(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:
Be amazingly, magically spontaneous (some people do have this gift; I do not).
Do The Work. (with a nod to Steven Pressfield’s book)
Here’s my methodology to Do The Work for a five minute pitch.
Start 2 weeks ahead of time.
Pick a story narrative — what’s your angle on why you’re unique.
Outline your pitch in slide bullet points. Max 5 slides (my slide outline below).
Make slides with pictures and few words — like, use 32pt font.
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.
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.
On day 0, you’ll sound natural and spontaneous and you won’t need to see your slides.
Here’s my 5 slides outline:
Why this vision/company/product/market. (in the spirit of “Start with Why”).
What is this thing? (what does the product do, focus on interesting/different)
The Business — how do you make money. Keep it simple.
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.
Last night from midnight to 2am, I listened to eight passionate, innovative teams sharing their journey through the Purple Prize, an indigenous innovation competition in Hawaii where I am a mentor (BTW join us for the finals online!).
Even though it was late, the passion of these innovators meant I never got the least bit sleepy! Purple uses the now-common fast pitch format common to many accelerators – 5 minutes to introduce your company to potential investors and stakeholders. The fast pitch is really an art form – a performance art form. As both a performer and a consumer of this art form, I wanted to share a few thoughts on how to give a great performance. It is a performance, by the way – be yourself, but the “big stage” version of yourself. Passionate and confident. And practice!
Longer than an “elevator pitch”, shorter than a real VC pitch, it’s tricky. In just a few minutes you must concisely explain what you’re doing, why you’re doing it, why you will be successful, and what you are asking for (and not much else in 4 minutes!).
The first thing is to remember your audience. Assume they know nothing (and about you, it’s true. They know nothing. Assume nothing. Start at the beginning). On a demo day they’re likely to hear 10 of these pitches, or more. They’ve never heard a word about your company before. Their phone will buzz. Their attention will wander. Your internet/zoom will get glitchy at the wrong time. People can only consume so much information in short time. Avoid “cognitive overload” – keep it simple. Less is more. Nuance is not your friend here.
Here’s a formula:
Start with a story
Use your story to introduce your product. Simply and explicitly.
Explain how you make money. Simply and explicitly.
Explain how the world will be different when you are successful. Finish strong.
No more than 1-2 slides per minute. 5 minutes ~ 5-10 slides.
Your presentation should arc from the general down to the specific and back up to the general. Let’s unpack this a bit.
THE STORY
Your very first words need to bind people to you and your mission, and explain what you are up to. People remember stories. Please, read Mike Troiano’s https://entrepreneurship.mit.edu/how-to-tell-your-ventures-story. They won’t remember market positioning or value propositions or any of that other stuff. Tell them a story. They’re looking for a reason to like you. Give it to them. Get their attention with a story, an insight, an experience, a feeling. Don’t waste your first words on anything but your story (don’t make jokes about being last, or explain how nervous you are, or anything else).
I build Bookship, a social reading app. Here’s how I introduce myself and my product. My very first sentences, verbatim.
“Hi, I’m Mark. When my son was 16, I got him a copy of Dune for Christmas. Like most gift books, it sat on the shelf unread for a decade. A few years ago he told me he was going to read it (he’s grown now). I said, “I’ll read it with you”. What followed was a month of genuine engagement with my son. Priceless. I had a similar experience with my daughter shortly thereafter, (different book) and I said to myself, “I’m going to bottle this experience into an app so other people can get that same feeling”. And that’s how Bookship was born.
Notice: almost nothing about the product or features – it’s about the feeling, the emotion, the experience. Even better, the story is actually true. If you don’t have a good true story, remember Rule 19.
As Simon Sinek says, Start with Why. Your “why” might be a story, or it might be some phenomena or metric that speaks to you. Last night I heard the spark of many interesting stories. But often these sparks were buried in the middle of the presentation. I want to share them (with permission) because the stories are powerful, and to use them to illustrate how to make the most of them – by starting with them.
Sheila at MAGHugs is building a system for teachers to share positive news about things students did with the student and their parents (“I see you. You are valued“). Halfway through her presentation, she showed a slide with metrics illustrating the psychological challenges students face, starting with drop-out rates and culminating with a gut-wrenching statistic that every day 8 students commit suicide. Now I’m paying attention – what can we do to change that awful statistic? I’d advocate a pitch narrative that goes something like this: “Hi, I’m Sheila, and I was an educator for N decades. I can tell you many of our students are in trouble. Did you know that every day …… so, we’re building a system for positive feedback for every student through virtual hugs.“. That’s a narrative that grabs my attention and no matter what else she says, I’ll remember what she’s trying to do.
Polu Energy is building an innovative new power generation system. After hearing about the extremely powerful scientific team behind the company, and the general approach to the business, around slide 5 I learn that when salt water and fresh water come together, they make electricity. WTF? Really?? I had no idea. I’d suggest that as the opening line. “Hi, I’m Tate. Did you know that when salt water and fresh water come together they make electricity? We found a way to harness that at industrial scale. We’re Polu Energy. Blue energy from water…“. I immediately get the crazy insight that led to this company. I’ll remember that, and I want to hear more.
Preston & Gabor at Box Farm Labs are building a home hydroponics appliance. A Keurig for plants. Three or four minutes in, I hear that they started with a NASA project to grow plants in space in an automated way for long space voyages. That’s crazy shit. Hit me between the eyes with that in your first sentence. Hi, We’re Preston & Gabor. We learned how to grow plants in space for NASA, and we want to bring that to your kitchen. OK, that sounds pretty cool. Tell me more!
People remember stories. As Sinek says, “people don’t buy what you do, they buy why you do it“. But don’t belabor it. You don’t need four slides of “why”. You don’t have time. One slide. Less is More.
PRODUCT
Your Story should lead to your product. “Because of X, we built our product Y“. Explain Y (your product) in two or three sentences. Simple enough a high schooler can understand it. If you sell Carbon Offsets to Hawaii Visitors so local farms can plant food trees, like Kanu Offsets does, tell me that, just that simply, and at the beginning, so I am ready for everything else you tell me. That’s a mission I can get behind.
People can only take in so much – don’t make them work for it. Remember cognitive overload. If you want to give more detail (and you should!), do so – but only after you’ve given me a one sentence summary of what your product does, that I can internalize.
BUSINESS
Explain how you intend to make money. Tell me like I was in high school – simple and straightforward. The fancy term for this is business model. It’s surprising to me how often I hear a pitch where it’s unclear who pays for the product. For example, consider products sold into an educational context – who pays for it? The student? the parent? the teacher? the principle? the school district? Don’t make me guess. If you aren’t sure yet, that’s ok – just say so. But in a short pitch, ambiguity is more your enemy than error. If you are vague, I’ll assume the worst. But if you are precise but wrong, well, no harm no foul. Every startup makes mistakes and learns. Better to present with conviction, while offering up the chance you may learn and change in the future.
CLOSE STRONG.
The arc of your presentation is:
here’s why we’re doing what we’re doing.
Here’s what we do.
Here’s how the world will be different when we are successful.
You move from the mission to the product to the business to the vision. General to specific to general.
I’ve seen so many pitches (not last night though!), that end in a morass of details and business plans and profit margins and …. don’t do this. Close strong. Explain how the world will be different when you are successful. Leave me with a clear memory of who you are and what you stand for.
You will face some temptations when you build your pitch:
You will be tempted to tell me everything you know.Don’t. Make sure I get a clear understanding of what you do. The details can follow.
You will be tempted to cram everything onto the slides.Don’t. Complicated diagrams and paragraphs of text in 12pt font will never be understood. You might as well not show them. Big font, simple pictures, simple diagrams. There will be times later to deliver all that wonderful detail and learning you have done. Now’s not the time.
You will be tempted to glam things up – use large words and jargon to make your initiative sound sophisticated, even if it’s straightforward. Don’t. Simplicity is your friend here. Simple is good.
You will be tempted to use metaphors and generalities.Don’t. I love me a good metaphor, but in 4 minutes it’s too easy to be misunderstood, or not understood. Simple and explicit is the ticket.
I’ve recently had a few conversations with people wrestling with a decision on whether to take a particular job. Here’s my list of ten questions you should ask yourself.
Hovering over all of this are two words that might seem a little morbid.
Memento Mori. Remember that you will die.
I first learned this reading Ryan Holiday’s works, especially The Obstacle is the Way, which re-introduced me to Marcus Aurelius and his Meditations. Great life reading. Anyway, it’s not morbid, it’s liberating. It means, do what matters and do what is important. And don’t waste time on the crap.
OK, the 10 questions. If all these are a ‘yes’, the job is a keeper. If not, keep looking. Life is too short for bad jobs. (look, I get families need to be supported, people have obligations, and sometimes you just need the job and the money. But don’t settle!).
1. Does the company & opportunity have a Mission?
If they have no discernible mission, or don’t tell you about it during the interview process, it’s just a job. Keep looking.
2. Are you passionate about that Mission – does it matter? mean something to you?
Life is too short to spend on jobs that don’t matter.
3. Will I learn new things in this job?
If you’re not learning, you’re not growing. If you’re not growing, you’re stagnant. And who wants that?
4. Is there a specific person I believe I can learn from?
Ideally, it will be the person that you report to – but it doesn’t have to be. Just someone you’ll have access to on a regular basis.
5. Are there people I can teach? Do I have something to give?
This is more important as your career progresses, but learning and teaching should be hand-and-glove – you should be doing both. Your satisfaction will double if you know you are making other team members better.
6. Am I doing something new, from previous roles?
This has always been a hard and fast rule for me. The next job has to have something different. A new domain, different levels of responsibility, a different functional area. Otherwise, you won’t be learning much.
7. Is this company going to be around, or am I OK if they are not?
Figure out if the company is going to work (a startup requires a different set of questions than a big company). You’re investing a good chunk of your life in it.
Are they in an industry that’s growing? Do they have something different going for them compared to their competition? Does the company have its shit together? (Note: the interview process is a good 1st test for having their shit together – if the interview process is confused, drawn out, mismanaged, indecisive, opaque, etc. – they’ll be that way after you join too…). And if you’re not sure the company is gonna make it in the long run, but everything else looks good, then go in with your eyes open and take the gamble!
8. Do I care enough about these people, this work domain, this company, to spend 5 years of my life on it?
Life’s too short to spend on things you don’t care about, or to work with assholes. Even if the pay is good. Is the chemistry good with the people you met? Will you be excited to work with them every day? You’re going to see them more than your family! Find a good fit.
9. How many “at bats” do you have?
We all only have so many jobs to take in our life. To borrow baseball language, I call these “at bats”. How many “at bats” do you have left? When I was 50, I thought, well, I have maybe 2 or 3 more jobs left – I’m not going to waste an at bat on something that doesn’t feel quite right. When you’re 22, you have more time, and more at bats to take a flyer on.
10. How does this set me up for my next job?
When I am done with this job, what will I have learned and how can that advance my career the next time? Will it open doors for bigger roles? New industries? Maybe starting my own company? Have some idea where you want to go in your life and career, and try to take jobs that help you get ready for that. (in my list of work rules, this is #16).
OK. You got through all those questions, and the answers were all solid. You’ll notice none of the questions were about money. Not an accident. It’s not because money isn’t important – it’s because you shouldn’t start there. Figure all the other stuff out, and if you’re passionate about the role, the money will figure itself out. Just remember, “you don’t get what you don’t ask for“. If you don’t like the offer, tell them you love the opportunity but you need the compensation to make sense.
Bad news first. Good news is fun but there’s nothing actionable about it. Bad news, you can try to fix.
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)
Never let the facts stand in the way of a good story.
Hire adrenaline junkies.
Rip off the bandaid.
Never make a decision until you have to. (My take on this, via Shogun, a master class in this).
Always carry on your bags; never take a connecting flight (wait – that’s two rules)
Never release on Fridays
Don’t fight the last war. (re: when we built goby, we focused on our website even as mobile was becoming ubiquitous)
“Your reputation is important and easily damaged, and people talk”.
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….).
“Hands and Feed Inside the Vehicle at all times.”. Enjoy the ride.
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.)
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.)
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.
The three laws of email (with hat tip to Asimov’s three laws of robotics)
Never send email when you’re mad.
On the third reply, use the phone.
Reply All is not your friend.
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).
Recently I had the chance to jointly read Dune with my son Erik, Evicted with my daughter Kristen, and (gulp) Thucydides with a dear friend in Utah and one of my nephews. I reconnected with people I care about in a really meaningful way. I read books I wouldn’t have otherwise read and got more out of the books I would have read anyway. It was like our own private book club.
Reading is better with friends.
Social media is awash in book-related content. Goodreads and Facebook reviews, Instagram photos (check out #bookstagram for a cuteness overload), #fridayreads on Twitter, the list goes on. But there’s no good place to share the complete experience of reading a book.
Sure, I can write a review on Goodreads when I’m done — and it will be lost in the ocean of other reviews there. And it’s after-the-fact anyway. By the time I’m done reading, I’ve forgotten most of my special moments or insights. Sure I can post on Facebook — but nobody has any context for why I’m posting, and it’ll be lost in the sea of noise that is Facebook. I may not even be friends with the people I want to share with.
Reading a book together is a unique way of strengthening a relationship or getting the most of out a book. It deserves a purpose-built, books-aware experience, where you can share your thoughts and reactions as they happen, not two weeks later when you’re done with the book. An experience that creates companionship and context while you’re reading. An experience that helps you learn from other readers.
Introducing Bookship.
Bookship is a mobile app purpose-built for sharing your reading experiences with your family, friends and co-workers. Perfect for your book club, or just staying in touch with your friend across the country. Better still it creates a reason for you to stay in touch with them! And it’s as easy as snapping a picture or posting a note.
Reading is better with friends. Bookship is a mobile app for sharing your reading experiences with your family, friends and co-workers. With Bookship you can invite fellow readers to read along with you, whether they’re reading via a physical book, an ebook, even an audiobook.
With Bookship you can invite friends, family and co-workers to read along with you, whether they are reading a physical book, an ebook, even an audio book. Post and react to comments, thoughts, photos/videos, quotes, links and questions, all in an easy-to-use chat-style interface. Get notified when others post and keep in sync with them while you read by sharing your location. Dogear passages with a quick photo with your phone, even have Bookship extract the text from the page you took a picture of!
Whether it’s reading a great novel with your best friend across the country, a business book with your co-workers, or participating in a neighborhood book club, Bookship enriches your reading experience and your relationships.
Bookship is available now for iOS and Android, and it’s free to start. Get it here: https://www.bookshipapp.com
