

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

May 3, 2018 • 19min
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.
Today’s Topics Include:
What’s equity? Ben determines how to break up partnership percentages for his company
Each partner will have their moment in the sun, and contribute more or less at various times
Forming an entity; should Ben’s business be an LLC, corporation, private company...?
Domain scheme options when it comes to handles and extensions
Ben’s next milestone is to do a small alpha, and charge people to use it
Embedding iframes, custom domain options, and promotions
How cagey to be about technology being used; the secret sauce and general public licenses
Learning how to pitch a product and what resonates with people
Tools can be improved, and education on how to use them needs to be provided
Is Slack the problem, or the people who use it?
On premise vs. Cloud options; the pros and cons
If you’re enjoying the show please give us your ratings and reviews in iTunes.
Links and resources:
Ben Orenstein Website
Ben Orenstein on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Angel Funds
MicroConf
WebRTC
Andrew Culver

Apr 26, 2018 • 27min
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.
Today’s Topics Include:
How Derrick is refactoring and optimizing data model items
Is having one identity the right way to go or do people want to establish different identities within different communities?
Ben encourages Derrick to not automatically do the opposite of Slack
Derrick is trying to envision what people may request and be able to customize
Shifting from the anonymous to identified Web
Why Derrick decided to rewrite some database migration history
Derrick is developing Level’s registration and sign-up process
Derrick is on a development roller coaster every day; getting back on the yoga train
Development teams will become increasingly distributed, so the customer base for Ben’s alternative will only expand
How Ben feels about the technology risk factor with his alternative tool
Ben will be learning C++ to write the codebase and maintain it
If you’re enjoying the show please give us your ratings and reviews in iTunes.
Links and resources:
Ben Orenstein Website
Ben Orenstein on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Tailwind CSS
The Bootstrap Blog
Drip
GitHub
Steve Schoger
Screenhero
MicroConf
Thoughtbot
Ruby on Rails

Apr 19, 2018 • 19min
38: Choosing Tech Stack and Taking Preorders
Derrick is still moving in the right direction with the product he is developing called, Level. He used Product Hunt’s Ship to set up a landing page. He plans to promote his upcoming product and control its launch.
Also, Derrick published a blog post titled, Building Level #2: The Tech Stack. It summarizes his rationale and reasons why he chose specific technologies. Plus, he posted his and Ben’s conversation, Live Level #2: Branding and GraphQL Mutations, and created a Twitter handle for Level.
Today’s Topics Include:
Derrick plans to create bite-sized content to engage customers and build trust
Fake videos and info products and other shenanigans
Derrick has been splitting his time writing backend code and nailing down design
Getting feedback on mockups
Be aggressive by charging and collecting pre-payments
Ben will be going to MicroConf; taking a plane ride with leg room
If you’re enjoying the show please give us your ratings and reviews in iTunes.
Links and resources:
Ben Orenstein Website
Ben Orenstein on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Building Level #2: The Tech Stack
Live Level #2: Branding and GraphQL Mutations
Powered By Level on Twitter
Steve Schoger
Product Hunt’s Ship
Level on Product Hunt
Drip
Codetree
MicroConf

Apr 12, 2018 • 29min
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!
Today’s Topics Include:
Leveraging various networks to share information and provide value
Building a brand and putting capital in the bank
Impacts of stress on productivity
Engaging and sharing with interested parties; building relationships
Possible Milestone: Establish cadence of publishing frequency and balance of allocating time
Proposed Product Milestone: Use Level to track the work on Level
Utilizing GitHub to track tasks on To Do lists
Finalizing logo and identifying domain for Level
Value of retros
Prioritizing tasks and making progress on important, but not urgent work
Whether to focus on processes or engineering
Product roadmap and associated expectations/productivity
If you’re enjoying the show please give us your ratings and reviews in iTunes.
Links and resources:
Ben Orenstein Website
Ben Orenstein on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Level Live #1: Listing groups within spaces
Level on GitHub
Steve Schoger
Drip

Apr 5, 2018 • 30min
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?
Today’s Topics Include:
False sense of urgency; Derrick’s tool would allow you to filter notifications on whether they are urgent or not; and let users view messages at their own pace
Chat is like a conveyor belt; if you don’t pick things up, they are going to fall or you are going to miss them
Lack of Decent Threading: People do not find threads useful and difficult to encourage appropriate use of them
No Mechanism for Tracking State of Conversation: Everything needs to be reviewed to find information and decisions; should offer Open, Closed, Request Review, and On Hold, and other statuses
3 Ways to Structure Messages: 1) Subject and body; 2) Body; or 3) Very small message in infinite timeline
Derrick is clear on problems with existing tools, but less clear on exact solutions
Simple nuances can make a tool friendlier and easier to use - it’s all in the details
Derrick kicked off the Building Level series
Ben and Derrick strategize on the best approach to getting teams to try Level
Derrick is trying to make the barriers to using Level for low
Level will most likely be an open source product with a commercially hosted version to generate revenue
Ben and Derrick discuss when it is the best time to start developing Level publicly
Ben decided to say “No” to speaking at MicroConf this year; saying “No” to something, is saying “No” to one thing, saying “Yes” to something is saying “No” to everything else
If you’re enjoying the show please give us your ratings and reviews in iTunes.
Ben Orenstein Website; Twitter
Derrick Reimer Website
Building Level #1: Idea Validation
Twist
Drip
HipChat
Startup Stories Podcast
Stripe
Clearbit’s Reveal
Derek Sivers
MicroConf

Mar 29, 2018 • 46min
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.
Today’s Topics Include:
Level will not be a project management tool, but may have some project management capabilities
Derrick’s list of initial questions for customers: What is their company and role within it; the size of their team; what tools they use and when they adopted them; and the balance between chat, email, and project management in their organization
Derrick also asks customers: Why are they interested in Level? What problems do they want it to solve? What’s working well for them with Slack, and what’s not? What aspects of Slack do they use and don’t use?
Ideas for improvement have come from Derrick’s customers
Continuous integration is the clear winner for usefulness
Gauging willingness to switch to another tool, such as Level
Customers expressed using Level on a pilot basis for specific teams or projects and in coordination with at least one other tool
Being unable to post asynchronous, long-form discussions is a pain point for some customers
Paying for a tool would not be a big deal
Derrick plans to kick off his building Level series and build mock-ups for customers to view
Positive use of minimalist user interfaces
Debating whether to offer a pre-payment option for Level
Ben uses Ansible for the deployment of Haskell code
Ben is seeking a Dev Ops person to hire - must have strong opinions and can fix stuff
SaaS Renaissance? More developers are starting SaaS companies - a trend already on the way out?
Level will be SaaS but with an open source core
Tools SaaS companies will want to have and buy
Not Built Here Syndrome: Engineers who outsource non-essential parts to someone else
Pricing Pages as a Service: Shopify’s checkout page feels natural but still represents the company
Avoid rebuilding stuff
If you’re enjoying the show please give us your ratings and reviews in iTunes.
Links and resources:
Ben Orenstein Website; Twitter
Derrick Reimer Website
Basecamp and Getting Real
Haskell
Programming in Haskell book
C Programming Language by Brian Kernighan and Dennis Ritchie (K&R for C)
Ruby on Rails
Ansible
Drip
Salesforce
Product Hunt
GitLab and Discourse
Stripe Atlas
Andrew Culver’s Bullet Train
Adam Savage: One Day Builds
MicroConf 2018

Mar 15, 2018 • 48min
34: Maker vs. Manager
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.
Today’s Topics Include:
Maker vs. Manager: A good way to draw a line between how different people feel about a tool
“This is people problem, not a tool problem” There are a lot of people who just don’t get it.
Tools help guide the way users use the product and how your team works
Some tools generate stress and interruptions rather than constructive work progress
Goal: Communication centralized in one place
Email is now a black hole, and no longer for actionable items
Important information can get lost in all the noise created by some tools
Derrick plans to keep his email subscriber list warm by not over-emailing them without a product available yet
Derrick has received 400 emails so far as a result of his Twitter push and plans to do outreach, development, and validation with customers
Attribution Tracking App: Ben encouraged Derrick to request pre-pay for future products, like for the app he was thinking about building; pre-payments offers validation
Derrick has not determined a price plan or how to sell the dream yet
Derrick plans to keep thinking through product decisions on pen and paper
Deliver on the promise of the tool guiding people to use good communication patterns
Tools need to maintain connectedness
Entrepreneurship Porn: Share your thoughts, ideas, process, and journey with others
Engagement and Authenticity: A give-and-take between you and your subscribers
Journal milestones; the more chronicling, the better
Derrick’s prototype includes Phoenix, Elixir, and GraphQL
Ben shares his experience with Haskell vs. Elm; he has more questions than answers at this point
Haskell has a chance of being the gateway drug of functional programming languages
Attend meet-ups and conferences to learn more about Haskell and Elm
With programming languages, you need to be willing to make some sacrifices
Ben is beginning to appreciate aspects of project management and positively influencing processes
If you’re enjoying the show please give us your ratings and reviews in iTunes.
Links and resources:
Ben Orenstein Website; Twitter
Derrick Reimer Website
Basecamp
Twist
Drip
Calendly
Jason Fried
Startup Stories Podcast
GraphQL
Elixir
Phoenix
Haskell; Programming in Haskell book
Elm
Ruby on Rails
Thoughtbot

Mar 8, 2018 • 28min
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.
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.
Today’s Topics Include:
Derrick’s Manifesto: What he is now doing and thinking
Building a prototype to get rid of Slack in the workplace
Wants to develop ways to improve team communication
Parts of Slack are awesome, while others are not
Chat is not an effective communication mode for teams
Important conversations can get lost in the chatter
Snoozing is stressful; can be taken negatively and feel like being ignored
Inbox should be included and organized by threads
Anything that is important and needs to be addressed should be in a thread
Slack is not meant for actionable items, but people use it for that
Derrick’s tool will have both sync and async, which can be married; will be difficult to misuse it
Some tools become addictive and disruptive to human nature
Pushing through notification barriers and specifying priority; a list that prioritizes items and deadlines
Step 1 to creating such a tool: Do your homework by talking to teams of developers
Ben’s March will consist of meditating, squats, and handstands - while working on goals; Derrick wants to achieve reading and personal fitness goals every day, as well as shipping something open source
If you’re enjoying the show please give us your ratings and reviews in iTunes.
Links and resources:
The War on Developer Productivity (And How I Intend to Win It)
Drip
Slack
Thoughtbot
Rob Walling
The Entrepreneur's Guide to Keeping Your S**t Together by Sherry Walling
Zero to One book
Ben Orenstein Website

Mar 2, 2018 • 32min
32: Big Changes
Some significant changes are going on in our professional lives and today is full of updates.
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. Mackey is a company that makes a note-taking app for hedge funds and features a connection to databases of public companies. Derrick is moving on and away from Drip. While he knows the time is right to move on, there is emotional attachment especially since he was there from the start. Derrick wants to go from leading to doing, again. He’s leaving his “baby” that he co-founded in the best state possible. Derrick is putting together a manifesto about possible upcoming plans.
Today’s Topics Include:
Reasons for moving away from Rails
Ride the wave of different languages
Projects based on learning vs. productive; never stop learning to be relevant
Change in pace and work environment is positive for Ben
Flexibility is a benefit, but it is not for everyone
Stress level difference between working at a job or running your own company
If Ben likes Haskell, he’ll want to talk and teach about it
Haskell has some brain-bender, mind-expander aspects
With Haskell, it feels more like play than work for Ben - and you get paid for it
Derrick has learned to delegate over the years; no longer a bottleneck
New chief technology officer with top-level experience being hired to continue to grow Drip
Derrick will post a manifesto on his website about his upcoming plans
Derrick has been going through administrative tasks required as he transitions away from Drip
Derrick says, even during the dead of winter, that he plans to stay in Minnesota
A logo is being created for Art of Product; and Derrick is working on establishing a brand identity related to his new ventures
If you’re enjoying the show please give us your ratings and reviews in iTunes.
Links and resources:
Mackey
Haskell
Sherry Walling Mental Health for Startup Founders - Art of Product episode
The 30-Day Code Quality Challenge
RefactoringRails.io
Drip
Derrick Reimer Website
Ben Orenstein Website

Feb 8, 2018 • 24min
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.
Today’s Topics Include:
Mental health within the Founders community
Sherry’s new book and her writing process
Struggles during the publishing process
Traditional versus self publishing on Amazon
Strengths and ‘shadows’ of entrepreneurs
Personality self-knowledge and introversion/extraversion
If you’re enjoying the show please give us your ratings and reviews in iTunes.
Links and resources:
The Entrepreneur's Guide to Keeping Your S**t Together by Sherry Walling
Zen Founder
Zen Founder Podcast
Quiet: The Power of Introverts in a World That Can't Stop Talking by Susan Cain
MicroConf
The 30-Day Code Quality Challenge
RefactoringRails.io
Drip