

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

Aug 22, 2019 • 1h 3min
100: A Cool 100th Episode: Celebrating With Our Past Guests
One of the benefits of having a podcast is being able to interview interesting people. Being a podcast guest is the best gig in the universe. Spew some knowledge, or just ramble.
It’s time to celebrate the 100th episode of the Art of Product (AoP) podcast by catching up with previous guests to share updates and what’s next. Thanks for listening!
Today’s Topics Include:
Julian Shapiro: Running the growth agency, Bell Curve, was not rewarding but stressful; pivoted to Demand Curve to offer training to grow companies and teams
Jason Cohen: Busy because of WP Engine’s multiple acquisitions, including buying Flywheel; he describes how acquisition accelerates or de-risks successful strategies
Rob Walling: TinySeed continues to thrive and fun to work with ambitious and motivated founders building things; MicroConf moves from Vegas to Minneapolis in April 2020
Paul Jarvis: Re-recording videos and audio for MailChimp course and rebuilding Fathom
Rahul Vohra: Superhuman achieved Series B and added employees; working on mental health and wellness by getting a super-sweet and super-dependent puppy
Steve Schoger: Recycled redesigned Tuple site at Laracon and now working on Tailwind UI with Adam Wathan
Links and resources:
AoP Episode 61: Unconventional Growth Tactics with Julian Shapiro
Julian Shapiro
Demand Curve
Bell Curve
Y Combinator
AoP Episode 69: Sound, Actionable Advice with Jason Cohen
WP Engine
Flywheel
Jason Cohen - Designing the Ideal Bootstrapped Business
SmartBear
A Smart Bear Blog
AoP Episode 66: TinySeed Updates with Rob Walling
Rob Walling
TinySeed
Startups for the Rest of Us
MicroConf
Out of Beta Podcast: The first TinySeed founder retreat
AoP Episode 93: Company of One with Paul Jarvis
Paul Jarvis
Company of One
MailChimp Course
Fathom
Camtasia
AoP Episode 91: Feeling Superhuman with Rahul Vohra
Superhuman
Headway
AoP Episode 70: Refactoring UI: Concept to Launch
Steve Schoger - Refactoring UI: Tuple
Laracon
Justin Jackson’s Transistor
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Tuple
Tuple’s Pair Programming Guide
StaticKit
Level
Level Retrospective
Level Manifesto

Aug 15, 2019 • 26min
99: The Binge Is Real, Countdown to the 100th Episode
There’s no need to ask them who they are, what they do, businesses and products they built because listeners know them through their stories. After a lot of random, but worthwhile conversations, they’re getting good at being podcast co-hosts.
How long does it take to listen to all episodes of Ben and Derrick’s Art of Product (AoP) podcast? Who knew it would be binge-worthy? One more down, one to go before they reach Episode 100!
Today’s Topics Include:
Tuple 1.0: App is available, despite instant self-serve checkout setback
Tuple customers are expanding their use, but there’s still room for more users
One-time lump sum: Tuple pricing model that makes sense
StaticKit Beta: Start small with kernel of a product to keep funnel constrained
Marketing Research and Product Risk: StaticKit to stand on its own or grow
Drip and Deleted Emails: Save copies to maintain confidence in critical path
Negative Churn: Influence users to upgrade pricing for expansion revenue
Links and resources:
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Tuple
Tuple’s Pair Programming Guide
StaticKit
Level
Level Retrospective
Level Manifesto
Giant Robots Podcast
Steve Schoger
Userlist
Adam Wathan on Twitter
Tailwind CSS
Product Hunt
Ray Ozzie
WordPress
Drip
Refactoring Rails

Aug 8, 2019 • 37min
98: Adam Covers for Derrick
Derrick’s short notice about not co-hosting this episode because of being on a plane, and Ben not knowing or planning what to discuss, who and what’s left?
Updates and reports on Tuple and Tailwind. Welcome back Adam Wathan!
Today’s Topics Include:
Today’s Trend: Advisor/investor/founder journals and reports of accomplishments
Serves as a way to stay in touch, build relationships, ask questions, and get feedback
Three Tuple Reports Later: Things are still going good
Programming meets Business: Gary Bernhardt commits to being future podcast guest
Successful Tuple Shipments: Significant use of Webcam feature
Pricing Options: Ben expresses concern over free trials or pre-paid plans to capture credit cards and emails
Invite-only vs. Public Launch: Continue as is, or open Tuple up to all
Tuple Update: Revenue is growing quickly, receiving 70-100 support tickets weekly, and room to add customers
Tailwind Update: Adam launched first set of videos for Tailwind CSS course
Tailwind Subscription/Price Structure: Yet to be determined
Adam’s Prediction: Education and documentation determine open source winner
Links and resources:
Adam Wathan on Twitter
Full Stack Radio
Tailwind CSS
Refactoring UI by Adam Wathan and Steve Schoger
Steve Schoger
Tyler Tringas on Twitter
Brian Casel
Gary Bernhardt on Twitter
ExecuteProgram.com
David Heinemeier Hansson (DHH) on Twitter
Giant Robots Episode 26: Deep into the psyche of Gary Bernhardt
Giant Robots Episode 27: Fabulous new mistakes with Joe Ferris
Giant Robots Episode 28: Farther, further, faster with David Heinemeier Hansson
Node.js
React
Ruby on Rails
Zoom
Superhuman
Screenhero
Slack
GitHub
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Tuple
Tuple’s Pair Programming Guide
StaticKit
Level
Level Retrospective
Level Manifesto

Aug 1, 2019 • 29min
97: To Build, or Not to Build - Jane Portman of Userlist
While Ben’s on vacation, Derrick welcomes another podcast host who can commiserate with him about email automation.
Jane Portman is a UI/UX expert and consultant who hosts the UI Breakfast Podcast and co-founded Userlist.io. She describes what it takes to create a customer messaging tool.
Today’s Topics Include:
Product Priorities: Slow, steady, and quality
Lifestyle Business: Overall goal is to replace consulting with SaaS recurring revenue
Challenges: Limited development time and resources; slow growth rate to adopt mission-critical product
To Build, or Not to Build: Avoid feature creep by focusing on what to add or improve
Playbook Post: 10 steps to successfully position a product
Launch Process: People are waiting for the right time for the right tool for their business
Customer Conversations: Pre-product interviews about problem to be solved; followed by product demos to grant access to beta version for feedback
Finding Customers: Landing page, updates, stories, sign-ups, mailing list, and more
We’re out of Beta! Simple and straight-forward product launch plan and strategy
Generic Illustrations: Product design trend that has to end
Email Experiences: Educate people on how to ethically use email to serve their business
Links and resources:
User Onboarding: The Ultimate Guide for SaaS Founders
UI Breakfast Podcast
Userlist.io
UI Breakfast on Twitter
Userlist.io on Twitter
Behind the Scenes of Our Upcoming Public Launch
How We Used April Dunford’s 10-Step Method to Overhaul Positioning at Userlist
AoP Episode 91: Feeling Superhuman with Rahul Vohra
Product Hunt
Hacker News
Drip
MailChimp
Humans of Flat Design on Twitter
Paul Jarvis
MicroConf
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Tuple
Tuple’s Pair Programming Guide
StaticKit
Level
Level Retrospective
Level Manifesto

Jul 25, 2019 • 33min
96: Tuple Official Launch and Taking Time to Unplug
Is something bugging you? Need to get away from everything? Derrick can’t wait to once again ride rugged waters on Minnesota’s many lakes. Not unlike startups, it isn’t always easy to stay afloat when under pressure.
Heeelllloooo! Are you there? Still interested? Ask and you shall receive. Ben shipped a major feature for Tuple. Drumroll please…video support. I’ll Tuple you!
Today’s Topics Include:
Sensible Deprivation: Some suffering can be good; makes you appreciate things more
Get Over It, and Gain Confidence: Design and develop video support prototype
Official Launch Date for Tuple: Some time in August; Ben’s still trying to shake the perception he’s charging people for beta product
Security Vulnerabilities Happen: Ben’s reaction to recent issues with Zoom and Slack
Mistakes Ben Might Make: Free Tuple trial to increase conversion and expansion
Derrick’s Building Product: Initial version of StaticKit and form collection component
Security ROI: Short-circuiting pushback with strong write-up for SOC 2 and ISO 27001
3+ Tuple team? Someday, Ben wants to hire a part-time designer and developer
Links and resources:
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Tuple
Tuple’s Pair Programming Guide
StaticKit
Level
Level Retrospective
Level Manifesto
Outward Bound
Zoom
Superhuman
Slack
Adam Watham
Steve Schoger
Laracon
Elm
React
Jekyll
Drip
IS0 27001
SOC 2
HackerOne

Jul 11, 2019 • 44min
95: What Really Happened to Screenhero
While Derrick is away, Ben welcomes Don Goodman-Wilson, who was the first hire at Screenhero in 2013.
Don shares his version of Screenhero’s incredible journey, its migration to Slack, and Tuple coming to the rescue. Better late than never!
Today’s Topics Include:
Work Ethic/Culture: Doctorate in philosophy requires logic and dedication
Engineering Challenges: Learning low-level C/C++ code in Screenhero product
Microsoft Windows and Apple Mac: Harmonizing code bases
Web Application Programming: User interface (UI), reliability, latency, quality, and billing
Product/Market Fit: Quick growth, adoption, and implementation of Screenhero
Pair Programming: Personal and professional sharing and collaboration
Second Day at First Expo: Atlassian’s interest, followed by Slack’s acquisition
Platform of Choice: Who’s the best partner to work with to achieve Screenhero’s goals?
In and Out of the Sandbox: Screenhero’s prone to crashing and uses private APIs
Slack destroyed Screenhero: Expectations and compromises created culture clash
Heartbreaking, Rational Reality: Removal of remote screen control in Slack calls
Maintainerati’s Mission: Understand challenges and offer solutions for maintaining open source software
Links and resources:
Don Goodman-Wilson
Don Goodman-Wilson on LinkedIn
Maintainerati
Screenhero
Y Combinator
Slack
The Screenhero Story - The Screenhero Blog
Removal of remote screen control in Slack calls
Atlassian
HipChat
WebRTC
Redis
Python
Stripe
Ractive.js
Ruby-Grape Rack
Ruby on Rails
Dropbox
Google Hangouts
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Maintainerati on Twitter
Tuple
Tuple’s Pair Programming Guide
StaticKit
Level
Level Retrospective
Level Manifesto

Jul 4, 2019 • 34min
94: Seeking Clarity
Summer is in full swing. Ben spent a fun and productive day talking about work at a Red Sox game. It was an own-your-own business startup moment.
Derrick can see clearly now, thanks to SMILE laser eye surgery. But he’s still seeking clarity on whether to make the masses happy, or stick to core concerns to attract specific customers when creating a new product.
Today’s Topics Include:
Tuple Grows Up: New version of marketing site getting ready to launch
Cha Ching: Confirmation of biggest single Tuple invoice sent for payment
How much wisdom is there in the crowd? Can you trust it?
Remote Control: Tuple customers give up control to use driver/navigator pairing
Self-serve Sign-up: Tuple strives for automation, learning, and feedback
Time for a Truce: Trash talking, name calling stops for Slack to send customers to Tuple
Soon to be released: Derrick’s StaticKit, a modern approach for embedding dynamic forms onto static sites
Links and resources:
StaticKit
Art of Product Podcast Episode 91: Feeling Superhuman with Rahul Vohra
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Tuple
Tuple’s Pair Programming Guide
Level
Level Retrospective
Level Manifesto
Jekyll
Middleman
Gatsby
Hugo
Next
React
Superhuman Product-Market Fit Survey
Drip
Steve Schoger
Stripe
MicroConf
Slack
Removal of remote screen control in Slack calls
Screenhero
Netlify
Zeit
Mailchimp
ConvertKit
JSON
Zapier
FormKeep
Heroku
Ruby on Rails
Medium
Phoenix

Jun 27, 2019 • 49min
93: Company of One with Paul Jarvis
After a QuickTime error eradicated Paul Jarvis’s conversation with Ben and Derrick for an Art of Product episode, he’s back with an update on his recently published book, Company of One.
Should Paul strike while the iron is hot? Despite the book’s success and being encouraged to write another one, Paul wants to take a necessary break before proposing a new book idea.
Today’s Topics Include:
Legally Binding Thumbs-up Emoji: How Paul sold rights for book to be in 13 languages
Break between Building: Frustration of figuring things out, replaced with hammock thinking and relaxation
Paul’s writing process fills fountain of ideas; ready to do a book on digital privacy
Slack Support Group: Help yourself and others
Level Failure Leads to Filtering Idea Criteria: Shouldn’t be mission-critical product; require more than a few decision makers; and native apps shouldn’t be a minimum requirement
Company of One: Doesn’t necessarily refer to one person, but mindset
Balance between technology you know and learning curve for something you don’t
Software as a Service (SaaS) Business: Scale up or stay small?
Derrick describes Company of One as what he aspires toward, but is open to possibility of co-founders
Nothing Lasts Forever: Question growth, not stagnation
Seek and scale support, especially when using third-party software
Drumroll, Please: Ben announced plans for public launch of Tuple in August 2019
Links and resources:
Paul Jarvis
Company of One
Company of One (Co1) Academy
Company of One Podcast
Fathom
Paul Jarvis on Twitter
Paul Jarvis’s WPComplete Plugin
Ingenx
The Year of Living Biblically by A.J. Jacobs
Slack
Screenhero
Rob Walling
Drip
Finding My Next Bootstrapped Business Idea
DigitalOcean
Heroku
Ruby on Rails
Phoenix
Superhuman
Hacker News
Art of Product Podcast Episode 91: Feeling Superhuman with Rahul Vohra
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Tuple
Level
Level Retrospective
Level Manifesto

Jun 20, 2019 • 30min
92: Slack Leaves the Market
The world received amazing news in the form of a great gift: Slack is making a major change in the market—it’s leaving!
Ben and Derrick share their thoughts on Slack’s reasonable and rational decision to remove remote control functionality. What happens now? Try Tuple! Just sayin’, actually that’s what Tuple customers are suggesting.
Today’s Topics Include:
Improve Slack Calls: Reason for removing rarely used remote control feature
Kicking marketing machine into gear: Customers’ kind words generated surge in requests for access to Tuple
Slack and Screenhero Saga: Complete story of acquisition and pair programming will probably never be told
Keep shipping, swinging, and taking shots by increasing luck surface area and learning from previous successes and failures
Dear Dvorak user, is it time to switch? Tuple’s shipping international keyboard support
Big deals keep coming in for Ben; it’s great to sometimes say, “No”
Derrick’s writing cadence continues; flattered by onslaught of positivity from people
Product/Founder Fit: Be passionate about product or business before building it
Pressure to be Perfect: Don’t sweat the small stuff, just the details
Links and resources:
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Just Keep Shipping by Derrick Reimer
Ben Orenstein Website
Ben Orenstein on Twitter
Tuple
Tuple’s Pair Programming Guide
Level
Level Retrospective
Slack
Removal of remote screen control in Slack calls
Screenhero
Drip
Zoom
GitHub
The Dvorak Keyboard
Adam Watham

Jun 13, 2019 • 42min
91: Feeling Superhuman with Rahul Vohra
Derrick’s feeling “superhuman.” Fortunately, he’s a user and lover of the Superhuman product. Maybe that’s why today’s guest is Rahul Vohra, co-founder and CEO of Superhuman.
Today’s Topics Include:
Reason for Superhuman still being invite-only is not to increase user demand
Sustainable Word-of-Mouth Growth Engine: If you don’t pick the users, you can’t responsibly work on their feedback
Purpose of Product and Target Audience: Email is work, and work is email; designed to be meaningful and life changing for high-volume email senders
Startup Details: Deliberately think through and consider everything deeply from scratch
Don’t turn down money when bootstrapping to find perfect product market/customer fit
Knack for knowing what people want, before they know they want something; and helping people realize they want something
Without active or spending money on marketing, Superhuman’s waitlist keeps growing
Superhuman’s Values: Create delight, be intentional, and remarkable quality
Best founders, including Rahul, are unstoppable forces of nature; they leave debris and destruction in their wake
Time tracking a day in the life of Rahul: 40% managery; 20% recruiting; 14% fundraising; and 11% product, community engagement, and deep thoughts
Superhuman’s pricing is low, but generates high value; big fan of round numbers
Business and product metrics: Activation, seat churn, net dollar churn, speed, and reliability rates
Objective: Refine entire Superhuman experience to exhibit remarkable levels of quality through three key results - ARR, hiring, and product sentiment
Generate roadmap and find balance to maintain lead over market and continue to grow
Startup Growth: Pick weekly growth rate; you don’t have to grow faster than you want to
Links and resources:
Superhuman
Rahul Vohra on LinkedIn
Rahul Vohra on Twitter
Rahul Vohra’s Email
Superhuman Product-Market Fit Survey
Rahul Vohra on This Week in Startups with Jason McCabe Calacanis
Rapportive
TechCrunch
Product Hunt
Hacker News
Google Docs
GitHub
Startup = Growth - Paul Graham
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Level Retrospective
Level Manifesto
Tuple