Matthew O'Connor

Project update! My application tracking extension is now doing fuzzier matching and injecting new information into LinkedIn (and other sites) to keep me from doubling up on applications. Next up: local storage and bulk import/export operations...

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Recently, I introduced Ava, a custom GPT to help Engineering Managers with planning, strategy, hiring, etc. I ran an experiment with Ava to role-play an interview. 💬 Ava took on the role of an interviewer and an EM candidate. It generated questions, answered them, and graded the responses. It was like running a real interview, but with a AI doing most of the heavy lifting! While the answers weren’t as detailed as you'd get in a real interview, the results were interesting 👉 https://lnkd.in/ec488vy6

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Here's something counterintuitive; taking on more investment risk reduces long-term returns: https://lnkd.in/gHwkjHmP This is only my second investment video, so I'm still learning. If you have any feedback, I would love to hear it. Based on the feedback from the first video, I tried to make the audio more balanced on this video. I also shortened the length, to make the content more digestible.

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Last Tuesday, Malsgufa, our legacy CMS backend, was shut down. This milestone for BI's Tech and Product team culminated years of planning, effort, and execution. Malsgufa's first commit was on July 25, 2014, leading to 5,186 commits across nearly 30 repositories. Built and maintained by scores of engineers, its deprecation represents significant cost savings (20 production replicas, 3 instances of Solr, and an insane number of Zookeeper instances!), reduced security risk, and the elimination of an often-blamed boogeyman. The journey began in January 2020. Our challenge: moving traffic off Malsgufa without rebuilding everything in Muse. Initially, we tried GraphQL as an intermediary between Viking and our services, but progress was limited by Viking's complex Angular/Vue architecture. In January 2023, we pivoted to the strangler fig pattern with a shim. This approach proved far more effective – all Malsgufa traffic went through the shim first, with verbose logging to track unhandled requests. Meanwhile, we built Story Versioning API (SVAPI), incorporating lessons learned from Malsgufa's limitations around history and publishing states. We ran four major migrations (stories, custom pages, slideshows, and videos), building support in Muse and shimmed compatibility for Viking. Traffic gradually decreased from a torrent to a trickle, leading to the gloriously uneventful shutdown. Next, we will deprecate Viking by Q2 2025, unifying our users in the Muse ecosystem to create the industry's most innovative CMS. Special thanks to the entire Story Creation team: Chase Gruber, Chris Speziale, Daniel Arita, Danny Feliz, Dasha Lary, Dawin Camillo, Eric Saam, Frederica Chen, John Laslo, Kelly Filush, Morgan Cohn, Sarah Pai, Tyler Greenfield! Thanks also to DaD, Engagement, Helpfulness, Cloud Engineering, Test Engineering, and Operational Excellence! Finally, we recognize Malsgufa itself. Developed as a unified CMS backend to support Business Insider's expansion into new markets, it served our global newsroom reliably for a decade, publishing millions of stories despite no major changes in recent years. While it became less sustainable as our business evolved, it deserves our respect. Thank you, Malsgufa. May you rust in peace.

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The difference between a decision and a data-driven decision is like the difference between a shot in the dark and a carefully aimed arrow. Which decision do you want to make?

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Thank you so much, Jeremy Kahn for the great conversation this week at Fortune #BrainstormAI on the future of Google Search and how we’re expanding what’s possible with AI. One of the most exciting parts of working on Google Search is the immense opportunity we have with AI to be even more helpful – the truth is, there aren’t just billions of questions that people ask Google every day, there are billions of questions that people don’t ask at all – because it’s too hard to formulate the question, or they aren’t sure whether they’ll get a useful answer. In this next era of Search, we really want to  make it truly effortless to ask any question, make sense of any type of information, across all modalities – whether that’s video, image, or text. That includes asking your question in any way that’s most natural to you - think about Google Lens, where you can search what you see, and get an AI Overview with context and links to better understand it. There’s an even greater opportunity as our AI models continue to improve. Just this week, the Google DeepMind team showed off a range of new capabilities with Gemini 2.0 (https://bit.ly/3ZU3JVe), which we’re already testing in AI Overviews so people can tackle even harder questions. And the Android team shared a glimpse into how we’ll help people better understand and interact with the world around with the new XR operating system (https://bit.ly/3ZRx9TR). What’s most exciting to me is how AI is unlocking entirely new ways to make information useful, so regardless of what language you speak, or your skill level in a particular domain, we can help you understand information effortlessly. I can’t wait for the year ahead for Search – there’s so much more to come! You can check out our full conversation at Fortune Brainstorm AI here: https://bit.ly/3DmPdMA 

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"Build in primitives" -Andy Jassy, #Amazon CEO https://lnkd.in/gHMYt7NX Happen to take the time to read this year's Annual investor letter from Andy Jassy. Deep in 2nd half, it talks about how Amazon started thinking about "building in primitives" and how it has been game-changing for them and their customers. Probably old news for some, but eye-opening for me. Definitely a good read!

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🍜Anybody up for some ramen? I am excited to share that I am back in the garage, building again (it’s actually a house in the Berkeley Hills). We are taking the wraps off of Supercog AI, a new startup focused on solving Application Integration using LLM powered agents. My co-founder in this new venture is a great friend of mine (and a former co-founder partner), Alex Osborne. Alex and I have worked around the application integration space for a long time, and we are unrealistically excited about applying the GenAI stack to this problem. Not many people relish the task to get some bits to move from system A to system B. But it’s a critical job to be done, and that’s led to a lot of brittle scripts, a myriad of inflexible “no code” tools, and a lot of hand crafted SQL. But the power of the Large Language Model, trained on a huge corpus of information, offers a remarkable tool to solve this problem. The LLM you use today already knows the APIs of hundreds of popular systems. It knows the SQL dialects of every major database. It understands the semantics and data schemas of many popular SaaS systems. It understands much of the specific domain in which your business operates. I like to call the AI revolution “the last platform shift”. That may turn out to be hyperbole, but I definitely believe we are in the very early stages of seeing what this new stack can enable. I know we are hardly the first folks to claim that “amazing stuff is coming!”. But this is why Alex and I have decided to focus on a real and hard problem. If we can prove that LLMs can power a new way to solve this problem, it will be the first successful *new* approach in 15 years.. We will have much more to share about this new platform soon. In the meantime, if you’re interested in getting a peek - or even better if you have application or data integration tasks that you would like some help with - please reach out because we want to help. #genai #startups #backinthegarage

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It's probably no surprise to anyone that knows me well, that I love self-development podcasts. One of my favorite is Ramit Sethi's I will teach you to be rich (aka Money for Couples). I recently got this email newsletter When I ask people what their Rich Life looks like, most people say something like: "I want to do what I want, when I want."   Success is rarely a dollar amount. Most people want a lifestyle. In the workplace, this means having a flexible job.    Which might look like: -Never having to do the daily commute to the office -Having a schedule that lines up with when you’re most productive -Taking a spin class in the middle of the day -Picking up your kids from school every afternoon -Living in different countries for several months at a time If this describes your idea of a great job, Pinterest is for you. Check out the 75 open roles in engineering: https://lnkd.in/gapDB_u3 At Pinterest, we hire smart people and trust them to do a good job. We don't track how often you badge into a building or how many days you show up in the office. We care about the business impact your code generates. We know that in person collaboration is useful, and we come in the office about 1/week. This isn't an unbreakable rule that you will get punished for violating. We want you to be your best you and to do your best work. We believe that flexibility enhances creativity and productivity. If you see something that calls to you, reach out and I am happy to answer questions.

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Want to tease something my team has been working on over at Buffer! The attached image isn't a mockup, but a screenshot of a live prototype of RSS feeds directly in Buffer! It's only available internally and still pretty rough at this point, but we'll have it available for user testing soon. With this enhancement, we hope to help Buffer users easily find new and engaging content to share with their audiences. What do you think? Will RSS feeds in Buffer help you create more content?

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We're in the pets phase of LLMs right now, but the cattle phase is coming and it'll change everything. Yes, again. What do you mean "pets" and "cattle"? Servers used to be our pets. We bought, named, cared for, and persisted them individually. If we wanted a new one, it was a big commitment. If one went down, it was a big loss. But then servers became cattle. Today we manage them as a group of commodity assets. We want one, we clone it. If one goes down, we replace it with another. This change delivered an era of distributed, high availability applications with limited downtime. Cheap storage, containers, cloud, clusters all met riding on top of Moore's law. And machine learning changed too. Computer vision was first. We went from small, neural networks running on CPUs via Matlab to a larger networks running in on GPUs via C++. AlexNet kicked off the deep learning revolution, eventually Transformers in NLP, and then ChatGPT. So, today we call our LLMs by name but this is just the start. There will be more LLMs variations than there are people on Earth.

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It’s eye-opening to see how AI model businesses are dealing with tight margins despite big investments. 🤯 Aidan Gomez’s comments about the “zero margin business” highlight the fierce competition and price cuts in the industry. 💸 With giants like OpenAI and Anthropic lowering prices to stay ahead, it’s a tough time for startups. The future of AI might depend on finding new ways to make these technologies profitable. 🚀 #AI #MachineLearning #TechTrends #Startups https://lnkd.in/ejkDu_wT

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Your ability to adapt to changing conditions will be your super power. Being overly adapted to existing conditions makes survival questionable.

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Hey everyone, I am an investor and advisor to Katanemo.... They are reinventing the infrastructure primitives for GenAI and launched Arch - https://lnkd.in/gCrbbkEV - an intelligent prompt gateway. Give the project a look on Github, and star the project if it resonates

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Check out this solution for building user authentication features into generative AI RAG applications!

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This resonates so much. No, you can't do it all, especially not at a startup. Since COVID I see so many people try to balance unaided parenting with full-time careers, and no, I don't see anyone doing it well. My kids are now 17, 13 and 10 and just now, when they trek to most of their activities on their own, and do their HW on their own, and cook their own meal or snack, we have finally let go of the outside help ( and this is with both parents working from home for last 5 years, outside of peak COVID lockdown, we had always relied on a designated childminder outside of school hours). Yes, working remotely does mean that I have more time and flexibility in my life, it means I can walk my kids to school sometimes, or have breakfast with them instead of rushing to the office, it means I can go and see their midweek concert at school, or be there to grab them from school on a sick day in 10 mins. But it also means that on EVERY day basis we all need clear boundaries, work hours, dedicated spaces that are not continuously invaded by children, or feelings of guilt that our children are unattended. One thing that a lot of the arrangments lack is transparency, being explicit with ourselves, our partners, our managers and colleagues on when we are making trade-offs. What helps is verbalising our plans, putting explicit blocks on calendars for pickups, doctor's appointments and school activities, letting others know when you will have periods of diminished focus due to a school holiday or a sick kid at home, and ruthlessly prioritising. Very few of us can claim to be at Julius Ceasar level of multi-tasking. Flexibility of remote work ≠ combining full time work with full time parenting

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I had a super hard time finding the right Lead Engineer/technical counterpart for me at my SaaS company. After going down the "hire a technical Co-Founder path" in the very early days of Because and having it not work out (having a co-founder is like a marriage and man it's not easy!)... After hiring older more seasoned technical leaders and having that also not work out... I finally hired the gem that is our Lead Engineer today, Marlin Jayasekera 🙏 He's in his late twenties and he's a better fit for our team than all the older more "seasoned" talent I had hired historically. That doesn't mean our entire team is Gen Z btw (we aren't ageist!) but I learned so many good lessons here I thought were worth sharing for anyone building out their team. In my opinion... 👨‍💻 Your first technical leader (or any early hire for that matter) should be someone who GSD (gets shit done 💩) rather than someone who dreams all day or just wants to "direct resources." 👵 Age doesn't define you. As a 27 year old CEO, I of course embody this value but it's been so cool to see other young leadership at Because quickly earning the respect and love from older peers around them. 🤝It's so important to make sure your early leadership team sees eye to eye with you. The relationship Marlin and I have built is healthy, respectful, and supportive. We know when to challenge each other but we almost always see eye to eye. That's way easier said than done! ✨ I completely trust him to make decisions. We come together once a week for sprint planning (1 week sprints) to set goals together and then I let him and the team go off and execute on those goals. The trust between us is key to let him and the engineering team be successful on their own. What wrong hires have you made that ultimately led you to the right one? ❤️👇

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Recently, Eric Ignasik and Michael Sols from The Software House asked me about my first steps as a VP of Technology at Habito. It's been a fun 8 months in a supportive environment with fantastic people! 😉 This interview discusses a few improvements ‌I made with a big emphasis on why servant leadership is important to me. Hope you’ll learn from it, ➡️ https://hubs.la/Q02Bw-Bv0 #softwaredevelopment #cto #softwaredelivery

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Team Circle shows (and tells) how devs can build onchain payment UX with $USDC and secure enterprise grade Programmable wallets. Real applications. Real use cases. Happening now. We are SO gonna make it!!

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