Productive Play Workshop - Create & Innovate Playing SideHustle!

Full video transcript

This is going to be the SideHustle productive play power hour segment at the Scale with AI Summit. Over the next 30 minutes or so, we’re going to be going from no idea or concept about a business idea from a game of SideHustle, a game that is improv in a box, helps get the creative juices flowing. Taking that idea and then creating a full pitch deck presentation, maybe even a website, maybe even an app in that time frame. We are joined today by Leandra Nisbet and George Hang.

The concept of SideHustle is simple. It’s basically apples to apples meets Shark Tank. You pull a business card, you pull an industry card, and you come up with a business idea based on that, on the criteria of it either being funny, it being fundable, or it being both. There’s one investor each round, and the rest of the teams are entrepreneurs. The role of the investor does rotate each round. So we could in theory play multiple games here, but because it’s going to be a little bit more fun to go a little deeper with this game, we do a quick round first to make sure that we got the concept of it, so you can see how the game functions, then we’ll dig into actually building out the pitch.

We’ll present a quick lightning round. Inside SideHustle, you add the team player names: Darby, Leandra, and George. So these are going to be the entrepreneurs. And then basically what we’re going to do is select a SideHustle card. In this case, the SideHustle would be iCry. First, we got to come up with an industry: home goods. So based on the criteria here, your business, George, Leandra, and myself, your mission would be to come up with an idea. Tyrese is going to be the investor, just like you’re pitching to the Sharks. You got to know your investor. We’re pitching to Tyrese, and your business is iCry in home goods.

George pitched first: “My company is iCry and we specialize in home goods. When you go into your refrigerator, do you ever have the experience that a lot of your stuff has gone out of date, especially your produce, and you’ve wasted a lot of food? That’s our audience. What iCry does is we have a system of organizing your refrigerator so that especially the produce section and things that are date sensitive going to expire are actually organized efficiently using our unique organizing system, and it’s actually tracked using AI. Now I know you can buy refrigerators that are $4,500 that have all this built in, but this is far more affordable. We’ve tested this out. It’s actually working quite well in our test market, and we’re looking for funding of $250,000 so we can scale up not just our production, but also getting the word out.”

Asked how the unit could be so cheap at $45 per home refrigerator, George explained that with AI, they’ve been able to 3D print the organizing systems, and AI is built into the tracking system as well.

After the warm-up round, the group moved into the deeper build. The next SideHustle prompt was a travel-industry concept: an app that would train the AI to engage in conversational communication and dialogue around contextual language and cultural navigation situations, taking an AI-first approach with planned activities that teach relevant vocabulary and offer real-time cultural insights. The concept would work as a travel iterator plan: the user starts their travel plan by uploading documents to a chat thread, and the AI assumes a specific role most relevant and helpful for traveling to that specific part of the world, acting as a context, language, and cultural navigation assistant.

The group used a market research blueprint to identify three core market segments for the app: independent travelers, digital nomads, and first-time travelers, unified by a single predominant pain point they termed “contextual communication anxiety.” From there they moved into a design overview and began building out the next step of the concept, iterating through a chat interface to expand the idea, create a pitch deck and website, and then create an application from the same information.

Reflecting on the build near the end of the session, one participant noted their own workflow: go to Perplexity to flesh out the pain points and create the basic frame of what you’re trying to solve for, then put that into Claude to get it to really expand further, then put that into Gamma to get a slide deck or website, then use that same information to create the application. Pickaxe was chosen in this case because it gives an easy way to add AI into the demo through a chat interface without having to create a Make.com automation or plug directly into the OpenAI API. Another option discussed was building a full chatbot for the main website with more information about the offer, and creating multiple different chatbots quickly with something like Pickaxe. For a fully functional product for a number of different users, more advanced use of Pickaxe with Make.com or another integration would likely be required, but for demonstration and speed, it was enough to bring the idea to life within the 30-minute window.

The session closed with the group having produced three potential travel app concepts in roughly 30 minutes, wrapping with thanks to the participants for joining and playing SideHustle live at the summit.