

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

Oct 25, 2018 • 27min
60: Celebrating the Small Wins
The feeling of accomplishment you get from doing hard things has become Derrick’s way of living recently. Building a startup like Level is hard, but he feels good when he makes small wins. It’s rewarding when he makes progress.
Ben is on a roll right now with Tuple. He’s making progress and getting stuff done. His Pairing Programming Guide is turning people into Tuple subscribers.
Today’s Topics Include:
Have people with high standards read and review your writing to get feedback
Ben’s article, The Case for Pair Programming, was on the front page of Hacker News
Ben’s marketing efforts for Tuple have increased its number of subscribers
Derrick has a unique challenge of prioritization, so he set a deadline
Derrick used Postgres to build a rudimentary search into Level
By the end of October, Derrick should have people/teams to test and use Level
Product Task List: After you launch, that’s not the end, it’s the beginning
Balancing personal finances with no income; set the bar high, but don’t sell yourself short
Links and resources:
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
Tuple’s Pair Programming Guide
The Case for Pair Programming
Upcase
Indie Hackers

Oct 18, 2018 • 42min
59: Pros and Cons of Working Alone on a Product
Adam Wathan, a software developer, writer, speaker, and entrepreneur joins Ben and Derrick on this episode. Adam is also the creator of Nitpick CI, author of Refactoring to Collections, and host of the Full Stack Radio podcast.
Usually isolated and working alone, Adam enjoys the opportunity to chat with others about what everyone is working on. It’s like a mastermind session that’s fun and rewarding!
Today’s Topics Include:
Ben launched Tuple’s Pair Programming Guide earlier than expected at learntopair.com
Ben continues to focus on marketing for Tuple, while other team members are developing the product
Derrick feels a sense of guilt when working, but not sharing; once you get out of the habit of working in public, it might be difficult to return to it
Derrick is up against his deadline of having a deliverable by the end of October
Pros and cons of working alone or with partners to handle tasks/responsibilities
Rails vs. Laravel Battle? No, PHP as a language battles with no one
Adam is working on a refactoring UI book/design survival kit; chapters are independent and pricing still needs to be established
What are digital vs. physical perks you could offer to those who purchase a product first?
Derrick has been getting Level ready for alpha users and spending time, more than he wants, to get file uploads to work on it
Links and resources:
Adam Wathan
Nitpick CI
Refactoring to Collections
Full Stack Radio Podcast
Adam Wathan on GitHub
Adam Wathan’s Email
Adam Wathan on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
Pair Programming Guide
Product Hunt
Extreme Programming Book
Laravel
Ruby on Rails
Steve Schoger
Colorbox by Lyft
Tailwind CSS

Oct 11, 2018 • 57min
58: Evolving Roles as a Startup Founder
Ben and Derrick are joined by Brian Casel, podcaster, cofounder of Big Snow Tiny Conf, and known as “Mr. Process.” The three are fans of podcasts and conferences because they offer time to build relationships with people and talk deeply about things.
In this episode, they share their updates and thoughts on involving others in their day-to-day processes. It brings everyone together to learn from each other, as well as build a community and consensus.
Today’s Topics Include:
Hosting and handling logistics for smaller conferences and retreats
Ben shipped his Pair Programming Guide that offers tips, tutorials, and resources
Guide to serve as top of funnel for Tuple; build an audience, establish expertise, get people together who care about it, and offer them a tool
Flipping into different modes (writing, marketing, programming, etc.); in startup mode, you’re trying to make progress and doing everything - even when you have partners
More people are live streaming their coding sessions, writing processes, and other tasks - documenting the creation and development of a product or service
Build trust with a group of people to build referrals and have them talk about your product; but giving fans access to your product and building a community can be challenging
Building a new product; spend money to hire someone to do it fast or take it slow and learn to do it yourself but don’t get paid for your time
When building a company or product, it can be fun and frustrating; these days you should know a bit about all the pieces to it - teaching infrastructure is now an industry
Coaches and friends can give you advice and let you know just what you need to know
Practice Project vs. Real Product Mindsets: Perfecting something that you know won’t be perfect out of the gate, making it as good as possible, or plan first and then execute
Links and resources:
Brian Casel on Twitter
Productize & Scale
Big Snow Tiny Conf
BootstrappedWeb
ProcessKit
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
MicroConf
Startups for the Rest of Us
Tuple’s Pair Programming Guide
Pairing with Ben Orenstein on the Tuple Pairing Guide (with Adam Wathan)
Jason Fried
Laravel
Mackenzie Child
Drift and David Cancel
Ruby on Rails

Oct 4, 2018 • 53min
57: Finding the Right Marketing/Product Balance
Ben recently returned from an entrepreneur retreat that featured sessions and activities focused on various topics, from projects people were working on to troubles with cofounders. Attendees were able to be honest, open, and transparent with each other. Ben had the opportunity to demo Tuple during the retreat. Feedback was that there are too many people working on its development, so he should focus on marketing.
Derrick emphasized the importance of keeping in mind the cost of getting someone caught up to speed on a project. He has thought about hiring a contractor to help with the development of Level, but decided that his single brain was enough.
Today’s Topics Include:
Ben is working on a website to host the best pair programming guide on the Internet
Not getting on the content marketing treadmill, but coming out with 1 or 2 solid, comprehensive pieces of content that draw in people
Cascading style sheets (CSS) make your website site look good; should you hire a designer or learn the basics on your own?
Create a good network; know people who know about things, and ask for help
Derrick pushed a license update for Level’s code base; justified reasons why he should or shouldn’t make it an open source product and garner legal protection
Derrick’s original end-of-October people testing goal for Level is still possible; using Trello to list and clarify tasks
Finding a balance between making progress and doing other things that keep a product in people’s minds
Tuple’s team is starting to adopt more foundational processes to address tasks
Feedback from Listeners: More interaction and question-asking between Derrick and Ben, as well as bring people into their podcast process
Links and resources:
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
Thoughtbot
Big Snow Tiny Conf
MicroConf
Julian.com
Tailwind
Redis
Trello

Sep 20, 2018 • 26min
56: Finding Your One Thing
Ben is back from retreat #2 for Tuple. It may not have been as good as the first retreat, but was still above baseline productivity. The team worked on refactoring the app. Then, he went to CocoaHeads, which is for MacOS X and iOS developers to discuss Apple's Cocoa and CocoaTouch.
Derrick will be speaking about Level at the local Elixir meetup. He is excited to dive deeper into using Elixir and reading books about it. Then, he plans to share what he learns and encourage others to not be intimidated by more powerful concepts in Elixir.
Today’s Topics Include:
Ben talks about climbing; if he’s not good at something, that makes him feel bad, so he needs to overcome such a feeling
Derrick has been trying to figure out strategically how to provide a valuable service around Level’s open source code base; needs to put in the effort of learning how it’ll work
Importance of developing DevOps skills, knowledge - whether it’s you or in-house experts
As Derrick rapidly builds features for Level, he is tempted to either skimp on full-comprehensive testing or taking extra steps to refactor features into their ideal form
Derrick and Ben both are figuring out where they should be and where they should focus their time and efforts as they create their new products
Speed and quality are not traded off for one another; code has to be good to be added to and changed later quickly
Share what you’ve done with others to be reviewed and receive feedback; plus share your thoughts via Twitter with Ben and Derrick on how they can improve their podcast!
Links and resources:
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
CocoaHeads
Elixir
Thoughtbot
Discourse
Docker

Sep 13, 2018 • 25min
55: The Entrepreneurial Rollercoaster
Derrick is in Washington for ElixirConf. Like Elixir, he is becoming more comfortable with stability, as opposed to constant churn and new stuff all the time. He knows you have to show restraint to try and not solve every problem. While at the conference, Derrick wants to make connections with people and hopes Level will one day be a good use case example for the Elixir community.
Ben is discovering that startups are not easy. There are a lot of ups and downs. While other people were enjoying Labor Day, Ben was actually being a boss and getting work done. He may not have worked on the highest priority, but on a task that was satisfying to work on.
Today’s Topics Include:
Derrick has been keeping up his dev journal for Level by chronicling stories about the day-to-day building process; keeps him focused
For his journal, Derrick is using Svbtle, which offers a beta option to enable SSL for secure custom domains
Derrick is experimenting with newer Web platform functionality and built a custom element for Level to inject custom HTML and send push notifications
Ben was planning to pair using the Tuple app, but a bunch of stuff broke
Highs and lows with Tuple have been crazy; the lows make Ben wonder if it is ever going to work
Derrick tried using Level with someone else and everything seemed confusing; feel good about small wins, but rough spots can be difficult
Still a lot to do with Tuple, but Ben is making forward progress; keyboard support and other features have been merged - becoming a working app
Ben has some performance and latency leads for Tuple that are promising
Tuple continues to be tested inside and outside of Ben’s team to address variables
Links and resources:
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
The Level Journal
Tuple
ElixirConf
RubyConf
Heroku
Richard Feldman
Svbtle

Aug 30, 2018 • 32min
54: Continuous Learning
Ben has been focusing on MacOS development and writing code. There’s so much he doesn’t know. But that’s ok. He strives to regularly learn things - just keep making progress for it to feel less intimidating.
Derrick has the same mindset. It’s ok to not know everything. Start with the basics, and keep going. You’ll figure things out eventually.
Today’s Topics Include:
Ben is battling being part of the action or not and what tasks to handle; what is his role?
Ben feels guilty about changing his mind, but doesn’t stick with non-optimal decisions
Ben is discovering through calls and conversations that there is a market for Tuple
Derrick has been focused on the new version of Elm and migrating to it; Elm is not going to break, and it has been thoroughly tested
Level development continues with time spent on the Inbox; wants to get the MVP out
Derrick plans to do journaling to share things and keep people involved with Level
Make the Internet better and faster by not following stupid rules
Links and resources:
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Derrick’s Manifesto
Tuple
Elm
Basecamp
Drip

Aug 23, 2018 • 41min
53: Launching Transistor.fm with Justin Jackson
Today’s guest, Justin Jackson, just launched a podcast platform called, Transistor.fm. Justin describes the time he spent working with co-founder Jon Buda to get it ready to go live. Launching involves a lot of energy and emotion with ups and downs.
Whether working on your own or with someone else, Justin encourages you to take time away to work on something to focus on it and make significant progress.
Today’s Topics Include:
Reporting is key feature for podcast hosting applications; Transistor.fm offers an awesome analytics feature
When catching up with competitors, have a comparable minimum set of features
Some features don’t look good in screenshots; showcase a feature
Lots of time was spent on the launch, which Justin hoped would create a ripple effect for sign ups, word of mouth, tweets, and other engagement
People see something on Product Hunt, and they buy it; it’s an easy decision but not an intent-based audience - looking for entertainment and freebies
Splash for Transistor.fm made it the #1 product and generated sign ups
A podcast is an investment; Justin decided to use credit card sign up for Transistor.fm to build a brand and trust
Calculating churn, setting expectations, and reaching goals; banking on slow, steady growth
Starting work on Spots.fm, self-serve ads for indie creators; making it as easy to advertise on a podcast as it is advertising on Facebook
Get a company to sponsor you and write off as marketing expense; way for podcasters to earn income from their show
Talk, observe, and listen to “normals” to find that people buy things because of podcasts; don’t change people’s priorities to fit your ideals
Links and resources:
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Derrick’s Manifesto
Tuple
Build Your SaaS Podcast
MegaMaker
Justin Jackson Newsletter
The Importance of Trust with Your Audience with Justin Jackson
Transistor.fm
Laracon
Tuple Native App and Level Inbox Workflows
Product Hunt
Rob Walling
Tim Ferriss

Aug 16, 2018 • 26min
52: Tuple Native App and Level Inbox Workflows
Ben is back from a productive retreat with his Tuple co-founders. It was deep concentration work that didn’t feel like a chore, but a feeling of joy. They experienced a milestone - scrapped the electron-based version of their app to work on a native functional prototype. There’s a ton more to do, but it basically works. The pieces are coming together.
Derrick understands the foundation required to pretty much get anything done with a new product. He is considering a future retreat, but wondering if the benefits are worth it to go off somewhere as a solo founder. Or, would it be more productive to be just sitting at his desk at home? The most critical item on his radar and one of the biggest unknowns he continues to battle is how the mechanics of Level’s Inbox will work. If it doesn’t function well, then the whole promise of the app breaks down.
Today’s Topics Include:
Ben is trying to get to dog food ability - being able to pair using the app while actually working on the app
Ben is using Basecamp and GitHub Issues to manage tasks that are still left to do
Ben is still experiencing a steady stream of tweets, sharing, and sign ups for Tuple
Derrick also has a steady stream of tweets and is up to 4,500 handle reservations
Derrick is evaluating what paradigm he is mirroring when it comes to notifications and actionable to do items
It can be counterintuitive but ultimately helpful to think about something so technical that it sends you back into a loop of higher level conceptual thinking
Derrick’s making progress and at a decision point; trust his instincts and build something to be used, build a prototype, or build static mock-ups? Take a risk and set a date!
Links and resources:
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Derrick’s Manifesto
Tuple
Codetree
Basecamp
GitHub Issues
Drip

Aug 9, 2018 • 35min
51: Recast - The Origin of Level from Startups for the Rest of Us
Ben is out of town on a retreat with his Tuple co-founders, and Derrick is deep into building Level. So, this episode features Derrick as a recent guest on the Startups for the Rest of Us podcast. Rob Walling interviews Derrick about Level - what inspired the idea and how he went about trying to validate it.
Today’s Topics Include:
Level’s landing page and current query of number of members; scarcity play is effective
Level is a Slack competitor, but much less interruptive and more asynchronous
Derrick discovered Slack does not scale well as a team grows, interrupts people’s flow; Level is Derrick’s take on the solution to those issues
Derrick hit the ground running with his manifesto and getting people signed up for Level
His efforts on Twitter were effective because it’s a product marketed toward developers
Dealing with feedback, ill-informed comments and conversations
Derrick wanted to talk to too many, rather than too few people about value of creating a new product to address pain points
Differentiation from Slack: Level niched down to developers and open sourced
Derrick plans to offer free and on-prem versions of Level
Whiteboarding to go over ideas and transform them into something tangible
Derrick is working on mock-ups; challenging to lay out UI elements, such as the Inbox
Risks are involved; when building something new, the challenge is to validate your most risky hypotheses - the ones that are most likely to fail
Level is the third Saas startup that Derrick has worked on; first time he will not earn income or revenue while building Level, so had to make adjustments
Links and resources:
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Derrick’s Manifesto
Tuple
Fostering a Culture of Creativity with Rob Walling
Exploring the Open Source Business Model
Startups for the Rest of Us: How Derrick Reimer is Validating His Ambitious Third Saas
Application
Drip
Codetree
MicroConf