

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

Jul 26, 2018 • 32min
50: Doing the Hard Things First
Derrick continues to reinvent himself with his new product, Level, and sporting a, “I work for myself beard.” He took a vacation to canoe and camp instead of code. It’s always a refreshing experience for him to get away from work from time to time. Now, Derrick is back to writing code and organizing tasks in Levelland.
Ben also went on vacation, but before doing so, he realized no sales for Tuple had come in that week. So, he made an effort to call prospective clients and was able to sell six annual licenses. Now, like Derrick, he is working on things that are hard to achieve. But if they can make them happen, then they will be really good.
Today’s Topics Include:
If feeling overwhelmed, write everything down, break into chunks, and organize them
Find a visible way to make sure you are making progress and staying on track
Ben wants to talk to other CEOs of small companies to find out what are they focused on and paying attention to because there is so much to do
Don’t beat up yourself over mistakes, just keep making progress
AoP podcast is like therapy and leaning on each other for support during this journey; staying sane during the new company/product process
Prioritize Properly: Get sleep or you’re operating at a fraction at what you could be
Break up your day and work schedule into 2-3 hour segments; if you need to get something done, spend less time doing it
Teams contacted Ben about participating in the Tuple alpha; spots are still available, so contact him
Company or founder retreats are a way to get creative, think outside the box, and bond over shared challenges and struggles
Ben’s team, Sam Deane, including has been cranking away on its native app to create the initial set-up, layout, and architecture
Ben tweeted about how to get up to speed on Mac OS development; considered corporate overlord’s job to create education and training, so it doesn’t get done
Looking back on a year if AoP: Derrick overcame his fear of the microphone, and they’re keeping it real; humbled and happy that people find it useful
Links and resources:
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
Hill Charts on Basecamp
Trello
Drip
Rob Walling
Sketch
Giant Robots Smashing Into Other Giant Robots
Microconf

Jul 12, 2018 • 22min
49: The Evolving Tech Stack
Derrick continues to code to make progress on things he will need to build at some point for his product, Level. Also, he spent a lot of time in Elm land for refactoring and additions. Will Elm code work for scaling necessary for Level? Derrick is still trying to decide.
Ben’s team at Tuple has transitioned from C++ to Swift, a newer and friendlier language. Also, Tuple hired a consultant as a sanity check and to be pointed in the right direction for building a native app on Mac. Initially, the consultant will help step up and build with dependencies needed.
Today’s Topics Include:
Level App: There’s a lot of work to do and time is flying by; not sure when it’s going to be ready, but every day, make progress
More than 800 people have signed up for Ben’s Code Quality Challenge; people engaged in it are getting value, doing useful things, and improving their apps
Advantages of building your network up online; they share and inquire about info you post
Types of tips that spread fast, including bash, shell, and git
Ben plans to reach out to people to make podcast appearances to promote Tuple
Ben stepped away from sales, but now plans to make money for the company his #1 priority; difference between self-funding and bootstrapping
Being in a constant state of push-and-pull; when to do this/that and change directions
If you’re interested in entrepreneurship, read Shoe Dog by Phil Knight; jumping through hoops and funding a company
Check out Founder to CEO by Matt Mochary, who coaches tech startup CEOs in Silicon Valley; what do you need to know to grow?
Friendly reminder if you’re going camping this summer, remember to take mosquito repellent with you!
Links and resources:
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
Elm
Richard Feldman on YouTube
Swift
Derrick Reimer on Startups for the Rest of Us
Derrick Reimer on Full Stack Radio
Ben Orenstein’s Code Quality Challenge
Ben Orenstein’s Shell Tricks Post
Shoe Dog
Founder to CEO

Jul 5, 2018 • 31min
48: When Is the Right Time to Take Outside Funding?
Derrick was hoping to finish mock-ups for communication flows inside Level to get feedback, but that turned out to be a lofty goal that he is still working on. The process of designing Level has generated more questions than answers and minute details that Derrick needs to address. This is the real work happens.
Congrats to Ben, who finally crossed 10,000 followers on Twitter. He uses Twitter as a way to provide value, be useful, and build relationships. Also, he launched the Code Quality Challenge sign-ups and a private podcast to share information with people who are interested in Tuple.
Today’s Topics Include:
Interest in seed funding? Different ways to raise funding
Being in complete control of your destiny and avoiding failure
Doubling down to take investments; what’s it like to be in a business environment that received funding
Rob Walling’s experience with funded companies; listen to a recap of 12 Lessons I learned Moving from Bootstrapped to Venture Backed
Personalities and psychology of founders impact own vs. others’ money
Flexibility: Choose to push hard and make something profitable or not
Head lamp requirement to enjoy the great outdoors, and how being tall has its benefits
Links and resources:
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
Drip
Briefs podcasting service
Microconf
Rob Walling

Jun 28, 2018 • 34min
47: Pacing Yourself When Starting Up
Despite being in the process of building new companies and products, Derrick and Ben understand the importance of sustainable pace - being able to unplug and get some rest to make smart decisions. So, Derrick just got back from vacation, and Ben plans to take some days off soon. It’s about the mental component of mastering your brain.
Derrick is getting back into the swing of things and trying to finish the mock-ups for communication flows inside Level. Ben has been focusing on filling up Tuple’s alpha and booking substantial pre-pays. Also, Ben shipped his landing page and already has about 12,000 subscribers.
Today’s Topics Include:
Moving away from crud and crappy versions, and switching to a fully native app
Reaching a certain bar to get the product in users’ hand; adjust and pivot as needed and be a suitable alternative
Making a decision whether to build in Electron or not
Is a desktop app necessary? Always-open option can lead to missed productivity
KPI dashboard - what gets measured, gets managed
Restart of code quality challenge: Sign up for next cohort in July
Following challenge, pitch people on paid pair programming course
Buying time to make a product really good, and training next generation of customers
Business Idea: CEOs need dashboards
5-Minute Journal: I’m grateful for, what would make today great, and I am…; and 3 amazing things that happened today and how could I have made today even better
Links and resources:
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
Derrick Reimer on Full Stack Radio - Designing a Calmer Team Communication Platform
Electron

Jun 14, 2018 • 1h 6min
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!
Today’s Topics Include:
Should I learn more programming? More design? Acquire skills to connect the two
It’s easier to build something after building relationships; a personal approach makes you stand out
Can connection with core audience become a scalable competitive advantage?
Ways to tell your story and generate followers before you have product info available
Get your product into the hands of potential users
Propensity that you know all the answers, but bury your ego and ask for help
Deciding how much to charge, pricing structure
You can get people to sign up and get them to pay for it, but can you get them to use it and keep using it?
Invest in something that offers a virtuous cycle of revenue back to your company
Demonstrate value of existing content; making money and conversions from specific campaigns and activities
Fears and feelings when people are not using a product
Hire customer support people to reach out to customers and generate revenue
Trend is automated software companies, but the most successful companies emphasize a human service component
Pair programming always bubbles to the surface
Links and resources:
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Justin Jackson
Justin Jackson on Twitter
Level
Build Your Saas podcast
Transistor.fm
MicroConf
Jason Fried
Seth Godin
RightMessage
How We’ve Taken FOMO 20k to 80k by Justin Mares

Jun 7, 2018 • 41min
45: The Value of Teaching
He’s back! Ben returns from traveling to Hong Kong. He shared his rails knowledge by helping someone who is building a business and using a rails app. He made performance improvements and refactored items. Derrick is also doing some Vim tutoring. Learning something new does not take long or a lot of money, and gets easier.
Of course, both Ben and Derrick continue to work on their new products, as well. Derrick is creating Level, an open source team communication and management tool. Ben is starting Tuple, a pair programming tool alternative for Screenhero.
Today’s Topics Include:
How to do file browser for projects in Vim: CtrlP; baked-in and plug-ins options for Vim
Build and code, but talking to customers can impact your course and business
Derrick is posting small, hot tips on Twitter that are nuggets of valuable knowledge
Likes and retweets growing Derrick’s number of followers
Ben needs to tweet more to market to developers for his new product - Tuple
Derrick continues to work on Level; categorizing communication and how to present it
Notion of urgency is big issue with Slack that Derrick needs to address with Level
Brainstorming sometimes needs conversation, and sometimes long periods of silence
Controlling distractions and creating checklists are part of Derrick’s daily routine
Derrick is improving the copywriting and calls to action on Level’s landing page
Ben plans to incentivize people via annual plan upsells
Derrick is considering a referral tracking mechanism as an incentive
Big transitions and uncertainty generate anxiety for Ben, but he now has strategies to deal with it
Trying to create a thing that did not exist before is different than something that already exists; it is harder and more stressful, and you’ll feel pain and be unsure
Ben’s role as external-facing sales and marketing vs. product development and coding
Structuring to make yourself happy, but keeping staff happy, too; everyone should like what they are doing
Links and resources:
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Vim
CtrlP
Your First vimrc Should be Nearly Empty
Thoughtbot
MicroConf
Momentum
Mathias Meyer
Reboot Podcast - How You Walk Through the World with Seth Godin

May 31, 2018 • 26min
44: Exploring the Open Source Business Model
Rob Walling, co-founder at Drip, MicroConf organizer, and host of the Startups For the Rest of Us podcast, continues to co-host with Derrick while Ben is in Hong Kong. Rob is becoming a believer in 3 to 6 hour work days; he is more productive and has more motivation to get things done.
As for Derrick, he read an article titled, After 5 years and $3M, here’s everything we’ve learned from building Ghost, which relates to the business model he is following for his Level product. Ghost is using the open source core product and it’s bootstrapped, which can be difficult. in this episode, Derrick pulls out a few pieces of the article that are relevant to share.
Today’s Topics Include:
Piece 1: Competing on convenience with centralized platforms was a mistake; took too much time and made it a difficult experience for end users
Level customers will either pay or go to the open source version; if they find that self-host vs. buy does not work out, there will be a transition path
Piece 2: Building a distributed team is both easier and harder than imagined; the biggest challenges came from human problems, not business problems
Drip experienced similar issues with a distributed team; Level will probably have a distributed team to find talent but not be able to compete with bigger companies
Pros and cons of remote- vs. office-based teams, such as building camaraderie
Piece 3: Open source development is more broken than ever; you are criticized for not doing something or meeting certain standards
Derrick plans to set expectations up front and promote opportunities for integration; be transparent and provide value
Brand is recognition within a group of people; brand association can be positive when they trust you, but negative if the brand treats them badly
Drive word of mouth; it is one of the biggest attraction channels for companies
Links and resources:
Rob Walling on Twitter
Startups for the Rest of Us
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
MicroConf
Drip
After 5 years and $3M, here’s everything we’ve learned from building Ghost
Build Your Saas Podcast
SaaStr

May 24, 2018 • 40min
43: Strategizing Product Validation
Rob Walling joins Derrick once again as a guest co-host while Ben is traveling in Hong Kong. Rob was Derrick's co-founder at Drip, runs MicroConf, and hosts the Startups For the Rest of Us podcast.
Derrick and Rob discuss the latest Level updates and strategize how best to approach previewing product mockups to potential customers. They discuss how the early phase of a startup is very fulfilling because you can be very creative, but also stressful because of risk and uncertainty. Rob gets Derrick's feedback about offering one-on-one founder consulting in his spare time.
Links and resources:
Rob Walling on Twitter
Startups for the Rest of Us
Derrick Reimer Website
Derrick Reimer on Twitter
MicroConf
Ben Orenstein Website
Ben Orenstein on Twitter
Level Live #3: A Fireside Chat with Rob Walling
Drip
Twist
Basecamp
Soylent

May 17, 2018 • 1h 1min
42: Fostering a Culture of Creativity with Rob Walling
Ben is away, so Derrick invited a special guest for this episode. Rob Walling was the co-founder of Drip and is the co-host of MicroConf. Rob recently removed Slack from his phone, and is waiting for Derrick’s Level product.
Level is an open source team communication tool that Derrick hopes will replace Slack among software teams. Others are looking forward to Level, as well, and wondering how many clients Level is going to be available on: Mobile, desktop...As Derrick continues to work on Level, the two also reminisce about their days together at Drip.
Today’s Topics Include:
Derrick is planning to use Electron to build a desktop app for Level
Some follow a pure approach and go native, but it can be more difficult than expected
Bursting and psychological safety concepts allow people to express their ideas
What if? Be creative as a team, encourage everyone to collaborate, and make the environment comfortable for magic to happen
Individual vs. group brainstorming: Which works better? How do other companies do it?
Derrick plans to show polished, not raw sketches of Level to make it reviewable
Derrick has been building the product, writing code, nuking the database, and creating videos to show slices of Level being made
Derrick used Stripe Atlas to form an LLC for Level
Stripe is inspiring; believe that you can transition an industry, make things happen, and win the hearts and minds of developers
Derrick and Rob discuss the pros/cons of fundstrapping vs. bootstrapping
Rob shares feedback and reviews from listeners of his podcast
Rob and Derrick share their thoughts on cryptocurrency investing
If you’re enjoying the show please give us your ratings and reviews in iTunes.
Links and resources:
Rob Walling on Twitter
Startups for the Rest of Us
Derrick Reimer Website
Derrick Reimer on Twitter
MicroConf
Ben Orenstein Website
Ben Orenstein on Twitter
Electron
PhoneGap
Twist
WorkLife podcast
Gusto
Zenefits
The Pixar Touch
Lost and Founder by Rand Fishkin

May 10, 2018 • 32min
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.
Derrick especially enjoyed copywriting and injecting humor sessions. Ben was impressed, too. His favorite talk was from Justin Mares on “How We’ve Taken FOMO 20 to 80k MRR in 18 Months,” where Mares talked about a difficult task and what worked and didn’t.
Today’s Topics Include:
Show up every day and try to make your business better
Growth regrets and scaling challenges for Derrick with Drip; does slow and steady win the race?
Growth and Derrick’s new product Level; he plans to focus in on software developers
Don’t be afraid to go into large markets with your products and services to grow
Ben met up with the “guy” whose research he is using for his new company and the problems he plans to tackle
Ben plans to use WebRTC, unless or until an alternative appears
Ben has been thinking about positioning, and how it will affect his UX, pricing, and other factors
Ben settled on a name for his new business: Tuple (it was meant to be and nerdy enough for developers to get it)
Derrick battles for domains and wins Level.app
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
MicroConf
Drip
WebRTC