Ben Orenstein

Ben Orenstein


Ben Orenstein is the founder of Tuple, a tool for remote pair programming that has been steadily growing for the past few years. Now, Ben runs Tuple with a small team and is delving into what happens when your SaaS starts to hit scale. You might have also heard Ben's voice on The Art of Product podcast, which he co-hosts with Derrick Reimer, founder of SavvyCal, talking about the behind the scenes of running their respective SaaS companies. In the past, you would find Ben working on Refactoring Rails, Trailmix and Upcase.

Talking Points

On Tuple - sales


Now Ben, we're going to avoid talking about the stuff you've spent hours discussing on other pods about why you started Tuple, how you grew your first users and what you did to grow. I'll leave links in the show notes to a few pods where you explain that stuff along with Art of Product, where you literally share everything in real-time.

I'd like to chat with you more about what you're focusing on now with Tuple, such as the direction of the company, your mental models, growing a team and working with Enterprise customers.

  • Your most popular tweet of all time perfectly encapsulated the madness of the Enterprise sales cycle. As you've started to delve deeper into these sales cycles, has your approach changed?
  • Any tips for dealing with challenging / long / complex enterprise sales?
  • You've covered this briefly in AOP, about how your users are not your buyers. This happens often with enterprise. Any processes in place to help with this?
  • Many indie hackers will immediately go out to solve for either other indies, or go heavily consumer focused. Did you start out this way with Tuple? Did it start to change over time?

On Tuple - team, direction and mental models

  • As you grow out a team, what's been the most profound change in how you spend your time? Do you enjoy being a real CEO than an indie hacker?
  • What was important back in the early days, that are just insignificant now.
  • Hiring is fucking hard. I bet you have some nifty tricks up your sleeve for finding good talent... then making sure they are good?
  • Company direction. What does this mean? Ambitions? Funding? Getting the team on board for it? Company culture. Corr, I could ask a lot on this.



I LOVE Art of Product. Has been my most listened to pod over the past few years. I remember listening in my cycle into work at my previous 2 jobs, to sipping cocktails in Spain. I'm bullish on this type of pod and the benefits that come from it.

190 episodes. Started June 2017. After quitting Thoughtbot.
  • What impact has the pod had on yours and Derrick's business?
  • Any active marketing efforts for it?
  • Have Castos Productions / Podcast Motor produced it from the beginning?
  • How do you feel about other bootstrappers making very similar pods. Is there anything they might be able to do differently.

Random stuff I just wanna ask you

  • Wow. You've been around a while doing many things. Any you look back on fondly?
  • How did you first get into the bootstrapping / side project scene?
  • Bloody love the look of Trailmix. I think it was ahead of its time. How did that come about?
  • In 2007 you were a middle hitter in Volleyball. I won't pretend I have any idea what that means. Now in 2021, how are you spending your time outside of work, pursuing passions and interests?
  • Around that time you made a course, Vim for Rails Developers, selling 148 copies at $9 each. Would future Ben be annoyed at you pricing it at $9? Would you make another course now?
  • indoor rock climbing, tennis and golf. Singing.


  • Book - The Mom Test
  • Podcast (not Indie Hackers) - Bootstrapped Web
  • Indie Hacker - Adam Wathan