Messy, Messy, Messy, CLEAN

My new life motto is “messy, messy, messy, CLEAN”, meaning:

Whatever you produce at first is going to suck. And so I’ve found that if I don’t give myself permission to be awful I never start anything.

This reminds me that it’s not only okay to be bad but it’s a fundamental part of the process.

I haven’t fully internalized this yet but that’s why it’s the life motto. Please feel free to remind me of it in the future.

I Don’t Know What That Means

Through college I always thought it was unacceptable to admit mid-conversation that you didn’t understand something that was being discussed.

I don’t know where this belief originated from, but I didn’t realize how deeply embedded it was in me until I discovered it was there at all:

I had a great roommate in college named Jon. Smart, fun dude. He was talking to someone in our living room, something business related, and at once point he interrupted the other person to ask/tell them “I don’t know what that means.”

So the person naturally took a moment and explained the term. No big deal, and the conversation moved on.

This was a revelation for me. Until then I didn’t realize you could just openly say “I don’t know what that means” and admit your ignorance.

I know, I know… what a crazy idea: you’re not expected to know everything!

But until you take a moment to internalize this, you don’t realize how often you’re hiding ignorance for fear of being shamed. 1

  1. To be sure, in some places where some base level of knowledge is expected it would be bad to reveal you don’t understand a basic concept. Especially if it happened multiple times.

    But if you’re generally doing a good job at work and contributing, I say you have carte blanche in asking for clarifications.

    It’s also possible you work in an organization or an industry where ignorance is perceived as weakness. If that’s okay with you, great, but if you’d prefer to work somewhere where people can ask questions openly then get the hell out of there. Life is too short.

The 1st Question You Should Ask About Any New Company

The VC vs. bootstrapping debate is the most boring online topic ever invented. Both options are 100% valid because obviously everyone should take their own path.

The important distinction that no one talks about but that actually matters is what strategies and tactics you’ll need to use depending on your ambitions.

“How ambitious are you?”

This should go without saying but no one explicitly says it: you’re going to do very different things if you’re aiming to be Facebook versus Basecamp.

On one hand, some businesses aren’t possible if your ambitions aren’t big enough. Network-based businesses likes Facebook and Uber are good examples of this.

So when someone comes to me with an app idea requires 100 million+ users to be successful, it’s a distraction to talk about whether it’s a “good idea” unless you know what the founder is aiming for.

And on the other hand, some typical startup advice can be very damaging to smaller businesses. For example, trying to grow at all costs.

This is especially important whenever you’re reading so-called business advice online.

Andreessen Horowitz and Y Combinator have awesome info about doing a startup. But if you’re not trying to raise venture capital a lot of it will be irrelevant at best and harmful at worst.1

Make sure you know what you’re looking for a in a business before you listen to advice, and make sure you know what a founder is looking for before you give any advice.


  1. And for god’s sake this isn’t a critique of venture capital as I publish on my venture-funded WordPress blog via my venture-funded MacBook Pro. If only more of us could be as ambitious as Elon Musk and co.

Great Thoughts Time

I read Richard Hamming’s You and Your Research again yesterday. Highly recommend if you’re ambitious and trying to do something significant.

One of the things he did in his career as a researcher was taking every Friday afternoon to have “Great Thoughts Time”. After lunch him and his colleagues would get together and just talk about the biggest ideas they could think of.

No wrong answers, no “whoa that’s too crazy”… just a blank whiteboard of space to think and brainstorm and look to the future.

I’m going to try this as a thing on Twitter today. I’ll pick a topic and then anyone can add their own ideas with the hashtag #GreatThoughtsTime.

If this gets any traction I’ll try it again next week with a different topic.

Why Do People Give Their Money to Tony Robbins?

I’m going to go out on a limb and assume that the vast majority of people who make a purchase from Tony don’t materially improve their lives.

But this isn’t a critique of Robbins per se.

Sure, what he ostensibly says he does (i.e. “improve people’s lives) isn’t true.

But a much more interesting question is what’s the value being provided.

He’s the creator and king of an entire category of business. People get something out of his products. What is it?

A few possibilities:

1. He trades status. He’s coached some big names over the years, some of whom are willing to give public endorsements. When you’re in the self-improvement world and quality is almost impossible to predict, how do you show you’re worth it? By pointing at powerful names and said “I helped make them.”

2. People want an experience, not self improvement. Something like a secular religious revival experience. I could see many of Tony’s events working here. Momentarily you feel like you’re part of something bigger than yourself, you feel like your life has direction and purpose, etc. 1

3. He describes, understands, and empathizes with people’s problems better than almost anyone. This is Ramit Sethi’s true skill, but focused only on millenials. Maybe Tony does the same but focused much more broadly. Basically any interview he does starts with him describing people’s life problems. Sure that’s good sales in general, but maybe he connects better than most.

4. The dude’s just physically huge, and humans tend to follow bigger humans. (Shout out to my friend Derek Andersen for this idea.) 2

There’s a million coaches online selling personal services and courses. Why buy from Tony when you could get much more individualized attention and custom work done from somebody else?

  1. Though depending on your definition of religion, Tony’s following could probably qualify.

  2. Simple but “this explains everything” ideas are fun. Not because they’re necessarily right, but because the fact that it could be reveals something else about us.

Twitch for Sports Announcing

ESPN et al. should create a video feed that doesn’t have any announcers.

They can keep the exact same video as currently broadcasted (including on-screen visuals, game sounds, and ads) but they should 1) allow anyone (“hosts”) to broadcast their own audio over that video, and 2) allow anyone else to watch.

This would lead to all sorts of more creative and interesting announcing, in the same way YouTube has created content genres that didn’t previously exist. 1

I believe this makes sense strategically for ESPN since almost anything that brings more attention to their events is valuable to them.2


  1. Eventually they could go further: create tools (like Vidpresso for Facebook) so that hosts can use all the camera streams to create their own broadcast and on-screen visuals.

  2. I could see a problem where the top hosts command too much attention and then are able to negotiate against ESPN. But it’d probably end up more like YouTube: top hosts complaining loudly and together to get slightly better deals, but ultimately not owning enough attention of the platform individually to make a difference.

Text Creates Hate

There’s more than a few people on Twitter who I cannot stand.

I block them not because they ever interact with me but because I don’t even want to see their tweets being retweeted.

But: when I listen to these same people’s podcast… I kinda like them. They seem interesting and even fun! Look, another fun human being!

I get to hear their voice and personality and more nuance to their argument. I get to know them better.

And meeting in person just takes that to an even higher level.

So here’s my hypothesis: text is a horrible way to communicate, in the most fundamental definition of the word.

You lose the humanity of someone when you read their words. So much of relating to someone’s argument comes from seeing and hearing the individual.1

Just a reminder today as everyone freaks out about politics, and for life in general.

Hey there that’s me we’re all humans

  1. My hot take to fixing Twitter is making it have a baby with Snapchat: the feed and the 140 characters stays the same, except to post anything you have to take a picture of yourself first and include it with the post

The Agonizing Frustration of Trying to Make Daily Progress

Learning a foreign language is really weird: you can move to Mexico and study Spanish for 10 hours a day, but day-to-day you never feel like you’re making any progress.

And so you start to doubt yourself:

“Maybe I’m not good at learning new languages”

“Maybe Spanish is too hard for me”

“Should I go home?”

But you have good friends who convince you to keep at it and so every day you keep practicing and studying and doing the work.

And some 6 months later you meet another local for the 1st time, and when you tell them you’re from los estados unidos they act surprised and follow up with “oh, but are your parents Mexican?” because you speak Spanish so well that they honestly thought you were one of them.

You’re surprised because of course “you suck at Spanish” and every day still feels like a struggle and yet when you finally picked up head up from studying and looked around someone points out that you’re fluent.

This happened to me.

I imagine something similar for small businesses.

Every day is difficult. You get as much done as you can, but you always feel like you’re struggling and there’s far too many fires to put out.

At the end of every day you look at your half-completed checklist and wonder whether you even accomplished anything. Was the company getting better? It sure doesn’t feel like it…

“Maybe I’m not good at starting a business”

“Maybe this is too hard for me”

“Should I go do something else?”

But you do this long enough, day in day out, and suddenly you look up and you have 20 employees and millions in revenue and oh my god people even want to interview you on a stage in front of an audience now.

On what day precisely did you “make progress”? Was it on July 29th? Maybe that Saturday you did a bunch of extra work from home?

The point I’m supposed to make in this part of the narrative is that “no one sees the day-to-day grind of the company that’s worked for 10 years” which, okay fine, is also true.

But that’s only half of what’s interesting.

The far more useful perspective IMO is from the people inside the company: what did it feel like on a day-to-day basis all those years of working?

Daily progress is so slow that you do not feel it. And since anything worth doing takes a long time this presents a problem.

Every day you have to work without feeling like you’re moving the ball forward.1

And this isn’t just about work – it applies to every big part of life: good health, relationships, children.

So it’s important to remember that day-to-day progress is an act of faith.

It means working on something today having hope that your product/team/company or whatever will turn into something real in the future.2

It’s the consistency in exercising that faith that matters… and then many years later you can look up and realize how far you’ve come, and enjoy the fruits of your labors.

  1. Some people will start the next VC rocketship and grow crazy from day 1 and every day will feel like progress. Alas, that person will not be me or you, dear reader.

  2. That’s why if you’re at a really successful company this isn’t as big a deal; you already have evidence that your work will contribute to some larger outcome, so the leap of faith required to pump out your daily work is much smaller.

Basecamp’s Employee Handbook

Basecamp (formerly 37Signals) publicly released their internal employee handbook today.

You can see it here.

No big surprises if you know the company, but a few things I thought were interesting:

  • They’re very explicit and even demanding about side projects. They don’t want their employees doing much work outside of Basecamp.
  • The employee perks look great. E.g. $100/month for a massage, $1,000/year for continuing education, $100/month for a gym membership or equivalent, $1,000/year to contribute to a CSA membership (Community Supported Agriculture), they’ll match any charitable contributions you make up to $2,000/year, $1000 every 3 years to set up your home office
  • They explicitly want to make Basecamp a feasible place for a long-term career
  • They pay in the top 5% at Chicago salary levels, regardless of where an employee lives. They don’t do bonuses, and since the 5% benchmark data includes bonuses Basecamp just increases the salaries
  • Strict rules about traveling internationally: they have a long, detailed checklist to make sure you delete all company data off your devices before crossing the US boarder. It looks like a huge PITA (which is the USA’s fault, not Basecamp’s 🙁 )

Beware the Disease of Self-Righteousness

So a Juicero ad pops up on my Facebook feed…

Quick recap: Juicero raised $110 million to make a machine that, apparently, can be easily replaced by just using your hand. It’s pretty ridiculous and I’d ask questions if I were an investor (duh), but AFAWK there’s nothing legal or morally wrong here.

But then I decide to look at the top comment on that Facebook ad…

A negative comment with plenty of likes…

And then I kept scrolling.

Lots of people pounding their chests and stomping on Juicero’s future grave.

This attitude drives me crazy and it should seriously bother you, too.

What do people have to gain by leaving these comments on a random Facebook ad…

  • They get to dance on the grave of somebody who failed?
  • They get to show that they know what’s being talked about in pop culture?
  • They get to display how smart and quick witted they are?
  • They get that sweet FB Like karma?

None of the comments contain new information.

It’s all purely ego. 

This is like 2nd grade level stuff: mocking others to make you feel better about yourself.

Nothing about the person’s physical state changes. They’re not making money or getting healthier or anything like that. They’re merely tweaking their state of mind at the expense of others.

Self-righteousness only reveals weakness.

This of course happens ALL THE TIME everywhere you look online today. Everyone is guilty eventually.1

Best case scenario this is a severe lack of self-awareness and worst case people feel actual joy by doing these things. As usual the reality is somewhere in the middle.

If you’re ever celebrating or even enjoying someone’s failure please stop for a second and reconsider. At least ask yourself why you feel the urge to say anything negative at all. What does that say about you?

  1. Hell, I might be slightly guilty for even writing this article.