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 forwardLinksAdam 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 2024LinksAdam 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 VeilLinksAdam 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 candidatesLinksAdam 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 complianceLinksAdam 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) - MobilityLinksAdam 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 managementLinksAdam 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 suedLinksAdam on TwitterBen on TwitterTuple's /security pageY Combinator — Sales Agreement

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 bullets (11:11) - Tactic: Thinking from the perspective of "what could I demo" (11:43) - Example: How Tuple spins up standalone demos (13:00) - Feature flagging and continuous integration (14:19) - Example: Migrating the Tailwind UI website to React and Inertia (18:30) - Tactic: Derisking projects with "save points" (19:07) - The infamous "how to build an MVP" skateboard to car analogy (20:07) - Example: Shipping the Tailwind Connect event website (29:17) - Tactic: Don't be afraid of waste (31:41) - Tactic: Compare your work to what's in production, not your wildest dream (33:42) - Tactic: Do a great version of the simple solution (36:48) - Tactic: Make work in progress visible to avoid taking on too much (39:23) - Example: Designing the "Is it Tailwind" toolLinksAdam on TwitterBen on Twitter

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.Discuss this episode on Twitter →Timestamps(00:00) - “Why the fuck did I do this?” (06:20) - What is minimalist management? (10:56) - Should you need to be a trained life coach to be allowed to hire people? (16:12) - Using systems to provide career progression guidance (18:50) - What do David’s days usually look like? (27:13) - What are David’s responsibilities at Basecamp, and what are people counting on him for day-to-day? (29:38) - How David and Jason use their Shape Up framework to give people more responsibility at Basecamp (36:30) - Getting comfortable with being uncomfortable when giving people more responsibility (45:54) - Letting people go when they can't live up to the responsibility (47:14) - What systems do the 37signals team rely on that that haven't already been talked about publicly? (50:04) - Letting people make decisions you may have to correct and being comfortable correcting them (55:03) - Radical candor and redirecting feedback (01:00:55) - How to say no to opportunities and being willing to take risks (01:11:22) - Learning to stop worrying when you finally do succeedLinksAdamBenDavid

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 game-changer for the right type of business.Discuss this episode on Twitter →Timestamps(00:00) - Intro (00:14) - Why are we talking about this? (03:28) - Moving from package pricing to lifetime all-access pricing for Tailwind UI (06:03) - What about when you run out of new customers? (10:17) - "Everything You've Learned at MicroConf is Wrong" by Chad DeShon (13:33) - The myth of starting from zero every month (16:04) - Would Tailwind UI work as a subscription model? (18:09) - Characteristics of a lifetime-suitable product (20:50) - Subscription LTV vs. lifetime pricing (22:47) - Subscription friction and the death of the impulse purchase (25:42) - The brutality of churn in content businesses (27:21) - Why your lifetime price can actually be higher than your subscription LTV (29:01) - Ben's experience running Upcase at thoughtbot (32:42) - The hidden costs of the content treadmill (36:20) - Hitting a subscription plateau with Upcase (38:34) - Cookie Clicker game — how to make perceived value go up over time (42:31) - Why aspirational, impulsive purchases are more likely with lifetime deals (45:22) - Pricing decisions aren't forever (49:13) - Turning Build UI from a grind into an instant success by flipping the switch on pricing (54:17) - Using lifetime pricing to buy yourself flexibility and time to focusLinksAdam on TwitterBen on TwitterTailwind UI all-accessEverything You've Learned at MicroConf is Wrong, Chad DeShon's lighting talk at MicroConf Growth 2018Build UI, Sam and Ryan's new UI training site that recently switched to lifetime pricing

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. Timestamps00:00 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 What new advice is there since this talk?59:00 What about freemium?01:03:39 What happens next?01:08:58 Picking an idea that's compatible with the life you want to live01:12:16 Ideas for TailwindLinksAdamBenJason

“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?” Timestamps00:00 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 time30:57 Don't interview people, audition them35:38 We don't make movies to make money, we make money to make moviesLinksAdamBen

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 success22:06 Don't make your to-do list a chore list24:00 Declaring calendar bankruptcy27:43 Don't make promises future you has to pay for30:09 Make decisions quickly32:54 Making time for proofs of concept37:25 Bluffing in enterprise sales40:38 Doing things the way you want to, as much as you can afford toLinksAdamBen