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Basecamp CEO Jason Fried: We Banned Talking Politics and 1/3 of our Team Quit | 20VC #963

Jason Fried the Co-Founder and CEO at 37signals, makers of Basecamp and HEY. Over an incredible 21 year journey, Jason and his co-founder David have scaled Basecamp to become the communication tool trusted by millions. Jason is also the co-author of the widely acclaimed, ReWork and has also made several angel investments in the likes of Intercom, Gumroad and Hodinkee to name a few. --------------------------------------------------- Timestamps: 0:00 Basecamp’s Origin Story 1:39 What are you running from/towards? 4:31 How to Detach from your Company 6:27 What happens to SaaS companies that are unprofitable and over funded? 9:58 Scale is Overrated 12:02 How Jason Measures Success 13:53 Goals are Overrated 19:04 How to Give Negative Feedback 21:18 Basecamp’s Ban on Talking Politics at Work 27:53 Jason’s Decision Making Framework 32:15 Jason’s Biggest Disagreement with his Co-Founder 34:46 The Secret to Long Lasting Business Relationships 37:40 The Secret to a Happy Marriage 40:26 Parenting Advice 42:30 Eating Mushrooms 45:07 What would you like to change in the world of startups? 45:53 Founder who Take Money off the Table 46:57 Jason’s Risk Appetite 49:56 The Perfect Board Member 51:25 Jason’s 10-year Plan ---------------------------------------------------- In Todays Episode with Jason Fried We Discuss 1. From Web Design Agency to Founding Basecamp: What was the a-ha moment for Jason when they had to make the pivot from a design agency to going full-time launching and running Basecamp as a SaaS company? What is Jason running towards? What is he running from? What is the single biggest fear that Jason is trying to avoid? 2. Jason Fried: The Leader: Why does Jason believe he is running from his position as leader and CEO @ Basecamp? Why does Jason not like or agree with goals or targets? Why are they not helpful? How does Jason make decisions today as a leader and CEO? What one question does he ask that determines his decision-making process? Why does Jason never compare himself to the competition? Why does he believe competition is for losers? 3. Jason Fried: The Politicization of Leadership: Why did Jason and David decide to not allow politics in the workplace? How did they manage with 1/3 of their team leaving overnight? How was that experience for them personally? How did it impact the company? Is there anything they would do differently? Does Jason believe we will see the continued politicization of leadership in the coming months? How would Jason advise other CEOs when it comes to taking a stance on politics? 4. Jason Fried: Building the Best Team: What is the one question that determines whether you made a good hire? Why does Basecamp start with hiring all employees on a week-long project contract? Why does Jason believe the best CEOs approach management as the art of the individual? 5. Jason Fried: The Partner, Father and Husband: Jason and David have been partners for 21 years, why does Jason believe it is helpful that they do not see each other much? Is it right for co-founders and partners to be friends? What have been Jason’s single biggest lessons on what it takes to be the best husband? What does great fatherhood mean to Jason? How has it changed over time? ------------------------------------------------------------- Subscribe to the Podcast: https://www.thetwentyminutevc.com/jason-fried-2/ Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Jason Fried on Twitter: https://twitter.com/jasonfried Follow 20VC on Instagram: https://www.instagram.com/20vc_reels Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok ------------------------------------------------------------------- #JasonFried #Basecamp #HarryStebbings #20vc #startups #venturecapital #leadershipdevelopment #hiringtips

Harry StebbingshostJason Friedguest
Jan 6, 202353mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:001:39

    Basecamp’s Origin Story

    1. HS

      Jason, I am so excited for this. I loved our first episode, so thank you so much for joining me once again.

    2. JF

      It's wonderful to be back. It really is.

    3. HS

      Now, for people that missed the first show, quick intro, one to two minutes, how did you come to found Basecamp now 23 years ago?

    4. JF

      23 years ago. So, uh, (clears throat) I was working on my own, freelancing, doing website design. And, um, I'd been doing that for a few years and got bored working on my own, frankly. I mean, I, I was just in my apartment, you know, got out of bed, rolled to my desk, did work, rolled back to bed, not really what I wanted to do long-term. So I hooked up with a couple friends who were also looking to start a business, website design business, and that's where we started the business together. Um, and then a few years later, we started making Basecamp, the, the software that, that we're known for today primarily, um, because we needed it for our own business. We were doing a lot of website design projects so I had a lot of clients and we couldn't really keep things in order. We were dropping the ball, you know, uh, missing deadlines. Clients didn't know what we were doing. We didn't know what we were doing. And so we built this thing which eventually became Basecamp to manage that- those projects and that work. And we started using it with our clients and they said, "W- what is this thing? Like, we need this for our own business." And we said, "Ah, okay." So we turned it into a product, put some prices on it, put it out in the market in February of 2004, and about a year later or so, it was doing more... generating more revenue for us than our website design business. So we stopped doing website design and been doing Basecamp and other products ever since.

    5. HS

      It's very funny, I just had Ben Chestnut on from Mailchimp-

    6. JF

      Oh, yeah.

    7. HS

      ... and it was pretty much exactly the same founding story.

    8. JF

      Same story.

    9. HS

      Yeah, exactly.

    10. JF

      Yeah.

    11. HS

      Um, listen, the child psychologist within me, clearly I have too much free time, but tells me that, you know, we're all a function of our histories, okay? And

  2. 1:394:31

    What are you running from/towards?

    1. HS

      so that means we're all running from something and we're all running towards something. When you think about first what you were running from, what are you running from, Jason?

    2. JF

      What am I running from? Um, I would say I'm, uh, if I had to pick something without really thinking about it is, um, I don't like structure. I don't like, um, requirements. I don't like, um, waking up and working for other people and doing what other people tell me to do or what I'm supposed to do. So I think my sort of entrepreneurial independent streak is a, is an example of, of me sort of going in the opposite direction of that. Um, running my own show, um, not really, you know, not taking money so I'm not beholden to anybody. We don't have a board of directors. All the things we do as a business are very much f- centered in independence and being able to do what we wanna do our own way. I'm guessing that is tied somehow, somewhere to my past where I felt sort of maybe tied down or, um, limited. And so-

    3. HS

      Were you-

    4. JF

      ... this is sort of my way to be unlimited, perhaps.

    5. HS

      Were you, were you good in school?

    6. JF

      Not really. I was a C or B student, you know, I was average. Um, mostly because I, I just didn't really find a lot of it interesting. There was some things I, I really did find interesting, but it always came down to my teacher.

    7. HS

      Mm-hmm.

    8. JF

      If I had a great teacher, I was into it. If I w- if there wasn't a great teacher, I wasn't so into it.

    9. HS

      What are you running towards, Jason?

    10. JF

      That, I don't know. I think it's probably a lot easier for me to say... Actually, you know what? Uh, what I probably would say is I'm running towards eventually not doing this anymore. That's what I'm running (laughs) towards at some point. So I've been doing this for 23 years, still love doing it, still wanna keep doing it, but obviously I can't... I'm not gonna have 25 or 23 more years ahead of me in this job. That's just not gonna happen, nor should it, nor do I deserve to have it. So for me, I think probably I'm running towards, um, running away from this.

    11. HS

      I, I-

    12. JF

      Um, not in the short term, but, like, that's where I have to be headed naturally, I think.

    13. HS

      And if I was a Business Insider journalist, I would do, "Jason Fried wants to leave Basecamp."

    14. JF

      (laughs)

    15. HS

      Arseholes. (laughs)

    16. JF

      Eventually, yeah. Don't we all?

    17. HS

      Yeah. (laughs) Yeah.

    18. JF

      Don't we all eventually wanna, want to do something else? I mean, I- I've not wanted to do something else and I don't have anything else that I wanna do. But realistically, um, you know-

    19. HS

      Uh-

    20. JF

      ... I'm, I'm, I'm curious-

    21. HS

      ... it's-

    22. JF

      ... to see what someone else could do with this business.

    23. HS

      The question I have for you-

    24. JF

      Yeah.

    25. HS

      ... and this is just, I, I did have it scheduled but fuck it.

    26. JF

      (laughs)

    27. HS

      Um, identity, man, you say like, you know, that kind of detachment from the business. I don't like going on holidays now, Jason, because I've done mine for eight years. I don't know who I am when I'm on holiday when I don't have my business. It's such a part of me. Do you not worry that actually when it comes to your attachment to your company, you have an inability now to detach yourself from your company?

    28. JF

      Um, I don't

  3. 4:316:27

    How to Detach from your Company

    1. JF

      know. So I'm taking my first sabbatical, um, in January, January and February, about six weeks. Um, which isn't that much of a sabbatical according to, to some sabbaticals, but for me, it's, it's the first time I've been away, I'll have been away from the business for that long. I'm looking forward to that because I think it's gonna be quite clarifying for me, y- you know, what is it like not to do this? Um, can I not wait to get back? Do I like the distance? I, I don't know. Um, but I feel like I need to know. Uh, I should know, and this is the first step towards that. Personally, even though I've been doing this for a long time, I, I have a, this, this fantasy of basically, uh, also not doing this, closing my laptop, and not opening a computer again. I, I, I don't like looking at computers all day. Um, I like making things, which is what I get to do at work, but I don't like the mechanics of, of sitting in front of a computer and looking at it all day. So yeah, I, I would love... Whenever I am done with this, I'd like to close my laptop for at least a year. I'll have my phone, I can connect with people if I need to, but I don't wanna be looking at a ke- a keyboard and, and looking into a screen for, for a while.

    2. HS

      Mine's so funny. I always think, like, "Oh, wouldn't it be so nice to not have emails and not have the incoming." And then Thanksgiving comes or Christmas comes and I feel hopelessly unloved and-

    3. JF

      (laughs)

    4. HS

      ... like something's very wrong, which probably shows, you know, how much I need to see another therapist. But-

    5. JF

      Well, (laughs) -

    6. HS

      (laughs)

    7. JF

      ... here's the thing. I've got, I've got two young kids. I, I'm very occupied, you know, with, with life other than work too. So I think it'd be different for me if I was quite a bit younger, solo, you know.... I, I think I probably would have needed work more than I feel like I need it now, as much as I still do enjoy doing it.

    8. HS

      So, one of the things that I've learned doing this show is that the best interviews are the people that don't have a boss. That's very rare, actually. Every VC has a boss, it's our LPs. Every founder has a boss, it's your, uh, investors if you're a venture-backed company.

    9. JF

      Yeah.

    10. HS

      Um, you don't have a boss and so this, this set of questions I'm really

  4. 6:279:58

    What happens to SaaS companies that are unprofitable and over funded?

    1. HS

      intrigued for. We've seen a generation of SaaS companies now that are unprofitable and heavily venture-funded. And now, we have a macro turning. What happens to them? Heavily unprofitable, heavily funded?

    2. JF

      It's gonna be hard. I think there's a lot of risk baked into this that people haven't thought about. They assume that companies will be around forever, big companies will be around forever. Um, you know, they see brand advertising all over, it makes people think there's stability there. But, but there just simply isn't if, if a company can't make its own money, they require outside money, outside money dries up, things have to change. I mean, there's gonna have to be la- uh, there already is, it's not like th- this is news, but layoffs, deep cuts, some austerity measures. Um, you know, these companies are gonna realize they probably have too many people, um, and they've been spending wildly on things that don't work. Um, they've been just in a, in a, a market share grab, so they're, they're, they're losing money on every customer, but they need to grab them because otherwise someone else will grab them. There's this whole mentality out there that I think is gonna shift. It has to shift. It's not even that I think it ha- it will, it has to. There's basi- it's basic physics at some point, it's basic economics. If you don't make more than you spend and you don't have a lot of cash sitting around and you burn through it, you've gotta cut costs, uh, and you've gotta be a different business. And I think that's, uh, creeping up on a lot of companies right now. Uh, and, and the problem is, is that they're not practiced in the art of profitability. They've gotten really good at spending money, but not really good at making money. They generate revenue, lots of revenue, but, um, the, the way they operate their business doesn't, it doesn't pay off ultimately in the end. So, they're gonna have to figure out how to do that on the fly quickly.

    3. HS

      So, I said that there were some spicy questions that people submitted. So, this is them, not me. You can hate them.

    4. JF

      (laughs)

    5. HS

      Uh, so you mentioned, like, uh, you know, someone else will get those customers if they don't. One question that I got was, I'd love to hear his thoughts on (laughs) I've really gained in confidence I'm asking this.

    6. JF

      Mm-hmm.

    7. HS

      Uh, they said, "How did you lose your head start in every product to Atlassian?" Is that fair? And how do you feel about that?

    8. JF

      Um, I don't really know what that means. So, I think that there's a lot of customers out there, um, there are a lot of companies out there, and we get customers flooding to us from Jira all the time, and I'm sure Jira gets customers that are coming from us all the time. There's a, you know, a, a, a, a, a transfer all the time, people trying this, trying that. They try something for a while, it doesn't work. They try this for a while, they come back and forth. So, the thing is, is that it doesn't matter to us what other people, how other people are doing in terms of the number of customers they have. This is, I think, something entrepreneurs get wrong all the time.

    9. HS

      Hmm.

    10. JF

      They, they compare themselves to someone else and they go, "How many customers do they have? How many customers do they have?" All that matters is do we have enough customers to make our own business work? That's all that matters. So, I'm happy to see Atlassian, Jira, uh, Trello, whatever their products do well. That's great. We can do well, they can do well. This is not a zero-sum game. We have our own economics, they have their own economics. As long as we can make our economics work, which we have, we've been profitable for 23 years, every year, it doesn't matter how many we have versus how many they have. All that matters is can we make our business work? So, I don't, I don't really, I don't care about any of those things. Um, and I know the reality is, is cu- customers come and go on all, all platforms and, and that's just sort of been the, the truth of, of two decades of, of being in this business.

    11. HS

      I think SaaS companies

  5. 9:5812:02

    Scale is Overrated

    1. HS

      are now ingrained with this ideology that you have to scale up. The big ACVs, the big contracts are what matters and it's where your business will always be ultimately, even if it's not today.

    2. JF

      Yes.

    3. HS

      Dharmesh at HubSpot says differently. I'm intrigued to hear your thoughts on this in terms of does that have to be the way in SaaS? And if so, how do you think about advising founders on when is the right time, or if they need to at all go upmarket into massive enterprise?

    4. JF

      Well, a- again, it comes down to what are your economics? So, I'm just ra- making up numbers here. Let's say it costs us five million bucks a year to run our business and I wanna make six. That's good. It's not about scaling up or scaling down. It's covering your costs and then coming out with a profit on top of that. Like, that's, it, this idea of scaling, like, for what reason and to what end and where are you going with it? Like, I, there's so many companies scaling and losing their ass. That doesn't seem like a good plan. They're getting bigger and bigger and bigger and so are their losses. So, like, I, that doesn't work. I don't see what that means. And, and if they follow the same path, they're gonna keep losing more and more and more because they're unprofitable per customer. So, it's, like, this idea of scale has never been something that really made any sense to me. What makes sense to me is how do you operate profitably? Um, that's, that's how I know how to run a business. Uh, and it might mean we've left plenty of opportunities on the table, or we could have been bigger and all these things, but bigger f- to what, for what reason? Again, like, I don't wanna be bigger and have much lower margins. I don't wanna be bigger and lose money per customer. I don't wanna be bigger and have to take a bunch of money to support that growth. Like, I don't want any of those things. Um, and so my, to, to your second point about advising, it, it's, it's, uh, don't worry about everyone else's business. Worry about your own business. What do you need to survive? What do you need to be profitable? Where do you wanna go? That's all that matters. And, and there's, I think there's too many people focused on, like, what everyone else is doing and, and the industry and all these things that don't really matter that much. I mean, we pay attention to what's going on, but really, you've gotta make your own business work and don't worry about

  6. 12:0213:53

    How Jason Measures Success

    1. JF

      everyone else's.

    2. HS

      How do you measure success? Is it pure profitability? Is it-

    3. JF

      Mm-hmm.

    4. HS

      ... innovation? Is it team morale? What's your metric for are we doing a good fucking job?

    5. JF

      Profitability is important to us fundamentally, right?

    6. HS

      Yeah.

    7. JF

      Um, but the other part of it is simply, would I want to do this again? Like, is- is what we're doing on a day- daily, weekly, monthly basis, like, are we enjoying doing that, and would I want to do that again? If I could choose, would I want to live that month over again? Would I want to live that work month over again? That's kind of what it comes down to 'cause if we're making a pile of money and we hate each other, not interested in that. If we're wildly profitable and every project sucks and- and people don't want to be here and I don't want to be here, that's not worth it. So, it ultimately has to be about do you want to keep doing this? Is this a place you want to spend your- your creative time and your- and your, you know, your- your craft? Is this a place you want to hone that and enjoy that and work with great people that you like and all those things? Like, that has to be number one. Um, but profitability has to be, like, 1A. Because if you can't- if you don't maintain profitability, you have to rely on outside sources of money, and then you're beholden to all sorts of realities that you don't control. Not that you really control any of these things, but it just becomes a lot harder. And I don't want to, um, I don't want to spend my days worrying about, um, how I can make some fund a lot more money. Like, I just gotta figure out how we can make our own business profitable and enjoy the work that we're doing. That's really it for me. I don't, we don't have financial targets, we don't have financial goals besides being profitable. I'm not aiming for a certain percentage of growth on- in a given year. If we're flat or even down, it's- it's okay. Like, this is okay. It's all about the long-term trajectory. It's not about this year versus last year.

    8. HS

      How do you feel about, kind of, what is measured improves, and also kind of driving teams with goals?

  7. 13:5319:04

    Goals are Overrated

    1. JF

      Um, I'm not a goal-driven person, so I don't drive teams with goals. Uh, I don't have goals really. I- I don't really believe in that. I know a lot of people do, but it's not my thing. It's never been my thing. My thing is, like, do the best job that you can, and why wouldn't you just do that? Like, what is it about the goal that makes you do the best you can? I think you should be, you know, intrinsically motivated to simply do the best you can. Um, so that- that's sort of my approach. There's not, like, a thing that I would do differently if- if there was some number ahead of me. In fact, I probably would hate it more because now I'm chasing something that's arbitrary, ultimately. I mean, people set up these targets, and I- we've done it in the past. You set up some target and you aim for it. It's like, "Why did we pick that number? Well, it happens to be a nice round number." So like, I'm- I'm, everything I'm doing now is based on some made-up number that happens to be a nice pretty round number? Like, and- and the- and the stress I'm taking on and the challenges we have are all based on this thing that we made up? Like, how about we don't make anything up and just do the best work we can on a daily basis, and that adds up, and let the chips fall where they may? I mean, that's kind of my- that's my approach, you know, for better or for worse.

    2. HS

      No, I get you totally, and I like that kind of, respectfully let's say, fair attitude. (laughs)

    3. JF

      Yeah.

    4. HS

      You could almost be a European. Um... (laughs)

    5. JF

      (laughs) Sometimes I try to be, yeah.

    6. HS

      But my- my question would be, like, with goals, if you don't kind of, not agree, but if you don't love executing in that fashion, how do you think about performance management, performance reviews, and ensuring getting the best out of people and measuring them against something?

    7. JF

      Yeah. Yeah, I think, um, first of all, management is really sort of the art of the individual.

    8. HS

      Mm-hmm.

    9. JF

      Um, so I think that you, when you evaluate people, we do performance reviews, like- like every company does, but we don't have metrics that we match people up against, um, because I don't think a lot of people actually have the power to change a lot of these things, and nor do I, nor is that the point. So, we know if someone's doing good work. Their team knows if they're doing good work. Their team knows where they're deficient. They should know where they're deficient. We should know where they're deficient. And we talk and- and- and discuss and encourage people to improve in this area or- or- or reward them, not financially, but like praise them or- or support them if they're doing well in this area. There's a lot of recognition that happens in the company. So, I think it's- it's about knowing the people you work with, and part of this is when you have a relatively smaller company, we have about 80 people, you- you can pay pretty close attention to the work people, individuals are doing, and- and- and you have a pretty good sense of how they're doing. And there is a- a relative nature to it, because there's other people at the company who do similar jobs, so there's some contrast there. But it's, you know, you look at the work. You look at the work, and you don't look at the- at the, um, the results that they aren't directly influencing. Like, for example, if someone's working on a feature in Basecamp, some improvement to the calendar, right? Like, that's not gonna drive any bottom line stuff, but it should be better because we want to make an improvement. Like, I can look at the quality of the work that they did, the details, the thoughtfulness, the code quality, the design quality, the copywriting, all the things that they're supposed to be doing well. I can look at those things and judge the person's work versus did that work have an effect on some other fake made-up number? I'm not interested in that second part of that conversation.

    10. HS

      I think it's a bit like inputs and outputs, and actually the output is the goal. And actually, what drives the output is the inputs, which is what really matters, which is what you're analyzing there. Do you see what I mean?

    11. JF

      Yeah. Yeah.

    12. HS

      The code quality.

    13. JF

      Yeah, it's the inputs that I'm... I mean, part of this too is like, um, one of the things we- we do is the first year is kind of a- a real big, I would say, I mean people are hired, but it's kind of a test. The main question we ask at the end of the first year is, "Would I hire this person again?" That's the real question that we ask after the first year. And we don't ask it out loud, but that's kind of what managers are asking themselves. And that question sums up a whole bunch of things. Um, and it's a- it's like you know- you inherently know the answer to that question if you are working with someone closely.

    14. HS

      What do you do-

    15. JF

      And-

    16. HS

      What do you do... Sorry, I'm too anxious.

    17. JF

      Yeah.

    18. HS

      What if you do if you wouldn't, but they're not bad?

    19. JF

      Yeah.

    20. HS

      They're okay.

    21. JF

      Yeah. Yeah, in many cases that can happen. I think ultimately it depends on the kind of company you wanna- you wanna run. We want people who we would rehire, and if someone's-... fine, but not quite right. They're better off finding a n- another opportunity somewhere else, where, where they're perfect for the, for the job. So sometimes there's these really hard decisions that are made around that period of time about, like, "This person's cutting it, they're fine, they're, they're good even, but they're not quite right for us. It's not that they're not quite right for them, it's that they're not quite right for us. And given the choice, we probably would not hire this person again, um, knowing what we know now." Could be cultural fit, could be skills, could be a lot of different things. They may have come in at a level where we thought they were better than they were gonna be. Maybe they'll be that good in three or four years, but when you can just hire someone else instead, like, maybe that's the choice. So that's what the first year is really about. It's like, "Is this person gonna, gonna fit in here and are they, are they on a trajectory that makes sense where we would hire them again?" That's, that's the, that's the gist of it. There's a lot of nuance

  8. 19:0421:18

    How to Give Negative Feedback

    1. JF

      in it, of course, but that's the gist of it.

    2. HS

      The thing I find really hard, honestly, is I'm a people pleaser. I like to be liked.

    3. JF

      Yeah.

    4. HS

      Um, I don't like giving bad performance reviews. I don't like criticizing people. Can I ask, having done this for 23 years, what advice would you give me on giving effective negative feedback? Not necessarily firing someone, but, "Jason, the work's not up to scratch. Continuously, you've let me down and it needs to get better." H- h- how do you advise me? Is it a shit sandwich? Help me.

    5. JF

      (laughs) Yeah, I mean, it's, it's not easy. I'm not great at it either. I think the best thing is to be very direct and show examples. So when you, when you say to someone, like, "Your work's not up to scratch," or whatever, it's like, "Well, why not?" So let's go through a few projects, let's talk about a few things that happened, and, um, I think the more specific you get, the better off the feedback's gonna be and the more someone can actually internalize it. Because if it's abstract, "It's not up to snuff, the quality isn't quite there," whatever, it's, it's just not enough to go on. So we tend to review projects and we're always trying to look at real things here. When we hire people, we actually hire them first for a week, uh, on a contract basis, one week, not in every position but in some, to actually do a project for us. And then we can actually look at real work together and discuss real work together to decide whether or not we can actually work together. So we're always trying to look at real stuff as much as we possibly can. I don't really care about resumes, I don't really care about a lot of that, uh, people's history, I don't care where they went to school, if they went to school, I don't care about any of those things. Let's look at the work itself. And so the same thing is true if you're giving someone feedback that's not great or, I mean, it can be helpful, but it might not be great to them, is, "Let's look at some work and let's talk about why this is the case." So for example, again, to get more specific, it might have been, "The last three projects we worked on, someone had to redo a number of the things that you did," or, um, "We had to go back, there was actually quite a few bugs associated with this, with this, d- d- you know, this, this piece of software," or, "The copywriting was very confusing and customer service kind of kept getting these questions about things, and this has come up a few times in the projects you've worked on." You know, so we wanna kind of point to real things, and that's the best you can do, but it still sucks, it's still hard. I'm not good at it. Other people are better at it than I am. Um, but I think you have to get real with these things. That's the only way to really give useful feedback.

    6. HS

      Can I s- uh, speaking of these hard conversations, I, I asked this of Brian at Coinbase, I'm sure you now

  9. 21:1827:53

    Basecamp’s Ban on Talking Politics at Work

    1. HS

      know where I'm going, um, I, I do worry about the over-politicization of leadership, um, and how leaders are now also kind of political figures within their own entities. You obviously made the political statement of not having politics within Basecamp, which backfired or seemingly backfired from kind of press. Can you just talk to me about that decision, and if there's anything you would do differently, and how it impacted your style of leadership?

    2. JF

      Yeah. So, um, this was a year and a half, a little long- old- longer than a year and a half ago, we made this call to say we're not talking politics at work amongst the pla- or i- in the places where we do the work. So for example, in Basecamp where we all work, we're not talking politics in Basecamp. If you wanna talk politics on Twitter, if you wanna talk politics in some private place, you can do that. But we're not mixing work and politics where we work. It was, it was met... We made a few other decisions at the same time, but that was the primary one, and it, it was met with a, a, a surprising amount of backlash. We were not surprised it would be controversial. Um, but ultimately about a third of the company quit, um, in a matter of, uh, was it... a week or two. We offered a very generous severance package. Some people weren't really... were already on the fence, and so they took that, but most people left because they disagreed with the decision. And, um, it was still, in our opinion, the right decision to make. We're still proud of the decision itself. Um, I think the hardest thing was that there are some people here who'd been here for 10, 12 years, um, who we were really close with and who left, and that was very hard. Um, it was hard to lose people who'd been here for a long time. It was hard to lose friends who, who, you know... this was sort of a line in the sand for them. So that was really personally difficult and there was moments over the next, I'd say, six weeks or so where I was part- I was really down, extremely down. Um, it was very, very hard. Uh, I, you know, relied on my family a lot, a therapist, you know, I needed some help to work through that because it was personally kind of devastating. Um, but it was still the decision, if I had to make it again today, I would make the same decision because-

    3. HS

      Would you do the- would you, would you do anything differently?

    4. JF

      Um, I think couple things that, that happened. So one thing is that we announced this publicly. So we're a very open company in this way. We typically talk about everything we do publicly anyway, but we announced this decision publicly, I think, about an hour after we announced it internally. And I think what happened was, is that there was a massive cascade of public pressure very quickly on employees before they even had a chance to really understand what was changing. And as you know, you know, on Twitter specifically, it was mostly Twitter, there's just, there's a, there's a mob mentality.

    5. HS

      Yeah.

    6. JF

      And people were directly attacking, uh, individuals who work here. Like, "How could you work for these XYZs?" You know, all the worst names in the world, right? And at a certain point, there's this massive pressure that's mounting on people who, they're like, "I didn't sign up for this. What is going on here?" Like, "Why couldn't we have talked about this internally first?" You know, so I think, I think we would've changed that, not that the news wouldn't have gotten out quickly probably anyway, but I think that we forced...... extreme pressure on people very quickly to make decisions. Um, so that was part of it. I think there are some other things that- that the language that we used to make the announcement felt a bit, um, punitive. Uh, it felt like we were punishing versus just, like, saying, "Look, we just can't do this anymore. Here's why." But it was a lot of, "No more, no more, no more." And I think that that felt like a punishment. People felt like we were coming down on them versus making a decision about the business. So, there's some details there, a bit of moral panic, in some cases, about, like, making decisions w- we probably wouldn't have made again. Um, but all- all in, um, I- I still, you know, it was still the right call for us. I can tell you, the company is in a significantly better place. We- we've- we've actually grown significantly bigger than we've ever been. Um, so we rehired a bunch of people and then have hired more since. At the time that happened, we were about 60. Now we're about 80, biggest w- we've ever been. A lot of new blood, a lot of new enthusiasm, uh, injection of new spirit and n- new approaches, and a- and a real focus on the work. Uh, and that's-

    7. HS

      I-

    8. JF

      ... sort of what we needed again. We needed a, sort of a kick in the face and a kick in the ass, basically. And that's what that ended up being.

    9. HS

      I did an episode with Dom Holland at Fast, just after Fast, 1-Click Checkout's, company went bust, and I- I got many death threats. Um, it was horrible.

    10. JF

      Yeah.

    11. HS

      Um, and it really, really hurt me. D- did it hurt you? And how did you actually get through that? I- I get, still, a lot of hate.

    12. JF

      Yeah.

    13. HS

      Advise me. You're the wise elder, Jason.

    14. JF

      (laughs)

    15. HS

      How do you get through the hate that you and I will get?

    16. JF

      Well, um, it- it did hurt, um, and it still, from time to time, hurts, um, when people say things about you that, you know, y- you just are so extreme and so, you know, just completely unnecessary, uh, uh, at the extremities. But one of the things I've just learned, simply, is that, you know, and this took a while, you know, I- I built up some thick skin prior to this. This sort of eroded some of it, and then you build it up again, is you just, you cannot let other people, uh, tell you how to feel. Um, and- and this is just a, you know, a lifelong practice to figure out how to go, "Yeah, okay." You know, that's- (laughs) that's a pretty strong opinion. I know me, I know who I am. I know what I believe. Um, I know why I made these decisions, and they weren't for those reasons. And you just have to go, "Okay." I mean, part of this, too, is- is not paying attention, frankly. Like, after this whole thing went down, I didn't look at Twitter for four or five months, um, because Twitter is just really where all the, like, vitriol and hate- hatred, deep hatred was, was happening. I got tons and tons of emails from people who were supportive, but people didn't want to say anything on Twitter because you know how it goes. Not many people are gonna stand up to your defense when- when- when people are attacking. And so... But I under- also, I understand the- the- the passionate s- uh, uh, sort of, I don't understand the hatred, but I understand the- the passionate eruption from- from people who disagreed with us. I get, I get that, and that's all fine. Um, but at some point, you just gotta realize, like, you cannot let other people make you feel a certain way. Like, your reaction is the only thing you're in control of. People can fling a bunch of things at you. How you react is the only thing that you can control. And, um, and that's something I've just been practicing and practicing and practicing and- and gotten much better at it. But it still, from time to time, stings.

    17. HS

      Now, this was a decision, a single decision.

    18. JF

      Mm-hmm.

    19. HS

      Uh, I think the most important thing, actually, is the framework around decisions, and you've written about decisions before.

    20. JF

      Yeah.

    21. HS

      I'd love to (laughs) bastardize,

  10. 27:5332:15

    Jason’s Decision Making Framework

    1. HS

      uh, you know, a lot of your hard work and ask, if you were to summarize your en- like, decision-making processes and frameworks today, how would you describe them?

    2. JF

      When I make a decision, I typically don't make it for now. I think about, "What will that probably feel like in a year?" This is sort of one way I- I- I do this, which is looking back on this decision, what... I try to project and imagine what it will feel like. There's a lot of decisions that you make to make, sort of, p- short-term pain go away, or to- to make conflict go away, or to make some disagreements go away. Um, and in the moment, it feels good to get that out of the way.

    3. HS

      Mm.

    4. JF

      But then, what are you stuck with? What do you have to live with after that? So, I tend to think about, what do you, what are we gonna live with on this decision? So, this comes down to even, like, complexity in software. Like, we could cut some corners right now and- and shortcut this just to get this thing done, but now we've got this shitty code in- in the code base. We've got this- this thing we're gonna have to live with. We're not gonna wanna go back in that area and- and mess with it 'cause it's- it's all messed up. And it, in the end, was not worth it, even though, in the moment, it felt like it was. So, I- I tend to think a lot about that. Um, I also think, like, "Why are we even making this decision at all?" That you can find yourself making a lot of decisions that don't need to be made. Um, that's something I'm always wondering about. Like, "Why are we even deciding on this?" Or, like, "What if no one decides? What will happen?" Like, "Will this just work its way out? Um, am I the right person to even make this decision?" Like, "Who's making this decision?" That kind of stuff.

    5. HS

      What's an example of, "Do we even need to make a decision?"

    6. JF

      There's probably... I'm trying to think of a- of a concrete example. Uh, this comes up all the time w- in software, which is a little bit, gonna be a bit abstract, but, or- or a bit inside 'cause it's sort of hard to explain completely, but there's a bunch of fea- let's say, you're making a feature of some sort. And you- you're worried about, like, "Should we have the, uh, should we have a- a button that does this, or- or a confirmation that does that?" Or, um, you know, "Should we explain this this way? Do we need a video to..." You know, all these- all this extra stuff that may not actually ultimately matter in the end, but there's a lot of discussion about it, a lot of- lot of consternation about it, a lot of extra work involved with it. And sometimes you're like, "You know what? It just, like, what if we just don't do this and see if anyone has any problems?" I'll give you, actually, here's a good example of this, um, specific, just came to mind. Hey World, which is a- our- our, so we have a email service called Hey, hey.com, H-E-Y.com, and everyone who uses hey.com also gets a personal blog.And to post to the blog, you just email world@hey.com and whatever you write there goes on your personal blog. It's published instantly. We had this big fear initially when we were launching this. It's like, "Gosh, um, like, do we need to have content moderating and do we need to approve posts? And what if post, someone posts something terrible?" And you've all... And there was lots of discussion internally about it and different people at different comfort levels about how strict we should be and should we not do it at all. And, and there was literally probably a month of discussion about this, mon, mon, bunch of different people. And, and then David, my business partner is like, "Why don't we just not do anything and see what happens?"

    7. HS

      (laughs) .

    8. JF

      Like, let's see. Is this... Are we manufacturing a problem? Like, if we need to solve this problem, we know how to, we can probably solve it, but why are we even worrying about it until it's a problem? And so we ultimately went in that direction, and turns out I think there's been one, like, piece of content that was maybe questionable or something in two years or whatever it's been.

    9. HS

      So you would ra- so you'd rather solve a problem than solve it before it becomes a problem?

    10. JF

      Yeah, I mean a lot of the things are like, let's wait and see if this becomes a problem. Some things you can anticipate more than others, but other things you just don't know, and I think a lot of companies spend a lot of time solving problems they don't have. Um, and then they solve them, they don't have them, and they think they, they did good work 'cause they don't have the problem, but they wouldn't have had the problem in the first place. So that's... And, you know, decision making, it's f- exciting to talk about decision making 'cause we always think about big decisions, but you hardly ever make big decisions. Most decisions are really small decisions, and if you're constantly making all these small decisions that you didn't need to make, that's a lot of time and energy spent on things that you didn't need to worry about. So we tend to say, like, "Let's see if something's going to be a problem before we actually solve it." And turns out we may n- not need to solve it at all. So that, that's maybe a better example or around

  11. 32:1534:46

    Jason’s Biggest Disagreement with his Co-Founder

    1. JF

      example of what we're trying to get at here.

    2. HS

      What was the biggest disagreement you and David have had around a cool decision?

    3. JF

      Um...

    4. HS

      And how did it get resolved? (laughs)

    5. JF

      Yeah, one of the biggest recent ones was, um, when we launched Hey, David was really adamant about launching the business version first, which is w- what was called Hey for Domains, and I was pretty stre- set on launching the personal version first, which is just @hey.com. And we battled over this for, I don't know, a month. You know, not like every day, but like it was, uh, up in the air for a month and, you know, strong, strong calls either way and whatnot, and in the end we decided to do, to do the personal version first, which I think was ultimately the right call. Um, but that was a, that was a pretty big, big one, and what David's point was that, like, launching a personal email service that people pay a hundred bucks a year for is a massive, like, risk because, like, people don't pay for email. Email is free, right? Businesses pay for email. Businesses are already used to paying for email, so why don't we make something that they're already used to paying for? And my angle was I think we can make something good enough, great enough, whatever, whatever you wanna call it, that people are willing to pay for. Um, and so that was the battle. How do we resolve it? In the end you make arguments and then a decision is made one way or the other, and a lot of it has to do with who, who's, who believes in it more essentially. Like, who really wants this more? Um, and then we, we do what we call trade. I mean, like, "Hey, look." This is like two friends going out for lunch. It's like, "I got this one. You get the next one." Does it always end up equal? No. It doesn't really matter though. At some point, like you, you work together for a long time, like, "You know, you really, really care about this one. Let's go in your direction this time." There'll be something I really, really, really care about. We'll go in my direction that time, and we kinda do this over the long term and it tends to work out pretty well. But one of the most important things about this is that we have this notion, and this is not our idea, other people have done this before, but this idea of disagree and commit.

    6. HS

      Mm.

    7. JF

      That when you eventually, when a call is eventually made and if you disagree with the decision, you cannot sabotage it. You've gotta commit to it because you still want, we still want what's best for the business, and even if you don't think it was the wrong call, you've gotta get behind it. You've gotta get behind it. And that's the only way to make this stuff work. Otherwise you have petty disagreements, sabotage, and that's, that takes the whole place down.

    8. HS

      23 years with David, of STINs.

    9. JF

      21 with David, I think, yeah.

    10. HS

      Okay. 21 with David.

    11. JF

      Yeah.

    12. HS

      That's a fucking

  12. 34:4637:40

    The Secret to Long Lasting Business Relationships

    1. HS

      long time with anyone, Jason.

    2. JF

      It is.

    3. HS

      Um, what is the secret to a successful business partnership in the way that you have when you think about your relationship with David? So few partners are together as long as you are.

    4. JF

      Yeah. I think it's a couple things. Um, one, we do different things. So David's an engineer. He's more on the technical side. I'm on the design side. So we're not battling over how to do the same thing, so I think that's important first of all. But we, we see business about the same way. I'd say we have like an 85 to 90% overlap on, like, our business point of view. So you need to have something core that's shared and in common, and I think the actual work itself you need to have separate skills on. I think that's very important. Second, I think we're able to just... I think we, we have strong enough senses of ourselves that we're able to battle hard and not take it personally.

    5. HS

      Mm.

    6. JF

      Um, that's something I think that's important. Um, I think also just fundamentally seeing, you know, again, like, business fundamentals in the same way, uh, is very important. Also, the fact that we don't see each other very often is very important. (laughs)

    7. HS

      Un- unpack that for me.

    8. JF

      David lives in Denmark.

    9. HS

      Wh- wh- so it helps that you don't see each other often?

    10. JF

      Yes. We rarely... Even, so we used to both live in Chicago for a while. Maybe once a week or every two weeks we'd see each other. We don't see each other very often. Um, I think that's helpful. Um, I think, you know, we talk all the time in base camp. We, we, we have a weekly call, um, you know, eh, that's enough actually, and I think that's a big part of it too. That we're both able to make decisions independently, that we don't rely on each other for everything, that we trust each other's individual skills and know that we're not necessarily great at what the other person does. But that, um, down the middle-... um, we share, you know, 85 to 90% of the same.

    11. HS

      I mean this nicely. Are you friends?

    12. JF

      Friends?

    13. HS

      Yeah.

    14. JF

      (clicks tongue) Yeah, we're friends. But I don't think like ... You know, we don't hang out as friends. Like, we don't ... Like, you know, we'll, we'll occasionally grab a dinner or something, you know, with their families or whatever. Very rarely. I mean, we're far away now so that doesn't happen at all. But when we were in the same city, we would occasionally do that. But like, we wouldn't just go hang out on the weekends or anything like that. It's, it's, it's ... We're not friendly in that way. Um, we-

    15. HS

      It's funny. I, I, I always said like, "I, I want a partner where I can, I can spend time with them on the weekend and go for dinner."

    16. JF

      Yeah.

    17. HS

      And someone said, "Uh, uh. You never want that. That is the ultimate no."

    18. JF

      (clicks tongue) Yeah. I think we, we have ... Again, we have shared, a lot of shared interests but very different lives.

    19. HS

      Yeah.

    20. JF

      And, um, think that's also very helpful.

    21. HS

      Well, I'm, I'm interested, you know, naturally, um, as a single dude, uh, looking, you know, to find love also, um, that's very different to being a great husband. (laughs) Uh,

  13. 37:4040:26

    The Secret to a Happy Marriage

    1. HS

      to be-

    2. JF

      Yeah.

    3. HS

      ... (?) in this way would be challenging for a marriage. Um, what have been your lessons on really being a great husband and having a great marriage?

    4. JF

      Well, um, you'd have to ask my wife if I'm a great husband. (laughs) I can't, I can't answer.

    5. HS

      (laughs)

    6. JF

      We've been married for nine years. I think we're doing pretty well. We have two kids. I think it's ... You know, um, my, my parents, when we got married, my parents wrote this really little short letter to us. Um, and, um, and there was a little bit of advice in, in the letter and I'm trying to remember exactly what it was, but it was, um, give each other space is a, is a primary fundamental thing. Um, and, you know, compromise but also give each other space. Um, and, and, and that, that I think is a really important thing. Um, now not everyone's that way. I think you have to know who you are.

    7. HS

      Mm-hmm.

    8. JF

      Um, but, um, you know, um, if, if, if you, if you're someone who needs quiet time to recharge or your wife is or your spouse is or whatever, you need to give them that even if that's not what you want. You know, really understanding what the other person needs is incredibly important in a relationship. I think, you know, uh, it's not really this idea of, of, of, um, you know ... Uh, uh, uh w- we're, we're, as humans, we're very egocentric and we're always thinking about ourselves first, and relationship is really about an us, it's, it's not about you. Um, that's a hard thing.

    9. HS

      Have you done, have you done each other's love languages?

    10. JF

      No. No.

    11. HS

      (laughs) D- uh, I'll send it to you afterwards. New York Times love languages. It's, uh-

    12. JF

      I remember hearing about this but we haven't done that.

    13. HS

      Yeah, it's, uh, it's important.

    14. JF

      Yeah.

    15. HS

      Final one and then we'll do-

    16. JF

      It's ch- it's very challenging though. I will say like, relationships in general are very, very hard, especially for, uh, people ... Like, I, I do like alone time. I do like my own space. Um, and it's hard especially when you have kids. We have two young kids, eight and four. It's, it's, it's very hard. Um, uh, but I think understanding and, uh, and, and, um ... The other thing I would say is it's really important in relationships and perhaps i- in business ones too is, is, is surprise. Um, positive surprise. Uh, doing things the other person wouldn't ex- wouldn't expect you to do. Um, that, that's always a very, uh, special thing to do. So, um, yeah.

    17. HS

      What was the most recent positive surprise you did for your wife?

    18. JF

      (laughs) Um, I, (laughs) um ...

    19. HS

      You're not getting away with that, Jason.

    20. JF

      Yeah, I know, I, I should've, yeah.

    21. HS

      You can't drop that one. (laughs)

    22. JF

      Yeah. Um, I think things like, um, deciding to take the kids for a weekend when, when she was having a s- a, a tough time. You know, uh, it was like, "Look, g- take some time for yourself. I got the kids." Like, things like that where, where w- where ... That's a, that's a hard thing to do. It's like, "I got the kids for the weekend." You know? She didn't ask me to do that but I could tell that she needed that. That kind of thing is, is, um ...

    23. HS

      Mm-hmm.

    24. JF

      It, that, that's kind of the kind of thing that

  14. 40:2642:30

    Parenting Advice

    1. JF

      I'm talking about here.

    2. HS

      Final one, I promise, and then we'll do a quick fire.

    3. JF

      Yeah.

    4. HS

      But, you know, obviously you mentioned your two children now. Um, and there's a lot you now know that you didn't know when you had them. If you were to advise me or younger self-

    5. JF

      Mm-hmm.

    6. HS

      ... on being a good father, what do you know now that you wish you'd known or you would advise your younger self?

    7. JF

      Well, I th- what I've kind of r- come to realize, there's a couple like fundamental things about kids, but kids are ... We have two so I've seen how just completely different they are. And again, just like I said earlier, art or, uh, management is the art of the individual. Parenting is as well. Like, our daughter needs different things than our son. Um, and, and, and like, and, and vice versa. So I think it's, it's very much paying attention to, to each individual and how they are, um, and not trying to sort of blanket, have a blanket way of being. Um, that's, that's kind of something I think it's very important. I think the other thing is, um, um, follow their curiosity is something that's really helped me, um, discover new things. Um, kids are incredibly curious. And they also ... You know, the other thing... Actually, you know what? Let me ... That's true but there's one thing that comes to mind right now which is one of the, the fundamental things you learn when you have kids is that you cannot make people do things they don't wanna do. I mean, you can r- really kinda make a kid get in a car if they need to, things, but you, you can see fundamentally that it's incredibly hard and there's a lot of negative externalities when you try to force people to do anything they don't wanna do. I think that comes, that comes through in business, it comes through in life, it comes through with your kids. But your kids really demonstrate that more than anyone else, and I think that's just a good fundamental lesson to understand when you're dealing with people.

    8. HS

      I, I, I couldn't agree with you more.

    9. JF

      Yeah.

    10. HS

      Um, I always feel like we could talk for a long time, Jason.

    11. JF

      (laughs)

    12. HS

      But I, I wanna move into a quick fire 'cause I'm aware-

    13. JF

      Sure.

    14. HS

      ... that I stupidly named it 20 Minute VC.

    15. JF

      (laughs)

    16. HS

      But I'm gonna say a short statement, you're gonna hit me with your immediate thoughts. I, uh, in terms of like favorite book and all that shit, what was the last bit of content that actually really stuck with you? Could be a magazine, could be a TV show, could be a movie, could be a book, but that actually

  15. 42:3045:07

    Eating Mushrooms

    1. HS

      changed the way you think?

    2. JF

      I listened to, uh, I, I recently re-listened to, uh, Pink Floyd Dark Side of the Moon, um, on some mushrooms, and that was a really extraordinary experience actually. Um, I, I, I, I heard ... It, it was an interesting reminder that-... the, the thing that you, the thing that you think you know, uh, y- you can, you can, um, experience in a different way. Uh, and, and that, that was just an example of that. But I've taken that experience and thought about that in terms of pretty much everything that I'm... You get very used to, like, the, the one note of something that you really know, and it turns out that there's, there's a lot of notes and a lot of angles on things that, that, that you're even, you know, that you think you know inside and out. So, that was something that was, uh, uh, quite, uh, an interesting experience.

    3. HS

      Mushrooms. Sorry, I'm, I'm in the UK. Like, good? Bad? Advice? Tips?

    4. JF

      Uh, what does the UK have to do with it?

    5. HS

      W- Well, I mean, I think it's illegal in the UK, my friend.

    6. JF

      Ah, I see. Well, you know, you could go to Jamaica and, and do it. Um-

    7. HS

      W- Wonderful.

    8. JF

      It's illegal here in different s- It's, it's legal in some places and illegal in others. Um, uh, what advice do you want?

    9. HS

      Like, how often do you do them? Any-

    10. JF

      Oh.

    11. HS

      Like, w- how does it make you feel?

    12. JF

      Not very often. I've, I've only really done them... I've done them, um, twice. Uh, I, I've done a high dose twice and then a low dose twice, basically. High dose meaning, like, five grams, like you have a blindfold on, and it's a completely inner experience for about six hours. It's a complete journey trip thing, um, which was absolutely profound. And, um, I came away from those experiences a different person, um, and also, uh, um, a, uh, um... I, I, I, I feel like everybody should do this once in their life, is kinda how I felt after I came away from those experiences. We can go into more detail on that separately if you want. But, um, I've done some low doses and just listened to music, like real low doses, just listened to music and just kinda relaxed. And what's really interesting is that you just, you, you, you recognize that, um, um, again, there, there, there's a lot more nuance to things, uh, th- than you typically would, would imagine, and that our brain and our waking brain right now, if we're, you know, both not on anything, uh, is really a filter. You're filtering the world into a way that you can perceive it on a day-to-day basis and live normally, but this is not necessarily the way things actually are. Um, there's, there's more to these things, but we kind of down-sample everything so we can manage. Um, and so it's kind of interesting when you take mushrooms, it kind of up-samples in a sense. It, it removes the down-sampling so you get to see a little bit

  16. 45:0745:53

    What would you like to change in the world of startups?

    1. JF

      more about what's out there, which is really pretty interesting.

    2. HS

      What would you most like to change about the world of startups? I'm sure it's, you, you can't avoid it. You see Twitter, you see Tech Crunch. What would you most like to change?

    3. JF

      Uh, th- the narrative, although I think it's actually changing a bit r- right now which is, like, you need a whole bunch of money. You need to grow as big as you can. It's all about scale, all that stuff. And I've been saying this for 20 years, so it feels a little bit boring to say again. But, um... And, you know, the truth is, is that actually most, most companies are self-funded, are bootstrapped, are small. That's actually the truth. But, but it sounds like that's not the case, um, it's, because, because there's so many big companies, um, or, or, or startups that get all the news and they raise a big bu- big round, and that's what a lot of people think they must do. And they come out of

  17. 45:5346:57

    Founder who Take Money off the Table

    1. JF

      school thinking that's the way to do it. So, I just wish that narrative was different. Um-

    2. HS

      Do you blame these founders for taking secondaries? Founders are getting demonized for taking secondaries. Do you blame them?

    3. JF

      Blame them for what, actually? Like-

    4. HS

      For taking secondaries.

    5. JF

      But-

    6. HS

      So, hot rounds, they took off 10 million off the table.

    7. JF

      Yeah. No. I, I, I, uh... My, my, my feeling... So, we, we did, we did something, not a secondary, but we did something similar with, with Bezos back in 2006. So, Jeff Bezos bought a small piece of my shares and David's shares. None of his money went into the business. The money went into my bank account and David's bank account. And this is to take some risk off the table, because we didn't know back then that... Basecamp was two years in. We didn't know if this thing was gonna last. It was, it was doing well, but gosh, what if this falls apart? Who knows? And, um, I, I'm not a fan of putting everything back into the business. I, I don't think that that's the way to run a business. I think you should take some money off the table as you go. You took a tremendous amount of risk to start this thing. You invested a lot of time and energy. Um, you could've done a million different things, but you did this. And so I don't,

  18. 46:5749:56

    Jason’s Risk Appetite

    1. JF

      I don't mind. I, I think it's very healthy and very smart to take some money off the table.

    2. HS

      How would you describe your attitude to risk today?

    3. JF

      I'm very comfortable taking risks. I'm actually more comfortable taking risks now. But I'm not comfortable risking the business. So, there's this idea of risk and then putting the company at risk. I'm not interested in putting the company at risk. But I'm interested in taking a whole bunch of risks and trying a whole bunch of things. I think this comes from, you know, like, David and I talked about this actually when we made that decision about the no politics thing. We said, "You know what? Um, it could happen that, um, this, like, sinks the business." Like, this could sink... This is before we made the decision. Like, we thought it'd be controversial, we didn't know how much, but it could sink the business. And we looked at it and we go, "You know what? If that is the case, that would actually be okay." It would suck. People would lose their jobs. That would all be bad. I'm certain people who worked here could get other jobs. We'd help people get jobs. It would suck for everybody. But it would also be okay in that we had a, at that point, a 21-year run, um, a wonderful business. We made a lot of impact in the industry. We took care of lots and lots and lots of customers. We generated lots of revenues, lots of profit, all the things. We've, we've put out books. We've done all the things. If it came to an end at that point, it would be okay.

    4. HS

      Mm-hmm.

    5. JF

      And so that's something I always think about. Um, again, I wouldn't want it to come to an end, but if it did, I'd be okay with it. And that gives me a lot of confidence and solace i- in taking more risk and being risky. And in fact, you know, I was actually talking to Brian over at Coinbase about this. He had a great thing. This wasn't about the politics thing, but we were talking about something else. He said basically, um, "The founder's job is to inject risk into the business." Um, because professional CEOs or when, when founders leave a business, businesses get very conservative, they don't take risks anymore. It's actually the founder's job to keep adding risk to the business.Um, and, and I've come to really believe that that's the case. 'Cause I can see that if I'm not pushing weird ideas or trying different things, like, those things wouldn't naturally be happening inside the organization. People's jobs aren't... People, people aren't built to take more risk in their job. It's not really what's rewarded ultimately in companies, um, unless it pays off. But risks typically don't. And so people tend to be more conservative. So it's my job to not be that.

    6. HS

      I know you don't have a board. But say you had a board, that's you, David-

    7. JF

      No. (laughs)

    8. HS

      No, just-

    9. JF

      But go ahead.

    10. HS

      Just roll with me, roll with me.

    11. JF

      (laughs) Yeah.

    12. HS

      You've got you, David, and you can add one person. Who would you add?

    13. JF

      Oh my gosh. What a great question.

    14. HS

      Could be, could be Bill Gates. Could be Barack Obama.

    15. JF

      Hmm.

    16. HS

      It could be...

    17. JF

      What a great question that is. Um-

    18. HS

      It could even be dead, like Arthur Rock, for me, would be like one of the greats. You know-

    19. JF

      Why?

    20. HS

      ... one of the founders of modern venture capital. Saw probably the most innovative set of entrepreneurs building probably the most challenging set of, like, core infrastructure that laid so much of what we take for granted

  19. 49:5651:25

    The Perfect Board Member

    1. HS

      today. Um, and the breadth of what he saw.

    2. JF

      So I don't, I don't know the person, but I'll describe who I'd like them to be maybe. Um, I would love to have someone with a radically different perspective that is convincing. (laughs) I, I'd like, I, I would like someone to be able to make a pitch and a case that we never would have made, a perspective we never would have had, something we never would have seen, and come away believing that that's a really viable alternative. That, that kind of person. I don't want another person like us. I don't want someone who's gonna just encourage us to do what we wanna do. I'd really want someone who, who I listen to and I go, "Oh shit, I hadn't thought of that. That is interesting." I like, um, insights like that. I, I, I, for me, insights are the most interesting things in the world actually. Um, when you, when you have or you hear something you haven't heard before or you haven't thought before or you thought you knew everything about something and you hear it from a different point of view, that, that stuff quenches me and I, I would love to have someone around who is like that. 'Cause David and I, even though David and I have a different point of view on some things, for the most part, we typically agree. And it'd be interesting to have someone who would really push us in a different direction who we would really respect and, and, and be surprised by.

    3. HS

      I think when you think you know, then you're really in trouble.

    4. JF

      (laughs)

    5. HS

      Uh, but fi- final one, my friend. Y- you mentioned earlier, you know, the kind of

  20. 51:2553:15

    Jason’s 10-year Plan

    1. HS

      long-term plans and how you think about running towards. What does Jason Fried in 10 years look like?

    2. JF

      Ah.

    3. HS

      If you were to paint that.

    4. JF

      Older, more wrinkles. I already have some. They're coming in, more gray.

    5. HS

      Are you s- are you still at base camp?

    6. JF

      10 years from now? No.

    7. HS

      Yeah.

    8. JF

      No. No. I think, um, um, I'm, I'm certain I'm not here in 10 years. Um, but I don't know where I will be. What I do know is this. I have no interest in ever starting another business.

    9. HS

      (laughs)

    10. JF

      And, and what I would say is, I might start a. Actually, I shouldn't say this. I have no interest in starting another company. I could see myself starting another business, and by that I mean just me. So I might do something that only I could do alone, you know, consulting. I don't know what it would be, right? Um-

    11. HS

      (laughs)

    12. JF

      But, but I don't, I-

    13. HS

      Does he need, does he need those dollars, those consulting dollars, Jason?

    14. JF

      No, no, it's not even that. It's, it's just like, you know, right. It's just keeping, it's like I like building. I like the creative process. So like, I c- I like to help people do that. Um, but I don't think I w- I, I'm certain actually, not don't think. I would never start another company with employees. I don't wanna feel r- what I don't wanna feel anymore is responsible for anybody else.

    15. HS

      Mm.

    16. JF

      I'm responsible for my family, my kids, my w- like all those things I'm responsible for in that world. That's enough responsibility for me. When I'm done with this, I've carried this responsibility of, you know, dozens and dozens and dozens of people and decisions and business and all that stuff. I don't want more responsibility when I'm done with this. So whatever I can do that doesn't feel like responsibility is something I would do.

    17. HS

      Jason, I always love our chats. Thank you so much for joining me today. This was fantastic and I, I really appreciate also it all being on the fly. Um, you were amazing, my friend.

    18. JF

      Thanks, Harry. It's always fun to talk with you as well. Thanks so much.

    19. HS

      You are a star, man.

Episode duration: 53:15

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