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 wor

Ben steps away from Tuple

Apr 2nd, 2024 1h 11m

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'

Building the HEY Calendar with Jason Fried

Jan 17th, 2024 51m

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 t

Ben and Adam review 2023

Jan 14th, 2024 1h 36m

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 rasca

Revisiting the Tailwind Labs business model

Dec 4th, 2023 45m 55s

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

Launching features like products

Nov 27th, 2023 39m 54s

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:

Building the right team with Jason Fried

Oct 26th, 2023 1h 11m

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

Q&A: Starting over, the ideal employee, success and happiness, and selling the company

Sep 12th, 2023 1h 21m

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,

Predictable mistakes of the developer-turned-founder

Aug 30th, 2023 49m 3s

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 d

Losing 70 lbs, getting in shape, and 15-minute workouts

Aug 15th, 2023 59m 26s

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 an

Hiring is hard

Aug 1st, 2023 1h 6m

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 thr

Enterprise sales for reluctant founders

Jul 19th, 2023 1h

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 le

How to not suck at project management

Jul 7th, 2023 49m 18s

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 fi

Minimalist management with David Heinemeier Hansson

Jun 9th, 2023 1h 23m

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 sm

Lifetime pricing is underrated

Apr 21st, 2023 1h

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

Revisiting "The Ideal Bootstrapped Business" with Jason Cohen

Mar 25th, 2023 1h 24m

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 Desi

Running your business like a band

Mar 25th, 2023 36m 34s

“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

Lessons Learned in 2022-ish

Mar 25th, 2023 47m 36s

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 pr

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