
Software Misadventures
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.
Latest episodes

Sep 22, 2023 • 1h 33min
Nathan Marz - On changing the economics of building large-scale software with Rama - #23
Nathan Marz, founder of Red Planet Labs, shares how they reduced software development costs by 100X with Rama. Topics include suffering oriented programming, Rama's programming model, deployment & monitoring with Rama, building Twitter clone at scale, driving adoption, and fundraising.

26 snips
Aug 3, 2023 • 1h 31min
Kelsey Hightower - On retiring as Distinguished Engineer from Google at 42 (Part 2)
Former Google Distinguished Engineer, Kelsey Hightower, discusses financial planning for early retirement at 42, advising startups, turning down Microsoft, and meeting Satya Nadella. He reflects on valuing time, shifting priorities, overcoming ego, and career impact.

21 snips
Jul 24, 2023 • 1h 6min
Kelsey Hightower - On retiring as Distinguished Engineer from Google at 42 (Part 1)
Former Distinguished Engineer at Google Cloud Platform, Kelsey Hightower, shares pivotal career moments from working at McDonald's to becoming a tech entrepreneur. He discusses skill acquisition, open source projects, navigating corporate dynamics, and team trust, showcasing his journey from self-study to Google System Administrator interview success.

Jun 27, 2023 • 57min
Julie Amundson - Career breaks, job search amidst hiring freezes, positioning yourself and much more - #20
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 during hiring freezes, what it was like to position herself in this market, whether the interviewers cared about the career break she took and how the career break changed her perspective towards work and life.

Jun 3, 2022 • 1h 20min
Chris Pruett - On deciding to leave LinkedIn and co-founding Jam, values based decision making and compassionate leadership - #19
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, Messaging, Identity and Search. In this episode, we discuss how he made the decision to leave his leadership position at LinkedIn and co-found Jam. We also spoke about his time at LinkedIn and how he developed the practice to make value based decisions both in professional and personal life.

Mar 25, 2022 • 8min
Software Misadventures Update and Plans for 2022
Short episode about reflections on the past year and plans for 2022.

Feb 25, 2022 • 1h 38min
Kailash Nadh - On being an absurdist and building the tech team at Zerodha, India's largest stock broker - #18
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-hosts all of their tech stack, what they look for when hiring engineers and how their systems scaled when the user base grew from 2 to 8 million in 18 months.

Jan 14, 2022 • 1h 47min
Michael Lynch - On quitting google for indie hacking, bootstrapping to $450K+ ARR in public, writing personal retrospectives and more - #17
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 his cushy job at Google, how he builds in public with monthly retrospectives, what he has learned over the 3 years indie hacking and much more.

Nov 12, 2021 • 1h 24min
Cory Watson - Leading observability teams at Twitter & Stripe, how to succeed in a new org, effective ways to advocate for your team and more - #16
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 got his start in customer support and the role it played in the later part of his career. We discuss his time at Twitter where there was a power outage in the data center on the day he joined and how once he had to stay up all night dealing with file handle leaks. We also discuss how he created and led the observability team at Stripe as an individual contributor, how one can succeed in a new org, how to navigate information asymmetry in the workplace, what are some effective ways to advocate for your team and how we all are just humans trying to get stuff done.

Oct 12, 2021 • 1h 14min
Ashwin Kumar - On learning new things by breaking them down, the secret to winning >$100k from hackathons, the art of storytelling, and much more - #15
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 gain from better story-telling.
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