Before you write your first eBook, here’s 15 things you need to know

Years ago, when I was still working in venture capital, I committed to the world (ok, a small world ;) via my blog that I would write a book about careers in venture capital.

After I made that commitment, I left the VC world without having written the book (1st year of my children’s lives), went to a startup (no time to write a book), and finally last year…published the book!

Now that I’ve actually written and published the darn thing, a post-mortem is in order! Here’s what I learned about the world of book publishing, and about myself, during this process…with some additional tips and suggestions smattered in:

  1. You’re going to be self-publishing your first book, unless you’re famous (or at least famous on Twitter). Publishers expect you to bring a big following to the table if you want them to work with you.  Same goes with literary agents.
  2. If you still want to find a publisher, you’ll need to write a 50 page proposal — basically a big abstract — in order for them to consider taking you on.
  3. Just 1% of authors earn out of their advance.  (Are you still surprised about #1 and #2? :)
  4. Smashwords provides a great platform for converting your eBook (which needs to be written in a specially formatted MS Word file) and converting it to all of the major eBook formats.  I thought I would need all of the formats, but it turns out that the only format I’m actually distributing is the PDF.  Go figure.  Which leads me to…
  5. …Gumroad.  Gumroad provides a ridiculously simple platform to distribute and sell eBooks as well as other digital goods.  If you don’t need a lot of fancy features and just want a super simple sales and distribution platform, it’s a great service and they eat into much of your profit margin!
  6. Smashwords has a list of people who will produce book cover art using stock photos, and typically you’ll pay on the order of $40.  Now that I’ve discovered fiverr, I bet I could get a great cover for just $5-$10 the next time around.
  7. Luckily I had a very nice friend who proofread the entire 30 page eBook for me as a favor.  Other editors quoted me wildly varying rates (<$100 and upwards of $500).
  8. Long plane flights rock.  I wrote almost the entire first draft of content on a couple of cross-country plane flights.
  9. If you maintain an email list of potential readers of your book, share parts of the book with them as you go through your writing process.  It’s a great way to get feedback and your readers will appreciate being part of the creative process.
  10. No email list yet?  Get started today.  A great “give” is to provide a portion of your book to new subscribers to your list.
  11. Once you release the book, create a nurturing campaign (also called drip marketing) so that new subscribers to your list will be notified that the book is available for sale.  Ideally you’re notifying them after you’ve provided other value in the nurturing campaign.  I use Madmimi for my email list, which has support for Drips (their term for a nurturing campaign). BTW if you sign up, they’ll shave a few bucks off of my bill, too! ;)
  12. Write a blog post stating your intention to write a book, and repost it to all of your social networks so that you’re a liar if you don’t follow through! :)
  13. Not sure if you have a story worth telling or at what price to sell your book?  Create a poll on your blog (here was mine) to gauge demand for the book as well as potential price points.
  14. Consider giving your book away for free to your Tribe.
  15. There are actually services, like Hyperink, who will write your book for you in exchange for a portion of the earnings.  I applied to see if they’d write mine for me, but they never wrote back (*sniffle*)

I also wanted to take this opportunity to thank a few people who were involved in different parts of this experience:

  • Keith Cowing, who inspired me to write this post
  • Carla O’Connor, my awesome friend and copyeditor
  • Lucinda Blumenfeld, for giving me a crash course on the world of publishing
  • Super-connector Chris Phenner, who introduced me to Lucinda.  (BTW, Chris runs a great email list where he talks about ad tech and social ads.  He’s been in the space for a long time and is a great guy to follow.)

Last, but not least, I recently finished my second eBook!  It’s called 15 Emails That Worked. 

In the book, I share the actual email templates and describe the best practices that helped me get meetings with hard-to-reach entrepreneurs and VCs during my last job search.  It will definitely be useful to you if you’re job hunting in the startup and VC world, but the tips and techniques also apply to anyone who is looking for more effective ways to connect with busy people via email.

If you’re interested in getting this eBook for free, simply click here to learn more.


  1. Sorry,

    I think your article is very negative and it’s very far away from reality.

    Here some facts:

    1. Do you know Amazon? You can keep the 70% (or the 35%, depending on the price and the market)

    2. How can a “simple html” be complicated to do on MS Word? Easy as cake. And there are many programs that will transform it to wahtever format.

    3. I have published 3 books already. Amazon gives you tons of options to promote it. Well, tons… 5 free days each 45, special price, etc.

    4. Wanna sell by yourself? Buy an online shop template for html (8$ from themeforest), an info domain (2 bucks per year from 1and1) and the cheapest hosting (20 bucks per year). Then, for Payments, use Payhip (which uses Paypal).

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