Best Adam Wathan Podcasts (2025)

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An update from Justin and Jon 53:38

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28d ago53:38

53:38

Justin and Jon reconnect after a two-year podcasting hiatus. What's happened since their last episode? Lots! They talk about big changes in their personal lives, and then move on to how they're thinking about Transistor as a business. These discuss burnout and motivation, the evolution of the podcasting industry, the pressure of being a leader, and…

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153: DHH – Omarchy and Designing Your Own OS on Arch Linux 1:16:25

2M ago1:16:25

1:16:25

I talk to DHH about Omarchy, the carefully curated distribution of Arch Linux he's been refining for the last few months. We talk about stuff like: How did he discover Arch + Hyprland in the first place? What even is Arch, what even is Hyprland, and how the fuck do you make the mouse show up in Linux? Should you really be afraid of trying to mainta…

1
"Justin, I built a SaaS!" 1:30:43

4M ago1:30:43

1:30:43

Harris Kenny was a long-time listener of the podcast, and dreamed about building his own software product. After multiple attempts, over 5 years, he finally did it. How? He shares his experiences transitioning from a corporate job to entrepreneurship. He also discusses the challenges of user engagement, the exploration of various SaaS ideas, and th…

1
2024 year in review and plans for 2025 1:28:22

9M ago1:28:22

1:28:22

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.By Ben Orenstein and Adam Wathan

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Giuuunta! Motivating yourself when you're not in startup mode 1:11:56

10M ago1:11:56

1:11:56

Bootstrapping a business is like getting a plane to lift off the ground. But what do you do once the plane is in the air? Dave Giunta and Justin Jackson recorded a recent phone call about maintaining motivation after the initial startup phase. How does founder energy shift once you've achieved your early goals? Dave prods Justin to find new sources…

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Catching up 45:11

1y ago45:11

45:11

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 Links Adam on X Ben on XBy Ben Orenstein and Adam Wathan

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Adam Wathan, Creator of Tailwind CSS 1:00:06

1+ y ago1:00:06

1:00:06

Ben and Adam Wathan cover the development and reimagining of Tailwind CSS, focusing on the release of Tailwind 4.0. They delve into the motivation behind the rewrite, the challenges faced, and the approach to maintaining backward compatibility. The conversation covers topics related to software versioning, open-source maintenance, backward compatib…

1
Adam Wathan: how small startups hire employees (Tailwind CSS) 1:34:42

1+ y ago1:34:42

1:34:42

How do founders of small bootstrapped companies hire new employees? Adam Wathan got over 1600 people who applied for two new roles at Tailwind Labs (a small team of six people). They ended up hiring two people, but neither of them actually applied. This wasn't how Adam expected (or hoped) this process would go. There were lots of surprising takeawa…

1
Matt Swanson, CTO at Arrows 45:25

1+ y ago45:25

45:25

Ben and Matt discuss the role of a product engineer and Matt's journey as a content creator. Matt shares his experience working at a consulting agency and how it shaped his perspective on engineering. They also discuss the benefits of working in-person and the importance of the quality of coworkers. Matt reflects on his motivation for content creat…

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Hiring for tiny teams with Justin Jackson 1:39:02

1+ y ago1:39:02

1:39:02

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. Timestam…

1
Derrick Reimer, Founder of SavvyCal 45:48

1+ y ago45:48

45:48

In this conversation, Ben and Derrick discuss the challenges of growing a business and the decision to target specific market segments. They explore the trade-offs between serving a broad audience and focusing on a niche market. They also discuss the technical choices and architectural decisions in building a product, with Derrick sharing his posit…

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Thorsten Ball, Software Engineer at Zed 1:12:58

1+ y ago1:12:58

1:12:58

In this episode, Ben chats with Thorsten Ball. This conversation fits neatly into two halves - in the first, Ben and Thorsten go deep on how to differentiate yourself, work in public, and make it easy for people to hire you. In the second part of the conversation, they talk more specifically about Zed, why it matters, and how it’s being built. Link…

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Ben steps away from Tuple 1:11:22

1+ y ago1:11:22

1:11:22

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.By Ben Orenstein and Aaron Francis

1
Andreas Kling, Creator of SerenityOS and the Ladybird Browser 1:11:20

1+ y ago1:11:20

1:11:20

Ben interviews Andreas Kling, creator of SerenityOS and the Ladybird browser. They talk about the concept of lifestyle software and how it relates to the development of SerenityOS, Andreas’ vision of creating a Zen garden for developers, and the benefits of using a mono repo and a unified language in the development process. They also touch on the …

1
Fable Tales, Staff Engineer at Stripe 1:05:31

1+ y ago1:05:31

1:05:31

In this conversation, Fable and Ben dig deep on building a technical career that balances programming and company leadership. Fable shares their experience working at Stripe and the different roles they have held, including being a technical advisor to the CTO. They also discuss Fable's career move from being a hands-on programmer to role where les…

1
Josh Pigford, Creator of Maybe.co 51:49

1+ y ago51:49

51:49

In this episode, Ben interviews Josh Pigford, founder of Maybe.co, about the company’s journey from VC-backed startup -> closed startup -> open source project -> funded open source project. They discuss JavaScript and Rails trade-offs, the challenges of building a personal finance software, and the operational difficulties of building a business ba…

1
Is ONCE enough? 1:10:58

1+ y ago1:10:58

1:10:58

A panel discussion on 37signals' first ONCE product, the launch of Campfire ("pay for it once, install it, and run it on your own server"). Ian Landsman, Tyler Tringas, and Justin Jackson share what they expected to happen before the launch, what did happen, and what it means for indie hackers and bootstrappers who want to launch SaaS companies. Is…

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Caleb Porzio, Creator of AlpineJS and Laravel Livewire 1:24:29

1+ y ago1:24:29

1:24:29

In this conversation, Ben interviews Caleb Porzio, the creator of AlpineJS and Laravel Livewire. The discussion ranges from discussions about life in general to specific testing practices and which notebook Caleb uses. Links Tuple.app - The best app for pair programming AlpineJS Laravel Livewire Caleb's VSCode Course Takeaways Apply core truths to …

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How Ben and David bootstrapped the Acquired podcast 1:07:50

1+ y ago1:07:50

1:07:50

Fast Company called Acquired "the #1 tech podcast sensation." I've been a huge fan of the show for years. So, I was surprised when they contacted me and wanted to switch to Transistor for podcast hosting! Since switching, they've had a breakout year. Their clips started showing up everywhere on my social media feed; they had chart-topping episodes …

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Taylor Otwell, Creator of Laravel 1:04:10

1+ y ago1:04:10

1:04:10

In this conversation, Ben interviews Taylor Otwell, the creator of Laravel. They discuss everything from the age-old argument of tabs vs. spaces to the origins of Laravel and how Taylor has turned it into a thriving, sustainable business. Links: Laravel, the framework Taylor created Tuple, used by the Laravel team to collaborates Takeaways Coding p…

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Building the HEY Calendar with Jason Fried 51:00

1+ y ago51:00

51:00

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 fi…

1
Ben and Adam review 2023 1:36:48

1+ y ago1:36:48

1:36:48

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)…

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Revisiting the Tailwind Labs business model 45:55

2y ago45:55

45:55

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) - Bl…

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Launching features like products 39:54

2y ago39:54

39:54

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 (…

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Building the right team with Jason Fried 1:11:30

2y ago1:11:30

1:11:30

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…

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Nashville team retreat: scary birds, country music, and a photo shoot 44:35

2y ago44:35

44:35

The whole team is on the show! Jon, Helen, Jason, Josh, and Justin are on the mics to discuss our recent team retreat to Nashville, Tennessee. If you're wondering what a retreat looks like for a remote team, you'll get a lot out of this episode. We also reveal some of our exploits in Music City: "Going to a Tiki Bar is usually a mistake." Highlight…

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Q&A: Starting over, the ideal employee, success and happiness, and selling the company 1:21:11

2y ago1:21:11

1:21:11

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 th…

1
Predictable mistakes of the developer-turned-founder 49:03

2y ago49:03

49:03

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 Mi…

1
Losing 70 lbs, getting in shape, and 15-minute workouts 59:26

2y ago59:26

59:26

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 relati…

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Paul Jarvis: gaining freedom by building an indie business 1:10:40

2y ago1:10:40

1:10:40

Justin catches up with his old internet friend Paul Jarvis. Today, Paul co-founded Fathom Analytics with Jack Ellis: a simple alternative to Google Analytics. Paul is also the author of the book "Company of One," which has influenced a whole generation of indie entrepreneurs (and has been reviewed by Cal Newport, Chris Guillebeau, Ben Chestnut, Tia…

1
Hiring is hard 1:06:59

2y ago1:06:59

1:06:59

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 Twitt…

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Enterprise sales for reluctant founders 1:00:33

2y ago1:00:33

1:00:33

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 s…

1
How to not suck at project management 49:18

2+ y ago49:18

49:18

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 episo…

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How Tim worked on side-projects for 10+ years, and finally went full-time (with kids) 54:14

2+ y ago54:14

54:14

Tim reached out after the Aaron Francis episode: "I wanted to pitch you on the idea of coming on the podcast and sharing my journey of building side projects for the last decade while raising a family. I can also share the guardrails I put in place before finally going full-time on T.LY." Highlights: (00:12) - Welcome (01:13) - Who is Tim Leland? (…

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Minimalist management with David Heinemeier Hansson 1:23:56

2+ y ago1:23:56

1:23:56

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…

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Startup coaching: helping founders and team members realize their full potential 56:02

2+ y ago56:02

56:02

This week Jon and Justin are joined by Marcella Chamorro. Previously, she worked in startup marketing but has recently transitioned to coaching founders and teams. We discussed how startup founders and their team members can realize their full potential. Here are some highlights: (00:24) - Introducing Marcella (03:03) - How do you define your coach…

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Michele Hansen update: Section 174 and bootstrapping with kids 1:00:53

2+ y ago1:00:53

1:00:53

In this podcast episode, Michele Hansen (Geocodio) gives us an update on Section 174 and provides her take on "bootstrapping with kids." Michele explains you can be a part of the Small Software Business Alliance, and fight Section 174. If you're in the USA, please contact Congress! In the second half of the episode, Justin and Michele talk about th…

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Should a parent with young kids try to bootstrap a new startup? 1:04:41

2+ y ago1:04:41

1:04:41

In this episode, Justin speaks with Aaron Francis about being a new parent and trying to bootstrap a startup. Aaron argued the other side of Justin's tweet thread: "Wait until your kids are older to start a company." Aaron is well-positioned to talk about this because he has twins and is also bootstrapping Hammerstone with his co-founder Colleen. T…

1
Lifetime pricing is underrated 1:00:24

2+ y ago1:00:24

1:00:24

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 …

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Why we hired someone new 45:26

2+ y ago45:26

45:26

Jon and Justin welcome Joshua Anderton to the Transistor team! Josh is an amazingly talented full-stack web developer (Laravel, Rails, Tailwind CSS, Alpine, and more!) He's been helping us as a part-time contractor since Oct 2022, and we're excited to have him on board full-time! In this episode, we discuss why we hired another person and how we th…

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Act now before it's too late: Section 174 33:10

2+ y ago33:10

33:10

Michele Hansen (co-founder of Geocodio) is raising the alarm about Section 174. This legislation could dramatically increase your tax bill this year if you're a small software company in the USA. Michele is organizing a response through the Small Software Business Alliance. 👉 ACT NOW: Sign up for Michele's list US citizens: tweet and call your Sena…

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Revisiting "The Ideal Bootstrapped Business" with Jason Cohen 1:24:40

2+ y ago1:24:40

1:24:40

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 Intro 00:27 Designing the ideal bootstrapped business 06:53 Recurring revenue vs one-off sales 13:30 Getting all the LTV…

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Running your business like a band 36:34

2+ y ago36:34

36:34

“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 Intro 03:05 Bringing on a band manager 07:34 Why the band metaphor works 11:54 Make things for your fans, not for your critics 14:49 Always do the …

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Lessons Learned in 2022-ish 47:36

2+ y ago47:36

47:36

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. Timestamps 00:00 Intro 02:11 Sett…

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This would kill our company immediately 38:31

2+ y ago38:31

38:31

Jon's back from his first real vacation in years. In this episode, we discuss how we've been removing inactive accounts on Transistor, SVB, Section 174, Revin is shutting down their Merchant of Record service, SaaS sales tax compliance: (00:37) - Jon in vacation mode (02:30) - Kicking off inactive accounts (04:30) - Silicon Valley Bank (06:06) - Wh…

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One pepperoni pizza please 2:06

2+ y ago2:06

2:06

"I don't get it: if that money is for the government, how come the pizza place put it in their cash register?!?" (Jon is on vacation - our next real episode is coming soon!) Listen to our past episodes on the headache that is SaaS sales tax compliance: Part 1 Part 2 Thanks to our monthly supporters Rewardful.com Greg Park Mitchell Davis from sixsid…

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Super Fun SaaS Sales Tax (Part Deux) 46:13

2+ y ago46:13

46:13

Last week's episode hit a nerve! "The idea that every small software company in the world will be able to be in perfect compliance will every foreign federal, provincial, state, and municipal government that imposes a sales tax is ridiculous. It's an impossible task. (00:11) - Follow up to previous episode (02:32) - Responses we got about sales tax…