Co-founder of @Tettra. Formerly at HubSpot via Rentabilities (acquired Oct 2013) - I tweet mostly about SaaS and startups.

Boston, MA
Joined February 2009
A lot of founders say they want AI agents, but then you look at some of their processes and it's just 7 manual steps, poorly documented, and nobody bothered to write it down properly. So the agent is supposed to magically understand the messy thing the team itself can't even explain? Not how it works. Make sure you have super clear guidelines for your work, clear enough that any human (VA, support staff, etc.) could follow it easily. Then you can deploy AI.
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Andy Cook retweeted
What if Granola and @lennysan had a baby? That's what I built into Work Coach. World class insights personalized and delivered when most helpful.
Today I'm releasing my entire newsletter archive (350+ posts) and all podcast transcripts (300+ episodes) as AI-friendly Markdown files. Plus an MCP server and GitHub repo. A few months ago I shared my podcast transcripts on a whim, and y'all built the most amazing things—an RPG game, a parenting wisdom site, infographics, a Twitter bot, and 50+ other projects. Let's see what happens when I give you even more data. Grab the data here: LennysData.com. Paid subscribers get all of the data (some 350 posts and 300 transcripts). Free subscribers get a subset. I don’t think anyone’s ever done anything like this before, and I’m excited to give you this excuse to play with that AI tool you've been meaning to try. Here’s my challenge to you: build something, and let me know about it. I’ll pick my favorite and give you a free 1-year subscription to the newsletter. Just post a link to your project in the comments here: lennysnewsletter.com/p/how-i…. If you’ve already built something, slurp in this new data and submit it, too. I’ll pick a winner on April 15th. Check out today's newsletter post for inspiration on what you could to build: lennysnewsletter.com/p/how-i… LFG.
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💁🏽‍♀️ Big News! 💁🏽‍♀️ 🎙️ The first episode of Live Chat with Jen Weaver is here! 🔥 Ep 1: AI as Your Second Brain: Meg Palazzolo Builds a User Journey Map ⏳ Short enough for your lunch break. Listen now: buzzsprout.com/2433498 #SupportOps #CustomerExperience #PodcastLaunch
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After 9 intense years of building Tettra, we decided it was time for an acquisition.
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Andy Cook retweeted
Really enjoyed the recent discussion with Reid Hoffman and Peter Theil. During the discussion on innovation in large companies, this quote really got me thinking: "You need someone who has a founder mindset and acts with moral authority." ~Reid Hoffman --- Anyone can have a "founder mindset", but not everyone has the "moral authority" of a founder. I wonder if that "moral authority" is really necessary though. When large companies struggle to innovate, I don't think it's because the leaders lack the moral authority of a founder. I think the challenge is more the "Innovator's Dilemma". Part of their job as a leader is to protect what exists and it's hard to prioritize things that have unproven returns when there are so many things that have a high probability of positive returns. As a long-time founder at HubSpot, now an 8,000+ company, I've been a student of this topic for a long time -- it's a fascinating one. Here are a few lessons I've learned: 1) You can't try and decide whether you should fund a specific innovation project. Instead, you have to decide that you're going to allocate *some* percentage of resources on innovation projects. *Then* you decide how best to allocate *that* pool of resources. Reason: When you look at individual innovation projects in isolation, very few (if any) projects will make the cut. 2) Don't measure new, innovation projects by your existing metrics -- at least not when you're starting. Just about every innovation project is going to look like a piddly rounding error when it starts. What you're looking for is not revenue, but *evidence*. Evidence that there is a potential large opportunity out there. 3) Know the difference between "experiments" (we're going to see whether this new thing has a there, there) and "imperatives" -- we're going to DO THIS NEW THING. Both are fine -- just know which bucket any particular project falls into. Example: We've run a lot of experiments at HubSpot. Some worked out, some did not. But, when we decided to build HubSpot CRM, we decided it was an *imperative*. We made it clear to the team that whether it took 2 years or 20, we *were* going to build a CRM. It was not an experiment. 4) Be prepared to double-down (or quintuple down) on the things that are working. Once you see the evidence, you have to get a large bet on the table. Without that, pretty much all experiments will eventually fail. Still learning, so I could be wrong about those -- it's just my personal experience.
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Andy Cook retweeted
Big news! We're excited to share that our AI Slack bot, Kai, just got a significant upgrade! Now, Kai does more than just answer questions—you can build and maintain your knowledge base, all within Slack. tettra.com/integration/slack… #SlackIntegration #KnowledgeManagement
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Andy Cook retweeted
Business documentation might sound boring. But it’s your golden ticket. It’ll allow you to quickly train new hires and it will bet you a premium when you’re acquired.
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I’ve secretly 🤫 been using a new product every week that is now live for everyone. Today we are launching Reforge Artifacts and it’s completely free 🆓. Take a look 👇 Artifacts let you access the real work from those who have done it before, so you’ll never have to start from scratch. Some examples: 👆 Product Review Systems from Casey Winters, Tom Willerer, and others 🧠 Product Strategy and Roadmaps from Adam Fishman and Sachin Rekhi 🪜 Career Leveling Guides from Julie Zhou, Barron Ernst, and Kevan Lee 🧪 Growth + Product Experiments from Lauryn Isford, Matt Woods, and Ben Williams 📈 Quantitative analyses from John Egan, Dan Wolchonok, and Yousuf Bhaijee 🧐 User research projects from Amber Rucker, Mike Fiorillo, Shelly Eisen-Livneh And sooooo many more. You can sign up here → reforge.com Preview some artifacts here → artifacts.reforge.com/artifa… These are NOT blank templates. Artifacts are the real work that contain the substance, nuance, insights, and realness. Here are a few things you can do with Artifacts: 🔎 Find artifacts relevant to what you are working on 💡 Access notes from the creator about the story, lessons, and insights ⭐️ Save artifacts and share them with colleagues 🔁 Remix artifacts to create your own version Artifacts is such a simple but powerful idea I can’t believe we didn’t think of it before. I’ve wasted so much time recreating something thousands of others have already done. Artifacts can help accelerate a lot of work (like open-source code) by enabling building on each other. Would love to know what you think.
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New hire: Where’s the documentation? Senior:
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Andy Cook retweeted
People tend to either bring positive energy to people around them at work, or require energy from others to stay positive. Aside from specific skills, one of the things founders are desperately looking for is people who can help shoulder the positive energy burden with them.
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Andy Cook retweeted
opinion — only work on a startup if it fits 1 of these criteria, and ideally both: - you want to spend a lot of time using the product - you want to spend a lot of time with the people who use the product
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Building a startup is really fun if you enjoy being head of sales, marketing, product, operations, support, recruiting, and memes all at once. – at San Mateo, CA
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Aaron Levie
@levie3 Jun 2022
Despite the market volatility, there’s still near-unlimited opportunity to build software for people that solves important problems (whether they know they have the problem or not yet)!
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Recent insight: at somewhere around 10 team members in a remote team you need to gratuitously document "how we work" including nitty gritty on when and how to use each tool for remote communication/collaboration.
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What I thought was going to be 2-3 other folks who'd push each other to grow on Twitter turned into 100+ 🤯 The goal? DOUBLE your Twitter followers in 3 months. Here's the quick start guide to building an audience on Twitter. 🧵
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Andy Cook retweeted
Just the initiative I was looking for. I will match @balajis donation of $50/RT up to $100k to help India fight the COVID tragedy. Thank you. 🙏
If you’ve been fortunate enough to do well this year, consider joining me and @VitalikButerin by donating at the addresses below. But if all you have is Twitter, help spread the word. For every RT, I’ll donate another $50 to fight COVID in India, up to $100k. #cryptovscovid
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If you want to know how to do CX just follow what @aacook does w/ NanaGram customers. I forgot to update my grandma’s address when she moved 2 mo ago. When I told Alex he re-printed the last 3 mos to send her + included a photo album + chocolates! Like what?! The actual best.
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Andy Cook retweeted
So I'm mentoring a few students in a college course about building MVPs. One of the students in my is actually built a prototype for an automated HEIC > JPG conversion tool for Airdrop. Any of my followers also want this to exist and willing to talk to him, join the beta?
Mac app that looks for HEIC files in your Downloads folder and automatically converts them to JPEG.
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Work on your processes as much as your product.
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Andy Cook retweeted
There's a point between v1 and product market fit where there are no major lessons to be learned. Really, just a plain 'ol grind building a long list of things users need to make the product great and usable. You found the problem, it's time to execute.
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