It’s OK not to use tools

Recently I did a little side project to improve the website for a non-profit animal shelter in our town. The existing site was an outdated Microsoft FrontPage menagerie, so basically anything I did would be a big improvement.

I spent around 20 minutes creating a simple design in HTML, and then several hours editing, rewriting, and refining the copy. In the end, I reduced a scattershot 25-page website down to about 8 focused pages written in a friendly tone.

My next instinct was to apply our great modern web toolset to the site. Let’s add a static site generator or a CMS! Let’s add Sass and a grid system! Let’s do more fashionable things!

Then I started looking at those tools critically. A static site generator usually requires knowing Markdown and esoteric commands and configuration. A typical CMS will need setup, logins, security patches, templates, and maintenance. Even hosted CMSes have a lot of cognitive overhead, and the content is trapped away inside someone else’s system.

These are tools made by geeks, for geeks. Why do we need a CMS for an 8-page site? And for that matter, why even bother with Sass? Regular old CSS can do the job just fine.

Who knows who will take over the site in the future. I’ll hang with it for a while, but someday someone else might have to work on it. It would surely be easier to do that with 8 simple, straightforward HTML files than with some custom WordPress installation that’s several versions out of date. So what if I have to repeat the navigation markup 8 separate times? It’s not that hard. We used to do it for much larger sites!

Today, a basic HTML/CSS site seems almost passé. But why? Is it because our new tools are so significantly better, or because we’ve gone overboard complicating simple things?

As builders, we like tools and tech because they’re interesting and new, and we enjoy mastering them. But when you think about the people we’re building for, the reality is usually the opposite. They need simple designs, clear writing, less tech, and fewer abstractions. They want to get stray animals adopted, not fuss around with website stuff.

Remember when the web was damn simple? It still can be. It’s up to us to make it that way.

Introducing Mercedes De Luca, Basecamp’s first COO

Today we’re feeling really good because we get to announce that Mercedes De Luca will be joining Basecamp as our first-ever COO.

Over the last few years, David and I have come to realize that high-level strategy and hands-on product development is what we enjoy doing most. But of course there’s so much more to running a company than just that stuff.

Products are products, but companies are products too. Your company should be your best product, since it’s the product that produces all the others. We should operate the company with as much love and attention and care as we put into building our products. We want Basecamp the company to be outstanding at every level.

Mercedes is going to help us be all we can be. She’s been a CEO, a CTO, a CIO, and a GM. She’s run big groups and small groups — local and remote. She has the right mix of a structured, analytical mind and an insightful, creative spirit.

She’s wonderful with people — warm, approachable, and motivated to help everyone else be the best they can be. She’s excellent at spotting gaps, identifying things we should be trying that we’re not, building up capabilities without introducing bloat, and pulling together a team that produces results without compromising what a company stands for. She’s a person of principle and strong character. Her references were glowing — and so many of them touched on just how wonderful a person she is. That had a big influence on us.

We’re fortunate to have her on our team. We’re going to learn a lot, do a lot, and have a lot of fun along the way. And like the majority of our company, she’ll be working remotely (she’s based in California).

We were careful and deliberate with our COO search. We’ve got a great thing going here and the easiest thing to do is to fuck it all up. This is a major role and we don’t want to upset the balance that makes this company what it is today and what it’s been for nearly 17 years. We were looking for someone who would feel like they’ve been here for years, but also someone with a fresh outsider’s perspective. Someone who can push us in new directions and challenge us to do things we may have never done on our own — but never at the expense of the values we hold near and dear.

We talked to contacts we knew, asked others for recommendations, and ultimately hired an executive recruiter to help find the perfect fit. After interviewing an august collection of highly qualified and capable people, Mercedes stood out as the one for us. When it comes to considering a group of people who are all clearly qualified to do the job well, it ultimately comes down to something else — comfort. How do you feel about someone? Who do you click with? Who has the right combination of subtitles, perspectives, and life experiences that add up to something unique? For us, Mercedes had all the right stuff.

She’ll be starting in a few weeks. We think you’ll be able to feel her presence and influence in 2016. With an all new version of Basecamp right around the corner, with the best team we’ve ever had, and with Mercedes joining the crew, we look forward to the new year, the next decade, and beyond. Good stuff on the way.

Thanks for listening.


Originally published at signalvnoise.com.

Look and Feel and Feel

Designers often talk about the look and feel of a product, an app, an object, etc. These are good concepts to be talking about, but how the thing feels isn’t really the important feel. The important feel is how it makes you feel. That feeling isn’t usually covered by look and feel discussions.

This has recently come into focus for me. The trigger? Instagram.

I’ve been on Twitter (@jasonfried) for years. Since I don’t have a Facebook account, Twitter has been my only social networking outlet. I mostly use it for sharing novel or interesting things I’ve seen or read, the occasional quote, or a point of view, perspective, or epiphany about something business related.

I follow just under 200 people. Some of them I know personally, others I’ve never met, some are brands, some are individuals, some are because of hobbies or special interests, some are dead serious, others funny or silly. It’s a healthy mix, and I try to pay attention to everything that shows up in my feed.

Twitter’s an amazing thing, no question. I think it’s one of the most important products ever, and it’s absolutely changed the way ideas, news, insights, complaints, and casual communications happen.

A few months ago I signed up for Instagram (@jason.fried). I started following a few people — some of the same people I follow on Twitter. Almost immediately I felt something — I felt good! Instagram makes me feel good. I enjoy thumbing through Instagram.

Since then, every time I’ve gone back to Twitter, I’ve noticed I’ve felt anxious, unhappy, uncomfortable. I didn’t notice this before I started using Instagram, because I didn’t have anything to contrast it with. It was just the way it was, and I didn’t think much about how it made me feel.

Every scroll through Twitter puts at least one person’s bad day, shitty experience, or moment of snark in front of me. These are good happy people — I know many of them in real life — but for whatever reason, Twitter is the place they let their shit loose. And while it’s easy to do, it’s not comfortable to be around. I don’t enjoy it.

Every scroll through Instagram puts someone’s good day in front of me. A vacation picture, something new they got that they love, pictures of nature, pictures of people they love, places they’ve been, and stuff they want to cheer about. It’s just flat out harder to be negative when sharing a picture. This isn’t a small thing — it’s a very big deal. I feel good when I browse Instagram. That’s the feel that matters.

So now I have a choice… When I have a few minutes to kill, and my phone is in front of me, I almost always reach for Instagram. I never regret it. I come away feeling the same or better. When I occasionally reach for Twitter, I discover someone’s pissed about something. I often come away feeling worse, feeling anxious, or just generally not feeling great about the world. Twitter actually gives me a negative impression of my friends. I know it’s not Twitter doing it, but it’s happening on Twitter. that’s how Twitter feels to me.

None of this has anything to do with how the apps look or feel. It’s not the buttons, it’s not the animations, it’s not the interface or visual design. It’s not the colors, it’s not the font, it’s not the transitions. It’s how using the apps make me feel before, during, and after. The sense of anticipation (am I about to see something wonderful vs. am I about to get a dose of someone’s bad day?), the things I experience as I scroll through (a butterfly vs. an injustice), and how I feel once I’m done (that was nice vs. fuck that — ugh).

The Twitter vs. Instagram experience is really reinforcing what matters when designing a product. What kind of behavior can we encourage? What kind of moments can we create for people? What do people anticipate before they use something? How does it leave them feeling when they’re done? These are now some of the most important questions for me when working on a design.

BTW: You can follow me on Twitter at @jasonfried or on Instagram at @jason.fried. I promise to keep both positive.


Originally published at signalvnoise.com.

How much is Basecamp worth? I don’t know and I don’t care.

I was recently speaking to a class at a local university and the topic of valuations came up. One student asked me what our valuation was. I gave her the honest answer: I haven’t a clue.

How is it possible that a successful software company today doesn’t know its worth? A valuation is what other people think your business is worth. I’ve only ever been interested in what our company is worth to us.

Startups these days are bantered about as if they were in a fantasy football bracket. Did you hear Lyft raised another $150 million at a $2.5 billion valuation? But Uber got tossed another $2.8 billion at a $41.2 billion valuation! Then there are the companies barely off the ground getting VC backing with 25x valuations, despite having no product or business model.

Entrepreneurs by nature are competitive. But fundraising has become the sport in place of the nuts and bolts of building a sustainable business.

The last time I considered Basecamp’s valuation was nearly a decade ago. We’d been approached by dozens of VC firms looking to invest. But with a solid product, a growing consumer base, and increasing profitability, we didn’t entertain any offers.

Then, in 2006, I got an email from Jeff Bezos’s personal assistant. Jeff wanted to meet. I’d long admired him for what he was building at Amazon, and how he generally sees the world. I took the meeting.

After a visit to Seattle and a few more calls, Jeff bought a small piece of our company. I didn’t take the cash out of some fantastical desire to turn Basecamp into a rocket ship. Instead, his purchasing shares from me and my co-founder took a little risk off the table and gave us direct access to the brain of one of today’s greatest living entrepreneurs.

In the years since, we’ve been approached by nearly 100 private investors, VCs, and private equity firms. They want to put money into our company, but we don’t want it. It’s not hubris; it’s the cost that comes with the cash. I want to deliver a product that our customers want, not one that our investors want. I want to grow our company according to our timetable, not one dictated by a board. For many startups, funding has worked to their detriment — unnecessarily raised stakes, a path to unnaturally rapid growth. Venture capital is not free money.

Years ago, during the investment discussion with Jeff, we had to place a financial value on our company. The process of constructing a valuation was pretty silly, to be honest. We drew up charts, made some educated guesses, negotiated back and forth, and ultimately came up with a figure. We made it up, as everyone does. Let’s just admit it right now: Financial projections are big, fat guesses. They are best-case scenarios. Since they’re hypothetical, why not pull a number out of a hat?

Jeff knows this. All investors know this. Yes, you can look at revenue and profit and multiples, but so many tech company projections these days aren’t based on anything real. They’re based on fantasy. And too often, the more profit you have, the lower your valuation is. Because nothing pops the valuation bubble like reality.

My not knowing how much our company is worth doesn’t affect our business on a daily basis. I know our revenue and our profit. I know how fast we respond to customer service inquiries and how many people signed up for Basecamp last week. Those are real numbers to me. A valuation is an invented number that ebbs and flows on the basis of how much someone else thinks you’re worth. It’s nothing more than a distraction.

Why the Drudge Report is one of the best designed sites on the web

Here are a few reasons, in no particular order, why I think The Drudge Report is one of the best designed sites on the web.


Staying power

People talk about timeless design all the time. But most things people point to that are timeless end up being time stamped. The Drudge Report, on the other hand, has proven timeless. It’s generic list of links, black and white monospaced font, and ALL CAPS headlines have survived every trend, every fad, every movement, every era, every design do or don’t. It doesn’t look old and it doesn’t look new — it looks Drudge. It hasn’t changed since at least 1997, and I believe the design goes back even further. How many sites can survive — and thrive — unchanged for a decade? That’s special.

It’s straightforward

There are no tricks, no sections, no deep linking, no special technology required. It’s all right there on one page. “But it’s a mess!” you could say. I’d say “it’s straightforward mess.” I wouldn’t underestimate the merit in that.

It’s unique

When you’re on the Drudge Report you’re on the Drudge Report. There’s no question where you are. The design has become iconic. How many other news sites can claim that? If you pull the logo off some of the other major news sites/networks (CNN, MSNBC, FOX News, ABC News, CBS News, etc.) you may have a hard time distinguishing them from one another. They all sorta blend into the same standard news-site look and feel. There are a few standouts, but even the NYT and the WSJ aren’t that unique. Drudge’s design stands alone.

This is important

Many news sites have lost their guts. They’re afraid to really call out one big story. They may have a leading headline, but it’s not all that obvious or different from the others. It may be a font size or two bigger, but it’s not confident. They hedge. Drudge, on the other hand, says “this is the story of the moment” with a huge headline. This is what’s important in the news right now and nothing else even comes close. Drudge isn’t afraid to be an opinionated editor and his site design perfectly emphasizes that. It’s bold, it’s risky, and it’s pure Drudge design.

It’s good cluttered

The Drudge Report usually leads with a “font size=+7” ALL CAPS headline in Arial. Sometimes it’s italicized. Sometimes, for something big big, he’ll cap it off with the infamous siren.

The infamous Drudge siren.

After that you have three columns. Some headlines are sentence case, some are ALL CAPS. Some have photos, some are just a plain text headline. Sometimes more controversial or sensational headlines are colored red. There’s usually a big ad at the top and a few other ads sprinkled among the columns.

Stories aren’t grouped or organized except probably more interesting ones up top. And that’s it. Your eye darts all over the place looking around for something that looks interesting. The design encourages wandering and random discovery.

The site feels like a chaotic newsroom with the cutting room floor exposed. I think that’s part of the excitement — and good design.

Breaking news is breaking news

Have you seen “breaking news” on MSNBC or CNN lately? Almost anything can pass for breaking news now. “So and so speaks to the press about this or that” is now breaking news. Breaking news used to mean something seriously big and important or spectacular just happened. But the major news sites have watered it way down. When I hit MSNBC or CNN, and they have a “breaking news” bar (red/yellow usually), it’s easy to ignore because they’ve cried wolf one too many times. But when you see a big honking red ALL CAPS headline with the flashing siren on Drudge, you know it’s newsworthy.

One guy can run it

The site is run by Matt Drudge full time with help from an occasional part-time contributor. If the site was 5 pages or 10 pages or 30 pages, he’d likely need additional people and technology to manage it all.

No news is the news

The Drudge Report is a headline site. There’s no “content” on the site. Yet, that’s news. The headlines themselves can be news. Drudge breaks stories without writing stories. In fact, The Drudge Report may be one of the only sites on the web that can break a story with just a headline or a photo. That’s baked right into the design.

It sends people away to keep them coming back

There’s actually no content on the Drudge Report. Well, sometimes he will post an email or a memo on his site, but it’s 99% links out to other news sources. His site is designed to send you away to bring you back. The more often you hit his site to go somewhere else the more often you’ll return to go somewhere else again. You visit the Drudge Report more because you leave the Drudge Report more. This is one of the secrets to building traffic: The more you send people away the more they’ll come back.

It’s fast

When you visit The Drudge Report, you get the Drudge report. There are no interstitial ads. There’s no load time. There’s no buffering. There’s nothing but instant content. The Drudge Report is Google-fast and Craigslist fast — quite a feat for a site that does 3,000,000 uniques a month run by one guy.BTW: Those 3,000,000 uniques a month translate into hundreds of millions of visits a month (source: CNN).

It’s cheap to maintain

The design of the Drudge Report doesn’t require a fancy CMS or, in fact, anyCMS at all. It’s edited by hand. His overhead is probably a couple grand a month max. A few thousand bucks a year in overhead that generates a few million a year in revenue. That’s good design.

It’s one page

The Drudge Report is one page. Every visit and every visitor is focused on that one page with a headline and three columns. He knows exactly what people are going to see, he knows exactly how people are going to see it. There’s no mystery page here that hasn’t been redesigned or mystery page there that’s throwing an error. It’s one page to look at at one page to work on. It is what it is. It doesn’t try too hard to be something it’s not.

It makes him a great living

Based on published ad rates and traffic numbers, it’s estimated that Matt Drudge makes “over a million a year.” Not bad for a single black and white page on the internet.

So these are some of the reasons why I think The Drudge Report is one of the best designed sites on the web. Swing away.

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.