Revisiting the Tailwind Labs business model

In this episode, Adam and Ben sit down to reflect on how things went in 2024 in their business and personal lives and talk about their plans for 2025.

Adam and Ben are back on the mics after nine months to give an update on their lives.Timestamps(00:00) - Catching up (00:18) - Fitness update (18:13) - House updates (24:53) - Ben update (35:11) - Tailwind Labs update LinksAdam on XBen on X

Adam just wrapped up a big hiring project at Tailwind Labs, adding both a new engineer and a new designer to the team. In this episode he talks through the process with Justin Jackson, founder of Transistor, to compare notes and record what worked, what didn't, and how he will approach hiring in the future after going through this process.Timestamps(00:00) - Talking hiring with Justin Jackson from Transistor (01:05) - Adam's recent hiring project at Tailwind Labs (02:00) - Justin's history with hiring at Transistor (03:51) - How Transistor recruited their team (05:48) - Background on Adam's hiring project (16:54) - How to stand out as a candidate (26:29) - Who applied at Tailwind Labs — and who didn't (35:26) - Who ended up getting the offers (39:28) - The interview process (53:49) - Finding candidates, relationship building, and increasing luck surface area LinksJob postings for the roles at Tailwind LabsAdam on XBen on XJustin on X

After almost six years, Ben has stepped away from day-to-day work on Tuple and moved to its board. Friend of the pod Aaron Francis interviews Ben about the whole beautiful, complicated, enriching experience. As a treat, the boys dive into what's next for Aaron as well.

37signals have talked a lot about how they build new features for existing products using Shape Up, where they carefully hammer the scope to avoid letting anything ever drag on for more than six weeks. But there's not a lot of information out there about how they approach new product development, where it can take over a year to actually get the first version out the door. In this episode, Adam goes deep with Jason Fried about building and shipping their new HEY Calendar product, and whether or not Shape Up was part of that process.Timestamps(00:00) - Building the HEY Calendar with Jason Fried (01:04) - Why build a calendar (04:12) - How 37signals approach new product development (07:30) - Deciding on scope before launch (13:13) - Was there a six-week version of the HEY Calendar? (15:38) - Deciding how much time to spend on a new product (17:46) - Was the HEY Calendar built using Shape Up? (22:20) - Working on one feature at a time vs. in parallel (28:47) - What cycles look like at the early beginnings of a product (38:49) - How a project starts (45:46) - Increasing surface area vs. finishing things (47:57) - The development process for HEY Calendar going forward LinksAdam on TwitterBen on TwitterJason on TwitterJason's walkthrough of the HEY CalendarHEY Calendar

In this episode, Adam and Ben sit down to evaluate how things went in 2023 in their business and personal lives. The dudes share kind of a lot in this one! More personal flavor than usual. Lots about fitness, mental health, gathering, and rascally-ness. Timestamps(00:00) - Ben and Adam review 2023 (03:17) - Ben wants to be more of a rascal (07:58) - Health update (30:06) - Ben wants to prioritize creating "gatherings" (39:06) - Following your intuition (52:49) - Tailwind Labs business review (01:07:37) - Productivity (01:20:11) - 2023 lowlights — things to improve in 2024 LinksAdam on TwitterBen on Twitter

In this episode, Adam and Ben talk through the Tailwind Labs business model. Is Tailwind UI the best way for the company to make money? Or is there a different model where incentives are better aligned with growing the Tailwind CSS community as a whole? One potential model is offering a marketplace for templates and UI kits. Timestamps(00:00) - Black Friday (04:58) - Continuously improving stuff (12:50) - Tuple Rooms (16:15) - Revisiting the Tailwind Labs business model (27:28) - Brainstorming a Tailwind CSS marketplace (39:54) - Should Tailwind Labs build a SaaS? LinksAdam on TwitterBen on Twitter

In this episode, Adam and Ben catch up on recent events at Tailwind Labs and Tuple. Adam spoke at Rails World and the impromptu Tailwind CSS meetup in Amsterdam. Ben shares his learnings from some recent feature launches at Tuple.Timestamps(00:00) - Burpees (02:47) - Rails World + Tailwind CSS Amsterdam meetup (11:27) - Launching Tuple Triggers (25:57) - Tuple App Veil LinksAdam on TwitterBen on TwitterAdam Wathan - Tailwind CSS: It looks awful, and it works - Rails World 2023Tuple TriggersTuple App Veil

Adam wants to start the process of growing the team at Tailwind Labs, but knowing exactly who, when, and how to hire people (and have them actually work out) is a lot harder than expected. In this episode, he sits down with Jason Fried, founder and CEO of 37signals, to get all of Jason's best advice about hiring.Timestamps(00:00) - Talking hiring with Jason Fried (02:04) - Knowing when it's time to hire (04:57) - Grouping different responsibilities into single roles (11:49) - Example: Delegating some of Adam's responsibilities at Tailwind Labs (20:47) - Hiring to get more done vs. free up more time (23:58) - Stuff Jason has successfully delegated at 37signals (31:09) - Hard truths about hiring and growing a company (40:39) - Patrick Collison — Fast (44:13) - Anxiety about making bad hires (53:28) - Letting people go (54:55) - Jason's advice on making new hires successful (58:49) - Giving feedback (01:01:32) - Assessing good judgment (01:05:18) - Reviewing candidates LinksAdam on TwitterBen on TwitterJason on TwitterPatrick Collison — Fast

In this episode, Adam and Ben share some personal updates on lake houses, gym equipment, and luxury electric vehicles, and answer listener questions on topics like things they'd change when starting over, how to be more valuable as an employee, the point in their businesses that had the biggest impact on their happiness, and would they ever sell their companies.Discuss this episode on Twitter → Timestamps(00:00) - Personal updates (27:18) - "How come you've never released a trailer for Hackers Inc. on Art of Product?" (30:44) - "What's something you'd do differently if you were starting a business today?" (41:42) - "What would you do the same if you were starting a business today?" (45:24) - "What does your ideal employee look like?" (53:40) - "How often do you reflect on how far you've come?" (59:28) - "What was your biggest change in net happiness while running your businesses?" (01:10:56) - "Would you ever sell the company?" LinksAdam on TwitterBen on Twitter