

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

Nov 7, 2019 • 30min
110: The Importance of Mentors
Derrick shipped config file for StaticKit’s UI migration and shifted his focus to other areas of the product. He plans to deliberately and consistently test email messages to determine which generate response and interest in StaticKit. He continues to connect with TinySeed mentors.
Ben understands the value mentors offer in helping entrepreneurs easily avoid bad ideas and pursue good ones. Also, he’s working on writing content for his October advisor update. What’s the next step following Tuple’s free trial? T-shirt? Should Ben think bigger and Shape Up?

Oct 31, 2019 • 28min
109: Split Test = Optimization
Some podcasts present terrible sound quality, yet garner tons of listeners. Ben and Derrick are professionals, and care about the sound quality of their AoP podcast episodes.
Despite audio difficulties, Ben and Derrick are back. They sound good, and they’re ready to rock their updates on StaticKit and Tuple!
Today’s Topics Include:
Should you test? Trust weak data? Split-test customer email messaging tools should push you to test as default path
(Not) Steady State of New Trials: Email blast offering free Tuple trial to everybody
Tuple T-shirt Prototype: Take the next step in funnel to pay for Tuple to get T-shirt
Structure and Process: Sense of energy from Tuple’s stand ups and status updates
Tuple to handle classic startup chaos by reading, Shape Up: Stop Running in Circles and Ship Work that Matters by Ryan Singer
StaticKit Solopreneur: Derrick’s suffering from decision fatigue, struggling to juggle multiple tasks, and balancing building a great product and connecting with customers
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
TinySeed
Using Tailwind CSS with Next.js
Level
Audio-Technica ATR2100 USB
Drip
Shape Up
JAMstack Conf
Slack

Oct 24, 2019 • 37min
108: Getting Back to Growth Planning
Derrick returned from JAMstack Conf with a jolt of energy and excitement thanks to face-to-face conversations and strategic connections with potential StaticKit customers.
Ben expressed interest in once again speaking at developer conferences. After all, he has plenty of worthwhile information and lessons learned to share about Tuple.
Today’s Topics Include:
Frontend and Backend: Considerations for implementation/migration with StaticKit
Main Objective at JAMstack: Market validation, not to make sales to customers
Future Feature: Allows people to configure StaticKit account via config file
Prevent UI Creep and Wall of Fields: Keep it elegant, but flexible and customizable
Instant Gratification and Relief: Numbers are rising again after Tuple’s sign-up fluctuation
Tuple Trick: Free, two-week trial for submitting email via invite box; stabilization and scaling are serious concerns due to more customers
Ben’s optimism leads to deleted tweet about Tuple T-shirts
How much MMR is enough? Never enough; bigger, brighter, more interesting future
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
TinySeed
Using Tailwind CSS with Next.js
JAMstack Conf
MicroConf
Slack
Netlify
WordPress
Drupal
JSON
Drip
Justin Jackson
Shopify
Rob Walling
Paul Jarvis
Jason Fried

Oct 17, 2019 • 27min
107: Becoming a Multi-Product Company (with Amir Salihefendić)
Derrick and Ben welcome Amir Salihefendić, founder and CEO of Doist. Ben was able to break away from Slack and uses Doist’s Twist app at Tuple for team communication.
Also, Ben and Derrick share updates and experiences about their businesses that spark familiarity and advice from Amir based on his entrepreneurial adventures.
Today’s Topics Include:
Founder Therapy: Derrick helped talk Ben off the ledge and figure things out with Tuple
Live and Learn: An entrepreneur starting a business is on a psychology rollercoaster
Ben’s path forward to break past lull via positive momentum and mood
Short-and-Simple Answer: Derrick should only focus on long-term goals for StaticKit
Looking forward to new release of Todoist in a few weeks? New features added with emphasis on improving existing design and workflow
360 Review: Stop doing development, and focus time on CEO role and responsibilities
Balancing Act: Difficult to start companies and launch multiple products; but worth long-term investment and effort
Unless your target audience is college students and you enjoy fighting churn, Doist’s pricing strategy isn’t recommended
Synchronous vs. Asynchronous: Working remotely may impact your mental health
Links and resources:
Doist
Twist
Todoist
Success Ten Years in the Making with Amir Salihefendic of Doist
Slack
Rob Walling
Fooled by Randomness
Tyler Tringus
Nathan Barry
MicroConf
Drip
jQuery
Adam Wathan
WeWork
Out of Beta Podcast
Bootstrapped Web Podcast
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
TinySeed
Using Tailwind CSS with Next.js
Level

Oct 10, 2019 • 34min
106: Creating Growth Key Metrics
Derrick spent his birthday at the north shore of Lake Superior to disconnect and getaway. Yet, he found some time to brainstorm and problem solve for StaticKit.
Ben’s back from Martha’s Vineyard, only to experience less positive updates for Tuple. For the first time, Tuple is shockingly “in the red” financially. So, he feels guilty about going away.
Today’s Topics Include:
Slow Growth: Substantially fewer Tuple trial signups than previous time periods
Marketing and Sales Strategy: From being the new tool on the block to steady state where Ben has to earn new Tuple customers
Bullseye Framework: Derrick re-read his go-to startup guide to select StaticKit’s repeatable traction channels
Tuple’s Q4 objectives and key results (OKRs): Fill top of funnel to increase new email subscribers and trials to continue to grow
Ben’s future plans to gather marketing and sales information/intelligence by advertising and appearing on dev-related podcasts
Design Matters: Impacts people’s perception of product and builds trust
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
Using Tailwind CSS with Next.js
Level
Slack
Zoom
Upcase by Thoughtbot
Traction: A Startup Guide to Getting Customers by Gabriel Weinberg and Justin Mares
Ruby on Rails
HubSpot
Rob Walling
Drip
Adam Wathan
Full Stack Radio
Syntax.fm
Steve Schoger
Elixir
Recurly
Chargify

Oct 3, 2019 • 24min
105: Exploring Freemium
Ben is living his best life with walks on the beach and wonderful weather. On the Tuple side, he shipped some code, got a pull request (PR) merged, and is now on the devise authentication gem.
Derrick’s been busy, too. StaticKit’s official integration with ZEIT went live. ZEIT is one of two major hosting providers in the static site ecosystem. Also, an initiative with Zapier is in the works.
Today’s Topics Include:
Derrick did it his way: Integrations can be a powerful marketing channel
Zapier Integration: Derrick’s waiting on approval to be listed publicly in its directory
Positive Pace: Derrick invests his previous product efforts with marketing impact
Pricing Pros and Cons: Free vs. paid tiers for forms or submissions per Website
Personal Response: Derrick receives notification when someone new signs up with StaticKit to offer support
Derrick joined TinySeed, a startup accelerator that helps bootstrappers grow their company faster through funds
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
Using Tailwind CSS with Next.js
Level
Devise Authentication Gem
ZEIT
Zapier
Netlify
FormKeep
Salesforce
Slack
Adam Wathan
Superhuman
Drip
TinySeed
JAMstack Conf

Sep 26, 2019 • 33min
104: Tiny Conferences, and Business Growth Challenges
Ben is finding it easier to plan meetings to talk about challenges, and how he appreciates consistency. He describes his recent experiences with NanoConf and TupleConf.
Derrick understands how perspectives shift as a business goes through different stages. Everyone wants financial security, but they always have complicated problems to solve.
Today’s Topics Include:
Mini Mastermind Conferences: Growth Strategy for building rapport and trust while bringing in new people for new perspectives
Lessons Learned: Capture what went well, what should change in the future
TupleConf: Ben, Joel, and Spencer discussed high-level questions and risk of co-founder issues and ambitions
How to Deal with Conflict: Know your strengths, weaknesses, and personality type
Planning and Prioritization: How to clarify and activate energy to do lower/smaller tasks
StaticKit Milestones: Derrick achieved expansion revenue, additional customers, and annual renewals
Pricing Structure, Tiers, and Upgrades: Monthly vs.yearly subscriptions with no surprises
Derrick shares future vision of StaticKit beyond static forms for positive user experience
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
Using Tailwind CSS with Next.js
Level
Big Snow Tiny Conf
Build Your SaaS Podcast
CartHook
Brian Casel
WordPress
Gatsby
Jekyll
Drip
Netlify
Stripe
GitHub

Sep 12, 2019 • 35min
103: Code Quality and Balancing TDD
Ben’s been adding variety to work by biking to breakfast and the beach, while working in-between during his stay on Martha’s Vineyard. He’s feeling lucky to work remotely, and still be able to connect with co-founders!
Derrick enjoys a change of scenery from time-to-time during workdays, especially to kickstart his blood flow during an afternoon lull or breaking point.
Today’s Topics Include:
Writing code is like riding a bike: Tuple moving forward with adding single sign-on
Caring about Code Quality: Ben’s higher level tests prove more valuable, less coupled
Evolution of Testing: Derrick’s progress from test-driven development (TTD) to practical testing for StaticKit’s structure and features
Devise Deal Breaker: Digested passwords in Tuple database wouldn’t need to be reset
Pair programming proves powerful in preventing mistakes and being blocked
Marketer? Developer? Sales? Ben’s possible future role and responsibilities with Tuple
Hockeystick Metrics: First-paying StaticKit customer leads to 200% growth increase
Content Marketing: Using Tailwind CSS with Next.js spikes StaticKit sign ups
Self-serve Engine: Easily upgrade and deploy StaticKit from sandbox to live mode
Prioritize Priorities: Ben encourages Derrick to focus on forms for StaticKit
AoP Podcast: Is fanbase willing to pay for extra-special content? Share ideas with Ben and Derrick via Twitter
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
Using Tailwind CSS with Next.js
Level
AoP Episode 22: Finishing the Year Strong
Tailwind CSS
Next.js
Rob Walling
Drip
Security Assertion Markup Language (SAML)
Ruby on Rails
Thoughtbot
RubyGems
Devise
DigitalOcean
JSON

Sep 5, 2019 • 27min
102: Single Sign On (SSO) for Tuple?
The true life of an entrepreneur! From backgrounds to beards, change is in the air for both Ben and Derrick. Ben is a 36-year-old man who is back living with his parents temporarily to save some cash. Ben considered himself a minimalist, until he realized just how much stuff he had to move. So, he hired movers.
Derrick describes the importance of documenting lessons learned and accumulating knowledge. As a result, he got his first paying customer for StaticKit. A meager $10 in revenue is greater than zero.
Today’s Topics Include:
Tuple: All for One, or One for All? Ben seeks advice on whether to make significant changes to app to satisfy single prospect that requires single sign-on (SSO) support
Authentication and Security Schemes: Increasing scope intimidates and impacts legacy engineering decisions
Big Decisions equal Big Bucks: Good but challenging problem to have in business
Free to paid options for Derrick’s StaticKit turns into inflexible data model
Got one, get more: Freemium customer converts to first StaticKit paid subscriber
Derrick’s Next Step with StaticKit: Default state of being sustainable and breaking even on personal expenses
Solo Founder: Tricky to find good fit of founder to do everything and grow quickly
Keep Shipping Away: Set weekly goals to achieve and celebrate wins
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
G Suite
Security Assertion Markup Language (SAML)
Basecamp Shape Up
Thoughtbot
RubyGems
Ruby on Rails
Drip
Stripe
React

Aug 29, 2019 • 32min
101: Mentorship Momentum with Matt Wensing of SimSaaS
While Ben’s on vacation, Derrick welcomes Matt Wensing, founder of SimSaaS and co-host of the Out of Beta podcast. Matt was also the co-founder and CEO of Stormpulse.
Derrick credits Matt for giving him great advice to make the winding down of Level less daunting. Now, Derrick’s on the upswing of rebuilding his confidence, despite challenging cluster headaches and stress cannibalising productivity.
Today’s Topics Include:
Out of Beta: Matt’s new podcast where he publicly discusses projects and products
Mentorship Momentum: Seek help to sharpen software as a service (SaaS) skills
Matt’s focused on marketing efforts to get work done and sales to gain access
What is launching? Get started for free!
TinySeed, Big Benefits: Solo business can’t do it alone; community plays a big role
Fruitful Conversations: StaticKit update involves JavaScript, APIs, and Markup (JAMStack)
Links and resources:
Matt Wensing on Twitter
Matt Wensing on LinkedIn
SimSaaS
Riskpulse
Out of Beta Podcast
Stormpulse
SimSaaS on TinySeed
MicroConf
MicroConf Europe
Brian Casel
Rob Walling
Jason Cohen
Company of One by Paul Jarvis
Slack
Heroku
CI/CD for WordPress with Peter Suhm of Branch CI
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