The 10 Most Influential Books I Read in 2014

In 2014, I made it a goal to re-dedicate myself to reading. I read a ton growing up but for the past 6-8 years, I probably read less than 10 books per year outside of class. The books I recommend below were all personally transformative for me in one way or another. As with any book, the influence the books below had on me was based on a combination of things including what was going on in my own personal and professional life as well as what was happening in the world at the time.

This is not a ranking list so the books are presented in no particular order.

Zen and The Art of Motorcycle Maintenance by Robert Pirsig

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I really, really wish I had read this book before starting my undergrad degree in engineering. Throughout college, I felt frustrated about the theoretical focus of engineering education. I fall more on the visual learner side of the spectrum so learning about chemical engineering was particularly difficult (it’s hard to picture molecular interactions). The times I felt most comfortable were when a previously discussed concept was physically shown in a lab class. As my friends from college are very much aware of, I was pretty outspoken about my frustration with the curriculum and the way engineering was being taught.

This book dives right into the engineering education issue and so much more. It’s told in a narrative format about a father-son, cross-country motorcycle journey that’s filled with flashbacks and self-discovery, but most importantly, goes into the philosophy of the relationship between art, science, and practical application. I have to credit this book for finally “connecting the dots” for me between the classroom engineering concepts I learned at CMU and the real world around me.

The War of Art by Steven Pressfield

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This was a quick but very influential read. Anyone who has tried to build, write, or create anything will appreciate Pressfield’s book, which basically boils down to how to recognize and conquer The Resistance, something we’ve all felt when doing something necessary but difficult.

Creative Confidence: Unleashing the Creative Potential Within Us All by Tom and David Kelley

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There aren’t many people more creative than the Kelley brothers, who helped found and lead IDEO, the world’s leading design consultancy. The biggest takeaway for me was that creativity is something we all possess. Some of us just lose confidence in our creativity while growing up. Perhaps we were told we can’t draw or that we were analytical or that we were athletes and so stopped exploring our “creative side”. I read this in tandem with Zen and the Art of Motorcycle Maintenance and found the two to be very much related. This book is the reason I decided to take my first acting class and then helped me find the confidence to think I could be decent at it.

The Alchemist by Paulo Coelho

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Can’t believe I didn’t read this book until this year. If you’ve had moments of doubt about your life’s direction (whether personal or professional), this book will literally feel as if it’s written for you. Read it.

Side note about Paulo Coelho: some people get put off by the religious (Christian) nature of his writing. Whether you consider yourself religious or not (I’m personally not religious at all), his writing is still inspirational and provides guidance with the existential questions of life.

What’s Mine Is Yours by Rachel Bostrom

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I’ve gotten really interested in the sharing economy this year (also known as the 1099 economy or the Uber economy) and this was the best book I found about the young industry. The book was written in 2010 (before the whole Uber craze really took off) so it’s amazing that so many of the predictions in here are spot on. Bostrom’s analysis and thinking around the whole space are great in terms of giving you a complete picture into the trends and forces causing “on-demand” and “sharing” services to explode in popularity today. The coolest takeaway from her analysis of the sharing economy: it’s really a move away from the unnatural “largeness” of 20th century corporations and a return to the more local economies of the past (and hopefully future).

If you’re interested in the sharing economy, you HAVE to read this book.

If On A Winter’s Night A Traveler by Italo Calvino

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Hands down the most creative book I read all year and possibly in my entire life. The book has 10 “first chapters” of stories intertwined with a love story involving…you! It sounds bizarre but it’s so engaging and I wasn’t able to put it down once I started.

The book was originally written in Italian (Italo Calvino was Italian, in case you couldn’t guess that from his name) and reading this really made me wonder what, if anything, was lost in translation. The English version is so great, I can’t even imagine how good the original was.

Zero To One by Peter Thiel

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Whether or not you’ve read the Blake Masters class notes from Thiel’s Stanford class, this is an interesting and important read. Regardless of if you agree with his politics, there are few people out there like Thiel and his contrarian thinking definitely gets you thinking outside the box. I personally don’t agree with 100% of his views but his thinking is presented in a readable, accessible manner that had (and still has) me looking at the world with a renewed desire to solve big, meaningful problems

Incerto Series by Nassim Nicholas Taleb

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Taleb is a genius, plain and simple. I wrote about his work earlier this year and his writing has been hugely influential in crystallizing my thoughts on risk. Just as importantly, his work is hilariously written and somehow manages to make 3 books about a “boring” topic like risk impossible to put down.

While I chose to feature The Black Swan, the other 2 books in the series are Fooled by Randomness and Antifragile. They can be read in any order but I would recommend starting with The Black Swan, then moving to Antifragile (my favorite in the series) and then finishing with Fooled by Randomness if you’re still interested.

Warning about Taleb: He’s EXTREMELY opinionated, which leads to some amazing and entertaining writing but can also piss some people off. If you read his books and end up falling into the pissed off group…can’t say I didn’t warn you.

World War Z by Max Brooks

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Directly related to Taleb’s work is World War Z. The zombie infection outbreak is a great, thankfully fictional, example of a Black Swan event. I also happened to read this around the time of the ebola breakout so that probably played a part in making this so memorable for me.

I was a huge fan of the movie too but the book is very different. The movie was told from one person’s point of view while the book is basically a series of recollections from various points in time during the outbreak and war, with no central character.

The Meditations by Marcus Aurelius and Letters from a Stoic by Seneca

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This year I got interested in learning more about Stoic philosophy. I’ve never been one to “sweat the small stuff” so Stoicism made intuitive sense from the beginning. The coolest thing to me was reading Meditations and literally seeing a Roman emperor struggle with the same things I do on a daily basis – namely, knowing that the world isn’t perfect and adapting my attitude to make sense of and operate in that world. Learning about Stoicism also played a big part in helping me come up with my morning routine.

 

So those were the top recommendations from my 2014 reading. If any of these books look interesting to you, definitely make the time to read them. Also, if you have a Goodreads account, let’s connect there.

I’m always on the lookout for more to read so definitely send your recommendations my way!

 

When Free Stuff Online Becomes Dangerous

Ask anyone if they want to get something valuable without giving up a single penny in return and they will definitely say “yes”. It’s a human trait – we really love free stuff.

On the Internet, we’ve gotten used to getting products and tools for free. There’s nothing inherently wrong with this. Some companies are using a freemium model where they give away part of their product for free to entice you to buy the full product. Game companies do this all the time as do companies like Dropbox. Other companies give away their product for free in an effort to build an audience and sell ads – Google, Facebook, and Twitter for example. Although the ads can get annoying sometimes, these are all perfectly acceptable business models.

Where things get more dangerous and scary is when tools that involve sensitive information, such as healthcare, personal finance, or security are given out completely free. I want to be clear here: I’m not talking about freemium or free updates. I’m talking about 100%, no strings attached, free.

Why is this dangerous? Because companies need to make money and the easiest way for these “free” products to do it is by selling your personal data. In its most innocent form, this simply involves lead generation – think Mint.com and all the credit card offers you receive through their site after making an account. At a more insidious level, personally identifying or user activity data could be sold to third parties.

Don’t believe me? StopDataMining.Me was featured in Lifehacker last year identifying 50 data brokers who store and re-sell your personal data to others. They all have ways to opt-out but let’s be honest: how many of us even know the names of all the companies reselling our data? Even worse, you have to opt-out from each site, one by one. The problem is so widespread that The Federal Trade Commission issued a report earlier this year recommending that Congress require data brokers be more transparent and give consumers greater control over their personal information. Not much has happened with that so far but the recommendation by the FTC is a step in the right direction.

At the individual level, there’s not much we can do about all this except be aware of it. I’m not saying we should stop using free tools. Just be sure to think through the business model of whatever tool you’re deciding to use. My one recommendation would be to opt for paid tools and services for things that involve sensitive data – the extra few dollars per month is worth it.

How Are Some People So Productive?

The thing that impresses me the most about successful people is the sheer volume and quality of their work. How can someone accomplish so much in the same 24 hour days that you and I have?

Who are some of these people I’m so impressed with? Well how about Ryan Holiday, who was simultaneously Marketing Director at American Apparel, blogging extensively, and writing high quality books. Or James Altucher, who has started multiple successful companies, ran a hedge fund, spilled his soul on his personal blog, wrote several of books, runs a very successful podcast, and is also an angel investor. Or my good friend Justin Mares, who simultaneously scaled Airbrake as Director of Revenue (which led to an acquisition by Rackspace) and co-wrote Traction (which I highly recommend by the way). People like Ryan, James, and Justin inspire me.

I try not to even think about the productivity required by Elon Musk, who is CEO of both Tesla Motors and SpaceX. He’s Iron Man though so I guess he doesn’t count.

So how are these people so productive? Here is what I’ve observed:

  1. Routine: Productive people have a routine that they use to get themselves in the zone. I’ll be writing a lot more about this in the future as it’s a personal interest of mine but for now let’s just say that getting “in the zone” is not random.
  2. Time Management: By this I don’t mean OCD behavior like scheduling every second of your day including bathroom breaks. I’m talking about avoiding the endless Facebook/Twitter/Yahoo/YouTube/Quora/Buzzfeed time waste loops. They seem like short breaks but end up taking 15-20 minutes each time and eat up huge chunks of your day.
  3. Inspired: Productive people simply don’t hate their work. In fact, it’s usually the opposite – they actually enjoy working on their craft.
  4. Student Mentality: All these people have a certain humility about them and in spite of their success, maintain a humble student attitude. They are always learning and more importantly are always open to learning.
  5. Gratitude: it seems counterintuitive but productivity requires being in a healthy state of mind, which means being thankful for your life while still striving for improvement. I’ve seen people I admire consistently practicing gratitude and adding gratitude to my morning routine earlier this year was the best thing I’ve ever done for my mental health.

Here’s some simple math: if someone has just 1 more hour of productivity per day than the average person, at the end of the year, they’ll have 365 hours of extra work. After 10 years, that’s 3650 extra hours. Over a 30 year career, they have a 10,950 hour advantage. According to Malcolm Gladwell’s book Outliers, 10,000 hours of practice is the key to mastery so based on the math, someone with an extra hour per day will be a master of 1 more skill than the average person. If that skill is something valuable – you can see why that makes a difference. I would make the argument that highly productive individuals actually have a 4-5 hour per day advantage over the average person, which would mean mastery of an additional skill happens in 6-8 years instead of 30. While I’m not a huge fan of Gladwell’s work and disagree on a few things, the conclusion is the same: the extra hours compound into a real advantage over time.

This is one of my favorite topics to learn more about so if you’ve observed any other techniques or use something yourself, definitely let me know in the comments or contact me directly.

The One Thing They Don’t Tell You About Growth Marketing

True or False: Accomplishing your goal 30% of the time is good.

The answer: It depends. If you’re in school and only getting 30% of the answers correct, it’s probably time to stop reading this post and go hit the books. But if you’re a baseball player and have a batting average of 0.300, then you’re one of the better players.

Growth marketing, especially for startups, is more similar to baseball than it is to school. You’ll try tons of different tactics and strategies to grow – the phrase we use is “Throw s**t against the wall” – and most of it won’t improve your growth rate at all. Of the few things that do work, most of them won’t be scalable and allow you to grow 10X. Finding a scalable growth tactic that works is a bit like trying to find a needle in a haystack, except in this case, you don’t even know if there is a needle hidden in the haystack.

So if most things don’t work, how do you find the things that do? By doing lots of customer development and experimentation, which requires a completely different mentality than schoolwork. This was the most difficult leap for me – realizing that my answers were going to be wrong more often than they were right – and being OK with that. It’s hard to overstate the difficulty of this mental switch. We go to school for 12 years and then years of college and/or grad school with the “I should always get the right answer” mentality, which is counterproductive to being a good growth marketer.

The best way I found to handle this leap is to think like a scientist. I start with a theory, for example a new pricing strategy, and then develop an experiment and hypothesis to test that theory in the real world. Testing can only be done by putting your idea in front of customers/users. I try to pick a big enough sample size to make the experiment relevant (sample size depends on what you’re doing/selling) but keep it small enough to where I can speak with the customers individually to learn why they are saying yes or no. Unfortunately, thinking like a scientist is not taught in high school or undergrad, even if you major in science or engineering. It’s something you have to develop on your own.

The last piece of advice I’ll give on this is that successful growth requires thinking outside the box to find something that clicks (terrible pun…). At Mom Trusted, we experimented with phone, direct mail, email, fax, social marketing, SEM, SEO, conferences, and many many more tactics (with lots of iterations in each of those categories) in order to find the channels that worked. Other companies, like Eat24, have gone even more outside the box by advertising on overlooked web properties (including porn sites). All of these tactics were figured out through data-informed (not data driven) experimentation.

Thinking about growth marketing like a scientist is a skill and like any skill, it can be developed through practice and study, with practice being more useful than study. If growth is something you’re interested in, I strongly recommend getting real world experience as soon as possible.

 

Deep Knowledge

It’s so easy these days to think you’re an expert at something. Read a few articles about a topic, look at a few Quora questions, maybe watch a YouTube video – and bingo, you’re an “expert”. Unfortunately, even though knowledge is more accessible today than ever before in human history, deep knowledge still takes the same amount of time and effort as it did before.

Maybe the reason I’m thinking about this today is that I made the mistake of watching the news for a few minutes this morning (blame my parents – they had it on). With election day coming up, they were trotting out source after source – all of whom had mostly no idea what they were talking about. For example, they brought out Richard Branson to explain the Virgin Galactic crash. Sorry, Richard Branson may be the head of Virgin but he’s not an engineer – he doesn’t understand what went wrong. Sure he can regurgitate talking points but that’s about it. The worst part is that people are going to watch that interview and walk away feeling like they’re “experts” on what went wrong – and share that opinion with others. You’ll see the same thing if you watch MSNBC/Fox News/CNN and listen to someone talking about any topic – healthcare, jobs, the economy, etc.

Reading a few Wikipedia articles is certainly better than knowing nothing about a subject but it doesn’t replace true learning. That’s why I recommend books over any other learning source (except real world experience of course). The knowledge necessary to write a great book about one topic requires such deep subject matter mastery – it just doesn’t compare to any other communication medium. The only exception I’ve seen to this rule are bloggers who write just as deeply as great authors. The only difference is they distribute their content for free on the Internet in short chunks (aka blog posts).

Deep knowledge takes time, effort, and experience, which is why I don’t consider myself an “expert” in anything yet. With some luck, maybe I’ll be close in 10 years.

Staying Mentally Stable On The Startup Rollercoaster

Lately, there’s been some much needed talk in the startup community about the mental health effects of the constant ups and downs that come with being involved in early stage companies. The toll can be especially taxing on founders – take a look at the notes Brad Feld received from founders after he wrote his illuminating “Founder Suicides” blog post earlier this month.

The media usually portrays famous founders as Supermen/Superwomen – which makes “regular” founders feel inferior and inadequate. This is very much related to the “crushing it” culture that has gotten so rampant. When founders are asked how things are going, it’s incredibly rare to hear an answer other than one of the many variations of “crushing it”. With more people like Brad Feld talking about mental health, I’m hoping that honesty will become more common, but maybe that’s wishful thinking.

Having been involved in a couple startups over the past few years, I’ve been through some awesome experiences and also through shitty, terrible things that I wouldn’t wish on my worst enemy. Staying mentally healthy in a rollercoaster environment like that is a huge challenge and to be honest, is something I’ve struggled with at various times in my life. Over the past few months, I’ve taken a more active approach to keeping a healthy mindset. Below are some scientifically untested techniques I’ve been using with success so far to keep my work problems in perspective:

 

Read Books:

I read a lot of books growing up but for some reason I pretty much stopped once I got to college. In 2014, I rediscovered my love for reading and it’s been great. Most importantly, I’ve found it’s a perfect escape for my overactive work brain. When I watch TV or a movie, my brain doesn’t have to do any work and continues drifting towards work. When I’m reading a book, my imagination gets involved and my brain stops thinking about work for awhile.

Stay Physically Healthy/Exercise/Go Outside:

When you’re already not in a great mental state and then something goes wrong physically, you’re just asking for disaster. Re-committing to my health after some issues in early 2014 has helped my mental game so much.

Going out into nature is really helpful to me as well. There’s something about being in nature that just gives perspective and makes problems feel insignificant.

Get a Hobby:

Doing something outside of work gives you two things:

  1. Your brain gets a break from thinking about the same problems – which actually helps you solve them.
  2. You make friends outside the startup bubble

I started taking acting lessons in April and it’s been great. I’ve met people who live in a completely different universe from the startup community, which is enlightening. It’s also given me insight on my own emotions and habits that I wasn’t previously aware of. I started this hobby so randomly: I took a four week Acting for Non-Actors class to improve my sales skills and ended up liking it so much that I started training more seriously. Most importantly, it lets me shut off the analytical part of my brain for awhile and do something different.

Stay Close With Your Family and Friends:

This is listed last but it’s by far the most important one for me. In most industries (including startup world), things work like this: when things are going well, you have a ton of people contacting you and it feels like you’re the most popular person ever. But when things are going badly, no one wants to talk and you feel like an outcast.

The good news is that relationships with your true friends and family don’t change when things are going great or when things are going terribly. They will be there for you. This is why it’s so important to not let your relationships die out of laziness or lack of time – something that happens too often. Friends and family are your mental safety net. When I’m having a crappy day, nothing cheers me up more than gchatting/texting/Snapchatting with friends or having a long phone conversation with my mom, dad, and brother. Invest time in your relationships and you’ll never feel alone.

 

Lastly, I just want to say that having struggled with some of these issues myself in the past, I’m always here if someone needs to talk or get things off their chest.

 

Disruption Is Counter-Intuitive

Question: Pre-Uber, how many startups were trying to disrupt the transportation industry?

Answer: No clue but way fewer than there are right now. Transportation was always viewed as an old school, unwieldy, high investment dollar industry that only fools invested in. The closest we came to transportation disruption was Zipcar and even that seemed like an uphill battle the entire time. However, they paved the way for Uber to come in and fully disrupt transportation and potentially other industries as well.

Today, with Uber being valued at greater than $15 billion, transportation is viewed as a “hot” industry and startups are popping up all over the place.

Never mind that everyone has known taxis were awful since the first time they ever rode in one. It was always just one of those things we lived with:

“Oh man, I gotta carry enough cash for the cab”

“It’s impossible to get a cab in this city” (not in NYC or Chicago but everywhere else)

“I hope this cab takes credit card”

Most of us probably thought, “well this is the way taxis are and have always been”. It’s only in hindsight that the disruption seems so obvious and inevitable.

I can’t see the future but here are some “old school” industries that may be ripe for disruption in the next few years:

Government Services

Arguably, Uber fits in this category since part of the reason for their explosive growth has to be because government has done such a terrible job with public transportation services. Think about how low the bar is with bus or subway service. I’m happy with my BART trip as long as there aren’t any bodily fluids on the seat I’m sitting on.

Parking

Similar to above – how is it that cities have tons of available parking but since they are on private property, no one can park there? That’s lose-lose for both the property owner and the person trying to park. Win-win is so much better and I guarantee one of the parking startups out there (or maybe one that has yet to be created?) will gain mainstream adoption and completely change city parking for the better. As someone who hates (and is terrible at) parallel parking, I hope this happens soon.

Accounting

This one is self-explanatory. Taxes and compliance SUCK for individuals and businesses. Great pain = great opportunity.

 

There’s probably dozens more that aren’t even on my radar because I just think of them as existing and not as industries to disrupt. More likely than not, the next industry to be disrupted won’t come from my list at all. These things usually aren’t logical. And that’s part of the fun.

 

My 5 Minute Morning Routine

I know I’m not the only person who experiences this but I’ve struggled with negative thinking my whole life. I don’t mean that I always expect things to go wrong. It’s more like, when I have too much time to think about things, I get “down”, and when I get down, I get unproductive. When I get unproductive, I get more negative. So it becomes a cycle. And I mostly feel this way early in the morning right when I wake up and late at night right before I go to sleep, which led me to explore and experiment with my morning routine and night routine.

A few weeks ago, I started doing something that, so far at least, has gotten me out of the negativity cycle and allowed me to start my day feeling mentally at peace. I’m not saying this will work for everyone but it’s been working for me. I do the following things within the first 10 minutes of waking up:

Step 1: I write down what I am most grateful for that morning. I try to be completely honest with myself on this. If I’m honestly most grateful that I’m about to drink a cup of coffee, I write that down. If I’m grateful that a big project is over, I write that down. The key is being honest with myself. One thing I’ve noticed is that as time goes on, I’m more grateful for my problems – which sounds ridiculous! Sometimes things that seem like problems are actually blessings. I was recently struggling between a few different career moves and was really stressed out about the decision until one day it just hit me that I’m so incredibly fortunate to even have 1 opportunity, let alone several.

Step 2: I write down one thing that I want to accomplish that day. This is a lot different than a to-do list. I make sure I limit it to just one thing. We all usually have so many competing priorities that our brains can only process that there’s a ton of “stuff” to get done today. Unfortunately for most of us, there’s more “stuff” out there than we can ever do in 24 hours so we need to prioritize. Writing just one thing forces me to really figure out what my top priority is for the day.

Two steps seems too good to be true but I’m not arguing with the results so far! I may add things or tweak this morning routine as time goes on but for now, I’m planning to stick with it.

 

Human Hubris and the Big Data Fallacy

I recently finished reading both The Black Swan and Antifragile by Nassim Taleb and find myself constantly thinking of the “Turkey Problem”. For those unfamiliar with Taleb’s work, the Turkey Problem relates to the fallacy of thinking that past results indicate future trends.

Taleb uses a turkey being raised for Thanksgiving as an illustration. The turkey is being fed and taken care of every day of its life from birth until the day it dies. A human is feeding the turkey, providing it with shelter, and protecting it from the harshness of the real world (predators, weather, etc). After the first X number of days, the turkey starts to truly believe that the world is a place where humans constantly help it improve it’s well-being. By extrapolating to the future, the turkey predicts (perhaps using Big Data techniques?) that this state of affairs will go on forever. Unfortunately for the turkey, on day 1001, the day before Thanksgiving, the plump turkey is killed and is used as the centerpiece for your Thanksgiving meal. Yum!

If the turkey were using modern statistical models, this event would’ve come as a complete shock. Extrapolation is dangerous territory but what makes this situation even worse is that the turkey is in the most danger exactly when the model says he’s safest! (after 1000 days of data)

 

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Being in the SF Bay Area, naturally my thoughts drifted to the rise of “Big Data” and how it is being used in almost every industry now to “optimize” and make predictions about the future. In markets where there are physical constraints and well understood rules on things (bounds, defined odds, etc), there is definitely value to having a model and using it as a predictor. For example, a casino can model the behavior of gamblers to optimize profits. Fine. No problem with that.

Where things get tricky is when people take complex systems that are not well understood and try to build models on top of that. Don’t get me wrong, there is nothing wrong with having models and using them to try to create a picture of the universe in some controlled manner. Where these models get dangerous is when people use them exclusively to drive company policy or worse, government policy to force people into their contrived version of “reality”. Prime examples of dangerous models include anything health, climate, or economy related.

In case you think the turkey example is only limited to poultry, remember that after every major global event in our lives, the people in charge said that “this couldn’t have been predicted”. They’re right. Everything from 9/11 to the 2008 economic meltdown to Fukishima, every major event that has shaped the present has been a surprise that went beyond anything that was modeled.

There’s a reason for this. A model simply cannot predict something that hasn’t happened before if it is only using past events as a basis for future events.

And to finish this post off, here’s a prediction by Nobel Prize winning economist Paul Krugman made in 1998 about the future of the Internet:

“The growth of the Internet will slow drastically, as the flaw in “Metcalfe’s law”–which states that the number of potential connections in a network is proportional to the square of the number of participants–becomes apparent: most people have nothing to say to each other! By 2005 or so, it will become clear that the Internet’s impact on the economy has been no greater than the fax machine’s” (emphasis mine)

With a track record like that, you’d think people would stop listening to the forecasters. Unfortunately, that’s not the case. Paul Krugman is still out there, making predictions and writing his weekly column in the New York Times. That’s human hubris right there.

 

Don’t Get It Twisted: Customer Development = Startup Sales

There seems to be a misconception out there in startup world. There is plenty of talk about “customer development” and Lean Startup Methodology (talking to and learning from potential customers) in the product development stage, which is great. But there is simultaneously a sense of apprehension when it comes to “monetizing”, as if it’s this mythical, frightening beast. I’ll let you in on a secret: customer development and early stage startup sales are literally the same process.

This comes back to a fundamental misunderstanding of what selling is. Way more than any slick sales pitch, it’s about matching your offering with a customer’s need. To create this match between product and need, you need to listen but you also need to expose yourself to failure by trying to sell and seeing what happens. The biggest mistake you can make is giving the impression that your product is free when it actually isn’t.

And once you do bring up price, always be ready to close the deal! Most people separate customer development from sales so that they are either only:

1) Learning during customer development conversations

2) Trying to sell while in sales calls with potential customers and not trying to learn anything

Yesware’s founder Matthew Bellows offers a warning of this exact symptom in one of his early blog posts where a potential customer was ready to buy licenses for their sales team but he was too busy thinking of potential features to notice the buyer’s intentions. Yesware has raised double digit millions and is absolutely crushing it (I love using horrible cliches) so if they can make a mistake like this, it’s very possible that you can too.

But what happens if you misread the potential customer’s intentions, try to sell them, and they reject you? You’ll hit an objection. Objections are great because you learn why the customer is saying no! If it’s something wrong with your product, you can now go fix that problem. If it’s related to your pricing, you can work on that. The real problems come when you aren’t getting any feedback on why the customer isn’t buying – it’s impossible to fix the problem when you don’t know what the problem is in the first place.

There’s another hidden advantage to having paying customers – it’s way easier to get useful feedback. At one of my previous companies, we went down the free trial route and got solid adoption from one of the core audience groups (high school counselors). The problem? They never used the product unless we told them to. We weren’t sure if it was because of our design, our product, or if we just weren’t solving a true need. You’ll never have this problem if you’re asking initial users to pay money to use your product – they’ll either not buy your product or they’ll quickly cancel if you aren’t solving their need.

Don’t overcomplicate things. If you’re doing customer development already, just add a step and try to close the sale. Worst case, you’ll learn more and if all goes well, you’ll have some revenue. And if you’re not already doing customer development and you run a startup, the time to start was yesterday 🙂