How to Write Content That Hits the Front Page Every Time: A Longform Guide to Content Marketing


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 (yesterday), I sold that company, and those early blog posts were a big reason for my success.
When I launched a new company two weeks ago (this one!), 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 two weeks I’ve written three blog posts. They’ve received a combined 30,000 unique visits as of writing, and all three hit the front page of HackerNews and Reddit /Entrepreneur. Those posts have been the sole acquisition channel for the $2,400 in revenue to date. 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. 

Screen Shot 2017-01-11 at 11.06.36 AM.png

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. 

How I Built a $5,000 Per Month Side Project

Passive income. The 4 hour work week. The dream, as my cousin referred to it recently. 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 this year I decided to give “the dream” a shot and set out to build a side project that could pay my bills while I watched Netflix.

Last month I booked $5,000 in monthly recurring revenue (MRR). I’m on track to double that this month. And what started as my 4 hour work week dream has turned into a new way of work, and of life. 

This is the story of how I came up with the idea, found customers and built a business in one of the most competitive markets in business. I’ve structured it as a playbook and my hope is that it will help you build your 4 hour dream. 

Play #1 — Monetize your brain
The thesis of this project was simple: take what is in my head and monetize it. In other words, build a business that leverages all of the skills that I’ve learned over the last three years of entrepreneurship, marketing and sales. This gave me a foundation for what to look for in business ideas. 

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. This time 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. 


Play #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.

Play #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 I bump into in San Francisco 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 specifically. 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. 

Play #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 Abercombie 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 “mission 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 there 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!

Play #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 his day is going. Tell him 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) Tell him that I want to make sure I direct the conversation in the best possible way and in order to do that I’d like to ask a couple questions. Ask what products they currently use, what their sales and marketing goals are this year and how they currently go about building prospect lists. (Note: this usually encourages the prospect to tell you their problems and what they are looking for).

~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. 

~5 min — (Pricing and next steps) Tell him 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. 

Play #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. And I thought I’d describe 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:

He responded that day and asked if I had time to speak on the phone. On the call I learned that he was one of the guys behind Growth Hacker TV (so cool!) and 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. (To date about 30% of those have closed as paying customers) 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 chasing too many rabbits. They pursue 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 is SimpleData’s distribution of customers and revenue by lead source:

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)

Play #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 derive unhealthy stress, anxiety or fear. 

I started SimpleData to gain financial freedom. My goal was to replace my salary so that I wasn’t dependent on it. At the end of June I gave my two weeks. I wanted to live a life of balance and felt that a side project was the bridge to that. 

It’s been almost two months since I left the company. In that time my hours have ranged from 10 to 40 hours per week. I’ve taken 3 vacations, spent most of my time working outdoors, and still managed to double revenue. I’m on track to bill $10,000 in revenue this month. But this is not my greatest sense of pride — it’s the way I’ve done this and the calm mentality I’ve kept that I’m most proud of. What started as a side project has become a new way of work, and of life. And it’s one that I encourage everyone to explore. 

I'll post Part 2 later this week which details how I went from $5,000 - 10,000. I also plan on writing a series of articles about the process from $10k onward and how I sold the business. 

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

Getting published in a national online magazine or site like The Atlantic is a great way to gain exposure for your ideas and products. It’s also a great way to build credibility and personal brand. This year I deconstructed the pitch process, and learned how to maneuver the publishing world. The result: my stories are getting published in The Atlantic, FastCompany, and Quartz.

15 minute read

Last summer, on a small island in Iceland, I awoke in the middle of the night with a sudden angst. I don’t recall if a dream sparked it. Maybe it was a night terror. My Dad said that I woke him up earlier in that night sleep talking some gibberish. But whatever it was, the angst suddenly prevented me from sleeping. 

That angst that kept me from sleeping in Iceland would eventually inspire me to pursue and achieve my goal of publishing a story in a national magazine. For the entire year prior to that night I’d felt as though I was stalling. In January I told myself that I wanted to be a published journalist. But by July I’d hardly published a thing, let alone landed anything in a national magazine. 

After spending a week in Iceland I went on to Paris and then Switzerland to bum around with a friend. But the entire trip that anxiety persisted. I felt like I was wasting my life, pursuing someone else’s ideal. Today’s culture of “conspicuous experiencing” and #blessed travels told me that I should spend my money and time traveling the world. But all I wanted to do was write stories for magazines. After a couple weeks my friend and I called the trip short. At a touristy pizza restaurant, surrounded by other “experiencers”, we decided that it was time to pursue our own visions of the good life. 

In August I returned to my hometown of Denver after four 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. During those two weeks I did nothing but read books and write magazine pitches. I told myself that I wouldn’t leave until I’d had one of my pitches accepted. 

Over the course of 14 days I sent 14 pitches, and finally on August 9th my first story was accepted by Quartz. Shortly afterwards another story was accepted by The Atlantic. Then I landed another story with Quartz. And a couple months later I started working with FastCompany. 

In hindsight the path to success was relatively straightforward. For three years I told myself that I wanted to publish magazine stories. And for three years the only thing that prevented me from doing so was myself. Self-doubt, writer’s block, and this notion that only “real journalists” could write for magazines stopped me from taking the first step. But once I did, the next dozen steps were easy. 

However, I’d be lying if I said it was only self doubt that prevented me. Like every profession or skill, magazine writing has its own element of “insiders baseball.” There’s a proper way to pitch stories. Some stories are obvious fits to a magazine editor, but what makes it obvious can be impossible to decipher for an inexperienced writer. Ultimately writing for national magazines was about two things: understanding how “the publishing machine” works, and understanding how my own machine (my brain) works.

Below I’ve tried to detail the exact steps I took and resources I used over the last couple months:

How to Write a Magazine Pitch
The first step that I needed to take in order to break into magazine publishing was understanding the rules of the publishing establishment. I needed to understand the system to break into it. Immediately, I realized that the pitch process was the first gate that I needed to pass. So I started reading articles on how to pitch. At first all I found was fluff pieces, and light blog posts 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. 

I found that formula on the Metro one day in Berlin just before coming home. 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. This was incredible. 

Prior to finding The Open Notebook I hardly knew how to structure a pitch. Sometimes I sent entire stories (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?” The Open Notebook enabled me to analyze the commonalities among 100 pitches by some of my favorite journalists. 

I saw that every pitch had a few common components:

A story hook with characters
One of the things that surprised me so much 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 I’d eventually write. 

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

"Did you hear that Levels is settling down in Amsterdam? Apparently the father of digital nomadism is no longer a nomad."

After launching and RemoteOk, Pieter Levels became the face of the digital nomad movement. Online he could be seen posting photos from Thailand one day, and tweeting from Miami the next. His blog quickly became a place of inspiration for despairing office workers stuck at their 9-5. But two cliches tell Levels' story best: first, the grass is always greener on the other side, and second, actions speak louder than words.

I’ve been a digital nomad for the last year, and if there has been one lasting lesson it is this: nomadic tribes settled down for a reason. Every nomad I’ve met goes through the same phases. In month one it is euphoria and excitement at following one’s dreams. Then in month two and three it’s frequent moments of questioning. The homesickness sets in, the new friends and cities get old. And eventually everyone reaches phase three: existential despair — the same kind that inspired them to leave their 9-5. That’s when they pack it in and their Airbnb account goes dormant.

In this piece I plan to tell the stories of digital nomadism that don’t make headlines or self-help blogs. I plan to interview influencers like Pieter Levels, Joel Gascoigne, and others who have built personal brands around the digital nomad movement, but in recent months have settled down.

In this pitch I was able to hook the editor with a question: why did Petier stop traveling? Then I told a short series of events that hinted at why he stopped. “He did this, and then that.” In doing so I also described a character. But most importantly I described why it mattered. I tied Pieter’s story to a larger trend that Quartz’ readers would be interested in. (Note: In writing the story I learned that Pieter didn’t stop traveling. He just changed the way he did it. But it still made for an interesting story).

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 questions I forced myself to ask before every pitch was: So what? In other words, what’s the point of writing this story? In asking that question I tried to put myself in the editors shoes. Why would they want to publish the story? What problem was I solving for them? It’s essential to attach meaning, or significance, to your pitch. This is not dissimilar to the way storytelling works in real life. 

When I was a teenager I had a habit of running my mouth a lot. There was hardly a moment that I wasn’t telling a story or joke. But one of the things that always bothered me was how frequently my stories or jokes fell flat. I’d say, “This happened, and then this happened, and then this happened.” And my audience would look at me in silence for a couple seconds as if to ask, “Are you done?” Other times I’d tell a story and people would erupt into laughter. But success in storytelling at that time of my life was a total black box. 

After college I learned the components of a good story and the importance of the punchline. One of the best examples of this that I’ve seen came from Andrew Stanton’s (writer/director of Toy Story) TED Talk on storytelling. On stage he gave 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…”

As I wrote on my blog a couple years back, “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, this explains why…” In telling the story you need to describe a larger event or trend. For my Quartz pitch it was why traveling the world wasn’t all it’s made out to be. 

You can view Andrew Stanton’s full TED talk here:

Dig in the archives and tell unique stories
Another reason that an editor might want to run a story is because it’s irresistibly unique. If you haven’t noticed, the Internet, for all its beauty and splendor is an echo chamber. The same stories get told dozens of times in only slightly different ways. Part of this is because humans themselves don’t actually want that much variety in their lives (see this story on What Makes Things Cool). But part of that is the reality that finding unique stories is hard. It requires digging in archives, interviewing lots of people, and chasing leads that don’t always pan out. This is an opportunity for anyone willing to put in hard work.

One day shortly after returning to Denver I ran across a story about Icelandic Airlines that explained the origin of their stopover program. That led me to ask the question of why America controlled a majority of the airplane manufacturing industry, and why so many prominent airlines were started here. All of the stories I read led to a book that wasn’t available online. So I started calling around. I found a bookstore owner who lived in the mountains. He told me that he was going to be in Denver that night at an art festival. So I drove downtown and met him. That night I stayed up late reading stories about the pioneers of air travel. 

The stories I found in that book led me to pitch two stories. One would take a month to find its home (in The Atlantic), and the other would take another four months to find its home (in FastCompany). In order to add color to each of those stories I had to find books in libraries and dig up old Popular Mechanics magazines from the 1960s. It was fun work, but it was a rabbit hole. I had to invest time, and have faith that I could piece all the strings together into a cohesive story and then place those stories in magazines. 

Here’s The Atlantic pitch and story that research ultimately resulted in: 

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.

Shipping satellites into space for governments and large corporations is only phase one in a much larger plan for the company, however. Over the next two decades SpaceX hopes to transition to passenger space travel and send humans to Mars. And in doing so, it will borrow from a strategy developed 90 years ago by a man who we might consider the Elon Musk of the 20th century.

In the 1920s the young aviation industry looked much like the private space industry today. Costs were prohibitively high for everyone save the ultra-wealthy and governments with large budgets. But a group of entrepreneurs and politicians dreamed of a world where passenger travel was accessible to the masses, and very quickly afterwards they saw those dreams come to fruition. Few shaped this history more than an ambitious businessman from Seattle named William Boeing.

Like Elon Musk, Boeing faced a problem of economics, a chicken and egg dilemma of sorts. To make passenger travel profitable his company had to charge the equivalent of tens of thousands of dollars adjusted for inflation. That severely limited the market. The best way to bring down costs was economies of scale, however. It was a tricky Catch-22 any capital-intensive industry faces at the start. 

Boeing solved this problem by bidding on mail contracts from the US postal service. But the novel business strategy that set him apart from his peers was how he intended to transition to the potentially lucrative passenger air travel business. In 1927 Boeing launched the Model 40A, a plane capable of flying mail and two passengers. He charged each passenger $900, or roughly $8,000 today. This second income source enabled the company to charge less for mail, which enabled Boeing to win more contracts and thus further reduce their costs. A virtuous cycle ensued, and soon Boeing became the largest aircraft manufacturer in the world. By 1933 the cost of a ticket from New York to San Francisco was $160 and the new passenger air travel industry was born.

It’s easy to be skeptical about SpaceX’s passenger travel aspirations. The leap between near-Earth orbit and Mars is not trivial. But in studying the aviation industry of the late 20s and early 30s, a time when costs were reduced dramatically and the passenger airline industry was born, it is possible to imagine trips to Mars in the near future. In this article I intend to tell the story of aviation’s innovative, and sometimes corrupt, beginnings. My sources include Bob Van der Linden, a leading historian at the Smithsonian and author of Airlines and Air Mail, and other aviation experts. 

Would you be interested in a piece on some of the parallels between the two companies in their first 10 years of operations and how the price of space travel might come down in the same way air travel did in the early 20th century? 

If so I'd be happy to write a more thorough pitch with facts on the parallels between the two industries and a plan of attack for research/investigation. I can also research different lessons / implications if you'd like. 

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

When I drove down to meet that bookstore owner in August I could have never predicted that a rocket would explode a month later and lead to my story being published in The Atlantic. I could have never predicted that all that research into Popular Mechanics archives would result in a story about an entrepreneur that dug a plane out of a glacier, or that the story would get picked up by FastCompany. But hard work yields opportunity and opportunity is the foundation of luck. My pursuit of original stories was the key to landing both pieces. 

Explain how you’ll report the story
In looking at successful pitches I noticed something odd. In every pitch it seemed that the last paragraph explained how the reporter would go about gathering the source material. This was something that I’d never read on any blog or heard a reporter talk about. But out of 100 pitches it seemed that 80% had a paragraph about how the reporter planned to get material for the story. 

In the follow up that I sent to The Atlantic after Amos-6 exploded I edited the intro and also included my methodology: 

In this article I plan to tell the story of how America’s passenger airline industry was born essentially overnight. In doing so, I will parallel Boeing’s rise to prominence in the 20s and 30s to that of SpaceX’s. My sources include Bob Van der Linden, a leading historian at the Smithsonian and author of Airlines and Air Mail, and other aviation experts. 

In a story about Iceland’s tourism industry I wrote: 

In this story I intend to tell the story of Iceland’s exponential tourism growth in recent years. I have sources at The Ministry of Tourism, Statistics Iceland, Icelandair Group, and The University of Iceland’s tourism department. I’ve done extensive research on the tourism industry in Iceland in preparation for a longer article about the founder of Icelandic Airlines. 

These paragraphs give an editor confidence that the journalist is serious about the story and willing to report the facts. Very few magazines want opinion-pieces, so the methodology shows that a pitch isn’t some fluff piece without facts, data, or reliable sources to back it. 

Think like an editor
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. 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. That’s 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: 

Hi Michael, thanks for reaching out. 

I like/appreciate the irony of Iceland being unable to enjoy the fruits of its Euro 2016 success, but the country's enormous tourism growth has been written about a fair amount over the last year or two, so we'd need to find something new to say about it or its impact. This could mean a fallout story about how tourism growth is reshaping other parts of the economy, or a look at the people who have to adapt the country for the new tourism demand... most important, we'd just want to get beyond the straight growth story. 

Another time 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.

After a couple more of these I learned that editors want to break new stories, and those stories need to be relevant to a larger conversation in society. A story on airline corruption would be relevant if there was a scandal that got people talking about corruption. But in the absence of any current event my story was 100 years past its prime. 

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

Pitch consistently
Once I 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. With that and other words of encouragement I started sending pitches everyday. 

By holing 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 get a story outline. Then in the afternoon, after making lunch, I’d research the story and get enough material to send a pitch. By about 4pm I’d have an outline that I’d run by my Dad, who is an avid reader. Then 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. I knew if I missed a day then I’d feel that 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 is good writing
Of course, I’d be remiss to not mention the importance of one more thing in the pitch process: that is that good pitching is good writing. 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. Every book or story is an input that the brain analyzes for commonalities. Everything I write is an output of all that collective information organized in my own unique way. So it seems my subconscious has been doing for years what my conscious was finally able to do when I got ahold of successful story pitches. And I believe that is why seeing those examples was what I needed to finally break through the ceiling that was preventing me from my goals. 

How to Validate Demand for Your Product — Part 2

Before you build a product it's essential that you test whether or not people want it. Part 1 described how to do initial research. This post explains how you can test your hypothesis with real data (and ideally make some money doing it!). Read below to see the results from the test and what I learned.  


Last week I wrote an article titled “How to Validate Demand for Your Product.” In it I described my process for evaluating business ideas. I explained how I use Google Keyword Tool, Reddit, and Twitter to see if an idea is worth pursuing. That was Part 1. The next step in the process of business model validation is to test your hypothesis with real data. Enter: Conversion Rate Testing. 

As some of you realized (and pointed out on HackerNews), the blog post that I wrote was in itself a business model experiment (meta, right?). In writing that post I was hoping to get traffic to my new website: Up Up Grow, an online marketing course. I wanted to test conversion rates and see if anyone actually wanted the course. So I thought it’d make sense for Part 2 of this series to share the results and explain how I did that. 

First things first, here were the results from the test (and my first week of live testing):

Unique visitors: 15,862
Visits to course landing page: 720
Course sign ups: 13
Conversion rate: 1.8%
Email newsletter sign ups (leads): 120
Revenue: $902.50

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An Introduction to Pretotyping
To most it seems kinda weird to advertise a marketing course that doesn’t even exist. It almost seems Donald Trump University-ish. But I’d argue it’s weird for anyone to do otherwise. 

One of the people I mentioned in my last post was a mentor named Alberto Savoia. He taught me everything I know about business model validation. When I was a 19 year old college dropout trying to find my way in Silicon Valley he took me under his wing. At Google, he coined the term “Pretotyping” which is the idea that before you build a product you should test demand for it. 

As an early engineer at Google he discovered that many of Google’s products weren’t taking off. People had heard of Google Maps, Search, and Adwords. But some of their products just weren’t working. So Alberto decided to figure out why. 

During his research he learned that the process most engineers took was Build, Ship, Test. They’d come up with a great idea, and then immediately start solving the difficult technical problems. Then the design team would polish it up, and send it to marketing. Then they’d drum up a bunch of interest and ship the product. After an initial spike in users many products quickly became obsolete. Alberto guessed that the reason was because no one had taken the time to test whether or not people wanted the product in the first place. And thus pretotyping was born. 

Coincidentally Alberto began his work at roughly the same time that Eric Reis began writing The Lean Startup. While Reis’ book went mainstream, Alberto’s attracted a more cult following. But the concepts are more or less the same: don’t build a product before you know people want it.

To Alberto (and Reis), a business should reverse their product development process: rather than rush to build a product, they should first test demand for that product. Then using a simple landing page and some marketing dollars they should get real data to validate their hypothesis. 

Applying Pretotyping to Up Up Grow
With Alberto’s words in the back of my mind I decided to test demand for my online marketing course. I knew going into it that there was a lot of competition in the space. But still, I felt like there was a gap. So many people teach students how to market a product with a big budget, or consultants. I wanted to launch a course that founders could use to reduce their customer acquisition cost (CAC) to less than $100. 

With Up Up Grow I skipped the process that I outlined in Part 1. I’d already spoken with about 100 people about the idea so I knew that there was some demand out there. But I wanted to make sure that those people weren’t just encouraging me. Any time humans rely on qualitative data they risk getting biased feedback. When I ran the idea by people they said they’d buy it, but how’d I know whether or not they were just being nice? What I needed was unbiased data to tell me whether or not I should spend weeks designing a course. 

Building a landing page
Last week I launched the website using Squarespace, Unsplash (for images), and The Noun Project (for icons). I setup a Stripe account and listed my course as a product on the site. All told it took me about 2 hours to get the site live. 

The next step was to get traffic to the page in order to test conversion rates. 

Getting traffic
In order to get traffic I wrote a blog post (part 1) and posted it to HackerNews. From my previous company, SimpleData, I knew that a HackerNews post could get tens of thousands of site visits if it hit the front page. So I wrote the post with that audience in mind. I looked at the front page and analyzed the headlines that got the most upvotes. The goal was to reverse engineer what had already worked. A blog post describing how to validate demand for a product seemed to make sense. 

I hit publish last Thursday and crossed my fingers. I was at my parents house eating dinner when my phone started buzzing. By the time I logged on later that evening the story was #2 on the front page. A couple minutes later I got an email from Stripe telling me that the first student had signed up. 

Over the next day I also got a constant stream of emails from Mailchimp indicating that people had signed up for the newsletter. So that night I decided to email them and see if they had any feedback on the course. 

I wrote: 

Hey new Internet friends, 

In the last couple days you signed up for my newsletter after reading this blog post on How to Validate Demand for Your Product.

I have to say HackerNews is a wonderful place (minus the comment trolls of course). I posted the article on Thursday night, and three days later 15,000 of you have read the story.

Like many of you, I'm trying to validate a new business model here and I want to soak up as much information as possible. So I have a quick question --  Is there anything stopping you from buying the course right now? 

One of my hunches is that the pricing isn't right. Or maybe the course curriculum (what you'll learn) isn't clear. Or maybe that picture of me scared you away :) 

For the first 10 people that respond I'll give 50% off the already discounted $95 price as a token of my appreciation. 

Anywho, I'm going to get off my computer and enjoy the holiday now. In the meantime let me know if I can help you with anything growth related!

The email got a 78% open rate, and 12% of subscribers responded. The responses ended up being GOLD. One person responded to let me know that they were confused about when the course would begin. I emailed back details and they purchased an hour later. Someone else responded that they wanted more information on what would be taught. Again, I responded and they converted. In total 7 newsletter subscribers converted, which was further validation that I was onto something. 

Crunching the data
Of course the most important metrics I looked at were revenue and conversion rate. With $900 of revenue generated from a single blog post I knew the business model would be viable. Last week I spoke with a top-notch blogger that charges $250 for data-driven stories. With that in mind, I validated that the business could scale without me. 

The conversion rate is important because it gives me a sense of what kind of customer acquisition cost I can expect in the future. Here’s a simple example to make that concrete: 

Let’s say my friend runs a blog. He approaches me and tells me that he is willing to show my course to his readers. But he wants to charge me $.10 per click. Should I advertise with him? 

At $.10 per click, 100 clicks would cost me $10 (duh). And if the same conversion rate (1.8%) held, I could expect to sign up 1 or 2 students, which would net $95 to $190 in revenue. That’s a no brainer.

At $1 per click I’d have to think harder about it. I’d acquire 1-2 students for $100. If the conversion rate slipped I’d barely break even.

Regardless of the exact numbers, my conversion rate gives me a benchmark to start plugging in numbers. In further research into the market if I learn that industry CPC costs are $5 then I know that I’m in trouble. Conversely if I learn about marketing channels like my friend’s blog that offer $.10 CPC prices then I know I’m in business. At that point my only bottleneck is capital to invest in the channels. 

Of course, conversion rates change based on the channel and audience, but with this blog post I was able to get a ballpark estimate. Going forward I’ll be able to continue testing and ideally raise the conversion rate by targeting audiences better and writing more content on the site. 

What’s next?
After validating demand, the next step is to start growing revenue. In order to do that there are a couple metrics to manipulate: 

  1. Traffic -- Theoretically if I increase traffic by 10x I should get ~100 sign ups.
  2. Conversion rate -- If I continue to get the same traffic I could also try to double my conversion rate. Again, that should theoretically double the students I sign up per day. 
  3. Course price -- I could also test the price. This is a classic microeconomics optimization problem to solve: if I double the price do conversion drop by more or less than 50%. If it’s less than 50% I should theoretically double my price and keep it there since net revenue would grow as a result. 

In the next blog posts I’ll discuss marketing channels that I’m testing and a few paid ad campaigns I plan to run. As always I’ll provide as many examples and real data as possible. Sign up for the newsletter if you’re interested in hearing when that is published. 

How to Close More Customers with Predictive Analytics

Put simply, "Predictive Analytics" is the act of analyzing data in order to predict buying behavior. It's a tool that sales and marketing teams can use to reduce CAC and sales cycle length. The idea is simple: if you can get to someone right before they buy, you'll save time (and money). In this post I'll explain how to use Predictive Analytics to close more customers this year.


A couple weeks ago my ex-manager and mentor wrote an article on LinkedIn that put words to something that’s been in the back of my mind for the last two years of my life. I had an “Ah-ha” moment. An epiphany. As I read the article, I realized I’ve been thinking about sales outreach all wrong.

The article introduced the concept of behavioral data. Have you heard of it? I had, but I wasn’t thinking about the power of this concept in building an ideal customer profile, prospecting, or writing email templates. In the next 1,300 words, I’ll deconstruct what behavioral data really is (with examples) and then explain how you can use it to grow your business or hit quota.

Behavioral data is a tool you can use to identify buyers at the right place, and right time. If you’ve ever done sales before, you’ll understand that it’s all about context. Have you ever sent a cold email and received a response like this?

Michael, Great timing. We’re evaluating lead generation companies right now. Are you available tomorrow at 9am?

If so, you’ve experienced the power of behavioral data — most likely by happenstance and out of sheer luck. The goal of this article is to take the uncertainty and luck out of the equation and start building predictable outreach strategies.

What is Behavioral Data?
There are two types of data that marketers and salespeople generally think about.

Demographic data: This is data that describes static characteristics of a business. In other words, these are data points that don’t change frequently. Examples of this include: company location, industry, number of employees, etc. Think LinkedIn advanced search.

Behavioral data: This is data that is subject to change frequently. Whereas demographic data describes what a company or prospect is, behavioral data describes what it has done. In other words, behavioral data describes events that a company or prospect has triggered.

This is all getting a little complex and MBA-y for the internet, so I want to take a step back and provide an example.

A couple weeks ago someone came to me with a problem. Let’s say his name is John and he sells a product called Circle (a competitor to Square). Well, John’s problem is that 99% of the time he emails or calls a small business they tell him they are happy with their point of sale solution.

In his pitch, John tells them, “Square is great, but if you are a chef who runs his/her own business, you need Circle. We’ve built it for a very specific use case.”

99% of the time the small business owner responds, “I’m not a chef, and I already have Square.” Even the best salesperson in the world would have a hard time convincing these prospects to switch. John lost the game before he ever stepped up to bat. He has 99 problems, and they are all data.

I spoke with John for about 30 minutes and asked him some questions about his business. We determined that his ideal prospect is not only a “chef who runs his/her own business,” but a chef who has just opened up a restaurant. These are prime prospects because they haven’t purchased a point of sales system yet.

When we determined this, he had an idea, “Everyone that opens a restaurant is listed in state business registries. What if we prospected those?”

That’ll do! Opening a restaurant is a perfect example of behavioral data (a prospect has done something that we can call an event)

“And Yelp descriptions generally say whether it’s chef-owned. We could search there.”

Perfect! Rather than just call everyone that opens a restaurant we could do some research to see if they would even benefit from Circle. Remember, he’s built his product for a very specific niche, and it’s important we try to reach that niche.

“Oh and there are chef magazines that talk about recently opened restaurants.”

Now we’re talking! Not only would this prospect be a perfect fit, we’d even have a reason to reach out.

In just 30 minutes, John and I were able to go from Spray and Pray, to targeted outreach. As an entrepreneur this makes all the difference. John doesn’t have time to call and email 99 people in order to find a single prospect. He also doesn’t want to feel like a cold calling telemarketer. Pairing behavioral data with demographic data makes him a targeted sniper rather than a heavy machine gunman.


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Alright, back to the good stuff!

How to apply this strategy to your business:

Redo your ideal customer profile
If you aren’t using demographic and behavioral data to define an ideal customer profile, do me a favor and print your buyer personas out. Then walk from the printer to the window. Create a paper airplane out of the paper and send it as far away from your building as possible. It’s time to rethink ideal customer profiles.

The world of spraying and praying, interrupting innocent family dinners with cold calls, and selling to people who don’t want your product are over. The internet has enabled a new era of sales outreach. Rather than pick up a phone book, or a list from, and start dialing, the entrepreneur or saleshacker would be wise to target his or her outreach. Remember, we want to be a sniper, not a heavy machine gunman.

Go and find out what your equivalent of John’s list of recently opened restaurants is. Maybe it’s surfing LinkedIn for VPs of Marketing who recently joined a company. Maybe it’s Crunchbase’s list of recently funded companies. But I guarantee your ideal customer is not simply mid-size businesses in California.

Build an account/prospect list
Use a combination of demographic data and behavioral data to actually find a list of your ideal customers. This may take some creativity. Ask questions like “Where are my customers hanging out online?” LinkedIn can be a great source of demographic data. But finding behavioral data usually requires going a step further.

If your ideal customer uses a certain technology, try checking out BuiltWith or Datanyze. If they publish news events or PR releases are your trigger, consider signing up for Google Alerts or Mention. Look into state business registries.

I spoke with an entrepreneur recently who wanted to target property managers with elevator maintenance contracts. Elevators have to be inspected yearly by the city which they reside. So he files an Information Act request for $15 and gets a CD of all elevators that need inspection. Every request yields him a highly targeted list with 3,000 leads for $15. Not bad, huh?

Write targeted messaging and hybrid personalize
Get creative in the way you reach out to prospects. Don’t write them an essay. Keep it short, sweet, and personal. Tell them why you are reaching out to them. Then tell them what you offer (in two sentences or less). And finally, make a direct ask (e.g. “Do you have time for a phone call on Tuesday?”) But take it a step further and make use of your new ideal customer profile. Mention the behavioral event in your email. When John reaches out to chefs he writes this:


If all goes according to plan, Carl will respond, “John, great timing. That time works. See you soon.”

Consider using hybrid mail merge tools like, Outreach, PersistIQ or Cadence to speed up this workflow.

Test, test, test

Email 250–500 prospects and then review the data. Use your mail merge tool to track positive response rate and optimize for that. Change your subject line if the open rate is low. Change your ask if the response rate is low. And be religious about tracking the data. If you think tracking data is too much work or too difficult, start out simple!

Set a goal of testing one new profile every month. This is enough time to run prospects through an entire outreach cadence and then review the results. Test new messages to the same profile, and then the same message to different profiles.

After you’ve used behavioral data to crush your sales goals, give me a shout! I would love to hear how it goes :) 

This post was originally published on the blog. If you're a startup, check out their CRM! 

How to Validate Demand for Your Product

Before you launch a company it’s essential that you check if there is demand for your product. Doing so can save you weeks or months of lost time. In this article I’ll show you how to use tools like Google Keyword Planner, Twitter search, and Reddit to validate demand. 


A couple nights ago my friend and I decided to launch a company. We got the urge that many entrepreneurs will be familiar with, and took the leap. 

What set this night apart from the countless other nights of creative ideas was simple: we acted. By the end of the night we had a live website. 24 hours later we had a functioning “product.” This “move fast, and break things” attitude is one of the most valuable assets any successful entrepreneur has. But even the fastest moving of founders should do a bit of planning before spending weeks or months building a company. One of the most important pieces of the planning process is “Demand validation.”

What is demand validation?
First things first, before you ever build a website, product, or start building a brand, it’s essential to determine whether or not there is any demand for what you intend to build. My mentor Alberto likes to say, “Make sure you’re building the right it, before you build it.”

How to test for demand before starting your company
One of the best ways to test demand for a product is to see if people are searching for your product. My friend and I wanted to build an ETF for the cannabis industry (basically an easier way for people to invest in cannabis). 

The first thing I did was use Google’s Keyword Planner tool to look at a couple key metrics: 

  1. How many people are searching for cannabis investing?
  2. How competitive are the keywords in that industry? 
  3. How much do ads cost for each search? 

The first thing I did was open up Keyword Planner and entered a few search terms


Immediately I saw that there were people searching for this. On about 5 search terms there appeared to be somewhere between 1,500 and 15,000 people searching. 


These results were promising, but they weren’t very specific. I wanted to know more precisely how many people were interested in cannabis stocks. 

I opened up Ubersuggest to find related search terms and keywords. 


Then I opened up to figure out exactly how many people were searching for those terms.


BEAUTIFUL! Tens of thousands of people search every month for cannabis stocks. 

This page validated that I wasn’t the only person who was thinking about investing in the legal cannabis industry. 

Using I was able to validate another hypothesis which was that more people would be interested in investing as the election drew nearer (since many states were expected to pass new legislation). I was able to validate this by looking at searches by month. 


A quick note on using Google Search to validate demand
It’s important to note that this validation method only works for certain companies. It works for companies that hope to be first movers in a market that already has pent up demand (e.g. cannabis investing). 

It doesn’t work for products in competitive industries. The reason is that search traffic won’t tell you anything new. For example if you want to build a better dishwasher, you don’t need to validate that demand for dishwashers exists. As another example, if you want to start a video conferencing company you don’t need to validate that coworkers want a seamless, easy to use video conferencing app. For an idea like this I refer you to option #2. 

Validating demand by finding pissed customers
Using that same example (and an industry I’m very familiar with), here’s how I’d recommend validating demand in a crowded space. 

First, I’d go on Twitter to look for people complaining about existing products. I’d go to Twitter Search and enter in a term like “video conferencing sucks.” 


From this basic search I’ve validated that there is a pain point. People online are complaining about video conferencing products which implies there is a gap in the market to be filled.

(As a side note, building a video conferencing product that doesn’t suck is no easy feat. I worked at a company in the industry and learned that first hand). 

Going back to my cannabis investing example, here’s how I used Reddit to validate demand. 

First, I went to Reddit Search and entered my search term. In this case I entered “How to invest in marijuana.” 


Next, I picked a thread with lots of upvotes and comments (as this indicates interest). In this example, I found a thread of people talking about how they invested in the industry and people asking for their advice. This was further validation that: 

  1. Demand exists for the product
  2. Problems (mainly, the complexity of investing today) exist that need to be solved

Wrapping it all up
The idea that you should check if people want your hypothetical product before building said product seems obvious. But I can’t tell you how many entrepreneurs make the mistake of building a complex product before ever validating demand. 

In the next article I’ll go over how to set up a Google Adword campaign to further validate demand. In that article we’ll go over:

  1. How to set up a simple Adword campaign 
  2. How to launch a landing page to explain your product to visitors
  3. How to collect and analyze statistically significant data to decide whether or not to build your product or not

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Update: Some people have asked about the ETF. If you're interested, here is the company that we launched. 


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