What Is the Difference Between Gmail and Outlook?

“Because there’s so much information to pass and so many transactions that we need to transact every day, having that moment to properly think and work through a big idea is challenging. I find that especially difficult in my work today as a venture capitalist where synthesis is the core skill. It’s important that we find the time to think and the tools to help us think.”

– Phil Morle

What you will learn

• How to enable synthesis whether alone or with others (03:10)
• What are some good information sources, and routines? (06:32)
• How to gather an information “mise en place” (09:50)
• What is the Roam app? (13:20) 
• What is the fundamental difference between Outlook and Gmail? (14:56)
• What is the difference between Roam and Obisidian? (17:28)
• How do venture capitalists manage their information overload? (20:46)
• Why clarity of purpose is crucial to thriving on overload (27:54)

Resources

• Obsidian
• Roam Research
• Tana
• Readwise
• John Borthwick
• Tools for THINKing
• Rob Cross
• Finite and Infinite Games by James Carse
• Oblique Strategies Cards by Brian Eno
• Oblique Strategies for iPhone
• Oblique Strategies for Android

Transcript

Phil Morle: Glad to be here, Ross.

Ross: This is a topic you’ve been thinking about for a long time. I just dug up something which you wrote in 2007, saying we are becoming good filters but poor philosophers. We are good at information retrieval and storage, but not so good at the long thought. We need time to think. Do you still agree with what you said 15 years ago?

Phil: I do, and if anything, it gets harder, doesn’t it? Because there’s so much information to pass and so many transactions that we need to transact every day, having that moment to properly think and work through a big idea is challenging. I find that especially difficult in my work today as a venture capitalist where synthesis is the core skill. It’s important that we find the time to think and the tools to help us think.

Ross: You just mentioned synthesis. Let’s get to that, there are a lot of elements that precede the act of synthesis. How do you enable that? Is this a state of mind? Is this giving yourself the space to think as we mentioned? What is it that enables you to synthesize all of the signals that you get?

Phil: I’m a real thought hacker, and I’m just trying everything, every notebook, every tool, every meeting format. I do have a system that I like and it’s ever-evolving. I must say that coming out of COVID, one of the things I like the most is getting back in front of a whiteboard with a bunch of people because synthesis really happens wonderfully with a team. For example, I just spent some time with the team working on the pitch deck and just workshopping that with them. Because we were in a conversation, all this stuff was coming out of their mouth which was super rich and super interesting and was much more valuable than the very dry stuff that was in the pitch deck which is the kind of stuff you do natively and powerfully when you’re sitting on your own in a room with a screen in front of you.
Of all the tools that I have, sometimes the best tool is a whiteboard, a marker pen, a couple of people, and ideas. It forces yourself into other spaces. When we go into digital spaces, that’s where I need that equivalent of other people, like, what are the prompts? What are the processes on rails that pull you through, that forces me to do that rather than just to get my emails done and just transact, transact, transact all day? How do I force myself into that position of thinking like I’m with some people on the whiteboard?

Ross: I’d like to come back to the process but first of all the whiteboard. If you’re on the whiteboard and you’re having a wonderful conversation, what does it look like afterward? Do you have any patterns for the sorts things you put on a whiteboard?

Phil: I’m a very visual person. I like connected tissue, so I suppose mind maps would be the most likely outcome for me. I’d say my whiteboards are either a mind map spider or a grid with a timeline with different dimensions to the timeline. From a venture perspective, so much of what we do is about what might be the story that plays out over time and what are all the different layers to that story. That’s what might get us to the grid, but the synthesis really comes from the mind map. That’s where you get all these strange connections in a graph that you might not have thought to do had you not co-located those two bubbles next to each other.

Ross: You have mentioned more recently as well as earlier in all of the wonderful stuff that you share online that you do have some processes and workflows. The one we started at the beginning as in input, what information sources do you find? Are there particular times of the day or any particular approach that you take to getting the crude, raw inputs that go into your thinking?

Phil: This is really important for me because come eight o’clock in the morning, I start getting smashed from every digital channel, my phone rings, the emails come in, about 10 different portfolio companies and their Slack channels light up, one company might have a big win, and another might be having a disastrous situation, and the day just goes right out of control and it’s all inbound information. The first thing that I do in my life, which I found really helpful, and I enjoy enormously now is I start my day really early. I start my day at four or five o’clock in the morning. It’s me-time, it’s synthesis time, it’s reading time, it’s putting together the plan for the day, it’s making sure I’ve collected everything from yesterday that I haven’t got to yet. The collecting of information and things to do and insights is something that just has to be incredibly quick, and frictionless because that’s how I don’t get stressed about it, I know I’ve captured it, and I know that my process will have a loop at some point where I come to it, I might pick it up, and I put it somewhere, and I do something with it.
I’m one of those people who doesn’t like an open loop and doesn’t like feeling like I’m in somebody else’s open loop, so I don’t like to do that to other people. I have a whole series of tools that I use for doing this. The biggest change for me over the last year is to become a disciple of tools for thought as they’re becoming known. This is tools like Obsidian, Roam, and now a tool called Tana, which has become the epicenter of my work. You can think of it as an outliner, in its simplest form, but every bullet in the outline is a node in the graph, and all the graphs link together. If I say, I’m having a meeting with Ross Dawson, then the word Ross Dawson leads me to the entire history of everything we’ve done together. In that same thing, we’ll be making notes about all kinds of things and they all start linking together. It’s not a structured database, it’s a graph. This really helps me to think, and throughout that, there are prompts.
I think of it as having a habit like a chef comes into the kitchen, and you prepare your tools for the day, chop your carrots, prepare your herbs, have everything lined up, partially cook some things, so you’re ready. Then people start coming into a restaurant and the world goes mental but you just grab the knife because it’s in the right place, you grab the carrots that you’ve already chopped too, you’re ready, and you’re not panicking trying to find the basic things.
Every day when I open up my Tana, I have a prompt that asks me if I’m playing the infinite game, this is my reminder each day to behave a certain way. I then have a startup routine that I have to do. For example, there’s a series of checkboxes. The first one is start music. The reason I have that is that I have to focus, and I struggle with that sometimes, I can have just a noise of tasks in my mind and priorities, all competing, or I just might be brain-dead, still half asleep. I know that if I put my headphones on and I press play with the right playlist, it’s like an ADHD tablet. I’m just voof, I’m zoned in. It’s amazing how without the prompt, I’ll think, today, I’ll just sit here quietly and listen to the birds outside. That’s what I’d like to do. Every time I do that, I have a really ineffective hour. Some people would say, maybe you should do that, Phil, allow yourself to have an ineffective hour. I know if I put the headphones on, I’m in the zone.

Ross: What’s the right playlist for you?

Phil: Just a number of electronica, some experimental soundtracks, the theme is no lyrics. I almost don’t have any famous artists, I just go into this voyage of discovery into all the worlds of Spotify, but, just having something with a little bit of a pulse to it, just gets me into the zone, and then I can start getting things done. Then I just literally have checkboxes for just basically where all my inboxes are. I have some inboxes in Notion where team things come in, I have inboxes in my email, I have things to read in Readwise reader, so I collect those. Then, if I can get it all done in the morning, I’ll literally process those things, I’ll go through it, I’ll reply.
One of the most important ones is just “review yesterday.” In Tana, I can just click a link, yesterday comes up, I can see everything I did, and I can do a search of all the tasks that came up yesterday. I have this little list that I call the snowball, which is just all this stuff that’s not been done in the last three days that’s accumulated. It’s my whack-a-mole, just to get those things done. That whole process just keeps me on rails, I know where everything is, I’m collecting everything as I go, so when I do have a moment to synthesize and think and process, I know I’ve got everything now and I haven’t missed something.

Ross: You’ve written as far as I could find six posts about using Roam as a VC. Roam is something that could be described in many ways. I’d like to hear you describe what Roam is. Most of the listeners will probably not be using Roam but tell us a little bit about how you use it.

Phil: Roam is a brand new paradigm that’s really difficult to describe, you know why it’s valuable when you start to use it. I think most people are familiar with hypertext and the way the web works, you can make a link that shows up in blue text or whatever on a website, and if you click on that link, it’ll take you to a page that you’ve made at another URL behind the link. But you have to manually go and make that page. What happens in Roam is this idea of these two-way links. In Roam, it’s two square brackets. If you go at meeting with [Ross Dawson], it’s immediately made a node in the graph for Ross Dawson. Then at any time, I can click on Ross Dawson and see the entire ledger of activity that Ross Dawson and I have been going through over time, and it’s by date and any other tagging and everything that I want to do. What that means is, you’re never trying to decide where to put something. It’s like the difference between Gmail and Outlook. Are you an Outlook user or a Gmail user?

Ross: Gmail for some time now.

Phil: Outlook users are frenetically trying to manage this folder system, where it has got these folders down the left-hand side, you’re going, where does this email go? And then Gmail said forget about that, let’s just make the search really good. This is the same. You just tag things as you go. and everything just shows up at the right place. Next time I go meeting with Ross Dawson, I’ve got my entire record of all the other meetings we’ve had instantly there, doing no work for it. You can also do things like time travel. You can say, meeting with Ross Dawson in two days, and then write some notes underneath. What happens then is in two days, those notes show up, right when you’ve got that meeting. It’s just fantastically powerful.
The reason you understand it later is you just start using it. In the beginning, you feel really uncomfortable because it feels like, I’m not filing anything, I’m just making notes, I’m putting them down everywhere, and then three or four days later, you meet the same person the second time, or you go back to an essay you were writing, or some research that you’re doing, and all the information there is just automatically clustered. It’s incredibly valuable. I converted a lot of people that work into it, and my son is a devotee as well. It’s very good software.

Ross: You also mentioned Obsidian a little while ago. Obsidian is usually considered an alternative to Roam. Are you using both?

Phil: I did try Obsidian. Obsidian is beautiful software. From my perspective, the difference between Obsidian and Roam is Obsidian is not a graph-based database, it’s a much, much better version of Evernote, to put it very, very simply. Still, you’ve got a series of markdown file notes that you’re collecting, and you’re having to think about where things go, but it’s very, very powerful. Many people use Obsidian when they’re writers, for example, and it’s got a very nice interface for writing longer-form documents and things like that, and still having some element of a beautiful, easy-to-use note-taking system. But Roam, I tried to leave Roam because it’s ugly and hacky, and Obsidian is beautiful but it didn’t work like my mind, these things come down to that in the end, you have to map to what’s going on in your own brain, so I went back to Roam.
That’s why I’ve now moved to Tana, you can tell an early adopter, crazy person here, but Tana is basically building upon the Roam paradigm. At the heart of Tana is this idea of a super tag. For example, here, what I’ve done is for this session, I’ve got a meeting with Ross on productivity, and I tag it as a meeting, which is just one that I’ve made, and then because of that, it has automatically dumped in all the metadata underneath for all the things I want to get out of this meeting. It’s the life on rails again.

Ross: Are you using Roam concurrently with Tana or have you shifted completely to Tana?

Phil: No, moved all over. You can import Roam. My Roam graph is in Tana now.

Ross: I use Obsidian, so still need to play around with other alternatives. But now a profusion of tools is coming out so if you’re trying to keep across what there is, there is this wonderful thing. Interestingly, John Borthwick of Betaworks, his latest camp has been “THINKing” tools. That’s his latest investment theme. As he does it, there’s still an enormous opportunity in the space. It’s still very fragmented. All of these mentioned tools, Roam, Obsidian, and Tana are still basically for geeks.

Phil: Yes, they are. You’re right. It’s a paradigm that maybe goes back to how we began this conversation that it gets harder and harder to synthesize in a heavily transactional world, and what are the tools that are going to help us to do a better job of that and this whole tools for thought category has emerged.

Ross: I think that venture capitalist, VC, is like the epitome of information overload because you not only need to keep in touch with your own industry but also your portfolio companies, and be able to keep across new companies coming up but also the underlying technologies that are driving all of those domains, and particularly with you working in deep tech, everything is new whichever way you’re looking. You do refer in some of your posts particularly how is this relevant to VCs, and I’d like to just unpack that a little bit. What are the things which are specific, or informed by, or where the VC world can teach us about useful processes or workflows?

Phil: I describe it as being like a fire hose of information. From the first encounter with a human in the morning to the last encounter at the end of the day, it’s just this information coming in. My calendar app has this feature called rewind, which I looked at last week, and it told me that I met 1788 people this year. Then for each of those people, they were talking about really complicated things like making proteins or enzymes that recycle plastic in different ways and things like that, so collecting the information that comes out and synthesizing it. With some of the people, there’ll be very quick meetings, there’ll be like a 30-minute quick meeting to try and find a fit, understand where someone’s coming from.
I have a principle where I want everybody to get some value out of every meeting. I try and think about how to do that, which means I can’t use the whole 30 minutes, just small talking. It’s just a massive amount of information. Again, that’s why this need for inputs is really important. How can you effortlessly capture something and drop it into the system to do something with it later, and collect a record of everything, that’s why these tools for thought are just beautiful for venture capital. A lot of venture capitalists use them.

Ross: Do you build any meta frameworks as in thinking about a particular domain, and try to build a lattice of knowledge around that particular area?

Phil: At the simplest level, what I like to try and do when I live my life on rails is even when you’re having a bad day, how do you perform at your best? Even if I’m tired and fed up or stressed about something but I have to meet a founder who’s working hard on their business and it’s really important to them that it comes across well and they want to get some value out of the meeting, I make sure I’ve got a good framework that asks me questions and also helps me ask them questions. Then I collect it all in a similar format, and it’s just a scaffold, it doesn’t have to play that way but it means I can if that’s what I want to do. Then that also means that as we go through, I can start looking at things on aggregate, which takes us back to the synthesis, I can start querying things based on the similar answer to the same question that multiple people create, which is quite interesting.
The other thing that I try and do throughout is I have a journaling and insights framework, which again, I can just collect it very quickly into these systems. Then at the right time, when I’m doing my weekly planning and things, it all comes up to the surface again, so then I can see something that was just quickly collected whilst I was walking down the street, or in between meetings, or in the middle of a pitch session or whatever, I can just collect it, move on, and then I can think more about that insight at some other one of my five o’clock in the morning sessions.

Ross: Are there any particular elements that scaffold that you described? Is it a series of questions or particular facets of what it is you’re trying to uncover?

Phil: Yes. For example, a new thing I’m doing at the moment is, because so much of my work is in a meeting with somebody, I’m trying to figure out which ones fuel me, and which ones drain me, of course, you still have to do some of the ones that drain you whether you like it or not, that’s life, we’ve got to do a mix, but what I’ve started doing in my scaffolding is every meeting I have, I have to give it a score, like, whether it drained me or fueled me. Then what I can do is when I’m doing a bit of a review, I can just look at my week and go, okay, look at this pattern here, this meeting just keeps coming up and it’s draining me, so what do I do? Maybe I don’t need to be in the meeting? Or maybe I can redesign how the meeting actually happens so that it’s more impactful and more fun and things like that. Again, if you just collect it in the scaffold, it’s just a very simple thing, it doesn’t add much, there’s zero workload, basically, it just takes half a second. But then the insight that gives at the end of the week is terrific.

Ross: That could be valuable to other people, I did some work with Rob Cross, he was at the University of Virginia at the time, around energy and networks, where essentially, you can map organizations by whether people are perceived as energy givers or takers, that actually provided some pretty strong insights into organizations, but also context. Because again, it’s not just the individual, it’s also the context, somebody who may be energizing in one context but not in a particular type of meeting, for example. There’s a lovely lattice of information that you can get if other people follow that as well.

Phil: It’s good just to be mindful of it and understand what’s going on. I’ve been having this conversation recently, for example, here we are, it’s the first year on the other side of COVID, we’ve all rushed out gobbling up the world again, nearly everyone I know has been phenomenally busy this year and is exhausted, and to your point about the meetings and energy givers and takers, each face you’re seeing around the room or on the Zoom screen or whatever is loaded with stuff on there at that moment that you don’t generally acknowledge in a meeting, but it’s in the room.

Ross: In a minute, I want to get a summary from you, and also anything which we haven’t covered. But to your point about making sure that you get as much value as I have from this conversation, hopefully, part of it has been able to share, be aware of what you’re doing but are there any questions you have for me or anything, which would help you make this a useful conversation?

Phil: You’re the expert. I’ve told you some of the things that I’m doing. How do I level up what I’m doing to get better at this fire hose?

Ross: The big thing for me is always that you have some clarity. This is what I describe as a personal information plan. This maps out for me saying okay, defining your purpose, and whatever ways. There are a couple of layers to that, from The Infinite Game through to what is the impact you want to achieve, framing different aspects of your life, thinking about your relationship to the areas of expertise you want to develop, what those are, your ventures, your well being, your family, what in the news more broadly is relevant to you or not. From that, the time boxing for where it is you’re focused, in terms of information activities, where it is you are making time for regenerating.
It’s an interesting thing. I did refer to the improvisational theatre in Thriving on Overload, the book, as just one tool for how it is we get to a state of mind of synthesis. You have a background in theatre. That’s something where it’s not just that activity, but there are also other spaces that we can put ourselves in. Synthesis is, yes, partly being able to have all of the pieces of information connected but part of that is also how do we find for ourselves what are the spaces or the states of mind in which those can things, and what are the right times of day to be able to do that? How do we get to those places? This is the conscious-unconscious nexus, and how we pull that together? You’re probably better than most having lived in arts and technology and business and pulling that together.
I think part of it is making the whole as much as possible. Again, in Thriving on Overload, the book, there are many tactics or more broadly, this framework of starting from purpose and flowing through all of the elements of the information inputs in the frameworks you build, and enhancing your ability for attention and ending up at that synthesis, which in a way goes beyond the conscious mind or anything that the technology can support.

Phil: One of my favorite hacks it’s called the Oblique Strategy Cards that Brian Eno wrote.

Ross: I haven’t seen those.

Phil: They’re designed for if you get stuck, if you get writer’s block or artist’s block and you’re procrastinating, and the idea is you just pick a card, and then you do what it says on the card. This one says courage, this one says accept advice, this one says voice nagging suspicions, use an unacceptable color, and it’s great. When you get a bit stuck or a little bit bored, you might be writing a dull report for somebody, you can pick a card up and make it a bit more fun, so that’s quite a good thing to do. What about “The Infinite Game”? That’s a new thing for me. I’m very interested in it. Have you seen this in play in the world in any interesting places?

Ross: I read James Carse’s original book, Finite and Infinite Games, a very long time ago. It’s been implicit. The quote which I have used in more keynotes than any other is finite players play within boundaries, infinite players play with boundaries. I’m always attuned to that. Just an example of that is my first book, I’ve gone into the field of knowledge management, and the first thing that hit me is this is all about internal, how about outside, knowledge outside and across organizations and relationships? I wrote a book about that. I guess all of my framing has always been going beyond the boundaries or playing with the boundaries. What is delightful today is how organizations and value creation and ecosystems and everything is going beyond boundaries. In a way that finite and infinite game almost best expresses the ecosystem because it has to be, in fact, you are participating, you’re not separate from everything else.

Phil: That’s right. You’re at the service of something bigger and it is unacceptable to get to the end because if you’ve got to the end, you’ve made it too small.

Ross: Yes.

Phil: I love it. It’s a good reminder. Whenever I feel too competitive or feel envious of somebody or something like that, the reminder that I just need to play the infinite game helps me get through.

Ross: Any closing comments or recommendations or things we haven’t covered that could be useful to our listeners?

Phil: I’m a bit of a nutcase when it comes to these systems. I’m sure listeners can tell, I’m an early adopter, and I’m an early adopter because I’m constantly looking for what’s going to give me that extra edge, that extra 10 minutes, that extra bit of ease, that extra ability to capture things and not worry about them. There’s something a little bit obsessive about it, and I find the balance that I have to have is how to then let go of it. What I do is I find myself going into a phase where I lock in a new habit, and the new habit gives me a new capability of some kind, it either works or it doesn’t work, but then I have to consciously step outside of it for a while and let it just relax a little while. Life is on rails, it’s helping me because it’s on rails, but it doesn’t have to be on rails, I can step off the train if I want to do that, and I think that’s important as well. Otherwise, I’d just be a bit of a robot. There are some amazing tools out there to help us today.

Ross: Fantastic. Thank you so much for your time and your insights, Phil. I really appreciate it.

Phil: Thank you, Ross. Great chat.