It Shipped That Way

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.