

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

Jan 10, 2019 • 1h 16min
70: Refactoring UI: Concept to Launch
If you listen regularly to the Art of Product podcast, then you’re probably familiar with the ongoing joke: How long does it take before we mention Steve Schoger and Adam Wathan? Well, today is your lucky day because not only do Derrick and Ben mention them, but Adam is once again their special guest.
Adam is a software developer, writer, speaker, and entrepreneur. Also, he is the creator of Nitpick CI, host of the Full Stack Radio podcast, and author of Refactoring UI and Refactoring to Collections. He describes the process of successfully making, promoting, and selling courses on the Internet. Plus, Steve makes a special appearance to share his side of the story!
Today’s Topics Include:
Concept and Collaboration: How Adam and Steve work together to create courses
Be genuinely helpful by offering free, good content for people to know, like, and trust you
Build an audience/authority on a topic to make people want to learn from you
Understand difference between what you care about vs. what your audience cares about
Care about quality and effort put into all aspects; utilize Steve’s design tips on Twitter
Signals and validation that your content resonates with and is helpful to your audience
What Makes a Successful Partnership: Similar values, but complementary skills
Promotion via email, newsletter, social media, case studies, and screencasts to grow number of subscribers/followers
Courses: Parts and Pieces (Books, Videos, and More) and Pricing to Make ROI
Launching Products and Surpassing Sales Expectations
Links and resources:
Adam Wathan
Nitpick CI
Refactoring UI
Refactoring to Collections
Full Stack Radio Podcast
Adam Wathan’s MicroConf Presentation
Adam Wathan on GitHub
Adam Wathan’s Email
Adam Wathan on Twitter
7 Practical Tips for Cheating at Design
Steve Schoger
Steve Schoger on YouTube
Heroicons
Steve Schoger on Twitter
Wes Bos
Bootstrap
Stripe
An eBook pricing model that resulted in $100,000 in sales
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple

Dec 27, 2018 • 1h 11min
69: Sound, Actionable Advice with Jason Cohen
Derrick is away, so Ben welcomes Jason Cohen, CTO of WP Engine and four-time entrepreneur. Jason knows a thing or two about startups and mentoring them to achieve profitability and growth.
Jason is a straight talker and tells it like it is to get to solutions sooner. He encourages bootstrap founders to find an advisor who aligns with their goals. You need to know how to take advice and use advice that is right for you and your business. Even if you get great advice, think for yourself!
Today’s Topics Include:
Advice is not enough; luck, execution, and other pieces are involved
Be honest and know what qualities investors want
Jason characterizes a company as a learning machine that’s constantly failing, not doing the right thing, and has no resources; but has agility to learn and react quickly
Embrace your humanity and smallness; don’t lie about being big
Share the good and bad about your startup journey for others to feel connected to and support it
When making decisions, apply filters to cut out things; constraints are useful
Universal Rule of Success: You’re all in and apply a lot of energy; makes you more productive and fulfilled
Many paths lead to success and failure; pick ones that naturally fit you
A good engineer can build features (not risky), but can they do everything else - probably not (risky); identify how a company’s priorities need to change to address risk
To be sustainable, get help and became an expert in something - not everything
Product success depends on use cases and maturity of company (convince customers how good it is now and will get even better); if product isn’t good, then business won’t last
Jason shares ideas and options regarding Ben’s Tuple product
When bootstrapping, getting money is challenging because you’re not on people’s radar
Links and resources:
WP Engine
A Smart Bear Blog
Can you bootstrap a company on the side? (Part 1 with Jason Cohen)
Jason Cohen - Designing the Ideal Bootstrapped Business
Capital Factory
Paul Graham
SmartBear
Peter Thiel
Adwords
Slack
Hangouts
Marco
Silicon Valley Successes Podcast
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple

Dec 20, 2018 • 31min
68: Creating Differentiating Features
Derrick continues to make progress and work toward his self-imposed deadline for Level. He was able to implement and ship batched notifications for the product, which replaces the instantaneous push notifications you would get from a chat tool. It’ll probably be one of the key features to sell as part of the “Level” way. But he’s wondering how to leverage interesting features in marketing.
Ben has been thinking about the same thing with Tuple. He wants to make some features of his product be a seperate, discrete entity that deserves its own spotlight. Capitalize on features!
Today’s Topics Include:
Craft a narrative around “why we did this and the choices we made” for features
Tuple offers two modes: Navigator and Copilot
Avoid labeling every single feature as a big deal; strike a careful balance
Derrick’s working on reactions feature for Level; encourages thoughtful responses
Difference between like and acknowledge notifications; making them stateful
Derrick closed pre-orders for Level on Dec. 14 and figuring out pricing paradigm
Derrick plans to do individual onboarding to set users up for success with Level
People are willing to pre-pay; optimize for meaningful engagement and feedback
When something is not going well and you don’t know how to fix it, know you’re not alone
Ben’s Bad Day: Pairing session revealed bugs and latency issues with Tuple
Coping strategies for dealing with catastrophes; don’t freak out, blow out of proportion
Tuple’s Week: Added 200 to mailing list, chasing leads, and improving product
Links and resources:
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
Stripe
Screenhero
Slack
Basecamp
iOS
Superhuman
Drip

Dec 13, 2018 • 36min
67: Refining Level Notifications and Tuple Alpha Users
Derrick had an interesting week with Level. He focused on important features that will be a part of the product, including notifications dependent on team members’ jobs. Some may want more asynchronous and unobtrusive notifications than others. Level distinguishes configurable notifications based on different roles on a team. Notification policies seem simple on the surface, but are actually very complicated.
Ben announced that November was Tuple’s best month ever for marketing! But now, he is approaching the alpha for Tuple and will focus his attention on product management. Ben wants to figure out what works and what doesn’t. After all, when you can see the wrong thing, the right thing becomes so much easier.
Today’s Topics Include:
Derrick gained clarity on how things should work in Level by writing code and playing with different ideas
When in doubt about design, Derrick takes a screenshot of Level to put on Twitter and get feedback; keeps people invested in the process
Derrick is developing a thick skin and trying to not be defensive about design comments
Level will offer opt-ins and education that help users protect their time and priorities
Ben plans to pair with people using Tuple to identify UX annoyances
Tuple is about to crack the 3,000 people milestone on its mailing list
Level received new refers and spikes in traffic; awareness is building
How to continue to grow your tribe? Opportunities to have an audience when you’re doing interesting stuff
Level’s content strategy will focus on high-quality content, not high-volume content; Derrick plans to commit to cadence of consistency
Can spend time on something, and years later, people still go to it as a valuable reference
Ben wants to open up sales for the Habits for Hackers course, but limit the number of spots available; he’s considering a reverse auction
Derrick’s been considering creative ways to structure pre-orders and pre-sales for Level; trying to decide whether to turn off pre-orders
Links and resources:
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
Habits for Hackers
Steve Schoger
Adam Wathan
103: Steve Schoger - Design Q&A + Refactoring UI Details
Slack
Dense Discovery
SitePoint
Product Hunt
Hacker News
Rob Walling
Paul Jarvis
Brian Casel
Code that says why it does

Dec 6, 2018 • 45min
66: TinySeed Updates with Rob Walling
Ben and Derrick are joined by Rob Walling to share updates - their favorite part of most podcasts!
It’s been a good week in Tuple marketing land. Thanks to Ben’s tweet announcing the release date for its alpha, his launch list goal was reached. He was surprised by how willing people were to help out when he asked them to do it.
Rob is working on TinySeed, a startup accelerator for bootstrappers.
Derrick provided a pre-order update on Level and plans to do direct outreach to those who ordered it to determine their level of interest for validation.
Today’s Topics Include:
Managing Mental State: Jubilation followed by fear; developers tend to turn something positive into a negative
Ben’s customized onboarding experience with Superhuman to be set up for success
TinySeed takes a sane approach to work and build stuff that everyone can benefit from
Believing in and making a big commitment to your startup; if it fails, that’ll be a bummer
Frequent Feedback: Know where you’re going
Angel investing has given Rob a specific skill set from how to pick founders/companies to being their advisor
More money doesn’t make you move faster, especially when it comes to SaaS startups
TinySeed follows the dividends/cash for equity approach when milestones are met to align everybody; forced accountability through meetings
Derrick is working on Level’s onboarding flow and laying a foundation for future tutorials for users to embrace a different way of working
Derrick’s addressing the legal side of Level, such as privacy policies/terms of service
Chat is junk food - it’s a bad thing, but you still want it; Level is more like the vegetables and what you actually need
Links and resources:
Rob Walling
Startups for the Rest of Us
Drip
Brian Casel
Chad Fowler
Superhuman
Business of Software
The Product Market Fit Engine
Reportive
TinySeed
MicroConf
HubSpot
SparkToro
Paul Graham
Joanna Wiebe
Snapterms
Stripe Atlas
Slack
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple

Nov 29, 2018 • 32min
65: Effectively Managing Launch Day
Ben launched Habits for Hackers, a workshop that cultivates habits that lead to an impressive and fulfilling dev career. He incorporates books written by others and makes that content applicable to participants. He’s going to figure out the rest of the details for the course while flying by the seat of his pants. For now, Ben’s just bathing in the dopamine of watching numbers happen!
Derrick has been doing some launching, too. He announced that the end of January will be the beginning of the Level launch and Level can now be pre-ordered (generated about $2,000 so far). Derrick admits that he’s always derailed pretty heavily on launch days. He doesn’t even think about trying to get much productive stuff done.
Today’s Topics Include:
Tuple had a good week and useful coaching call; find and reach out to experts via useful blog posts and mailing lists
Ben’s team has experienced some wins when working on reducing the latency of Tuple, but discovered reducing latency and reducing perceived latency are about the same
Ben and Derrick are recognizing areas where they will some day shift their focus
Derrick recognizes the revenue potential due to who is signing up for Level (teams vs. entire companies); shipped an improved call to action - save your place in line
How Derrick determined the price point for Level; pricing is relative and psychology
Ben is reluctant to commit to pricing for Tuple; always trying new numbers to gauge tolerance on how much people are willing to pay for it
After a launch, Derrick and Ben feel wiped out because then it’s time to do the hard stuff; create a prioritized list and set a deadline to avoid distractions
Ben picked a date for Tuple’s alpha to start - Jan. 7; rather than just take someone’s money, he wants to make sure they are the right fit and would offer worthwhile feedback
Links and resources:
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Level Manifesto
The Level Journal
Tuple
Tuple’s Pair Programming Guide
Habits for Hackers
Atomic Habits
Deep Work
Jason Fried
Drip
Slack
How Superhuman Built an Engine to Find Product/Market Fit
Tailwind
Steve Schoger
Adam Wathan
Sketch
Mod&dot

Nov 21, 2018 • 22min
64: Habits for Hackers
Derrick shipped Level’s Daily Digest feature, which includes a summary of unread/read posts, sampling of posts/replies, and call to action. Also, thanks to Derrick killing it on Twitter, Art of Product’s social media presence is now legit!
Branding and awareness of Ben’s Tuple pair programming tool has garnered interest from well-known companies. So, it’s time to set a deadline for Tuple’s alpha.
Today’s Topics Include:
Ups and downs of building a feature
Good Brain Hacking: Know yourself and have a strategy; try something from your toolbox to change your perspective
Ben designed the Habits for Hackers course; the experience was 50% amazing and 50% arduous - getting better at design through a trial-and-error method
Ben’s Design Tips: Copy existing things, read design tweets and watch refactoring UI videos from Steve Schoger, and have friends who will tell you when something isn’t good
Your success is a lagging indicator of your habits; Ben wants to be held accountable for practicing good development/work habits
Links and resources:
Art of Product on Twitter
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Level Manifesto
The Level Journal
Tuple
Tuple’s Pair Programming Guide
Habits for Hackers
Postmark
Ruby on Rails
GitHub
Elixir
Tailwind
Steve Schoger
Steve Schoger’s Refactoring UI
Adam Wathan
Sketch
The Bike Shed
Atomic Habits

Nov 15, 2018 • 34min
63: Running Successful Early Access Programs
Ben and Derrick were hoping to share a great conversation they had with author, designer, and consultant Paul Jarvis. But, without warning, all was lost when Paul’s audio for the episode could not be saved. The plan is to have Paul back on the show in a few weeks.
Everything else is going pretty well for Derrick, who provides an update on Level. He met his goal and launched the Level Early Access Program two weeks ago. When it comes to testing Tuple, Ben plans to prioritize people early on who have good bandwidth and help guide them to be successful when using the tool.
Today’s Topics Include:
Takeaway and Wake-up Call: Derrick has 6 teams in the early access program; some are using Level a lot, some are not - people are busy and running their own business
Quality feedback for Level testing; offers unknowns, guidance, and clarifications
Derrick’s working on a feature to make sure users remember to check back into Level because it’s designed to be unobtrusive and not bother you
Make a good first impression; capture users’ vision and maintain their interest
Derrick addressed people’s questions about how Level works and will solve their problems via storytelling with concrete, mechanical product details
Derrick is battling perfection, but wants to generate pre-order revenue and set a rolling launch deadline for Level - ideally in January, to highlight new tools in the new year
Ben is doing a podcast tour to promote Tuple, which had its best week for sign ups so far
Tuple also experienced a technical breakthrough - it crushed latency; trust your team to get things done
Tuple adventure is predicated on a value proposition that Tuple can be better than off-the-shelf products because of its key differentiators
Ben is not your everyday developer; recently took a leap and hit the bigtime being a backup singer for Josh Groban!
Links and resources:
Paul Jarvis
Trello
Elixir
Slack
MicroConf
Drip
CodeNewbie Podcast
Bits and Trees Podcast
Full Stack Radio Podcast
Ruby Testing Podcast
Bootstrapped Web Podcast
Swift
JSON
Postmark
Screenhero
Josh Groban
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Level Manifesto
Tuple
Tuple’s Pair Programming Guide

Nov 8, 2018 • 38min
62: Avoiding Negativity
Derrick had a productive week with Level. His deadline of late October to have alpha users try it was looming. So, he has been a bit stressed out. But thanks to relaxation techniques that work for him, Derrick was able to talk himself off the edge!
Ben understands the needs for coping techniques. When little things in his personal life aren’t under control, it’s much harder for him to be productive at work. Every thing’s interconnected.
Today’s Topics Include:
Battle between work and personal life
What makes you happy? Avoid negativity and realize things are going to be ok
Ben’s Failure State: When he doesn’t know what to do for a goal
Make list of known ingredients needed and check off tasks to push you through
Ben’s team did a retrospective for Tuple; marketing is going well and additions have been made to the Tuple Pair Programming Guide
Limiting handle reservations and duplicate updates/emails to opt in or opening up handle reservations that cost something
Who’s serious about your product? Is filtering the funnel good?
Creating sales or a sales team for Level; how Drip did it
Suffering from and dealing with Imposter Syndrome
Links and resources:
Efficiency Starts with a Haircut
Elm
Steve Schoger
Adam Wathan
Drip
Rob Walling
Patrick McKenzie
Stripe
MicroConf
Sherry Walling of ZenFounder
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
Tuple’s Pair Programming Guide

4 snips
Nov 1, 2018 • 1h 13min
61: Unconventional Growth Tactics with Julian Shapiro
Ben is working on marketing plans for Tuple and it’s associated Pair Programming Guide. So, what does someone he admires think of his growth and content marketing plans?
In this episode, Ben’s special guest is Julian Shapiro, who shares lesser known growth tactics he has used in his content marketing to be successful.
Today’s Topics Include:
Write content that’s best for your target audience; what do you want them to get out of it?
Goal: To have people read your content or buy your product
Content marketing in the form of in-depth guides is effective in building a presence and getting people to trust you to pay a high price for your product
An audience is an asset; you can identify how much they can be monetized for whatever you want to build in the future
Content needs to be more than good; establish credibility, awareness, and knowledge
Focus on getting new email subscribers or prepare for the launch of Tuple? Capture people’s interest when you have it
Tuple’s Approach to Growth: Release product to a small group to get feedback, release to another group for further testing, repeat, and then expand scope of growth efforts
Push content to address objections; why customers need/should care about something
How do you apply growth marketing to a giant piece of content? Ads don’t work; A/B test to optimize content; pitch a product, but don’t jeopardize your integrity
Non-paid promotion of content - get on Hacker News; never ask someone to upvote, but use a title that expresses deep annoyance and grief about the state of tech
SEO is easier with small pieces of content; don’t go for low-hanging fruit, but head turns
Part of the magic of Tuple - making it fast to address latency and not feel like a hack
Growth should be a core competency of any startup
Links and resources:
Julian Shapiro
Julian Shapiro on Twitter
Bell Curve
Bell Curve Training
Gary Vaynerchuk
Tim Ferriss
Hacker News
TechCrunch
Screenhero
Superhuman
Derrick Reimer Website
Derrick Reimer on Twitter
Ben Orenstein Website
Ben Orenstein on Twitter
Level
Tuple
Tuple’s Pair Programming Guide