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| | HOUSEKEEPING 📨 | My goal of becoming the Internet’s strongest startup founder hit a bit of a snag recently. After snatched another 10 year best (102kg), I hurt both my knees on the same lift, and have been walking around like an old man since. Truth be told, training 2 hours per day, at 39 years young is going to catch up with you at some point. And that some point is now. But I’ll be back. At the moment, it’s light training, and lots of park walks with Ziggy. Not too bad really. | Also, I had a reader reach out after my last edition to let me know that my reference to assumed Chinese spying could foster increased Sinophobia (anti-Chinese sentiment aka racism). I had to Google the term to be honest, but after looking back on the piece and putting myself in the readers shoes it made sense to me.
I have a platform of some sort now and I should probably be careful with what I say. Not to tip toe around everything I say and do but just to be respectful. |
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| Respectful or people, and respectful of the truth. One of things that annoys me about media is how little some of those with the largest megaphones care about what comes out of their mouths, or the mouths of their guests. I promise to try to hold myself to a high standard for you. Anyway, I hope you enjoy today’s interview with Jacob Bank! |
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| | INTERVIEW 🎙️ | Jacob Bank, Founder & CEO at Relay.app | Jacob is the Founder and CEO of Relay.app. Prior to founding Relay.app, Jacob was a Director of Product Management at Google, where he led the product teams for Gmail, Google Calendar, and several other Google Workspace products. Before that, Jacob was the Co-Founder and CEO of Timeful (acquired by Google in 2015), a smart calendar that leveraged insights from behavioral psychology and AI to help people spend time on their most important priorities.
He has a BA in Computer Science from Cornell University and was pursuing a PhD in the AI Lab at Stanford before dropping out to found Timeful. | | What was it like getting acquired by Google? | It was a combination of relief, excitement, and a bit of loss. I was originally a PhD student in AI aiming to be a computer science profession, but I ended up dropping out to start Timeful, an AI-powered digital calendar. This was back in 2013 when AI wasn’t quite as mainstream as it is today. We managed to build something great, a highly-rated iPhone app with hundreds of thousands of users, but we frankly didn’t have a great path to become a sustainable business.
When the opportunity came up for acquisition, it was clear that it was our best path to bring what we had built to more people by incorporating our work into Gmail and Google Calendar. | Tell us about what learnings you took from there? | Succeeding at Google is all about managing complexity. You have to build for billions of users, from the CEO of Verizon to a high school student in rural India. You’re under constant scrutiny from journalists and regulators. You have to navigate dozens of internal stakeholders with differing opinions and incentives. So you have to learn a lot to get anything done! | And while I loved my time at Google and did learn a lot, it was pretty much exactly the opposite of what I needed to succeed in a startup. At a startup, you have no inertia, no users, no team, no product, and you need to figure out how to conjure some momentum from nothing. So I pretty much had to unlearn everything I had learned at Google and build a totally new set of skills to get Relay.app off the ground. |  | Big Tech is NOT the Only Answer to Win | Relay.app, Jacob Bank |
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| Tell us about the problem you're trying to solve? | Relay is a platform for building AI agents that work for you. As AI models improve, these agents are going to be able to take on more and more of your work, and we want to make it easy for everyone to take advantage of that. Now, AI can help with the tedious, time-consuming stuff we dread, but soon it will be able to do things that are beyond our current capabilities because they require more knowledge, time, or technical skill than we have. | For example, imagine a CEO who wants to boost their company’s content marketing but finds it too time-consuming to keep up with all of the work—crafting LinkedIn posts, tweeting, replying to comments, creating YouTube videos, writing blog posts, etc. With Relay.app, you can build an AI agent to turn ideas into posts, repurpose content across different platforms, edit and critique content, and much more. In fact, I’ve done all of this. But content creation is just one example. Relay.app is designed to be a versatile tool that can augment your team in every part of your business. Whether you need a customer support agent or a community manager, you can build an AI agent to handle those roles. We use Relay.app internally for everything mentioned so far and more, and it’s enabled us to do a lot with a lean team of nine. |  | Jacob Bank @jebank |  |
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My favorite way to spend a Saturday: making LinkedIn angry with some way I'm using AI to get stuff done 🤣 | | 9:09 PM • Feb 8, 2025 | | | | 2 Likes 0 Retweets | 0 Replies |
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| There are three keys we’ve found to make Relay.app useful. Firstly, it integrates with all the tools we already use—Gmail, Slack, Google Docs, Notion, and more. Secondly, it creates a simple flowchart that makes it easy to understand what the AI is going to do for you and feel confident in its predictability.
And lastly, it lets you keep a ‘human in the loop’ to ensure you end up with high quality work. All in all, I can’t imagine going back to working without it, and many of our customers say the same. | So why did you choose this problem to work on? | When I left Google in the summer of 2021, I had two fundamental insights about what I wanted to build. I don’t think either were groundbreaking or unique to me, but they helped get the startup going in the right direction. The first observation was that real work in today's world requires the use of multiple tools. For instance, setting up this conversation involved using email, Google Calendar, Zoom, and likely other tools like Notion or Google Docs for preparing questions. The challenge I noticed is that most tool developers, including myself in the past, focus mainly on enhancing their specific tools without considering how they integrate with others. At Gmail, we would agonize about making a better reply button but throw up our hands when users wanted use to support use cases the connected Gmail to Zendesk, Salesforce, or the myriad other tools they used.
The second insight was about the potential of AI. Having been an AI researcher and working on AI at Google, I thought that AI could do much more than what we were currently using it for—even way before ChatGPT. |  | Jacob Bank @jebank |  |
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Wondering about the future of VAs... I built my own executive assistant using an AI Agent in @relay and it works pretty well for a bunch of basic email/calendar tasks. And I'm sure I'm only doing a fraction of what I could be doing with it. | |  | | 6:57 PM • Dec 18, 2024 | | | | 3 Likes 0 Retweets | 0 Replies |
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| After putting these together, it still took us two years of exploring and iterating on various tools—a to-do list, a standup tool, a knowledge base, employee onboarding, and performance reviews—all of them fit the basic idea of cross-product workflows powered by AI, but none of them was quite right. | Eventually, we landed on Relay.app as an AI-driven automation and agent-building platform that works across all of your tools, and I’m happy with where we ended up. |
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| | What was the most difficult thing of going from zero to one? | Early go-to-market was so tough. At Google, for example, when I took over Gmail, we already had 800 million users. There was so much positive inertia of existing users and new users signing up everyday that we could just direct all of that potential energy where we wanted it to go with product improvements. In contrast, at Relay.app, we started with nothing—no users, no brand recognition, and barely a product, which is a stark difference. I had to figure out how to get anyone to care about what we were doing, and I didn’t really know where to start. | Two books really helped me figure out what to do. The first was The Mom Test, which teaches you how to ask questions of potential customers that cut through polite but unhelpful feedback. It taught me how to figure out if I had an idea that was actually worth pursuing and how to use informal interviews to get our first fest customers. Every startup founder should read it immediately. | | The second book that really helped me was Traction by Gabriel Weinberg, which offers a structured approach to experimenting with different marketing channels. It outlines a methodology for testing a small set of channels that are likely to work at each stage growth, and ultimately narrow down to one winning channel. We ran this process three times, and it worked every time.
We started with a combination of our networks and relevant communities on Reddit, then graduated to SEO and partner marketing, and are now focused on social media, video content creation, and community marketing. It hasn’t been easy, but it has worked every time. | | How does Relay.app differ from Zapier? | Our users like Relay.app it’s way easier to use, especially for less technical users. It also has intuitive, first-class AI features for everything from summarizing documents to extracting information to generating images, and the human in the loop steps make it easy to stay in control. |  | Relay.app @relay |  |
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🤖 Automate your LinkedIn content creation without sacrificing quality! Turn quick ideas into polished posts with AI using the latest template in our Gallery. Here's how it works: - Looks up your recent posts to ensure the AI will match the style and voice of your most | |  | | 3:46 AM • Feb 8, 2025 | | | | 4 Likes 2 Retweets | 1 Reply |
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| The way we’ve described the product has definitely evolved over time. We've moved away from labeling ourselves as an automation tool in favor of emphasizing our platform for creating AI agents. Literally changing one line on our website from “the new standard for automation” to “a platform to create AI agents that work for you” increased our website conversion by 25%. Turns out a lot of people are looking for ways that AI can help them get work done! | What is your North Star? | My North Star for Relay.app is to build a tool with the ubiquity and value of the spreadsheet for the AI era. I want Relay.app to be useful for every company and every role, adaptable for a variety of tasks at different levels of sophistication, and for it to be a tool that people genuinely love using.
The key metric guiding us toward this goal is cohort retention. With the allure of new AI tools, it's relatively straightforward to attract initial users or even get them to commit financially. However, the real challenge is ensuring they continue to find value in the tool, use it extensively, and incorporate it into their daily workflows.
Retention is crucial because it indicates that users don't just try Relay.app but stick with it, integrating it deeper into their systems and eventually sharing it with their friends and coworkers. If we see people saying unsolicited nice things about us all over the internet, we know we’re on the right track. |  | Customer office hours. |
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|  | Example AI workflow. |
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| Do you run on site hybrid or remote? And why? | We operate fully remotely at Relay.app. This decision stems partly from deliberate choice and partly from necessity since we started the company at the high of COVID. Our team is distributed across Europe and North America. It sounds a bit crazy, but it emerged naturally because we all worked together at Google. As much as I love in-person work, I thought this particular group of people gave us the best change to build a successful company. | While remote work might not be ideal for every company or team, it works well for us. Everyone on the team is pretty senior and autonomous, and we’ve worked together as a team for years. If we had a different company shape, we’d probably choose something different, so I don’t want to claim that fully remote is the right answer for everyone, but it is for us. |
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| | | 💡 Note: If you are looking to hire only the best remote talent on the planet, head over to Athyna and we can help you out. |
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| How do you get the best out of yourself personally and professionally? | For me, it really comes down to doing things that feel natural and authentic. Every time I’ve tried to force something; like some sales strategy I read about in a VC blog post, it just hasn’t worked.
What I’ve learned is that founder-product fit, founder-market fit, and founder–go-to-market fit are all real and really important. I love teaching, I love doing tutorials, I love helping users and jumping into support. And it turns out those are the things that move the needle for us—me posting on Twitter and LinkedIn, doing YouTube walkthroughs, holding office hours with our users. People can tell when you’re genuinely excited and when you care. That authenticity resonates. | | I also try to follow a simple principle of riding the wave. When I’m in flow and inspired, I may work constantly for a couple of weeks and the time will fly by. Other times I’m in a rut and spending more time just doesn’t get me anywhere. So I try to lean into those natural cycles and encourage the team to do the same. | And that’s it! You can also follow Jacob on LinkedIn and X, and check out Relay on their website. |
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| | BRAIN FOOD 🧠 | If you've been here a minute you probably know I was pretty excited about the Deel vs Rippling story, but this episode of My First Million dives into some of the craziest corporate espionage stories you've probably never heard. Sam Parr and Shaan Puri talk about all the shady business that went down between Coke and Pepsi, Oracle and Microsoft and so many more. |  | The Wildest Stories of Corporate Espionage We’ve Ever Heard |
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| | TWEETS OF THE WEEK 🐣 |  | Aaron Levie @levie |  |
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Did something change in robotics like exactly one month ago to make all of this possible. This is crazy. | |  | | 8:20 PM • Mar 20, 2025 | | | | 4.84K Likes 328 Retweets | 637 Replies |
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|  | Marketing Max @MarketingMax |  |
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My favorite thing I found on the internet this week: | |  | | 2:52 PM • Mar 15, 2025 | | | | 143 Likes 29 Retweets | 14 Replies |
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|  | Mads @MadsPosting |  |
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| Bloomberg Markets @markets
Young people looking to save money on their increasingly expensive morning caffeine habit are turning to a throwback: instant coffee trib.al/jkjrEka |
| |  | | 1:48 PM • Mar 21, 2025 | | | | 1.27K Likes 90 Retweets | 46 Replies |
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| | TOOLS WE USE 🛠️ | Every week we highlight tools we actually use inside of our business and give them an honest review. Today we are highlighting Paddle—a merchant of record, managing payments, tax and compliance needs—we use their ProfitWell tool. | beehiiv: We use beehiiv to send all of our newsletters. Attio: We use Attio’s powerful, flexible and data-driven CRM for running this newsletter. Taplio: We use Taplio to grow and manage my online presence. |
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| See the full set of tools we use inside of Athyna & Open Source CEO here. |
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| | | | P.S. Want to work together? | | | That’s it from me. See you next week, Doc 🫡
P.P.S. Let’s connect on LinkedIn and Twitter. |
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