131: Making Calculated Bets

FromThe Art of Product

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131: Making Calculated Bets

FromThe Art of Product

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Length:

34 minutes

Released:

May 21, 2020

Format:

Podcast episode

Description

Derrick had a productive maker week and is (hopefully) a few weeks out from onboarding his first customers for the new product. He is becoming well-acquainted with the Google Calendar API. The Tuple team hired a full-time Mac OS engineer. Ben is thinking about opportunities to innovate with Tuple and taking inspiration from Bezos' shareholder letters.

Released:

May 21, 2020

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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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
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
22: Finishing the Year Strong: 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. by The Art of Product
27 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
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
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
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
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
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
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
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
33: The War on Developer Productivity: 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. by The Art of Product
28 min listen
31: Mental Health for Startup Founders with Sherry Walling: 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. by The Art of Product
24 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
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
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
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
36: Building Level: Derrick continues to talk with customers and gain insights about a team communication and management tool he is developing called, Level. Derrick is developing personal connections with people interested in his mission, and his conversations with customers is reinforcing patterns. Today, he shares the main problems with “Chat” functionality and why people are frustrated with the tools they use today. He is exploring possible solutions for Level to replace Slack and other tools. What issues do you experience? by The Art of Product
30 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
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
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
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
46: The Importance of Trust with Your Audience with Justin Jackson: Today’s episode features guest Justin Jackson, who is building a new podcasting startup called, Transistor.fm, and runs MegaMaker training and books for SaaS and indie software companies. He’s discovering that it’s a lot of work to build something. Derrick and Ben know how he feels. For Derrick, it’s been a fun week in the land of Level. He’s been working on his new landing page and landing new sign-ups for the pre-launch list. Ben has pre-sold $700 worth of Tuple accounts and raised $500 worth of verbal “Yeses.” Contact Ben if you want to be a part of Tuple. They share their ups and downs, fears and triumphs! by The Art of Product
66 min listen
29: Fitness and Code Quality in 2018: 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. by The Art of Product
55 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
35: Conducting Customer Development Interviews: 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. by The Art of Product
46 min listen
37: Pairing and Building In Public: Ben is now a Level contributor! Ben has paired with Derrick and his team communication and management tool called, Level - which is officially open source. Also, Derrick recorded himself building a Level feature and posted it on YouTube for feedback. It draws in people to see how an expert does things and share opinions and knowledge. It’s a win-win for everyone! by The Art of Product
29 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
12: Free Trials and Live Streaming Video Lessons: This week Ben discusses his experiment live-streaming a practice recording of his next video. He received helpful feedback and saw a spike in email subscribers, so it was very successful. Derrick has been working on the Drip free trial to help clarify the product plans. He debated split testing this move, but in talking to his team they decided to just go for it. by The Art of Product
39 min listen
39: Another New Beginning: Derrick discovered his marketing and promotional tasks were eating up too much of his time and mind, so he took a break from them. He shifted his focus to the actual development of his product, Level. He made some forward strides on the product’s design. Ben decided to give notice and leave his current job for an opportunity to develop a Screenhero alternative. Screenhero is a pair programming tool that has a rough history with Slack. So, he has a co-founder, new technology findings from Stanford, and encouragement from original developers. Could anything be more aligned?! Ben’s alternative and Derrick’s Level is a match made in heaven. by The Art of Product
27 min listen

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131: Making Calculated Bets

131: Making Calculated Bets

Description

Titles in the series (100)

More Episodes from The Art of Product

Related podcast episodes