Ask Me Anything

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Ask Jason Fried Anything

Jason Fried is co-founder and CEO of Basecamp née 37signals, the company behind the namesake project management app and the new email app Hey. Along with his cofounder David Heinemeier Hansson, Fried has built a growing remote software company and documented his team's approach their Rework, Remote, and It Doesn't Have to be Crazy at Work books.

This AMA with Jason Fried was live on Capiche on on Monday, June 29th at 1PM Pacific (3PM Central).

17

How do you think about succession planning at Basecamp?

Answer
@jasonfried CEO, Basecamp
 

Haven't thought about, but the stress of the last two weeks made me want to quit a few times. Had the Apple decision gone another way, I seriously contemplated retiring. No joke. I didn't start this business to be told by a trillion-dollar company how I could sell my product, promote my product, or service my customers. I don't want to work in that kind of world. Luckily, it didn't go that way and HEY is thriving. I haven't been this excited about work for a long time, but it just goes to show how thin the line is, and how fragile things are when massive tech is in control.

13

If you could design Apple’s in-app purchase policies, what would they be?

Answer
@jasonfried CEO, Basecamp
 

Depends on the perspective you're asking me to take. Assuming our perspective...

All we're asking for is the choice. Companies should not be required to use IAP, but certainly IAP should be an option. For some companies IAP may be the perfect option, but there are so many companies, business models, cost structures, etc that one-size-doesn't-fit-all. For us - a multiplatform SaaS company with our own customer base and back office systems, IAP is a non-starter. It's both too expensive and too limiting. And we can't take care of our customers the way we want and they want. You can read more about that here: https://hey.com/apple/iap/

Further, companies shouldn't be forbidden from discussing payment, signup, or anything else in their apps. Right now it's hostile to the customer experience to not be able to tell them where to sign up, how to get help, how to update their credit card (if they purchased on the web), etc. It's just a mess.

So I'd like to see Apple's IAP offering stand up to choice. It would force Apple to make IAP even better. Competition's a good thing.

13

How is the planning process for launching a product in Basecamp?

Answer
@jasonfried CEO, Basecamp
 

We plan 6 weeks at a time. That's it. No road maps, no long term plans, no long feature list that has to be done before the product ships. We have an idea, we head towards it, we adjust as we go, we change our minds, we figure things out along the way. And then we're there.

We call this process Shape Up and you can read all about it in our free book here: http://basecamp.com/shapeup

12

Will Hey truly never allow any import of old emails?

Answer
@jasonfried CEO, Basecamp
 

Forever is a long time, but as of now there are no plans to allow imports from other services. HEY presents a fresh start. It's a rare thing, and a wonderful thing, but it's not for everyone. I'd look at it as an opportunity, not as a liability.

Yes, sometimes you may feel like you need to look something up from years ago. That's why an export is handy to have. Gmail, for example, lets you export to a single MBOX file. You can search that on your local machine whenever you want. 99% of the old stuff will never be useful again. There's no reason to keep lugging it around into new services for the rest of your life. Keep the export, dive in when you (almost never) need it, and move forward, fresh.

12

What is the level of priority for bringing custom domain support to HEY?

Answer
@jasonfried CEO, Basecamp
 

Custom domain support is coming this year. That's as specific as I can be. There are much higher priority things right now, but given that we promised it this year, it's high on the short list. It's quite complicated to do well and do right and make simple, so we're going to take the necessary time to get it right, but it's coming in 2020.

9

Do you see Basecamp as a competitor to Slack and MSFT Teams?

Answer
@jasonfried CEO, Basecamp
 

It doesn't matter what I see - it matters what the market sees. So sure, Basecamp is a competitor to Slack and Team and also the telephone and the in-person meeting and the whiteboard and the legal pad with your notes on it. Basecamp also competes with chaos and disorganization. Companies compete against all sorts of things, not just the obvious parallel services in the same category.

However, Slack and Teams can't compete with Basecamp on so many things because those services require other services to be useful. Basecamp's a true all-in-one tool - chat, messaging, long form messages, docs/files, meeting replacements, scheduling, tasks, reporting, status updates, etc - all in a single, simple unified interface.

9

Are you planning to support offline mode on Hey?

Answer
@jasonfried CEO, Basecamp
 

We don't have a roadmap, so I can't speak to the future. I can only say we're not focused on it at the moment. Right now we're entirely focused on the initial set of bug fixes and tweaks that come after a v1. We're just 14 days into the release of HEY, so lots of little things to tighten up.

We do have some offline support, however. For example on iOS, the Reply Later and Set Aside stacks are available offline. So we're headed in that direction, but I can't be specific about how far we'll go, and on which platforms. It's simply too early at this point.

9

Could contact sync come to Hey?

Answer
@jasonfried CEO, Basecamp
 

iOS would be much simpler, and yes, we'd like to see this happen at some point. Not a top concern at the moment, but I agree it would be quite a bit nicer. We're only 14 days into Version 1, so plenty of great stuff will be coming down the road.

9

What has the Covid-19 remote work experience taught us?

Answer
@jasonfried CEO, Basecamp
 

What we've always known: The office isn't a magic place. It's just a place. You don't need THAT place to get great work done. You need great tools, a great culture, great respect for one another, a desire to protect each other's time and attention, and a clear idea of where you're headed and what's required to get there. That's work. An office isn't work, it's just a space.

8

What was the decision process and considerations that lead you to tackle email as a problem?

Answer
@jasonfried CEO, Basecamp
 

So much frustration with email, and so little progress. Turning on the beginners mind and seeing how completely broken it was. Why don't I have control over who can email me? Why can anyone throw obligations my way? Why am I stuck with what other people call threads? Why do I have to follow the same conversation across multiple threads? Why do I have to archive emails to get them out of my way? Why can't I read email like I read Twitter - in an open feed rather than one item at a time? Why do I have to pop a bunch of tabs to read a handful of emails "together". It just goes on and on. It was time.

Email is a treasure. One of the most important inventions in 50 years. It deserved a dusting-off, a revamp, a potent reintroduction. We questioned everything, and the answers were too good to keep to ourselves. So we went all-in and made what we wanted to see in the world. That's HEY. And we're just getting started.

8

Would you every consider letting people use Hey with their own private IMAP server?

Answer
@jasonfried CEO, Basecamp
 

Ever for forever questions are hard to answer - anything's possible, it's just software - but it's highly unlikely we'd go in this direction.

8

What are you thoughts on a Hey Calendar?

Answer
@jasonfried CEO, Basecamp
 

Back in 2005 we built an incredible calendar into Backpack (our personal notes app). It remains the best calendar I've ever used. I'd love to tackle a calendar again. Like email, calendars are stale, lacking fresh ideas. We have dozens of ideas for an original, novel take on the calendar, but we don' have the time at the moment. Perhaps next year? Who knows! But yes I'd love to revive the calendar.

7

Has Basecamp considered resurrecting Backpack to compete in the new notes app wars?

Answer
@jasonfried CEO, Basecamp
 

Not interested in fighting any wars. No interest in reviving Backpack. We have our hands more than full with Basecamp and HEY (and soon HEY for Work). Next year we'll be releasing Basecamp 4 as well, so we have a lot of stuff going on already ;). Basecamp 4 is going to be amazing.

6

Is focusing on the Docs/Files tools going to be a bigger part of the Roadmap?

Answer
@jasonfried CEO, Basecamp
 

Not sure which product you're referring to here. For HEY or Basecamp?

6

What has been the most surprising learning in the launch of Hey?

Answer
@jasonfried CEO, Basecamp
 

I had a good feeling HEY would be well received. It's a fantastic product. But I didn't know so many people were so hungry for a revamp of email. We knew we were, but we didn't know so many others were. Over 150,000 people signed up in the first two weeks. It blew us away. We're so grateful - and so excited - that people craved something new. The last time people were excited about email was 16 years ago when Gmail launched. SIXTEEN YEARS! It's long past due for something new. HEY tapped into that energy, and we're thrilled to be able to show so many the leading edge of what email can and should be.

6

Is attachment preview coming to HEY?

Answer
@jasonfried CEO, Basecamp
 

We'd like to bring Basecamp's excellent attachment preview tech to HEY, but it didn't make v1. We don't have road maps so I don't know when we'll decide to bring it in.

6

What is the story behind the inception of Hey?

Answer
@jasonfried CEO, Basecamp
 

TBH, I don't have the energy right now to write that one up, but I will at some point! Soon Jonas, our design lead, will be sharing some of the early design directions on our blog at 37svn.com. That'll be fun to look at.

6

Can we please get smaller fonts in Hey?

Answer
@jasonfried CEO, Basecamp
 

We like the way it looks! ;)

There's a subtle strategy at play here. Zooming in a little prevents you from looking at too many things at once. I find looking at Gmail depressing because it's this one long list of all this stuff I have to deal with. HEY's size and layout and approach limits the amount of things in your field of vision and on your mind at any one time. It may not be for everyone, but neither is any particular layout. I think it's a fresh take, but I'm biased of course!

Also, iOS is pushing an update shortly which lets you adjust sizes based on your system settings.

5

How do you get the team to avoid feature rot and only work on the most valuable items?

Answer
@jasonfried CEO, Basecamp
 

A few of us define the work at a high level, and then the teams figure out how to implement those ideas in their own way. People aren't just randomly picking off projects - we're very diligent about the work we choose to do. You can read all about our process in our book Shape Up: http://basecamp.com/shapeup

4

Why did Basecamp quit using Textile formatting?

Answer
@jasonfried CEO, Basecamp
 

Too many issues for normal people. I like Markdown, but same thing happens. When you make a product used by millions, you quickly see how confusing anything is that revolves around text editing, expectations around what characters do, etc.

That's why we built Trix, or own WYSIWYG text editor. Visual formatting is the only way forward for the masses.

4

Any plans for redo, rethink and reintroduce a Facebook?

Answer
@jasonfried CEO, Basecamp
 

Nope. The problem doesn't interest me.

4

Could iOS/macOS get truly native feeling/functioning Apps for Hey at any point?

Answer
@jasonfried CEO, Basecamp
 

We think the HEY apps on iOS and Android are fantastic.

On Mac, we'd like to do a fully custom app at some point, but it's a ton of work, and not a high priority. The web app is fantastic, and people are very comfortable using web-based email.

4

Do you feel your ‘Shape up’ methodology would work at scale?

Answer
@jasonfried CEO, Basecamp
 

I don't think scale has anything to do with it one way or another. It's not about size or scale, it's about mindset and approach.

4

What accomplishment are you most proud of in your career?

Answer
@jasonfried CEO, Basecamp
 

Getting a chance to work with some of the smartest, kindest, most creative people I've ever met.

4

Take on instant messaging next? Have you ever thought about it?

Answer
@jasonfried CEO, Basecamp
 

Early HEY prototypes incorporated IM + email, but we didn't have a lot to add on the IM side, and it added significant complexity to the concept, so we didn't pursue it. But who knows what the future holds! In general, IM seems pretty OK to me, so we don't have the burning desire to repair what isn't broken. Sure it can be improved, but it needs to be broken (or neglected) for us to really want to touch it.

We do have instant messaging built into Basecamp 3, and we have some novel ideas for improving it in that context in Basecamp 4 next year. We'll see!

4

What do you have to say to the critics that call Hey a very opinionated app?

Answer
@jasonfried CEO, Basecamp
 

I'd say they're right! That was the whole idea - bring a new set of opinions about what email should be, could be, and can be. More opinions coming!

3

Are you considering letting Hey filter email seders who dynamically generate a unique from address for each message?

Answer
@jasonfried CEO, Basecamp
 

Yeah that's bad at the moment. We'd like to do something about that.

3

If you had limitless time and resources, what other problems would you want to solve?

Answer
@jasonfried CEO, Basecamp
 

Same ones I'm working on now.

No one has limitless time or resources. We should be spending whatever time and resources we do have on the situations we think we can improve. I'm focused on what I'm good at (which is hopefully software, design, leadership, writing, etc). I'd focus on the same things if I had an extra 8 hours a day, or some other additional measure of resources I'd need to do what I already do.

3

Any thoughts on a next book? With either you and DHH, or one of the team members.

Answer
@jasonfried CEO, Basecamp
 

Ha! Nothing planned at the moment. We don't set out to write books. Books are reflections on what we've already written. "It Doesn't Have to Be Crazy at Work" is as current as it gets.

2

Can you tell us about a bet that you felt so sure would succeed but ultimately failed? Similarly, a bet that you maybe weren't 100% behind that succeeded.

Answer
@jasonfried CEO, Basecamp
 

I can't be certain about anything, and I don't go into any endeavor seeking certainty. I try to find a confident place where I feel good about the odds, but ultimately everything's a bit of a long shot. Outcomes are more commonly determined by things we don't control, than the things we do.