218: Building a $1M/Year Dev Ed Business (with Adam Wathan)

FromThe Art of Product

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218: Building a $1M/Year Dev Ed Business (with Adam Wathan)

FromThe Art of Product

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Length:

78 minutes

Released:

Oct 26, 2022

Format:

Podcast episode

Released:

Oct 26, 2022

Format:

Podcast episode

Titles in the series (100)

The Art of Product is a podcast chronicling the journeys of two entrepreneurs building software companies. Hosted by Ben Orenstein and Derrick Reimer.

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10: Dynamic Website Personalization with Brennan Dunn: Today Ben’s guest is Brennan Dunn, co-founder of RightMessage, a tool that allows you to personalize your website based on user information and behavior. This allows you to customize your messaging to each user’s unique story and needs. Brennan explains the value of customer targeting, shares his ambition for Right Message, his personal journey and advice for other software startups along the way. by The Art of Product
41 min listen
9: Deep Thinking and Finding Your Groove: This week Ben is adjusting to jet-lag from his travels to Las Vegas and Martha’s Vineyard last week. He did however manage to release another episode of his sample campaign that was recorded before his vacation, so he is making good progress with the course. Derrick is celebrating and reflecting on the one year anniversary of the Drip acquisition. They have gone from 3 to 10 engineers in the last year, and have really hit their stride in productivity. by The Art of Product
24 min listen
3: New Pricing Strategies: Updates and pricing strategies highlight today’s episode. Ben did yoga this morning, and he is feeling relaxed as he is settling in with his new lifestyle. Next week Ben is closing his first part-time chief revenue officer engagement. Now it’s time to come up with a contract and a pricing strategy. by The Art of Product
33 min listen
19: Gourmet Ruby with Avdi Grimm: This week Ben Orenstein is interviewing guest Avdi Grimm, Founder of RubyTapas, which is a subscription service that provides screencasts of “gourmet” ruby programming. Avdi discusses the topic of his talk at Southeast Ruby in Nashville, which was the value of avoiding code and strategies to bypass the need to write unnecessary coding. Join us as he shares his advice on optimizing workflows and his experiences building RubyTapas. by The Art of Product
31 min listen
18: Preparing for Black Friday: Ben has finalized the logo for his Refactoring Rails course and is currently getting the intro/outro animations and the sales site designed. He also finished the notes for all the videos and was very pleased with the final edit quality. At Drip, Derrick is deep in the backend scaling challenges with a lot of attention towards Black Friday for their ecommerce customers. They are looking to historical data in order to anticipate peak volumes and simulate high loads. by The Art of Product
27 min listen
6: Refactoring Rails and Shareable Workflows: On today’s episode we discuss Ben’s release of the first video in his Refactoring Rails course, on the benefits of following Rest in Rails applications. He goes over how he produced the video, sent it out and the feedback he got on his initial release. Derrick has been shipping even more this week, and has seen a huge improvement in his workflow by reducing the notifications on GitHub. His team is adjusting to a more efficient way of working instead of push notifications. by The Art of Product
34 min listen
2: From Good to Great: Welcome to the Art of Product podcast. Derrick is rocking his “I ♥ yoga” shirt because he started practicing yoga at a studio down the street. He also gives us an update on new changes and features at Drip. Derrick was inspired by Ben’s newsletter and decided to work on his own newsletter, which gave him a great opportunity to use his own product. Ben is discovering that unemployment is a roller coaster. His stress level has been about 5X his normal baseline stress level. He started working at the co-working space and attending mixer events. He is emailing people on his list and sharing his ideas to get feedback for possible products for him to work on. Ben has been reflecting on how people and relationships make him shine and is considering finding a co-founder for his product. by The Art of Product
35 min listen
26: Optimizing Team Structures: Drip successfully sailed through Black Friday and Cyber Monday unscathed with no queue backups or problems. Derrick has been thinking about shifting the Drip team structures after Black Friday weekend and is considering adopting more efficient workflows and processes. Ben and Derrick discuss different team structures, including those at Basecamp and Spotify. They also talk about team size, communication overhead, and growing revenue versus growing team size in business. by The Art of Product
48 min listen
4: Always Talk With the Decision Maker: In this episode, Derrick is broadcasting from California as he visits his family. Ben went to Vermont last week and quickly realized how relaxing it is to be outside and see greenery. Such a different feel from the tension in the city. Ben has been chatting with a couple of people about consulting as a revenue officer. He had an interesting chat with someone but their visions just weren’t aligned in terms of value and compensation. Also it turned out this person wasn’t the decision maker, and the founder wasn’t as agreeable to Ben’s terms. Lesson learned - always talk to the decision maker. Ben is also struggling with whether he really wants to be involved in consulting. He may want to just focus on his product. Enjoy the show. by The Art of Product
31 min listen
17: Launch Planning and Speaking at Conferences by The Art of Product
33 min listen
24: Tailwind CSS with Adam Wathan: Ben and Derrick are joined by guest Adam Wathan, an esteemed software developer, writer, speaker and entrepreneur from Ontario, Canada. He is the creator of Tailwind CSS, author of Refactoring to Collections and host of the Full Stack Radio podcast. Listen in as he shares how he built his own products over time and became an independent entrepreneur, and talks about his new project Tailwind CSS. by The Art of Product
48 min listen
16: Going Viral and Customer Driven Products: Ben and Derrick are back from vacation this week are feeling refreshed. Ben tweeted something that went viral and has dealt with some people’s misinterpretation and bias. He is working on hiring a designer for some of the course finishing touches and is honing in on the premium tier offerings. Drip has been onboarding a new developer onto the core-product team and Derrick discusses his interview and hiring process. He also shares how Drip is doing as a customer-driven product team. by The Art of Product
45 min listen
5: Ways We Maintain Focus: Today we talk about how Ben just launched his new landing page and set up the domain for his new Rails video course. Derrick has been shipping stuff this week. He just rediscovered the pulse tab on GitHub which gives a nice summary of what they have done over the week. by The Art of Product
33 min listen
1: Welcome to The Art of Product: Welcome to the Art of Product podcast. This is episode 1, and just the beginning of the journey. This is a show with Ben Orenstein formerly from thoughtbot and Drip co-founder Derrick Reimer. Ben recently quit his job at thoughtbot, and is now focusing on what he is going to do next. Stay tuned. This is going to be a fun journey. by The Art of Product
34 min listen
28: Quarterly Goals, and Why They're Better Than Annual Goals: Ben is having a successful push for the new cohort of The 30-Day Code Quality Challenge. He is also looking to improve future iterations of the challenge and is preparing to move to a new home outside of Boston. Ben and Derrick discuss their quarterly personal goals on this episode and the philosophy behind goal setting: developing habits versus achieving specific results. by The Art of Product
70 min listen
21: Launching Refactoring Rails: Ben has officially launched his course Refactoring Rails. He is pleased with his choice of back-end tools including Gumroad for fulfillment. Ben shares his course launch metrics including email success rate, sales numbers and revenue. Derrick announces Drip’s new project teased last episode: a visual email editor. Due to Drip’s widening customer base, there is an increased demand for visual and polished marketing emails. by The Art of Product
36 min listen
23: Refactoring Rails Launch Breakdown: Ben keeps us posted on the Refactoring Rails course launch progress and shares his continuing sales metrics and marketing strategies. He is considering experimenting with free samples, bundling and cross-promoting going forward. For his next project, Ben is creating a new course called The 30-Day Code Quality Challenge, which goes live on November 13, 2017 by The Art of Product
26 min listen
7: Learning from Successes, and Failures: This week Ben has been trying new productivity techniques and studying different systems of workflow. He finished a new course video on Page Objects, and has sketched out a second video to hit his pre-vacation goal. Derrick had a technical issue over the weekend, which his team worked out and stabilized. He has decided to adopt a “blameless post-mortem” approach to problem-solving going forward. by The Art of Product
39 min listen
27: 30 Day Code Quality Challenge, and Elm Development: Ben is entering the last week of The 30-Day Code Quality Challenge. He has enjoyed getting the challenges out each day and seeing participants engage with the content. In the future he is deciding whether to personalize the programming languages or to remain language agnostic. Drip is working on their visual email builder with the help of their new Elm developer. The team has just completed several product structure tests using a prototype, which was a greatly helpful experience to the developers. by The Art of Product
51 min listen
13: Crossing the Chasm: This past week Ben has hit a mental slump in the final phase of his course. However, he is moving through it and will be recording another video today towards the new final goal of 8 total course videos. Derrick brings up a recent Giant Robots podcast episode with Seth Godin, which talks about the dips experienced in business, “crossing the chasm” by moving from innovators into the mass market, and the personal transparency of the host Chad Pytel. by The Art of Product
33 min listen
40: MicroConf, Equity, and Corporate Entities: Ben and Derrick are together again, at MicroConf and working on their new products and businesses. From making T-shirts to thinking about finding funds, things are continuing to move forward. Derrick is focusing on Level, an open source team communication and management tool. Ben is considering the name, Tuple, for his pair programming tool alternative for Screenhero. He is focusing on all things business-related, from equity to entity options. by The Art of Product
19 min listen
14: The Power of Simplicity: This week Ben has been managing his projects and to-do list with OmniFocus, which helps as his business and stress level continue to increase. He has outlined and will be recording his last video about form objects and is glad to be approaching the finish line on the course. Derrick has been in the trenches working on scaling Drip this week by strategizing on architecture with the backend team. They have onboarded one of their biggest customers and are working with them to segment and filter subscribers to be more efficient. by The Art of Product
42 min listen
45: The Value of Teaching by The Art of Product
41 min listen
20: The Ups and Downs of Working From the Road: Ben is set to launch his course and is using the looming deadline as an efficiency booster. He recently spoke at Rocky Mountain Ruby, and spent time prepping the talk with a friend at a beach house but unfortunately lost his data due to a hardware malfunction. The talk was still a great success, but a very stressful experience. Drip.com is now live after a long process, and the Drip team is thrilled. Derrick has also found an opportunity to use Elm at Drip, and is looking forward to implementing it in a new project he can’t yet discuss. by The Art of Product
24 min listen
30: Nailing an Interview, and the New Drip Design: Ben has moved into his new apartment and had an interesting discussion about fitness with the movers. Derrick got back is Bod Pod results and is formulating his precise fitness goals for fat loss and muscle gain. Ben is still on the job market and had an interview last week. In Drip news, Drip recently got a brand refresh, including a new logo, marketing site, color palette, new messaging, app skin, and more. by The Art of Product
41 min listen
41: MicroConf 2018 Takeaways: Ben and Derrick are recovering from days of being in Las Vegas for MicroConf. They spent time reconnecting with old friends, and making new friends. Knowledge floats around, and you can soak it all in. MicroConf has a culture of extreme transparency, helpfulness, friendliness, and wealth of value. Talks at the conference generated actionable items for and awe from attendees. by The Art of Product
32 min listen
11: The Founders Dilemma: Derrick is coming back from a much-needed vacation in San Francisco and enjoyed walking tours thanks to the Detour app. He returns refreshed and was able to get back into the swing of things and even into his yoga classes. Last week Ben published a new sample course video on speeding up slow test suites. He is improving his recording and editing processes using Final Cut Pro. He is now working on the fifth video and nearing the halfway point on the course. by The Art of Product
33 min listen
25: Chaos, and Growing an Engineering Team: Ben introduces The 30-Day Code Quality Challenge and updates us on the progress of his first cohort. He has been receiving positive feedback and participants are engaging with the exercises and community forums. Derrick has hired an Elm engineer at Drip and they discuss the adoption of the Elm programming language in the industry. He also shares the hiring and pairing interview process of the candidate. by The Art of Product
61 min listen
8: Different Paths to Software Development with Ian Nance from Drip: This episode Ben is on vacation and we have a guest, Ian Nance, a Drip team member here to talk about his backstory and how he got into software development. Ian has an interesting story about how he started programming later in life and his work experiences. Join us as he shares his journey and some great advice for beginners in the field. by The Art of Product
30 min listen
15: Lessons in Scaling SaaS: This week Ben is on vacation and Derrick is here to share some fresh knowledge behind the scenes at Drip. They’re experimenting at Drip with how to scale the system to handle more customers and what changes are needed to make the architecture support all their customers and future large customers in the sales pipeline. Derrick goes over his team’s recent brainstorming session and plans to repeat the exercise for more subsystems at Drip. by The Art of Product
7 min listen

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218: Building a $1M/Year Dev Ed Business (with Adam Wathan)

218: Building a $1M/Year Dev Ed Business (with Adam Wathan)

Titles in the series (100)

More Episodes from The Art of Product