Building the Next Big Thing with Jacob Bank

In this episode of Smooth Operators Guide by Live Docs, we had the pleasure of chatting with Jacob Bank, founder and CEO of Relay. Jacob has an extensive background in AI, product management, and workflow automation. His journey began as an AI researcher at Stanford, where he explored machine learning in social science contexts, focusing on time management and decision-making. 

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In 2021, Jacob left Google to start Relay, a cutting-edge automation tool that streamlined repetitive tasks with AI-enhanced workflows and human oversight. Relay stands out as a next-generation alternative to Zapier, integrating AI more deeply into productivity processes.

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We're thrilled to have him on this edition of our biweekly newsletter to share his insights and expertise. So, without further ado, let's get into it:

From Academia to Automation

Ani: Hi Jacob, can you introduce yourself to our listeners?

Jacob: Sure! I’m Jacob Bank, founder and CEO of Relay. My background is in AI research; I was pursuing a PhD at Stanford, focusing on how machine learning intersects with social science. I explored topics like information spread on Twitter and how AI could help with time management and decision-making.

Ani: How did you transition from academia to the tech industry?

Jacob: I co-founded Timeful, it is an AI-powered digital calendar that prioritizes personal tasks and goals.

Google acquired us in 2015, where I spent six years leading product teams for Gmail, Google Calendar, and other productivity tools.

Ani: And what led you to start Relay?

Jacob: After leaving Google in 2021, I started Relay to create a best-in-class automation tool. Relay makes it easy to automate repetitive tasks using AI, offering a next-gen alternative to Zapier with a focus on human oversight and control.

Ani: Wow, that's fantastic. I actually love productivity in general. I remember taking a course called "Learning How to Learn" right out of university. It was taught by Terence Wajinoski, who discussed managing time and various productivity techniques.

Jacob: Productivity advice often comes from a personal success story, like "Here's exactly what I do." However, each person's productivity system needs to be tailored to their unique goals and working style. General principles, such as prioritizing important tasks at your peak productivity times, are universal. For me, mornings are the most productive. Your ideal system may differ based on your natural rhythms and preferences.

Ani: Interesting. Transitioning from a PhD student at Stanford to founding and then selling a company to Google must have been significant. What motivated these changes, and how did each experience shape your approach to product development?

Jacob: The shift from academic research to entrepreneurship was accidental. While working on an AI-powered digital calendar for a research project, my advisor suggested it would be better suited as a startup. Initially resistant, I later realized I was more suited for a startup environment than academia.

The Google acquisition was a strategic decision. We had a successful product but struggled to scale it into a lasting business. Google offered an opportunity to integrate our work with their vast user base, which was a logical next step for our product.

My move from Google to starting a new company was deliberate. After leading a large organization and managing billion-user products, I wanted to return to the startup world. The freedom and rapid learning of starting from scratch were what motivated this transition.

No Pain, No Gain!

Ani: Interesting. Given that this is your second startup, Relay, and considering your previous experience with Timeful and Google, what are some key lessons or changes you're implementing this time around?

Jacob: At Relay, I'm mostly making different mistakes, though some are similar. A major lesson is the importance of focusing on the core product rather than expanding features prematurely. With Timeful, we made two significant mistakes:

1. Generic Product Design: We created something too broad and not tailored to user needs, driven more by our theoretical research than user feedback.
2. Feature Expansion: We kept adding new features—tasks, events, habits, projects—hoping one would lead to growth. Joe Krause from Google Ventures pointed out that expanding features often don't solve the fundamental issue of lacking product-market fit. Instead, it's crucial to refine the core product.

At Relay, we’re prioritizing perfecting the core automation features before considering additional features. This focus on core mechanics and user delight is key to our strategy for sustainable growth.

Ani: It sounds like you’ve had some insightful experiences with both startups. How did your approach change from Timeful to Relay?

Jacob: At Relay, we’ve learned to prioritize refining the core product before adding new features. At Timeful, we made the mistake of over-expanding our feature set before achieving product-market fit. We initially aimed to create entirely new categories, but it’s often more effective to build within established categories and innovate from there.

Here’s a key lesson from Timeful that we only corrected too late:

We were focused on creating a new category, convinced that our innovative approach would be groundbreaking. We didn’t heed the feedback that existing categories struggled to achieve lasting success.

When we started Relay, we initially pursued similar category-creation concepts, like an automated to-do list or a live-updating knowledge base. However, positioning ourselves within the established automation category—while innovating with AI and human-in-the-loop elements—proved more effective. It’s easier to explain how you're different and better than something people already understand, rather than trying to create a new category.

In summary, refining your core product and positioning within known categories can make it easier to communicate your value and achieve growth.

Innovation and Intuition

Ani: Your experience with AI-driven features across Google Workspace, Timeful, and Relay highlights a nuanced approach. What drove you towards AI, and what are the key considerations for integrating it into productivity tools?

Jacob: My core belief is that the human-in-the-loop experience is as crucial as the underlying AI model. For instance, with Smart Compose in Gmail, the interface design—how you use features like italics, ghost text, and completion options—was pivotal. The same model could be either unlaunchable or deeply loved depending on its user experience.

“As AI models become more advanced, it’s tempting to focus solely on their capabilities.”

However, delivering them with a well-considered user experience is essential. This means ensuring that users can easily oversee, adjust, and add personal context to AI outputs. AI is powerful, but trust and reliability in high-stakes scenarios often require human oversight.

This balance—between leveraging AI’s capabilities and maintaining human control—is fundamental. It ensures that AI tools not only perform effectively but also align with user needs and expectations. It’s about evolving AI while keeping the human element integral to the process.

AI? Aye Captain! 

Ani: How much do you incorporate AI into your daily routine, and what tasks do you automate with it?

Jacob: My AI usage leans heavily towards automation. Here’s a breakdown of how I use AI:

1. Categorizing Support Tickets: We use AI to classify support tickets automatically—whether they're bugs, usability issues, feature requests, or use case questions. This helps us track patterns and gather product insights efficiently.
2. Summarizing Documents: I rely on AI to distill long-form documents into bite-sized summaries. This includes meeting notes, blog posts, or competitor analyses, helping me quickly grasp essential information.
3. Content Creation: AI assists with proofreading, ensuring spelling, grammar, and tone adhere to our style guide.
4. Auto-Generated Tutorials and Videos: We’re experimenting with auto-generated content, including tutorials and videos. This involves AI creating narrations, voiceovers, and even screen captures, showcasing how AI can handle previously challenging tasks.

The evolution of AI capabilities, especially in content generation and summarization, is exciting. It’s making tasks that were once labor-intensive much more manageable and efficient.

Competing with Industry Titans

Ani: Considering Zapier's success with programmatic SEO, how are you planning to make an impact in the same category? Are there any innovative strategies you're working on?

Jacob: We approached this with a mix of caution and curiosity. Here’s what we discovered:

1. Targeted Ranking: Even if we can’t rank number one, securing positions two, three, or four for specific queries (like integrating Gmail and Notion) still drives substantial traffic.
2. Enhanced Content: We identified gaps in Zapier’s approach—like the lack of detailed setup instructions on their programmatic landing pages. To address this, we developed auto-generated tutorials that provide step-by-step guidance on configuring various integrations. These tutorials have successfully ranked highly for detailed queries in the "how to do X" category.

The key takeaway is not to shy away from competitors. Embrace the competition as it indicates a valuable problem that people care about. Even if a competitor has a strong presence, there are always opportunities to differentiate and improve on specific dimensions, both in product and marketing.

Future-Proofing Productivity with AI

Ani: How do you envision AI transforming productivity tools in the next five or ten years? Will it be fully automated, or will human touchpoints remain essential?

Jacob: I believe that human touchpoints will always be necessary, though their role will change as AI models become more advanced. In the future, AI will play a significant role in productivity tools by acting as a co-pilot, helping with tasks such as writing emails, composing documents, editing content, and categorizing support tickets. AI will become an expected part of productivity tools, enhancing efficiency and functionality.

However, chatbots present a more uncertain future. While they can be useful for certain tasks like research and data interrogation, they come with challenges. Users need to know what to ask, and there are still significant usability issues to overcome. As a result, the long-term role of chatbots is less clear.

I’m particularly excited about the potential for automation assistants that run in the background, handling routine tasks such as confirming meeting attendance and categorizing support requests.

These assistants will likely become integral to our productivity tools, streamlining processes and making our work more efficient.

Overall, AI will significantly enhance productivity, but human oversight and interaction will remain crucial to ensure that tasks are completed accurately and contextually.

Mentors and Essential Tools

Ani: Jacob, your career trajectory, from pursuing a PhD to starting startups and working at Google, showcases immense resilience and depth. Have there been any notable mentors or influential figures who've significantly impacted your career?

Jacob: Absolutely. Throughout my career, I’ve been fortunate to have several influential mentors. The most significant has been Yawaf Shoam. He was my academic advisor, and co-founder at Timeful, and has continued to guide me through my work at Google and now at Relay. His mentorship has been foundational to my career in entrepreneurship.

Another key mentor has been Kevin Smilak, my engineering counterpart at Google. He taught me how to navigate the complexities of scaling products within a large organization, and I still consult him for major life decisions. Beyond these long-standing relationships, I’ve also benefited from guidance from investors and board members at various stages. People like Ali Partovi, Sandhya, Christina, and Keith Rabois have all provided critical insights and support.

Additionally, having a network of fellow startup founders, both ahead of and behind me in their journey, has been invaluable. I frequently connect with peers like Zach Lloyd from Warp.dev and Boaz Hecht from Aidflow to share experiences and gain perspective.

Rapid-Fire Round

Ani: That’s wonderful to hear. Now, for a quick rapid-fire round, I'd love to know about the tools you use daily. What would you consider your Swiss Army knife?

Jacob: For me, it would be our product, Relay, as it helps automate and streamline many tasks flexibly. But if I had to choose a non-self-serving option, Slack would be my go-to Swiss Army knife. It’s incredibly versatile for communication, updates, and automation.

Ani: Is there any tool you can't live without, something super essential to your daily operations?

Jacob: Besides Relay, I’d say Gmail. Despite predictions about the decline of email, it remains a critical tool for interacting with the outside world and managing communications.

Ani: Lastly, are there any undiscovered gems or lesser-known tools in your stack?

Jacob: One intriguing tool we’ve recently started using is Synesthesia for auto-generating AI-powered videos. It’s a fascinating and powerful tool that's proving to be quite useful. Other than that, our core tools like GitHub, Figma, Linear, and Notion are well-known but indispensable in our workflow.

Ani: Jacob, is there anything new in your stack that’s recently been added and has added significant value?

Jacob: Yes, we've recently started using a tool called Frase. It helps us refine and optimize our content for SEO by analyzing a webpage, identifying keyword opportunities, and suggesting improvements to enhance page quality. This has been particularly valuable as we focus on SEO and content strategy.

Ani: That’s great to know. To wrap up, is there anything you’d like to share with the audience, and where can people connect with you?

Jacob: Feel free to connect with me on LinkedIn, as I’m more active there. If you sign up for Relay.app and email support@relay.app, there's a good chance I'll be the one answering your support queries. I enjoy interacting with users and addressing any issues they might have.

Ani: Thank you for joining us, Jacob.

Epilogue

Jacob shares his vision for the future of AI in productivity tools, highlighting the need for human touchpoints:

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Key Takeaways #1: Integrating AI into productivity tools requires a human-in-the-loop approach and a focus on the user experience.

Key Takeaways #2: Competition should be embraced as an opportunity for improvement.

Key Takeaways #3: AI will significantly assist productivity tools, but human touchpoints will still be necessary.

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