Ben Orenstein

35: Conducting Customer Development Interviews

March 29th, 2018  |  46 mins 2 secs

As part of his new business journey, Derrick requested that customers schedule time to talk with him about Level, a team communication and management tool he is developing. Luckily, about 40 people signed up, and he has completed 14 of these calls. What are his customers saying? They confirm main pains they feel with current tools and are very willing to share their frustrations with existing tools. Derrick has not been surprised yet about their answers.

In Ben’s world, he is spending time on slinging and reading about Haskell. He is full of questions. Both Ben and Derrick are learning a lot every day, which is fulfilling and exciting.

34: Maker vs. Manager

March 15th, 2018  |  48 mins 29 secs

It’s a Snow Day for Ben, and Derrick shares his woes about setting up his home office with two new, Dell monitors and his MacBook Pro featuring only two USB-C ports for a hub. You would think that laptops would offer more of a variety of ports. Other than that, things are going great for Derrick.

On March 5, Derrick pushed out his manifesto via Twitter. In response, people shared, retweeted, and posted supportive thoughts and messages. Developers resonated with his message. And of course, there were a few skeptics who wondered how Derrick’s ideas were different from other team communication and management options. There will always be multiple tools that can be used, but Derrick has a particular approach to what he offers.

33: The War on Developer Productivity

March 8th, 2018  |  27 mins 41 secs

Derrick recounts his last day at Drip - from being locked out, the elevator breaking, turning in parking passes, wearing a shirt saying “Quit Your Day Job,” to happy hour. He hadn’t even left yet and things were starting to fall apart!

Although he has a feeling of being free now, he is bummed about not seeing his co-workers every day. However, he is excited to share his plans and personal mission for the near future - a project called, Level, based on balance, not chaos.

32: Big Changes

March 2nd, 2018  |  31 mins 50 secs

Some significant changes are going on in our professional lives and today is full of updates.
Derrick is moving on from Drip to start a new company. Read the manifesto at http://www.derrickreimer.com.
Ben shares some of the details of his new job at Mackey Research Management Software. It’s providing him with structure, people, team interaction, and new problems, as well as a distance from some other problems.

31: Mental Health for Startup Founders with Sherry Walling

February 8th, 2018  |  23 mins 54 secs

Today’s special episode features guest Sherry Walling, author of The Entrepreneur's Guide to Keeping Your S**t Together, to be released February 21, 2018. Sherry explains how her book came to life and her experience self-publishing. We also talk about the common mental health issues for entrepreneurial founders in the community today.

30: Nailing an Interview, and the New Drip Design

January 25th, 2018  |  40 mins 46 secs

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.

29: Fitness and Code Quality in 2018

January 11th, 2018  |  54 mins 38 secs

Ben and Derrick welcome the New Year with this first episode of 2018. Derrick provides an update on his fitness goals for the first quarter of 2018 and plans his Bod Pod evaluation this week. Ben is launching the second cohort of The 30-Day Code Quality Challenge this week, and this cohort is even larger than the first.

28: Quarterly Goals, and Why They're Better Than Annual Goals

December 28th, 2017  |  1 hr 9 mins

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.

27: 30 Day Code Quality Challenge, and Elm Development

December 14th, 2017  |  51 mins 15 secs

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.

26: Optimizing Team Structures

December 7th, 2017  |  48 mins 22 secs

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.

25: Chaos, and Growing an Engineering Team

November 30th, 2017  |  1 hr 42 secs

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.

24: Tailwind CSS with Adam Wathan

November 17th, 2017  |  48 mins 15 secs

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.

23: Refactoring Rails Launch Breakdown

November 9th, 2017  |  25 mins 33 secs

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

22: Finishing the Year Strong

November 2nd, 2017  |  26 mins 46 secs

Ben’s course sales are still going strong, and he shares his updated sales metrics and the purchasing trends of his customers. He also spoke on the Ruby on Rails podcast recently to discuss the course and his experience making it.
Derrick and the Drip team are preparing for Black Friday. They built models to predict peak hours and optimize their servers. As a result they had a super successful test send at over 4,000 emails per second, putting them in a great position leading up to the big day.

21: Launching Refactoring Rails

October 26th, 2017  |  35 mins 40 secs

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.

20: The Ups and Downs of Working From the Road

October 19th, 2017  |  24 mins 26 secs

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.