Thinking Like Entrepreneurs: Our Experience with Matter, a Design-Thinking VC Program

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By Hannah Cassius, John Thai and Ben Solwitz

One of our co-workers sent us an email asking if we wanted to be a part of “The Matter Bootcamp”. She explained it as a design thinking workshop, meant to support both entrepreneurs in the media space and larger media companies (like The New York Times) in developing ideas to build a more informed, empathetic and inclusive society.

We took the workshop along with a few other Times employees and admired the focus on the user-centered, prototype-driven product design process. At the end of the four days, we all had created product prototypes ranging from silent disco meditations to a dog petting program. These ideas were more extreme than what we would actually create, but they got us outside of our comfort zone.

The four-day workshop is the kickoff for the extended 20-week program we participated in. This is part of a larger partnership with Matter that has let a number of Times employees to participate in Matter’s process. We learned valuable design and entrepreneurial skills that help us do our jobs better.

How Does The Times Currently Encourage Entrepreneurial Thinking?

For a publication that is nearly two centuries old, we have to embrace continuous digital change to move forward. We have internal innovation challenges, like Maker Week, a week-long, cross-functional event where folks from Design, Product, Project, Marketing and Technology come together to work on envisioning, designing and developing cool new projects. The idea behind Maker Week is to allow people real freedom to work together with people they don’t usually interact with, to think about new problems, get creative, and explore wild ideas.

We used Maker Week as a way to get feedback on our idea. We took paper prototypes of our idea down to the food court under Rockefeller Center. We asked for people’s feedback and then incorporated it back into what we were building. Because of this process, we were better able to articulate what people wanted. We heard consistently that people felt like they were trapped in a news bubble, and that they often ended up going to the same sections or types of articles because it was what was algorithmically suggested to them. We came up with a prototype for diversifying a reader’s news diet.

We spoke to Corey Ford, Matter’s co-founder, about how internal innovative thinking programs like Maker Week differs from a program like Matter. “Many of our partners are doing great work with ‘inside out’ innovation with programs like Maker Week at The Times,” he said. “But we think it’s important to reinforce those efforts with an ‘outside-in’ approach like the Matter Partner Program. Since Matter is a neutral, independent place that serves both early stage media entrepreneurs and mission-aligned media partners we are able to create an immersive experience that challenges internal cultures and process and inspires them to take more risks, be more-human centered, be more iterative, and to think about their projects more like a multidisciplinary venture.”

A Product Manager’s Experience

Photo by Lindsey Adams

Hannah Cassius: As a product manager, I like to spend time upfront before any project to ensure that we are capturing a market need and achieving product-market fit. The challenge in a large company like the Times is that we have a lot of projects and limited time. Being able to focus most of our efforts on defining the problem, refining our solution based off of continuous feedback, and doing all of this work before committing to build anything differs from how projects are traditionally done.

One of the more interesting parts of being in the Matter program for me is that we were working alongside entrepreneurs. They encouraged us to be bolder and take risks, since that’s what they do on a daily basis. By taking a human-centered, prototype-driven approach the entrepreneurs in the Matter program are looking at media in a unique light. For example, one of the companies, Purple, created an SMS platform that connects users and journalists in a two-way messaging-based conversation. Another company, Gretta, is working to open up podcasts to search engines for greater discovery in audio storytelling. It was fascinating being able to work alongside them because they were always thinking outside the box of how to improve the media landscape.

A Software Engineer’s Experience

Photo by Lindsey Adams

Ben Solwitz: I have been a developer for about ten years and had very little experience with product design prior to the Matter program. Usually the requirements for projects that I work on are relatively static, and determined before they get to me. The idea of exploring an open-ended problem with many possible solutions was intimidating at first because I didn’t know where to start. The user-centered, prototype-driven approach we learned gave me the tools to generate lots of ideas while remaining focused on specific needs of real users.

I learned a lot about how to quickly iterate and generate prototypes based on user feedback. Many of the developers on my team asked me if we had built any of the prototypes that we showed them, to which I replied that I wasn’t sure if we had come up with anything that anyone would really want yet. I realized how much more efficient it was to get feedback on a Sketch or Invision prototype than a fully-functional app. Interviewing users with our prototypes helped keep us focused on solving the needs of real users, and not focusing on only what we personally would find useful.

A Systems Analyst’s Experience

Photo by Lindsey Adams

John Thai: Having the opportunity to participate in the early stages of a new idea is sometimes hard to come by depending on what stage your product is at.

For me, having worked with legacy systems and somewhat mature products, I’ve mainly focused on feature optimizations where the need came from already known problems and the solutions were fairly scoped and constrained.

The Matter program allowed me to start from scratch where the immediate focus was the end user and the solution was validated by the end user. During ideation where you’re not concerned with constraints nor scope, our team was able to let our minds flare, thinking freely and radically. We then trimmed down to focus on an idea that would be desirable, feasible, and solve a real user need.

By iterating on a high fidelity prototype and tweaking things based on user feedback, we had something we were able to move forward with and build incrementally. After participating in this program, I have tried to always start with the end user wherever possible and to keep them engaged throughout the process whether it be a new idea or optimizing an existing feature. I really enjoyed the program!

Reflections

One of the challenges we face today is figuring out how best to implement the solutions we came up with during The Matter program. It’s great to understand user needs and develop innovative ideas, but we also have to work through getting buy-in and stakeholder agreement internally to build any product that requires significant staffing. If we could do the program all over again, it would be great to have parallel goals internally around buy-in and metrics, in addition to the design reviews with Matter. For example, this could mean including stakeholders from different teams, such as finance, marketing and analytics, in the process as opposed to focusing on just our idea and using design-thinking to refine it. Having them actively involved, and helping to measure the success of our prototype, throughout the process is something that would have been helpful at getting more buy-in.

Overall though, using this type of design-thinking methodology, not just within the design organization, but across a team of people who may not regularly be exposed to it, was vital to crafting new innovative ideas. This type of program from Matter, and the thinking it promotes, makes us all better at our day-to-day jobs and being open to the fact that ideas can come from anywhere. We are grateful to have had the chance to develop new ideas that work towards building a more informed, connected, and empowered society.


Thinking Like Entrepreneurs: Our Experience with Matter, a Design-Thinking VC Program was originally published in Times Open on Medium, where people are continuing the conversation by highlighting and responding to this story.

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