Give it five minutes

I used to be a hothead. Whenever anyone said anything, I’d think of a way to disagree. I’d push back hard if something didn’t fit my world-view.

It’s like I had to be first with an opinion — as if being first meant something. But what it really meant was that I wasn’t thinking hard enough about the problem. The faster you react, the less you think. Not always, but often.

It’s easy to talk about knee jerk reactions as if they are things that only other people have. You have them too. If your neighbor isn’t immune, neither are you.

Keep reading “Give it five minutes”

Can old world be more modern than new school?

I’ve got two machines on me.

One’s strapped to my left wrist. The other lives in my pocket.

The one on my wrist can tell me the time (precisely in 12 hour format, roughly in 24), the day of the week, the month of the year, which year of the leap year cycle we’re in, and the current moon phase. But that’s its limit. There’s no software, only hardware. It’s programmed in springs and gears and levers and jewels.

The one in my pocket can tell me anything and do just about everything. It knows my voice, it responds to my touch, and it even instantly recognizes my fingerprint out of fourteen billion fingers. This machine even knows the angle, velocity, and distance it travels when I swing it around. And it always knows exactly where it is anywhere on the planet.

But sometimes I wonder which one is more modern.

The one in my pocket can do more, but only for a limited time. And then it can’t do anything. It dies unless it can drink electrons from a wall through a cable straw for some hours every day. And in a few years it’ll be outdated. In ten years it might as well be 100 years old. Is something that ages so fast ever actually modern?

And then there’s the machine on my wrist. It’s powered entirely by human movement. No batteries, no cables, no daily dependency on the outside world. As long as I’m running, it’s running. And as long as one person checks it out once a decade, it’ll be working as well in 100 years as it works today. It’s better than modern. It’s timeless — yet it keeps time.

As time goes by, my pocket will meet many machines. My wrist might too. But when I look down at the machine on my wrist today, and know that in 50 years my son will be able to look down at his wrist at the same machine ticking away the same way it ticks today. That’s a special kind of modern reserved for a special kind of machine: the wonderful mechanical wristwatch.

The Person They’ll Become

One of the biggest challenges when hiring someone is trying to envision their potential.

Sometimes someone’s a sure bet. They’re the perfect person for the perfect project at the perfect time. Their pedigree is exceptional, their portfolio is stocked with amazing work, their experience is vast, they’re a confident interview, and everything just feels right.

It happens, but that’s not how it usually works. There are very few perfect people.

Instead there’s a lot of future perfect people. People who have the potential to become the perfect person in the perfect role if just given the right opportunity.

When I hire designers, I look for future perfect people. Some people have the potential, but they haven’t had the opportunities. Their portfolios are full of mediocre work, but it’s not because they’re mediocre designers. It’s because they’ve been given mediocre opportunities.

A lot of future perfect people are stuck in current mediocre positions. They just haven’t had the chance to do their best work.

While it’s a bonus to find that perfect person today, I find more it more rewarding (for me and them) to pluck the future perfect person out of their mediocre job today. I love betting on people with potential. When they finally get that chance to do their best work, they blossom in such a special way.

And as the owner of a company, few things make me prouder than seeing someone excelling in a way that their resume/portfolio/references wouldn’t have suggested they could.

Basecamp 3: Work Can Wait

This is the first post about the upcoming major release of Basecamp 3.

We’ve been working on Basecamp 3 for over a year now, and some of the concepts can be traced back to explorations we started a couple of years ago. We’re in the home stretch and we’re excited to let it loose.


Over the next month or so I’ll be sharing some of the key ideas behind the all-new version of Basecamp, as well as screenshots, design decisions, strategic decisions, and stories of the development of the third complete ground-up rethink and redesign of Basecamp in 12 years.


The first place I want to start is one of the fundamental pillars of the new product design: Work Can Wait.

If you’ve used a modern chat, collaboration, or messaging app, you’ve probably noticed that there’s a growing expectation of being available all the time. Someone at work hits you up on a Saturday, you get the notification, and what are you supposed to do? You could ignore them, but what’s the expectation? The expectation is “if you’re reachable, you should reply.” And if you don’t reply, you’ll likely notice another message from the same tool or a tool switch to try to reach you another way. And then the pressure really mounts to reply. On a Saturday. Or at 9pm on a Wednesday. Or some other time when it’s life time, not work time.

I don’t believe tools are at fault for this — tools just do what toolmakers build them to do. But I do believe toolmakers can build tools that help you draw a line between work and life. We’ve baked these good manners into Basecamp 3 with a feature we’re calling Work Can Wait.


Like other modern messaging tools, Basecamp 3 sends notifications in-app, via push notifications on the desktop or via a native mobile app, or via email. Where they show up depends on what you’re doing and where you are, but regardless, Basecamp tries to get your attention when someone asks for your attention.

That’s fine during the work day. Basecamp 3 lets you snooze notifications any time to give you a break for a few hours, so that’s good. But what about if it’s 8pm on a Monday night? Or on a weekend? You don’t want to have to continually snooze notifications manually. And you don’t want to have to manually turn them on or off every day, at least twice a day, to keep work stuff at bay while you’re trying to stay away.

So Basecamp 3 lets you set a notifications schedule.

Set up your Work Can Wait schedule

Each person in Basecamp 3 can set up their own work schedule with their own hours. You can of course choose to to receive notifications all the time, 24/7/365, no matter what. Or, you can say Work Can Wait — only send me notifications during my work hours. Then you can set the start time and end time and also mark off which days you work.

The example above are my work hours. Monday through Friday from 8am to 6pm in my time zone.

Outside of this range, Basecamp will basically “hold my calls”. Notifications will automatically be silenced until it’s work time again. Once the clock strikes 8am, notifications will start back up again. Of course at any time I can go into the web app or native apps and check my notifications myself, but that’s me making that decision rather than software throwing stuff at me when I’m going for a walk with my son on a Saturday morning.

Notifications are ON

We also make it really easy to snooze notifications for a few hours, turn notifications off completely, or see/change your schedule quickly.

Notifications are OFF

When you click your picture at the top of the screen you’ll see your current notifications settings. In this first example, notifications are ON because I’m on a schedule from 8am — 6pm M-F. If I want to change that schedule I can just click the “change schedule…” link and switch to always on or tweak my days/hours.

And while they are on, I can quickly snooze them for 3 hours, or turn them off completely until I turn them back on.

If notifications are off, it’ll tell me they are off and then it’ll tell me why. In this example they’re off because I’m set to receive them between 10am and 6pm, and it was 9:23am when I took this screenshot.


We believe Work Can Wait is an important notion. 9pm on Friday night is not work time. 6am on Wednesday morning is not work time. It may be for you, but it’s not for me. And I don’t want it to be work time for my employees either.

Every user on Basecamp 3 starts with a default work time from 8am to 6pm in their own time zone. People are free to change it, of course, but we think it’s important to encourage Work Can Wait rather than default everyone’s notifications on 24/7/365.

We hope more products offer similar abilities to shut themselves off when work is over. “You can get ahold of me about work whenever” will eventually lead to “I don’t want to work here anymore”.

Here’s to early mornings, evenings, and weekends being free from work. Work Can Wait.

How I managed to get Tim Ferriss to advise me, launch a product to a huge audience, and take over…


You probably have no idea who Jason Allred is. Most people don’t. He’s a 35-year-old pro golfer who is far from a household name. Golf’s tough, and Jason has had more downs than ups with the game.

“At the end of 2008, Allred had lost his PGA Tour card, then failed to regain it in the qualifying tournament, leaving him nowhere to play in 2009.”

–Mike Tokito

Then he got to play in the 2010 U.S. Open. That was over five years ago. After that? Not another tour event, until all of a sudden he had a couple good tournaments in 2014. Great, right?

Not exactly. A couple good random tournaments doesn’t really mean much for a PGA golfer’s career. Even good, pro players can’t just play in any PGA tournament. If anyone were allowed to try and qualify, the first day of a golf tournament would never end. So only a pretty elite group are invited to most tournaments.

But, there’s a loophole.

These tournaments are sponsored by big companies: Northwestern Mutual World Challenge, Hyundai Tournament of Champions, Sony Open, etc. And with big sponsorships, comes a say in who gets to play.

So, Jason, who wants a lot more from his PGA career, emailed the corporate sponsors of an upcoming tournament, the Memorial. But a bunch of players send these exemption request emails.

Jason took it up a notch.

He also sent pictures of his home life to let sponsors know that he’s not just a golfer, but a real person supporting a family. And he’s persistent. He followed up with another note — this time, handwritten.

Who handwrites anything anymore?

That got their attention.

“He wrote a nice, compelling, personal letter to the exemption committee. And that stuck with them.”

Dan Sullivan, the tournament director

The Saturday before the tournament, Dan Sullivan called Jason and offered him a spot.

Jason took full advantage of the opportunity — placing 15th. Not too shabby. It’s a six figure paycheck and chances for more tour play, all because he stuck his neck out a little more than anyone else to ask for help from people who had the power to.


In high school, I really wanted to play basketball. I tried out for the freshman team. I wasn’t good enough and was cut during tryouts. But my father encouraged me to find the coach at school and ask if I could help the team practice. My father figured they might just need warm bodies to play against, and through the experience, maybe I’d get better enough to make the team someday.

It was nerve-racking. I knew the office where the coach would be at lunch. But I couldn’t get myself to open the door.

I looped around the building a couple times, passing the door each time. I was too afraid to go in. But, knowing I couldn’t go home and tell my Dad I failed to accomplish this, I grabbed the door knob of the office with my sweat-soaked hand, opened it up and walked up to the coach and made my pitch, “I’d love an opportunity to help the team practice if you need anyone?” He smiled, thanked me for coming in.

Then he said, “No.”

Many people would take that as a setback and never try anything like it again.

But I learned a different lesson.

I felt this tremendous accomplishment walking out of that office. I wasn’t going to play basketball, but I just got up the courage to ask someone to help me in a way no one else was asking.

And nothing bad happened. I was a little embarrassed, but I didn’t die from being uncomfortable.

I could ask anyone anything.

Later in high school, I ended up on the volleyball team. Unlike basketball, I was pretty good compared to most of my peers. But by junior year, I hadn’t grown as strong as some of my teammates, so it was getting tougher to stand out from the crowd in ability.

I found myself getting stuck in what they call a “back row specialist” position. This is a good place for a player who is quick and good at defense. There’s nothing to be ashamed of. I was actually really good at it. But I wanted more. I didn’t want to get substituted out every time it was time for me to play offense.

So, I walked up to my coach after a practice and asked him, “How can I get good enough that you’d let me play offense?”

This had the exact effect I wanted.

During practice he’d work me hard in offensive drills and scrimmages. Eventually I got better. By the end of the season, I was one of his starting offensive players.


I’ve been really fortunate on where Draft (a software product I’ve made to help people write better) has gone. But it’s not strictly because of talent or luck. Like Jason Allred, I was initially able to put a few good things and ideas together, but I needed help to keep the project going.

My blog, Ninjas and Robots, has been instrumental in spreading Draft. I got a big audience boost because it was one of the first blogs on Dustin Curtis’ SVBTLE blog network. But it was “invite only”. How was I lucky enough to get one of those invites?

For awhile, I had a guy helping me with Draft. We would meet every now and then about Draft’s product design and strategy. He was the one that pushed for great ideas like “comment out” your writing and little details that have really caught people’s attention. That guy is Jason Fried, the well known entrepreneur behind Basecamp and the publication where you are reading this. And that all eventually led to Jason asking me to take over Highrise and turn it into its own business.

A lot of people keep asking me, “How on earth did you manage to get Jason as a mentor?”

I’ve gotten some other really insightful advice during an hour-long phone call about Draft with Tim Ferriss, who’s famous for his Four Hour books. The phone call led to five action items that immediately improved the product. Not to mention, he’s even recently mentioned his love for Draft on his podcast. How’d I get someone as busy as Tim Ferriss to give me the time of day?

Dustin Curtis, Jason Fried, Tim Ferriss — none of these guys reached out to me saying, “Nate, what can I do to help you?” Why would they? They are inundated with their own lives.

The only way I entered into their orbits was by simply following my Dad’s advice from that time I wanted to make the basketball team:

Open up your mouth and ask.


P.S. It would be awesome to meet you on Twitter, or check out how you can improve your chances of asking for opportunities and following up using Highrise.

Business Failing? You Might Be Asking The Wrong Questions


Going around asking for “feedback” won’t get you anything useful. Here’s how to dig deeper and find real answers.

I did fine in Catholic school, up until 6th grade. I don’t know why Sister Freda hated me, but I think she was trying to teach me a lesson. And I did learn a lesson — just not the one she had in mind.

The turning point happened like this. During a reading comprehension exercise about becoming a veterinarian, Sister Freda asked me, “Name one challenge people have in becoming a vet.” I gave an answer. It was wrong. She told the entire class that this is what happens when students don’t pay attention. If I had done the work, she explained, I would have seen the section in the reading that held the correct answer. It was intended as a humiliating lesson.

At lunch, I showed Sister Freda the reading passage in my book. She apparently wanted me to regurgitate the challenges that students face when becoming vets. But I pointed out a later paragraph that contained my answer — that many vets struggle to run their own practices as business people.

“Ah, ok,” she said, and that was it. She saw that my answer wasn’t wrong — if anything, her question had been too vague.

At that moment, I realized that teachers are like everyone else — they make mistakes. And if I was going to be a great student, I couldn’t be so passive about my education.

Starting in 7th grade, I asked a ridiculous number of questions. My hand lived above my head. I forced myself to think of hypothetical or advanced questions beyond the realm of the text or the day’s lesson. People groaned when I was called on.

I remember a fellow student turning around when tests were handed back. He noticed that I had gotten the higher score. “How did you get a 100% when you’re always so confused and have to ask so many questions?”

Despite ridicule from my peers, I kept at it. My grades soared, and at the end of 8th grade I graduated second in my class. If only I had asked more questions, sooner.


Don’t Forget The Real Question

Someone emailed me recently with the subject: “A question about start-ups.” But the email didn’t contain a question mark or anything remotely looking like a question.

Often I get advice seeking emails ending with, “Do you have any feedback?”
 But that’s not a question; it’s a cop-out.

Similarly, I’ve attended meetings where entrepreneurs make presentations to experts expected to share helpful guidance. But often the presentation is, “Here’s my product, what do you think?”

Same problem. That’s not a real question. And so a conversation with these experts is unfocused and frustrates the entrepreneur because her real problems go untouched.

I’ve made the same mistake myself, but I’ve been lucky to learn a different way. The most valuable feedback session I ever had with a mentor came before I released Draft, a software product I made to help people write better. I was prepared. Instead of asking for feedback, I asked how this mentor and successful entrepreneur would design a specific feature in Draft or how would he communicate the business model I had planned? I got much more than feedback; I got answers.


How To Ask Better Questions

There are plenty of people who’d love to help you with your business; you just have to ask, but they don’t have time to waste helping you figure out what your actual problems are. Get the most out of a potential mentor by approaching them with specific questions you’ve already identified and they’ve probably answered for themselves. How would you:

  • Increase the conversion rate?
  • Set up pricing?
  • Design this feature so that it’s clear and easy to use?

And force yourself to go deeper with your questions.

Toyota’s engineering processes are famously effective. One reason is that employees are taught to ask why five times when trying to solve a problem.

  • Why is the battery dead?
  • Why is the alternator broken?
  • Why didn’t the customer get alerted to this before?

This process helps engineers identify and fix the root problem instead of just treating symptoms. The same practice can be applied to your startup venture.

Act like a Toyota engineer and ask why at least five times.

  • Why is my business not making enough money?
  • Why am I not measuring my conversion and attrition rates?
  • Why is attrition so high?
  • Why haven’t I surveyed anyone who has canceled?
  • Why haven’t I added feature X which most canceling users are asking for?

And most importantly… Don’t worry about looking silly with the number of questions you have; just ask more of them.


P.S. It would be awesome to meet you on Twitter, or check out how we can help you start or improve your own business with Highrise.