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Tim FerrissTim Ferriss

Ultimate Guide to Managing Executive Assistants and Delegating Like a Pro — Sam Corcos (4K)

Brought to you by: AG1 all-in-one nutritional supplement https://drinkag1.com/tim Shopify global commerce platform, providing tools to start, grow, market, and manage a retail business https://shopify.com/tim Resources from this episode: https://tim.blog/2023/09/20/sam-corcos/ Sam Corcos is the CEO and Co-founder of Levels, an a16z-backed startup that shows you how food affects your health using continuous glucose monitors and other biosensors. Levels: http://levelshealth.com/ Levels on YouTube: https://www.youtube.com/c/LevelsHealth [00:00] Intro [00:17] Delegation implementation and common mistakes. [06:37] Recommended reading for delegators, delegatees, and all humans. [09:05] Building a company culture that treats people like adults. [10:54] Tools for performance and communication accountability. [16:35] Why Sam considers Loom the “most important” tool in the kit. [20:20] Friday Forum. [23:34] Acclimating the recording-averse to Loom. [27:05] Organizing Loom recordings for later search and use. [33:18] Common challenges of sourcing and properly utilizing EAs/chiefs of staff. [39:14] Novelty-seeking and board games. [40:19] Vetting, pairing, and onboarding EAs and chiefs of staff. [44:51] News and social media sobriety. [51:57] Why does new employee onboarding take a month at Levels? [57:52] What most delegators wish they’d known as newbs. [1:02:09] Loom security and privacy concerns. [1:05:32] From to-do list to calendar. [1:10:53] How Sam skips the to-do list entirely. [1:14:31] General schedule and repeating items. [1:16:12] Scheduling stress reduction. [1:20:12] Selecting books and hosting themed salon dinners. [1:36:04] Calendly and related social hurdles. [1:37:50] Using email proactively. [1:40:42] The underrated power of hotkeys and shortcuts. [1:44:08] Scheduling spontaneity. [1:48:00] Calendar course correction. [1:49:40] How Sam utilizes multiple EAs. [1:51:37] Improvement growth for intermediate delegators. [1:58:58] The Working with Sam user manual. [2:04:33] Memo culture over meeting culture. [2:12:32] Fighting organizational entropy. [2:14:53] Raised secularly, what does Sam get out of theology? [2:24:02] The perils of postmodernism. [2:27:32] Network theory and relationship management. [2:42:00] The investor-swaying juice cart moment. [2:43:35] Metabolic health and the Levels mission. [2:47:52] Who is Levels hiring right now? [2:49:00] Physical over philosophical minimalism. [2:54:11] Why Sam has a travel-sized copy of the US Constitution. [2:58:16] Parting thoughts. Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 900 million downloads and been selected for “Best of Apple Podcasts” three years running. Sign up for "5-Bullet Friday" (Tim's free weekly email newsletter): https://go.tim.blog/5-bullet-friday-yt/ Follow the Tim Ferriss Podcast: https://tim.blog/podcast/ Visit the Tim Ferriss Blog: https://tim.blog/ Follow Tim Ferriss on Twitter: https://twitter.com/tferriss/ Follow Tim Ferriss on Instagram: https://www.instagram.com/timferriss/ Like Tim Ferriss on Facebook: https://www.facebook.com/TimFerriss/

Tim FerrisshostSam Corcosguest
Sep 20, 20233h 0mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:00 – 0:17

    Intro

    1. TF

      [upbeat music] Sam, nice to see you.

  2. 0:17 – 6:37

    Delegation implementation and common mistakes.

    1. SC

      You too.

    2. TF

      And I've been looking forward to this because I know how organized and systematic you are. [laughs] And for people who didn't see what came before this, I asked you, as I ask many of my guests, what would make this a home run or time well spent? And you said, "Well, I know that is one of the questions you like to ask based on my research, so let me open my notebook," and you had answers. And one of them that we can mention is an ambitious goal, but I think it's an achievable goal, which is to make this one of the most comprehensive tactical guides to delegation. And within that, there'll be a lot of process, and I have a lot to learn. Let's begin at the beginning. When did you start taking delegation seriously?

    3. SC

      Well, so true story, it came from reading your book almost exactly 10 years ago, and I posted an ad in Craigslist-

    4. TF

      Mm-hmm

    5. SC

      ... for an EA. I had nothing for her to do.

    6. TF

      [laughs]

    7. SC

      I just knew from reading your book that this is a skill that I need to develop.

    8. TF

      Mm-hmm.

    9. SC

      I ended up hiring Lori, who's, uh, been working with me now for 10 years.

    10. TF

      Incredible.

    11. SC

      Yeah. And I was just... She showed up, and I thought, "Okay, what, what do we do now?" [laughs]

    12. TF

      What now? What now?

    13. SC

      And I made it my mission to find things that I was doing that I could hand off to her. And some of the most common things that Lori does for me now are... Probably the most helpful one is during the course of the year when I see something that's makes for a really good Christmas present for somebody, I'll just send her a note and say, "Hey, get this for my brother for Christmas."

    14. TF

      Mm-hmm.

    15. SC

      And then, you know, November comes around, and there's the scramble to think like, "Oh, man, what do I get for Christmas?" And she says, "Well, you already purchased these 11 things for all these people." It's like, "Oh, cool." [laughs]

    16. TF

      Fantastic.

    17. SC

      Yeah, and she wraps them and she sends them, so it's pretty easy.

    18. TF

      Problem solved.

    19. SC

      Yeah.

    20. TF

      So 4-Hour Workweek, Craigslist, Lori, [laughs] and 10-year anniversary, pretty remarkable on a whole lot of levels. When you first began working with Lori, what were some of the mistakes that you made? Or if this is easier, broadly speaking, because you've seen so many examples of people attempting to delegate, you've seen the good, the bad, and the ugly. You've tried a lot of different things, but what are some of the more common mistakes that people make, or if we take a step back, why people don't delegate in the first place perhaps?

    21. SC

      Yeah, I, I've seen a lot of them. I think probably the first and simplest one is people have tried and they had a bad experience, and a lot of it comes from a lack of experience from the person who is doing the delegating. But sometimes it's just a bad match. We, we work with a lot of EAs at Levels, and we probably have to rematch maybe 30% of our, of our EAs just because there wasn't a fit. And a, a specific example of that was Zach, our head of legal.

    22. TF

      Mm-hmm.

    23. SC

      We paired him with an EA. Really didn't see any improvement there. And so we asked him how it's going. He said, "Ah, it's fine." And then we decided let's just try-

    24. TF

      Everything's fine.

    25. SC

      Yeah. [laughs]

    26. TF

      It's fine.

    27. SC

      Exactly.

    28. TF

      [laughs]

    29. SC

      So we decided, all right, let's rematch. Maybe we'll find somebody who had a legal background in the Philippines.

    30. TF

      So rematch, just so-

  3. 6:37 – 9:05

    Recommended reading for delegators, delegatees, and all humans.

    1. TF

      Are there any... We're gonna bounce around a lot.

    2. SC

      Yeah.

    3. TF

      And, and we are gonna zoom out to the company level in a second, but read these books. Are there any books that you strongly recommend or require as reading for two groups: people in the company, so employees, and then EAs of people who work in the company, or your EAs?

    4. SC

      Hmm. We don't have a required reading list for the EAs. We have a strongly recommended reading list- [laughs]

    5. TF

      [laughs]

    6. SC

      ... for a lot of people at the company.

    7. TF

      All right.

    8. SC

      And we have a-

    9. TF

      What's- what does the strongly recommended reading list look like?

    10. SC

      So we actually, we have a team book club every month where we read these books, and we've been around long enough to where we've recycled some of them and they've come back up. Some that really come up a lot are No Rules Rules, which is the book on Netflix culture. 15 Commitments of Conscious Leadership is another one, which I know you're familiar with.

    11. TF

      Yes, indeed.

    12. SC

      Another one that I know you're familiar with is Nonviolent Communication.

    13. TF

      Mm-hmm.

    14. SC

      Which really should just be required reading for all people. [laughs]

    15. TF

      For all humans. All humans.

    16. SC

      Yeah.

    17. TF

      Yeah.

    18. SC

      Yeah. I have found one sticking point with that book is the title.

    19. TF

      Mm-hmm.

    20. SC

      Like, I, I recommended it to a friend who had the exact situation that this book was meant to solve, and he said, "Well, the problem I'm dealing with doesn't involve any violence." It's like, no, no, no, it's not the point. It's, it's, it's really, it's about non-threatening communication. It's about how do you have these conversations without triggering that fight or flight mentality.

    21. TF

      Yeah.

    22. SC

      So.

    23. TF

      Great framework, not the best branding. [laughs]

    24. SC

      Yeah, exactly.

    25. TF

      If you were, I'm gonna explore this a little bit more and there may not be much to explore, but if you were to have your EAs read books that you think would aid them-

    26. SC

      Hmm

    27. TF

      ... in their capacity in as a, being a remover of obstacles, a smoother and creator of process perhaps, are there any that would, would come to mind? Maybe they're the same books. I mean, who knows?

    28. SC

      Hmm. It would probably be something process-oriented.

    29. TF

      Mm-hmm. Like the Checklist Manifesto.

    30. SC

      Yeah.

  4. 9:05 – 10:54

    Building a company culture that treats people like adults.

    1. TF

      All right, so company level, levels.

    2. SC

      Yeah.

    3. TF

      What are, what are some of the things that might surprise people out there who have image, image A of what a startup or company looks like?

    4. SC

      It'd probably be a lot of things. [laughs]

    5. TF

      Yeah.

    6. SC

      We, we're trying some pretty radical experiments in organizational design. For example, we're building in public. All of our investor updates from the beginning of the company, from day one, are public on our website.

    7. TF

      Mm-hmm.

    8. SC

      All of our team all-hands-

    9. TF

      Mm-hmm

    10. SC

      ... weekly are public on our website. We're super transparent. There's a, a phrase that we took, I think this might be from Netflix, which is, "Treat people like adults."

    11. TF

      Mm-hmm.

    12. SC

      And I would say a lot of our values as a company are really downstream of treat people like adults.

    13. TF

      Mm-hmm.

    14. SC

      When thinking about company culture, what that means-

    15. TF

      Mm-hmm

    16. SC

      ... I really think that it means it is the set of assumptions you can make about the other people around you that you work with without having ever interacted with them before.

    17. TF

      Mm-hmm.

    18. SC

      If you can make the assumption that they are not going to gossip, that they are going to close the loop on your communication so you don't have to set reminders for yourself, all of the things-

    19. TF

      Can you give me an example of that?

    20. SC

      Yeah. So the closing the loop would be something like when you deliver something, you then send them a message saying, "I completed this task."

    21. TF

      Mm-hmm.

    22. SC

      And so it just... The more of these open loops you have where you have, where you feel like, "Hey, did you ever finish that thing?" And it's like-

    23. TF

      Exhau- exhausting.

    24. SC

      It's exhausting, exactly. And so just closing the loop on that. And some of these are very simple things.

    25. TF

      So the assumption is people will carry something to completion-

    26. SC

      Yeah

    27. TF

      ... once you have assigned it.

  5. 10:54 – 16:35

    Tools for performance and communication accountability.

    1. TF

      Couple of questions just on those two as examples.

    2. SC

      Yeah.

    3. TF

      So I feel like treating people like adults is one thing, but there are a lot of gossipy, mean-spirited-

    4. SC

      Right

    5. TF

      ... unreliable adults in the world, so probably, like, mature, competent adults, right?

    6. SC

      Mm-hmm.

    7. TF

      And are there tools that you use to remove some of the need to have follow-up, or is it just assumed that people will have their own set of tools, like an Asana or something else? I'm just wondering how much the toolkit enables you to help treat others like responsible adults.

    8. SC

      There are definitely tools that can help. I would say that a lot of it is really just a commitment to following through.

    9. TF

      Right. These are the expected outcomes/responsibilities/commandments-

    10. SC

      Mm-hmm

    11. TF

      ... of being a responsible adult.

    12. SC

      Yeah.

    13. TF

      So these, this is just table stakes for the culture that-

    14. SC

      Yeah

    15. TF

      ... we're building here.

    16. SC

      Yeah, like, we, we have a, a memo internally, uh, which is I think also published externally. Most of our strategy memos are published externally. But it says that, "A lack of communication is a lack of performance."

    17. TF

      Hmm.

    18. SC

      And this is something that I think a lot of people mistake, is they say, "Well, I did my job, I just didn't communicate well."

    19. TF

      Mm-hmm.

    20. SC

      And they say, "Well, you know, I... Sure, I can always improve my communication," and they feel like it's not an important thing.

    21. TF

      [laughs]

    22. SC

      And we've really taken that- To say, "Okay, well, your communication is part of your performance."

    23. TF

      Mm-hmm.

    24. SC

      "So I don't care how well you think you did on this task, if you failed to communicate it while it was being done, and you failed to close the loop to let the people know that it was done, who you're accountable to, that is a failure of performance, not a failure of communication as, like, a separate category."

    25. TF

      It's like an ancillary-

    26. SC

      Yeah

    27. TF

      ... minor component. It is an integral-

    28. SC

      Yeah

    29. TF

      ... part of the entire puzzle of performance.

    30. SC

      For sure. And I, I would actually add to the tools for the gossipy part as well, that we record all of our meetings.

  6. 16:35 – 20:20

    Why Sam considers Loom the “most important” tool in the kit.

    1. TF

      So for people listening, and we are gonna come back to delegation and many aspects of delegation, but all of these things tie together, right?

    2. SC

      Yeah, totally.

    3. TF

      They're, they're interdependent pieces, and I feel like they're also, as [laughs] loathe as I am to use this word, but I do use it occasionally, which is synergistic, right? These, these have a multiplicative effect in some respects. Let's talk about one tool, and neither of us have any vested interest in this, this company or this tool, Loom, because I had used Loom occasionally, and then I saw your use and your company use of Loom [laughs]

    4. SC

      [laughs]

    5. TF

      ... which took it to levels I, I could not even previously imagine. So how, how is this used? And maybe then you can just touch on a few other tools, and then we're gonna come back to EAs and I think we'll probably start with sourcing and then move on to-

    6. SC

      Yeah

    7. TF

      ... better delegation. But from a tool perspective, let's start with Loom, what it is, how you use it, and then maybe you can mention a few others.

    8. SC

      Loom is probably the most important business enablement tool of the last five years, certainly in my experience. It's a very simple tool, which is it's a low-friction way to record your screen and then some sort of an async message. You have a picture of yourself. You can record your screen, and it is really easy to record a Loom.

    9. TF

      And it is ready to share-

    10. SC

      Yeah, inst-

    11. TF

      ... pretty much instantaneously-

    12. SC

      Mm-hmm

    13. TF

      ... when you finish recording.

    14. SC

      Yeah.

    15. TF

      So there's no lag time for uploading something to a sharing service.

    16. SC

      Totally. And what's interesting about using this sort of tool is that anything that is in the form of content- Scales effectively infinitely in a way that in-person time or phone calls do not. Content scales, time does not. It's pretty simple calculation. But what's interesting is there's a mental shift that needs to happen for people where it reminds me of in the, in the early days of radio, you maybe know some of the history of this, of the first radio programs were just theater plays read out loud on the radio, 'cause they didn't know what to do with this new medium. It made no sense. And then eventually they figured out instead of copying our old ways, we can create new patterns that amplify this even more, and I think this is where we are with a lot of these remote work tools. So whereas in the past pair programming was you have to two people sit behind each other and you watch each other code and you talk and you're doing it at the same time, or you have a really good programmer who's just doing his normal workflow, recording on a Loom, and he's just narrating what he's thinking while he's doing it, and then the other person can watch it at two and a half x, they can pause it, they can rewind, they can take notes. You don't have to do this live. It's a piece of content. And then every engineer at your company forever into the future can see this same piece of content. And so the, uh, there was a, a really interesting example recently where I, I shared something with somebody externally, and they were commenting on like, "Well, this, this is a failure 'cause only 40 people watched this." And I said, "This was an internal meeting. Could you imagine, like, if we had an internal meeting with 40 people in it? You would say, like, that was a lot of information being transmitted." But there's this cognitive thing of like, well, if it's a piece of content, it needs to get like a million views or it's a failure.

    17. TF

      [laughs] Right.

    18. SC

      Yeah.

    19. TF

      So just, just out of curiosity, if, if you're open to saying-

    20. SC

      Yeah

    21. TF

      ... I mean, you're open to saying a lot, but I understand if it's not everything. What was the Loom of the 40-person meeting that was shared externally, or why was it shared externally?

  7. 20:20 – 23:34

    Friday Forum.

    1. SC

      The Loom that was shared was one of our Friday Forums.

    2. TF

      Mm-hmm.

    3. SC

      It was a-

    4. TF

      What is a Friday Forum?

    5. SC

      Oh, sorry. That's our team all hands. We do it every week on Fridays.

    6. TF

      Mm-hmm.

    7. SC

      And-

    8. TF

      How large is the team now?

    9. SC

      The team's 40, 50 people.

    10. TF

      40, 50 people. Mm-hmm.

    11. SC

      And so many people show up live, so they don't watch the recording, so that's fine, and then some people watch it after the fact. And so we also have a number of all of our memos, we also use Notion pretty religiously. Once you learn how to use the Notion database features, they're actually extremely powerful in the amount of leverage you can get from it. And we- all of our memos have a summary Loom at the top, any, any sort of meaningful memo. And so somebody will do a five-minute walkthrough of something that they wrote, and many people just watch those Looms. So it's another thing where y- people can share.

    12. TF

      What is the format or the agenda for the Friday Forum?

    13. SC

      So every meeting obviously has some intent, and I think it's important... Where, where a lot of people fail is they, they lose the intent of the meeting. And so we, we even explicitly state this at the beginning of our Friday Forums, which is this is the place where we celebrate the wins of that week. And so we have a, the first few minutes are highlights of the week, then we have usually a special guest, which is oftentimes one of our members from the company who's had some really positive experience using our product. Then we do highlights from maybe the growth team, maybe highlights from the product team. So the goal is to have people feeling really good about the things that were accomplished during that week.

    14. TF

      Mm-hmm. And how long is it?

    15. SC

      It's typically an hour, and we do at the end maybe 20 minutes of personal updates, like personal highlights on the week.

    16. TF

      And just for disambiguation for folks who may not be familiar with the company, members, you mean customers?

    17. SC

      Yeah. Yeah, yeah.

    18. TF

      And then if we double-click on both Loom and Notion again-

    19. SC

      Mm-hmm

    20. TF

      ... because I, I really feel, and I have doubled, tripled, quadrupled my use of Loom, I have a couple of specific questions. Where have people been doubtful, employees, of using Loom? And I think you gave me, and we can always clip anything out of this-

    21. SC

      Yeah

    22. TF

      ... interview, right? But an example of a videographer, a video editor-

    23. SC

      Yeah

    24. TF

      ... at one point, which I think is a good example, so maybe you could give that. And how do you make these easily searchable and findable? Because what I find is I use Loom most often in a one-off capacity, say running through a Google Doc, and I don't want to add 75 different comments.

    25. SC

      Mm-hmm.

    26. TF

      So I will use that as a way to give my verbal feedback and next actions. Saves a ton of time, or at least a ton of my time.

    27. SC

      Mm-hmm.

    28. TF

      And [laughs] so I'd love to know perhaps some use cases which will challenge what people might perceive as what is possible or not possible with a tool like Loom, and then I'd love for you to say a little bit more about why you use Notion instead of other options, like what the use case is predominantly.

    29. SC

      Yeah.

    30. TF

      And I'm speaking as someone who doesn't really use databases.

  8. 23:34 – 27:05

    Acclimating the recording-averse to Loom.

    1. TF

      at this point.

    2. SC

      Yeah. I think one of the things with Loom, part of the assumption is that one of the rules that we really try to push people for is only ever do one take. Just do one take. Because so many people when they start using it as a tool, they stumble and say, "Oh man, I have to re-record it," and they'll do eight takes for something that really did not need to be. And so we really try to push people towards if you're in a meeting and you stumbled over your words, nobody would care.

    3. TF

      Mm-hmm.

    4. SC

      And they also don't care-

    5. TF

      [laughs]

    6. SC

      ... that you did it in a Loom. So just relax. It's fine. A lot of my Looms I have, like, m- multiple minutes in a row of pausing, of just thinking, "What would I do here?" And then in, in, in people's minds it's like, "Oh my God, this is so uncomfortable. I'm on a recording and there's this empty space." ... you know, what are, what are they going to be thinking?

    7. TF

      Mm-hmm.

    8. SC

      But if you're in a meeting, that would be totally normal.

    9. TF

      Mm-hmm.

    10. SC

      And so one of the things that we do during our onboarding, I believe it's now week three of our one-month onboarding for new employees, is the entire week, third week, is async week, where you are only allowed to do verbal and, and, uh, video recordings for communication. You're not allowed to write anything. You're not allowed to type anything. So if you want to say, "Hey, great job," you have to record an audio note and you have to send that, or you have to do a Loom of yourself saying, "Hey, that was good work. Thank you," and then that's it. And just get used to that.

    11. TF

      How do they send the audio note?

    12. SC

      So Loom also has an audio feature.

    13. TF

      I see, audio only.

    14. SC

      Yeah, if you... I think it might only be on mobile, but you can do an audio note on Loom Mobile.

    15. TF

      Mm-hmm.

    16. SC

      And yeah, it's, it's really, really uncomfortable for people. This is why the forcing function was we had to make this part of onboarding because it was so strange for almost everybody.

    17. TF

      So what would you say to folks, and then maybe we'll talk about the, the video example as another training tool.

    18. SC

      Mm-hmm.

    19. TF

      Uh, but what would you say to people who have the visceral reaction of, "I'm very fast at reading. Video and audio memos are really slow"? And I saw this meme going around, this guy standing [laughs] on a street corner with this big sign over his head, sort of like someone who would ask for money, but it said, "No, I will not listen to your three-minute voice memo." So how would, how would you address that concern that this is just going to end up taking more time during like, let's say, an async week? And maybe that's okay because-

    20. SC

      Yeah

    21. TF

      ... you're really just trying to force people to get used to working asynchronously, but what are, what are your thoughts?

    22. SC

      I mean, that's definitely the case. The, there's, there's no perfect medium. The, the medium matters depending on the message that you're trying to communicate.

    23. TF

      Mm-hmm.

    24. SC

      And so long form memos should be in writing-

    25. TF

      Mm-hmm

    26. SC

      ... because you're going to skip over, you're going to find the parts that are relevant. Writing is a tool for thought-

    27. TF

      Mm-hmm

    28. SC

      ... and doing these audio notes is a different tool to convey different types of information.

    29. TF

      Yeah.

    30. SC

      And so I think the, the short answer is you should use the right tool for the job.

  9. 27:05 – 33:18

    Organizing Loom recordings for later search and use.

    1. SC

      Yeah.

    2. TF

      All right. Would you mind describing, since I've teased it excessively now, but the, the video editing example-

    3. SC

      Yeah

    4. TF

      ... and then how you make things searchable because, for instance, I have a very small team, but at one point I was curious as to how people were currently tracking tasks and projects-

    5. SC

      Yeah

    6. TF

      ... because people have a good amount of flexibility, and there are pros and cons to that. We have used a lot of, say, Asana in the past, but some employees work differently and have different approaches, so I wanted them to capture a Loom of their flow. And if you were to ask me right now, gun against the head, "You have to find all of those Looms [laughs] within the next 30 minutes," I would, I would be concerned for my safety, right?

    7. SC

      [laughs]

    8. TF

      I, I might not find them. So the, the video example and then how you organize things or naming conventions maybe, I have no idea, organize these Looms such that you can find them later.

    9. SC

      So one of the things I would say is that I probably record... In fact, I know the statistic. I probably average about 10 to 20 Looms per day I record.

    10. TF

      Mm-hmm.

    11. SC

      And to be perfectly honest, I maybe share half of them.

    12. TF

      Mm-hmm.

    13. SC

      A lot of them, I just turn it on because maybe I'll want to use that information. It is, it is costless to record a Loom, and so if nothing happens, then I just... Nothing happens. It, it costs nothing. It costs me nothing to record it. It costs me nothing to not share it.

    14. TF

      Mm-hmm.

    15. SC

      The searchability, it has not been an issue for at least the Looms that I record because they tend not to be things that I would come back to. They're more in the moment things.

    16. TF

      Yeah.

    17. SC

      I would be willing to bet though that over the course of the next maybe 6 to 12 months, that as these AI tools continue to get better, search is the most obvious use case for this.

    18. TF

      And as far as I can tell, in the last, I don't know when this started, maybe month or two-

    19. SC

      Mm-hmm

    20. TF

      ... Loom has already begun to auto title-

    21. SC

      Yep

    22. TF

      ... your videos based on, I assume, I'm not sure if it's AI, but some type of-

    23. SC

      Transcripts

    24. TF

      ... transcript.

    25. SC

      Mm-hmm.

    26. TF

      Exactly.

    27. SC

      Yeah, and so there will be a point in the future where you can say, "Hey, can you find me that video that I did with this specific person where we talked about this?" And it'll definitely be able to find it.

    28. TF

      Yeah.

    29. SC

      So I think, I think some of that will just be solved.

    30. TF

      So my laziness has a shelf life-

  10. 33:18 – 39:14

    Common challenges of sourcing and properly utilizing EAs/chiefs of staff.

    1. TF

      so how many, how many EAs would you say work with you and your employees?

    2. SC

      I think I personally have four right now that just work for me doing my tasks. I think we have maybe 20 in the whole company.

    3. TF

      All right. [laughs] So what are the options or the better op- some of the better options for sourcing EA talent?

    4. SC

      Mm-hmm.

    5. TF

      And the follow-up, 'cause I like to just put things in the hopper so it can gestate, when you talked about rematching, I'd be curious as to how you assess and decide when to kind of keep or cut someone, if there's a process for that. I imagine it's not purely subjective feel, but I'd be, I'd be curious to learn more about that. So sourcing, what are, what some of the better options are, and then how you evaluate.

    6. SC

      There are several ways you can go about sourcing. I've always found the best way to do it is to work with an agency. We work with Athena.

    7. TF

      Mm-hmm.

    8. SC

      They're an agency out of the Philippines. They're really the, the higher end of agencies, and they cost more, and so it really depends on how, how much you value that.

    9. TF

      Mm-hmm.

    10. SC

      Other options would be you can source them directly, which tend to be cheaper. I think Athena's $15, $20 an hour typically.

    11. TF

      Mm-hmm.

    12. SC

      And you can find talent for $5 an hour if you, if you source it yourself.

    13. TF

      How would you source that directly for people who were interested in the lower end?

    14. SC

      Yeah. So Upwork is a place where people often go to find them. There's also another agency that's sort of on the, they're on the cheaper side, which is Shepherd.

    15. TF

      Mm-hmm.

    16. SC

      And my friend Nick is involved with them. They're, they tend to be more like $5 an hour-

    17. TF

      Mm-hmm

    18. SC

      ... but it requires a lot more overhead. So they, they don't have their own management team. It's really you and them figuring it out as opposed to having more of a structure around it.

    19. TF

      And Athena came up numerous times for me in the last, I want to say, year and a half, and they were actually very, very helpful for sourcing my new chief of staff-

    20. SC

      Oh, cool

    21. TF

      ... which maybe at some point, whenever it makes sense, we could delineate maybe EA from chief of staff-

    22. SC

      Yeah

    23. TF

      ... and what those terms mean. And in the case of sourcing through Athena, those are all full-time employees?

    24. SC

      Mm-hmm. Yeah.

    25. TF

      How many of them are dedicated to one person as opposed to spread across multiple employees?

    26. SC

      We have this concept of an EA pool-

    27. TF

      Mm-hmm

    28. SC

      ... where it's just available EA talent for whoever needs a specific task done. Over time, they become more and more dedicated as a specific person needs more consistent resourcing-

    29. TF

      Mm-hmm

    30. SC

      ... or as context becomes more relevant. We recently shifted one of our EAs to full-time on product support, who was in the EA pool, but we just have enough tasks now in product that it makes sense to have a single person with dedicated context on that. So I don't know the specific numbers. I would guess we probably have 15 dedicated and maybe 5 in the general pool at this point.

  11. 39:14 – 40:19

    Novelty-seeking and board games.

    1. SC

      And so I, I'm just relentlessly novelty seeking-

    2. TF

      Uh-huh

    3. SC

      ... and I just, I, I really struggle to do any task more than just a handful of times. I play a lot of board games. I can usually only play a game maybe five or 10 times before I've figured out the strategy, and then it's boring. It's just like-

    4. TF

      [laughs]

    5. SC

      ... a mastery thing of, okay, well, I already know how to win most of the time, and now it's just how do I get slightly better?

    6. TF

      So gamers, find the Goodwill closest to Sam, and you will find a lot of overflow of perfectly good board games. I got it. Okay. How do you choose your board games?

    7. SC

      Mostly through recommendations.

    8. TF

      But what are the criteria the recommenders are using before passing to you?

    9. SC

      I really only play complex strategy games.

    10. TF

      Mm-hmm.

    11. SC

      So they, they tend to be, you know, the, the Euro style games. It tends to be games that if they come recommended from somebody who I know is a very serious board gamer, then I know it'll be good.

    12. TF

      Mm-hmm.

    13. SC

      So I'm playing, uh, Twilight Imperium on Sunday, which is like a full day long board game.

  12. 40:19 – 44:51

    Vetting, pairing, and onboarding EAs and chiefs of staff.

    1. TF

      Mm-hmm.

    2. SC

      So yeah.

    3. TF

      [laughs] Sam's recreation. You know, I do love tabletop games. It's something that we could geek out on maybe, maybe over dinner. [laughs]

    4. SC

      Sure.

    5. TF

      But I'm, I'm very into it. I don't want to take us too far off script. [laughs] So we're talking about EAs and chief of staff. Also, I mean, I think the degree to which things overlap, for me it's always been important that, like, no task too small, no task too big, in part because the org size is so small, right? It's like I have three full-time employees. [laughs] But let's come back to both, say, onboarding and how you assess performance and decide on pass, fail, go, no go with EAs. What is, what does the process of vetting and pairing and onboarding look like?

    6. SC

      So onboarding is super important. People put a lot of time into recruiting.

    7. TF

      Mm-hmm.

    8. SC

      They'll put $50,000, $100,000 into hiring somebody, and then as soon as they start, they just, like, throw them into the deep end and hope for the best. And so having really good onboarding is super important to that attach rate of people really being able to work effectively.

    9. TF

      Mm-hmm. Attach rate is, I guess, is that the same as retention?

    10. SC

      Yeah. I, I mean, however-

    11. TF

      Mm-hmm

    12. SC

      ... different companies have different definitions of attach rate. But yeah, it's like the ability to, to work adequately with an EA.

    13. TF

      Mm-hmm.

    14. SC

      And so I think one of the most important things is setting super clear expectations early.

    15. TF

      Mm-hmm.

    16. SC

      Setting good process really helps as well. Something that we look for is proactivity, somebody who goes out of their way to reduce your workload instead of somebody who creates work for you.

    17. TF

      How do you test for that? Can you test for that in the vetting process, or do you have to kind of wait and see?

    18. SC

      You might be able to test for it. I haven't... This is one of the, the benefits of working with an agency is-

    19. TF

      They get to know what you need.

    20. SC

      Yeah. And specifically, Athena was started by Jonathan from Thumbtack, and- His whole thing is 10X delegation.

    21. TF

      Mm-hmm.

    22. SC

      So they have a whole internal training program to try to make them be more proactive, as opposed to hiring somebody who's completely fresh and you have to teach them all of these things.

    23. TF

      Mm-hmm.

    24. SC

      So this is the, the trade-off of time. You can train somebody up and it would be less expensive, but it requires more overhead at the beginning.

    25. TF

      Mm-hmm.

    26. SC

      I think the nature of how you train them and how you set these expectations, one of the best ones, this is another tactic, is the playback, which is you set a task and you say, "Repeat back to me," and this is almost always done in a Loom, "Repeat back to me how you will do this task."

    27. TF

      Mm-hmm.

    28. SC

      And oftentimes when you're just getting started with somebody, they'll propose how they're gonna go about it, and it's completely wrong.

    29. TF

      [laughs]

    30. SC

      And that's okay.

  13. 44:51 – 51:57

    News and social media sobriety.

    1. TF

      It's a great mission, great mission. I want to talk about information inputs.

    2. SC

      Yeah.

    3. TF

      This may be a good place for a sidebar on this. So avoiding slot machines.

    4. SC

      Yeah.

    5. TF

      News sobriety.

    6. SC

      Yeah.

    7. TF

      You know, the term I've used, which I think is probably quite similar, is sort of the low information diet, right? But what does... what is news sobriety, and what does that mean for your day-to-day, month-to-month experience?

    8. SC

      I've been fully news sober for almost 10 years.

    9. TF

      Mm-hmm.

    10. SC

      And I, I read Ryan Holiday's book, Trust Me, I'm Lying.

    11. TF

      Mm-hmm.

    12. SC

      That really frightened me about the state [laughs] of the media and convinced me... This was originally just a one-month experiment. I said, for a month I'm going to consume no current events in any form. No, no news, no, no television, no articles, no social media, and instead I'm just gonna try a one-to-one replacement of reading books during that time period. And I read eight books that month, which was more than I probably read in the previous five years.

    13. TF

      [laughs]

    14. SC

      And everything about my life was better. [laughs]

    15. TF

      Mm-hmm. Mm-hmm.

    16. SC

      I, I physically felt different. Like, I felt less anxious during the day. And it was interesting when you have that separation for long enough.

    17. TF

      Mm-hmm.

    18. SC

      I have friends who are panicked about something that they heard, and I would find myself asking, "But does that matter?" [laughs]

    19. TF

      Mm-hmm.

    20. SC

      And it's like, wow, I would've been in the same frenzy if I was paying attention, and it, it really doesn't matter. Almost none of these things are important, so.

    21. TF

      So how do you... And maybe that is the answer, but I'm curious since I've received this answer when implementing this to probably a lesser extent. The question of, like, how do you stay informed? Aren't you worried that you're missing important things or some variant of that? I have my own way to respond to that, but I'm curious how you respond to it.

    22. SC

      Yeah, I think it is one of the coups of the news industry broadly, that they've managed to convince people that watching the news is a, is what responsible citizens do.

    23. TF

      Mm-hmm.

    24. SC

      In much the same way that the orange juice lobby convinced people that orange juice is healthy 'cause it has vitamin C.

    25. TF

      Mm-hmm.

    26. SC

      Even though it's really almost indistinguishable from a can of soda.

    27. TF

      [laughs]

    28. SC

      It's just they've convinced us that this is what responsible people do, they read the news.

    29. TF

      Mm-hmm.

    30. SC

      And it's really trash information. I'm usually extremely bad at trivia night, which surprises a lot of people, 'cause I read a lot of books, but the reality is that... my, my retort is that I just don't know trivial things.

  14. 51:57 – 57:52

    Why does new employee onboarding take a month at Levels?

    1. SC

      Yeah.

    2. TF

      Let's come back to onboarding for a second. Repeat back to me how you'll do this task, and then you can iterate on that as an example. What are some other practices or mistakes, either, that you've seen in onboarding or, or ways that you guys have refined your approach to onboarding? Because I'll speak for myself personally, I've become, I think, much better at hiring over time-

    3. SC

      Mm-hmm

    4. TF

      ... especially in the last few years. I still think almost certainly I'm very mediocre on onboarding, and there are a hell of a lot more books [laughs] on hiring-

    5. SC

      Yeah

    6. TF

      ... [laughs] than there are on onboarding. [laughs]

    7. SC

      Totally.

    8. TF

      And I've read a bunch of books on hiring. Very little said about onboarding generally.

    9. SC

      Yeah, I, I think the biggest thing is people, people really want to jump into it immediately.

    10. TF

      Mm-hmm.

    11. SC

      And so-

    12. TF

      Now by people, do you mean the people who have-

    13. SC

      People who, who join. Yeah

    14. TF

      ... who join.

    15. SC

      Mm-hmm.

    16. TF

      Right.

    17. SC

      They want to jump into it immediately. And we have an onboarding checklist in Notion. We, we have a template. We copy it for each new person that joins, and they have a set of tasks that they do each day. It's pretty well-guided. I can share the template with you if you're curious.

    18. TF

      That'd be amazing. I would love-

    19. SC

      Yeah

    20. TF

      ... I would love that.

    21. SC

      Yeah.

    22. TF

      Is this for all employees or EAs specifically?

    23. SC

      All employees.

    24. TF

      All employees.

    25. SC

      Yeah. Mm-hmm.

    26. TF

      Okay.

    27. SC

      And there is a video of me at the start of each week where I specific- it's, it's a Loom where I specifically say, "Hey, at this point, people usually want to skip onboarding and start jumping into their tasks. Don't do that. It's always a mistake." [laughs]

    28. TF

      [laughs]

    29. SC

      "Really take onboarding seriously." Our onboarding process is a full month, and we don't expect people to start producing for a month, and it, it really does take that long for a lot of people to get fully up to speed, and we help guide them in more slowly. Read these books, read this documentation that we have about how we built our culture on... E- especially for our case, 'cause the way that we operate is very different than a lot of people's previous experiences, and so it's pretty jarring when you see a lot of the transparency of... When your first one-on-one gets published to the rest of the company, it's pretty jarring.

    30. TF

      [laughs]

  15. 57:52 – 1:02:09

    What most delegators wish they’d known as newbs.

    1. SC

      from day one.

    2. TF

      So there is a, a tactical guide to working with EAs, how to make delegation your superpower. This, this piece that in your very beautiful, meticulously prepared notes, I gotta say, [laughs] like this is kind of my, my, my dream type of guest where you're like, wow, okay. This, this, this is, you have, if you were drafting, I would feel very confident if you were drafting my responses for-

    3. SC

      [laughs]

    4. TF

      ... LinkedIn. It's very, very well put together and [laughs] like the flow, everything is well thought through. In this particular guide, and this, this can also be more expansive than the guide, I'm wondering what other recommendations around delegation you have received positive feedback from where people try something and they're like, "Oh my God, I can't believe I didn't do this earlier," or, "I didn't think that was gonna work and it actually really worked." Anything that comes to mind?

    5. SC

      The biggest one is using Loom and just doing workflow recordings.

    6. TF

      Mm-hmm.

    7. SC

      So it's just the, when I've, I've worked with a lot of people to help them get better at delegating, and the thing that I really emphasize is figure out how to reduce your perceived risk of doing this thing.

    8. TF

      Hmm.

    9. SC

      Just lower the threshold for how much work you think you need to put into it.

    10. TF

      Into what? Into training someone or-

    11. SC

      Yeah.

    12. TF

      I see.

    13. SC

      Yeah, just lower your perceived risk. One of the reasons why people often fail to delegate as well, they make a lot of assumptions about how much effort's gonna go into it. They're like, "Oh man, well, I'm gonna have to like write a whole process doc, and then I have to like do..." It's just, just reduce your assumptions and just say, all right, what is the simplest thing you can do? Do all of the work that you were going to do anyway exactly the same as you were going to do it, and just turn on Loom and record it.

    14. TF

      Mm-hmm.

    15. SC

      And just try that. It's effectively zero effort, zero cost, and you can have a three-hour Loom and just share that with your EA and say, "Is there anything in here that you think you could do that would help me?"

    16. TF

      Hmm.

    17. SC

      And almost every person that's done this is amazed at how many things come out of just a simple workflow recording like that.

    18. TF

      Hmm.

    19. SC

      So just lower, figure out how to lower the perceived risk of it. And what's nice about, this is something that's different about remote versus in person, is that when you're remote, remote first is a concept that I think GitLab came up with, which is whether you're in person or not, you have the same principles as you would if you were remote. And if you're remote first, everything that you do is on a computer, and it is therefore necessarily content if you want it to be.

    20. TF

      Mm-hmm.

    21. SC

      And so typing at your keyboard could be content if you wanted it to. It's like a Twitch stream of your actual work, as opposed to something that you're doing in the, in the real world where you don't have that. If you're on a Zoom call with somebody, that could just be content. In a way that it wouldn't be if you were going on a walk.

    22. TF

      Mm-hmm.

    23. SC

      So really leaning into what's possible with this remote work style.

    24. TF

      Not just reading the stage play-

    25. SC

      Exactly

    26. TF

      ... into the radio mic.

    27. SC

      Yeah, exactly. If you really lean into what's possible with the everything is content model, the amount of leverage that you get is much, much higher, and it's... This is the, the shift, is that people are not super comfortable with that yet.

    28. TF

      Mm-hmm.

    29. SC

      Like, I've been working with Kozma, who runs product for us, and she's been just really getting used to, there's a lot of process stuff-

    30. TF

      Kozma?

  16. 1:02:09 – 1:05:32

    Loom security and privacy concerns.

    1. TF

      I imagine bringing on Nie, this is someone I don't know very well, and I would have... And I want you to disabuse me of this, or to at least to attempt. Be like, if I do a three-hour Loom, I'm gonna be getting into all sorts of sensitive stuff.

    2. SC

      Yep.

    3. TF

      And then maybe if I were to try to create another objection/type of resistance, it would be I'm just gonna be doing probably a bunch of random stuff. I mean, people who've read my books and so on might imagine, like, every day is just this, like, surgical Tron race where I'm just threading needles-

    4. SC

      [laughs]

    5. TF

      ... and it's just this, like, masterful Iron Chef display of performance. That's not what it looks like.

    6. SC

      Yeah.

    7. TF

      Right? Even on my best days, it's like, looks like I'm either staring watching paint dry or it's, it's a lot of juggling different things. So I would be like, ah, I don't... I'm not convinced this is going to be super helpful, and I might have concerns around privacy or security, or whatever it might be.

    8. SC

      Yeah.

    9. TF

      Uh, I can't be alone. What are your thoughts on that? I mean, I think m- maybe out of the box, you ha- you are probably much more embracing of, like, full transparency and public sharing than I am.

    10. SC

      Yeah.

    11. TF

      But I would imagine there are some people who come from maybe a different company or a different experience who would have maybe similar thoughts, I'm not sure. But like-

    12. SC

      Yeah

    13. TF

      ... what would you say as my podcast guest/involuntary therapist? [laughs]

    14. SC

      [laughs] I, I think a big part of the answer is that the worst case scenario is you turn on a three-hour Loom-

    15. TF

      Mm-hmm

    16. SC

      ... and then you delete it.

    17. TF

      Right.

    18. SC

      Like, that is-

    19. TF

      It's, it's not a live stream.

    20. SC

      No, it's not a live stream.

    21. TF

      Yeah.

    22. SC

      And that's, that's the thing that people really struggle with-

    23. TF

      Mm-hmm

    24. SC

      ... is like the first assumption is if it's recorded, it's going on the front page of The New York Times tomorrow.

    25. TF

      [laughs]

    26. SC

      And then at some point, you just realize that it's not.

    27. TF

      Yeah, it's so stupid, right?

    28. SC

      Yeah.

    29. TF

      It's just like, now that you say it-

    30. SC

      [laughs]

  17. 1:05:32 – 1:10:53

    From to-do list to calendar.

    1. TF

      So we're going to weave back to Calendly, because we were, we were kind of joking/seriously discussing how a lot of people get offended with this tool, but that is the micro level. I don't want to, I don't want to go immediately to tools, although people might think that's where we're going next. To-do list to calendar.

    2. SC

      Yeah.

    3. TF

      Could you explain this transition, or what that means to go from to-do list to calendar for you?

    4. SC

      This is probably the single most important tactic in time management for me personally. I, I tend to be overly optimistic about how much I can achieve.

    5. TF

      Okay, can I pause for one second?

    6. SC

      [laughs]

    7. TF

      So my ex-girlfriends have always found this hilarious, 'cause I'll be like, "Okay, it's Friday, it's 2:00 PM, we have a dinner at 6:00. Over the next four hours, I'm just gonna do A, B, C, D, E, F, and G." And my ex-girlfriends who I've been with for any period of time will look at me and they'll say, "You're never gonna get all that done."

    8. SC

      [laughs] Yeah.

    9. TF

      "I've seen this before. There's no way you're gonna get even half of that done."

    10. SC

      Yeah.

    11. TF

      So yes, please continue.

    12. SC

      Yeah, totally. And it's, I've worked with a lot of people on our team, people who are friends of mine through this, and the, the thing that almost always happens is they have this long to-do list And I say, "All right. Here's what I want you to do. Take everything on this to-do list with the dates that you think they'll get done by, which is usually this week or next week, and I want you to just put them on your calendar with the amount of time you think it's gonna take, and then we'll have another follow-up call next week and we'll see what happens." And then we have the call and then they say, "This process doesn't work." I say, "Why is that?" They say, "Well, I tried to move it over there, but there isn't enough space in my week-

    13. TF

      [laughs]

    14. SC

      ... to fit all these items." It's like, yes, that's- [laughs]

    15. TF

      That's the point of the exercise

    16. SC

      ... this is the point of the exercise, is there literally is not enough time. Your time is finite, and the number of digital items you can add to a to-do list is infinite. You're- you are working with the wrong constraint, which is like the amount of items you can fit in a database row-

    17. TF

      Mm-hmm

    18. SC

      ... as opposed to the number of things that you can fit in your finite time of your calendar. And so we then work on, all right, you probably need slack during the course of the day, usually like 50% is a good target, because things come up-

    19. TF

      Oh, I see, not the tool Slack, but-

    20. SC

      Yeah

    21. TF

      ... but-

    22. SC

      Space, extra space.

    23. TF

      Mm-hmm.

    24. SC

      Mm-hmm. You need extra space in the day. And so we work on things like, for me, I process a lot of email.

    25. TF

      Mm-hmm.

    26. SC

      I probably do-

    27. TF

      And when you say you need space in the day, could you just briefly say more about that? Uh, because the way I'm hearing that is that you have 50% of your time open.

    28. SC

      Open.

    29. TF

      But I'm not sure if... Now, is that, for instance, like tomorrow you would have 50% of your time open, or does that mean that in advance of scheduling other things, like three weeks from now, each day is 50% open?

    30. SC

      It's generally 50% open just fully.

  18. 1:10:53 – 1:14:31

    How Sam skips the to-do list entirely.

    1. SC

      do it next week.

    2. TF

      From a process perspective then, do you start with, I'm imagining not at this point, but just, just so I get a-

    3. SC

      Yeah

    4. TF

      ... really clear understanding. Let's just say you're looking at next week. You have these recurring blocks-

    5. SC

      Mm-hmm

    6. TF

      ... of email. That's already in there.

    7. SC

      Yeah.

    8. TF

      You may have other repeating blocks, and I would be curious to know what they are, so let's bookmark that. When you're looking at, say, the to-dos that will be converted into calendar or not for the next week, what does that process look like? Do you start with maybe a c- a, a to-do list and then that goes to your EA and she tries to slot, he or she tries to slot them in for the anticipated amount of time? Like, what, what does that look like from kind of start to finish?

    9. SC

      The answer is you just skip the to-do list step entirely.

    10. TF

      Mm-hmm.

    11. SC

      So when I get a new task, a lot of my tasks effectively come in through email.

    12. TF

      Right.

    13. SC

      So I'll get an email, and this is also another thing that I, I worked with a couple people on who really, really struggled with email, and the thing they struggle with is using their email as a to-do list, which is a very common thing that people do. The problem, it creates a lot of anxiety when you have this stack of uncategorized things. It could be 15 minutes, it could be 50 hours.

    14. TF

      Mm-hmm.

    15. SC

      You have no idea until you open up each one individually to figure out how much work it is. And so the same process of translating your to-do list into your calendar, you can do the same thing with email, which is, I worked with somebody recently where I said, "All right. Let's open each email. How long is this gonna take you to respond to?" These are like the chunkier ones. It's like 30 minutes. Great. Mark it as done, copy the link, and put that link in your calendar, so you're gonna spend this 30-minute block responding to this email.

    16. TF

      Mm-hmm.

    17. SC

      What's the next one? That's gonna take me a full hour, 'cause I have to write something for them.

    18. TF

      That's interesting. So the clearing of the inbox then is really in some capacity scheduling-

    19. SC

      Yeah

    20. TF

      ... the proper amount of time to reply to these things, so you're not looking at this- Undifferentiated stack of shit-

    21. SC

      Exactly

    22. TF

      ... that you are opening multiple times, marking as unread-

    23. SC

      Yeah [laughs]

    24. TF

      ... going back to it, forgetting what you read, reading it the 17th time, or whatever that might be.

    25. SC

      Yeah. It's a stress thing. Like, it, it is very stressful to have this list of things. It's just an ambiguous amount of effort. It is stress-relieving to see, all right, I will do that on Thursday of next week.

    26. TF

      Mm-hmm.

    27. SC

      And I have nothing, I have nothing pending right now. I have not dropped any balls-

    28. TF

      Mm-hmm

    29. SC

      ... because I know that anything that is time-sensitive that needed to be done today is already done, and there's nothing, there's no ambiguous deadlines looming that I'm not aware of, because they're in my calendar. And if you change it, this is where closing the loop is a helpful factor, which is if you say, "I'm gonna block this off for Thursday," you can tell that person, "Hey, I'll get back to you on Thursday."

    30. TF

      Mm-hmm.

  19. 1:14:31 – 1:16:12

    General schedule and repeating items.

    1. SC

      the to-do list.

    2. TF

      Mm-hmm. What do you have in your calendar as repeating items? And we don't have, we don't have to go through all of them necessarily, but I'm curious. This could not only be professional company obligations, but say personal items that you block out, right? Exercise, any number of things. So you have email processing. You have, I imagine, the Friday Forum.

    3. SC

      Yep.

    4. TF

      What are some of the other repeating elements that you can block out weeks in advance?

    5. SC

      Mondays are my meeting days, so I tend to stack all of my meetings on Mondays. It's, it's common for me to have, like, 14 hours of meetings on Mondays. I just get them all done with so I don't have anything else during the week. Fridays I often have meetings as well, but they tend not to be the recurring ones, other than maybe the Friday Forum or some, maybe the book club, which I think we do monthly on Fridays.

    6. TF

      Mm-hmm.

    7. SC

      So Mondays are a lot of my recurring team meetings. Tuesday, Wednesday, Thursday are almost always just open.

    8. TF

      Mm-hmm.

    9. SC

      I tend to leave Wednesdays as, like, a sacrificial anode of, like-

    10. TF

      [laughs] What does that mean?

    11. SC

      As in, like, when-

    12. TF

      [laughs]

    13. SC

      ... when somebody says to me, "Hey, I was trying to book time on your calendar, but you're, you're booked for the next two months"-

    14. TF

      Mm-hmm

    15. SC

      ... then I start sacrificing some of my Wednesdays to allow for meetings to be scheduled.

    16. TF

      Mm-hmm.

    17. SC

      The term comes from how stainless steel works, where it's covered in something that... I think it's zinc in that case, and how it works is the zinc starts to get deteriorated before the steel does.

    18. TF

      Mm-hmm.

    19. SC

      So it's, you're sacrificing a different material in order to keep the steel working well.

    20. TF

      [laughs]

  20. 1:16:12 – 1:20:12

    Scheduling stress reduction.

    1. TF

      Okay. Got it. Any personal stuff that comes to mind, like self, self-care stuff, or is that sort of on automatic in some other way, or taking a backseat? [laughs]

    2. SC

      Yeah. I've, you know, I've tried doing meditation.

    3. TF

      Mm-hmm.

    4. SC

      I, I did the Sam Harris-

    5. TF

      Waking Up app

    6. SC

      ... Waking Up one. I don't think I'm particularly... I didn't notice any benefit.

    7. TF

      Uh-huh.

    8. SC

      I, I did it for, I think, a month.

    9. TF

      Mm-hmm.

    10. SC

      I think I'm, just my, my stress levels by default are pretty low.

    11. TF

      Mm-hmm.

    12. SC

      So it could be something-

    13. TF

      Has that always been the case, or is, how much of that is by the way you've constructed your life versus innate temperament? Do you have any idea?

    14. SC

      I think it is, some of it's innate temperament, but a lot of it is how I've structured my life, for sure.

    15. TF

      What are other things you have done to reduce the ambient chronic levels of stress/metaphorical-

    16. SC

      Yeah

    17. TF

      ... metaphoric, metaphorical, I should know [laughs] which it is by now, inflammation?

    18. SC

      Yeah.

    19. TF

      You were us- using that on the organizational level. Like, what are some of the other crux moves or decisions or fill in the blank that have helped with what you're describing?

    20. SC

      One of the biggest ones is news sobriety.

    21. TF

      Mm-hmm.

    22. SC

      And I think that encapsulates a lot more. One of my personal philosophies is that I do not allow others to impose upon my attention. And so if I am getting information, I would like to seek it out, and I don't want other people to take my time against my will-

    23. TF

      Mm-hmm

    24. SC

      ... or tell me what I should be thinking or focused on-

    25. TF

      Mm-hmm

    26. SC

      ... whether I want to or not. That's been a big challenge. I, I think almost everyone underestimates how, how impactful even seemingly trivial information is, of, like, seeing a plane crash-

    27. TF

      Mm-hmm

    28. SC

      ... on the news will make you fear planes subconsciously. It is a, it is an availability bias problem. You can know the statistics and you can say that it's safer, but in your mind, if you see it happen or you see something on the news, you assume that it is representative of the world, and it's, it's really hard to beat. There's a really good book, Factfulness. I don't know if you've heard of it.

    29. TF

      Mm. I have heard of it. I haven't read it.

    30. SC

      Yeah, it's a really good book which really just goes over there are so many things that are getting better, and yet almost everyone thinks that those things are getting worse.

  21. 1:20:12 – 1:36:04

    Selecting books and hosting themed salon dinners.

    1. SC

      long walks.

    2. TF

      How do you choose your books?

    3. SC

      A lot of them are through recommendations. I host these salon dinners maybe roughly once a month, and one of the questions that I always ask people is, the, the intros are always your name and the last book you read. And so that's sort of my hack for getting good book recommendations.

    4. TF

      Mm-hmm.

    5. SC

      And I just, I add them to my wishlist on Audible, and then one of my new rules over the last couple years is I will only purchase a book if it is the next book that I'm going to read.

    6. TF

      Mm-hmm.

    7. SC

      Because I found that-

    8. TF

      [laughs] I, I am so... [laughs] I'm a chronic violator-

    9. SC

      Yeah

    10. TF

      ... of this. Oh, my gosh.

    11. SC

      I, I just found that stacks of books that I have committed to reading that I have not read felt like a betrayal of my own commitment to myself.

    12. TF

      You know, there's a Japanese word for this.

    13. SC

      No.

    14. TF

      The stacks of books and this, like, guilt and obligation that it elicits. Tsundoku.

    15. SC

      Oh, yeah. [laughs]

    16. TF

      Tsundoku [laughs] is-

    17. SC

      Yeah

    18. TF

      ... the word for that. It's a thing.

    19. SC

      Yeah.

    20. TF

      Yeah.

    21. SC

      For sure. And I just realized I'm just gonna put them on my wishlist, and then when I feel like reading a book-

    22. TF

      Mm-hmm

    23. SC

      ... when I finish whatever book I'm reading now, I, I go to it and I scroll through it. What am I feeling like right now?

    24. TF

      Mm-hmm.

    25. SC

      You know what? A biography feels really good. I'm gonna download that. So my wishlist is probably 2, 300 books.

    26. TF

      [laughs] Oh, shit.

    27. SC

      So I have a pretty deep backlog.

    28. TF

      [laughs] All right. So you... All right. I wanna stick with the... We're, we are gonna come back to the salons because-

    29. SC

      Yeah

    30. TF

      ... this underscores something for me that has proven very important also. But before we get to that, so you have a backlog of 300 books. How do you choose the next book?

  22. 1:36:04 – 1:37:50

    Calendly and related social hurdles.

    1. SC

      it.

    2. TF

      Calendly. So since you are using your calendar as your fine-tuned to-do list, let's just say, that means your availability would seem to be much more predictable. What is Calendly? How do you use it? And how do you overcome some of the social hurdles that might be associated with it?

    3. SC

      Calendly is a, it's an incredible time-saving tool, where you set times that you're available. It syncs with Google Calendar. And so when I have time blocked off to do things, it doesn't show up as an availability, and you set what hours you're available. And so people can just pick time on your calendar. This is, this is why I think when I get a calendar link from somebody, I'm, I'm touched because they are allowing me to impose upon their attention. They're saying, "I'm giving you access to my time, whenever is convenient for you." And that's a, that's a tall order to, like, get that from somebody. For some reason, there are people who are deeply offended by it, and I really just, I, I really do not understand it

    4. TF

      It's not a small percentage, though.

    5. SC

      It's not.

    6. TF

      Like it's, it's a decently high percentage.

    7. SC

      Yeah.

    8. TF

      So have you, have you found any way, just like the sent on Sam's behalf at the bottom-

    9. SC

      Yeah

    10. TF

      ... right, makes... I think that's a contributing ingredient that helps that to work.

    11. SC

      Yeah.

    12. TF

      Are there any ways that you've been able to preemptively smooth potentially ruffled feathers with Calendly, or not really?

    13. SC

      I think the, the solution is just to slowly filter those people out of your life.

    14. TF

      [laughs]

    15. SC

      I think that's kind of the answer. Like, if, if that is the, if that's the hill you wanna die on-

    16. TF

      [laughs]

    17. SC

      ... then like we'll be on different hills. It's okay.

    18. TF

      [laughs] Right. Okay. Makes sense.

  23. 1:37:50 – 1:40:42

    Using email proactively.

    1. TF

      So we are, I keep teasing this, it's like after the next round of commercials, but we are gonna come back to the, what you do with four EAs, but these are all interrelated. Briefly, a question on sort of higher level principles related to inbox, and then just the tactical question of how do you actually go through your inbox?

    2. SC

      Yeah.

    3. TF

      So the first is you talking about, and I'm putting words in your mouth, but trying to, to recap here, see if I get it right. Basically doing a version of repeating the task back to you, which [laughs] is reducing the ability of unwanted or unhelpful or unactionable information to impinge on your life so you can be proactive.

    4. SC

      Yeah.

    5. TF

      However, you spend a lot of time in email, and for a lot of people, that is the arena that you enter that is full of everyone else's agenda for your time.

    6. SC

      Sure.

    7. TF

      So you can become very reactive. So I'm wondering how you think about using email proactively and not becoming overly reactive, getting pulled away from your priorities if you've set them.

    8. SC

      Yeah.

    9. TF

      And then I suppose the, the follow on question is just how you process email.

    10. SC

      I'm an inbox zero person. I try to hit inbox zero at least once a week, which is the, the practice of marking all emails that you've processed as done. So you get to the end of the week and you have processed all of your emails. It is definitely one of the holes in the strategy where I get lots of uninvited inbound information. I do have a process by which my EAs clear my inbox. I have a separate category called not important, where they go through and they just move all the things they don't think I need to see into that.

    11. TF

      Mm-hmm.

    12. SC

      And I check it every once in a while, and in the early days, every so often they would flag something as not important that I actually should have seen. But at this point, it's like a 100% success ratio of them seeing my patterns. And typically what I do is I turn on a Loom as I'm going through the not important and I say, "Yep, these all make sense. Oh, this one should probably keep in because of this reason. This one we should pull in because of this reason." And then I just share that to them as feedback.

    13. TF

      Mm-hmm.

    14. SC

      And then the process just gets better. It's probably the biggest hole of people imposing upon my attention, and it's something that I'm trying to work on a solution to. I know there have been interesting companies that have tried different things, like you have to pay money to send somebody an email. I don't know if those ever took off, but that's an interesting strategy.

    15. TF

      Mm-hmm.

    16. SC

      It's like just adding some friction.

    17. TF

      [laughs]

    18. SC

      It's like, yeah, if you pay me $100, you can send me an email.

    19. TF

      Yeah.

    20. SC

      That's okay. And I will read it.

    21. TF

      Yeah.

    22. SC

      I will definitely read it if you pay me $100 to get an email.

    23. TF

      [laughs]

    24. SC

      Sure.

  24. 1:40:42 – 1:44:08

    The underrated power of hotkeys and shortcuts.

    1. SC

      So the nature of processing email, I think the way to do it most efficiently, I use Superhuman as a tool. Hotkeys are probably the, the lowest hanging fruit for people to improve their productivity-

    2. TF

      Mm-hmm

    3. SC

      ... for almost no cost.

    4. TF

      How do hotkeys differ from keyboard shortcuts in Gmail?

    5. SC

      It's the same idea.

    6. TF

      Okay.

    7. SC

      The thing is, most people just don't take the time to learn it. There's several studies on this that I, I can, I can share with you, but it is, it's like free productivity. You spend a handful of minutes, 15 minutes, maybe 10 minutes one time learning what hotkeys to use.

    8. TF

      Mm-hmm.

    9. SC

      And most people will see a 10 to 40% increase in productivity immediately for the rest of their lives.

    10. TF

      Mm-hmm.

    11. SC

      And yet most people don't take the time to learn them. Like it is, if you are not using hotkeys to process your email, to do... If you're in Figma, learn the hotkeys. If you're in Photoshop, learn the hotkeys. It is, is a free productivity boost for almost no cost.

    12. TF

      And in the case of email, and you have reply, reply all-

    13. SC

      Yeah

    14. TF

      ... archive, what are some other functions that you would access with hotkeys?

    15. SC

      So, you know, mark as done. I think one of the biggest ones is snippets-

    16. TF

      Mm-hmm

    17. SC

      ... where you have pre-drafted messages. And this is something that it's really easy to see when... A good example, my co-founder, Casey, when she was struggling with email, I asked her to just record yourself doing email for however long it takes, and then I'll watch it and give you feedback.

    18. TF

      Hmm.

    19. SC

      And this is the workflow thing, where she just recorded it, she shared it with me, and there were many points where I would say, "Hey, during this point, have you noticed this is the fourth time you've sent this exact same email?"

    20. TF

      Hmm.

    21. SC

      "And you type it out every time? You should just create a snippet-

    22. TF

      Mm-hmm

    23. SC

      ... and you should just send it to them. You see this part here where you wrote a very long response? He was actually really just asking you for a yes or no. You didn't have to provide much longer context. You could have said, 'Yeah, that sounds good. If you need any more context, let me know.'"

    24. TF

      Mm-hmm.

    25. SC

      And that could've been it. You didn't need to spend 15 minutes on that. You could have just said, "Yes, and if you need more, let me know and I can give you more." So don't make the assumption that you have to spend 15 minutes on it if you usually don't have to. And so just having that feedback loop is really helpful, and this keeps tying back to Loom as a useful tool for this.

    26. TF

      Mm-hmm.

    27. SC

      But, like, being able to just see it- In a previous era, you would have just had a coach standing over your shoulder watching, and now you can do this asynchronously. I can watch it at two and a half X. I can skip over parts that are not relevant. So it's just a, it's a really big enablement tool.

    28. TF

      And for the sake of clarity, to confirm-

    29. SC

      Yeah

    30. TF

      ... inbox zero does not mean that you have handled all of the tasks or content associated with those emails. It simply means that you have either responded to them-

  25. 1:44:08 – 1:48:00

    Scheduling spontaneity.

    1. TF

      All right, so the question of the hour: What on earth do you use four assistants for?

    2. SC

      [laughs] I use it for a lot of things. I actually, I have a public Notion database of all of these tasks.

    3. TF

      Mm-hmm.

    4. SC

      I filtered for the ones that contain confidential information.

    5. TF

      Mm-hmm.

    6. SC

      But there's, I don't know, 40, 50 of them that are kind of examples.

    7. TF

      Great, and so we'll put those in the show notes as well.

    8. SC

      Yeah. So some simple things are, before every call, I send, two days before the call, I send links that provide more context for who I am, what the company does, whatever the thing is. And so two days before, they get that information. They also do follow-ups. So I, I have a Notion page called Sam's Calls where before I jump on this call, I have all of my call notes stacked, and I have contacts on each one of them. So I, I open up my calendar, I go to the call, and then I open my notes, and it's, "Your call with this person. Here's a screenshot of the email that you had with them setting up this meeting."

    9. TF

      Got it. Your EAs are creating all of this.

    10. SC

      My EAs are creating all of this behind the scenes.

    11. TF

      Mm-hmm.

    12. SC

      I used to do it myself, but over time I just trained the EAs to do it so I don't have to do it, and it really just gives me a ton of leverage. So things like almost nobody I know pays attention to their LinkedIn messages anymore.

    13. TF

      Mm-hmm.

    14. SC

      It's just a cesspool.

    15. TF

      Mm-hmm.

    16. SC

      But if you have an EA that you've trained to like, "Hey, filter out any random requests from dev shops in India.

    17. TF

      Mm-hmm.

    18. SC

      Just, just archive those immediately. And if there's anything from these sorts of people, just send me a note and say, 'Hey, I think you should respond like this.'" This is the semi-automation part. Same with Twitter DMs. I don't manage those. I, I get a screenshot whenever somebody that they think meets the criteria that they think I should be talking to, and that's all managed by them. And so those are just a handful of examples of like the, the ways in which I can get leverage on my time.

    19. TF

      Mm-hmm.

    20. SC

      Things that I used to maybe do myself, but at this point I have so many of these tasks. Like another one that I have my EAs do consistently is I'm really diligent about tracking my time. It's one of those interesting things where, this is similar to Calendly, I get people who just aggressively negatively respond to the idea that you pay attention to where your time is going. I don't-

    21. TF

      Really?

    22. SC

      Oh, yeah.

    23. TF

      See, that's one that I wouldn't-

    24. SC

      Yeah

    25. TF

      ... have expected.

    26. SC

      They're like, "Do you really need to optimize every 15 minutes of every day?" And like, "Don't you have time for spontaneity?" These are the common things that I hear.

    27. TF

      Mm.

    28. SC

      The answer is like, "Yeah, of course. I, I have lots of time for spontaneity. I, I schedule it." It's like- [laughs]

    29. TF

      [laughs]

    30. SC

      ... this is a week I'm not planning anything. Anything could happen, but I'm doing it on purpose, not by accident.

  26. 1:48:00 – 1:49:40

    Calendar course correction.

    1. TF

      So how do you course correct? What does that look like? Are there certain tasks or types of work or interactions that you just categorically do not engage with now? Are there kind of no categories for you?

    2. SC

      It's more that having the awareness. I, I was talking to somebody recently about this where we did a, a values exercise, and they came up with a set of values that they have. And then it's a bit of a trick question because then you say, "All right. Let's go over your calendar and how you spent your time." And they'll say, "Oh, my values are friends, family, this, that." And it's like, "Oh, how'd you spend your time?" It's like YouTube, Instagram. It's like, do you notice how none of these things match? Like your, your actual priorities are consuming news. Your actual priority is doing sports, which is fine. There's nothing wrong with that. But empirically, your priorities are this. How you spend your time are your priorities. And that's a difficult thing for people to understand, but it really is like an epistemological problem where like the, the example would be if you're an ax murderer- But you go your whole life and you never murder someone with an ax, are you actually an ax murderer?

    3. TF

      [laughs]

    4. SC

      Like, the act is what makes you what you are.

    5. TF

      Yeah.

    6. SC

      I think this is Ben Horowitz's book, like, what you do is, is who you are.

    7. TF

      Mm-hmm.

    8. SC

      Like, that's, that is what it is. How you spend your time-

    9. TF

      Yeah

    10. SC

      ... it doesn't matter.

    11. TF

      I mean, your, your calendar is your priorities.

    12. SC

      Yeah. It is the empirical record of your actual priorities.

    13. TF

      Mm-hmm.

    14. SC

      And almost everybody that I talk to, those two are not

  27. 1:49:40 – 1:51:37

    How Sam utilizes multiple EAs.

    1. SC

      matching.

    2. TF

      Mm-hmm. Okay. So for those people listening, they might think, well, four assistants, not to beat a dead horse, but I think it's maybe a semi-dead horse-

    3. SC

      [laughs]

    4. TF

      ... that's worth beating a little bit more. They might think, why four? I mean, uh, I imagine that one would be more than enough. What about, and this comes back to an earlier concern of maybe novice, intermediate delegators. I consider myself a pretty experienced delegator, and I still think about this, and it causes-

    5. SC

      Yeah

    6. TF

      ... me some hesitancy. Underutilization. Could you give a few more examples of tasks and why it makes sense for you to have multiple people?

    7. SC

      Almost all of the tasks that I have them do are recurring ankle-biter tasks that would take me five minutes here and there.

    8. TF

      Mm.

    9. SC

      And the reality is they just accumulate. So part of it is that almost certainly I will be able to do it faster and more effectively, but this is a comparative advantage thing, is if it takes me 10 minutes and it takes them 30 minutes, that's fine.

    10. TF

      Mm-hmm.

    11. SC

      Because I have other things that I could be doing with my time that are higher value than these tasks. And so if I could be spending 30 hours a week on these tasks, it might take them 90 hours a week, or 100 hours a week of effort to be able to do these tasks, but then I don't have to do them anymore, and then I can do other things.

    12. TF

      Mm-hmm.

    13. SC

      I certainly didn't start with four, I started with one, and she's been great. And interesting thing about this is where really leaning into remote is she's in the Philippines. We don't overlap very much in terms of time zone. I have still not communicated synchronously with her. All of our communication has been async in-

    14. TF

      Mm

    15. SC

      ... Looms or in content or in some form of async manner-

    16. TF

      Mm-hmm

    17. SC

      ... so that you can reference all of your previous conversations. I don't have any specific reason not to talk to her, it's just-

    18. TF

      Mm-hmm

    19. SC

      ... we haven't needed to do that.

    20. TF

      That's incredible.

  28. 1:51:37 – 1:58:58

    Improvement growth for intermediate delegators.

    1. TF

      All right, so we'll make that list of tasks available. Uh, where are the most common areas for improvement, growth opportunities [laughs] for people who are blue belt delegators, right? So these are people who've been, maybe they've been working with an EA for six months, a year. If they were to send you, you were just magically able to ingest with a port on the back of the head like The Matrix, a thousand Loom interactions they've had, workflows, et cetera, much like you looked at your co-founder's email flow, what do you think the most common types of advice would be, or issues would be that you would spot?

    2. SC

      I would say for, for somebody who's a blue belt, which I don't know my belts, I assume that's-

    3. TF

      Blue belt's like-

    4. SC

      ... medium belt. [laughs]

    5. TF

      It depends on, it depends on the, the system we're talking about, but yeah, what I mean to say is intermediate.

    6. SC

      Yeah. If somebody is intermediate, I would say that one would be creating a system of feedback loops. So something that... 'Cause one of the things that fails here, and this was a conversation I recently had with somebody on our team who said that he just doesn't feel like he's getting leverage out of his EA, which is surprising because I see how much leverage he gets. And having a system where you keep track of all of the ongoing tasks, and I said, "Okay, cool. Well, if you don't need one, that's, that's not a big deal. Obviously it costs us less money. But before we do that, let's go into the database and let's see all the tasks that this person is doing for you, and let's decide which of these we don't need." And he was ha- he had something like 30 ongoing tasks. I said, "How about this one?" He's like, "No, no, I definitely still need that." "How about this one?" "Yeah, that's, probably should keep that one." And, like, we went through almost all of them. We, I think we eliminated two of them. It's like, okay, well, it sounds like you're getting a lot of leverage [laughs] out of your, out of your EA.

    7. TF

      Let me ask a strange question. Why would he be interested in having his EA do less? Did he feel like he was spending more time on managing them than the work product that was being produced? Like, what is his incentive? How does he benefit from having this conversation?

    8. SC

      Yeah. He is somebody who has the company's best interest in mind.

    9. TF

      I see.

    10. SC

      And he just doesn't feel like we're getting X dollars in value from-

    11. TF

      I see what you're saying

    12. SC

      ... this person's tasks.

    13. TF

      Mm-hmm.

    14. SC

      And then we looked at each of the tasks, and we looked at how much time each task takes.

    15. TF

      Mm-hmm.

    16. SC

      And the thing is, they're happening behind the scenes, and so he didn't have a lot of visibility into it. And so this is one of the reasons why we actually, internally, why we do the Friday Forum-

    17. TF

      Mm-hmm

    18. SC

      ... is celebrating wins and having artifacts to represent progress is actually really important.

    19. TF

      And by artifact, you just mean some type of captured media generally?

    20. SC

      Yeah.

    21. TF

      Mm-hmm.

    22. SC

      It can be anything. It can be an image, something that shows progress over time. People need to feel that things are working and that things are good. If they don't, you just leave this, this void where people... The example of, of the person who felt like he wasn't getting leverage from his EA, he just hadn't looked at all the things that they were doing. Like, they were all there. He could have found them, but they were all happening behind the scenes, and he forgot that the automation was even happening.

    23. TF

      Mm-hmm.

    24. SC

      And so just having that visibility and saying, okay. Like, we, we ended that conversation going, "You actually might need another one, because you're already almost at the limit of this person's capacity, and we only eliminated two out of something like 40 tasks."

    25. TF

      [laughs]

    26. SC

      Another one that I would say for people who are blue belt level delegators is, is really doing more in parallel tasking, which is anything that you are gonna do anyway, just have your EA or chief of staff do it as well. But don't put them in the mission critical path. This is one of the failure modes that a lot of people have.

    27. TF

      Could you give a concrete example of what that might look like?

    28. SC

      Yeah, so let's say you have something that needs to be delivered on Friday, and you were gonna do it, but instead you hand it off to your chief of staff. Don't rely on what their output is [laughs] to get that delivered on Friday. If you were gonna do it yourself, just do it yourself anyway.

    29. TF

      What type of task might that be? I'm just trying to imagine.

    30. SC

      Yeah.

  29. 1:58:58 – 2:04:33

    The Working with Sam user manual.

    1. TF

      I should try it. My next question is related to a bullet for an interview, a prior interview you did, which... Or actually, no, it was not an interview. It was a podcast, Founder Dynamics podcast.

    2. SC

      Mm.

    3. TF

      And the, I suppose, synopsis for the purposes of our conversation is that this is an episode that gives a feel for what it's like working with you and how other people perceive you. And I recently interviewed Dustin Moskovitz-

    4. SC

      Mm-hmm

    5. TF

      ... co-founder of Facebook, co-founder of Asana, current CEO of Asana. And in prep for our conversation, they also did a, an immaculate job of prep notes, and they sent a number of different things. One of them I had not seen before, and I've had some interaction with Dustin over the years, was a, in effect, I can't remember the title, but it's Working with Dustin-

    6. SC

      Mm-hmm

    7. TF

      ... as a document. It's a basically a user guide to Dustin, and it lays out all sorts of things, his temperament, his preferences, the things he hates, his Enneagram type. And I found it very compelling to the extent that I'm probably gonna create something like that, 'cause it could also be useful for external parties, contractors, agencies, who knows. Do you have something like that?

    8. SC

      Yeah, totally.

    9. TF

      Or what form does it take?

    10. SC

      Exact same format. We, we both took it from the same person. I don't remember... I think he referenced it in the podcast.

    11. TF

      Mm-hmm.

    12. SC

      But there's a specific person who popularized this.

    13. TF

      Mm-hmm.

    14. SC

      And we largely use the same format. It's also part of our onboarding. One of the deliverables at the end of month one is each new hire writes their own user guide.

    15. TF

      Mm.

    16. SC

      And it's been super helpful.

    17. TF

      Okay. So in that case, could you just for people who have not listened to the Dustin-

    18. SC

      Yeah

    19. TF

      ... episode or seen the document, what are some of the key ingredients in that user manual? And I wish I could give proper attribution to the person upstream.

    20. SC

      Yeah.

    21. TF

      I can't, I can't recall the name.

    22. SC

      Yeah, yeah.

    23. TF

      But we can put it in the show notes for folks.

    24. SC

      For sure. One of the categories is just background. We do a little bit more work than is typical. We actually hire a writer to do a, what we call a spotlight, where they, they interview this person and give, like, a whole rundown of interesting things about them until you read a little bit more about them.

    25. TF

      Mm-hmm.

    26. SC

      You learn what their hobbies are, where they grew up, all kinds of stuff. The more tactical things are like communication patterns. For example, for me, I really, really do not like being interrupted.

    27. TF

      Mm-hmm.

    28. SC

      And so my phone is, is by default-

    29. TF

      [laughs] S- sorry about the last two hours [laughs]

    30. SC

      No, no, I mean, I mean like during the day.

  30. 2:04:33 – 2:12:32

    Memo culture over meeting culture.

    1. TF

      Oh, yeah. Big time. It's like the scaffolding's really important.

    2. SC

      Yeah [laughs]

    3. TF

      Scaffolding is incredibly, incredibly important. Let's, we can always come back to anything that comes to mind related to that.

    4. SC

      Yeah.

    5. TF

      But memo culture over meeting culture.

    6. SC

      Mm-hmm.

    7. TF

      What is the role of memos and why are they important?

    8. SC

      I think some of this is philosophical.

    9. TF

      Mm-hmm.

    10. SC

      Which is, people can debate this, but I do believe sincerely that writing is thought.

    11. TF

      Yeah, I agree with that.

    12. SC

      Yeah. If you cannot write out your ideas, you do not have coherent thoughts. And a lot of people can convince themselves in a meeting where they're talking to people like, "Oh, yeah, I made a really good point there," or like, "We came to a good conclusion."

    13. TF

      Go back and read the transcript.

    14. SC

      Yeah, exactly.

    15. TF

      [laughs]

    16. SC

      And I, I did an experiment with this where I tried to figure out, you know, there's a, there's an emotional hurdle to blocking off, in my case, usually a full day to just like, all right, I need to write a memo on company strategy. Today's the day.

    17. TF

      Mm-hmm.

    18. SC

      Man, it's just so much effort to do that. What if I just had a call with somebody and I just spitballed all my ideas? And I tried it. I did this with my co-founder, and we just like bounced back ideas for a couple hours, and then we pulled the transcript and we pulled the useful bits, and we had like two paragraphs of useful information-

    19. TF

      [laughs]

    20. SC

      ... from a couple hours of conversation. Like, man, that was not helpful [laughs]

    21. TF

      [laughs]

    22. SC

      It's just writing is thought.

    23. TF

      Mm-hmm.

    24. SC

      And so I think where it comes down to is having a really thoughtful memo, it's an artifact that you can reference in the future. It gives you these data points of what were we thinking at each point in time.

    25. TF

      Why are they important? I understand the, maybe the function, right?

    26. SC

      Mm-hmm.

    27. TF

      But if we zoom out, what is the impact that these memos are designed to achieve?

    28. SC

      We have a memo on, on memos.

    29. TF

      Memo about memos [laughs]

    30. SC

      Yeah. It's, it's about long form memos.

  31. 2:12:32 – 2:14:53

    Fighting organizational entropy.

    1. TF

      Are there any particular memos that have had a disproportionate impact, putting aside the memo related to the large investment that would be-

    2. SC

      Mm-hmm

    3. TF

      ... occupying dozens of people for several years-

    4. SC

      Yeah

    5. TF

      ... which I recognize we've already covered as important. Are there any shorter memos that you think have had a wide-ranging or long-lasting impact that you're particularly proud of? Not necessarily-

    6. SC

      Yeah

    7. TF

      ... that you wrote. They could be.

    8. SC

      Yeah, there's quite a few of them. I think one of them is a, an article we wrote on organizational entropy, just broadly on strategies for fighting it, and I think that was really helpful for a lot of our managers to just recognize... I was talking to somebody on our team who... This is a bad habit a lot of engineers find themselves in as well, where you, you get really deep into a project and then the code base gets kind of complex, and then you just say, "I just want to start over." And then you start over with something smaller, which is lower complexity. But it takes you a long time to just get back to status quo. But now it's lower complexity. And then at some point it starts to get complex again, and you say, "I don't know, let's just start over." It is almost always the case that what's happening is parts of the code base are rotting, and there is no mechanism for keeping the documentation up to date. And the assumption that a lot of people have is once it's shipped, then it's done. But really, you just created a new evergreen obligation for yourself. Every new surface that you add is an obligation to maintain, maybe forever, is what you have to-

    9. TF

      What do you mean by surface?

    10. SC

      As in, like, if you create a new screen on your app, you now have to maintain that forever.

    11. TF

      Mm-hmm.

    12. SC

      Or somebody does.

    13. TF

      Mm-hmm.

    14. SC

      It doesn't just... It's not just done, and then you have... You can move on with your life. You always have to have some process for saying-

    15. TF

      This is your bonsai garden.

    16. SC

      Yeah, exactly.

    17. TF

      [laughs]

    18. SC

      You have to constantly come up with a process for, hey, this screenshot that we just made on this new website, this will be out of date next time we update our app.

    19. TF

      Mm-hmm.

    20. SC

      And so you have to create a process for on some regular basis, maybe weekly, maybe monthly, check is the current state of our app aligned with the screenshot of this surface. And then you have 50 surfaces, you have to check all of them to make sure. And if your conclusion is, that is too much maintenance, then the answer is, well, then you need fewer surfaces.

    21. TF

      Mm-hmm.

    22. SC

      And you need to figure how to reduce that complexity of maintenance.

    23. TF

      Mm.

  32. 2:14:53 – 2:24:02

    Raised secularly, what does Sam get out of theology?

    1. TF

      So next, I would like to chat about your sabbatical briefly, and that may not be the term that you would apply, but you took a year off after your last company, and you studied two things, theology and network theory. Why did you choose these two? And I understand these words separately, but honestly, I have no idea what network theory refers to. So how did you choose these two, and then could you please explain network theory and what has come of that?

    2. SC

      Yeah. So I had a whole list of topics. Some of them ended up being much simpler or more shallow than I was expecting. One that was simpler, I had on my list of things-

    3. TF

      Bigger calves. How can I get bigger-

    4. SC

      [laughs] Yeah

    5. TF

      ... bigger calves? [laughs]

    6. SC

      One, one of them was getting up to speed on the state of, of AI. This was four years, five years ago now. And the last time I had done it was maybe 10 years ago, and it was really hard. There were no libraries, there was no real tooling. And then next time I get into it, a friend recommended the Fast.ai course, and it was so easy.

    7. TF

      Mm.

    8. SC

      My goal was to create, to create something that can recognize images of cats, and it was literally the tutorial [laughs] in Fast.ai-

    9. TF

      [laughs]

    10. SC

      ... was to recognize images of cats. I had planned to do three months on this, and I only ended up spending maybe a week on it, 'cause I was like, "I get it now. I see what this can do."

    11. TF

      Mm-hmm.

    12. SC

      And so theology was one that I became interested in because my-

    13. TF

      Lots of books available.

    14. SC

      Yeah, for sure.

    15. TF

      [laughs]

    16. SC

      I, I grew up... My, my father is Jewish and secular. My mother is, like, Richard Dawkins style atheist.

    17. TF

      [laughs]

    18. SC

      And so I grew up not really knowing anything about religion.

    19. TF

      Mm-hmm.

    20. SC

      We went to temple every once in a while, but more as like a cultural thing. And if I'm being honest about it, I probably spent the first 25 years of my life generally condescending towards religious people.

    21. TF

      Mm-hmm.

    22. SC

      And then as I got older, I kept recognizing that these people who I knew were smarter than me were also religious, which was very strange.

    23. TF

      [laughs]

    24. SC

      Because this would be a really big oversight.

    25. TF

      Little, little cognitive dissonance.

    26. SC

      Yeah.

    27. TF

      [laughs]

    28. SC

      It's like, how is this possible? And so I, my conclusion was that there's something about religion. It is more likely there's something I don't understand than it is all of these people smarter than me are missing something that I think is obvious. And so I, I spent a lot of time. I interviewed a whole bunch of my religious friends. I went to a Bible study class for 10 weeks, so a Christian Bible study, and it was really, really interesting.

    29. TF

      May I ask you a question?

    30. SC

      Yeah.

  33. 2:24:02 – 2:27:32

    The perils of postmodernism.

    1. SC

      time.

    2. TF

      Mm-hmm.

    3. SC

      And I would say one of the things that came out of it more than anything was an appreciation and a deeper respect for the positive aspects of religion and what-

    4. TF

      Mm-hmm

    5. SC

      ... it does for people. I think the deep dive into epistemology also was pretty mind-bending, where it caused me to recognize that, this is actually something that I'm still wrestling with, is that I really do not believe there is such a thing as objective truth.

    6. TF

      Mm-hmm.

    7. SC

      All truth is subjective. You can maybe asymptotically approach truth, but there is no such thing as objective truth. The only way to believe in that is to believe in some specific higher power. Where I struggle with it is that that path almost always leads to postmodernism and to really bad things. And so I struggle-

    8. TF

      Could you define just what do you mean by postmodernism here?

    9. SC

      Postmodernism meaning, like, your truth is just as valid as anyone else's truth.

    10. TF

      Just, like, complete moral relativism-

    11. SC

      Yeah

    12. TF

      ... across the board

    13. SC

      ... 100% moral relativism is exactly. It is-

    14. TF

      Mm-hmm

    15. SC

      ... postmodernism in a nutshell. It's like your truth is just as important and real as anybody else's. There is no commons that we can agree on.

    16. TF

      Right.

    17. SC

      It's just purely individual truth is all that matters. And that, that leads to bad outcomes.

    18. TF

      Mm-hmm.

    19. SC

      Just in every society that has these postmodernist beliefs, Marxism as an example, tends to lead to really bad outcomes. And so I'm still struggling to figure out how one believes that without leading to some really negative outcome.

    20. TF

      Hmm. One of my pet theories I've had for probably four or five years now, watching the development and ubiquity of, say, social media, and watching elections, and watching very sophisticated sort of disinformation, misinformation campaigns, and how people, I don't want to say by and large, but a lot of folks have ended up in this post-factual, you just can't know what is real, apathetic state. And some people certainly then kind of bleed over into nihilism for a lot of other reasons.

    21. SC

      Mm-hmm.

    22. TF

      But my theory, that's more the observation that leads to the theory, which is there's going to be an ex- like a Cambrian explosion of religions. They may not self-describe, the people who lead these things, even if they're distributed or self-identify, may n- may not describe it as religion, but it's going to look a hell of a lot... It's gonna, you know-

    23. SC

      Yeah

    24. TF

      ... look like a duck and quack like a duck, but maybe it calls itself, you know, aquatic chicken.

    25. SC

      [laughs]

    26. TF

      Okay, fine.

    27. SC

      Yeah.

    28. TF

      But [laughs] ...

    29. SC

      I think so too.

    30. TF

      I, I think there's gonna be a lot of sort of micro, micro religions that pop up.

  34. 2:27:32 – 2:42:00

    Network theory and relationship management.

    1. SC

      Oh, cool.

    2. TF

      Which very quickly gets to the challenge of labeling.

    3. SC

      Yeah.

    4. TF

      And has a lot to do with political powers that be. It has a lot to do with scale, size. Right? If it's five people just doing some, you know, Wiccan earth goddess thing, it's, it's quite different from, like, five million doing the same thing. And raised a lot of very, very fascinating questions for me that I want to unpack with him. So theology, topic number one. Network theory.

    5. SC

      Yeah.

    6. TF

      What is this?

    7. SC

      So this was another topic that I, I was particularly interested in more understanding from first principles. A lot of people know things that are tangentially related to network theory, like the Dunbar's number, 150 people. People have some general sense that, you know, having a strong network is good.

    8. TF

      Mm-hmm.

    9. SC

      And I wanted to better understand it from first principle. So it's both network and graph theory are sort of the two related topics. Network theory, in my experience, is the language that people typically use for interpersonal human networks.

    10. TF

      Mm-hmm.

    11. SC

      And graph theory is more math.

    12. TF

      Mm-hmm.

    13. SC

      I did a, a gratitude exercise maybe five years ago during the time off. I just listed all the good things that have happened to me in my life.

    14. TF

      Mm-hmm.

    15. SC

      I think I listed 100 things was the goal. I think 97, 98 of them were because of somebody that I knew, not because of something that I did.

    16. TF

      Mm-hmm.

    17. SC

      Which was really surprising. And so I decided I'm gonna really put a lot more attention towards who the people are in my life. And so I, I set a goal, which I still have, of keeping up with 1,000 people that I care about every quarter.

    18. TF

      Holy shit.

    19. SC

      Yeah.

    20. TF

      That sounds like a lot of people.

    21. SC

      It's a lot. I mean, it, it takes-

    22. TF

      Why did you choose that number?

    23. SC

      Because it felt-

    24. TF

      100 was too easy.

    25. SC

      Yeah, 100 was too easy.

    26. TF

      10,000 was way too much.

    27. SC

      Yeah. Basically, yeah.

    28. TF

      [laughs]

    29. SC

      That's basically it. Like, a th- 1,000 felt tractable, but hard. I probably haven't hit 1,000 in a quarter in maybe two years, but I regularly exceed 500.

    30. TF

      I feel like my cortisol has, has spiked so hard-

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