The Art of Product

The Tuple team is close to shipping true 3-player mode without host & observer role limitations. Derrick launched the Outlook integration this week and is working on a bunch of smaller tasks that have been accruing the past month.

Ben & Derrick chat about dealing with ups & downs in business, finding enough, decoupling fulfillment from business metrics, knowledge archival, dealing with feature requests, and slew of other topics.

Ben & Derrick brainstorm a "rooms" feature for Tuple. Derrick is getting close to wrapping up the SavvyCal Outlook integration. Ben shares highlights from their latest team retreat and teases some new plans for later this year.

SavvyCal crossed an important SaaS milestone this week. Ben is continuing to delegate more responsibilities to his team and redefine his role with the company. The guys talk about Gumroad's recent crowdfunding and Derrick's recent experience with Stripe Capital.

The Tuple team made their first "Hello world" audio call from the new Linux client. Ben and Derrick talk through complex team billing structures. Derrick had a stressful couple of days when the Google Calendar API started misbehaving and daylight saving time rolled over.

Ben and Derrick chat about tools for collaboration and their recent experiences with negotiating deals. Ben wants to level up this year on the marketing front. Work is underway on the SavvyCal integration with Outlook Calendar.

Ben and Derrick chat about joy of shipping features quickly that customers love. They also discuss architecting software to minimize painful changes in the future. The Tuple team is making progress on the Linux client and SavvyCal is working on an Outlook integration.

Ben and Derrick hang out and talk shop with Paul Jarvis, co-founder of Fathom Analytics (https://usefathom.com/).

Ben is working on refining the Tuple company operating system. Derrick reflects on the kind of company he hopes to build and the merits of growing & managing a team vs staying tiny. The guys share their take on Clubhouse.

This week, Ben chats with Spencer Fry (http://www.spencerfry.com/), CEO and Founder of Podia (https://www.podia.com/). Spencer's smart. You should probably listen to him.

The Tuple team is releasing a batch of nice improvements and gearing up for taking on the Linux client project. Ben touched some code recently. Derrick is knocking out a swath of small features that customers have been requesting and is getting closer to building more calendar integrations.

Tuple's latest release is the least crashy of them all! The team is gearing up for the Linux client and feeling energized to take on the challenge. SavvyCal is now officially Derrick's highest grossing independent SaaS endeavor. They are launching a "buy out your annual Calendly subscription" (https://savvycal.com/calendly-buyout)campaign this week.

Derrick & Ben chat about health, hobbits, and habits. Derrick reveals more numbers from the Product Hunt launch and talks through upcoming plans for the product. Links: Sweet Maria's (https://www.sweetmarias.com/) Ken Onion Knife Sharpener (https://www.amazon.com/Work-Sharp-Knife-Sharpener-Onion/dp/B07CW4T6RS) Product Hunt listing (https://www.producthunt.com/posts/savvycal)

The SavvyCal launch on Product Hunt (https://www.producthunt.com/posts/savvycal) was a success! Derrick chronicles the story of the launch and some early results. The Tuple team wrapped up their retreat and has decided to build a Linux client in 2021. This podcast won Best Podcast from the SaaS Podcast Awards (https://microconf.com/podcast-awards-2021)! Thank you to all our listeners who supported us!

Ben & Derrick reflect on their journeys the past year and their plans for 2021.

Ben wants to build a meditation habit and is considering ways to facilitate that. Tuple is still searching for a product designer. Derrick & Ben both saw success with their year-end annual upgrade promotions. Derrick is planning a Product Hunt launch in early January.

We're nominated for the SaaS Podcast Awards (https://microconf.com/latest/saas-podcast-award-nominees/) - go vote! The guys muse about the clever marketing behind the awards and their fellow nominee Courtland Allen's unfair charm & good looks. Ben talks through a shared clipboard feature he is shaping for Tuple. Derrick shipped a bunch of marketing projects this past week.

The Tuple team is finishing up 3-player mode. Ben is continuing to derive value out of coaching (this time with video games). Derrick shipped a 7-day free trial for SavvyCal and competitor comparison pages.

Ben opened up a job listing for Senior Product Designer at Tuple. The Tuple team is working on full-featured multi-participant calls. Derrick shipped embedding SavvyCal links on websites and is working on a number of website updates with Corey. Derrick hopes to achieve default alive state by spring through a combination of marketing efforts.

Derrick reached an important revenue milestone for SavvyCal. Ben is looking forward to an upcoming Tuple retreat.

Ben and Derrick discuss some recent instances of founder CEOs stepping down from their posts. Derrick is shipping a unique feature this week. Ben is trying (but failing) to avoid getting into antique watches.

Derrick has found a new groove working in public again. Ben is polishing a job posting for a Senior Product Designer role at Tuple. The guys discuss long-term visions and harvesting profits vs. reinvesting in the business.

Ben is enjoying working on marketing activities. Tuple is beginning their experiment of offering pairing coaching calls to customers. Derrick shipped a differentiating feature and received very positive response. A new part-time head of marketing is starting with SavvyCal in November. The guys opine about specialists vs. generalists.

Derrick shipped the next part of team functionality, which opened the door for expansion revenue. Ben is zeroing in on hiring a pairing coach for Tuple customers. In his down time, Ben is taking up playing the piano - something his childhood self would be appalled about.

The Tuple team is contracting with Thoughtbot for pairing and leveling up their Rails skills. Derrick is working on team permissions and thinking about working with a marketer after wrapping up most of the work around the StaticKit sale.

Derrick is joined by Cole Krumbholz to talk about Formspree's (https://formspree.io/)acquisition of StaticKit (https://statickit.com/). They delve into Cole's history as a bootstrapped founder, dealing with competition, defining success, how the deal came together, and what's next for both products.

SavvyCal (https://savvycal.com/) is officially launched! Derrick talks through how the launch went and how he's managing his freshly-restocked information pipeline. The Tuple team is nearing the finish line on their large upcoming release and recorded a "peek behind the curtains" screencast for customers.

Ben is trying out Roam (https://roamresearch.com/) for organizing his notes. He shares some tips for engineers applying for jobs. After manually onboarding customers for a few weeks, Derrick is soft-launching SavvyCa (https://savvycal.com/)l to accelerate his learning from real-world customers.

Ben reflects on their latest all-hands meeting and a major upcoming release that will improve the Tuple internals. Derrick recounts the Mighty Cal rebrand to SavvyCal.

Derrick is continuing to manually onboard Mighty Cal users and is incorporating their feedback into the product. He is driving towards optimizing self-service onboarding to enable opening up signups more broadly. Ben is considering hiring a someone to optimize trial conversions. They discuss OKRs and what skills this person might need.

Ben is looking to hire a WebRTC expert to prepare Tuple for multi-way calls and continue improving performance. Derrick has onboarded a handful of paying Mighty Cal customers and is rapidly iterating on their feedback. Oh, and Ben has groceries now.

Ben is taking his first day off in a while to recharge. He's experimenting with clustering calls on specific days to allow for more focus time on other days. Derrick finished the Zoom integration for Mighty Cal and experienced the joy (and sorrow) of onboarding his first outside user.

Derrick has officially begun using Mighty Cal for his own scheduling needs. He plans to start onboarding early users this week. The Zoom integration is underway. Ben is considering ways to compensate and incentivise Tuple hires. As Tuple keeps growing quickly, Ben continues to navigate decision fatigue and transitioning from individual contributor to business operator.

Mighty Cal received Google API verification this week, which was a critical blocker to onboarding users. Derrick worked on scheduling link personalization this week. The Tuple team revamped their call feedback form and are now receiving a broader spectrum of messages from customers.

Ben ran his first all-hands meeting this week. Tuple got featured in a Stripe blog post about the customer portal feature that Tuple was beta testing. Ben has some observations about how Stripe approaches product development. Derrick reached his goals this week with Mighty Cal and is now working toward onboarding the first customers.

Derrick is driving toward the first milestone of using Mighty Cal (https://mightycal.com/) for his own scheduling and is facing the reality of setting ambitious goals for the week. The Tuple team moved into their new office, which spurred on a healthy conversation about the value of working in-person and accessing the remote talent pool.

Derrick details the launch of the landing page for his new scheduling app, Mighty Cal. The Tuple team took a retreat and did a feedback exercise modeled after the Great CEO Within. Tuple is officially moving into their first office.

Derrick is dangerously close to shipping his MVP, but is also lamenting how long it's taking. He's committed to naming a public ship date by next recording time. Ben is on the hunt for an executive coach. The Tuple Boston team is eyeing their first real office space outside of Joel's condo.

We're back! The Tuple client redesign shipped and Derrick is going to help out with an overhaul of the Tuple onboarding process. Ben asked for users to record their first-run experience in exchange for a discount and has learned a ton about what could be improved. The Tuple team is considering how best to plan out their roadmap this quarter.

Derrick had a productive maker week and is (hopefully) a few weeks out from onboarding his first customers for the new product. He is becoming well-acquainted with the Google Calendar API. The Tuple team hired a full-time Mac OS engineer. Ben is thinking about opportunities to innovate with Tuple and taking inspiration from Bezos' shareholder letters.

Tuple hired a firm for QA testing and is gradually ramping them up. Derrick is exploring how best to approach architecting the initial version of his new product (still in stealth mode) and is taking inspiration from Ryan Singer and Jason Fried's recent Rework episode on product strategy (https://rework.fm/product-strategy/).

Derrick explores the difference between the craft of software development and the building minimum-viable products (and why it's good to exercise both). Ben explores hiring a QA testing firm. They reflect on the nature of shipping software and the differences between web apps and native, cross-platform apps.

Derrick is enjoying work the last week by taking joy in setting and achieving small goals each day. The Tuple redesign project is nearing completion and has been a welcome distraction from the pandemic. Ben is hiring a full-time Mac OS engineer and an accountant to help with managing the money side of the business.

The Tuple team is growing as Ben kicks up sales efforts with help of an industry veteran and the engineering team onboards a new team member. Derrick is continuing to work in stealth mode on a new product and is bringing in some cash flow from a consulting project with...tune in to find out.

Ben and Derrick hang out with Tuple co-founders Spencer and Joel and talk shop. They discuss what it's really like to work with Ben, how they approach learning deeply technical things, ways they are preparing for a new engineering hire, and that time they hard-coded user IDs into Tuple.

Ben and Derrick are doing their best to focus right now with so much going on in the world. Ben is spending less time on Twitter these days. Derrick is working on hedging his opportunity bets by doing jobs-to-be-done interviews in the scheduling space.

Suntans and sunburns aside, Derrick’s winter escape to Mexico provided meaningful ideas and perspective on StaticKit. By reading, Competing Against Luck (https://www.amazon.com/Competing-Against-Luck-Innovation-Customer/dp/0062435612), Derrick’s goal is to be innovative and gain traction in product/market fit by asking customers the right questions and identifying jobs to be done. Ben recommends reading, Schlep Blindness (http://paulgraham.com/schlep.html) by Paul Graham. It describes how startup ideas remain a painful process instead of a phenomenon. Also, Ben announced that Tuple wants to hire a part-time remote developer with Mac iOS and C++ experience. Recently, Ben realized that writing is better than talking when it comes to business communication and conversations.

Ben put big and new priorities to the side to cover support for Tuple. By doing so, he discovered different opportunities to reduce the number of support requests received. It’s challenging to work on the right things in a smart order. Derrick knows how support is one of the best ways to identify pain points with your product. He describes how founders often follow their passion instead of their priorities. With StaticKit, Derrick is expanding his focus to align tools that he’s building to meet niche market demand. However, less is more when it comes to outreach and emails.

Even if a product, such as Tuple, is good and people don’t need to be convinced to buy it, there’s still plenty of work to be done. It involves communication, coordination, and collaboration. Ben’s perfect sales pitch and ultimate goal: Sell once, revenue forever. Ben picks his guest co-host’s brain about big deals with major companies. Luckily, Matt Wensing is willing to share his enterprise sales experience, including setting price points, hiring salespeople, and developing documentation. Matt is the founder and CEO of Summit, Out of Beta podcast host, and Riskpulse founder.

Ben never wants to stop working on his startup company, Tuple. Despite some stress, it’s successful and satisfying. However, team members may be added to take over some of Ben’s responsibilities. Based on the book, The Great CEO Within, Ben continues to provide feedback and to document standard operating procedures, policies, and other information to handle the challenge of knowledge management. Derrick emphasizes the importance of documentation, support, and smooth transitions. You don’t know what other people don’t know. Derrick wants to be doing what he’s doing with his startup, StaticKit, but is feeling weary and may be willing to eventually step aside. While attending a TinySeed Retreat, he was reminded of how face-to-face meetings are worthwhile, and it’s good to surround yourself with successful people who share similar experiences.