How Low Are the Low Points in a Startup?

“If so many startups get demoralized and fail when merely by hanging on they could get rich, you have to assume that running a startup can be demoralizing. That is certainly true. I’ve been there, and that’s why I’ve never done another startup. The low points in a startup are just unbelievably low. I bet even Google had moments where things seemed hopeless.

Knowing that should help. If you know it’s going to feel terrible sometimes, then when it feels terrible you won’t think “ouch, this feels terrible, I give up.” It feels that way for everyone. And if you just hang on, things will probably get better. The metaphor people use to describe the way a startup feels is at least a roller coaster and not drowning. You don’t just sink and sink; there are ups after the downs.”

Paul Graham


I’ll keep coming back to this.

Just knowing this sentiment exists, that there’s a smart person who’s been there and who continues to live in the startup world that has this perspective, that’s enough to feel like you’re not alone in the toughness.

Because the problem for me with the toughness of startups has been the uncertainty.

Am I doing this right? I’m not. I must not be. I’m lost. Who do I think I am? I should have never been a part of this. These things never work out.

The splinter of doubt wedges itself in, getting deeper and deeper, all the while making the excuses heavier and heavier.

The only true armor we have is knowing it will come. Thanks, Paul.

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

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

The Function of the Majority of Your Art

“The function of the overwhelming majority of your artwork is simply to teach you how to make the small fraction of your artwork that soars.”

Art & Fear


This is from a book about making art. I don’t know who these authors are but they really nailed something for me.

I’ll only make a few pieces of truly good stuff over the course of my life.

That’s the reality.

I could break my head over trying to epic-ize everything I make. I could reach for celebrity and recognition through lots of truly great things, getting broody, moody and horribly not fun in the process.

Or I can make this thing the best I can right now. It’s not me. I’m not it. There’s some sort of exchange going on between me and it, but neither of us are each other. So let’s keep it casual.

Because any sane person knows that the best you can do right now is the best you can do right now.

This is embarrassing to admit, but when I read this I first thought about my tweets.

Before pushing “publish” on a tweet I typically have a moment of, “c’mon. Nobody cares about this. This isn’t funny. Make something funny and post that. Is this the kind of thing Merlin would post?”

But I’ve been wondering recently if I won’t look back and wish I shared more. If 20 years from now I’ll read through the archives and wished I just tried more stuff.

This quote hits me with reality, balances me. I might make a few good tweets over the course of my life. The shitty ones will help me get there.

I mean, these are fucking tweets we’re talking about.

Oh, and art. We’re also talking about art. Which is kinda like business to me. So that too.