I went to Denver a few weeks ago to meet up with internet friends.

I’m happy to report none of them were murderers, I partied and did pilates, and wrote this article about it. One of those good non-murderer friends includes Adam Saks: a Googler, writer, and one of my Wellness Guild cofounders.

Throughout the conference, we talked about topics ranging from potential articles to brand sponsors for our wellness & yoga retreat this summer. It was our first time meeting IRL, but we had a great time and got shit done.

One day, we went to lunch with Adam’s San Francisco friend Paul and Paul’s friend David. Paul is an investor at a web3 venture capital firm and David runs his own investment firm. They are both in their early twenties, funny as hell, and treated us to endless Brazilian steak.

Paul and David were blunt with one another and if one thought an idea was shitty, he felt no qualms about saying so. For example, we originally sat down at a cheap diner, but after Paul and David said the food looked unhealthy, we left to go to the Brazilian steakhouse: an endless protein buffet.

After Adam and I split from Paul and David, Adam mentioned a phrase I’d never heard: intellectual sparring. He said that as cofounders, writers, and friends, we need that; we need to be honest and blunt with one another about the merit of ideas.

Reflecting now, I’ve realized I’ve been intellectually sparring with people my entire life, but never had a phrase for it.

A few examples from this week alone:

1. Before I sent out my last article Mental Model Mixtape, I sent a draft over to 2 of my friends and asked them which of the original 5 ideas were the weakest.

2. I called my longtime friend Shane Levine and asked his thoughts on a business idea last night1.

3. I called Jacob Peters (cofounder of Launch House) and asked him about his thoughts on my idea regarding raising funds for Wellness Guild.

After thinking about this mental model for the last few weeks, I’ve come up with a few ideas regarding who to spar with and how to spar effectively.

Who to Spar With:

Spar with someone who has domain expertise

You can’t intellectually spar with everyone. Some people’s egos are too large/fragile and others don’t know enough to know they don’t know enough.

You need to think about where the person’s expertise lies. If you need advice on women, you don’t go to the friend who hasn’t been laid since Vietnam.

I called Shane because my idea revolves around streetwear and he worked at StockX for several years. I called Jacob because his startup Launch House raised $12 million from Andreessen Horowitz last month.

Spar with someone who is brutally honest.

Intellectually sparring at first is quite uncomfortable.

Initially, when someone attacked one of my ideas, my instinct was to get defensive. It felt like they were attacking me. Now, I try to detach myself from the idea and look at the idea’s merit objectively.

If you’ve been around tech long enough, you’ve heard of first principles thinking: taking an idea down to the roots.

If you’re building a rocket, do you want a designer who can design a rocket’s aesthetic or an engineer who understands why rockets look the way they do? A designer will tell you where to put the fins, but an engineer will tell you why you put them there.

Obviously, it’s good for someone to have domain expertise, but a knowledgeable person can still be too “kind” to tell you the truth and risk hurting your feelings.

In the pursuit of quality writing and successful businesses, feelings need to get hurt in order for success to occur. Feelings are temporary - truth is forever.

Speaking of seeking truth, check out my podcast with Jack Rhysider, the pseudonymous host behind Darknet Diaries. He’s built the #3 tech podcast in the world by exploring the world of hackers, criminals, and spies.

Spar with someone who cares about you or your work.

Back in high school, we’d get paired into randomly chosen essay editing groups.

I was useless because I didn’t give a shit about 99% of my classmates. If a friend needed help, I was there to give my mental energy, but for everyone else, they got doodles and witty remarks.

I was making $1,000/mo. selling stickers online by senior year so preferred to focus my time and creative energy on making stickers and texting girls.

Maybe I was an asshole, but I call it mental-energy-allocation-efficient!

What I’m trying to say is don’t spar on ideas with someone who doesn’t give a fuck about you or the value of your ideas.

When I have a business idea, I called Shane because we’ve been friends since freshman year of college and are always rooting for each other.

I called Jacob because he’s an advisor for Wellness Guild and I know he cares a lot about web3 and wellness.

Sparring Tips:

Steelman, don’t strawman.

If you’ve listened to the podcast My First Million recently, you might’ve heard Sam and Shaan talk about steelmanning versus strawmanning.

Strawmanning is a popular tactic where you rip apart someone’s idea and make them look foolish. On the other hand, steelmanning is when you build up the best part of someone’s idea, but then rip it apart.

Strawmanning is far more popular and easier, but there’s a reason steelmanning is preferred by investors like Peter Thiel.

When I discuss economic philosophy with a communist friend, I used to just use humor, call him a commie, and point out that it didn’t work out for Russia.

Now, when I talk to him about it, I tell him that I agree with many of the points, but proceed to rip apart why it doesn’t work.

He’s been a lot quieter about economic philosophy since I figured out this tactic.

Don’t spar if you’re not at your best.

When I’m exhausted, hungry, in a shitty mood, or down on myself, I cancel calls where I know intellectual sparring will break out.

Sometimes, I simply do not have the mental energy to spar.

I could be completely confident in my idea, but if I’m famished, I’ll be fantasizing about Chipotle instead of being present in the conversation.

Similarly, I don’t send my articles or threads to people until they’ve gone through multiple revisions over a span of 2-3 days.

I don’t want people editing my shit before I even have a chance to edit it.

Let’s spar.

I’m looking for more sparring partners for my article drafts.

As I said above, I want people with these characteristics:

1. Domain expertise: I don’t need a proofreader or editor. I want to spar with people who understand tech culture and read frequently.

2. Brutally honest: I’m not a fan of flattery. If my idea is stupid, tell me why.

3. Give a shit: If you’re one of my readers, it’s clear you care to some degree about my work and my success.

If you think that’s you, send me a DM on Twitter.

I am also more than happy to spar. Here’s my baseball card.

1. Domain expertise: writing/reading, tech culture, web3, wellness-tech, dropping out, mental health

2. Brutally honest: I once told a woman she could leave her airplane seat when she didn’t like the smell of my beef jerky.

3. Give a shit: I have grown a bit since high school days of not giving a shit about my classmates. I’ve learned that giving a shit about people is actually a good thing and that kindness on the internet is rewarded with more kindness.

If you want to spar on any ideas or articles, let me know via Twitter.

Website: jasonlevin.io

Twitter: @iamjasonlevin

TikTok: @iamjasonlevin

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