On Love & Money

“What the issue comes down to for me is this:

I believe that life happens on two levels. The body-level tells us to go commercial. The soul-level tells us to follow our hearts.

If you’re lucky, you’re like Bruce Springsteen. You live on the heart level and you never have to leave it. You ignore every concept of “what will sell.” Instead you dive deep into your own world and your own passions. You go from Born to Run to Darkness on the Edge of Town to The River to Born in the USA and you keep going.

If you’re the Boss, you don’t have to sell out. You don’t have to pander to your audience. Instead you lead them. They want you to. You tell your story, follow your obsessions—and, holy Asbury Park, your secret, inner, crazy life turns out to be their secret inner crazy life too.”

Stephen Pressfield


I’ve got friends on both sides of this argument.

Most of the ones on the “for love” side do that for a living—they tell people how to do what you love for a living.

Most of the ones on the “for money” side seem to say so just to spite the guys on the love side.

Pressfield helps me to cut through the platitudes and go to my story: what’s been my experience?

I’ve been in safe and profitable jobs. For one reason or another I’ve quit every one.

I’ve been enthusiastic about lots of stuff — been in love a lot — and most of those haven’t made me much money.

But I seem to make better friends through the love stuff. (Most of the friends that I mentioned above, in fact. Except for one, whom I met when I was in one of those jobs I quit).

And doing the love stuff has led me to where I am now, creating a learning community for online entrepreneurs. I can’t tell if this one’s more for the love or for the money. I’m hoping it’ll do both nicely.

And it should be said, of all the love stuff I’ve done, I never really went all in on any of them. This is the first time I’ve had enough experience, stones and muscles to focus and dedicate myself to anything.

So that’s my new answer to the question: what does your own experience tell you?

Jim Coudal’s Advice on Selling Your Own Product

“Two quick points. Not every idea is going to work. Know that going in. Ideas tend to follow the path of least resistance and more often than not that path is the one where you find yourself talking an idea to death, by getting hung up on the ‘what ifs.’ So you need to actively push ideas out and embrace failure. Fail spectacularly whenever possible.

Secondly, every single person I have ever met or corresponded with about leaving the work-for-hire world and trying to create something of their own, something that they really care about, says exactly the same thing. Win, lose or draw they always express the same thought and most of the time they say it in exactly these words.

What they say is, ‘I should have done this sooner.’”

Jim Coudal

Startup Commandments — The Hardest Lessons to Learn

Paul Graham wrote a masterful thing about the hardest lessons for startups to learn. Below is my summary and notes recorded here so I can take them with me forever. Check out his original article here.


1. Release Early. Get a version 1 out fast, then improve it based on users’ reactions. Not something full of bugs, but something minimal. There are many reasons to do this. Perhaps the most important reason is that it makes you work harder.

“Users hate bugs, but they don’t seem to mind a minimal version 1, if there’s more coming soon.”


2. Keep Pumping Out Features. If you’re going to start with something that doesn’t do much, you better improve it fast. I don’t mean make your application ever more complex. By “feature” I mean one unit of hacking — one quantum of making users’ lives better.

“…people get used to how things are. Once a product gets past the stage where it has glaring flaws, you start to get used to it, and gradually whatever features it happens to have become its identity. […] I think the solution is to assume that anything you’ve made is far short of what it could be.”


3. Make Users Happy. A startup has to sing for its supper. Tell visitors (cater to casual visitors) what your site is about by showing them.

“Users are a fickle wind, but more powerful than any other. If they take you up, no competitor can keep you down.”


4. Fear the Right Things. Disasters are normal in startups — they won’t kill you unless you let them. Don’t fear the established players, fear other startups you don’t know exist yet — they’re cornered animals like you. Compete against what someone else could be doing, not just what you can see people doing.

And in any case, competitors are not the biggest threat. The three biggest are: internal disputes, inertia, and ignoring users.

“You should compete against what someone else could be doing, not just what you can see people doing.”


5. Commitment Is a Self-Fulfilling Prophecy. The most important quality in a startup founder is determination. Not intelligence — determination. Running a startup is like walking on your hands: it’s possible, but it requires extraordinary effort — and it happens against the backdrop of regular disasters. Not stubborn — you have to be determined, but flexible, like a running back.

“Everyone who deals with startups knows how important commitment is, so if they sense you’re ambivalent, they won’t give you much attention. If you lack commitment, you’ll just find that for some mysterious reason good things happen to your competitors but not to you. If you lack commitment, it will seem to you that you’re unlucky.”


6. There Is Always Room. It’s not likely that in a hundred years the only social networking sites will be Facebook and twitter. At every point in history, even the darkest bits of the dark ages, people were discovering things that made everyone say “why didn’t anyone think of that before?” The number of possible startups is limited only by the amount of wealth that can be created.

“Startups make wealth, which means they make things people want, and if there’s a limit on the number of things people want, we are nowhere near it.”


7. Don’t Get Your Hopes Up. Founder optimism is a nuclear reactor: a very dangerous source of power. It’s ok to be optimistic about what you can do, but assume the worst about machines and other people. Just assume it — whatever “it” is, a deal, a partnership, a sale, etc. — isn’t going to work out. Not to save yourself from disappointment, but to prevent yourself from leaning your company against something that’s going to fall over, taking you with it.

“It’s ok to be optimistic about what you can do, but assume the worst about machines and other people.”


“It seems ridiculous to me when people take business too seriously. I regard making money as a boring errand to be got out of the way as soon as possible.”

Paul Graham on the 2 Things Your Site Must Do

“The vast majority of people who visit your site will be casual visitors. It’s them you have to design your site for. The people who really care will find what they want by themselves.

The median visitor will arrive with their finger poised on the Back button. Think about your own experience: most links you follow lead to something lame. Anyone who has used the web for more than a couple weeks has been trained to click on Back after following a link. So your site has to say “Wait! Don’t click on Back. This site isn’t lame. Look at this, for example.”

There are two things you have to do to make people pause. The most important is to explain, as concisely as possible, what the hell your site is about. […] the other […] is to give people everything you’ve got, right away.

In the best case these two suggestions get combined: you tell visitors what your site is about by showing them.”

Paul Graham


Sounds pretty simple. It will always be easier to design your site if what you do/offer is interesting.

Elements of a Sustainable Business & Business Plan — Sequoia Capital

“The best founders are clear thinkers. they don’t need many words, charts, spreadsheets or slides to express their ideas.”

Sequoia Capital


Sequoia Capital has a concise and strong little number on their website here. Printed below because I want to find this later, regardless of their “web content publishing strategy.”

Elements of Sustainable Companies:

  • Clarity of Purpose. Summarize the company’s business on the back of a business card.
  • Large Markets. Address existing markets poised for rapid growth or change. A market on the path to a $1B potential allows for error and time for real margins to develop.
  • Rich Customers. Target customers who will move fast and pay a premium for a unique offering.
  • Focus. Customers will only buy a simple product with a singular value proposition.
  • Pain Killers. Pick the one thing that is of burning importance to the customer then delight them with a compelling solution.
  • Think Differently. Constantly challenge conventional wisdom. Take the contrarian route. Create novel solutions. Outwit the competition.
  • Team DNA. A company’s DNA is set in the first 90 days. All team members are the smartest or most clever in their domain. “A” level founders attract an “A” level team.
  • Agility. Stealth and speed will usually help beat-out large companies.
  • Frugality. Focus spending on what’s critical. Spend only on the priorities and maximize profitability.
  • Inferno. Start with only a little money. It forces discipline and focus. A huge market with customers yearning for a product developed by great engineers requires very little firepower.

Elements of a Business Plan

  • Company Purpose. Define the company/business in a single declarative sentence.
  • Problem. Describe the pain of the customer (or the customer’s customer). Outline how the customer addresses the issue today.
  • Solution. Demonstrate your company’s value proposition to make the customer’s life better. Show where your product physically sits. Provide use cases.
  • Why Now. Set-up the historical evolution of your category. Define recent trends that make your solution possible.
  • Market Size. Identify/profile the customer you cater to. Calculate the TAM (top down), SAM (bottoms up) and SOM.
  • Competition. List competitors. List competitive advantages.
  • Product. Product line-up (form factor, functionality, features, architecture, intellectual property). Development roadmap.
  • Business Model. Revenue model. Pricing. Average account size and/or lifetime value. Sales & distribution model. Customer/pipeline list.
  • Team. Founders & Management. Board of Directors/Board of Advisors.
  • Financials. P&L. Balance sheet. Cash flow. Cap table. The deal.

Joe Di Stefano’s Project Management Mantra

“What you are asking at this stage has changed the project considerably from the documentation and the scoping process that we undertook and has been approved. We could continue, but I believe it would jeopardize the quality and the integrity of what needs to be delivered. If what you are suggesting is vital to the project, and cannot be handled as a phase two, then I would like to stop the project now so that this new addition can be properly scoped and integrated, rather than tacked on. To continue without re-scoping, may cause unforeseen problems later, which could be quite costly. However, you must understand that to stop now will affect timelines and budgets. How would you like us to proceed?”

Joe Di Stefano

Three Questions to Ask About Any New Project

Before Jim Coudal and team take on any new project, they ask themselves these three questions.

  1. Can we make money from it? We’re a going business. We have mortgages to pay. We have tuitions to pay for our kids. We’re not ashamed of making money.
  2. Are we gonna be proud of it when we’re done? There’s nothing that will break your heart faster than working three months on a project and then, when it’s all done, you’ve sold your soul and compromised and you don’t even want anybody to see it.
  3. Have we learned something new? That allows us to continue to grow in the skills that we have. It allows us to be better filmmakers and writers and coders and art directors. And it keeps things interesting.

Via SVN

The Rules of Free Commerce Haven’t Changed

I feel buffeted at the moment, rising and falling at the whim of ambition, understanding, a sense of meaning, a sense of meaningless, vanity, ego, a desire to create, a desire to be recognized, a sense of bigness, a sense of smallness…

I have my “industry.” I’m a blogger. I have blogger friends and read blogger books and study blogger businesses and want to build a successful blogger business.

I know, pretty cool, right?

All this blogger business thinking has been spinning up an engine in me that’s ready to power something. I’m thinking big and thinking I’m special and thinking about how to become more special and thinking and thinking…

I have this one friend who had some success with an eBook. He’s a family guy. He thinks blogger thoughts too, but they’re tempered a bit more than mine. He’s one of these classic nerd bloggers, the best kind. The kind that had an audience long before there was a business plan. Love those guys.

He tried not to be too ambitious. I think his reality is such that he can’t; you can only get so far away from home. I resonate with that.

Side Note: this friend doesn’t understand someone having the goal of travelling around with a laptop and running a business teaching people how to travel around with a laptop. “Congratulations, you’re a narcissist,” he says. I kind of want to tattoo that on the back of my hand.

I have this other friend who wrote some books and got super famous in a Christian subculture. They were good books. I have all of them. One of them is signed. Deal with it.

This other friend thinks real big. He’s the kind of guy that get’s asked to lead the intro to the Democratic National Convention. He says I should pay attention to people like Benjamin Franklin and Thomas Jefferson instead of people like Tim Ferriss and Seth Godin.

He’s ambitious and thinks big, but there’s a humanness to it. It’s a weird balance and I’m not quite sure what the deal is with it, but I sense there’s a good path down that way.

This guy wrote a simple post recently. He nailed it. And at the end of the post he lists off, in very simple terms, the rules of business. He says they haven’t changed. I think he’s right.

I think there’s something about these two guys, something in the way they’re looking at their thing, some sort of signpost for me. A way through this ambition/meaning/bigness/smallness. Their stories seem to ask me, “why are you thinking about that?”

Anyways, here’s those rules.


The rules of commerce:

  1. Identify something people need or want.
  2. Create that thing and create it well.
  3. Sell that thing at a competitive price.
  4. Clearly communicate what that thing is.
  5. Give half the money you make to the government.
  6. Give a percentage of your money to causes that need your money.
  7. Love your spouse and your children, because in the end little else will matter. They don’t care about your money.

Don Miller on “Changing the Rules”

“I know you read a Seth Godin book convincing you you could be a billionaire by creating a tribe. And you read a Timothy Ferris book convincing you you could work four hours a week and be rich. Guess what? Both of those guys work as tirelessly as depression-era farmers. They do this because the laws of the universe haven’t changed. You have to work to eat. And you have to work hard.

And let me add this. Sell out. Scrub a toilet. Nothing is beneath you.

I’ve watched scores of twenty-somethings quit their jobs and start businesses based on books written by people who sell fantasies. These writers tell one story about a guy who bought an island because he created some online business and convinced people they could do it too.

Don’t be fooled. The chances of that happening to you are about the same as winning the lottery. Writers are making millions by convincing people they can win the lottery too.”

Donald Miller

Henry Rollins on The Iron

The Iron never lies to you. You can walk outside and listen to all kinds of talk, get told that you’re a god or a total bastard. The Iron will always kick you the real deal. The Iron is the great reference point, the all-knowing perspective giver. Always there like a beacon in the pitch black. I have found the Iron to be my greatest friend. It never freaks out on me, never runs.

Friends may come and go. But two hundred pounds is always two hundred pounds.”

Henry Rollins


I continue to come back to this article and the idea that the things which are hard for us are teaching us — like a sensei.

I’ve experienced this most with lifting weights, so I’ll stick to that illustration, but I’ve also sensed it with growing a business, raising a son and staying married.

When I approach the weight asking, “what lessons do you have for me today?” my whole mental posture changes. It’s no longer a contest, no longer about my ego, a thing for me to win or lose. It’s a relationship between a master and an apprentice.

When I’m in that posture the workout is better, it works out more of me. Also, I do less stupid shit.

In business it helps me not be crushed by a piece of bad news, gets me in the posture where my reaction is more, “ok, what do we learn from this and what’s the right thing to do?” and less, “fuck, my ideas are shit, the world is shit, i’m going to die alone and I have a small penis.”

If you haven’t read this full article from Henry Rollins, I highly recommend it: The Iron & The Soul by Henry Rollins.