Three Kinds of Software Survive: Tasklet's Andrew Lee on Competing to be a Horizontal Platform
Andrew Lee, CEO of Tasklet, returns for his fourth appearance to share how his team has once again rewritten their entire agent stack, now emphasizing file system context, agentic search, and multi-resolution summarization. The conversation digs into the strategic tension of competing with your own supplier, as Anthropic's Claude Max accounts offer direct customers far more tokens than API partners get at the same price. Andrew also lays out his framework for the only three types of software companies that will survive the AI transition and discusses Tasklet's evolution toward becoming a model-agnostic horizontal platform.
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Always Bet on the Models: How Tasklet Puts the Agency in Agents, with CEO Andrew Lee
Today Andrew Lee, founder and CEO of Shortwave and Tasklet.ai, joins The Cognitive Revolution to discuss building a new AI agent automation platform that replaces traditional workflow tools with conversational, long-lived agents, exploring how betting on rapidly improving model capabilities enables more flexible automation across thousands of business integrations while navigating the challenges of reliability, cost management, and the emerging paradigm of virtual employees.
Shownotes brought to you by Notion AI Meeting Notes - try one month for free at: https://notion.com/lp/nathan
Agent-first vs. workflow-first approach: Task Lit fundamentally differs from traditional automation tools by using a single AI agent that handles all tasks through natural language, rather than building explicit workflows or state machines.
Speed is the only remaining moat: In the AI era, traditional competitive advantages are evaporating so quickly that the only sustainable advantage is moving faster than competitors.
Small business marketing as near-term target: The technology is approaching "best available human" performance for tasks like small business marketing, where hiring quality human help is difficult.
Sponsors:
Google Gemini Notebook LM:
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Tasklet:
Tasklet is an AI agent that automates your work 24/7; just describe what you want in plain English and it gets the job done. Try it for free and use code COGREV for 50% off your first month at https://tasklet.ai
Linear:
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Shopify:
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How Shortwave Wants To Reinvent Email With AI
In this episode of The New Stack Agents, Andrew Lee, co-founder of Shortwave and Firebase, discusses the evolution of his Gmail-centric email client into an AI-first platform. Initially launched in 2020 with traditional improvements like better threading and search, Shortwave pivoted to agentic AI after the rise of large language models (LLMs). Early features like summarization and translation garnered hype but lacked deep utility.
However, as models improved in 2023—especially Anthropic’s Claude Sonnet 3.5—Shortwave leaned heavily into tool-calling agents that could execute complex, multi-step tasks autonomously. Lee notes Anthropic’s lead in this area, especially in chaining tools intelligently, unlike earlier models from OpenAI. Still, challenges remain with managing large numbers of tools without breaking model reasoning.
Looking ahead, Lee envisions AI that can take proactive actions—like responding to emails—and dynamically generate interfaces tailored to tasks in real-time. This shift could fundamentally reshape how productivity apps work, with Shortwave aiming to be at the forefront of that transformation.
Learn more from The New Stack about the latest insights of the power AI at scale:
Why Streaming Is the Power Grid for AI-Native Data Platforms
Companies Must Embrace BeSpoke AI Designed for IT Workflows
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Shortwave Rides the Tidal Wave: Inbox Agents, Hyper-Growth & Hiring AI Managers, with CEO Andrew Lee
In this episode of the Cognitive Revolution podcast, Andrew Lee, founder and CEO of Shortwave, returns to discuss the rapid advancements in AI over the past year and how they have significantly improved Shortwave, an AI email assistant. Andrew shares insights into the exponential growth of Shortwave's revenue and the enhanced capabilities of their AI, which now functions more like a virtual assistant. They delve into various use cases, the technical evolution of their platform, the impact of new AI models, and their strategic decision to shift from being an AI-enhanced email client to offering a broader AI-driven communication solution. Andrew also talks about the shift in company culture towards an AI-forward approach, the importance of speed and agility in the AI space, and the increased productivity achieved through leveraging AI. The conversation also touches on the future of the software industry, the potential of AI to automate routine tasks, and the company's hiring strategy focused on people who are passionate and forward-thinking about AI.
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CHAPTERS:
(00:00) About the Episode
(04:00) Introduction and Welcome Back
(04:07) Shortwave's Evolution and Revenue Growth
(05:09) AI Email Assistant: Then vs. Now
(06:44) Exciting Use Cases of Shortwave
(14:11) Technical Deep Dive: Database and Search Stack
(23:44) Agent Behavior and Iterative Approach
(34:04) Model Selection and Cost Optimization
(39:53) Future of AI and Convergence of Providers
(42:54) Exploring the New Cursor Agent Mode
(44:07) Understanding AI Filters and Their Functionality
(45:38) Challenges and Solutions in AI Email Management
(49:24) Evaluating AI Models and Their Performance
(55:53) The Role of AI in Enhancing Email Communication
(57:05) The Future of AI in Communication Tools
(01:12:35) Building an AI-Forward Culture at Shortwave
(01:17:14) Leveraging AI for Content Creation
(01:17:57) The Shift in Team Dynamics
(01:19:36) Adapting to Industry Changes
(01:20:39) Optimizing for Speed
(01:22:45) Monetization and Pricing Strategies
(01:25:42) The Future of AI Integration
(01:36:36) Hiring and Team Structure
(01:43:28) The Future of Software Development
(01:47:18) Closing Thoughts and Future Outlook
(01:50:03) Outro
SOCIAL LINKS:
Website: https://www.cognitiverevolution.ai
Twitter (Podcast): https://x.com/cogrev_podcast
Twitter (Nathan): https://x.com/labenz
LinkedIn: https://linkedin.com/in/nathanlabenz/
Youtube: https://youtube.com/@CognitiveRevolutionPodcast
Apple: https://podcasts.apple.com/de/podcast/the-cognitive-revolution-ai-builders-researchers-and/id1669813431
Spotify: https://open.spotify.com/show/6yHyok3M3BjqzR0VB5MSyk
Making Email Better With AI At Shortwave
Summary
Generative AI has rapidly transformed everything in the technology sector. When Andrew Lee started work on Shortwave he was focused on making email more productive. When AI started gaining adoption he realized that he had even more potential for a transformative experience. In this episode he shares the technical challenges that he and his team have overcome in integrating AI into their product, as well as the benefits and features that it provides to their customers.
Announcements
Hello and welcome to the Data Engineering Podcast, the show about modern data management
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Your host is Tobias Macey and today I'm interviewing Andrew Lee about his work on Shortwave, an AI powered email client
Interview
Introduction
How did you get involved in the area of data management?
Can you describe what Shortwave is and the story behind it?
What is the core problem that you are addressing with Shortwave?
Email has been a central part of communication and business productivity for decades now. What are the overall themes that continue to be problematic?
What are the strengths that email maintains as a protocol and ecosystem?
From a product perspective, what are the data challenges that are posed by email?
Can you describe how you have architected the Shortwave platform?
How have the design and goals of the product changed since you started it?
What are the ways that the advent and evolution of language models have influenced your product roadmap?
How do you manage the personalization of the AI functionality in your system for each user/team?
For users and teams who are using Shortwave, how does it change their workflow and communication patterns?
Can you describe how I would use Shortwave for managing the workflow of evaluating, planning, and promoting my podcast episodes?
What are the most interesting, innovative, or unexpected ways that you have seen Shortwave used?
What are the most interesting, unexpected, or challenging lessons that you have learned while working on Shortwave?
When is Shortwave the wrong choice?
What do you have planned for the future of Shortwave?
Contact Info
LinkedIn
Blog
Parting Question
From your perspective, what is the biggest gap in the tooling or technology for data management today?
Closing Announcements
Thank you for listening! Don't forget to check out our other shows. Podcast.__init__ covers the Python language, its community, and the innovative ways it is being used. The Machine Learning Podcast helps you go from idea to production with machine learning.
Visit the site to subscribe to the show, sign up for the mailing list, and read the show notes.
If you've learned something or tried out a project from the show then tell us about it! Email hosts@dataengineeringpodcast.com) with your story.
Links
Shortwave
Firebase
Google Inbox
Hey
Ezra Klein Hey Article
Superhuman
Pinecone
Podcast Episode
Elastic
Hybrid Search
Semantic Search
Mistral
GPT 3.5
IMAP
The intro and outro music is from The Hug by The Freak Fandango Orchestra / CC BY-SA
Sponsored By:
Starburst: 
This episode is brought to you by Starburst - a data lake analytics platform for data engineers who are battling to build and scale high quality data pipelines on the data lake. Powered by Trino, Starburst runs petabyte-scale SQL analytics fast at a fraction of the cost of traditional methods, helping you meet all your data needs ranging from AI/ML workloads to data applications to complete analytics.
Trusted by the teams at Comcast and Doordash, Starburst delivers the adaptability and flexibility a lakehouse ecosystem promises, while providing a single point of access for your data and all your data governance allowing you to discover, transform, govern, and secure all in one place. Starburst does all of this on an open architecture with first-class support for Apache Iceberg, Delta Lake and Hudi, so you always maintain ownership of your data. Want to see Starburst in action? Try Starburst Galaxy today, the easiest and fastest way to get started using Trino, and get $500 of credits free. [dataengineeringpodcast.com/starburst](https://www.dataengineeringpodcast.com/starburst)
Dagster: 
Data teams are tasked with helping organizations deliver on the premise of data, and with ML and AI maturing rapidly, expectations have never been this high. However data engineers are challenged by both technical complexity and organizational complexity, with heterogeneous technologies to adopt, multiple data disciplines converging, legacy systems to support, and costs to manage.
Dagster is an open-source orchestration solution that helps data teams reign in this complexity and build data platforms that provide unparalleled observability, and testability, all while fostering collaboration across the enterprise. With enterprise-grade hosting on Dagster Cloud, you gain even more capabilities, adding cost management, security, and CI support to further boost your teams' productivity. Go to [dagster.io](https://dagster.io/lp/dagster-cloud-trial?source=data-eng-podcast) today to get your first 30 days free!
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The AI Email Assistant I've Been Waiting for, with Andrew Lee of Shortwave
In this episode, Nathan sits down with Andrew Lee, founder of Shortwave, an AI-powered email app that describes itself as “the smartest email app on planet earth.” They discuss Shortwave’s RAG stack, how the AI assistant works, the models Shortwave is using, and much more. This is truly a masterclass in RAG app development.
Sponsors :
Oracle Cloud Infrastructure (OCI) is a single platform for your infrastructure, database, application development, and AI needs. OCI has four to eight times the bandwidth of other clouds; offers one consistent price, and nobody does data better than Oracle. If you want to do more and spend less, take a free test drive of OCI at https://oracle.com/cognitive
The Brave search API can be used to assemble a data set to train your AI models and help with retrieval augmentation at the time of inference. All while remaining affordable with developer first pricing, integrating the Brave search API into your workflow translates to more ethical data sourcing and more human representative data sets. Try the Brave search API for free for up to 2000 queries per month at https://bit.ly/BraveTCR
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TIMESTAMPS:
(00:00) - Intro
(01:07) - Shortwave: AI-Powered Email
(06:22) - Genesis of Shortwave
(15:25) - Sponsors: Oracle / Omneky
(16:46) - Data Processing Pipeline
(21:57) - Choosing a Vector Database
(26:34) - How the AI Assistant Works
(36:24) - Sponsors: Brave / Plumb / Squad
(40:53) - Fine-Tuning & Hosting Models
(45:11) - Email Automation
(47:55) - Email Retrieval
(51:44) - Optimizing AI Performance
(53:20) - Safety & Embedded Ethics
(01:04:51) - Strategic Product Launches
(01:09:58) - Inbox Management
(01:12:24) - The Future of Collaborative AI
(01:18:54) - Scaling Personalized Outreach
(01:26:04) - Closing Thoughts & What's Next