Silicon Valley Secrets for Scaling with Gokul Rajaram

In This Episode

• [08:46] – Gokul Rajaram shares about the most meaningful thing he has built or created.
• [10:29] – Gokul highlights the importance of experimentation and trying new things with AI tools.
• [15:15] – Gokul and Stephan discuss the importance of email triaging and using the Getting Things Done (GTD) concept to manage tasks and projects.
• [24:01] – Gokul suggests pre-mortem and post-mortem strategies for anticipating and addressing potential risks in projects.
• [31:39] – Gokul emphasizes the significance of pre-work meetings, including a clear agenda and prepared documents.
• [38:08] – Gokul describes a decision-making framework called S.P.A.D.E used om Silicon Valley, which involves evaluating alternatives and reaching a decision through private voting.
• [46:39] – Here’s how you can connect with Gokul.

Jump to Links and Resources

Gokul, it’s great to have you on the show. We have known each other for so long, and it’s great to finally do a podcast interview with you.

Thank you for having me, Stephan. It’s crazy how long we’ve known each other, right? The world was very different almost 15 years ago when we first met, and it’s great to continue to stay in touch and to do this podcast together. Thank you for having me.

Thank you. So I would love to have you share a bit of your origin story, how you went from living in India, and probably would only dream of achieving what you have already accomplished. That might have seemed like something impossible as you were growing up. Walk us through how you turned this dream into reality.

I think it’s funny. My dreams have been very much about working on things I enjoy. I enjoyed math. I didn’t even know what computer science was in high school, and I knew I wanted to do something relevant to mathematics. When I went to undergrad, I discovered computer science, and I was lucky enough to be there, where there was a competitive entrance exam in India. Many of the seats in engineering colleges are decided, or you get admitted based on your rank in the entrance exam. So you’re kind of trained to be pretty competitive in terms of exam taking and so on. The scores are ranked in absolute order.

In software development, a pre-mortem involves identifying potential issues before launch and creating mitigation plans for each, which empowers teams to anticipate and address problems proactively. Share on X

The grades are less important than your rank. You could have whatever grade you have, but you could be ranked whatever. So, I think my interest in math led to an appreciation and discovery of computer science in the early 90’s, which ultimately paved the way for me to come to the US for grad school. I was considering staying back in India, but I talked to a few of my friends who had come to the US for grad school, and they talked about just the opportunities that computer science graduate programs opened for them working in the industry.

Back then, it was nascent. I remember very well. I had read about the Mosaic browser being developed in 1994, and the first thing I did when I arrived in Austin for grad school at UT was run into the computer science labs. There was a student working, and I said, “Please, can you please show me what the browser looks like? Because we didn’t have access to the browser,” someone showed it to me, and that was mind-blowing, just seeing a website. Now, it seems obvious, but if you think about it, it’s the file hosted on another server, and you can see it visually in a browser.

That was just incredible. It just seems crazy to say that, but in 95, this fall of 95, that was just mind-blowing. And so that was the seminal moment that I decided that this is the space I want to work in for the rest of my life. I left the PhD program early to join a company building free email and Internet services for people. I like the mission where the same service now you want to make it available for free called Juno. You might remember it was a very early free email service. Along with NetZero, they merged to form United Online, and then from there, I took a detour to business school and was super lucky to join Google again. It’s all about helping people find information online, democratizing access to information, and then, from there, various other things.

But really, it all was catalyzed by an interest in computer science. Then, there was Marc Andreessen’s browser creation, which I think was still underappreciated. I mean, email existed for decades before. I used email from India to email professors and others in the US, but the browser just catalyzed. I spent so many nights at UT in the lab, just throughout the night, just creating my website, learning HTML, learning CSS, and slowly learning JavaScript as it came on a few years later. Java for a while. I mean, it was just every time you tested it, and there were so many. Every website back then was a blinking crazy thing because you were just testing and trying out new things. I’m sure it was the Wild West of the Internet, and SEO was much easier than it is now.

But there was no SEO back then, and there was no Google. But yeah, what great days we all had. I’m sure the pioneers were the early folks in each part, whether it was a PC, in our case, or the browser. We all look back and say how far we’ve come. And now, someone young and starting their career just takes this thing for granted.

Yeah, those were fun times. I have a similar story to you: I was studying for PhD myself, and I dropped out because I got enamored by the Mosaic browser. I decided to build some websites just for fun and volunteered to build a website for my department. I was studying biochemistry at the University of Wisconsin-Madison, so I ended up speaking at a conference. Not speaking, it was more like presenting a paper; I got a big poster board on how to use the Internet to convey 3D information about virus structures because I was studying viruses. I remember meeting Tim Berners-Lee briefly at this conference. It was the Second International Worldwide Web Conference. And I also met Rob McCool.

And I got to have a conversation with Rob. Do you know who Rob McCool is?

Yes, I do. 

So, Marc Andreessen poached him to join Netscape and build the Netscape server because he coded the Apache Server. At the time, it was HTTPd, the NCSA server, and then after the Netscape server, he coded Apache. And I just was enamored by it all. I thought, “Okay, what am I doing studying biochemistry? I’m going to become a professor and just have this crazy low-paying job for the rest of my life, and I’m trying to fight for tenure. What am I doing?” So, I dropped out, and the rest is history. 

Both of us dropped out of PhD programs, we have that in common, basically because of the Internet. I’m sure hundreds like us just said, “Got to just go build back before there was;” I didn’t think of myself as a builder. I just wanted to experiment and work on this amazing technology out there.

Yeah. So, what’s the most meaningful thing you have built or created? And it could have been way back when you were a kid. It doesn’t matter. Something that really pops for you is, “Wow, I’m really proud of this.”

I think it’s part of a national; there was something called quizzing in many of the UK and affiliated countries, like countries where the UK used to be. It’s basically similar to a quiz bowl or something in the US. When I was growing up, I was really into quizzing. So I won a pretty big quizzing competition, which is a rapid-fire general knowledge exposition where you’re either part of a team or by yourself. So, I was a solo participant in a quiz show contest. It was a state-level contest, and I finished first in it.

There were multiple rounds, and that was one of my proudest moments. I also played badminton, I was not an athlete, but it was more at the district, and I was not super good at it, but I enjoyed playing it. But I really enjoyed quizzing because I loved absorbing information of all kinds. So, I’m really proud of winning quiz contests, and I used to go and attend and do parts of winning some big high-level quiz contests.

AI can not just help you in your profession; it can help in your day-to-day life.

So, what would be important for our listeners to understand about product engineering and development, including everything from mobile apps to websites to software as a service and systems? What will help our listeners take more advantage of the opportunities that things like AI and the advancement of technology are providing for not just marketers but also business owners, for everybody, really?

I think the biggest thing I would say is to keep trying new things. Tinkering is the most important thing. In other words, it’s so accessible now through ChatGPT to all these other tools unless you use them. So, make a resolution and set half an hour aside in your calendar every day or even 15 minutes to try something, and you’ll be amazed at its capabilities. For example, I was trying out this negotiation tool I found, and crazily enough, the AI does a very good job negotiating. I’ve heard of people who took it because AI can not just help you in your profession; it can help in your day-to-day life. For example, if you are negotiating over email to buy a car from a dealer, it is very likely that taking the dealer’s response and feeding it into AI will give you a good response to send back. And I’ve heard of people negotiating this way and getting the dealer to lower their price and buy a car.

I think of almost any situation in your life where you’re blocked or stuck. It could be planning a trip, negotiating with a car dealer, or writing a memo or a draft. It could be writing an email to a loved one, a difficult email. I promise you that AI will be able to help with each of those things and make your life easier and better – think of AI as a super smart assistant. Maybe not as socially savvy, but extremely knowledgeable. Like someone who can win any quiz competition ever created and is infinitely patient with you, will never rebuke you. I’m never going to say, “I’m done; I’m tired of this.”

I am never going to say the tireless, indefatigable, extremely knowledgeable assistant you have at your fingertips. But try it. That’s what I’ve just started trying out for different situations, personal, professional, etcetera. And every time I do it, I just get an unlock. Now, I use it for drafts of things I’m working on, emails I’ve sent to people, and even personal situations, emails, and negotiations. And you just find it seeping more and more into your life. That’s a great thing.

People use AI for counseling now.

It’s not just professional; it’s also personal. It’s almost anything. People use AI for counseling now. There are companies, and there are enough companies that I’m sure you will use for your symptoms. I’ve used it for my symptoms. Oh, I’m having an ache here. As you get older, you have aches. What could this be? If something is wrong, what should I do? And my goodness, what are the top three? And it identifies, and you go to the doctor, and it’s one of those two.

So it is extremely good and getting better all the time. All the time.

So, how much time do you spend on a daily basis in AI? Whether it’s ChatGPT, Claude, some other LLM, or it’s some sort of specialized AI tool, 

Probably a few hours a day. I have a ChatGPT, Claude and Bard or Gemini. I forgot what it’s called now. All three are in three different tabs, and I have many products. I’ll put the same prompt in all three and see which one. That’s the other thing. We have access to all three now. Think about it. If someone told you you could get an assistant for $0 a month, would you, the human assistant, you would say, get me like 100 of those?

And so I’m surprised.  I mean, I think the number one thing is to make sure you go to the highest, best version of the ChatPT and the best version, many of them are paid versions. The difference between GPT-4 and GPT-3.5 is massive. You can upload images into GPT-4 screenshots, and it will analyze them and do stuff. It is also multimodal, which means if you ever have to do a sketch or a drawing, I’m not a very good artist, but it is so much easier to generate art now for articles, content, and other stuff through these AI tools. That is incredible. It’s now become my companion to my email and other stuff I do. I always have it open in three tabs, and I’ll input the same prompt into all three of them and see which one is what.

I have three assistants with different strengths working, and that’s awesome. I can see which one I like best and use that.

Yeah, you probably would like this tool called ChatHub. ChatHub has all the windows set up for ChatGPT, Claude, Bard and Bing. You can have conversations with all four of these simultaneously. It also can juggle Llama, Perplexity, and so forth. Instead of having all these tabs open, you can have it all through one interface, and it tracks all of it. 

So, how do you manage all the tasks and projects you have going on at any particular time? What is your project management tool of choice? Is it Asana or ClickUp? Some other programming-focused tools for project management? How do you do this?

My whole approach to efficiency came from 20 years ago at Google. There, a person came and did a seminar on Getting Things Done. It’s called GTD. It’s like a philosophy.

Yes, I love GTD.

There are many things about Getting Things Done, but the thing that resonated with me the most, which I still don’t remember much of. I remember one thing, which is what is called the touch philosophy of email. I was being inundated right when this was 2004. Gmail had come out just then, so there was no need to delete emails. So I was just drowning in email then. I was up to my ears trying to figure out how to use email more effectively. I think if you can conquer email, everything else becomes easier. So, the philosophy I use is that when I open an email, I have to do one of three things. If I can process the email within less than five minutes, I reply to it right then and there, and it’s done. It’s out of my inbox.

The goal is to use the email inbox as a triaging room.

I archive it after that. Second, if it’s not something I have to do, I have to delegate it to someone or pass it on and just pass it on to them and archive it. So it’s their responsibility now. It’s gone from my mind, from my brain. Third, if it is on my project or to-do list, I have a separate note in Apple notes on my phone. I’ll just add it to my list of projects and archive it again. So, the goal is to use the email inbox as a triaging room. So you triage emails just like when you go to a hospital; they don’t operate on you in the waiting room.

The waiting room is a triaging place where they shunt you off to different places based on your ailment. The email inbox is a triaging room where, at least for me, I can’t deal with 50, forget 5000, or even 50 emails in my inbox. I get very anxious; I need to clear it all out and have a separate place on my phone, which is a list of projects I’m working on. Then, I use a calendar. So basically, I will say, “Okay, I have to prepare for this thing. I have to do this memo. I will block off time on my calendar,” and estimate how long it will take to do a first draft. I typically believe in a two-draft process for anything.

Most of my stuff involves writing memos or presentations. Unfortunately, we are all information workers. I think, at some point, much of what I do will be automated, and thankfully, now we have these AI agents, which make it much easier to sketch and out. In either case, it’s writing content of different kinds to perform, influence people and whatever the case may be, or make a case for something. But it’s time blocking on the calendar, his GTD and his Apple notes are my project management tools. That’s it.

Nothing is more complex. And there’s anything else? Simplicity, for me, is the key.

Yeah, I love GTD. I discovered it probably in the late 90s, which changed my life.

What facet of that is that? I don’t even know what GTD is. I just know this one thing. There must be other things with GTD besides this email thing.

In software development, a pre-mortem involves identifying potential issues before launch and creating mitigation plans for each, which empowers teams to anticipate and address problems proactively. Share on X

Oh my goodness, that’s so huge. Yes. The creator of GTD is David Allen, who wrote the book Getting Things Done, which sold millions of copies. It’s got a whole system, for example. Everything that is more than one action is a project. So, you have a project list and a list of the next actions. Then there’s also someday maybe where you park stuff that you won’t keep looking at over and over again. Maybe once a week, you review your projects list, and someday maybe, but you’re working off your next actions.

If let’s say, you’re going to buy a car, you don’t have to figure out all the things involved in buying a car. You just need to figure out what the next action is. Is it to send an email to the dealership? Is it to do some research on different car models? Is it to go in for a test drive? You don’t have to map everything out. Just find out what the next action is. Make sure it’s one action and not like a mini project. That goes on your next action list. And then you assign it a context. Is that an errand, or is that something that my phone is like a phone call? Or is it an email? Is it something that I do at home or the office? And so you can sort or filter by context and say, “Well, I’m sitting in the doctor’s office waiting for my appointment.”

I can do stuff involving my phone, but I can’t do stuff requiring me to be on an errand at home or the office. So, I don’t want to see any of those items in my filter set. So just show me, for example, phone calls I can make. You can also filter by project or by area of focus. An area of focus is ongoing. Not a final project comes to completion; you have a finish line, and you’re done. It’s closed. But an area of focus, like being a father or a husband, is ongoing, right? So you don’t want to treat it like a project.

Your brain is meant to be a factory, not a warehouse.

It’s an area of focus. So there I’m just scratching the surface of this whole methodology, but it’s been life-changing. It turns your brain from a warehouse of trying to remember all the things you need to do and all the little nuggets of wisdom and knowledge that you’ve picked up to have a trusted system where all that goes into importance, that that word trusted. You need to underline that because if you don’t trust it, you use your brain as the warehouse instead. Once you switch from your brain being the warehouse to that GTD-based system, your brain can be a factory, which is what it’s meant to be for inventing, creating, and innovating. Your brain is meant to be a factory, not a warehouse. That’s one of the primary philosophies of GTD.

I love that. I didn’t know some of these details. I forgot these details I just used. That’s the thing. It’s an expansive program, and so you can, I think, pick and choose the things that work for you basically right out of that.

So that’s good. I have my email organized based on GTD. So I have an action folder, a read review folder, a someday maybe folder, and archives. And then my assistant will go into my inbox, keep it at inbox zero. So, every day, there’s only stuff in the inbox from that day until she goes in and files as she goes in multiple times a day to file stuff. And I try to stay out of my inbox. It’s tempting, but I try to stay out of the inbox and just go straight to the action folder and only focus on that.

Then, once in a while, once every day or two, I’ll go into the read review folder, which is where this CC-type stuff is. I just need it. FYI, I don’t need to action anything, and that’s been a game changer for me. I can’t imagine maintaining my email inbox anymore. I haven’t done that for ages. That’s a poor use of time for pretty much everybody.

Amazing. I had no idea I was talking to a GTD maestro there.

Giving people permission, encouraging them to talk about the things that could go wrong ahead of time, and formulating a plan for each of them is a very powerful exercise.

I went to his workshops. I’ve had him on this podcast. I’ve had him on twice. Another thing that I just love that he didn’t write up in the book, but he told me in one of the interviews that we did is if you have an overwhelming amount of information, let’s say, in your inbox, let’s say you’ve allowed it to accumulate to thousands of emails. Instead of trying to cut that down, you create a new folder called DMZ demilitarized zone, drop all those emails into that folder, and start fresh with an inbox zero. And you maintain your email hygiene from there, not trying to go back and worry about everything that’s been sitting there for 6,8, or 10 months. That’s helpful. DMZ Folder.

I like the DMZ. I like that.

Yeah. And that can apply to any aspect of your life where you’ve gotten out of control with papers, with files, with to-dos, anything, say, all right, instead of declaring to-do list bankruptcy or burning all my files, let’s just put it all in the DMZ folder and start fresh. And I’m going to have better hygiene from here. So, let’s talk a bit about Agile, Lean, the stand-up meetings, and all the more programmer-focused stuff. But a marketer may not be familiar with what would be some of the best strategies and systems and ideas and ways of being that, you know, from the programming world, managing programming teams and so forth, that would be ideal or at least somewhat beneficial for a marketer to know about, maybe implement.

I think one of the most interesting ones is the notion of post-mortems and pre-mortems. 

In software development, a pre-mortem is before you launch something; you try to say what could go wrong here. So everyone lists all the things that could go wrong ahead of time, and then you’re like, “Okay, do we have a mitigation plan for each of them?” That’s a good strategy for almost any function because we often optimize for the happy case or path: all things go right. But I think giving permission to people, encouraging them to talk about the things that could go wrong ahead of time, and formulating a plan for each of them is a very powerful exercise. So that’s the pre-mortem. 

The second thing is a post-mortem, recording that and having an action plan. You see, pre-mortem will surface many things and risks and come up with a plan ahead of the launch to fix them. Post-mortem is the opposite, which is after something happens. 

Engineering teams continuously practice post-mortem discipline. I think many functions need to improve in this area. Once you have a launch, whatever the case is, once you start, kick out the project, and a few weeks later, you need to have a post-mortem, a retro, as they call it.

Retros are very common in engineering. What is a retro, and do retros happen even if there’s no launch? How did the last few weeks go? What is working? What’s not working, and what could we do better, essentially, and continuing to keep being intellectually honest with yourself so that you can keep improving is important. I think that’s the thing that I think engineers, if there’s one thing they’re good at, is being completely, brutally honest, maybe in an apolitical way, and it drops people off the wrong way, but you’ll get the unvalued truth, for the most part, from engineers.

Yeah, I like that. I don’t think that my company does enough pre and post-mortems. Even if a client leaves, let’s say they’re having financial issues, and it’s not our performance, but they still left anyway. Maybe they laid off some of their marketing department and stopped working with other vendors, and we just moved on. It’s like we have to replace that client with another one. This happened not too long ago, and it was a big client. We didn’t do a post-mortem. We didn’t analyze what worked, what didn’t, and what we would do differently next time. How could we have helped them more meaningfully as they were, as the wheels were starting to go off the bus for them financially? When did we learn about it? How did we react or respond? You know, these are good questions.

A lot of the post-mortem is to uncover root causes or process issues, things that we can fix for next time. That’s the key thing of post-mortem. What will we take away that we can use for the next client, incident, event, and launch? That’s the key thing to improve. That’s how you continue to improve your process. As a definition of insanity, you are doing the same thing again and again and expecting different results. So, how do we avoid becoming insane and fix our process? And the post-mortem provides a way for us to. Again, I think the key is avoiding blame. You’ll see the post-mortem, there’s simply a doc that is maintained, and there’s a person who’s, like, taking notes, and then everyone is just, you know, what went well. Everything, even the worst situation, would have gone well.

A lot of the post-mortem is to uncover root causes or process issues that we can fix for next time.

What didn’t go well? It’s not even the person. It’s what didn’t go well. It’s not about the person. It’s about the what versus the who. What didn’t go well, and how can you fix it? What are the implications going forward? Very simple.

Yep. So, what would be an example of a root cause that you could ferret out from doing post-mortems and make a change in one of the companies you helped lead? Something may be relevant to our listeners.

I think one was at one of the companies I advised, where we spent a tremendous amount of money. I think the company came across a marketing tool or an ad platform that promised very low-cost app downloads. So they had a consumer app, or was it a B2B? It was a prosumer app. And so they wanted to. They were growing, but they wanted to go up in terms of getting their scale. This was a few years ago. This is in the mid-20s.

It was 2017 or 2018. They were unable to increase their app downloads themselves. They had a viral channel going, but it wasn’t growing that fast. It was growing, and retention was strong. So, they wanted to scale the acquisition. So they came across this company that promised very fast growth in app downloads. And so they basically said, “Okay, let’s try it.”

So they gave a $10,000 budget. Turns out it increased their app downloads by, I think they got 50,000 app downloads. So, twenty cents per app download. And it seemed that some percent of these people were converting. So the payback period, et cetera, seemed good. So then they went to, I think, 100,000 from there. And that was a big part of the marketing budget. Unfortunately, even though it got 500,000 app downloads, the download-to-conversion-to-customer ratio was extremely low.

And so I think in the pool, I remember very well we did a post-mortem. We were like, “How did we go wrong? We did start small with 10,000. What did we do here that was wrong? Why did we blow up this entire budget?” I think we realized that this company was actually a scam artist, where they would basically, for the first small budget, they would get you good customers and good traffic, but then as you scale, they would figure out they would just get you crappy traffic. Then, you had no recourse at that point. So what the company should have done is for any new channel, we ask them for two or three customer references, and we talk to them to understand how it worked for them at scale before we ever engage with any new channels. So I think we just didn’t do that. And that was bad diligence. So I think that from now on, it will become part of the playbook for any new channel, any new vendor of any kind across the company, or any third party we have helped with. Got to get a reference check.

Sometimes, the best lessons are the most painful.

It will not be approved. The budget will not be approved before you think of a reference check into a reference check.

Yeah, that’s great. It’s a good lesson—expensive, but a good lesson.

Painful, but good lessons. Sometimes, the best lessons are the most painful.

Yeah. How many companies do you advise? Currently?

Very few, I think. I’m an investor. With investment comes advising by automatism by default, but pure advising. It’s tailed off over the years. I think maybe half a dozen. It’s mostly investing. I invest in a lot of companies.

Maybe I’ve invested in it. Once you’re investing around the cap table until the company has a liquidity event, dies, or continues running, you’re on the cap table. So, there are probably hundreds of companies. I mean, more than 200. It could be 300 or so.

Wow, you have invested in 300 companies.

Yep.

My goodness. I don’t think I know anybody else who’s invested in that many companies. That’s awesome.

So, if you do something, think about how many clients you’ve helped, right? If you do something over 17 years, 300 is not that much. It’s only like 10 or 15 a year or something like that.

15 or 17 a year.

I think that’s pretty impressive. So, let’s go back to this idea of applying programming and agile-type systems to marketing. How about stand-up meetings? How about weekly sprints? What sort of recommendations do you have around these sorts of approaches?

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I used to run these things many years ago. Over the last 10 or 15 years, I’ve been more than one level above these sprints. I think they have evolved around how to use them, especially in COVID. People realize that having everyone in person, I mean, literally back then, used to stand around a table when everything was in person, right? Then, it became remote, and people realized that a weekly meeting was as important as a checkpoint. That said, people also realized that if you’re just going around and talking about what you did, what is the impact of that meeting? So, I think people have started focusing more on problems that people want solved versus just a status report. I think it’s just a status report. Everyone comes together for five minutes, gives a status report, and goes off.

Times when your status report could just be given over email or some other Slack channel. So I think some of these weekly things have become more around only raising problems that are blocking you from accomplishing your goal. Versus like the only people who should raise their hand are people who are not on track to hit their weekly or monthly goals and ask for help. And then, everyone jumps in to figure out how to help them and takes action to help them. It’s like everyone’s just giving a status report.

I feel it’s the same thing for meetings broadly. I think we all realized during COVID, and many companies declared meeting bankruptcy where they’re like, “Look, there are too many meetings with the calendar.’ Shopify did this famously by removing all meetings, everyone’s calendars, and any meeting above.

Unless there’s a clear reason, the meeting should not exist and should be conducted asynchronously over Slack or email.

Companies have said that in any meeting about two people, you’ve got to do one-on-one, you should meet your colleagues, one-on-one aiming or two people, you’ve got to have a very high bar to set up a meeting because it’s just a multiplicative waste of time for most meetings, especially status updates. So, my take on most things is that unless there’s a clear reason, the meeting shouldn’t exist and should be done asynchronously over Slack or email. You should only have a meeting if you’re trying to make a decision, solve a problem, unblock someone, or make progress. But most things should happen asynchronously.

Yeah, I remember hearing about or reading about Jeff Bezos. Maybe it was Elon Musk who would go into a meeting, and if there was no agenda, he would cancel the meeting. It didn’t matter how many people were in it; if there was no agenda, he’d leave immediately and cancel the meeting. So they couldn’t keep meeting without him. The meeting’s over.

I couldn’t agree more with that philosophy, which should be the case. Whatever decision you take, whoever the meeting person calls the meeting, they better have done pre-work and typically have a document or something sent ahead of time so that people can come and not spend. You still might want to spend five minutes reviewing the document, but if it’s a long document, it needs to be short. No one has the patience to read long documents. However, meeting pre-reading is also very important to make these meetings efficient and not waste people’s time.

Yeah. So, what does pre-work look like besides an agenda? What are some of the pre-work items that you would expect before a meeting?

It depends on the meeting type. For example, if it’s a decision, you must ideally follow a framework. I think I created a decision framework called S.P.A.D.E. at the Square, along with a few people. And that decision framework, S.P.A.D.E., is now used by many Silicon Valley companies.  It’s only to be used for important decisions that are one-way door decisions, another term that Bezos coined, where they are irreversible in some way. Once you make it, it’s like changing the company or pricing or something. It’s just hard to reverse it. It’s very painful to reverse it, almost irreversible.

And so I think for those, you need a lot of thought and to consider alternatives. You need to have the right person making the decision. You need to have the right people. They consult, and you need to understand each alternative, how it compares against the other, and what you’re optimizing for, first and foremost. So there’s this framework that says, that kind of walks you through pulling it all together. And there’s a lot of, I mean, there’s some overhead dealer, it can take a few days to even a few weeks sometimes if it’s a pretty complex decision. You put that together, and there are multiple rounds of discussions with the people you consult in fleshing out the pros and cons of each alternative in evaluating it, sometimes even quantitatively, against the objective function you want to optimize for. You pull it all together, and then at the end, you come to a decision meeting where you talk through it. I think there are various ways of voting on this.

I believe in private voting on decisions so that you’re not going around the room and saying, “What do you think of all these choices?” Because if you, I’m sure you’ve been in meetings where the first person, what they say and anchor, there’s an instant anchoring effect on everyone else, and everyone looks to see what their peer or manager is saying. It’s much harder to go against a person in power who is saying, as I say, HiPPO. HiPPO is the highest-paid person in the room. I think having the consulted people give their feedback or the option they prefer with their ethics to the person in private, by email, Slack, or whatever the case may be, or even in person. Then, you call a decision meeting at the end. The person making a decision gets all their input, feedback, and choices, and tells everyone, here’s a decision I made, here’s why. Then, everyone has to disagree and commit. It means that even though you disagree with the meeting, you have to commit to implementing and following through with the decision.

That’s an important characteristic of great companies, for great teams, where it’s not about the decision that matters, but the quality of decision-making. Everyone’s voices need to be heard, and the right process needs to be followed. Once the decision is made, you’ve got to disagree, and you can’t undermine it because a decision needs everyone’s support to be implemented.

Yeah, that makes a lot of sense. If you don’t do it, it sounds like that would be a pretty big source of dysfunction in the organization. Is there a name for this whole framework that you’ve been describing?

Yes, it’s called S.P.A.D.E. S stands for setting, P stands for people, A stands for alternatives, D stands for decision, and E stands for explain because the explanation phase turns out to be the most important. Turns out one of the biggest sources of company discontent is that people don’t understand how decisions are made. The S.P.A.D.E. framework came over because, at the Square and on all hands, we had done an employee survey in 2014 or 2015 that revealed that one of the highest negative feedback scores from employees was people felt decision-making was not transparent. It was unclear who was making decisions, why they were making them, and how they thought about it. So, I was assigned to create a decision-making framework, which led to S.P.A.D.E. So, if you search for my name and S.P.A.D.E., you’ll find it.

You need to have the right person making the decision.

I found a nice article you wrote on Coda.io about the framework. It’s really good stuff. There’s a great story about how you helped Larry, Sergey, and Eric with difficult problems using your framework. So what would be the things that our listener needs to know or do to prepare for the big shakeup that’s coming because of AI? With most jobs becoming redundant or unnecessary or automated, including creative jobs, what should our listener do to skate to where the puck will use a Wayne Gretzky quote?

Become a power user of AI tools in your profession, stay on top of AI tools, and become a user. Because I think if you’re offering a service, the future will not be pure AI. It’s going to be a hybrid human in AI. I think AI-enabled services can help you scale your business massively. I think the future of a consulting firm is not pure. It’s. Basically, I think nowadays, people have been saying it’s a one-person, billion-dollar company, right? I think that’s still a far fetch. But it showed that earlier, you might need a team to do stuff, but now you can significantly scale yourself as a solopreneur and an entrepreneur using AI. If you think of AI as an assistant, it can help you serve your clients much better.

I will repeat the same thing I said earlier. You can’t be afraid of it. I think even though every industrial revolution or revolution has basically, maybe in some cases, eliminated jobs, it’s also created new jobs of different kinds. So we need to understand these tools, use them, become parties of the tools, and understand how we can be part of the go-forward thing, which I think will be a hybrid human and AI future, not a pure AI feature. Not a pure human future.

Yeah, hope so. So, what sort of new jobs do you envision being created or in the process of being created now?

I think it’s the same job as always. I think new jobs itself. I do think training these AI models is going to be very interesting. I think that for maybe the next few years, conversing with these AI models and using them, which used to be called prompt engineering but probably might be called AI fine-tuning or something, might become a very interesting job. What do you think about SEO? You are the number one person in the world. That itself is going to evolve, right? If you think about it, SEO is never going to be dead. It is just going to evolve.

Having quality decision-making is an important characteristic of great companies.

So, I think just being a lawyer will never be dead. It’s going to evolve. So, every job we have today that serves a fundamental human or business need will evolve. Being a hairdresser is going to evolve. Everything is going to evolve. So, we just need to be part of the evolution?

Yeah, absolutely. So, what have we not spoken about that you would like to share, like a wisdom nugget, before we close out the episode? Something that maybe would be universally applicable to everybody, but we haven’t discussed it so far.

One of my core beliefs is belief in helping others without any expectation of reward in the near term. I believe in the notion of karma and the fact that everything evens out in some way over long periods of time. So I think it’s very important to note, be very calculated in, oh, if someone asks you for help, what do I get out of it? Do not do that calculation if it’s easy enough. Now, if you have to go out of your way, and it’s inconvenient and hard for you to do, that’s different. But if it’s easy, especially in the information age, a lot of help is just writing an email or tweeting something in favor of someone you believe in or are doing something. Those are easy things to do. And I do think, I mean, I’ve written so many letters of recommendation to people.

I know them reasonably well, but they’ve just approached me, and it took me five minutes or ten minutes of my time to just send a note to someone or help them differently or connect them with someone. It’s just humanity. And turns out, and who knows if it’s true or not? But I attribute something good that happens to me, especially something good I did for someone a few years, months ago, or days ago, who knows? But that’s my belief, and I think it also makes you feel good about yourself, to be honest. I think it’s a great way to feel. I’ve seen studies of people reporting feeling good about themselves after they do something good for someone else. So I do believe just helping someone, if someone asks for your help, if it’s not that hard if it doesn’t put you out in a big way, is one of the best ways to feel good about yourself, which is selfish in some ways, but also have good things happen to you in the future.

Yeah. Do you have a story to share, a personal story of karma, and how did that show up in your life?

Yeah. I advised the company. I helped this company after Google, a colleague with whom I worked. I just helped them a few times. And it turns out, they referred one of my best-ever angel investments to me. Two or three years later, I had forgotten about them, and then they suddenly ping me, saying, “Hey, this is an entrepreneur you should meet, and this is one of the best companies.” It was incredible for me in many ways, and I just made several calls with them. I enjoyed that.

Running your business is not about what the decision is but the quality of decision-making. Everyone's voices need to be heard, and the right process needs to be followed. Share on X

I learned from that call. And they thought so highly of the help I provided that they remembered it. And several years later, I was like, “Oh, yeah, sure.” That company introduced me to this amazing entrepreneur that I had invested in, and that was one of the best angel investments I’ve ever made.

That’s cool. All right, well, that’s a great way to end this.

Stephan, you are the same way. You help so many people. I’m sure you. I’m curious: Do you have a story like this to share? I’m sure you helped so many people. I’m curious because this has happened to you.

Yeah. It’s how I live my life. So I heard from somebody years later that I helped, introduced somebody to, or whatever. The thing is that it’s important not to claim credit for creating that opportunity or making that introduction or whatever. We’re just agents for God. We’re just delivery agents or pizza delivery people for God’s miracles. For example, I’ve had multiple couples working in my organization who started as singles and ended up getting married. For a while there, I thought, “Wow, I’ve created a company where I’ve helped some families get started; that’s pretty cool.”

One of my core beliefs is belief in helping others without any expectation of reward in the near term.

I realized afterward, maybe years, there’s nothing for me to claim credit for. That was written in the stars. That was meant to be. That was destiny for those souls to come together and become soul mates. I was gifted the blessing of being able to facilitate that, but it was destiny. Because of my good karma, I was given the role of bringing them together or helping facilitate them.

Amazing. You’ve always been so gracious when asked, “Can you work with this company?” You do a call, and that just permeates how you live your life. So thank you for that.

Yeah, of course. Well, I feel like we’re all a soul family. As Ram Dass famously said, we’re all just walking each other home.

I love that saying.

All right, so if our listener wants to learn more from you, follow you on social platforms, and all that sort of stuff, where do we send them?

It’s Twitter. It’s probably the best place. It’s @gokulr on Twitter. So, if you just search for my first name or last name, you’ll find me. Just search for me on Google, and you’ll find it. Thanks to the great SEO work that Stephan has done and helped me think about, it’s up there.

Awesome. Gokul, I want to say publicly how much I appreciate you. You’ve been a wonderful support to me personally over the many years. You’ve given me book blurbs or testimonial praise quotes to go on the front matter of multiple editions of my books. You’re very supportive of me, and I really appreciate you.

Thank you. It’s been a pleasure working with you and knowing you, and I’m excited for our partnership to continue over the next few decades and beyond. 

Amen. All right, well, Gokul, listener, thank you. It’s just a beautiful life. So make it even more beautiful by doing something unexpected and wonderful for somebody you care about. And we’ll catch you on the next episode. I’m your host, Stephan Spencer, signing off.

 

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Your Checklist of Actions to Take

Stay on top of new AI tools and learn to use them effectively. Explore new AI tools and experiment with how they can augment my work.

Identify potential risks and failure points that could lead to failure before launching a project and develop mitigation plans and contingencies for each identified risk factor.

Schedule a dedicated meeting to review the project objectively after completion to discuss what processes/decisions worked well and which didn’t.

Follow a framework like SPADE for making important, irreversible decisions. The SPADE framework guides me through: Setting objectives, identifying People to consult, listing out Alternatives, making the Decision, and Explaining the rationale.

Encourage open feedback by having people vote privately on decisions, minimizing anchoring bias.

Embrace the “disagree and commit” philosophy – commit to executing a decision, even if I disagree with it.

Make meetings productive by having a clear agenda, requiring pre-work, and only meeting to solve problems or make decisions.

Take an effort to lend a hand or provide value when others ask for assistance. Small acts of generosity can compound into large positive impacts over time.

Be willing to evolve processes, admit mistakes, and change course when needed. View shortcomings not as failures but as opportunities to learn and enhance capabilities.

Learn more from the tech titan Gokul Rajaram. Explore his S.P.A.D.E toolkit and follow him on X at @gokulr.

About Gokul Rajaram

Gokul Rajaram serves on the executive team at DoorDash, the premium food ordering service, where he is currently the Corporate Development and Strategy Lead. Prior to DoorDash, he worked at Block as a Product Engineering Lead, where he led several product development teams and served on Block’s executive team. Prior to Block, he served as Product Director of Ads at Facebook, where he helped Facebook transition its advertising business to become mobile-first. Earlier in his career, Gokul served as a Product Management Director for Google AdSense, where he helped launch the product and grow it into a substantial portion of Google’s business. Gokul is also on the board of The Trade Desk and Coinbase. He’s an avid investor, having bet on literally hundreds of startups!

Gokul holds a bachelor’s degree in Computer Science Engineering from the Indian Institute of Technology, Kanpur, where he received the President’s Gold Medal for being class valedictorian. He also holds an M.B.A. from The Massachusetts Institute of Technology and a Master of Computer Science from the University of Texas at Austin, where he received the MCD University.