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The boys are back and Ben has been coding! Amp vs Claude Code vs Codex. Clawdbot. The Agentification Era.  Sorry about Ben's audio. We think it was Riverside's fault, sadly.

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

So many developers (your podcast hosts included) make the same mistakes when trying to turn an idea into a business for the first time. In this episode, Ben and Adam talk through a bunch of these mistakes, why they matter, and what you should do to avoid them. Discuss this episode on Twitter → Timestamps (00:00) - Ben's Laracon talk "Predictable Mistakes of the Developer-Turned-Founder" (02:57) - Mistake: Starting with SaaS (15:21) - Mistake: Selling to consumers (17:40) - Mistake: Selling to struggling businesses (24:24) - Mistake: Not pre-selling your product (25:52) - Mistake: Assuming people are rational (26:58) - Mistake: Not choosing a customer you like (28:05) - Mistake: Being comfortable with your pricing (33:37) - Mistake: Raising VC (40:09) - Mistake: Overfocusing on legal and compliance LinksAdam on TwitterBen on Twitter"Predictable Mistakes of the Developer-Turned-Founder" on YouTube

Last year, Adam got very serious about losing weight and getting in shape and lost 70 pounds, getting to about 12% body fat and maintaining enough strength to still bench 315. In this episode, Adam and Ben talk about Adam's weight loss story and all the specific tips and tactics he used to overcome a lifetime of bad eating habits, change his relationship with food, and kick ass in the gym. Discuss this episode on Twitter → Timestamps (00:00) - Introduction (01:16) - Adam's weight loss story (03:27) - Working with an accountability coach (10:17) - How to eat less food (22:11) - Macros aren't your biggest problem (24:27) - Tracking what you eat (30:20) - Protein shakes (33:20) - A day of eating in Adam's life (37:35) - Adam's training background (41:37) - Adam's current training routine (47:17) - Using a training partner or personal trainer for accountability (48:37) - Adam's morning routine (50:30) - Training to build muscle vs training to maintain (53:53) - Mobility LinksAdam on TwitterBen on TwitterMyBodyTutorLose It!

When you're running a small company, hiring is simultaneously your highest leverage opportunity and the scariest thing ever. In this episode, Adam and Ben share some lessons learned, how they think about hiring for their teams now, and talk through some of the things they're still trying to figure out how to get right. Discuss this episode on Twitter → Timestamps (00:00) - Hiring (02:02) - Why hire at all? (06:41) - Avoiding hiring altogether (11:44) - Vetting people (24:45) - Finding people (36:22) - How Ben got recruited at Thoughtbot (37:53) - Evaluating hires (43:23) - Fears and anxieties around hiring (50:50) - Unfair hiring advantages (57:36) - Levels of management LinksAdam on TwitterBen on Twitter

Enterprise sales gets a bad rap amongst indie founders, but at Tuple it's become an important part of their business model. In this episode, Ben shares all his tips and tricks on how to sell to enterprise customers as a small startup without letting it slow you down. Discuss this episode on Twitter → Timestamps (00:00) - Ben's notes on enterprise sales (02:58) - Ben's first time (04:56) - Tactic: Build a product that can grow bottom-up (07:12) - Tactic: Ask buyers to answer their own questions (08:34) - Tactic: Say no to more than you think (16:11) - Tactic: Your pricing should make you uncomfortable (25:38) - Tactic: Charge more for SAML single sign-on (27:50) - Tactic: Don't sign something without charging a lot (28:34) - Tactic: Put an expiration date on your quotes (29:12) - Tactic: Dodge pricing pushback with quarterly payments (31:06) - Tactic: Make sure you lose some deals because of price (33:26) - How procurement works (37:54) - How important is enterprise sales for Tuple? (47:59) - Tactic: Ask procurement, "what helps this deal get done faster" (49:49) - Tactic: Have a /security page on your website (53:07) - Tactic: Use Y Combinator's sales agreement template (55:47) - Tactic: You probably won't be sued LinksAdam on TwitterBen on TwitterTuple's /security pageY Combinator — Sales Agreement