Best Ben Orenstein Podcasts (2024)

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

2M 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
Matt Swanson, CTO at Arrows 45:25

3M 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…

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

3M 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

4M 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…

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

4M 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…

1
Ben steps away from Tuple 1:11:22

5M 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

5M 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

5M 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

6M 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
Caleb Porzio, Creator of AlpineJS and Laravel Livewire 1:24:29

7M 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 …

1
Taylor Otwell, Creator of Laravel 1:04:10

7M 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…

1
Building the HEY Calendar with Jason Fried 51:00

8M 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

8M 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)…

1
Revisiting the Tailwind Labs business model 45:55

9M 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…

1
Launching features like products 39:54

9M 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 (…

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

10M 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…

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

12M 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

1y 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

1y 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…

1
Hiring is hard 1:06:59

1y 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…

1
Enterprise sales for reluctant founders 1:00:33

1y 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

1y 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…

1
Minimalist management with David Heinemeier Hansson 1:23:56

1y 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…

1
Lifetime pricing is underrated 1:00:24

1+ 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 …

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

1+ 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…

1
Running your business like a band 36:34

1+ 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 …

1
Lessons Learned in 2022-ish 47:36

1+ 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…

1
Playground Bucket 3:46

3y ago3:46

3:46

An interaction at the playground leads to bigger and bolder things.By Matt Jankowski

1
Getting a deal with Uber, and then another, and another with Daniel Zarick of Arrows 49:23

3y ago49:23

49:23

Welcome to Sales for Founders, the podcast for founders who want to go from hating sales to making sales. Today, Brendan is speaking with Daniel Zarick. Daniel is the co-founder of Arrows, a collaborative onboarding tool for high-touch customers. Before that he ran an app design studio and was the 2nd product manager at Twilio. You can follow Danie…

1
Hey... Sales can be fun! Perspectives on Founder Sales with Ben Orenstein of Tuple 30:16

3y ago30:16

30:16

We're pleased to have Ben Orenstein in as our guest this week. Ben is the co-founder of Tuple, a pairing application for development teams, and he has deep experience as a tech founder. In this quick and lively episode, we cover several common sales challenges for founders, like: - Dealing with customers, behavior change, and getting things done. -…

1
Sales Chat #4 - Optimizing that first sales call 49:36

3y ago49:36

49:36

Okay... It's time for that big initial sales call. You've booked, prepped and dialed in (or maybe you're in-person...right?!) Now what do you do? Plenty, actually. And a lot of it is simple, fundamental, easy, and actionable. And all of it can make that first sales call much more effective. In this episode, Brendan and Louis break down the key prac…

1
Sales Chat #3: Brendan and Louis get into how to prepare for an important first sales call 30:33

3+ y ago30:33

30:33

Welcome to Sales for Founders, the podcast for founders who want to go from hating sales to making sales. First impressions can make all the difference, and that's especially true when it comes to the first important conversation you have with a prospective customer. Things move quickly, you're still figuring each other out, and there are plenty of…

1
SaaS sales and the struggle to gain meaningful customer adoption with Joe Valenti, founder of BrokrBindr 46:55

3+ y ago46:55

46:55

Welcome to Sales for Founders, the podcast for founders who want to go from hating sales to making sales. We have Brendan McAdams at the microphone today for a conversation with Joe Valenti, founder of BrokrBindr, a SaaS application that automates the various functions and processes in the operation of a mortgage broker business. We're talking SaaS…

1
Sales Chat #2: Why's a sales process so important? — with cohost Brendan McAdams 27:13

3+ y ago27:13

27:13

Welcome to Sales for Founders, the podcast for founders who want to go from hating sales to making sales. Louis is back behind the mic for another season of Sales for Founders... ... and this time he's joined by a cohost — sales expert and previous guest Brendan McAdams! We're mixing up the normal format this series with a mix of real-life founder …

1
Sales chat #1: Is sales sleazy? — with cohost Brendan McAdams 43:12

3+ y ago43:12

43:12

Welcome to Sales for Founders, the podcast for founders who want to go from hating sales to making sales. Louis is back behind the mic for another season of Sales for Founders... ... and this time he's joined by a cohost — sales expert and previous guest Brendan McAdams! We're mixing up the normal format this series with a mix of real-life founder …

1
152: Ben Orenstein - How to Stand Out When Applying for a Job at a Small Company 47:43

3+ y ago47:43

47:43

Topics: Putting yourself in the shoes of the person reviewing your application Crafting a high quality application tailored to a specific position Standing out in a more traditional hiring process by doing something a little extra Showcasing very specific examples of your work instead of asking the person reviewing your application to go hunting fo…

1
151: DHH – Building HEY with Hotwire 1:14:00

3+ y ago1:14:00

1:14:00

Links: Hotwire HEY Supporting the show: I decided to stop taking sponsors for the show because I think advertisements are annoying and no one wants to listen to them. If you do want to support the show, the best way to do it is to purchase one of my products: Tailwind UI, a collection of professionally designed, fully responsive HTML components bui…

1
Lessons from 20+ years of sales success — with Brendan McAdams, cofounder of Expertscape 41:16

3+ y ago41:16

41:16

Welcome to Sales for Founders, the podcast for founders who want to go from hating sales to making sales. This week, your host Louis is talking to sales expert Brendan McAdams. Brendan is the cofounder of Expertscape. He also has over two decades of experience working as a salesperson. And — last but not least — he recently released a book and runs…

1
150: Secret Screencasting Tips & Behind the Scenes of Tailwind CSS 2.0 59:12

4y ago59:12

59:12

Supporting the show: I decided to stop taking sponsors for the show because I think advertisements are annoying and no one wants to listen to them. If you do want to support the show, the best way to do it is to check out our products: Tailwind UI, a collection of professionally designed, fully responsive HTML components built with Tailwind CSS. St…

1
149: Choosing a Payment Processor, Radical Icons & W3C Hype 56:38

4y ago56:38

56:38

Links: Changes to Gumroad's PayPal support Radical icons Jack's hand-drawn avatars W3C's CMS Selection Report Supporting the show: I decided to stop taking sponsors for the show because I think advertisements are annoying and no one wants to listen to them. If you do want to support the show, the best way to do it is to check out our products: Tail…

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