(this is a repost of something I wrote a long time ago on LinkedIn)

Bookship was very fortunate to be selected by The Bookseller as one of six candidates for BookTech Company of the Year. Super exciting; great validation; great reason to go to London :).

As part of the event, each candidate gets 5 minutes to pitch, hard stop at 5 minutes.

Now, 5 minutes is tricky. Too short for much in the way of slides. Too long to just stand there and talk — you’ll forget stuff. I decided to go for the “pretty picture” school of slides, to keep me on track — but I wasn’t going to read my slides.

Afterwards, I received a very nice compliment from one of the other companies — “you were great! You were so natural and spontaneous!”. I was flattered. But my pitch was anything but spontaneous. It was very carefully crafted to sound spontaneous.

I’m aware of two ways to sound spontaneous and natural when pitching:

1. Be amazingly, magically spontaneous (some people do have this gift; I do not).
2. Do The Work. (with a nod to Steven Pressfield’s book)

Here’s my methodology to Do The Work for a five minute pitch.

1. Start 2 weeks ahead of time.
2. Pick a story narrative — what’s your angle on why you’re unique.
3. Outline your pitch in slide bullet points. Max 5 slides (my slide outline below).
4. Make slides with pictures and few words — like, use 32pt font.
5. Talk out loud — really — out loud — in your own words, for each of those items. Record it or write it down verbatim. Hone it so it’s short enough and you can say it without tripping over your tongue.
6. Every morning, for 2 weeks up to the event, spend 5 minutes and just read your notes out loud. Out loud. Not in your head. Out loud. Maybe record it. By the end of the first week, you probably won’t need your notes.
7. On day 0, you’ll sound natural and spontaneous and you won’t need to see your slides.

Here’s my 5 slides outline:

1. Why this vision/company/product/market. (in the spirit of “Start with Why”).
2. What is this thing? (what does the product do, focus on interesting/different)
3. The Business — how do you make money. Keep it simple.
4. The Team (why will this team succeed?).
5. Restate the Why (focus on “inevitability”- along the lines of Tom Tunguz’s http://tomtunguz.com/inevitability/).

The words for each of these slides should be 3–5 sentences, max. More and you’re out of time.

I think steps 5 and 6 are the key. People’s speaking voices and writing voices are different. Speaking out loud means your pitch is natural to how you speak, not how you write. Refine your words, boil it down so it fits in your time slot and you can say it out loud without tripping over your tongue.

One of the things you learn from playing an instrument is that a few minutes of practice a day is way better than 1 hour a week all at once. Harness this — just spend that 5–10 minutes in the morning when you are fresh and in a week the words will be stuck in your head.

Repetition and brevity are your friends. People can’t read your slides and you shouldn’t either. Convey the key points simply and clearly and they will fill in the details themselves.

And smile while you talk!

Leroy Jethro Gibbs of the NCIS TV show has a pithy set of rules.

Here’s my version, adapted for life in the professional/startup world. (some of these are a bit cryptic – someday, blog posts for each of them).

1. Leave your politics at home.
2. Gibbs is wrong (Gibbs rule #6). Apologizing doesn’t show weakness, it shows strength. If you’re wrong, admit it.
3. Do something every day to earn your team’s loyalty.
4. Hire your own damn people. HR won’t do it for you.
5. Somebody on your team will always make more money than you. Get over it.
6. Never confuse selling with implementation.
7. Time is my most valuable commodity. With respect, get to the f’ing point.
8. The deal’s not done til the money’s in the bank. And sometimes not even then.
9. Feed the troops. An Army runs on its stomach.
10. Equal pain for all. unpleasant task = everybody helps.
11. Don’t forget to manage up.
12. Take care of your stars. I mean, really take care of them.
13. Always return emails & phone calls
14. Honor your mentor.
15. One hour a day, one day a week, don’t think about work. Harder than it sounds. Do it. (I learned this from my mentor).
16. Every opportunity prepares you for the next one. (see rule #5).
17. Bad news first. Good news is fun but there’s nothing actionable about it. Bad news, you can try to fix.
18. When you have to make a decision, think carefully, ask for opinions. Then make a decision and don’t change your mind. (Indecision is fatal in a leader)
19. Never let the facts stand in the way of a good story.
20. Hire adrenaline junkies.
21. Rip off the bandaid.
22. Never make a decision until you have to. (My take on this, via Shogun, a master class in this).
23. Always carry on your bags; never take a connecting flight (wait – that’s two rules)
24. Never release on Fridays
25. Don’t fight the last war. (re: when we built goby, we focused on our website even as mobile was becoming ubiquitous)
26. “Your reputation is important and easily damaged, and people talk”.
27. Remember, you can always say “No”. Later. (ie. don’t close things off too soon – you don’t have to commit just because you take the meet or offer the phone call….).
28. “Hands and Feed Inside the Vehicle at all times.”. Enjoy the ride.
29. Next slide. “Great Launch! Next Slide”. (from my first post-launch goby board meeting, after I showed the celebratory slide in the board meeting. One of my board members said this almost as soon as I put up the slide. The point: be future-focused and keep driving for more.)
30. Paraphrasing Gibbs: When the Job’s Done, Walk Away. (when you step out of a job, don’t take another one for two months if you can help it. Your brain will change.)
31. Be (civil) In The Arena. (re: Roosevelt quote). The Arena is The Internet and Social Media. As a leader of your company, be present. Don’t be afraid to respond to your critics as well as your friends. But be civil. Flies, Honey, Vinegar, etc.
32. The three laws of email (with hat tip to Asimov’s three laws of robotics)
    1. Never send email when you’re mad.
    2. On the third reply, use the phone.
    3. Reply All is not your friend.
33. Always close the loop on an intro. (if I introduce you to a VC, let me know how the meeting went. Who knows, I might have back door info….plus, it’s just polite).
34. If you’re going to eat shit, don’t nibble. (originator: Ed Gillis @ PTC)

Further Rules reading: George Washington’s Rules, Fred Harvey’s Rules, Rules I gleaned from Steven Pressfield.