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Software Misadventures

Ronak Nathani, Guang Yang

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A show about not just the technologies, but the people and stories behind them. In every episode, Ronak and Guang sit down with engineers, founders, and investors to chat about their paths, lessons they’ve learned and of course, the misadventures along the way.
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From creating one of the Python’s most influential libraries to co-founding Voltron Data, Wes joins the show to chat about why the book cover of the pandas book doesn’t feature a panda, open source pitfalls to avoid, the pros and cons of hiring engineers at a non-profit, and more. Segments: (00:02:50) Guang’s complaint about the pandas book cover (…
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From creating Envoy to co-founding bitdrift to reimagine mobile observability, Matt joins the show to chat about being told to simply “write some proxy in Python” in the early days of building Envoy, early influences from building “shrink wrap” software at Microsoft, the process of spinning bitdrift out of Lyft, and much more. Segments: (00:03:10) …
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From being a distinguished engineer at Sun Microsystems to co-founding Oxide Computer Company to build a new kind of server, Bryan joins the show to chat about being told that he’s on a suicide mission when starting Oxide, the moment he felt “I’m actually living HBO Silicon Valley”, and lessons from Sun. And much more. Chapters: (00:02:24) The Orig…
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From writing the first lines of Kafka over a Christmas break as a LinkedIn engineer to running a public company as the CEO of Confluent, Jay joins the show to chat about how he and his co-founders convinced investors to take a chance on their vision, what many engineers get wrong about communication, and why engineers can make great CEOs - even whe…
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If you’ve worked on data problems, you probably have heard of Airflow and Superset, two powerful tools that have cemented their place in the data ecosystem. Building successful open-source software is no easy feat, and even fewer engineers have done this back to back. In part 2 of the conversation, we talk about Max’s journey in open source. Segmen…
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If you’ve worked on data problems, you probably have heard of Airflow and Superset, two powerful tools that have cemented their place in the data ecosystem. Building successful open-source software is no easy feat, and even fewer engineers have done this back to back. In Part 1 of this conversation, we chat about how to adapt to the LLM-age as engi…
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Out of thousands of engineers at Uber, there’s only a handful of Distinguished Engineers and Joakim was one of them. In this conversation we chat about Why software engineering is a lot like a sausage factory. Considerations for leaving big tech for a startup. “How to beat the promo commitee”. How can one effectively shape engineering culture? “Men…
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We’re super excited to have Kelsey back on the show! Our last conversation was around his incredible career journey - from working at McDonald’s after school to starting his own computer store, to hacking on python infrastructure with the core developers, to meeting Satya Nadella for an interview. In part two of this conversation, we dive deep into…
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We’re super excited to have Kelsey back on the show! Our last conversation was around his incredible career journey - from working at McDonald’s after school to starting his own computer store, to hacking on python infrastructure with the core developers, to meeting Satya Nadella for an interview. In part one of this conversation, we dive deep into…
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As a self-described “gainfully unemployed data person”, Josh Wills is an angel investor and has worked on and led data teams at Slack, Cloudera, WeaveGrid and Google. We discuss: How to get started with angel investing without a ton of $$ Attributes that define great engineering managers What’s it like transitioning from management back to IC Chall…
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Known for coining the term “Data Scientist”, DJ is a renowned technologist with a diverse background spanning academia, industry, and government. Having led product teams at companies like RelateIQ and LinkedIn, DJ was appointed by President Obama to be the first U.S. Chief Data Scientist where his efforts led to the establishment of nearly 40 Chie…
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Erica is a former VP of Engineering at LinkedIn. Having almost dropped out of college, Erica’s journey in tech is a testament to her perseverance and dedication. In addition to leading engineering teams at LinkedIn, Erica founded WIT (Women In Tech) to empower women within the company as well as the broader tech community. We discuss: How to create…
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Mitchell co-founded HashiCorp in 2012 and created many important infrastructure tools, such as Terraform, Vagrant, Packer, and Consul. In addition to being a prolific engineer, Mitchell grew HashiCorp into a multi-billion-dollar public company. We discuss: How to structure large projects to avoid demotivation or burnout The "A.P.P.L.E" framework fo…
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After 17 years building SRE teams at Google and serving as the Site Lead for Engineering in Dublin, Dave joined Elastic as the Sr Director of Engineering and later VP of Engineering at Twilio. Following a recent career break, Dave now divides his time between coaching engineering leaders and consulting to help busy teams be more effective. In the h…
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At the personal request of Reid Hoffman to emerge from early retirement, David joined LinkedIn in 2009 during a period of rapid growth to help stabilize the chaos, cultivating a much-needed culture of “Site Up and Secure.” Before this, David served as SVP of Engineering and Operations at Yahoo!, overseeing their Search Marketing organization and th…
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Before joining CueIn last year as a Founding Data Scientist, Melissa was a Lead Data Scientist at Salesforce working on the Einstein Platform that focused on automating Data Science workflows. In this conversation we dive into Melissa’s unique journey, what to do in the face of increasing job automation and explore the latest developments in practi…
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What's it like to open source an internal project at a big tech company like LinkedIn? When should a company open source a project and what are the benefits and challenges that come along with it? If you want to open source an internal project, how should you go about advocating for it? Félix is a Principal Staff Engineer at LinkedIn where he works…
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Should engineers and product managers “stay in their lanes”? What big company habits should you keep vs unlearn when transitioning to working at a start-up? Could an ayahuasca retreat give you more clarity on your career goals? Ilya and Arnab join the show to share their journey quitting big tech to bootstrap a podcasting startup. Arnab and Ilya ar…
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What's "AI in a Box"? Pete Warden joins the show to share a new project he recently launched that encapulates Language Transcription/Translation and Question Answering capabilities into a wallet-sized board running locally without internet, as well as stories and learnings from building his new company, Useful Sensors, after 7 years of leading the …
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What does it mean to change the economics of software development? Nathan Marz joins the show to share how they reduced the cost of building Mastodon at Twitter-scale by 100X and the 10 years journey to build Rama, a new programming platform that made this feat possible. Nathan is the founder of Red Planet Labs. Prior to RPL, he led engineering for…
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Kelsey Hightower was a Distinguished Engineer at Google, where he worked on Google Cloud Platform. In this second part of the conversation, we focus on Kelsey’s retirement - the financial planning that enabled him to retire at 42, how he got started advising startups and his perspectives on compensation, turning down a substantial offer from Micros…
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Kelsey Hightower was a Distinguished Engineer at Google, where he worked on Google Cloud Platform. In this first part of the conversation, we delve into pivotal moments in Kelsey’s career journey ranging from buying his first car by working at mcdonald’s after school, to starting his own computer store that turned into a music studio after 6pm, to …
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Julie Amundson is a Sr Staff Software Engineer at Google working on Machine Learning Infrastructure. Prior to Google, she was the Director of Machine Learning Infrastructure at Netflix. Julie decided to take a career break last year when she was affected by mass layoffs. In this conversation, we talk to her about what it was like to find a job duri…
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Chris Pruett is the CTO and Co-founder of Jam - a new way to share and listen to bite-sized audio. Prior to Jam, Chris spent 9+ years at LinkedIn growing from an engineering manager to VP of Engineering. During his tenure at LinkedIn, he worked on almost all aspects of the app and towards the end, led an org of 500+ engineers working on Feed, Messa…
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Kailash is the CTO at Zerodha, the largest stock broker in India. In this conversation, we speak with him about absurdism - a philosophy that guides his personal and professional worldview. We discuss how he built Zerodha’s tech team, their team culture and how the team operates so efficiently while being so lean. We also discuss why Zerodha self-h…
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Michael Lynch is the founder of TinyPilot. After doing software engineering at Microsoft and Google for 7 years, Michael decided in 2018 to quit and start working for himself by building small software businesses. From years of negative profit to now building a $450K+ ARR hardware business, Michael joins the show to chat about what made him quit hi…
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Cory is currently a Solutions Engineer at Jeli.io and very well known in the community for his work on Observability. His career in observability began at Twitter where he managed the observability team and then he joined Stripe, where he created and led the observability team, this time around as a Principal Engineer. We talk to him about how he g…
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Ashwin is a Startup Partnership Lead at Stripe. From web development to co-founding a YC startup, to deep learning, Ashwin has a knack for picking up new skills extremely quickly. In this episode, we chat about the methods he employed to successfully make these transitions, learnings/tips from winning 30+ hackathons in a row, and what engineers can…
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Bruno Connelly is a VP of Engineering at LinkedIn. He leads the Site Engineering org responsible for LinkedIn's production infrastructure. He joins the show to talk about his journey in tech - from teaching himself how to code at a young age, building, maintaining and reverse engineering software as a teenager, building ISPs in the early part of hi…
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With 5+ years of experience building resilient systems at the Netflix scale, Lorin joins the show to chat about his favorite incident story, the path that led him to doing chaos engineering (and later away from it), and advocating for a dedicated analyst to talk to people after an incident. Throughout the conversation, Lorin shares his philosophy a…
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Spoons is the Co-founder and Chief Architect of Lightstep. He joins the show to talk about building systems at Google scale and various aspects that make Google a weird place than other companies. We talked about Spoons's journey of leaving Google and deciding to join Lightstep as a co-founder. We dig into the challenges during the early days of Li…
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Having led 100+ ML projects at Insight and built ML systems at Stripe scale, Emmanuel joins the show to chat about how to build useful ML products and what happens next when the model is in production. Throughout the conversation, Manu shares stories and advice on topics like the common mistakes people make when starting a new ML project, what’s si…
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Todd is a Sr Director of Engineering at Google where he leads Site Reliability Engineering teams for Machine Learning. Having recently presented on how ML breaks in production, by examining more than a decade of outage postmortems at Google, Todd joins the show to chat about why many ways that ML systems break in production have nothing to do with …
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Evan Estola (https://twitter.com/estola) is a Director of Engineering at Flatiron Health where he's leading software engineering teams focused on building Machine Learning products. Throughout this episode, Evan shares various stories when recommendation systems didn’t work as expected, like this one time when members saw mathematically worst recom…
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Uma is a VP of Engineering at Render. In this episode, she shared with us her insights on how to successfully manage infrastructure migrations. We discussed the importance of communicating the "why" behind a migration, identifying success metrics, creating a culture where migrations are identified as highly impactful projects and much more. Uma als…
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Charity Majors (https://twitter.com/mipsytipsy) is the co-founder and CTO of Honeycomb.io. Before this she worked at Facebook, Parse and Linden Lab on infrastructure and developer tools, and always seemed to wind up running the databases. She is the co-author of Database Reliability Engineering book and also has an amazing blog at charity.wtf. We l…
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Tammy Bryant Butow is a Principal SRE at Gremlin where she works on Chaos Engineering. In this episode, we discuss how her curiosity led her to the world of infrastructure engineering, an outage from her early days where a core switch took down half the datacenter, her experience running a disaster recovery test and how it taught her about the impo…
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Oliver Leaver-Smith, better known as Ols, is a Senior Devops Engineer at Sky Betting and Gaming. In this episode, we discuss how a seemingly simple monitoring change ended up taking down the entire site. We also talk about chaos and resilience engineering. We discuss how the team at Sky Betting and Gaming conducts fire drills (chaos engineering exe…
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Ryan Underwood is a Staff SRE and tech lead on the Helix and Zookeeper SRE team at LinkedIn. Prior to LinkedIn, he was an SRE at Machine Zone and Google. Apart from his regular responsibilities, Ryan’s interest and expertise include debugging production kernel, I/O and containerization issues. His opinion about not treating software as a black box …
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David is LinkedIn’s former SVP of Engineering and Operations. He came out of retirement to join LinkedIn in 2009 during a time of rapid growth. After 4 years at LinkedIn, he retired in 2013. Throughout his career, David has been in multiple leadership positions and has been recognized as one of the best Operations Executives. This was an extremely …
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In this episode, we speak with Julia Evans. Julia runs a programming zines business, called Wizard Zines (https://wizardzines.com/), where she creates comics about various programming concepts. She has been creating zines, when she was still a software engineer at Stripe. Her zines are extremely approachable and highly educational. In addition to c…
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In this episode, we speak with Kelsey Hightower who is currently a Principal Developer Advocate at Google and one of the most influential individuals in the Kubernetes community. He is also an author and a keynote speaker, with a knack for demystifying complex topics, doing live demos and enabling others to succeed. In this insightful conversation,…
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In this episode, Ronak, Austin and Guang share the origin story - who they are, what this podcast is about and why they are doing this. They've seen first hand how stressful it is when something breaks in production but also found it to be the best opportunity to learn about a system more deeply. They started this podcast to have in-depth conversat…
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