Nov 11, 2024
Why Google's Product Leader Left Billions for 100 Users
An interview with Jacob Bank, Founder of Relay.app
Founder Focused
The conventional wisdom tells young professionals to aim for Big Tech. Google, Meta, Apple—these are the dream destinations that promise prestige, compensation, and career acceleration. But what if this one-size-fits-all advice is actually limiting your growth?
Jacob Bank knows both sides of this equation intimately. He spent six years as a product leader at Google, responsible for Gmail and Google Calendar with their billions of users. Yet he chose to leave that security to build Relay.app, a workflow automation startup that's still in its early stages. His perspective challenges the narrative that Big Tech is the ultimate career destination.
In this candid interview, Bank reveals why the skills that make you successful at a massive company can actually hurt you as a startup founder, how to strategically choose your career path based on what you want to learn, and why he feels more connected to 100 passionate users than 2 billion Gmail subscribers.
Watch the full interview now on EO's YouTube channel! Below is the complete transcription of the interview. Minor edits have been made for clarity and readability.
Key Highlights:
"Should you join a big company? Should you join a growth-stage startup? Should you join an early-stage startup, start your own company? And I don't believe there's one right answer to that."
"So if you really want to learn how to build a 0 to 1 product from scratch, don't go to Google. Go to an early-stage startup. If you want to learn how to hyperscale, go to a growth stage company. If you want to learn how to operate when you already have a billion users, go to Google."
"I would just encourage people to be very deliberate about when you take a job, what skills do you want to learn and in what way do you want to grow in that job, and make sure you've chosen a company that will best give you the opportunity to learn and grow."
"So if you really want to learn how to build a 0 to 1 product from scratch, don't go to Google. Go to an early-stage startup. If you want to learn how to hyperscale, go to a growth stage company. If you want to learn how to operate when you already have a billion users, go to Google."
"I would just encourage people to be very deliberate about when you take a job, what skills do you want to learn and in what way do you want to grow in that job, and make sure you've chosen a company that will best give you the opportunity to learn and grow."
From PhD Dropout to Google Acquisition
Can you tell us about your journey from Stanford's AI lab to founding Timeful?
Jacob Bank: So my name is Jacob Bank, and I'm currently the founder and CEO of Relay.app. Relay.app is a workflow automation tool that saves people time by automating the repetitive and mundane things they have to do every day, usually connecting one tool to another tool. So for example, let's say every time you get an email from a customer, you want to update a spreadsheet, you could use relay to automate that.
I was pursuing a PhD in the AI lab at Stanford when I ended up dropping out in 2013 to start my first company, Timeful, which was an AI powered digital calendar. Timeful ended up being acquired by Google in 2015, where I spent six years as a product leader, responsible for Gmail, Google Calendar, and a few other products, mostly in the area of productivity, and I left Google in 2021 to found Relay, and I've been doing that for the last 2.5 years.
I was pursuing a PhD in the AI lab at Stanford when I ended up dropping out in 2013 to start my first company, Timeful, which was an AI powered digital calendar. Timeful ended up being acquired by Google in 2015, where I spent six years as a product leader, responsible for Gmail, Google Calendar, and a few other products, mostly in the area of productivity, and I left Google in 2021 to found Relay, and I've been doing that for the last 2.5 years.
What drew you to AI initially, and how did that lead to entrepreneurship?
Jacob Bank: I got into AI first, I would say. I had a couple of amazing professors in my undergraduate education, all big in various aspects of AI whether it was computer vision or network analysis or kind of core machine learning algorithms. And that's how I developed sort of my initial skill set and understanding sort of like the basic AI technologies and capabilities at the time.
I actually really wanted to be a professor and really wanted to do academic research, but I just wasn't that good at it. But I was pretty good at the combination of AI software engineering, team building, product thinking, talking to customers, and then the project we were working on was an AI powered digital calendar, and it was way better suited to being a startup company and a product than to being an academic research project.
So even though this was not my plan at all in life, it was like, in fact, very, very jarring to make this change. It became immediately clear after one month of leaving Stanford to work on Timeful that it was the right choice, and I never looked back from there.
I actually really wanted to be a professor and really wanted to do academic research, but I just wasn't that good at it. But I was pretty good at the combination of AI software engineering, team building, product thinking, talking to customers, and then the project we were working on was an AI powered digital calendar, and it was way better suited to being a startup company and a product than to being an academic research project.
So even though this was not my plan at all in life, it was like, in fact, very, very jarring to make this change. It became immediately clear after one month of leaving Stanford to work on Timeful that it was the right choice, and I never looked back from there.
How quickly did things move from launch to acquisition?
Jacob Bank: We launched Timeful in July of 2014. We were featured in the App Store. We were kind of a hot product in the productivity space. There were a few other well-known email and calendar clients at the time. Accompli and Sunrise and Wonderlist ended up getting acquired by Microsoft. We got acquired by Google, so we ended up joining Google on May 4th, 2015.
Six Years Inside the Google Machine
What was your experience like transitioning from startup founder to Google product leader?
Jacob Bank: When I first joined Google, my primary role was to integrate the Timeful acquisition, and that meant working on a few features that were inspired by Timeful and that we could build into Google Calendar. So we worked on tasks in Google Calendar, we worked on a feature called goals in Google Calendar.
And then after that initial integration period, which was between 6 and 9 months, Google had to figure out, OK, what are we actually going to do with these people? And the most natural place to put me and to put the Timeful team would have been in Google Calendar, but we were all based in California and the Google Calendar team was based in Switzerland, but Google Calendar's partner team, Gmail was based here in California.
And so I and most of the other members of the Timeful team ended up shifting from working on smart features in Calendar to smart features in Gmail. And then after becoming responsible for Gmail as a whole, I became responsible for a broader set of products, which at one point included Calendar and our developer platform, Google Chat, and a few others.
And then after that initial integration period, which was between 6 and 9 months, Google had to figure out, OK, what are we actually going to do with these people? And the most natural place to put me and to put the Timeful team would have been in Google Calendar, but we were all based in California and the Google Calendar team was based in Switzerland, but Google Calendar's partner team, Gmail was based here in California.
And so I and most of the other members of the Timeful team ended up shifting from working on smart features in Calendar to smart features in Gmail. And then after becoming responsible for Gmail as a whole, I became responsible for a broader set of products, which at one point included Calendar and our developer platform, Google Chat, and a few others.
What was the biggest lesson you learned about operating at Google's scale?
Jacob Bank: One of the things I learned most at Google is how high the bar is to ship a piece of software when you have 2 billion users. And you have the level of scrutiny on you that Google has, and I think it's important to recognize that when you're Google, you have a lot of advantages in terms of data, in terms of hardware, in terms of algorithms, but you also have a lot of disadvantages in terms of press scrutiny, regulatory scrutiny, user scrutiny, internal dynamics, and bureaucracies.
And so it's, I can see why it's hard and I ran into many of those frictions myself. That's not to say that I think any of those limitations or areas of caution were the wrong approach. I think it's just a reality that comes from being at Google scale.
And so it's, I can see why it's hard and I ran into many of those frictions myself. That's not to say that I think any of those limitations or areas of caution were the wrong approach. I think it's just a reality that comes from being at Google scale.
Breaking Free from the Golden Handcuffs
After six successful years at Google, what motivated you to leave and start Relay?
Jacob Bank: So first, I left Google for two reasons. One was a personal reason, which is I wanted to learn and grow in a different way. I'd been 6 years at Google. I loved my time at Google, but by the end of my time at Google, I had kind of settled into a routine, and I wanted to push myself to learn and grow in new ways. And I knew from my previous experience that starting the company is the best way to push yourself to learn and grow new skills.
And the second was, I saw an opportunity and the opportunity was, and this is what led to relay, is that most of my time at Google, I worked on Gmail, on calendar, and I observed that in most of the productivity and collaboration ecosystem, people are really focused on building individual tools that are better. But what we saw in practice is that to actually get something done at a company or in your work, the cross-product workflows are often just as important as a within-product workflow.
So the workflow, for example, of like composing an email within Gmail may not be as important as getting that email into your CRM tool effectively. And I knew that to build a product that was really, really good at these cross-tool workflows, it would be hard to do it from within the context of an existing company where you're incentivized to work on the products that existing company already has.
And the second was, I saw an opportunity and the opportunity was, and this is what led to relay, is that most of my time at Google, I worked on Gmail, on calendar, and I observed that in most of the productivity and collaboration ecosystem, people are really focused on building individual tools that are better. But what we saw in practice is that to actually get something done at a company or in your work, the cross-product workflows are often just as important as a within-product workflow.
So the workflow, for example, of like composing an email within Gmail may not be as important as getting that email into your CRM tool effectively. And I knew that to build a product that was really, really good at these cross-tool workflows, it would be hard to do it from within the context of an existing company where you're incentivized to work on the products that existing company already has.
The Great Unlearning: Google Skills vs Startup Reality
What skills from Google transferred well to startup life, and what did you have to unlearn?
Jacob Bank: At Google, I built up an amazing talent network of incredible engineers, designers, and product people that I would love to work with again. I learned a lot about productivity tools in the market. I learned a lot about how to operate at scale. I also had to unlearn a bunch of stuff because at Google, there's this inertia, like, every day there will be lots of new users signing up for Gmail, and your job is to take those new users who already know Gmail, already have some expectation over it, and just make them happy and successful.
And that is totally different from trying to create something totally new that no one has heard of, that no one is gonna sign up for unless you get them to sign up for it. And so many of the things I learned at Google were about how to take this flood of revenue, this flood of users, this flood of interest and feature requests and support tickets and figure out how to redirect them in the most appropriate way.
Like at Google, you learn a lot about how to redirect this flowing river, whereas at relay, there's no river. Like when you start a company, there's no river. You have to figure out like, how do I make the first little drops of water come out of the spring. And it turns out those skills are totally different.
And that is totally different from trying to create something totally new that no one has heard of, that no one is gonna sign up for unless you get them to sign up for it. And so many of the things I learned at Google were about how to take this flood of revenue, this flood of users, this flood of interest and feature requests and support tickets and figure out how to redirect them in the most appropriate way.
Like at Google, you learn a lot about how to redirect this flowing river, whereas at relay, there's no river. Like when you start a company, there's no river. You have to figure out like, how do I make the first little drops of water come out of the spring. And it turns out those skills are totally different.
How does the relationship with users differ between Google scale and startup scale?
Jacob Bank: So, Google, you know, Gmail, I think has something like 2 billion monthly active users. So at Google, I feel like this sort of societal impact—I'm working on this thing that's really, really important to lots and lots of people, but I don't know any of those people individually.
Whereas at Relay, our first 100 users who really love the product, I know their name, I know their business, I know what they're trying to achieve. I know why they love relay and how it helps them. And so I almost feel more connected to the 100 really, really passionate Relay users than I feel to the 2 billion Gmail users because it becomes so much more personal and intense. And that's something I love about the early-stage startup. People are not just numbers on a dashboard, but they're real humans trying to get something done that you're helping.
Whereas at Relay, our first 100 users who really love the product, I know their name, I know their business, I know what they're trying to achieve. I know why they love relay and how it helps them. And so I almost feel more connected to the 100 really, really passionate Relay users than I feel to the 2 billion Gmail users because it becomes so much more personal and intense. And that's something I love about the early-stage startup. People are not just numbers on a dashboard, but they're real humans trying to get something done that you're helping.
The Strategic Career Path Framework
What's your advice for people trying to decide between big tech, startups, or starting their own company?
Jacob Bank: The big difference between a startup and a big company is that it's way easier to make a decision, change a decision, and then adapt flexibly, because at Google, once you've marshaled teams of hundreds of people and they're all pointed in one direction, it can be really hard to change those directions because there's so much inertia. That's why you have to plan really, really carefully, and then once you're on a path, you kind of have to keep going.
Whereas in a startup, there's a few people, everyone's very nimble, there's no inertia, and you can immediately change your mind to do anything, and that creates positives, but also some negatives. So the positive is you can be totally intellectually honest. When you see something's not working, you don't have to pretend that it's working and just keep going according to plan, you change your mind and you adapt to the new information, and so that's the huge advantage of a startup, and that's the reason why startups often take new markets.
So if someone wants to start a company, spending time at a big company is valuable in other ways, but you'll have to unlearn just as many of the skills you learned at a company like Google to be a successful startup founder as you can take advantage of the skills that you did learn at Google.
Whereas in a startup, there's a few people, everyone's very nimble, there's no inertia, and you can immediately change your mind to do anything, and that creates positives, but also some negatives. So the positive is you can be totally intellectually honest. When you see something's not working, you don't have to pretend that it's working and just keep going according to plan, you change your mind and you adapt to the new information, and so that's the huge advantage of a startup, and that's the reason why startups often take new markets.
So if someone wants to start a company, spending time at a big company is valuable in other ways, but you'll have to unlearn just as many of the skills you learned at a company like Google to be a successful startup founder as you can take advantage of the skills that you did learn at Google.
How should people think strategically about their career choices?
Jacob Bank: And another thing that people talk about a lot is like, should you join a big company? Should you join a growth-stage startup? Should you join an early-stage startup? Should you start your own company? And I don't believe there's one right answer to that.
So if you really want to learn how to build a 0 to 1 product from scratch, don't go to Google. Go to an early-stage startup. If you want to learn how to hyperscale a product, go to a growth stage company. If you want to learn how to operate when you already have a billion users, go to Google. If you want to develop a talent network, you maybe go to a slightly larger company that gives you more people you can interact with. If you want to build a peer founder network, probably start your own company because then you'll be in touch with many other founders just naturally.
I would just encourage people to be very deliberate about when you take a job, what skills do you want to learn and in what way do you want to grow in that job, and make sure you've chosen a company that will best give you the opportunity to learn and grow in that way.
So if you really want to learn how to build a 0 to 1 product from scratch, don't go to Google. Go to an early-stage startup. If you want to learn how to hyperscale a product, go to a growth stage company. If you want to learn how to operate when you already have a billion users, go to Google. If you want to develop a talent network, you maybe go to a slightly larger company that gives you more people you can interact with. If you want to build a peer founder network, probably start your own company because then you'll be in touch with many other founders just naturally.
I would just encourage people to be very deliberate about when you take a job, what skills do you want to learn and in what way do you want to grow in that job, and make sure you've chosen a company that will best give you the opportunity to learn and grow in that way.
Building Relay: From Experiments to Traction
How did you find the right product-market fit with Relay after leaving Google?
Jacob Bank: So over the first year of relay, we built 5 or 6 different product experiments, all using AI and somehow, in some way to connect a workflow across them. And then it was only after a year of all these experiments that the real opportunity sort of crystallized in front of us.
Most of those repeated things at work involve multiple tools and multiple people, and most of those repeated things at work involve some things that can be automated and some things that we need to do ourselves with judgment and with intuition and with creativity. And so that's what led to the final idea of relay, which is like, we're going to build a workflow tool that helps you save time on things you do over and over again by automating the parts that can be automated and make it easier for people to do the rest.
Most of those repeated things at work involve multiple tools and multiple people, and most of those repeated things at work involve some things that can be automated and some things that we need to do ourselves with judgment and with intuition and with creativity. And so that's what led to the final idea of relay, which is like, we're going to build a workflow tool that helps you save time on things you do over and over again by automating the parts that can be automated and make it easier for people to do the rest.
Where does Relay stand today in terms of traction?
Jacob Bank: We have initial traction in the sense that there's a few different definitions, like, there's the Y Combinator definition of do you have 10 people or 100 people that love your product? We have that. There is another definition I like from Jason Lemkin of Saster, which is: Do you have 10 unaffiliated customers? Meaning 10 people you've never met before, you have no idea how they found you, they just found you and they're paying for your product. We have that too.
So we have the people who love us, we have customers coming and finding us through the ether and signing up self-serve and paying us money. We have a product that's growing week over week and revenue that's growing week over week. So every Monday we get a metrics report and we have more users and more revenue and more usage than we had the week before. Those are all the things that are good.
So we have the people who love us, we have customers coming and finding us through the ether and signing up self-serve and paying us money. We have a product that's growing week over week and revenue that's growing week over week. So every Monday we get a metrics report and we have more users and more revenue and more usage than we had the week before. Those are all the things that are good.
The Reality of Startup Challenges
What keeps you motivated through the inevitable startup challenges?
Jacob Bank: I think it's already way easier to start a company now than it was 10 years ago, even ignoring AI, the tooling is way better. And so like, back in the olden days, if you had to incorporate, you'd have to like figure out what state to incorporate in and figure out how to write all the legal documents and engage a law firm, and now you have clerking and stripe Atlas. And in the olden days, you'd have to figure out, well, how am I gonna get health insurance for all my employees as a startup and I have to go to all these brokers, and now you just sign up for Gusto or Rippling.
So there's a bunch of things that have happened to make it easier to create startups that allow you to do more with a smaller team. You can very quickly scale up resource that you need. And so, what keeps me motivated, two things. One is the mission and vision of what I think we can create. I think we can create something really, really cool that's also going to be a successful business. And the other thing keeping me going is that each thing that's hard that we go through teaches me some new skill that I wouldn't have gained any other way.
So there's a bunch of things that have happened to make it easier to create startups that allow you to do more with a smaller team. You can very quickly scale up resource that you need. And so, what keeps me motivated, two things. One is the mission and vision of what I think we can create. I think we can create something really, really cool that's also going to be a successful business. And the other thing keeping me going is that each thing that's hard that we go through teaches me some new skill that I wouldn't have gained any other way.
What are the biggest existential challenges facing Relay?
Jacob Bank: So what's hard about starting a company? You have to convince people to work with you. You have to convince someone potentially to give you money, either customers or investors. You have to figure out what problem to solve, figure out what product to build, figure out if that product can even be built, figure out if that product actually solves the user's problem. Figure out how you're going to find anyone who cares that you've solved this problem. Figure out how you're going to get customers at scale, trying to figure out, you know, how some employment regulation in France is going to affect one of your employees.
Like there's no shortage of challenges and every day different challenge. I think the existential ones are, are you solving a real problem? Has your product actually solved that problem, and can you figure out a way to scalably get more users who have that problem to try your product? Those are like the big three challenges that underlie all of it.
Like there's no shortage of challenges and every day different challenge. I think the existential ones are, are you solving a real problem? Has your product actually solved that problem, and can you figure out a way to scalably get more users who have that problem to try your product? Those are like the big three challenges that underlie all of it.
How do you think about burnout and staying motivated through the grind?
Jacob Bank: But even on the way to solving those big 3 challenges, there are a whole bunch of related difficult things, whether it's in hiring or finance or marketing or sales that you have to learn along the way. And so I think, it's definitely hard, but one thing that gives me comfort is it's kind of related to the topic of burnout, which is people talk about a lot about burnout these days.
And for me at least, I don't really think for other people either burnout is a function of how many hours you work. Burnout is a feature of, are you making progress? There's nothing more demoralizing than working for 50 hours on something and then not having it go anywhere, that can burn you out pretty fast. But if you work really hard on something and a customer loves it and the business is doing well, I've never actually seen anyone get burnt out by that. I've only seen people get more motivated and more excited by that.
And so that's kind of similar to how I think about the challenges in a startup, like, challenges really get you down if you don't solve them. But as soon as you solve that one, you know, as soon as you solve each incremental problem, it gives you so much more energy and motivation to solve the next one.
And for me at least, I don't really think for other people either burnout is a function of how many hours you work. Burnout is a feature of, are you making progress? There's nothing more demoralizing than working for 50 hours on something and then not having it go anywhere, that can burn you out pretty fast. But if you work really hard on something and a customer loves it and the business is doing well, I've never actually seen anyone get burnt out by that. I've only seen people get more motivated and more excited by that.
And so that's kind of similar to how I think about the challenges in a startup, like, challenges really get you down if you don't solve them. But as soon as you solve that one, you know, as soon as you solve each incremental problem, it gives you so much more energy and motivation to solve the next one.
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