My Music

"You can't take it with you."

There are a few reasons to share what you know. First, your accumulated knowledge will disappear when you do. Second, it's incumbent on all of us to make those who come after us smarter than we were. Third, having people question your assumptions makes you smarter.

— Steve Blank, You Can't Take It With You. This is the whole reason the deck exists.

Later Open-Source Knowledge

Step one: know yourself. Step two: find your gateway experience.

Find the experience that opens the door. Give it everything. Derive every bit of value out of it and never stop building momentum. Keep doing things. Nothing about my own trajectory was a plan — it was one experience I took seriously, and then the next one it made possible.

Later Know Thyself

The five keystone habits.

• Meditation
• Diet
• Exercise
• Daily pages / journal writing
• Creating a budget

Keystone habits are the ones that drag the other habits along behind them. These five are mine.

Later Crafting Your Average

The recipe for a life you want to live.

• Be true to yourself. No one's opinion of you matters more than your opinion of you.
• Live every day like it's Saturday. Don't be lazy. Every day you should be excited to wake up and do what you're doing. If you're not, do something different.
• Don't be afraid to break the norm. Just because it is what everyone does doesn't mean it has to be the way you do it.

Are you here for a degree, or for an education?

Those are two different purchases, and most people only ever make the first one. A degree is a credential someone else designed. An education is something you have to go build on purpose, usually out of the same raw materials sitting right in front of you.

I tried and failed to build my own education. It's the thing I'd most want back.

Later Employees Wanted, The Educated Need Not Apply

Everyone gives lip service to "continuous education." If you don't actually take advantage of it, you're being stupid about it.

We have access to more information and knowledge today than at any other point in history. The platforms change every few years and it doesn't matter which one you use — what matters is whether you have an appetite and a system. Free courses, open courseware, and yes, friggin' YouTube, ya dummies.

I've written more about this in Education: Turning a Debt Market Into an Equity Market.

Treat the course catalog like a menu, not a requirement sheet.

If I were designing an education from scratch, I'd pick the most efficient path to the credential, and then spend the freed-up time reading the catalog end to end and choosing what I actually wanted to learn. Auditing is almost always available and almost never used. I started going through the catalog alphabetically and only got a few letters in before I got genuinely sad about everything I'd missed.

I surveyed a group of people about their biggest educational regret. The answers rhymed.

• "I would have added a major in something skill-based with a clear career path."
• "Not taking a wide breadth of classes."
• "Working one on one with professors."
• "I wish I would have worked and created things with my peers more than I did."
• "Because grades are so important I'm discouraged from taking classes that really challenge me, so I don't learn the skill."
• "Learning how to think creatively and critically instead of just learning how to get good grades."

Later I’m the Dumbest Person in the Room. Again.

Guess what — you're not busy.

"I'm pretty busy, thanks though" is almost never a statement about capacity. It's a statement about priority, and it's usually an accurate one. I've watched opportunities that were meant to live die because the people who could have carried them were "busy," and I've watched others survive purely because someone decided they mattered.

I wrote this one up as The Natural Selection of Time.

Don't kill opportunities — but don't let your priorities die while you flirt with them.

"In running back and forth among the things that might be important, we forget to spend enough time on what really is important. It's a fool's game, and one that we are remarkably adept at playing."

— Dan Ariely, Predictably Irrational, from the chapter on keeping doors open. There's a game in it that rewards you for clicking the green door, but the other doors disappear if you ignore them. Most people spend their clicks keeping doors alive.

Your feed is only ever as good as the people in it.

Twitter has a huge adoption problem — it scares everyone. It is also the most effective, timely, digestible source of news and knowledge in existence if you follow the right people. The tool is not the thing. The curation is the thing.

Later A Latticework of Knowledge

"I write because I don't know what I think until I read what I say."

Writing is not how you report a conclusion. It's how you find out whether you have one. Pair it with something — anything — that tracks tasks, reading, and progress. Whatever the system is, the discipline is that nothing lives only in your head.

— Flannery O'Connor. The corollary: saving articles you never read is not a knowledge system, it's a landfill.

Later On Writing

Strategic googling is a real skill, and it's one of the most valuable ones I have.

Most of what I "know" is not stored. It's the ability to get from a vague question to a credible answer faster than the person next to me. That's practiced, not innate.

Later Building the Global Knowledge Graph

"The average American reads zero books a year."

Amazon is for search and purchase — use the Kindle app on mobile and desktop so the book is always with you. Small independent bookstores serve a completely different role: discovery. I found The Education of Henry Adams because all I knew was that I was interested in the political science section, and a used bookshop in Boston had one.

This is the habit that eventually turned into a bookshelf and a book note for everything I read.

Later Read Old Books

Draw the idea.

"We are visual creatures. When you doodle an image that captures the essence of an idea, you not only remember it, but you also help other people understand and act on it — which is generally the point of meetings in the first place."

— Tom Wujec.

Nothing is more valuable than getting out and doing something. No survey can invalidate an idea.

Interacting with people and testing the idea on them is the core activity of an entrepreneur. Everything else is preparation for it or reporting on it.

Later I finally talked to a customer…and it was hard.

What hustle actually looks like.

A friend had an idea for crowd-shopping. He built a WordPress site, put up an image for a single product sale, and then manually updated that image every time somebody bought one. No backend. No product. He made a couple hundred bucks. That is hustle.

Grit: people are going to tell you your idea is stupid.

You need to be logical, data-centric, and thick-skinned, in that order. Being thick-skinned without the first two is just stubbornness. Chris Sacca passed on Airbnb because he thought it was going to get somebody murdered.

Later The Coward's Conviction

The people who look like they're hedging are sometimes just managing risk well.

Adam Grant tells the story of turning down a group of students who were selling stuff online: they'd all taken backup internships, they'd all lined up backup jobs, and the day before launch there still wasn't a functioning website. He declined to invest. They named the company Warby Parker.

— The Surprising Habits of Original Thinkers.

If you want to start a startup, go work at someone else's first.

"Working for someone else's startup, I learned how to quickly cobble solutions together. I learned about uncertainty and picking a direction regardless of whether you're sure it'll work. I learned that most startups fail, and that when they fail, the people who end up doing well are the ones who were looking out for their own interests all along... I learned how quickly problems of scaling a development team crop up, and how early you should start investing in automation."

Later The Apprenticeship Litmus Test

Design thinking is five modes, and almost everyone skips the first two.

Most people call the last three "design." The first two are where the actual leverage is.

Later Is The Lean Startup a Stupid Way to Start a Company?

Empathy first, because need is the one input you cannot invent.

"Without understanding the perspective of the people you are trying to serve, any design is already starting off missing the most essential element: need." To get there you have to actually ask questions, hear stories and scenarios, understand the challenges, and find what's common across them.

Later Learnable Empathy

Define a point of view, then have the nerve to focus.

"The goal of the Define mode is to craft a meaningful and actionable problem statement — a guiding statement that focuses on the insights and needs of a particular user."

"Focus is scary — until you realize that it only means turning your back on markets you could never have anyway." — Clayton Christensen.

Question storming, not brainstorming.

"When participants are generating questions, they tend to dig into a problem and challenge assumptions. The process gives people permission to ask fundamental questions that often don't get asked; not just 'how can we do it better?' but also 'why are we doing this in the first place?'"

Don't ask "would you use this?" Build the closest thing you can and ask "will you use this?"

Everything can be prototyped. The goal is to get the prototype as close to the reality of the experience as possible, then watch how people actually use it instead of asking them to predict themselves.

Build, measure, learn.

Ideas become a product, the product produces data, and the data is what changes the ideas. Skip a step and you are just shipping.

A minimum viable product that doesn't teach you anything is less than viable.

The MVP is "that version of a new product which allows a team to collect the maximum amount of validated learning about customers with the least effort." Validated means data demonstrating that the key risks have actually been addressed — which means building more than a symbol. People have to be able to interact with it.

— The Lean Startup. Though I've also argued with this book in public.

Build the feature that tests your riskiest assumption.

The riskiest assumption is the one that, if it's wrong, breaks the whole model and you start over. Underneath it sit two leaps of faith. The value hypothesis: will anyone actually use this? The growth hypothesis: will enough people use it to justify its existence? And the point of iterating is never to speed up one step — it's to speed up the whole loop.

Every process, class, club, or organization has a business model. It's just how they take one thing and create more value out of it.

Become a "yes, and" person.

Improv is the single best thing I've ever done to develop creativity. Building on ideas, creating new products, solving problems, knowing what to say in a room — it all comes from the reflex of adding to what's in front of you instead of shutting it down. Ask what else you can do with this. Take notice. Keep it simple. Embrace absurdity. Reposition. Just improvise.

Later Creativity as Connectivity

Venture capital and private equity are two entirely different games played with the same instrument.

• Environment: PE is control; VC is chaos.
• Medium: PE works in numbers; VC works in human beings.
• Primary lever: optimized structure vs. disruptive innovation.
• Investment trigger: underutilized assets vs. team.
• Assumption: rational actors vs. irrational ones.
• Role of probability: precision vs. serendipity.
• Parallels: classical music, fine art, farms and assembly lines vs. jazz, street art, rainforests and design thinking.

Later Venture Capital Doesn't Exist

The math, in its simplest possible form.

Venture: pre-money $9M, investment $1M, post-money $10M. The VC owns 10%. The company sells for $100M and $1M became $10M.

Private equity: value the company at $100M, invest $10M, borrow the other $90M. Over five years it throws off $36M a year, half of which pays down the debt. Sell for $200M. That's not a 100% return on $100M — it's a 1900% return on $10M.

Everything else in either business is an argument about which inputs to that arithmetic are believable.

The core formula of a business is eight questions.

• What do they do?
• How do they do it better or cheaper than anyone else?
• Who pays for it?
• How much do they pay for it?
• How often do they pay for it?
• How long do they keep paying for it?
• Who else sells it?
• How many people would ever buy it, or anything like it?

I have never found a company these don't work on, and I've never found an analyst who could answer all eight quickly.

Later What Is An Investor

Size a market twice, from both directions, and see if the two numbers meet.

Top down: the global diaper market is roughly $50B, the US is about 5% of global population, so call it $2.5B.

Bottom up: 320M people, 3.7% under age three = 11.8M. Five diapers a day is 1,825 a year each, so 21.6B diapers, at 20¢ each = $4.3B.

They don't match, and that gap is the actual work. A number you built yourself is worth more than a number you found.

Valuation by multiples is mostly an exercise in choosing your comparables honestly.

Find companies with publicly available statistics, pull their enterprise value to revenue or EBITDA, average the multiple, and apply it. $1M of revenue times a 2.7x multiple gives you a $2.7M pre-money valuation. The arithmetic takes a minute; picking the right comps is the entire judgment.

Later What's In a Valuation?

The numbers a founder should be able to produce without flinching.

• Revenue: monthly for six months, yearly for three years, by channel
• Growth: month-over-month, year-over-year, and the rate of decline in that growth
• Gross margin, and where it's heading
• MRR, churn, CAC, LTV, and the ratio between the last two
• Cash in the bank, burn rate, runway
• Amount raised, terms of the last round, what's closed vs. soft-circled
• Time to break-even

The longer list is Andreessen Horowitz's 16 startup metrics — including the chart tricks people use to hide the answers.

Whatever you are, be a good one.

Some paths are completely paved. Accounting: internships, the CPA, a big four firm. Consulting: internships, case interviews, network. Banking: internships, technical interviews, network. If that's what you want, the path is known and you should walk it deliberately. The interesting question is the one nobody has a flowchart for — not sure yet, and looking for something different.

Later Back To The Grass

The most useful person in the room is almost never the person on stage.

I once went to an event specifically to meet the speaker, who had just been through a big merger. While I was waiting in line to talk to her, I ended up talking to the consultant who had actually run the merger. She turned out to be more helpful to me than anyone else there, and she's still someone I'm glad to know.

Later Getting In The Right Rooms

Networking is opportunistic relationship building. You should almost never be reaching out to someone for the first time to ask for a job.

Find the people you think you could actually relate to. Reach out. Introduce your interest and propose a next step. Phone calls, coffee, events they'll be at. Don't be afraid of anyone, and don't focus on asking for favors — focus on building the relationship, and on practicing enough that you don't sound like a weirdo.

Later Relationship Liquidity

Run your network the way a company runs its customers.

Sales teams would never keep a pipeline in their heads, and then everyone tries to keep their relationships there. Call it network relationship management: who you know, when you last talked, what they care about, and what the next touch should be. A spreadsheet is enough. Having nothing is not.

This eventually became one of the systems I still run today.

A resume is not personal salesmanship. It's proof you're the person they're already looking for.

Expectations are the whole game. They want to be surprised, but they're expecting a particular format, and you should know exactly what that format is before you decide to deviate from it.

In an interview: be a person, have a conversation, don't be a robot. Or a tool.

I once gave someone a practice case about a man deciding whether to keep his coffin-making business. They asked what factors might push him to sell. I said, "well, his son just died, so he's trying to decide if he can handle keeping the business." Their response was "okay, cool." I kept thinking: this guy's son just died. That's not cool.

Interview prep culture is very good at producing people who have optimized the humanity out of themselves.

Changing the world is a specific technical act: shifting an equilibrium.

Understand the world as it is. Envision a new future. Build a model for change. Scale the solution. The framing comes out of social entrepreneurship, but the principles apply to any product meant to change something.

— Getting Beyond Better, still one of the best books I know on how to think about this.

Later Saving the World is Like Cleaning House

Design for humans, and assume they're irrational.

Human-centered design and behavioral economics are the same insight arriving from two directions: people do not behave the way your model says they should, and the only way to find out what they'll actually do is to go watch them. Start with the Design Kit, and read everything you can find on behavioral economics.

This is where the deck ended, and honestly it's where most of what came after it started.