Look at all those books that somebody wrote
Look at all those books that somebody wrote

...when you have to write your ideas out in complete sentences and complete paragraphs, it forces a deeper clarity of thinking. – Jeff Bezos

(This post is a celebration of completing our first full book, SelfMadeU! You can get it at Amazon.)

I was working with Mark Medoff, an Oscar-nominated, and Tony Award-winning writer, on his most recent play and asked him for writing advice.

He said, “I can tell you everything you need to know about writing in  thirty seconds.”

He told me what Kurt Vonnegut told him, “There are three parts to everything, the question, the exclamation, and the conclusion.”

“Other than that, nobody has any idea what they’re doing.”

He teaches a class on writing so I’m sure he was being facetious. Sort of.

People ask me how to write all the time thinking there is an answer beyond, “write”. The fact is, most of us just need permission to start writing. Every great writer will tell you that you’ve got to just keep writing.

Once you begin writing we’ll add the technical stuff one write.

This post is broken down into nine sections:

  1. Why Your Business Needs You To Write Well
  2. Why You Need To Write For You
  3. How To Be A Better Writer
  4. How To Write Better
  5. Technical Tips
  6. Tips For Kickass Sales Copy
  7. How To Keep Writing
  8. Recommended Reading
  9. How To Begin NOW

Your business needs you to write. You need you to write. We need you to write.

Connection is all that matters now. We’re all disillusioned with lame marketing tactics. We know the dirty secrets of those yelling about “Make $3000 TODAY From Your Computer! No Effort Required!” – they’re full of shit. We know there are good guys out there, but who?

How do we (the Good Guys!) show that we’re trustworthy? How do we connect to other humans on a level that corporations and phonies can’t?

We need to be honest and then learn to communicate that honesty in the most effective way possible.

Arm yourself.


Why Your Business Needs You To Write Well

Whether you work for yourself or somebody else, you’re going to be better off if you can write (read communicate) effectively. You’ll also just be better. At everything. Like making money and making business.

Speech conquers thought, but writing commands it. – Walter Benjamin

  • Communication. There is not a single person on the planet that doesn’t use written communication every day. If you are hiring a virtual assistant, you need to be able to give them crystal-clear instructions. If you’re trying to get a client, it helps to be comfortable using your words to get them on board. If you can’t word a status update well then you’re going to have a tough time engaging anybody. Think about all the ways you write to people every day: texting, tweeting, status updates, blogging, email, bathroom graffiti, writing AdSense Ads, deciding on what tattoo you want.
  • Everyone is a media company now. Content marketing is huge and blowing up even more in 2013. More stuff is being put out there and Google is learning how to get rid of the crap. Writing well is probably your greatest SEO strategy. Videos, podcasts, and images are a boon here as well but writing remains king. Without stellar content nobody will care about you. Nobody will find you. And you need to be found. Get generous – get great at writing.
  • Sales. Nothing sells you or your business like beautifully placed words. If you can’t describe your product to somebody in an emotionally powerful way, you can forget about selling it.
  • Investors. Entrepreneurs must be effective communicators. This isn’t an “extra”, if you can’t clearly describe what you want an investor to invest in… well, just go home.
Jeff Bezos made Amazon and thinks writing makes you better at thinking
Jeff Bezos made Amazon and thinks writing makes you better at thinking
  • Strategize. If you can’t clearly put a business strategy into words, how is anyone going to follow it? How will you follow it? How will you know if it even makes any sense? Writing will help you think about your business goals and how to get there. Amazon’s Bazos
  • Solve problems. Entrepreneurs are basically independent problem solvers. We see an opportunity in a problem that people are having and then create something to solve it. This takes a lot of thinking and wading through a lot of bad ideas. Writing is one of the best ways you can see whether your solution actually makes sense. It’s like the pre-test to the validation test.

Why You Need To Write For You

I told you about how writing saved my life once. It hasn’t stopped since. If I go a week without writing I will become scattered and stressed. Overwhelm takes hold, new ideas stop coming in, and I find myself reading too much garbage (or finding myself on page 17 of reddit). Even if you don’t believe me that writing is necessary for business, you’ve got to try it out for your own life at large.

hemingway bleed
  • It’s for your business. Your business is your source of finance and fulfillment. That should be reason enough to learn to write well.
  • Overcome Overwhelm. There are always too many projects going on, too many problems to solve, too many thoughts to remember, too many things in general. Writing puts the mess of thoughts onto paper or computer. Once a week (or more) I write down all my projects and everything that needs to get done for each. When I do this it becomes easy to focus on the task at hand. If I don’t do this I’m constantly anxious about whether or not I’m spending my time on the right thing. Do yourself a favor and get everything you need to do on one sheet of paper.
  • It’s free therapy. Writing your stream of conscious is worth more to me than a therapist. We’ll talk more about the details of this later but for now, believe me. If you’ve been looking for a way to reduce anxiety, depression, or just generally “get your life together” this is your holy grail – and it’s free. It’s a beautiful thing to learn about yourself in this way.
  • Externalizes ideas. Your brain is constantly full of ideas and it gets clogged if you don’t empty it out. You need to put the ideas that have been swimming around in your head on paper and make new for the fresh ones.
  • Build subconscious associations. When you write about something you will find that your brain immediately starts making connections. You start to pull in other ideas and mix them up with your current ones. You start to have certain types of ideas. If you spend a week writing about ways you could make your business better then your brain will start feeding you those ideas.
  • You notice those quiet ideas. When you write the ideas that your subconscious brain feeds you then you are showing respect for those ideas. Carry a notebook to record these and you’ll begin to find them coming to you all the time.
  • Measured thinking time. We all know that we should spend more time thinking, but it’s difficult to just sit down and think about something. When you sit down and write for thirty minutes you know that you spent thirty minutes thinking about something.
  • You will learn more. When you write you are forced to recognize what you understand and what you don’t. If you want to learn a skill, begin writing about it. Find your knowledge gaps and then fill them – then write to find some more!
  • You connect to people you wouldn’t have otherwise. Writing honestly has connected me with tons of new friends that I wouldn’t have made otherwise. When you put your ideas in front of people and connect with them, you’ll be amazed at the people you meet. So many of us are just grateful for somebody to say something that nobody else will. We need your perspective to help explain our own.
  • Learning. When you write about something you discover what you actually know. It’s the same idea as teaching something to understand it more thoroughly. This is almost always less than you think. When you’re thoughts get organized into sentences and paragraphs then you realize the missing parts. Now you know what you need to go and find.
  • You see your soul. There is something about creating that lets you sneak a peek at that magical thing artists, philosophers, and saints talk about. Writing is especially interesting for this because you have words to remember the moment by. This sounds weird, I know, just try it.
Jack Kerouac bled, too.
Jack Kerouac bled, too.

How Be A Better Writer

In order to write you need to be a writer. Which means you need to give yourself permission to write. The following are ways to get your mind into writer-mode.

  • Stream of conscious. If you take one thing from reading this, make it this. Writing my stream of consciousness has been one of the coolest ways to understand my current situation in life. Set a time for 20 minutes (or an hour…) and just start typing. Or writing, pen and paper is even better. The rule is that you have to keep moving your fingers. You’re not allowed to pause to think or anything else. If you get stuck then just keep writing “I don’t know what to write” or “My brain is empty” or whatever else comes out of your finger. After a while you will just say “screw it” and find the good stuff. I promise you you couldn’t use your time better than this. (This is also great for people who have been meaning to meditate but can’t bring themselves to. You end up with similar results.)

Write freely and as rapidly as possible and throw the whole thing on paper. Never correct or rewrite until the whole thing is down. Rewrite in process is usually found to be an excuse for not going on. It also interferes with flow and rhythm which can only come from a kind of unconscious association with the material. – John Steinbeck

  • Know you will write mostly terrible things. You don’t get to start making things and immediately be really good. Become a freelance writer! After a ton of practice your writing gets better on average, but you’ll still have terrible days. Yesterday was miserable. I couldn’t type anything worthwhile. Today is different (well… it feels different). Don’t let this stop you. Just like working out or gaining a skill – you don’t just start out genius at it.
  • Be passionate. If you don’t care what you’re writing about then don’t be surprised when we don’t care about it. If you have no excitement for what you’re writing then you won’t be able to make it interesting.
  • Write it like you won’t show it to anyone. Always remember that the first draft is for you. You never need to show another person what you’re doing. You may end up deciding to share it but always write knowing that you can keep it private. This makes it more candid. It’s easier to be brutally honest when you know you don’t need to show it to anyone.
  • Write to somebody. If you can pretend like you’re writing to your best friend then you’ll be helped immensely. It will be easier for your voice to come through and it will feel more conversational. You’ll be connected to the person you’re communicating with – even if it’s a stranger. For instance, I’m aiming this at a couple friends of mine who are beginning to write but need some assistance.

Forget your generalized audience. In the first place, the nameless, faceless audience will scare you to death and in the second place, unlike the theater, it doesn’t exist. In writing, your audience is one single reader. I have found that sometimes it helps to pick out one person—a real person you know, or an imagined person and write to that one. – John Steinbeck

  • You know enough. People think they need to have something epically important to say before they begin writing. You don’t. You already know enough right now to write a book, I promise you that. Humans care less about information than they think; a lot of times we just need human connection or a reminder. If you don’t get good at writing now, what will happen when that epic idea comes along and you have to tell people about it? Nothing. You won’t understand how to communicate it effectively.
  • Be strong. Don’t apologize or “guess” about your opinions. We know it’s your opinion, you’re writing it! Own the damn thing. Don’t give us disclaimers or anything else that makes it harder to care about what you’re saying.  You have an opinion – tell us!
  • Be relatable. Some authors think they have found every answer to the Universe. Is it fun to read an arrogant author? Nope. We’re all humans here. We have problems and have failed and cried and all the rest. You’re a human, act like it.
  • Be conversational. Well, conversational like when you’re conversing well. You want the reader to be able to read your work quickly and easily.
  • Find solitude. At least for your own head. I love the solitude of being in a coffee shop with head phones. It’s impossible to write while somebody wants to talk to you. It’s impossible to write if you’re more interested in doing something besides writing. Sometimes it’s best to be by yourself. Sometimes coffee shops are the best. Find your spots and use them.
  • Caffeinate. If you are blocked, it’s because you haven’t had coffee. Caffeine let’s words flow like nothing else. Somehow a cup of coffee makes that thought important enough to write down.  
  • Embarrass yourself. If you have something written and you feel completely comfortable hitting “Publish” then re-read what you wrote. Is their any power in it? Is the information great? Is there a way you can make it more relatable?
  • Never stop writing. When I go a day without writing, I’m guaranteed to write something bad the next day. When I go a week without writing it takes several days of crap before I get anything decent. Write every day. Even if it’s just for yourself. Put pen to paper or fingers to keyboard.

When you can’t create you can work. – Henry Miller

  • Never stop writing: Part II. Everything that happens in your life is fodder for writing now. Use everyday life to make connections. Can you connect a football game with your article on SEO? Can you use that interesting fact your friend just let loose in a novel? When you begin writing, you’ll notice yourself getting excited to pull things that happen in life into your writing. Take a notebook with you and make notes to remember them.
  • Bleed or bore. I can’t say this enough. If you’re not going to be honest with us, we won’t care. If you hide yourself in your writing then we won’t read it.

Don’t ever write a novel unless it hurts like a hot turd coming out. – Charles Bukowski

  • Be funny. If you can make someone laugh then you win.
  • Read a ton. Read every day. You need to make good writing an input to make good writing an output. Read in your area of expertise and outside of it. If you want to be any good at all you have to read great writers. That means if you’re a business blogger you should be reading some great fiction. I find it extremely helpful to read immediately before I write as well.
  • Become a wordsmith. Learn to love words. Use words as your tool to creating something beautiful. Don’t be afraid to make words up. Sometimes the word we need doesn’t yet exist – make it!
  • Have fun! If you’re miserable we’re going to know it and we won’t have any fun at all. And, damnit!, we want to have fun! Words are easier to put down when you’re in a playful attitude. You take yourself less seriously and therefore are fine with the imperfect sentences you’re throwing out.

Don’t be nervous. Work calmly, joyously, recklessly on whatever is in hand. – Henry Miller 

  • Steal. Take good ideas unapologetically and make them your own. Don’t plagiarize, go deeper than that. Take an idea so completely that you can’t help but make it your own.

Immature poets imitate; mature poets steal. – T.S. Eliot

  • Do research. Bring information into your writing and watch it become more powerful. Data shows us that you can’t be lying (we don’t believe that statistics would do such a thing). It also gives you interesting details to write from.
  • Be brave. If you won’t say the thing that’s scary to say then you’re no different from the rest. You selfishly hold back the one thing that we could connect with. Don’t. Be free. Don’t be afraid to type something you don’t mean – you don’t have to show it to anyone else if you don’t want to.
Don't be a pussy - SAY IT!
Don’t be a pussy – SAY IT! (image from www.brainpickings.org)

Technical Tips

Let’s get down and dirty. The above list is all about your posture. Lean into your writing and let everything loose. It’s about getting to the keyboard or

  • Be brief. The quicker you can get an idea through the better. This usually happens in the editing. You have to keep deleting things until everything that is left belongs. George Bernard Shaw said it best in a letter to a friend, “I’m sorry this letter is so long, I didn’t have time to make it shorter.”
  • Use little words. It’s not impressive to use words that you wouldn’t use in everyday conversation. It just sounds contrived. Get your idea through in the most effective way possible. Your vocabulary will naturally expand as you read and write more.
  • Make lists. In order to get a post going, I will write down as many ideas about the topic as possible. I have about thirty unused ideas for this post. Just keep writing down ideas that may fit into whatever you’re writing.
  • Make an outline. This isn’t necessary all the time. It’s helpful for longer pieces, though. It’s nice to have a bit of a roadmap to keep you on target. Sometimes you can get lost in your own writing and need to come up for air. An outline can help reorient you by giving you a wider perspective.
  • Alliteration. It’s pleasant to read two words with the same beginning sounds for some reason. I don’t know why. Inject some poetry into your prose.
  • Rhyme. This is also pleasant. Studies have shown that rhyming makes something more convincing. Don’t overdo it. Unless you’re trying to be Dr. Seuss – then let loose.
  • Use pictures. If you’re a blogger then don’t forget to use images. Pictures have also been found to be persuasive.
  • Short sentences work better. Just give us one idea per sentence. Sometimes we want to say everything right now in this exact sentence. Don’t. Take your time. Make it easy and enjoyable for us to read your ideas.
  • Clarity is key. Without clarity you have nothing. No communication. Focus on that and everything else will come (voice, style, rhythm). Einstein said, “Everything should be as simple as possible, but not simpler.” And, by golly, Einstein is always right. Except for when people smash particles together and find black holes and say that theory of relativity might not matter anymore (or something).

No time for poetry but exactly what is – Jack Kerouac

  • Don’t use jargon. Don’t use words we wouldn’t know, it’s rarely impressing and never relatable. Focus on who you’re trying to get your message to. Use words they use.
  • Clichés don’t work. We skip over them like they never happened. Same thing with faddy words. Don’t try to be hip’n’hoppin’n’happen’n (see what I mean?). It’s more fun to write when you come up with your own weird expressions anyway.
  • Be active! Never say, “This is the company built by me.” when you can say, “I built this company.” We love verbs! Give us movement!
  • Kill “very”. The worst way to emphasize a word is to put “very” before it. “I am very cold” isn’t nearly as effective as “I’m freezing.” Same thing with “quite”, “really”, and the rest of those stupid things. (And while we’re here, it’s perfectly fine to put a comma before “and” when listing things.)

I believe the road to hell is paved with adverbs, and I will shout it from the rooftops. – Stephen King

  • Fewer prepositions please. It’s tiring to read sentences with too many prepositions. Focus on keeping your sentences active and you’ll be safe.
  • Get to the point. Nobody is as interested in your buildup as you are. This is especially important for you if you’re writing to educate. You have one sentence and a headline to make me care.
  • 3 Parts. We know movies are broken into three acts (or you do now) but we forget to use this magic number in our own writing. Everything should be broken down into three acts: the story, the chapter, the paragraph, and sometimes even the sentence. We start with a question (?) then get into some trouble (!) and end with an explanation (.).
  • You’re telling a story. Treat all of your writing like a story. Even in education. If you’re throwing information at me I won’t be able to care about it (i.e. learn) unless you’re entertaining me to. Tell a story to make us care.
  • Show me. Express what you’re trying to explain in your writing style. This will come naturally after writing for a while. It’s good to keep in mind.
  • Leave things out. If you’re too detailed then our imaginations have nothing to do. We are bored by stories that tell us too much. Your whole story is too long, anyway. Give us just the right details.
  • Metaphors! Metaphors are webs in the mind different from those that most people are operating with. Start connecting!

By far the greatest thing is to be a master of metaphor. It is one thing that cannot be learned from others. It is a sign of genius, for a good metaphor implies an intuitive perception of similar among dissimilars. – Aristotle

  • Read it out loud. When you read your words out loud you will see whether they flow naturally. It will become easy to spot uncomfortable areas that need fixing. It’s uncomfortable to do but it will make your writing much better instantly.
  • Focus. Write a one sentence summary of what you’re writing. Let that keep you focused when you forget why you’re sitting in front of a keyboard. My sentence for this article is, “A writing resource that will be helpful enough to be bookmarked.” Am I doing it? Let me know what you think in the comments!
  • Put statements in the positive. Never hesitate in your writing. Make us feel you’re committed. “The ice cream man wasn’t often on time.” can be turned into “The ice cream man was usually late.” We find what is much more interesting than what is not. Instead of “not good” say “bad”. Instead of “did not remember” say “forgot”.
  • Express similar ideas in similar ways. This is a specific example of structure helping you express what you’re saying. In a list, this would sound weak: “I love to comment, share, and to Like.” It’s stronger to make it: “I love to comment, to share, and to Like.” Or even, “I love to comment, share, and Like.” Expressing similar ideas using similar form makes them more powerful.
  • Keep the tenses the same. Don’t send us to the past and then throw us into the future and then assume we’ll know when you’re talking about the present. It’s not fair. When telling a story that happened in the past, be sure to let us know when we’re back in the present.

Tips For Kickass Sales Copy

I avoided learning about sales copy for a long time. We don’t want to admit that we have something to sell; it feels dirty. We’re all selling all the time though. We want people to agree with our ideas on politics, religion, or the nature of reality. We want to convince people that Tyrian is, in fact, the most fascinating character in Game of Thrones. And, once in a while, we want somebody to give us money for something. That’s the only way we get to eat.

  • Create scarcity. We are frightened to miss out. What if they get the information and we get left out? It’s creating the FOMO (fear of missing out) for your product or service.
  • Repeat things. We need to hear things over and over again for them to sink in. The massively popular blog ZenHabits repeats many ideas over and over again and we love Leo for it. He says it in new ways that make lessons sink in. So repeat yourself to hammer home the ideas that you really want to hit.
  • Ridiculous guarantees. Eliminate all the risk from their purchase. Give a free trial, offer a 120% refund, or tell them they can keep the product at no cost if they don’t like it. Again, make not buying your product the absurd choice. Make this a major focus in your offer.
  • Social proof. Show clearly that everyone else is doing it. Of course they are, you’d have to be dumb as hell not to jump on a deal like this!
  • You’re special. Make them feel special that you’re even offering your services to them at all. It’s an exclusive club and they better feel grateful to be involved. Or make them feel like they could be one of the few chosen ones.
  • Paint a picture. Help them imagine their whole new life or business or whatever that they will get once they give you what you want. You’ve got to make them want the result of your offer.
  • Appeal to their ego. The vast majority of our purchasing decisions are based on ego. This holds true for business purchases. We want to make people feel great about purchasing our products (or, if you’re a jerk, terrible for not purchasing them).
  • Show credibility. We only trust the people who’ve proven themselves. Make your case obvious through past achievements, current endeavors, or deep understanding. We’ve got to feel safe paying you.

How to Keep Writing


Writing is one of those things (like meditation, exercise, eating well) that’s easy to stop after you’ve seen the benefits from it. You begin to take your health for granted and so you start eating donuts again. You forget that the reason you’ve found that health is because of the practices you had! Here is how I keep my words coming:

 Abandon the idea that you are ever going to finish. Lose track of the 400 pages and write just one page for each day, it helps. Then when it gets finished, you are always surprised. – John Seinbeck

  1. Daily stream of consciousness. This is where I externalize everything that needs to be externalized for the day. Often I’ll find new ideas for a blog post or business in the stream. You can find more detailed rules in the How To Have Ideas post but for now remember that you have to keep your pen or fingers moving for the whole time. When you have nothing to say then type, “I have nothing to say.” Set your timer for twenty minutes and write whatever is in your head.
  2. Small goals. Don’t plan on writing 1000 words a day right off. Definitely don’t plan on showing people the first things your write. Set yourself an incredibly low minimum (like 200 words) and meet it every day. Consistency is the key here.
  3. Carry a notebook. Having a notebook serves as a place to put your ideas and a reminder that you have ideas. I recently forgot to carry my notebook with me for a week and had precisely 63% fewer ideas. When you write an idea down you show respect to the act of having ideas. Another way to increase the amount of ideas is to buy a decent notebook – the monetary investment is also a sign of respect. My idea-maker loves these shows of respect and pays me back with a whole lot of ideas.
  4. Read. It’s much easier to stay inspired to write when you read good books. After a while without reading I tend to dry up in the idea or style department.

If you don’t have time to read, you don’t have the time (or the tools) to write. Simple as that. – Stephen King 

Recommended Reading

what she's reading...
what she’s reading…
  • Bird by Bird was the first book I ever read on writing and it gave me permission to write badly – something you have to do if you have any hope of writing well. I’ve given this book to multiple blocked authors and it immediately opened them back up to writing again. There are plenty of great life lessons for anybody sticking their neck out (read: entrepreneurs) and trying something hard.
  • On Writing is Stephen King’s memoir of writing. It’s written in a straightforward style that is amazingly powerful. Anybody who recounts stories from their own life in writing will especially find the book helpful.
  • Elements of Style is on pretty much every great author’s “must read” list. It’s impressively short and will give you a solid foundation to write from. It gives you strong rules to follow without infringing on your expression at all.
  • The Spoke Zarathustra is Friedrich Nietzsche’s masterpiece. It combines poetry and prose in a way that is beautiful and brutally potent. Reading this book informed my own writing in a massive ways when I began. Nietzsche’s excitement for ideas is intense and contagious. (You can also insert your favorite fiction novel here – one that you appreciate for it’s writing.)
  • Dr. Seuss and writers like him (Shel Silverstein comes to mind) show us how clear you can be using the simplest words out there. See how powerful humor and rhyme and rhythm is in making a point.
  • Anything that interests you. Reading is dull when you’re reading something because you feel you should. When something is dull we don’t learn from it. Follow your interests, even if they’re not where you think they should be. There is often more business wisdom in biographies than business books.

How to Begin NOW!

I urge you to do begin right now. If you don’t start now then you won’t ever start. I can pretty much promise you that. You don’t have time? Take five minutes.


  1. Open up your text editor (Text Editor or Notepad is fine).
  2. Click your cursor inside.
  3. Set your timer for 15 minutes.
  4. Turn your monitor off (or screen brightness all the way down).
  5. Start typing.
  6. Don’t stop moving your fingers for 15 minutes.
  7. Write, “I have no idea” if you don’t have any ideas.
  8. Repeat 7 until you give up on having no ideas and write down your idea.

This will force you to see that you can write, that you have ideas, and give you forward momentum with any other writing you’re doing.

For Potential Bloggers

We all need blogs now. You probably know this but haven’t been acting on it. Do this planning exercise to get your brain going.

  1. Write down five potential blogs you could make.
  2. Pick one.
  3. Write down thirty possible blog posts you could make for that.
  4. Write one short blog post.

This should take you about an hour and you will have started a blog. Maybe you won’t want to continue with it. Maybe you’ll want to spend your time talking about something else. You can’t help but learning a lot from this.

 For Potential Book Authors

You can write that book that you’ve been thinking about. Stop telling people abou the thing you want to do and take the first step towards creating it. You can finish a book amazingly quickly if you commit to 500 words a day. That would take you about 20-30 minutes a day.

  1. Write the mission of your book. This is a one or two sentence summary of what you want to do. 
  2. Create an outline. This won’t be final but it’ll create a guiding structure for your thoughts.
  3. Commit to a certain amount of words that you’ll write every day. Maybe you just want to do 200 words every day. Some days you might do more but you need to do at least X words every day. (There are no roll-over words!)
  4. Meet your quota today.

You will finish your book amazingly fast if you do this. Consistency is key.

Take this moment to put your dent in the universe and WRITE
Take this moment to put your dent in the universe and WRITE

Comment below and let us know what you’re writing!

Are you trying to write a book but can’t quite start? Blog?

Let me know what’s holding you back from starting or where you’re getting stuck.


Avatar for Kyle Eschenroeder
Kyle Eschenroeder

Thanks for taking the time to read this! Let me know what you think - the good, the bad, the ugly - in the comments below.

I'm an entrepreneur (more in the StartupBros About Page) in St. Petersburg, FL

40 comments add your comment

  1. Kyle,

    This is ‘God Send.’ Lots of inspirational ideas. No time like the present, so I’ve taken the ‘plunge.’ 30 minutes each day set aside to write….starting now!

    ‘Procrastination Is The Enemy Of Success.’ Now, that is a good title for a best seller….

    Keep the good information flowing…


  2. Excellent tips mate I’ve just tried writing anything in a notebook for 30 mins, and it wasn’t all complete rubbish!

  3. I love this! Its my dream to have my book! Been trying to start on writing since college. Will save this! Definitely big help! Thanks!

  4. Hi Kyle, thank you… I was researching about business plans and suddenly found you!
    I feel extremely inspired by your words on the “massive guide” to writing, it was all I needed today.
    This encouraged me to start something different now without fear. I will definitely give writing a try, in fact, I will start as soon as I post this comment.
    Please continue writing, your tips and advices are so refreshing, I feel like someone deep cleaned my brain. Everything seems clearer now.
    Wish me luck!

    • So glad you found this useful Vanessa! I can’t wait to see what you do! Hope to see you back here soon!

  5. I have a theory/technique that is very rare and whenever I share it people are blown away and encourage me write a book. Some friend are outright angry with me for not pursuing this as its been almost 5 years that I have been sitting on this.

    You asked what is holding me back?

    1. I suck at writing, I’m so envious of people who can express their thoughts and articulate so well. The masterpieces in my mind never translate on paper.

    2. I wouldn’t want anyone to know I wrote the book. If it actually did well I wouldn’t want to be known and the person that wrote it. If I could publish is anonymously or with a fake alias I would be much more inclined to start. I don’t think anyone would be interested in reading a book who’s author doesn’t want to admit writing.

    • Hey Dan,

      I’d love to see your book, email it to me at kyle at startupbros dot com if you’d like!

      All unedited writing sucks. Nobody starts great.

      You’re problems are amazingly common (but FEEL uncommon)… if you could bring the courage to share you could inspire others.

  6. Sounds a lot like advice from James Altucher but you definitely made it your own. Really great post. I’ve been teetering on the edge of being consistent with my writing but I think this is the thing that will topple me over and make it a daily practice.

    Thank you.

    – Steve

    • Hell yes for the Daily Practice 😉
      James has been one of the major influences in my writing in the past couple years so I’m sure there are going to be overlaps. Good ideas need to spread, no matter where they come from!

  7. Great information Kyle! I’ve had blogs and books on my mind for a long time and this helps me to get the ball rolling in the right direction. I have not background or experience but this gives some great advice to changing that! Thanks for the tips!

    • Absolutely! I’m looking to do more on writing so email me with any questions you have! Kyle at startupbros dot com

      Looking forward to seeing what you write!

  8. Any tips on how to improve writing when having problems with the language? Because my second language is english and proofreading all my texts costs for me (I am still a student) a ton of money.

    • Focus on keeping your communication as simple as possible. This will help you stay clear and avoid as many nuances as possible.

  9. Dude, this is ridiculously valuable. The “ultimate guide” actually does this post justice…

    • D’AWWW! Thanks Mansal! That means a lot coming from a mean blogger like you.

  10. Ya I need to figure what I can “bleed” about. Maybe I need to read more blogs to get an idea.

    • No way, Eric!
      Do the stream-of-consciousness writing but do it for a full hour. Just once. Do it instead of meditation tomorrow.
      Do it promising that you won’t show it to anybody. Then write as fast as you can and don’t look at your screen. You won’t be able to help but bleed.

      I guarantee you: an hour of that is worth four hours of reading blogs idea-wise.

    • See Kyle that’s what’s cool about you is that you talk about these taboo things of blogging. I’ve only read blogs in the financial community, and I am working to expand. Anyways, I know for a fact that some of those bloggers put on a show, and don’t actually believe the stuff they write. And then there are martial arts teachers that talk about budo, but do it just to sell belts.

      Gosh, I guess I should write about that kind of stuff. I think i’m doing the streaming stuff you’re talking about. So if I write just freely. There might be a lot of profanity. My blog will be shut down. hahaha.

      Thanks…I’ll try the streaming conscious writing.

      • Eric, I consider my blog to be MY place and voice. Even if nobody reads your / my material, it helps you to internalize the message so that it stays relevant for your own life. It’s almost like accountable journaling in a way. You are accountable to anyone who does read it, but you are journaling your thoughts and feelings.

        As far as bleeding is concerned, it is all about your comfort level. Do you feel comfortable writing about things in your life? Would you feel comfortable showing your friends and family? If the answers are “yes”, then you are bleeding and more power to you.

        • Mans, I’m confused. Kyle was telling me that the most uncomfortable things to post are your best works.

          • This is really interesting! It comes down to the individual. My best stuff comes when I go to another place in my life/brain that I haven’t discussed publicly before. It’s scary (uncomfortable) to get naked in front of people in a new way. I NEVER get into somebody else’s personal life. This isn’t because of comfort level but because I don’t have the right to share their details.

            Bleeding doesn’t mean you need to expose your life but it does mean you need to expose yourself. Seth Godin is a perfect example of someone who rarely talks about his life (never his family) yet has exposed himself completely. His soul is so tied up in his writing that we can feel the vulnerability.


            Think about bleeding. It’s effortless. When you have a cut then blood just flows out. THAT’S the important part. Just let the words flow as though they were blood. That means being okay with writing bad words and letting yourself go back and edit them later. It means you might not hit publish on that post. It also means that you have little control over what you’re writing. You don’t censor anything until the edit.

            A couple other visuals… and these get kind of gross. Puking and shitting. When I really didn’t like my writing I had to use those as visuals for what I was doing. I don’t expect anything out of shit, I’m definitely not going to show it to anybody. But it flows and it has to come out.

            Mans, could you describe your journaling idea more? For me, I have to keep a journal that’s separate. I even have to keep a blog that’s separate from StartupBros. When I’m here I have a certain duty to talk about things within a realm. It’s not fair for me to use this place as too much of an exploration of ideas. StartupBros is for presenting battle-tested ideas to people who care. My journal is to externalize the things you won’t care about. Nah’wut’ay’mean?

          • Kyle, I dont see how one can expose themselves without exposing their life, family and the people around you? That is what life is!

          • If you wrap your soul into a certain idea tightly enough and ask people to listen you’ll find yourself exposed. Think of a poet or artist who’s soul is on the line yet you know nothing about his life. I agree though, it’s much easier and usually more effective to use your own actual experiences to connect.

            Does that make sense?

  11. Thank you. I just started today with a stream of consciousness writing on my tumblr blog about all the things I want to be doing with my life.

    • So awesome! Feel free to share it if you’d like us to read it! See you back here soon 🙂

  12. This was a phenomenal post. A lot of the reasons you mentioned here for not writing are my excuses daily after a long 8 hours of programming. I go home and a beer + videogames sounds so much better than writing.

    But, not today.

    Your tips on writing for yourself and writing TO someone were phenomenal. Pretend no one will ever read it, and keep writing. I’ve been browsing /r/writing for some time now, and this post caused me to reply not only on reddit for the first time but on here as well for how well done I think it is.

    • Awesome! I hope you come back and share something you write. One of the most freeing things to me was when I realized that I could write honestly about my experience and that would be enough. There doesn’t need to be a spark, sometimes a quiet honest observation is all we need.

      • I’d be VERY pleased to share. Gotta lot because I’m probably twice your age! Always been a rebel though… once the computer firm I worked for in the 80’s gave my superior a promotion for MY idea, and me the shaft… I decided I would always be an entrepreneur. And here we are.

        Though I’m not a young feller like you and Will, I want to speak to that audience. There’s no reason that bright young people have to go through the heartache of having their talents misused and abused. Not when they can experience the freedom, lifestyle and rewards that are available to true entrepreneurs.

        Lemme know if there’s a current topic that would serve your audience. If I know something about it, I’ll give you the old guy perspective 😉

        Keep Stepping,


  13. Kyle, this is perhaps the best post I have ever read on the subject of writing, not just for business but for any reason.

    Writing my goals and articulating my plans helped me start a martial arts studio at age eighteen. It helped me design curriculums for young people… that have grown up, had kids of their own and brought me NEW Students. And writing helped me get through a painful divorce.

    I have written an information product that has sold over a million dollars worth of copies. If I had read this post of yours ten years ago it would have been done in half the time and been twice as good of a read.

    I would ask to guest blog for StartupBros but DANG. Not sure if I’m up to the standard… and I’m twice your age and education.

    Thanks again for this post.

    • Thanks Kurt! That means a ton! Really glad to have you as a part of the community here. And your writing is great! I’d love to see your information product – where can I find it?

      • Kyle, Matt Dixon, I apologize. I subscribed to this comment thread and thought that Kyle’s reply to Matt was intended for me. OOOPS. Sorry about that.

        Regarding your actual reply to my comment. Thanks Matt! Means a lot. My info product is available at radioactivetrading(dot)com and is called The Blueprint. I wrote it in 2002 to show folks how not to get hurt trading the stock and options markets. Seems like you and Will might need it soon, with all the big bucks you’ll be raking in from your “biznesses”.

        The Blueprint is rather pricey. Shoot me an email at the Shoestring101 address and I’ll forward you a PDF copy of my earlier work. I think you will dig it.

        Keep Stepping,


        • Awesome! Looking forward to seeing what you’ve got! Sent you an early version of an upcoming product as well 🙂

  14. I’m a writer-turned-entrepreneur, so it’s nice to see that this skill can be so useful in business.

    To add to your tips on kickass sales copy, I’d say to pay attention to headlines on magazines when you’re standing in the checkout line at a store. Cosmopolitan is one of the best in the game.

    Take a good headline: “3 Secrets to Finding Out If He Really Wants You Tonight”

    Turn it into a formula: “[number] secrets to finding out if [person] really wants [something] [time period]”

    Let’s say you run a website that gives advice to aspiring rock bands who want to break into the music business.

    Apply it to your niche: “3 Secrets to Finding Out If a Record Producer Really Wants to Give You a Deal Now.”

    It’s a useful method for learning copywriting from the pros.

    • That’s a great idea! Thanks for sharing! A lot of writers are being pushed into entrepreneurship – it’s the only way now!

  15. First off, congrats on the book!

    Second, lots of good tips. I saved the post to refer to later. I found myself agreeing with a lot of the things you mention in the “Why You Need To Write For You” section. A lot of those reasons are frankly why I write.

    Also, in the Kickass Sales Copy section did you mean to put “You’re special.” bullet in there twice?

    • Thanks William! Hope to see you back here soon. Looking forward to your learning book! I hope you write it regardless of the campaign.

      Didn’t mean to have that bullet in there, good catch!

      • Thanks man. Yeah, I will write it regardless of the campaign. Been wanting to write a book for a long time… trying to get past the “wantrepreneur” stage as well..

        • What’s stopping you from writing it right now?
          What’s keeping you a “wantrepreneur”?

          Feel free to email me if you want to make it private – these are important questions man!

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