How and Why I Wrote a Book about Entrepreneurial Habits

HH Final 06

One year ago, I embarked on a journey to interview 50 self employed entrepreneurs about their daily habits. Now, the result of all those hours of research, outreach, and interviews hits the Amazon store (free Oct 12-13!). Here’s why and how I did it.


A Google search for Lifestyle design exposes hundreds of people making livings off the internet and doing whatever they want on a regular basis. You’ll also notice that these people readily share tips, hacks, and resources for you to do the same. The internet is awash in methods that promise to get you self employed.

However, there’s not much content on what your life looks like when you’re self employed. How does one stay healthy, happy, and productive when you can do whatever you want?

This was the question I found myself asking last September, when I lost my job and my girlfriend in the same week. Suddenly I had a lot of time on my hands, and I didn’t know how to apply it constructively. I knew I wasn’t the first person to face that problem, given my enduring passion for online entrepreneurs, but I realized I didn’t know what any of their daily routines looked like. Couple that with a reading of Mason Currey’s wonderful Daily Rituals: How Artists Work, and I had a draft on my hands.

Interviewing self employed entrepreneurs would accomplish 3 things:

  • Answer my original question for me and the world (this content didn’t exist)
  • Provide a pre baked marketing solution (promote to their followings!)
  • Allow me to personally connect with dozens of my personal heroes.

Nobody wants to spend 25 minutes of their life talking to an internet stranger, but if it’s for a project that may increase their stature or following, it’s surprising how accessible people are.

Indeed, you can see this in the proliferation of modern podcasts where people talk to their friends and broadcast the result along with a sponsored message. I didn’t want to go the podcast route for a few reasons:

  • I’m a reader by nature – I take in information better through writing than listening. The best podcasts were the ones I had to listen to again to take down notes, so why add that extra step?
  • I noticed anecdotally (and from interviews) that the only people who listen to podcasts are those with commutes or workouts, and I saw no need to pigeonhole myself as such.

Worst case, readers would skim my book, but at least they would pay attention to it. With a podcast, your audience is far more narrow, commoditized, and requires a higher degree of commitment. Ergo, a book!


With the interview format, my task was not writing an actual novel but getting the attention of many internet famous individuals. This is an invaluable skill – I first learned it during my job hunt last year, and now as a marketer at a startup, you can boil my job down to 3 things: convincing investors, partners, and press to give me attention. Therefore the process of writing the book was intrinsically valuable, not to mention fun – I got to talk to my heroes, and find more!

The beginning was easy – I started with the least famous entrepreneurs, who were a simple friendly cold email away from saying yes. Much of their audience is found through podcast interviews, guest posts and the like, so I was just another half hour Skype interview in their schedule.

I asked them what their daily routine was, how they shaped their workspace and mental processes, tools and information they’d recommend, as well as the single habit they’d most recommend to an aspiring hustler. I also asked them whose habits they’d like to see next, which allowed me to have each interviewee refer me to the next with a warm introduction.

Once I got farther up the pecking order, things got tougher. Many interviewees were authors and creatives who knew they needed to shut out intrusions from strangers like me in order to get work done, and there was nothing I could say to get around that. However, for the top of the chain, I found that many of the answers to my questions were already online, just scattered throughout several locations. So with them, I gathered as much public info about their days as I could, and then used warm introductions or blatant tweets to get their permission to be included. Nobody said no to that!

The trickiest ones were the famous people who didn’t have info online. I ended up asking them to record themselves talking through my questions and sending the resulting voice memo to me to transcribe, which took around 7 minutes and didn’t require scheduling, unlike 25 minute Skype interviews. This worked, but resulting in less detailed profiles.


In retrospect, I could have made this book much more easily, by focusing solely on quick interviews or recorded voice memos, having FancyHands assistants transcribe them, and having Upwork assistants edit and format the thing into a book. With a format like this, there’s no reason to give yourself more work than necessary. But it was a labor of love, so I don’t regret it.

However, I did notice my interest in the project lagging towards the end. By the time I had completed all interviews, I had kind of answered my original question, and all that remained was grunt work and book marketing. I had written the book I wanted to read, and now that I read it, I didn’t care enough to go big on marketing, which is a problem because book marketing is just as big of an undertaking as the book itself.

I decided to use Amazon for the increased visibility and distribution, rather than hosting it on my own site, where few if any people would find it after the launch. I decided to make the book free for the first two days, to make sharing and downloading easier, and to shoot it up the charts. It’s a common practice I learned from two of the interviewees: Taylor Pearson and Scott Britton. We’ll see how it works out.

As for the marketing, interviewees Ryan Holiday and Charlie Hoehn have fantastic guides on that. However, I measure success like Ryan: “Authors should measure success by the assets they’ve accumulated via the platform they’ve built. This means emails collected, partnerships made with influencers in your space, speaking gigs, evergreen content placements on blogs”. I’ve already got partnerships with influencers and evergreen content ready, so all that’s left to do it put it to work. Sales and profit are less important than connections, and with smart promotion, those will come in spades.

What next?

So, what next? I know what a well-structured day looks like, and I’ve mapped the self employed creative space to my satisfaction. However, interviewing smart people to spread their knowledge and create connections is a winning formula – I could see highlighting self employed entrepreneurs who fit into timely themes, like snake people or the sharing economy, or startup founders with actionable tactics. We’ll see.

Anyways, go read my book! You’ll learn about tons of successful habits, discover new self employed entrepreneurs, and be awash in resources to continue the journey.

Why Don’t We Have Friendly Relationship Management Software?

There are literally dozens of services out there that help salespeople maintain and develop relationships with prospects. Salesforce, Yesware, Highrise, the list goes on and on. So called Customer Relationship Management tools are key in order to track, remind, and manage these professional relationships. There’s services that tell me who to follow up with when, relevant personal data, the history of our relationship, and everything I’d ever want to know about our relationship.

Yet in the end, I don’t really care about those relationships. They are means to an end – to get a sale. Meanwhile, my life is full of relationships that I truly do value – my family, friends, acquaintances, and everyone else I interface with willingly. Why aren’t there CRM platforms for people you care about?

Spending Time With Friends Is Still Hard

You might say that’s preposterous – if they were truly people you cared about, you wouldn’t need software to remind you their name and background details. But I disagree.

Ever since college, I’ve been amazed at how few opportunities there are as a young adult to connect with anyone outside of my inner circle. I spend plenty of time with my housemates, girlfriend, family, and friends in the regular meeting groups I attend locally. But outside of existing circles, it’s very hard to get together with people.

First one party has to reach out and ask, which is easy to forget to do when one has dozens of lukewarm contacts they’d like to see. Then you have to schedule them into your calendar just the same as a business contact, which is hard since we’re all busy. Then you have to find a place and time that works for both! There is undoubtedly friction here, since even dear friends will often deteriorate down to nothing more than a Facebook Like every now and then.

And yet these are truly people who I care about and want more of in my life.It’s ridiculous. If there were software that helped reduce that friction, it would greatly improve my quality of life, more than any social network app. Instead of creating secondary interactions with online profiles, it would increase the face to face time with real people.

An FRM Would Be Similar to a CRM

What would this look like? I daresay it’d be almost exactly like existing CRM solutions, but plugged into your Facebook and phone contacts rather than Linkedin and email. It would provide relevant information about people you haven’t talked to recently, and streamline outreach, perhaps even with templates like CRM solutions do. The key would be making things warm and personable rather than robotic and forced. That shouldn’t be difficult, given the wealth of information people already share to their social networks. There’s already bots that can post statuses that sound like you – why not use that power for outreach?

The friendly CRM could even prompt me to connect with friends based off what we share. If we both post about similar topics – thats a chance to reach out. If it’s been a year since some significant event, time to reach out. Have an unscheduled lunch hour? Pick a valued friend you’ve been meaning to see, and drag and drop to quality time.

Maybe it could prompt me to share content I’m already reading with friends who it knows would like it. Did Joe just post about Trump recently? Present me with an autocomplete template to send my thoughts on the piece I’m reading right now to him and spark a reconnection.

Integrate with Yelp and help us remove the friction of finding a conducive nearby place. Integrate with Open Table and take away the friction of a crowded restaurant. Cross reference my other dear friends and source up the people who have the most interests in common to allow me to double dip and host multiple friends at once. The options are endless, the data is already there, and the need is real.

You know when you reach out to a loose contact to ask a favor, and genuinely wish you were just reaching out to be friendly? I hate that feeling, but not enough to actually schedule warm contact with friends. There’s friction, and no reason to reach out today versus any other day.

That’s the gap this software would bridge – reasons to reach out, while streamlining the event itself to be as easy as possible.

Do Entrepreneurs Create Waves or Merely Surf Them?

Image from BillSOPhoto

There’s a 19th century idea called the ‘Great Man’ theory, which claims that history can be explained by the impact of ‘great men’ who used their power in a way that had decisive historical impact. People like Napoleon, Shakespeare, Muhammed, and the like who pushed humanity forward using nothing by their own charisma, wit, and understanding.

The idea has mainly fallen out of favor since World War 2, as critics have noted that such men are products of their society, noting that ‘before he can remake society, his society must make him’. In other words, their personal input was indeed critical, but it was more the result of him being in the right place at the right time than who he was. They weren’t the only one who could bring together the several converging movements into one (so the argument goes), but they happened to be the one who did.

Great Men of Tech

Today, the concept has resurfaced in tech, as men like Steve Jobs and Elon Musk are hailed as unique visionaries who explicitly created our modern reality. The MIT Technology review does a good job of pointing out that government subsidies play a large part in these successes and how the great man myth is harmful, but I don’t think it dispels it entirely. Yes, such men are products of society, and happened to exist at a time when converging technologies allowed them to catapult things forward, but their own agency has some say in the matter.

It’s unlikely Steve Wozniac would have made Apple such a beautifully designed company, for instance, and unlikely that Martin Eberhard alone would have turned Tesla into the dynamo it is today. Without their ‘great men’, these companies would not have been driven to accomplish what was previously thought  impossible or crazy.

Could someone else have pushed them in the same way? Would any visionary, controlling perfectionist have done instead? Perhaps. What, then, are the key personality traits that one would require for a modern, commodified ‘great man’?

It is not their peculiarities. One of the reasons why the theory is harmful is because it deifies the men and puts their eccentricities on pedestals. There’s a sense that if one wishes to be the next Steve Jobs, one must take acid, wear turtlenecks, and only eat fruit.

But these are not what made such people great. It is important to distinguish which personality traits are frivolities, and which were instrumental in their success

There are a few personality traits that will always be helpful – the ability to pattern match across many different topics, a drive towards perfection, and towering ambition all help. But even with all of these, one must have a good deal of luck, and the ability to see where the world is headed.

Luck: The Only Personality Trait That Matters

Some would argue that foresight coupled with luck is the only important trait.

In Shane Snow’s Smartcuts, for instance, he profiles Sonny Moore, an emo band guitarist who got decided to jump genres and start producing electronic dubstep music. He happened to start making EDM right as the genre became massively popular in the US, and now, as Skrillex, he’s one of it’s biggest stars. Snow notes that it was his ability to sense the impending dubstep wave that allowed him to produce the right stuff at the right time and be successful.

Bryan Lim, the founder of, is another person who benefited from the EDM boom. He was the only person selling rave gear stateside when the craze hit, mostly because he was frustrated with dealing with Chinese manufacturers who had month-long delivery times. While he acknowledges that he worked his ass off making the company, he says that his success was mostly luck and good timing.

Is luck and good timing, then, the only personality trait we should maintain? What should an ambitious young person who wishes to make an impact on the world do, if all who come before him were lucky and nothing more?

Passion + Luck > Foresight

I refuse to subscribe to this new ‘Lucky Men’ theory, that people are successful due to their time and place of life and not due to decisions made during it. It should be put down just as the Great Men theory was. Why? I believe the dichotomy here is not that of destiny vs agency but of passion vs opportunity, the same quandary I examined in Does Passion Trump an MBA?.

To be successful, one should not examine the times and find the wave that is likely coming to a head soon. One should not try to predict the next EDM boom. Jumping into a field because it looks promising will lead to failure, no matter how good the numbers look. Instead, one should jump into fields that one is authentically excited about, and use one’s own intelligence to see how it can fit into the times.

Skrillex and Bryan didn’t sense the coming EDM boom and jump ship – they were already passionate about what they were doing, and would have continued doing it regardless of market conditions. They were pursuing passions more than creating businesses. Even Elon and Steve were pursuing passions – Musk didn’t know anything about rockets, but he knew he wanted to, so he dove into all the regular texts on the subject, until he could count himself as an expert. He wasn’t doing that to make money – he did that because he cared about getting to Mars.

Then again, if they had decided to pursue passions in underwater basket weaving, farming, or horseback riding, it’s unlikely they would become ‘great’. Why? These are unscalable passions, that only affect a few people no matter how good you get at them. Integrate one of these with a technology wave coming to a head, however, and you’ve got something big. Run a farm using drones, track horse vitals using wearables, or make a platform that teaches people how to weave, and now we’re talking great.

Here, then, is my vote for the best way to become a ‘great person’, regardless of the times: Turn inward to discover what you re truly passionate about, and master it. Then turn outward, and see how evolving developments in your time and place are affecting your passion. Then put yourself in the right place with the right network to leverage your knowledge of the craft and the times to make a difference.

Find your passion, then get an MBA in the times to maximize your impact. How’s that for a recipe for greatness? (genuinely curious here)

Credibility is A Bad Way to Measure Trust

Surf the internet long enough and you’ll start to notice some patterns. One of the big ones is the press banner. Most websites trying to sell you something put their’s front and center, from personal blogs, to ecommerce stores, to startups.

Look, we were featured on Forbes, the New York Times, CNN, and David Letterman! Obama tweeted us once! Abraham Lincoln was our biggest fan! It’s become such a cliche that StartupLegitimizer will auto-generate a press banner for you, ‘for instant legitimacy’ (see above).

Credibility is Ossified Trust

Why do this? One word – credibility. Press banners, testimonials, name dropping, and any other kind of recognition on the web serve one purpose – convincing you that the personality is credible. You can trust them, because [insert respected name here] trusts them, or at least worked with them once.

Someone toiled for years to make the New York Times a trusted purveyor of quality information, and eventually, it had consistent quality long enough to make the brand itself trustworthy. Therefore, when it features someone, that trust rubs off.

In this case, trust is defined as confidence that they deliver what they promise. In other words, they do what they say they do. They have integrity. An integrous entity is one that is trustable. You don’t care that it was featured in the NYT, you care if it does as advertised, and you trust the NYT to only feature things that do as advertised.

And yet, this trust was transferred from one entity to another, so is it still authentic?

Ossified Trust Isn’t Authentic

It seems that all credibility benchmarks fail to truly capture trust. Press coverage is a terrible way to do it – the news is a hype machine that jumps on anything that elicits a response. Expert endorsements are equally sketchy – just because someone is an expert in X doesn’t mean you can trust them with Y.

It’s kind of like hiring – you don’t really care about qualifications, you care about their skills. You want them to be able to do the job, and the only way to know that short of making them do the job is to look at similar jobs they’ve done in the past. Qualifications don’t fully capture skills – people can look good on paper but terrible in reality, or terrible on paper but great in real life.

Likewise, as a startup marketer I see a lot of ‘vanity metrics’ – numbers that sound good but don’t convey much, like messages sent, total downloads, or (heh) press coverage. The only real number that matters is how many of your users keep coming back – user retention. If they come back day after day, it shows trust. You delivered on your value proposition before, and they trust you to do it again.

The only credibility benchmarks that really work are testimonials from someone who has dealt directly with the person in the way that you plan to deal with them. Banks look for good credit scores since they’re giving you a loan. Landlords look for past landlord references. Consultants look for past clients, to see if the freelancer leaves behind happy customers.

Can We Transfer Trust Without Credibility?

So we know that the only way to establish trust is through transferring it from an existing trust source. Companies do this too – it’s why they pay employees referral bonuses, as it’s easier to extend their trust of the employee’s capability than start from zero on a cold applicant. It why it’s easier to hit on girls at house parties than at bars – in the former you both theoretically trust the host, but in the latter any weirdo can walk into a bar. Even better, get introduced by a friend (that’s how most Americans met their significant other)!

How, then, could we establish trust at first contact without using an existing entity? Is it possible to trust someone immediately, without credibility indicators?

Anecdotally, it would appear so, given the existence of ‘love at first sight’ and ‘it just seemed right’ stories you hear all over. Personally, I decided to share a room with a guy who I has only spent about 40 minutes with beforehand, and everything is great for us, 8 months later. Somehow my intuition was right on that one, but what is it reading?

Trust Yourself, Over Other Sources

My guess: it’s reading integrity, just like in the professional sense. Professionally, your product/service does as advertised. Personally, you do what you’ll say you do. Therefore, to trust a stranger, they would have to act according to your principles.

You could sense their principles in a thousand little ways. The way they carry themselves, the clothes they wear, the people they associate with, what they talk about. If any of that pattern matches to people who you’ve already trusted, then it’s likely you can trust this person too.

In a way, we’re back where we started, because now we are pattern matching strangers to existing sources of trust, rather than transferring it directly. What’s the difference between me trusting a guy because Tony Robbins approves of him, vs me trusting him because he reminds me of Tony Robbins? Not much, except now it’s me making the call, rather than Tony. And I know my own sense of trust better than I know Tonys.

If nothing else, this allows us to value our own trust over outside source, which is a good thing. Rather than placing our faith in false idols, we place it in ourselves, and evaluate each new entity on its own merits. In this way, credibility is circumvented, directly back to trust. It’s not perfect, but it’s better than a press banner.

You just have to have a better bullshit detector than the New York Times. Isn’t that something we should all be striving for?

What Is A ‘True Self’ and Can You Trust It?

Continuing on my hippy fascination, one concept I encounter often with such people is that of the true self. It may also be called the ‘wisest self’, ‘authentic self’, or just your heart, but the meaning is the same – it’s the only part of you that it truly you, untainted by the influence of society, others, and even your own second thoughts. The argument goes that listening to this alone is the sole path toward true fulfillment.

If they’re right, that’s the most elegant way to solve the Be and Do dichotomy yet. An inner part of you that directs you to do things without any thought whatsoever? Then I could embrace my true self, and Be myself so authentically that anything I Do would be in tune.

Isn’t ‘True Self’ Just Intuition?

There’s a lot of voices in my head, and they don’t all say the same thing. There’s Freud’s Id and Superego, of course, but perhaps his ego is something like the ‘true self’. And there is scientific backing to the idea that your intuition is something worth trusting (Malcolm Gladwell’s Blink, among others). Sounds like it boils down to trusting my gut, then.

However, my intuition has limited knowledge and is shaped by past experiences. Why should I trust an amateur like myself with a new and critical decision? I feel it would be foolhardy not to research the options and educate myself using the knowledge of experts and others who have gone before me

Here’s where it gets tricky. True Selfers would say that it depends on the person. Some people may immediately feel that one decision is better than the other, why others (like me) would want to research first. In my case, it’s my true self telling me to research first, and so doing that would be the best option for me, but not for all.

This sounds a lot like destiny, that old philosophical hack saying everything is predetermined and we have no free will. Heck, one of the smartest guys I know (Sam Harris, Stanford neurobiologist) believes that. Anything my true self tells me to do is the right thing for me to do, by definition? That strips me of all agency, making me a puppet who follows the strings of my true self wherever it goes.

No sane person would agree to do whatever someone else said, no matter what. But that’s the trick – the true self by definition is you, even more so than what you conceive you to be. It knows everything you do, has your best interests at heart, and makes decisions unconstrained by the opinions of others. You take care of all the rational thought and agonizing for it, leaving it (in theory) to make the best possible decision in a snap. I’d be an idiot to not listen to it, if that’s the case. I would be able to fulfill all my business goals by just being myself, since that’s what I am drawn to do.

Example: My ‘True Self’ in Action At Networking Events

I can’t deny that the concept of ‘relaxing into yourself’ has proven quite helpful to me recently, especially at networking events. These are normally quite goal-oriented affairs, much more businessman than hippy. How, then, does the true self fit in here?

Well, my true self loves networking events, no matter what anybody else tells me. Therefore it makes sense to attend. Who should I talk to? This is the biggest worry a networker has – opportunity cost. What if I spend my time talking to losers and not the power brokers at this event? What if someone else cuts a business deal at my expense? Is this conversational partner worth my time, or is there another out there who I should be talking with instead?

Of course, I safeguard against this through preparation – dressing remarkably, researching attendees beforehand, and strategically attending certain relevant meetups. This sure doesn’t sound like relaxing, but it’s what the authentic Corey would do, which also happens to be the best way to find good people.

The difference is that now I don’t worry. I trust my true self to have done everything it could to set the stage for success, and enjoy myself while at the event. I talk to people I want to talk to. I trust my intuition to decide who is worth talking to. If someone isn’t interesting, I politely say it was nice talking, and move on. If I get hungry or tired, I’ll eat or take a break. I do whatever feels comfortable and right, rather than trying to squeeze in as many contacts as possible. If I miss a power broker, so what? I did my best, and if they’re truly relevant, we’ll cross paths again somewhere else.

That’s what my ‘true self’ tells me to do. I trust myself to maximize the opportunity, because that’s what I do. Only a year ago, it would not have been possible for me to relax, only strive and plan. I suppose the argument would be that my true self back then was the one telling me to get better at networking, and now it has changed its tune.

Sigh – it all sounds so fatalistic. I cannot escape my true self – only embrace it! What if embracing it doesn’t bring me closer to my goals? Well, then, true selfers might say those were not the right goals for you after all. The true self, the only one you are comfortable with, will be perfect for you, but may seem ridiculous to others. Who cares? They don’t know the real you.

Are Hermit Mystics Being True to Themselves?

So, if your true self doesn’t care about what others think. What if someone’s authentic self gave no heed to society at all, never washing, growing everything out, and living in the dirt with no money? Sounds a lot like most gurus and mystics, no? Here we are back to the problem of Elle Luna, just more extreme. Such people follow their own paths to fulfillment, but in doing so, they stop contributing to the world of others (unless they teach). Surely the true self would be generous and caring towards others, and value the fulfillment of others as well?

There are very few people raised in Western democracies that end up like that, which makes me believe that your true self will probably not lead there unless you are born in the Himalayas. What does that say about the effect of culture on your wisest self, to which it is supposedly immune? Westerners say the ascetic monk was warped by his surroundings and is not 100% authentic, while Easterners say the same about our successful business titans. Does a true self vary across cultures?

I don’t know, but I know that my true self would never tell me to go into hermit mystic mode, so I’m not worried. And my true self tells me not to worry about the paths of others, since they have their own decisions to make, and I do not know what is best for them. All I can do is continue asking questions, and recognize that I will never have all the answers.

How do you feel about the concept of a ‘true self’? Is it New Age hogwash or is there something there?