The Chase Jarvis Live show

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Back in October I was in San Francisco to record an episode of the Chase Jarvis Live show. We talked for nearly two hours about work, life, building calm (and crazy) companies, FOMO + JOMO, philosophy, the downsides of real-time communication tech, not setting goals, saying no, our new book “It Doesn’t Have to Be Crazy at Work”, etc. Loads of stuff, a really fun conversation.

Here’s the full YouTube video:

If you prefer audio-only, you can find the episode on Apple Podcasts, Stitcher, Google Play, Spotify, or wherever you listen to podcasts.

Big thanks to Chase for having me on, and for being such a kind host. He also had David on a while back — well worth watching that one as well.

We hope you enjoy!

Why scrap scrappy?

For the last decade or so, I’ve been on a number of boards, consulted with a number of entrepreneurs, and have been both formally and informally involved in helping a number of young companies find their way.

Many young companies I’ve seen have one thing in common: They can’t wait to grow up. They desperately want to be taken seriously by others. They want to be perceived as sophisticated, as having it all figured out.

This is where they begin to get into trouble. As they technically begin to be able to do more things, it’s the things they can no longer do that turn out to be the big losses.

Take company size, for example. One way to be taken seriously is to hire more people. As a whole, bigger companies are taken more seriously than small companies. Thing is, small has major practical advantages over large. Small companies can do both small and big things. Big companies can not do small things. Once you get to a certain size, you can no longer do the small things. When you’re big, every initiative turns big, like it or not. Except the small things are often all that’s necessary.

Take “systems”, for example. I’ve seen a number of small companies jump into big sophisticated content management, inventory management, e-commerce management platforms. Buying into something the big guys use helps a small company feel like they’ve arrived. Now they’re ready to scale! But now all the sudden they can no longer do the things they need to do. Trying a quick idea they used to be able to just whip up becomes a wrestling match with the new system that prefers you do things the more complicated way. Now “let’s just try that” becomes “when can we schedule a time to figure out how we can try that?”

The other thing that’s lost in transition from small to big are instincts. I’ve seen companies paralyzed by ideas they can’t seem to implement anymore. They could still do things they same way they used to, but they can’t think that way anymore. For example, a small company that would have just spent a couple hours sending out 50 hand-written emails to test a personalized selling campaign, is stuck for days or weeks trying to figure out how to get their new e-commerce platform to automate the same thing. They could still just pick the customers and write the emails by hand, but they’re forgotten how to think about doing it that way. Once you have something in place that’s supposed to be able to do that work for you, you lose flexibility, your mind and muscles atrophy. You cease to be able to be scrappy.

Scrappy is a mindset, and the skills are lossy — once they’re gone, you can never recreate them the same way again. Being scrappy is easier the smaller you are, the younger you are, and the fewer options you have. Hang on to it for as long as possible! Don’t be in a rush to abandon such critical survival instincts.

It happens to all growing companies. We’ve certainly lost our fair share of scrappiness as well. My suggestion: Resist the allure of large — there’s very little payback, especially if you artificially get there before you’re really ready. Be aware — and beware — of the things you give up too early and never get back.

The owner’s word weighs a ton


Be careful not to throw your weight around without knowing it.

Yesterday I was in a board meeting for a company I advise. Great group, strong business, profitable, all the good stuff. But the owner-CEO was stuck. He felt like he’d laid out a pretty clear vision and direction, but people’s priorities kept shifting. This thing was important, then all the sudden it was this other thing. Lots of bouncing around, not quite enough focus. He didn’t know what was causing it, but it turns out it was him. But how?

We dug into it. As we went, I recognized the problem.

As much as we’d like to pretend we’re just one of the crew, the owner is the owner. And when the owner makes a suggestion, that suggestion can easily become high priority. It’s rarely what the owner intends, but it’s often how it’s received. When the person who signs your check says this or that, this or that can quickly become the most important thing.

It’s like the old EF Hutton ad “When EF Hutton talks, people listen.”

So something as minor as “Are we doing enough on Instagram?” can shoot Instagram to the top of the marketing priority list. It was a mere suggestion, but now it’s a mandate. “Why would he be talking about Instagram unless he really thought Instagram was super important?”

What’s worse is when the owner finds him or herself in the weeds. Meddling too much in this problem or that problem. If that’s where they’re spending their attention, people assume it’s top priority. It may be a mere curiosity, but that’s not the impression it makes. If she’s looking over there, then we should be looking over there. The owner’s presence in a problem area can re-prioritize the organization’s plate without intending to.

And that’s just one example. But owners like to lob ideas all over the organization, and often many at the same time. You can think of them as tiny pebbles being tossed into a pool. When the pebble hits the surface, it radiates small waves. If you’re in that pool, you’ll be affected. A splash over here sends waves this way, a drop over there sends them in another direction. Before you know it, the stillness is broken up by intersecting rings of water. It can get chaotic pretty quickly. And after a while, it’s unclear where all the action started, it’s hard to trace. It’s just busy, churning water. It takes a long time to settle it back down again.

So if you own the place, be careful what you say and when you say it. Most of the time your word carries more weight than you wish. Reserve that weight for when it’s really necessary.

Can You Sell Water? Part 2

Abraham Celio and Maria Mendez own Yolis Tamales on Chicago’s Southwest Side.

Some of the tech industry’s most vaunted companies revel in their origins as mavericks or rule-breakers, having flouted regulations in the name of disruption. That kind of risk-taking is celebrated in Silicon Valley but punished in other places, most notably minority communities.

In this episode of the Rework podcast: A legal advocate for low-income entrepreneurs talks about the hurdles her clients face, and a husband-and-wife team of street food vendors share what they’ve learned making the transition from the informal to the formal economy.

Can You Sell Water?


Selling is a core skill. You have to know how to sell, whether it’s a product, an idea, or yourself. In 2012, Basecamp CEO Jason Fried saw the results of a bottled water-selling challenge at Techstars Chicago, a bootcamp program for startups. That one-day competition is the starting point for a conversation that includes the art of negotiation, Jason’s experiences selling knives, tennis rackets, and software; and other adventures in business.

Sell Your By-products

It’s the debut of the Rework podcast!

Welcome to the first episode of Rework! This podcast is based on Jason Fried and DHH’s 2010 best-selling business book, which was itself based on years of blogging. So what better way to kick off this show than talking about by-products? In this episode, Jason explains how Basecamp’s ideas have been packaged as blog posts, workshops, and books. We also visit J.H. Keeso & Sons Ltd., a 145-year-old sawmill in Ontario, Canada to see how this family-owned business sells its physical by-products.

We’ll be bringing you new episodes every other Tuesday, so be sure to subscribe via Apple Podcasts, Google Play Music, RadioPublic, or wherever you listen. We’ll take you behind the scenes at Basecamp and bring you stories of other businesses—startups, established companies, makers of physical products, brick-and-mortar stores, and more. Follow along and let us know what you think!

“Whatever it takes”

How often have you heard that one? “Whatever it takes”.

It’s an iceberg. Steer clear.

What starts out as an innocent turn of words, is actually a veiled attack on reasonable expectations. And when expectations aren’t reasonable, all bets are off. And when all bets are off, you’re usually the loser.

Whatever it takes means you’ll probably be working at 10pm on Wednesday.

Whatever it takes means whenever I need you you better be available.

Whatever it takes means sloppy work in service of just delivering something.

Whatever it takes means the absence of no, and once no’s out the door you’ve given up one of the most powerful tools you have.

Whatever it takes means if you won’t do it, I’ll find someone else who will [endure the abuse].

Whatever it takes is a threat to your friends and family time.

Whatever it takes is doing something “at all costs”. When you stop discussing costs you’re in deep.

Whatever it takes is a slippery slope.

Whatever it takes is the opposite of calm, paced, and fair.

Certainly there are exceptions, but whatever it takes is rarely as nice as it sounds. Be leery, be weary, be aware. Remember what’s behind the veil.

Why are some people successful over and over and over again?

Star Trek cast with J.J. Abrams — pic by Eva Rinaldi

Work hard and…

Star Trek Beyond is doing great at the box office, but some critics aren’t impressed. Owen Gleiberman at Variety has seen better:

Where is there left for the series to boldly go? I don’t believe that “Star Trek Beyond” is the answer. Justin Lin’s new film delivers in terms of action, but it’s a deluxe place-holder, earthbound in spirit and a bit leaden, all too rooted in ancient interplanetary tropes. It has visual extravagance (especially in the vertiginous climax), as well as tasty bits and pieces of the characters’ personalities, but it rarely gets both things together in the same place, and that’s a serious setback.

Another thing caught my eye about Owen’s review. Though he was a fan of J.J. Abrams first and second effort at the rebooted franchise, he had this to say about Abrams and his second Trek movie Into the Darkness:

By the time of his second “Star Trek” movie, “Star Trek Into Darkness,” it was more or less evident that Abrams was auditioning for “Star Wars.” He wanted to captain that franchise, and he earned the promotion by proving himself to be a master of retrofitted nostalgia.

Is that even true? Did Abrams use Star Trek as a stepping stone to Star Wars? After all Abrams wasn’t even a fan of Star Trek growing up, but he sure was a Star Wars fan.

Turns out this doesn’t seem true at all. Abrams turned down an offer from Disney to do Star Wars exactly because of Star Trek. From Neil Daniel’s biography of Abrams:

There were the very early conversations and I quickly said that because of my loyalty to Star Trek, and also just being a fan, I wouldn’t even want to be involved in the next version of those things. I declined any involvement very early on. I’d rather be in the audience not knowing what was coming, rather than being involved in the minutiae of making them.

Abrams finally considered Disney’s persistent offer only after Into the Darkness was done with production.

So what? Well, I think this shows us some interesting behavior Abrams exhibits about work and perhaps why he’s so successful over and over again.



On July 20, 1969, man stepped on the moon. That feat was an incredible collaboration of ideas and thinking from the most brilliant minds on earth. One of the key groups was Nasa’s JPL (Jet Propulsion Laboratory). The JPL wasn’t always Nasa’s. The JPL goes back to 1936 when they were the Guggenheim Aeronautical Laboratory and were inventing and testing rocket technology for the military.

Given JPL’s age and history, in the 1990s, many of the engineers that helped put man on the moon were retiring. A new generation of JPL engineers were replacing them.

One problem. Those new engineers weren’t solving problems as well as the old ones. Sure they were smart. Came from the best schools. Knew their stuff. But they often weren’t able to complete difficult and complex projects all the way to practical execution.

What happened? And what could they do to fix it.

They discovered an article by Nate Jones. Nate ran a machine shop of engineers who worked on race cars and tires. He saw the same thing the JPL was seeing. The new engineers just weren’t problem solving as well. So he dug into interviewing folks and discovered a correlation, one that the JPL confirmed.

The older more senior engineers who were good at problem solving also happened to have grown up building gadgets, taking apart things, making their own soap box race cars, and just generally “playing” at being engineers before they were ever technically trained as engineers. The new engineers, who weren’t up to snuff, didn’t. They knew theory from text books, and learned all the things well that they needed to learn. But they didn’t grow up playing as engineers or embracing play even as adults.

This is just one anecdote from a wonderful book called Play by Stuart Brown, M.D. that explores powerful research and findings on how important play is for realizing our full potential. When we don’t play and everything is just work, we don’t grow like we should. Play is insanely important in the animal kingdom and through our own childhood. But we forget, it doesn’t stop being important. Adults need it too.


Let’s look a little closer at J.J. Abrams.

I think the reason Owen Gleiberman thinks Abrams was auditioning is that Abrams sort of is. But unintentionally. He’s playing. He’s taking something he did before and pushing it a little further. Kids play the same way. They take an ability and see if they can push it a little differently. They learn to swim and then try to swim backwards.

Abrams is the well known creator of the popular TV show Alias. But many don’t realize that Abrams was also the creator of a TV show before Alias called Felicity, which focused on college relationships and drama. Alias was Abrams playing:

What if Felicity were a spy

When you look into Abrams past you see he was playing at being a movie maker even as a child. He’d shoot Super 8 films and create special effects like a “lighting bolt” monster by scratching the actual film frame by frame. (Turns out Spielberg was shooting Super 8 films too as a kid.)

And Abrams never lost that sense of play.

In fairness, I don’t think I’ve stopped writing dodgy screenplays. When I was in college I wrote around ten screenplays. Some were about young people going through crazy adventures. Some were more offbeat — there was always an odd love story at the core of it. It was the beginning of wanting to try to figure out how to write a screenplay. There’s never a moment you go from being an amateur writer doing the best you can to being a professional writer who does great — you’re always doing the same thing but if you’re lucky at some point, you make a living from it. I don’t feel any different when I sit down to write something today than I did back in college. It still starts with: “What if I did this?”’

He doesn’t feel any different from when he was a kid just playing. I think that’s a huge reason Abrams has been able to get to where he is and why he remains so prolific even after strings of failures.

I think it’s not about when your time is and isn’t, and people have ups and downs. I think you can’t predict anything. You don’t know what anyone’s going to say.

“You can’t predict anything.” According to Brown one of the key ingredients to making something play is its apparent purposelessness. I think Abrams admitting that he can’t predict what his work will do allows him to still treat his projects as play even when it’s now his job.

Don’t get me wrong. You can’t just play and become the success J.J. Abrams is. Plenty of people used a Super 8 as a kid and aren’t the next Spielberg. But I think most successful people, if you look closely, you’ll see they’ve figured out how to turn work into play. And it’s an important part of getting through all the stuff in our way.


I spend time trying to teach my daughter the importance of working hard and being smart. As she goes to sleep I’ll tell her how proud I am of her that she’s learning so much and working so hard to figure things out. I praise her curiosity and how much time she spends asking us questions.

My wife was pretty shocked when my daughter then was giving our pet cat, Tela, advice randomly one day. She told Tela, “You need to work hard and…”

Tela definitely needs to get off the table. But yes, my daughter just taught me a lesson that I often forget. Work hard and play.

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