Ben Orenstein

60: Celebrating the Small Wins

October 25th, 2018  |  26 mins 33 secs

The feeling of accomplishment you get from doing hard things has become Derrick’s way of living recently. Building a startup like Level is hard, but he feels good when he makes small wins. It’s rewarding when he makes progress.
Ben is on a roll right now with Tuple. He’s making progress and getting stuff done. His Pairing Programming Guide is turning people into Tuple subscribers.

59: Pros and Cons of Working Alone on a Product

October 18th, 2018  |  41 mins 58 secs

Adam Wathan, a software developer, writer, speaker, and entrepreneur joins Ben and Derrick on this episode. Adam is also the creator of Nitpick CI, author of Refactoring to Collections, and host of the Full Stack Radio podcast.
Usually isolated and working alone, Adam enjoys the opportunity to chat with others about what everyone is working on. It’s like a mastermind session that’s fun and rewarding!

58: Evolving Roles as a Startup Founder

October 11th, 2018  |  56 mins 38 secs

Ben and Derrick are joined by Brian Casel, podcaster, cofounder of Big Snow Tiny Conf, and known as “Mr. Process.” The three are fans of podcasts and conferences because they offer time to build relationships with people and talk deeply about things.

In this episode, they share their updates and thoughts on involving others in their day-to-day processes. It brings everyone together to learn from each other, as well as build a community and consensus.

57: Finding the Right Marketing/Product Balance

October 4th, 2018  |  52 mins 44 secs

Ben recently returned from an entrepreneur retreat that featured sessions and activities focused on various topics, from projects people were working on to troubles with cofounders. Attendees were able to be honest, open, and transparent with each other. Ben had the opportunity to demo Tuple during the retreat. Feedback was that there are too many people working on its development, so he should focus on marketing.

Derrick emphasized the importance of keeping in mind the cost of getting someone caught up to speed on a project. He has thought about hiring a contractor to help with the development of Level, but decided that his single brain was enough.

56: Finding Your One Thing

September 20th, 2018  |  26 mins 12 secs

Ben is back from retreat #2 for Tuple. It may not have been as good as the first retreat, but was still above baseline productivity. The team worked on refactoring the app. Then, he went to CocoaHeads, which is for MacOS X and iOS developers to discuss Apple's Cocoa and CocoaTouch.
Derrick will be speaking about Level at the local Elixir meetup. He is excited to dive deeper into using Elixir and reading books about it. Then, he plans to share what he learns and encourage others to not be intimidated by more powerful concepts in Elixir.

55: The Entrepreneurial Rollercoaster

September 13th, 2018  |  24 mins 36 secs

Derrick is in Washington for ElixirConf. Like Elixir, he is becoming more comfortable with stability, as opposed to constant churn and new stuff all the time. He knows you have to show restraint to try and not solve every problem. While at the conference, Derrick wants to make connections with people and hopes Level will one day be a good use case example for the Elixir community.

Ben is discovering that startups are not easy. There are a lot of ups and downs. While other people were enjoying Labor Day, Ben was actually being a boss and getting work done. He may not have worked on the highest priority, but on a task that was satisfying to work on.

54: Continuous Learning

August 30th, 2018  |  31 mins 42 secs

Ben has been focusing on MacOS development and writing code. There’s so much he doesn’t know. But that’s ok. He strives to regularly learn things - just keep making progress for it to feel less intimidating.
Derrick has the same mindset. It’s ok to not know everything. Start with the basics, and keep going. You’ll figure things out eventually.

53: Launching Transistor.fm with Justin Jackson

August 23rd, 2018  |  41 mins 2 secs

Today’s guest, Justin Jackson, just launched a podcast platform called, Transistor.fm. Justin describes the time he spent working with co-founder Jon Buda to get it ready to go live. Launching involves a lot of energy and emotion with ups and downs.

Whether working on your own or with someone else, Justin encourages you to take time away to work on something to focus on it and make significant progress.

52: Tuple Native App and Level Inbox Workflows

August 16th, 2018  |  25 mins 40 secs

Ben is back from a productive retreat with his Tuple co-founders. It was deep concentration work that didn’t feel like a chore, but a feeling of joy. They experienced a milestone - scrapped the electron-based version of their app to work on a native functional prototype. There’s a ton more to do, but it basically works. The pieces are coming together.

Derrick understands the foundation required to pretty much get anything done with a new product. He is considering a future retreat, but wondering if the benefits are worth it to go off somewhere as a solo founder. The most critical item on his radar and one of the biggest unknowns he continues to battle is how the mechanics of Level’s Inbox will work.

51: Recast - The Origin of Level from Startups for the Rest of Us

August 9th, 2018  |  35 mins 27 secs

Ben is out of town on a retreat with his Tuple co-founders, and Derrick is deep into building Level. So, this episode features Derrick as a recent guest on the Startups for the Rest of Us podcast. Rob Walling interviews Derrick about Level - what inspired the idea and how he went about trying to validate it.

50: Doing the Hard Things First

July 26th, 2018  |  32 mins 10 secs

Derrick continues to reinvent himself with his new product, Level, and sporting a, “I work for myself beard.” He took a vacation to canoe and camp instead of code. It’s always a refreshing experience for him to get away from work from time to time. Now, Derrick is back to writing code and organizing tasks in Levelland.

Ben also went on vacation, but before doing so, he realized no sales for Tuple had come in that week. So, he made an effort to call prospective clients and was able to sell six annual licenses. Now, like Derrick, he is working on things that are hard to achieve. But if they can make them happen, then they will be really good.

49: The Evolving Tech Stack

July 12th, 2018  |  21 mins 49 secs

Derrick continues to code to make progress on things he will need to build at some point for his product, Level. Also, he spent a lot of time in Elm land for refactoring and additions. Will Elm code work for scaling necessary for Level? Derrick is still trying to decide.

Ben’s team at Tuple has transitioned from C++ to Swift, a newer and friendlier language. Also, Tuple hired a consultant as a sanity check and to be pointed in the right direction for building a native app on Mac. Initially, the consultant will help step up and build with dependencies needed.

48: When Is the Right Time to Take Outside Funding?

July 5th, 2018  |  31 mins 12 secs

Derrick was hoping to finish mock-ups for communication flows inside Level to get feedback, but that turned out to be a lofty goal that he is still working on. The process of designing Level has generated more questions than answers and minute details that Derrick needs to address. This is the real work happens.

Congrats to Ben, who finally crossed 10,000 followers on Twitter. He uses Twitter as a way to provide value, be useful, and build relationships. Also, he launched the Code Quality Challenge sign-ups and a private podcast to share information with people who are interested in Tuple.

47: Pacing Yourself When Starting Up

June 28th, 2018  |  33 mins 56 secs

Despite being in the process of building new companies and products, Derrick and Ben understand the importance of sustainable pace - being able to unplug and get some rest to make smart decisions. So, Derrick just got back from vacation, and Ben plans to take some days off soon. It’s about the mental component of mastering your brain.

Derrick is getting back into the swing of things and trying to finish the mock-ups for communication flows inside Level. Ben has been focusing on filling up Tuple’s alpha and booking substantial pre-pays. Also, Ben shipped his landing page and already has about 12,000 subscribers.

46: The Importance of Trust with Your Audience with Justin Jackson

June 14th, 2018  |  1 hr 6 mins

Today’s episode features guest Justin Jackson, who is building a new podcasting startup called, Transistor.fm, and runs MegaMaker training and books for SaaS and indie software companies. He’s discovering that it’s a lot of work to build something.

Derrick and Ben know how he feels. For Derrick, it’s been a fun week in the land of Level. He’s been working on his new landing page and landing new sign-ups for the pre-launch list. Ben has pre-sold $700 worth of Tuple accounts and raised $500 worth of verbal “Yeses.” Contact Ben if you want to be a part of Tuple. They share their ups and downs, fears and triumphs!

45: The Value of Teaching

June 7th, 2018  |  41 mins 17 secs

He’s back! Ben returns from traveling to Hong Kong. He shared his rails knowledge by helping someone who is building a business and using a rails app. He made performance improvements and refactored items. Derrick is also doing some Vim tutoring. Learning something new does not take long or a lot of money, and gets easier.

Of course, both Ben and Derrick continue to work on their new products, as well. Derrick is creating Level, an open source team communication and management tool. Ben is starting Tuple, a pair programming tool alternative for Screenhero.