10 Rules for Writing an Essay or Advising Anyone

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So, I should warn you, I'm about to release a new short form essay called "Galapicon Valley and the Rise of Black Frankenstein" in about a week or so (it's currently under draft review).  Some people have asked for early access, so if you want to get early access you can do it here.  This essay is part one of a five part compilation of essays which together represent a kind of state of the union'ish essay that may just end up being the longest blog post in the history of the Internet.  I really don't know if anyone will read it, but I didn't think anyone would read the Cult Creation essay either and it now has over 40,000 views.

But before I post my next essay, I thought I would share my thinking on how I came up with the rules that I try to follow for writing any essay.  I'm interested in what you think, or if they can be improved.

Please step forward and enter my mind - A Founder's Contract

When I sat down to write the Black Frankenstein Essay I realized I needed a basic construct to refer back to when deciding what to say and what not to say in my essay.  I tried to remember what it felt like when I was 19 years old which is when I started my career as an entrepreneurs placing 2nd in my school’s business plan competition (mainly as a result of wearing my hair in a Samurai Warrior hairdo during the final presentation). 

I thought about what I would have wanted some old fart like me to tell the younger me. 

So even though I risk the ridicule of my friends for writing a short essay where I get into an argument with myself, I sat down and transported myself back to that time in my life and became my younger self.  Then I imagined that I had the license to ask my older self to agree to some basic constructs before advising me - The things that many first time entrepreneurs wish they could say to their mentors, but don’t because it’s too awkward to say.  But since I am me and I’m fine with offending me, I’ll say the things to my older self I wish I had said back then to my mentors. 

1. Skip the obvious pieces of advice and share the most hard fought, most valued lessons that you’ve learned over the years.  Act as if I’m a new soldier coming in to serve my first tour of duty and your a seasoned warrior that’s been on the ground for many tours.  Tell me where the land mines are, help me survive, help me win the battlefield;
    
2. Hey me, do not bullshit me.  Do not augment your stories or re-write history in subtle ways that make yourself look good and will make me screw up;
    
3. Give me actionable advice, not funny little stories that prove how cool you are and that you hang out with all of the other cool entrepreneurs;
    
4. Remember where I am in my life - I have no money, no track record, a resume that couldn’t fill a page and an investor network that couldn’t fund a pizza party.  Don’t give me advice that you can do because you’re you.  Tell me things I can actually act upon;
    
5. Please give me advice that is actually relevant to now.  If you go rambling on about how back in the day you could buy a snickers bar for twenty five cents, how your girlfriend wore leg warmers and how you used to break dance for money, I’m going to commit suicide and I’m taking you with me.  Don’t tell me how to raise money in the 80’s, 90’s, in the dot com boom or even how to raise it last year.  Tell me how to raise it now;
    
6. Your legacy is me.  I know you think you're rich and accomplished and everything, but let’s be clear about one thing.  You’re an old fart and you can’t escape that fact.  I’m twice as smart as you, I have 3 times the energy and I work at 4 times the speed.  I want to suck your brain dry and then replace you.  If you really are a true entrepreneur, then you should respect my intentions, tell me what I want to know and accept your inevitable fate with dignity;
    
7. Be clear and be complete.  I want everything.  Don’t leave out important connectors, precedents or the little things that make a big difference.  Don’t give me the stuff I could read in a book.  Give me the stuff that would never go in a book;
    
8. Help me navigate the drama.  There’s a lot of stuff going on in the Valley.  There’s Y-Combinator, the Super Angels, the Investeratzi who just seem to follow the Super Angels, and the VCs.  It seems like we, as entrepreneurs, have to navigate pretty tricky waters.  Help me understand what’s real about my options and the pain/benefit of each.  I really want someone to help me cut through all of the over-dramatic bullshit that’s out there.
    
9. Help my company, not yours.  Don’t give me advice that was only relevant to the companies that you created.  I don't give a flying hoot how cool it was to bookmark something for the first time.  Take the time to extract the concrete lessons that allow you to build up constructive, actionable nuggets that are abstracted away from your specifics.
    
10. Understand the weight of your responsibility.  Remember, you’re not recommending a golf club to me, or a video game.  You’re giving me advice on the most important thing to me in the world right now.  I may actually do many of the things that you tell me, so please think through the things you say to me because I need to find people to trust, to believe in; and right now, you’re it.

Doing this made me remember what a cocky turd-ball I was when I was younger.  But are young entrepreneurs any different today?  In the end, it doesn't really matter how insensitive my 19 year old self was to my older self of today - if you can strip out the 'tude, you'll see that by following my younger self's request, real value would be created.  

And so even though I'm sorely tempted to kick my own self's ass, I promise to do my best to follow these principles.  I truly believe that by doing so, it ultimately provides more value and what's more, it keeps me on my toes and challenges me to keep in good enough brain shape to stay at the top of my game as an active founder.  

Steve.

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