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...

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...

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) -...

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 Links Adam on Twitter Ben on Twitter Adam Wathan - Tailwind CSS: It looks awful, and it works - Rails World 2023 Tuple...

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:...

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...

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:...

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...

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...

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...

Most people are way too comfortable letting a project run for 12 weeks before ever getting it into a shippable state. In this episode, Adam and Ben share the strategies they use to make sure the projects they work on are shippable within the first few days, and stay shippable until the decision is made to finally cut the release. Discuss this episode on Twitter → Timestamps (00:00) - If it's not done, it's not done (03:54) - Example: Building an example app for Catalyst UI (07:01) - Tracer...

After over 20 years in business and despite being responsible for a larger-than-ever team, David still finds plenty of time to get his hands in the code and build new products himself. We run significantly younger companies and significantly smaller teams and even we can't seem to find the space to do that, so we talked to DHH about how he makes it possible. Timestamps (00:00) - “Why the f**k did I do this?” (06:20) - What is minimalist management? (10:56) - Should you need to be a trained...

Last summer, Tailwind UI moved from selling individual content packages and upsells to a one-time purchase, lifetime access pricing model. Since then, the business has doubled. Having seen this in action, Adam recently convinced his friends Sam and Ryan to try lifetime pricing for their product Build UI, and the results are starting to come in. In this episode, Adam and Ben dive deep into the world of lifetime pricing, why it's not something to be afraid of, and how it can be an absolute...

Jason Cohen’s talk “Designing the Ideal Bootstrapped Business” from 2013 is a classic in the bootstrapper canon. In this episode, Jason joins Adam and Ben to see how the talk holds up a decade after its creation. Timestamps 00:00 Intro00:27 Designing the ideal bootstrapped business06:53 Recurring revenue vs one-off sales13:30 Getting all the LTV up front18:31 Product validation24:56 Creating a cash machine26:05 Where does growth come from?41:25 Annual prepays46:41 Increasing your prices51:56...

“How come Dave Grohl is still playing guitar and writing songs and singing but I'm filling out DMCA takedown notices, answering customer support emails and responding to GitHub issues?” Timestamps 00:00 Intro03:05 Bringing on a band manager07:34 Why the band metaphor works11:54 Make things for your fans, not for your critics14:49 Always do the things you want to do18:04 Turning over your rep over time19:33 A band needs a frontman22:14 Showing behind the scenes25:23 Doing one thing at a...

Ben Orenstein (Tuple) and Adam Wathan (Tailwind CSS) are back on the mics. Today they reflect on 2022 and lessons they’ve learned. Ben has some thoughts on delegation, priorities and enterprise sales, while Adam explains how he made time for proof of concepts and has figured a way to actually follow his to-do list. Timestamps00:00 Intro02:11 Setting priorities05:11 Shaping up08:27 Don't allocate everyone to every project15:46 Top down management17:13 Delegation gone wrong can still be a...