Ben Orenstein and Adam Wathan on surviving the transition from dev to founder.
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 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.
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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...
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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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.
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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...
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.
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00:00 Intro
00:27 Designing the ideal bootstrapped business
06:53 Recurring revenue vs one-off sales
13:30 Getting all the LTV up front
18:31 Product validation
24:56 Creating a ca...
“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?”
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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 things you want to do
18:04 Turning over your rep over time
Two Guys (Bowen Yang and Matt Rogers). Five Rings (you know, from the Olympics logo). One essential podcast for the 2026 Milan-Cortina Winter Olympics. Bowen Yang (SNL, Wicked) and Matt Rogers (Palm Royale, No Good Deed) of Las Culturistas are back for a second season of Two Guys, Five Rings, a collaboration with NBC Sports and iHeartRadio. In this 15-episode event, Bowen and Matt discuss the top storylines, obsess over Italian culture, and find out what really goes on in the Olympic Village.
Listen to the latest news from the 2026 Winter Olympics.
The 2026 Winter Olympics in Milan Cortina are here and have everyone talking. iHeartPodcasts is buzzing with content in honor of the XXV Winter Olympics We’re bringing you episodes from a variety of iHeartPodcast shows to help you keep up with the action. Follow Milan Cortina Winter Olympics so you don’t miss any coverage of the 2026 Winter Olympics, and if you like what you hear, be sure to follow each Podcast in the feed for more great content from iHeartPodcasts.
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Saskia Inwood woke up one morning, knowing her life would never be the same. The night before, she learned the unimaginable – that the husband she knew in the light of day was a different person after dark. This season unpacks Saskia’s discovery of her husband’s secret life and her fight to bring him to justice. Along the way, we expose a crime that is just coming to light. This is also a story about the myth of the “perfect victim:” who gets believed, who gets doubted, and why. We follow Saskia as she works to reclaim her body, her voice, and her life. If you would like to reach out to the Betrayal Team, email us at betrayalpod@gmail.com. Follow us on Instagram @betrayalpod and @glasspodcasts. Please join our Substack for additional exclusive content, curated book recommendations, and community discussions. Sign up FREE by clicking this link Beyond Betrayal Substack. Join our community dedicated to truth, resilience, and healing. Your voice matters! Be a part of our Betrayal journey on Substack.