

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 30, 2019 • 48min
90: The Mom Test with Rob Fitzpatrick
Ben and Derrick welcome Rob Fitzpatrick, author of The Mom Test: How to talk to customers and learn if your business is a good idea when everyone is lying to you. It’s not your typical non-fiction business book, but short and straight to the point. It should be a mandatory prerequisite for anyone embarking on the startup journey.
Derrick’s Level Retrospective describes how Rob’s book had a major impact on his most recent startup experience. People want to be supportive, so it’s difficult to get unbiased feedback during customer validation. Derrick already knew this to be correct, but underestimated the degree to which everyone lies. So, he felt betrayed by early validation efforts proved to be radically different from reality.
Today’s Topics Include:
Don’t ask anyone if your business is a good idea because everyone is biased
Burden of truth should be put on yourself, not your customers
Entrepreneur’s Superpower: Getting support before it’s deserved because passion pollutes feedback
Founder Fit: Does your business idea merge with your product and lifestyle goals?
Founder Centric: Cashflow-positive education and training agency for startups
Product-Market Fit: People share their problems via a proposed solution; when customers send feature requests, get to root of the problem
Statistical significance of sample size is a trap; reach point of diminishing returns to move forward with product, and focus on number of/hours spent on conversations
Entrepreneurs and customers think every problem matters, but they don’t
What to do next to pivot in the right direction and niche down
Links and resources:
The Mom Test by Rob Fitzpatrick
Rob Fitzpatrick
The Workshop Survival by Rob Fitzpatrick
Founder Centric
Steve Blank
Paul Graham
Skype
Slack
Hacker News
Superhuman Product-Market Fit Survey
Songkick
Spin Selling by Neil Rackham
Drip
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

May 23, 2019 • 36min
89: Go Big, or Stay Small?
Ben announced a medium-sized step forward for Tuple. A bug where the video portion would freeze at the start of or during a call was replicated and resolved. It was a double bonus: Fixed the bug and made the Tuple app faster.
Derrick’s contemplative mode continued as he tried to figure out the future of Level. He retreated to think and disconnect. He sought clarity on what to do and is confident that he has made the best decision.
Today’s Topics Include:
Dynamic Duos: Problem solving doesn’t require understanding of programming language
Fear not! Tuple continues to consistently update dependencies and perform QA
Tuple’s dashboard of latest version of call quality rating is highest so far
Story of Level: How it started; goals, processes, and mistakes made; and what resources are available or needed to make it sustainable and successful
Derrick’s Decision: Not the right path for him to be on, so it’s the end of the road for Level
Go big, or stay small? Launch something valuable that you can charge your market for, then you can expand from there
Product Market Founder Fit: Is the business the way you want to shape your life?
Do No Disturb Derrick: Convinced to cultivate a capability to slow down and carry on
Links and resources:
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
Tuple’s Pair Programming Guide
Drip
Ruby
Zoom
WebRTC
Company of One by Paul Jarvis
Rob Walling’s Stairstep Approach to Bootstrapping
Superhuman Product Market Fit Survey

May 9, 2019 • 30min
88: Will They Make the Jump?
Recently, Ben felt gloriously empty and described how nice it was to have nothing going on. In his stomach, that is. He successfully finished a 48-hour fast. It was difficult, but pleasurable. Now, he’s back to craving calories, eating, and work!
Derrick had a challenging week with feelings of uncertainty. He invited more people to try Level, but got similar results. He fears that people may not progress with the product. Will people actually make the jump to Level?
Today’s Topics Include:
April showered Ben with 66 sign ups of paid trials for Tuple
Magic Number is 3: Multiple developers mean Tuple will soon ship multiway calls feature
Derrick’s going back to customer development roots to proactively learn and listen
Tactical errors with validation to confirm assumptions about how to solve Slack problem
Derrick’s envyable or dire position? Worst-case scenario and what’s next
Startups fail, the struggle is real, and the pivot is time honored for a reason
Links and resources:
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Derrick’s Level Manifesto
Tuple
The Mom Test by Rob Fitzpatrick

May 2, 2019 • 47min
87: Meta Podcasting
Ben boldly admitted to doing a “weird” thing. He started listening to “us.” Not necessarily for quality control, but to spark his memory about topics Derrick and he talked about in previous AoP episodes. As a result, Ben’s become addicted to listening to people building companies podcasts. Unfortunately, there’s just not that many of them.
Derrick also admitted to listening regularly to previous AoP episodes. But more so during the early days of the podcast, when he was apprehensive about his own ability on the microphone and wanted to find ways to improve.
Today’s Topics Include:
Cool Podcast with Cold Open: Hit “Play” and start talking
Autophagy: Putting a twist-tie on snack cabinet sucks, but benefits your body and brain
Tuple’s most requested feature: Multi-way calls
Successful Meta-habit: Surveys serve as way to get feedback on product features
Potential strategies for setting a launch date for Tuple
Art of Building a Product and Company: Word-of-mouth, referrals, affiliate programs
Derrick’s Level Launch: Warm email reminder to whet people’s appetite
Mini-funnel Metrics for Level Launch:
500 given access to Level via email
70% open rate for email
182 created user account
41 created a team
Onboarding Process for Level:
Step 1: Create user account
Step 2: Demo account is activated
Fork in the Road: Optimize each phase and equip people to make it through funnel to get feedback on Level
Derrick’s Top 2 Priorities for Level: Documentation and more manual outreach
Derrick gets Ben “Pricing” Orenstein’s advice on who needs Level the most
Derrick’s Plan for Level: Repeat, refine, and resend
Links and resources:
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
The Art of Product: Episode 78 - Ultraworking with Sebastian Marshall
Tuple’s Pair Programming Guide
Derrick’s Level Manifesto
Drip
113: Justin Jackson - Growing Transistor to $10,000/month
GitHub
Clearbit

Apr 25, 2019 • 52min
86: The Importance of Paying Customers in Product Feedback
Ben had another good week. He signed up 25 new trials and about five conversions for Tuple. Are you one of the 500 chosen by Derrick to get access to Level? Be sure to check your Inbox on Monday for an email from him to find out.
Also, Ben and Derrick welcome Adam Wathan as a co-host for this episode. Adam’s working on getting release 1.0 of Tailwind out the door with awesome documentation.
Today’s Topics Include:
Happiness vs. Harassment: Tuple’s paid trial process
Will people pay for Level? Get free feedback first or make them pay upfront?
Demo Option: Click around, view dummy posts to get sense of how Level works
Refactoring UI: Could it be a perennial seller?
How much should you share about your startup in your tweets?
Focus on being best option; don’t brag about your success
Trying to sell a theme via Tailwind; adding vs. creating new products
Holy Grail of Software Business: Rob Walling’s stairstep approach to recurring revenue
Growth rate required to stay alive? Keep product relevant to what market wants
SaaS is definitely not all roses!
Super Fast Email Services/Features: Snippets, Superhuman, Help Scout, and Shortcuts
Links and resources:
Adam Wathan on Twitter
Refactoring UI by Adam Wathan and Steve Schoger
Steve Schoger
Stripe
Jason Cohen - Designing the Ideal Bootstrapped Business
Perennial Seller: The Art of Making and Marketing Work that Lasts
MicroConf
Tailwind CSS
Bootstrap
Justin Jackson Playing with Tailwind CSS
Justin Jackson’s MegaMaker Club
Patreon
Rob Walling’s Stairstep Approach to Bootstrapping
Upcase by Thoughtbot
Paul Jarvis
Heroku Dynos
Ruby on Rails
Elixir
Superhuman
Help Scout
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple

Apr 18, 2019 • 33min
85: The Hype Is Real
The hype about Tuple is real! Ben’s been busy adding a bunch of new customers. He’s selling and delivering the dream.
Derrick is back after mentally struggling in the midst of moving, which meant a week of zero productivity on Level. Now, he’s in a better place, mentally and literally.
Today’s Topics Include:
Ludicrous Mode: Full-resolution, uncompressed video stream option added to Tuple
Tuple’s lack of scaling challenges due to peer-to-peer connections
Tuple’s conversion rate for email list
Ben’s “I’m bad at sales” email message and demo video
Things to do and features to add in the future for Tuple
Tuple achieves semi-milestone of customer renewals
Ben’s fear of public availability to post Tuple’s pricing
Bandwidth forces AoP podcast back to one episode per week
Derrick ships fun and addictive emoji reactions feature in Level
Inviting more people to increase Level’s sample size and address skepticism
Links and resources:
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
Heroku Dynos
Spaceballs
Adam Wathan on Twitter
Ruby on Rails Action Cable Server
Technical Debt - Our Approach to Building Cool Tech Profitably
Steve Schoger - Refactoring UI: Tuple
Drip
Soapbox from Wistia
Superhuman
Jason Fried

Apr 11, 2019 • 41min
84: Developer Mindset with Brian Casel
Who’s the mystery voice that only gets better as you listen to this episode? Actually, you’re probably already familiar with the work of the man behind the microphone.
Derrick is busy moving to a new home, so Ben’s co-host is Brian Casel of BootstrappedWeb, ProcessKit, Audience Ops, and Sunrise KPI.
Today’s Topics Include:
Ben and Brian just got back from MicroConf; it’s an annual gathering of “all our people”
Some talks were among their favorites, but others were mediocre and missed the mark
Brian’s goal was to meet 5-10 new people doing interesting things, and reconnect and catch up with others he’s known for years
Brian is an Art of Product (AoP) podcast listener and wants Ben and Derrick to not hold back, dig in, challenge each other, and ask more questions
Are more people listening to Ben and Derrick’s podcast? Fireside metrics reveal that a lot of Tuple or Level customers come from listening to it
More bootstrappers need to start a podcast and find friends to share ups and downs
What happened when Ben pushed Brian to learn how to code? ProcessKit - best thing Brian’s built on the Web
Phenomenon of how programmers love complexity
ProcessKit pricing and customer research; Ben’s advice to get people to buy/use it
Tuple Update: App is great; Ben’s been emailing list, and people are buying it
Links and resources:
Brian Casel
BootstrappedWeb Podcast
ProcessKit
Brian Casel on Product Hunt
Audience Ops
Ops Calendar
Big Snow Tiny Conf
Sunrise KPI
Art of Product Podcast Episode 58 with Brian Casel: Evolving Roles as a Startup Founder
MicroConf
MicroConf Recap
Chris Savage: How an Offer to Sell Wistia Inspired Us to Take On $17M in Debt
Jason Fried: Q+A with Jason Fried
Patrick Campbell: Pricing
Joanna Wiebe: Money Words: Seven of the words and phrases we use most often in high-converting copy
Fireside
Transistor
Castos
Blubrry
AJAX JavaScript
Tailwind CSS
Honeybadger
React
Ruby on Rails
Vue.js
Stimulus JavaScript
Vanilla JavaScript
FollowUp.cc
Superhuman
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
Tuple’s Pair Programming Guide

Apr 4, 2019 • 32min
83: The Biggest Lever to Pull in Your Business
Ben and Derrick are back from MicroConf. There were plenty of solid talks and takeaways to help them think, theorize, and hypothesize about moving forward with their products.
Also, Ben presented two Starter Edition sessions: Q & A with Rob Walling and Idea to Validation to Launch: The First 365 Days of Tuple.
Today’s Topics Include:
Ben stuck to plan of not going to many talks; made connections and socialized
Growth-adjacent trend of not buying tickets to conference, but hanging out with others
Ben crushed it when MCing Starter Edition; being part of conference at organization level
MicroConf’s Unofficial Mantra: Charge more; pricing is powerful lever to pull for ROI, and businesses know they should do it, but don’t; if they do, it’s too small
Tuple has stabilized, and it’s time to generate revenue; started emailing list
Retro on financial situation; nothing to worry about yet, but not feeling rich
Links and resources:
MicroConf
MicroConf Recap
Ben Orenstein at MicroConf
Honeybadger
Wistia
Jason Cohen
Hiten Shah
Chris Gimmer
Ruby on Rails
Drip
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple

Mar 28, 2019 • 25min
82: Idea to Validation to Launch: MicroConf 2019
Derrick and Ben have descended upon Las Vegas for MicroConf and an audience hungry for valuable tips on how to successfully start and grow a business.
Ben will have two Starter Edition sessions: Q & A with Rob Walling and Idea to Validation to Launch: The First 365 Days of Tuple.
Today’s Topics Include:
MicroConf Goals: Connect with people, spend quality time with friends; don’t feel guilty or FOMO about not going to all talks
Ben’s seeking a designer to replace super-successful Steve Schoger
Optimism to Realism: Derrick’s shift in mindset about Level at 2018 vs. 2019 MicroConf
Sharing wisdom and giving advice - all of the fun, and none of the hard work
Not knowing what makes someone a good fit for Level; let people vote with their dollars
Getting more founders into therapy to help their mental health
Derrick’s mentor role for TinySeed: The Startup Accelerator Designed for Bootstrappers
Tuple’s theme of recurring and expansion charges, but also one churn so far
Links and resources:
MicroConf
Ben Orenstein at MicroConf
Rob Walling
Steve Schoger
Drip
Sam Harris
Wistia Soapbox
TinySeed
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple

Mar 25, 2019 • 42min
81: Sane and Sustainable Growth with Ben Curtis from Honeybadger
Derrick is still traveling. So, Ben’s co-host for this episode is Honeybadger Co-founder Ben Curtis. Honeybadger offers an application health monitoring tool featuring an easy-to-use platform with exception, uptime, and check-in monitoring.
Since its creation about seven years ago, Honeybadger’s three founders - Curtis along with Starr Horne and Joshua Wood - cranked out all the work. However, the company added a marketing person a few months ago and recently hired its first developer.
Today’s Topics Include:
Honeybadger has kept headcount low to optimize profit-per-employee; eventually needed help with marketing and other tasks
Downside of contractors is they’re not committed to being around for very long; wanted someone who was dedicated to making Honeybadger more successful
Bringing new people in is risky, but Curtis kind of wishes they would’ve done it sooner
Documenting processes is essential to transfer knowledge to new team members and discover opportunities for improvement and automation
Setting expectations regarding time; Curtis makes conscious choice to only work 20-30 hours per week in Honeybadger’s relaxed and asynchronous office environment
Honeybadger took about three years to achieve a stable infrastructure, where things weren’t regularly blowing up and breaking
Moment Honeybadger Made It: Able to offer health insurance and living the dream by getting paid well to do exactly what they want to do and exactly how they want to do it
What can you afford to pay yourself when starting a business? Establish schedule and roadmap to set goal to pay yourself regularly, even if amount is meager
Honeybadger’s biggest costs are for hosting, health insurance, and salaries; company has grown through word-of-mouth, not paid marketing and advertising
Gorilla Marketing: Free marketing and fantastic response rate for Honeybadger’s T-shirt giveaway to get customers’ credit card numbers; Burger Bus was also a success
Be authentic to create brand recognition; you’re your target audience - what do you like?
Honeybadger’s mission is to give developers the best tools, so they can have a better day; customer service is one of the company’s core guiding principles
Links and resources:
Honeybadger
Starting & Sustaining Podcast Episode with Ben Curtis, Co-founder of Honeybadger
Notion
Twitch
Tropical MBA Podcast
MicroConf
RailsConf
Postmark
Printfection
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple