Milun Tesovic, founder of Metrolyrics, Cmd, and Gitalytics – and now Parter at Expa – shares lessons learned building startups. We talk about building the largest lyrics site in the world, turning organizational dysfunction into startup ideas, solving problems without making people change their behaviour, getting acquired by Github a month after launch, making early hires on a product team, and how to get a great domain with one weird trick.<ul> <li><a href="https://expa.com/">expa.com</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

The Browser Company’s Head Of Engineering, Dolapo Falola, shares lessons from Google, Facebook, and Slack, and how they’ve informed his leadership of the team building Arc. He shares about the rush to launch Stories at Meta, reinventing the browser with Arc, finding work that energizes people vs. finding people energized by the work, “working out loud” for velocity, the challenge of bringing Arc to Windows, rewarding complexity vs. business impact, and playing the long game to hire exceptional talent.<ul> <li><a href="https://dolapo.io/">dolapo.io</a></li> <li><a href="https://arc.net/">The Arc Browser</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Paul Lambert, CEO and founder of Quilt and former Director at Google’s Area 120, joins Allen to talk society-scale problems, why searching for product-market fit is overrated, the power of building a better mousetrap, why the “internal incubator” model usually fails, how modern hardware startups iterate rapidly, and why different cities lend themselves to different startups.<ul> <li><a href="https://www.quilt.com/">Quilt</a></li> <li><a href="https://medium.com/@prlambert/four-rules-for-starting-a-startup-7f54d2e0e20c#.uc86i65bb">Paul’s Four Rules for Starting a Startup</a></li> <li><a href="https://www.linkedin.com/in/paulrolandlambert/">Paul Lambert</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Dennis Pilarinos, founder of Buddybuild and now Unblocked (and former Director at Microsoft, Amazon, and Apple) shares what he’s learned about product leadership. We talk about why you should build a product that is hard, how providing support is key to product culture, staying deeply curious about what’s not working, cutting down recurring meetings, and how startups with distribution outcompete the giants.<ul> <li><a href="https://twitter.com/dennispilarinos">Dennis on Twitter</a></li> <li>Get <a href="https://getunblocked.com/">Unblocked</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Honeycomb.io co-founder and CTO Charity Majors joins Allen to share what she’s learned growing Honeycomb from idea to 170-person distributed company, including what goes into being a good manager beyond supporting your reports, how to build a team that feels supportive and safe while still keeping boundaries and limits, systems thinking for teams and cultures, the difference between generic company values and ones that take a stand, and why having a healthy culture is more important than having a novel one.<ul> <li>Charity’s blog, <a href="https://charity.wtf/">charity.wtf</a></li> <li>The <a href="https://www.honeycomb.io/blog">Honeycomb.io engineering blog</a></li> <li>Emily Nakashima on the Honeycomb blog: <a href="https://www.honeycomb.io/blog/becoming-vp-of-engineering-pt1">On Becoming a VP of Engineering</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Ada co-founder David Hariri joins Allen to talk about an audacious product discovery process that kicked off a 250-employee startup, limitations of hand-scripted workflows, strengths and weaknesses of LLM techniques like code execution, RAG, and function calling, and how support automation may create whole new business models.<ul> <li><a href="https://www.ada.cx/">Ada Support</a></li> <li><a href="https://dhariri.com/">David Hariri</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Michael Lopp, aka Rands, joins Allen to talk about the fundamental need for growth, finding your team’s core motivations, the value of writing for developing clear thinking, the joys and perils of writing a book, the art of a compelling presentation, habits for editing and refining writing, and fostering clarity of responsibility – and curiosity – on your team.<ul> <li><a href="https://randsinrepose.com/">Rands in Repose</a></li> <li><a href="https://randsinrepose.com/the-important-thing/">The Important Thing</a></li> <li><a href="https://randsinrepose.com/welcome-to-rands-leadership-slack/">Rands Leadership Slack</a></li> <li><a href="https://www.oreilly.com/library/view/the-software-developers/9781098116668/">The Software Developer’s Career Handbook</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Tiffany Conroy, former VP of Engineering at SoundCloud, shares what she’s learned about where new engineering managers stumble and how to support them, considering whether you want to be a manager at all, the value of explicitly asking those around you what success means, the power of having the confidence to say “I don’t know”, coaching managers through their first case of underperformance, how rigid role definitions hold back folks that perform both product and engineering work, the power of the Six Thinking Hats for making intense decisions, and the cultural responsibilities of senior leadership.<ul> <li><a href="https://hachyderm.io/@theophani">Tiffany Conroy – theophani on Mastodon</a></li> <li><a href="https://www.golaminar.de/">Laminar</a></li> <li><a href="https://www.youtube.com/watch?v=LGDryOB8gZc">Tiffany’s talk on Workplace Confidence</a></li> <li><a href="https://en.wikipedia.org/wiki/Six_Thinking_Hats">Six Thinking Hats</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Adam Lisagor, Founder of Sandwich Video, shares what he’s learned about the nature of storytelling, about how to zoom out to tell the story of your product, understanding the emotional valence of our work, when pre-visualization and storyboarding does and doesn’t pay off, spotting great talent, the value of making pretty good decisions quickly, learning how to let go (a little bit) as a founder, execution-centric leadership vs. results-centric leadership, what kinds of products he likes to invest in, and making people glad to have worked with you.<ul> <li><a href="https://sandwich.co/">Sandwich Video</a></li> <li><a href="https://sandwich.co/clients/breadwinner/">The Breadwinner Fellowship</a></li> <li><a href="http://adamlisagor.com/">adamlisagor.com</a></li> <li><a href="https://masto.sndw.ch/@adamlisagor">Adam Lisagor on Mastodon</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Aliya Marder, Co-Founder of Ridwell, joins us to share what she’s learned about the people-service mindset for product work, the demands of running a startup with a real-world footprint, the power of a higher mission for rallying a company, doing more with a smaller team, the pathologies of product backlogs, strategic communication past 150 employees, and the challenge of delegating for detail-oriented leaders.<ul> <li><a href="https://www.ridwell.com/">Ridwell</a></li> <li><a href="https://www.linkedin.com/in/aliyamarder/">Aliya’s LinkedIn</a></li> <li><a href="https://allenpike.com/2023/do-something-so-we-can-change-it">Do Something, So We Can Change It!</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Ian MacKinnon, CTO of Later and Mavrck, shares lessons learned building Later from founding to success to acquisition – and from the startups that weren’t so fortunate. We discuss early engineering practices that paid off, approaches for moving fast and tolerance for breaking (small) things in that pursuit, the pros and cons of PaaS platforms like Heroku, the insurmountability of building the wrong thing, the virtues of boring tech stacks, and Later’s successes using GPT-4 to migrate and modernize legacy codebases.<ul> <li><a href="https://later.com/">Later</a> and <a href="https://www.mavrck.co/">Mavrck</a></li> <li>Ian on <a href="https://twitter.com/imackinn">Twitter</a> and <a href="https://www.threads.net/@imack">Threads</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Lynsey Thornton shares what she learned helping Shopify grow almost 100x as GM of Core Product, VP of UX, and more. We review some common challenges companies hit as they scale, how to identify hires that have high growth potential, how different personalities contribute to team effectiveness, how to design an org for maximum impact, user research as a driver of strategic outcomes rather than checkbox-checking, and how to level up as a leader.<ul> <li><a href="https://www.backboneangels.com/">Backbone Angels</a></li> <li><a href="https://www.linkedin.com/in/lynseythornton/">Lynsey on LinkedIn</a></li> <li><a href="https://larahogan.me/blog/questions-for-biceps-core-needs/">Lara Hogan on the BICEPS framework</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Cate Huston joins to talk about her new book, The Engineering Leader. She shares why she wrote a book, leadership problems endemic to fast-growing organizations, why career growth is more than promotions, coachability, levelling up your hiring pipeline, how hiring “bars” can go wrong, and why energy management matters more than time management.<ul> <li><a href="https://www.itshipped.fm/episodes/4">It Shipped Ep. 4 with Cate Huston</a></li> <li>Cate’s new book, <a href="https://www.oreilly.com/library/view/the-engineering-leader/9781098154059/">The Engineering Leader</a></li> <li><a href="http://cate.blog">cate.blog</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Bruce Alderson, Senior Product Manager at Mailchimp, shares what he’s learned in 20 years as a CTO, engineering leader, and product manager. We discuss the role of multi-disciplinarians in large orgs, engineering leadership vs. product leadership, the value of repeating yourself, finding the team members who can help share context across your company, what it means to stay focused as you scale, and being effective in the face of great uncertainty.<ul> <li><a href="https://mas.to/@robotpony/">Bruce on Mastodon</a></li> <li><a href="https://twitter.com/robotpony/">Bruce on Twitter</a></li> <li><a href="https://warpedvisions.org">warpedvisions.org</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Steve Gill, Slack’s Director of DevRel Engineering, digs in to the craft of building great APIs for developers. We discuss the power of open source for informing platform work, building platforms that developers will actually use, the tricky issues around building and supporting SDKs, the concept of “raccooning” at Slack, how Slack’s new composable apps enable a whole new category of app, and the importance of saying “no” when a new feature isn’t working out.<ul> <li><a href="https://api.slack.com/">Slack’s new API</a></li> <li><a href="https://twitter.com/stevesgill">stevesgill on Twitter</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Nik Pinski, Principal Engineer at AWS, shares how AWS is organized for autonomy and customer-centric product development, dealing with millions of events per second, and how Staff and Principal Engineer career tracks work across different software organizations.<ul> <li><a href="https://staffeng.com/">staffeng.com</a></li> <li><a href="https://levels.fyi">levels.fyi</a></li> <li><a href="https://aws.amazon.com/eventbridge/">Amazon EventBridge</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Kyle Peatt, former Head of Design at Shopify, shares lessons he learned helping rapidly scale Shopify’s UX team from 30 folks to 450. We talk about effective triads of product, design, and engineering leadership; building a UX organization without becoming a matrix org; the concept of UX Leads that manage folks from front-end engineering through design and content strategy; what makes a Staff Designer; and the importance of having an opinion in design leadership.<ul> <li><a href="https://kylepeatt.com/">kylepeatt.com</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Ian Wong, co-founder of Opendoor, shares what he’s learned about machine learning and data science in his work as CTO of Opendoor and helping detect fraud at Square. We talk about the differences between descriptive and predictive ML, approaches to human-in-the-loop prediction, setting up a data science org to deliver real business impact, why so many internal tooling projects fail, and how leaders should be dividing their attention between top-level strategy and the details that really matter.<ul> <li><a href="https://twitter.com/ihat">@ihat on Twitter</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Netflix’s Arik Devens shares what he’s learned about architecting mobile apps with many millions of users, building from early adventures at Netscape and Palm up to architectural roles at Fitbit and Netflix. We talk about Netflix’s culture of small, high-trust teams; some of the pathologies of very large engineering teams; how to sell new architectural patterns to a team working on a large existing codebase; and the challenges of A/B testing hundreds of millions of users.<ul> <li><a href="https://jobs.netflix.com/culture">Netflix’s famed culture doc</a></li> <li><a href="http://danieltiger.com/">danieltiger.com, Arik’s website</a></li> <li><a href="https://funfact.fm">Fun Fact</a>, Allen and Arik’s podcast about facts</li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Jaycee Day, a seasoned designer having worked at GitHub and Blinkist, shares what she learned designing a now world-famous app onboarding flow. We talk about onboarding flows, subscription and trial mechanics in apps, the tensions between ethics and short-term profiteering, the business model of mobile games, and A/B testing.<ul> <li> <p>Jaycee’s website, <a href="https://jayceeday.com/">jayceeday.com</a></p> </li> <li> <p>Jaycee’s original article about her onboarding workflow, <a href="https://uxplanet.org/how-solving-our-biggest-customer-complaint-at-blinkist-led-to-a-23-increase-in-conversion-b60ad514134b">How Solving Our Biggest Customer Complaint at Blinkist Led to a 23% Increase in Conversion</a></p> </li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Cate Huston shares what she’s learned leading engineering teams at DuckDuckGo, Automattic, and Google. We talk about the challenges of hiring directors, what makes DuckDuckGo weird, supporting team happiness vs. team effectiveness, the quagmire of trying to measure team velocity, and the tradeoffs inherent in cross-platform app development.<ul> <li><a href="https://cate.blog/">Cate’s blog</a></li> <li><a href="https://cate.blog/2022/04/25/escaping-the-house-elf-management-trap/">Cate’s article on servant leadership</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Shawn Jansepar, Director of Engineering at Khan Academy, shares what he’s learned about keeping product teams engaged, effective engineering practices and how to teach them, and building trust.<ul> <li><a href="https://www.linkedin.com/in/jansepar/">Shawn Jansepar on LinkedIn</a></li> <li><a href="https://www.khanacademy.org/">Khan Academy</a></li> <li><a href="https://developer.squareup.com/blog/squares-growth-framework-for-engineers-and-engineering-managers/">Square’s Engineering Growth Framework</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Polly Allen, former Principal Product Manager on Amazon Alexa, shares what she’s learned about the challenging world of building products for voice and AI, as well the roles of data-driven decision-making and computing science education in product leadership.<ul> <li>Polly is <a href="https://twitter.com/yukonpolly">@yukonpolly on Twitter</a> and is also <a href="https://www.linkedin.com/in/pollymallen/">on LinkedIn</a></li> <li>Polly’s business, <a href="https://www.aicareerboost.com/">AI Career Boost</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Johnny Rodgers, one of Slack’s founding engineers, shares stories and lessons from building Slack. He shares Slack’s origin, the art of extreme responsiveness to customer feedback, how features like threads and reacji came together, Slack’s positioning and north star, product-led growth as a path to building startups, and how to have an outsized impact in a scaling organization.<ul> <li><a href="https://johnnyrodgers.is/">johnnyrodgers.is</a></li> <li><a href="https://buildingslack.com/">buildingslack.com</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Brad Ellis pulls from his experience designing for Square, Lyft, and many other products to share what he’s learned about the incredible value of user testing, scaling product design across a large org, and how to make great experiences instead of shipping your org chart. Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Teresa Torres, author of Continuous Discovery Habits, joins to share lessons from her popular and acclaimed book. We talk about the benefits of constantly talking to customers, why it can be worth seeking delight rather than strictly building products in terms of problems, how to avoid choosing perverse outcomes and metrics, and how to get the truth from customers – despite their aspirational overconfidence.<ul> <li><a href="https://www.producttalk.org/">ProductTalk.org</a></li> <li><a href="https://www.linkedin.com/in/teresatorres/">Teresa on LinkedIn</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Luke Hutscal, Principal Engineer at Clio – formerly of Shopify and Testflight – joins to talk about finding ways to learn rapidly, the downsides of a mercenary mindset, spending time with people who intimidate you, building a coaching village, making wrong things look wrong, choosing boring technology, resume-driven development, and putting in the reps to get great at hiring.<ul> <li><a href="http://lukehutscal.com/">Luke Hutscal</a></li> <li><a href="https://mcfunley.com/choose-boring-technology">Choose boring technology</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

James Clift, Founder and CEO of Durable and VisualCV, joins us to talk about helping folks build great businesses, staying long-term optimistic yet short-term pessimistic, choosing between exciting ideas vs. clearly profitable ones, the distraction of “fake work”, getting good at rapidly trying and killing ideas, lessons learned from two years of building on LLMs, and the longevity of non-chat workflows.<ul> <li><a href="https://twitter.com/jamesclift">@jamesclift on Twitter</a></li> <li><a href="https://durable.co/">Durable</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Eric Amodio, creator of GitLens, GitKraken CTO, and former Principal Engineer on VS Code, joins us to talk about founding products by scratching your own itch, building GitLens from an idea to tens of millions of users, the audacity of charging for software, the origins of github.dev and Copilot at Microsoft, LLMs as a new layer of abstraction for developers, and how GitKraken is helping engineers understand large codebases faster.<ul> <li><a href="https://www.gitkraken.com/">GitKraken</a></li> <li><a href="https://marketplace.visualstudio.com/items?itemName=eamodio.gitlens">GitLens</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Merci Grace, CEO and co-founder of Panobi, and former partner at Lightspeed Ventures and first Head of Growth at Slack, shares lessons about growth as a discipline, pitfalls of fundraising and her “Marauder’s Map” to raising capital, best practices for starting and scaling growth teams, and her vision for making metrics and growth tooling far better.<ul> <li><a href="https://panobi.com/">Panobi</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Ian Crosby, founding CEO of Bench and now Teal, talks building Bench from zero to hundreds, how vertical SaaS is transforming SMB startups, what it really takes to become highly profitable, why Teal hires for “boring competence”, paying highly for top talent, the psychology of firing, and the limits of culture docs.<ul> <li><a href="https://teal.dev/">teal.dev</a></li> <li><a href="https://www.linkedin.com/in/iwcrosby/">Ian Crosby on LinkedIn</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Lorilyn McCue, head of AI product at Superhuman, joins to share what she’s learned building LLM-powered products. She talks about how Superhuman executes on shipping delightful software, how to pursue both attention to detail and rapid iteration, optimizing your roadmap for learning, questions that are surprisingly easy (and hard) for LLMs, evaluation and testing of AI-powered features, and ruthlessly prioritizing the user.<ul> <li>The <a href="https://blog.superhuman.com/">Superhuman Blog</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Wealthsimple Co-Founder and CPO Brett Huneycutt shares lessons from building a 1500-person company recently valued at $10B. He relates the underlying wisdom of “Launch now”, how early dogfooding and short cycle times increase both speed and quality, attention to detail as a brand promise, where product decisions should be taste-driven vs. data-driven, and how to hire people you would want to work for.<ul> <li><a href="https://www.youtube.com/live/zokVUFCJzMo">Wealthsimple Presents: The End of Banking</a> on YouTube</li> <li><a href="https://x.com/bretthuneycutt">Brett Huneycutt on X</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Zapier’s first PM and now VP of Product Chris Geoghegan joins us to discuss the relationship between deterministic and LLM-powered automations, scaling a transparent and fully-remote company from millions in revenue to hundreds of millions, whether PM roles are becoming more or less important today, disrupting yourself before anybody else does, and the value of knowing SQL.<ul> <li><a href="https://www.linkedin.com/in/chrisgeoghegan/">Chris Geoghegan</a> on LinkedIn</li> <li><a href="https://maven.com/p/0a96cb/cursor-isn-t-just-for-coding-how-ai-native-p-ms-work">Cursor for PMs course</a> from Tal Raviv</li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.

Jane App Co-Founder & Co-CEO Trevor Johnston shares lessons from building a vertical SaaS that now serves hundreds of thousands of clinicians worldwide. We discuss the geometric power of referrals, obsessing over churn, turning your customers into your salespeople, scaling product engineering past Dunbar’s number, transcending a Rails monolith, and finding the fun in 6 hours of Zoom meetings.<ul> <li><a href="https://jane.app">Jane App</a></li> </ul> Have feedback for the show? Send an email or message to Allen any time. It Shipped That Way is supported by Steamclock Software and Forestwalk Labs.