Madness Free

Derrick finds some new areas to improve after walking new hires through Drip's architecture, and discusses his custom billing engine. On Hound, Ben delegates the new-pricing project, and validates a new product idea.

This is episode 213 of Giant Robots Smashing Into Other Giant Robots.

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Good Enough, Namaste

Derrick brings a few more new hires onto the team, and ships a change to make clients' Javascript snippets more performant. On Hound, Ben does some direct outreach sales, considers bringing on someone to help with marketing, and muses on the balancing act between product manager, developer, and marketing.

This is episode 212 of Giant Robots Smashing Into Other Giant Robots.

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Battle Hardened Over Time

On Hound, Ben sends out announcements for pricing changes, questions when a decision is the "right" decision when it comes to customer feedback, and toys with per-seat pricing model feasibility. Derrick has a successful first week on-boarding the new dev-ops hire, offers Ben some advice on balancing features with price, and discusses some customer acquisition campaigns.

This is episode 211 of Giant Robots Smashing Into Other Giant Robots.

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Ben plans a camping trip, acquires a new Twitter account, releases his notes on giving great conference talks, and begins to tell users of Hound's new pricing. Derrick reacts to the announcement of GitHub Projects and what that means for Codetree, ships the new form design on Drip, and muses on the ramifications to Google's announced penalizing of intrusive mobile pop-ups.

This is episode 210 of Giant Robots Smashing Into Other Giant Robots.

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Playlist-Driven Development

On Drip, Derrick deals with a high-bandwidth customer and hires a new devops team member. Meanwhile, Ben brainstorms new pricing structures for Hound.

This is episode 209 of Giant Robots Smashing Into Other Giant Robots.

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Efficiency Starts With a Haircut

Derrick switches domains from to, begins to update the design of the Drip widget, and tries to find balance in his varying roles as CTO. Ben hands off the reins of Upcase, switches to a low-tech project management solution, and mixes work and personal todos.

This is episode 208 of Giant Robots Smashing Into Other Giant Robots.

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Database & Queue are Dirty Words

Ben welcomes guest co-host Derrick Reimer, co-founder of Drip, getting to know his background and products for our first outside-thoughtbot view on SaaS strategy (as well as Ben's arm-twisty methods for getting him on the podcast in the first place)!

This is episode 207 of Giant Robots Smashing Into Other Giant Robots.

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How Your Relationship Can Make You a Better Founder

Rob interviews Derrick Reimer, co-founder of Drip, about how his marriage has been a super power during his founder journey. He talks about the ways he gets support from marriage, how it has helped him be more efficient with his time, as well as some of the struggles a founder may face.

This is episode 70 of Zen Founder.

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Building/Scaling a Rails SaaS App

I joined the Ruby Rogues panel to discuss my experience building and scaling Drip and Codetree, two software-as-a-service applications built in Ruby + Rails. We talked about choosing technologies, challenges with growing infrastructure, and how to we have dealt with constraints as a self-funded business.

This is episode 254 of Ruby Rogues.

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Choosing the Perfect Tech Stack

Nothing quite compares to greenfield software development. The canvas is blank and you finally have the opportunity to do it "The Right Way" from the ground up. If you've been building web apps for a while, you've undoubtedly found yourself working with technologies that you'd never use again, given the luxury of a blank canvas. And if you follow the open source world, there's probably a brand-spanking-new boutique framework you've been itching to take for a spin.

With all the excitement of a blank canvas comes an equal amount of anxiety. You know you are one ill-advised choice away from being stuck with the "imperfect" tech stack. You have a hunch about what you want to use, but being the dutiful engineer that you are, you spend a few hours verifying your assumptions by Googling "Ruby vs Go" and "nodejs vs haskell" only to find yourself with net loss of clarity. (Don't do that.)

Take a deep breath, it doesn't have to be this hard.

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