Ben Orenstein

171: Humans Have A Lot of Drawbacks

April 28th, 2021  |  54 mins 3 secs

Ben and Derrick discuss hiring support engineers and philosophies around customer support in general. They go deep on the topic of investing in your business, diversification, and allocating assets.

170: Beautifully, Wonderfully Dissatisfied Customers

April 21st, 2021  |  35 mins 7 secs

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.

169: The Startup Rollercoaster

April 14th, 2021  |  37 mins 41 secs

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.

168: I'd Rather Commit Sins of Overambition

April 7th, 2021  |  44 mins 9 secs

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.

167: Crossing $10k

April 1st, 2021  |  34 mins 20 secs

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.

166: Hello from Linux

March 25th, 2021  |  34 mins 30 secs

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.

165: The Art of Negotiation

March 18th, 2021  |  34 mins 17 secs

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.

164: We Love A Good Null Constraint

March 11th, 2021  |  28 mins 33 secs

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.

163: Catching Up With Paul Jarvis

March 4th, 2021  |  50 mins 38 secs

Ben and Derrick hang out and talk shop with Paul Jarvis, co-founder of Fathom Analytics.

162: Do You Even Clubhouse?

February 25th, 2021  |  35 mins 15 secs

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.

161: The Podia Operating System

February 18th, 2021  |  38 mins 5 secs

This week, Ben chats with Spencer Fry, CEO and Founder of Podia. They discuss the processes they've evolved to run a swiftly-growing, successful company.

160: Digging Moats

February 4th, 2021  |  26 mins 50 secs

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.

159: Does Tuple Ever Crash?

January 28th, 2021  |  32 mins 15 secs

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" campaign this week.

158: There's Nothing Like a Sharp Knife

January 21st, 2021  |  28 mins 57 secs

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.

157: SavvyCal Wins Product Hunt

January 14th, 2021  |  27 mins 34 secs

The SavvyCal launch on Product Hunt 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! Thank you to all our listeners who supported us!

156: Reflections on 2020

January 7th, 2021  |  46 mins 27 secs

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