The Story of Gumroad

Some interesting insights from a founder, Sahil Lavingia.

Reflecting on My Failure to Build a Billion-Dollar Company

Among others, this was a nice quote, “It doesn’t matter how amazing your product is, or how fast you ship features. The market you’re in will determine most of your growth.”


Adam Robinson via The Knowledge Project

Adam Robinson has a talent for simplification. He has, for example, identified the key to happiness to be connecting with others, making them happy (paraphrasing), and always expecting miracles. I love his critique of the typical self-help book as being exactly focused in the wrong place: oneself.

He has also identified a set of common causes of being stupid, paraphrased by Shane Parrish:

When it comes to overloading our cognitive brains, the seven factors are: being outside of your circle of competence, stress, rushing or urgency, fixation on an outcome, information overload, being in a group where social cohesion comes into play, and being in the presence of an “authority.” Acting alone any of these are powerful enough, but together they dramatically increase the odds you are unaware that you’ve been cognitively compromised.


Sample Asset Purchase Agreement has published a sample structure for an asset purchase agreement, tailored to lower middle market acquisitions. The intent is apparently to continue to update this. The “Middle Ground” refers to their goal of suggesting reasonable compromise positions for each term. Nice of them to release this publicly.
The Middle Ground project from

Their separate project to collect all US Intermediaries into a database will be very useful for them; that will probably stay proprietary.

If you’re not familiar with, their 2018 annual letter is a good place to start and is available on their website.

Pain/Passion Niches, Giving Away Value

Tony Robbins interviewing Eben Pagan. Good stuff about the mindset of striving to get the worse side of a deal. For example creating a market by giving away some value, such as Chapter One of a course. A mindset of scarcity thinks “how can I get $1 from a million people.” A mindset of abundance thinks “how can I give $100 of value to a million people (and charge them $10)”.
The Pain/Passion niche discussion is about half way through, and talks about some propositions being of more emotional urgency than others, and how humans are most motivated by moving away from pain. And some pains have higher urgency than others. Accountants are more common than tax strategists.
1. “There’s gotta be pain and urgency, or irrational emotion”.
2. “Is my prospect proactively looking for solutions?”
Talking people into wanting what you are selling is hard work, and doesn’t really work well.
3. Does your prospect have few, or ideally zero, perceived options? Within a niche there will be a need that is unfulfilled and one’s business can be the only option. If you can get 3 yeses, it’s probably a good product.

Build a “list”. Customer list to build relationships and lifetime values. Has 10X’d his business. Treat them as individuals. Script out conversation with one customer. Avatars. Script out whole relationship, ie which conversations at which time. Automated emails, system manages itself.

Hiring/Firing. Hire slowly Fire quickly. Bad hires cost 8x their salary. Have a new hire send a daily update, an email including:
1. What I did today and results I got
2. Problems or challenges
3. Questions that I have for you
After 30 days you will know an incredible amount about the person.
Hire “Drivers”, who want more responsibility. Proactive, not reactive. Results orientation. Sense of personal responsibility, ownership. Also superstars want to change the world not just make more money.

Taleb at Google, Nov. 2018

In which he reveals what he left out of his book, Incerto. When there is a lot of uncertainty, there is a lot of certainty about what to do about it. That bit around 12:00:

At 39:00, there is entrepreneurial advice.

“People ask me, what should I be doing?
Start a business, take some risk, now.”
“Start a business, create jobs, do not rent seek. Do not be a rent seeker.”

At 48:00, “Don’t tell people what they should be doing, tell them what you’re doing. Deadlifting.”

Memo by the late Robert Strasser, of Nike

ht @evgimanco


  1. Our business is change
  2. We’re on offense. All the time.
  3. Perfect results count – not a perfect process.
    Break the rules; fight the law.
  4. This is as much about battle as about business.
  5. Assume nothing.
    Make sure people keep their promises.
    Push yourselves, push others.
    Stretch the possible
  6. Live off the land.
  7. Your job isn’t done until the job is done.
  8. Dangers:
    Personal Ambition
    Energy takers vs. energy givers
    Knowing our weaknesses
    Don’t get too many things on the platter
  9. It won’t be pretty

I believe my favorite is no. 6. I also like the consistent grammar and punctuation (except missing period on no. 1), from an earlier time. I’d love to see the original, presumably typed.

Also noteworthy is how much no. 3 conflicts with some popular current thinking about best practices. As Ben Hunt (@Epsilon Theory) says, “these principles would be almost uniformly disastrous for a financial advisor.”


Beshore on base rate analysis

Assume you’re only going to be mediocre, then explore what business and life look like if that’s true.

Omg, such a great quote! I have been struggling with the concept of “base rate analysis”, and this makes it really clear to me. More specific to the topic, he says “Picking your field is arguably more important to your success than your current skill and future capacity. In some segments of business, everyone makes lots of money and the very best do outrageously well. In other areas, even the very best often declare bankruptcy. It’s a base rate analysis.” In data science, this is called normalizing the data.

That being said, over-strategizing is a very real danger. For example, base rate analysis may lead to good business decisions, and Tyler Cohen’s “Age of Deferment” (don’t even try to be the best because it’s impossible) may be “true”, but I think there is maybe a bit more to life 🙂 .