Kevin Rapp: How to Be A Cynical Optimist (#31)

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Today I’m joined by hardware engineer and comedy writer Kevin Rapp. Kevin writes a weekly newsletter about nothing, aptly titled the “Full of Krapp newsletter.” I’m subscribed to dozens of newsletters. Kevin’s is by far one of my favorites. It’s part hysterical part informative take on the ridiculousness of modern life. Highly recommended.

We cover:

  • Comedy, what it is and why it matters
  • Kevin’s favorite comedians (and some of mine)
  • The outrageousness of outrage culture
  • People who get compared to Hitler who shouldn’t be compared to Hitler
  • Writing advice
  • Glue, horses, and how they’re (not) related
  • Criticism and how nobody avoids it (even Viktor Frankl)
  • The draconian California lockdown curfew
  • And loads more.

Please enjoy!

Listen on Spotify | Listen on iTunes | Watch on YouTube | Trailer

Every Sunday, I write a weekly newsletter full of advice for creatives, plus extra goodies like drafts of blog posts and previews of the podcast. Sounds good? Click here to subscribe and get the next issue delivered straight to your inbox on Sunday.

PS: Does The Penguin Latte Podcast remind you of the excitement of fresh presents on Christmas morning? If so, please consider leaving a review on Apple Podcasts/iTunes. It takes all of 60 seconds (or 120 seconds if you’re feeling extra spicy). By leaving a review, you’re making the podcast 1% better. So, if 500 of you leave reviews, the podcast gets 500% better (if I have my math right). Plus, I love reading all of your juicy comments. Thanks so much!

Insight follows movement

Sitting by, waiting for insight to strike – that’s rarely a reliable strategy.

Insight follows movement. Insight comes when we pick the pen, put down our excuses, and begin to work. Even if the first three drafts suck (they usually do). And even if we fail to meet our expectations (we usually do).

It’s rare for anything I make to turn out as great as I wanted it to. But I can at least try to meet my expectations. I can at least try to put in the reps.

Because that’s all that matters.

Repetition. Repetition. Repetition.

Start moving. Start seeing. Start creating.

Personal newsletters are the new social media (and that’s a good thing)

I’m not on social media much these days. Not for the typical reasons, at least. Whenever I’m on Twitter, it’s usually because I’m promoting the podcast and videos. And if you see me on Facebook and LinkedIn, it’s not me. I ghost-post the blogs on Facebook and LinkedIn straight from WordPress.

But let’s consider Facebook. Facebook is for connecting with friends and family. It’s to see what everyone’s up to. But what it’s really about is to see what everyone thinks they should be up to. You know, staying on top of politics, frappuccinos, the perfect vacation, complaints about work, all that fun stuff.

Facebook is like fast food food photography. A photograph of a quarter pounder makes the burger look as sexy as Aldous Huxley, but in reality, it’s about as ugly as Arthur Schopenhauer. In other words, your life will never be as exciting as it appears on Facebook. The opposite is true: your life is not as depressing as you make it out to be on Facebook.

Anyways, newsletters. So, there’s all sorts of newsletters. We have personal newsletters, brand newsletters, corporate newsletters, my newsletter. Let’s look at the first one.

A personal newsletter is like a Facebook post worth reading. It’s generous because nobody asked the writer to share it. It’s high quality because the writer has a deadline. And it’s lacking all the stuff that makes Facebook a two-way attention vortex: no distracting sidebar, no noise, no signaling, no showing off, no hiding behind the mask of filters.

People who write personal newsletters hold themselves to a standard. Their goal? To get better at writing. Which means that they want to get better at thinking. (Facebook would be much better if its users applied this mindset.)

I learn more about someone’s current state-of-mind than I ever could from the typical Facebook post. All because of the generosity of the writer, the high bar of a deadline, and the missing cacophony of sidebars and infinite scroll.

A great personal newsletter writer considers only this question: what am I noticing?

Here’s some personal newsletters I’d recommend to anybody looking to bring some joy and curiosity to their week. All written by generous friends of mine.

Letter from A Learn-It-All — Jen Vermet’s thoughtful posts on the bravery of learning.

Thinking Out Loud — Cullin McGrath’s weekly writings on personal growth.

Quick Brown Fox — The original playground for adults. Salman Ansari connects ideas from poems, drawings, and animations.

Happy reading.

Help I’m being engaged at!

The comments section is the most under-leveraged asset.

It’s not a place to test out your new emoji keyboard.

It’s a place to say, “hey I really like what you said. Let’s take this even further.”

Did someone take time out of their day to write a comment that’s more than three words long? Return the favor.

The comments section is not a place to shortchange empathy, either. The problem isn’t “thanks for this, I needed that.” That’s fine. You said exactly what you wanted to say. The problem is, “if I respond to this, how many more followers will I get?”

Every time I write an essay as a response to a comment, I’m surprised at how surprised people get. It’s sad, actually. How many people are crying out for someone to hear, see, and work to understand? To have someone say, “I sort of get what you’re saying, but could you go further?”

The stereotype of the desperate salesperson has been replaced by the value hound. Sub-for-sub. Free subscribers. You follow me, I follow you. Oh, I see. You’re trying to engage at me, rather than with me.

Being engaged with. That’s what delights us, surprises us, makes us miss you when you’re gone.

Seen, heard, understood.

Eye contact.

The Penguin Latte Podcast #2: Cullin McGrath on Building a Community of Writers and the Nuance of Improvement

Today, I’m joined by Cullin McGrath (@Cullin). Cullin McGrath is a writer that any ambitious creative person needs to know. If you’re a fan of Ryan Holiday or James Clear, then you’ll appreciate Cullin’s insights on what it means to live a life of meaning. I recommend starting off with his newest essay, The Danger in Full-Throttle. It’s an intelligent, revealing story about Cullin’s experience with the often overlooked darkness of self-improvement.

Cullin is also building a paid community of writers at Writer’s Bloc, which I’ve had the privilege of beta-testing. It’s transformed my writing in ways I could not have imagined. I’ll post a piece that I’m working on, and within a few hours, I’ll get generous feedback and support from other aspiring writers. If you want your writing to level up (fiction or non-fiction), I highly recommend checking it out.

“You have to operate in life around something that excites you and fills you with purpose.”

Talking Points

  • What was it like at a Tony Robbin’s Seminar? (2:45)
  • How can introverts promote their work online? (7:20)
  • The pitfalls of self-improvement, the balancing act of building and decompressing (9:30)
  • How building things online has always been a part of Cullin’s life (12:30)
  • When does Cullin feel the most at ease when he’s working towards his goals? (13:40)
  • What meaningful work feels like (14:20)
  • Don’t point fingers at people who aren’t entrepreneurial (15:00)
  • What’s the future of newsletters? (17:20)
  • (19:00)
  • Doing the books instead of reading all the books (22:00)
  • Can reading fiction improve your non-fiction writing? (24:40)
  • On Ryan Holiday (27:00)
  • How message boards (remember those?) inspired Cullin’s writing (31:00)
  • How has writing for an audience changed Cullin’s thinking? (32:00)
  • Building confidence as a Creator (35:30)
  • Cullin’s transformation through writing (38:00)
  • Balancing entertainment with ambition (40:00)
  • Books that broke us (46:00)
  • Why we don’t follow GaryVee on social (51:00)
  • The benefits of being disagreeable (55:00)
  • The big questions (1:00:00)
  • Will we really be working for ourselves? (1:04:00)
  • The Future of Writer’s Bloc and the problem of scale in paid online communities (1:08:00)
  • Cullin’s message to people who are stuck (1:13:00)
  • Reading Marcus Aurelius in middle school (1:16:00)

Show Notes and Resources

Tony Robbins Seminars

(And here’s a trailer of the documentary about his seminars.)

The incredibly detailed process of writing a book when your name is Ryan Holiday.

The Four-Hour Workweek – The book that broke me.

The Third Door Book – The book that broke Cullin.


Ryan Holiday on the impact of Meditations by Marcus Aurelius

The Tao Te Ching

Everything that you need to know to succeed at this

The list is shorter than you think. It’s simply everything that you need to know to succeed at this. You can let out a sigh of relief now. “Oh! thank goodness I don’t need to read every business book published in the time it took me to finish saying this.”

It’s not every word in every self-help book.

It’s not every episode of every business podcast.

And it’s not certainty not every strategy to manage every piece of information in all those self-help books, podcasts, newsletters, and articles you’ve consumed in the last eight hours.

Many of us in the self-improvement world call ourselves minimalists. We might say that we approach life with a “less is more” attitude. And yet we’re maximalists with our information.

We have…

Books. Other people’s notes about the books (in the form of blog posts).

Podcasts. Other people’s notes about the podcasts (in the form of twitter threads).

Strategy. Content. Content creation Strategy.

Digital Data Management. Courses about Digital Data Management. Strategies about marketing our courses about Digital Data Management.

Even further, we’re neither maximal nor minimal about feeding the dog (or ourselves) since planning our Digital Data Management Course marketing strategy is more important. Dinner can wait.

The way out of this trap? Selecting. Filtering. Ignoring. Seeking the signals in the noise. Choosing a craft to practice, and then practicing it.

And the list of everything that you need to be? Much shorter, too. As short as one word.


Open to the possibility that this doesn’t apply to that. The possibility that what’s guaranteed today might not be guaranteed tomorrow. The possibility that more information is not the answer.

Derek Sivers said it best:

If more information was the answer, then we’d all be billionaires with perfect abs. — Derek Sivers

Thoughts on how to make newsletters better

Getting better at a game means getting better at thinking about how to play the game. It’s called meta-gaming. Even Monopoly can be meta-gamed.

If you’re a newsletter writer, it’s likely that you follow a lot of newsletter writers on Twitter. And so all you see is newsletter meta-game. This is the best platform. No, this platform is better. This is how you standout. No, that’s not how you standout anymore because now everyone is doing that. Newsletters aren’t dying. No, newsletters are dying and if you subscribe to my newsletter I’ll tell you why.

It’s as if all these newsletter writers are writing for other newsletter writers.

Your readers probably aren’t other newsletter writers.

To avoid the trap of newsletter meta-gaming, here’s a few simple questions.

Why should your readers keep reading your newsletter?

What would your readers say to their friends about your newsletter?

What’s cool about your readers?

What makes your readers different from their readers?

How can you be sure that your readers don’t become a commodity?

Remember your readers, and they’ll remember you. That’s all that matters.