren’t able to achieve that sort of success. 

IndieHackers succeeds because Courtland tells stories that are both inspirational and practical. Every entrepreneur can relate to the subjects of each profile. They describe similar problems, and explain how they went about solving those problems. Instead of writing fluff like “Be persistent and don’t give up,” Courtland digs deep and gets entrepreneurs to share their fears, hopes, and struggles. In doing so he evokes emotions that are core to the human experience. 

Be different (but not that different)
Of course, it’s easy to think that the time has come and gone to write a Journey to $100k blog, or interview successful entrepreneurs. Maybe you’ve read a competitor’s blog and thought, “Shoot, they already beat us.” But this is silly. Most things in life have already been done. Yet every year new blogs with the same premise start and go viral. That’s because humans don’t really want to read anything that unique. They want to read something safely in between original and familiar.

When Matt Ogle and his team at Spotify launched Discover Weekly, the company’s amazing recommendation engine, they accidentally shipped a few bugs. As a result the algorithm suggested songs that users had already heard (at a rate of about 1 old song to 10 new ones). When his team removed the bug, they noticed that engagement dropped. In other words, Spotify users wanted a little bit of consistency mixed in with their new music. 

As The Altantic’s Derek Thompson wrote recently, this was due to a psychology phenomenon called “Most Advanced Yet Acceptable.” The concept of MAYA was discovered by Raymond Loewy, an industrial designer in the mid 20th century, who designed cultural icons such as the Exxon logo, the Lucky Strike pack, and the Greyhound bus. As Thompson wrote:

Loewy had an uncanny sense of how to make things fashionable. He believed that consumers are torn between two opposing forces: neophilia, a curiosity about new things; and neophobia, a fear of anything too new. As a result, they gravitate to products that are bold, but instantly comprehensible. Loewy called his grand theory “Most Advanced Yet Acceptable”—MAYA. He said to sell something surprising, make it familiar; and to sell something familiar, make it surprising.

In other words, it should come as no surprise that IndieHackers — a blog doing what many blogs have done before — could achieve success. Sure, Alex wrote about GrooveHQ’s lessons learned. But had Courtland come to the conclusion that he had to create something 100% original he wouldn’t have told the story of 75 other entrepreneurs with interesting stories and complex lives.

Reverse engineer prior success
Understanding MAYA also enables marketers to take the guesswork out of the content creation process. One could theoretically analyze what is similar amongst the most successful stories online, and create something similar (but not too similar). HackerNews, Reddit, and Twitter make this “reverse engineering” incredibly easy: 

For a list of “successful outcomes” (blog posts that get lots of traffic), we can sort by the Top content on Reddit’s /Startup subreddit

Unsurprisingly, successful content in this subreddit falls into two categories: 

  1. I made (or didn’t make money) and here is why

  2. Here are resources that helped my business succeed

The first category proves that story is essential to success in this channel. But the second category raises a question. Does every single piece of content need to be story driven? 

If I apply the same process of analysis to my Mom’s floral business, I notice that her audience isn’t always sharing stories about florists or brides-to-be. In fact, the most popular results for the search “wedding flower” don’t have a single story-driven post. 

In looking at these results it's immediately clear that people searching for wedding flowers want to see images of beautiful bouquets, or they want to learn how to design their own. And that leads me to the exception to my story rule.

A couple years ago I attended Hubspot’s Inbound conference and saw Camille Ricketts speak on the topic of content marketing. At the time she ran First Round Capital’s blog, which was one of my favorite places on the Internet. In the talk she mentioned something that has stuck with me for the last three years. 

She said that, in all the millions of data points they’d analyzed, they learned people really only share content for one of three reasons: 

  1. It evoked emotion (a laugh, cry, etc)

  2. It taught something useful

  3. It represented the reader's prior beliefs

Think about your own social media feeds. There are funny cat gifs and emotional stories about the trials of life (emotion). There are explainer videos and articles that distill the complex into something more comprehensible (useful). And there are tons and tons of politically driven posts (ideology). But is there really anything in between? 

This helps to explain why Buzzfeed and Upworthy have amassed so many page views from articles with 100 words or less. Rather than take the story approach to their content, they try to reverse engineer the reasons why people share content. They do this by designing content that makes readers feel nostalgic (which Harry Potter house are you?) or by creating content that people can share to express their beliefs. 

In my experience I’ve had success with two types of content: (1) data-driven articles, and (2) story-driven articles. As an example of a data focused piece of content look at this article I wrote in 2016. There is very little content. But the data and visuals tell a story that evokes emotion: surprise. It’s hard to look at those graphs and not think holy shit! This piece of content also taught people something that they only intuitively believed before. That is, it gave people data to prove that Bill Gates is doing amazing work. It even represented people’s beliefs a bit. Many of the people that shared this story (roughly 250 people shared it on Twitter in the first two weeks) were entrepreneurial and ethically-minded. Sharing this on their Twitter or Facebook was a statement. It said, “I care about philanthropy.”

The content that succeeded most on SimpleData’s website (my last company) was always story-driven. How I Built a $5k/mo Side Project in 5 Months was successful because it taught people how to start a business with real examples. I explained why I thought a growth experiment would work, and then shared the results. The people that viewed, upvoted, and then shared this content did so because they wanted to help their peers. It was a vote that said, “This will teach you something. It’s worth reading.” 

While useful content, and ideology-focused articles work, I believe that they are the exception to the rule and rarely, if ever, succeed in a silo. When The Knot, a popular wedding blog, shares photos on Pinterest for inspiration, their goal is to bring people into a funnel. Ideally brides-to-be read and share the photos and then subscribe to the newsletter. Then TheKnot keeps their audience engaged with longer narrative-driven stories about brides and the process of getting married. The photos that get brides in the funnel are a small part of a larger brand narrative; they aren’t the be-all end-all. 

I think one of the reasons that so many marketers write boring “10 things you didn’t know about XYZ” content is because they see the success of The Knot, or another blog like it and look only at a small part of the company’s content strategy. Then they copy a component, and not the entire system. 

This past weekend I was introduced to the YouTube filmmaker Casey Neistat, and quickly became obsessed. In one of his videos, he addressed a frequent question: how do you make good movies? He answered by sharing a popular diagram in the film world. I think the same diagram applies to some extent to marketing (with a few swapped parts and pieces of course). There’s no which way around it, story is at the core of every marketing activity that a company does. 

Michael Thomas