Lenses for Entrepreneurs

Rachel Aliana
10 min readJan 14, 2019
Seeing the world in a different way: https://www.pexels.com/photo/person-holding-star-cutout-paper-facing-mountain-604895/

There are obvious reason why entrepreneurs fail. Some have too many competitors. Others cannot make their business model generate enough revenue to cover operations. These are known problems. These entrepreneurs can at the very least try to pivot and adapt their actions to find a path towards success.

But many founders trip up on obstacles that they were not even aware of, and waste valuable time building a business that is dead from day one. This might be a student debt consolidation company that is unaware of student data sharing policies. This might be a community kitchen unaware of its cities regulations around food sharing. Because there are so many unknowns in any one company’s space, one of the best things an entrepreneur can do is to methodically look at their company from as many angles as possible. The more lenses an entrepreneur has at their disposal, the fewer unknown obstacles. Community Managers can help founders in their ecosystems to narrow their company’s unknowns both in person and by helping them utilize AI.

In-Person Method

Early on in the entrepreneurship process people are usually scared to share their ideas, even though this is the most time-efficient place to do so in order to not waste energy later on. Community Managers should seek out early stage founders with solely ideas to come to “Exploratory” events. These events connect idea-stage founders to Community Members with very different world views than entrepreneurship. As a Community Manager it is your job to seek out these people and invite them to this event. A lawyer can help founders understand potential legal roadblocks. An urban planner understands the importance of community building and zoning regulations for any physically located company.

Once founders and community members are in the same room, the next step is to organize their discussions in intentional ways. Jesse Schell, the author of the Art of Game Design, created lenses for the game design world to help game designers look at their projects from many angles. Inspired by his work, I have adapted the concept of methodical questioning for entrepreneurs. Community Managers should write down each of these questions onto a flashcard, and give each Community Member two or three cards. Each Community Member should also get two or three blank flashcards and a pen to write down any of their own questions.

Next, have each founder go around to each Community Member and present their idea (1–2 minutes) and answer the questions the Community Member asks (1–2 minutes per question). Each “round” will take approximately 5–7 minutes, with 1 minute needed to change seats. It will likely take twenty minutes to get everyone settled and explain the event, and people generally begin flagging after an hour of purely talking. Budget around an hour and a half to two hours for this event. Founders will likely only get through a fourth to a third of the questions in any one event. Just getting them to feel more comfortable talking about their ideas is a huge win, and with the time constraints for each discussion it forces founders to hone in on their value proposition.

These “lens” cards are great to have around at the accelerator, incubator, or any other meeting place at your university for entrepreneurs. Founders can pick them up and run through the questions themselves or with a friend. Simply the act of questioning their idea through many angles can teach them to more actively seek out potential problems rather than reacting to when unforeseen problems arise.

The lenses to use are below:


  • What emotions do I want people to feel towards my company?
  • What is essential to my company to help people obtain this experience? Customer service? Visual design?
  • How can I reinforce this emotion towards my company along every stage of people’s interactions, from sign-up, to weekly emails, to memories of my company?


  • What is the best venue to reach my customers at?
  • What venue best expresses the experience I want my customers to have towards my company?
  • What properties about the venue imbue the experience I want people to have?


  • What way can I surprise my first customer to not simply give them a product or service, but delight them?
  • What elements of that experience with my first customer can I scale up to many customers?
  • Are there elements that are hidden, unique, or different?


  • It takes energy for people to interact with a product or service. How can I design my company to lower the energy people need to exert to interact with my company?
  • How can I use elements of gamification to increase the energy people want to exert on my product or service and keep them coming back?


  • What motivates people to interact with my company?
  • Is there a gap between the motivations that people say and what they do?
  • How does this motivation tap into larger human goals (the search for food, shelter, or larger meaning) ? How can I tap into ever deeper goals?
  • Are the motivations of the people who use my product or service external or internal?
  • Are there conflicting motivations of different groups who interact with my company?


  • What problems is my company solving?
  • Is this a problem that people are currently paying to have solved?
  • How are people currently solving this problem?
  • Are there hidden problems underneath this one problem that need to be solved first?
  • Why hasn’t this problem been solved already?
  • How can I tie my solution to something that is already evaluated, and costs people money? The clearer I can say, “I am saving you X amount” the more successful I will be.


  • Who came to my platform or service once but either did not finish, or did not come back?
  • Are there themes in terms of the kinds of people who are not coming back? Are there similarities in the point in the process at which they don’t come back?


  • What component of my company gets people excited? Is it something about the sign-up process? Holding the object in their hands? Lasting impact to the field? Find the most exciting kernel and reinforce it!


  • If there were no constraints on time and money, what would my company look like? Are there people who not just like the current product, but are excited about the different kind of future that I propose?
  • How do I feel about the world and what it should be? How can I express this vision through my product?
  • What will the company look like in two years? Four? Twenty?
  • Will the world be a better place if my company exists?


  • What basic assumptions do I have about: the market, my customer base, marketing to these customers, creating the product.
  • How can you most cheaply test whether each of these assumptions are true?


  • Do I have enough time and money to create a working prototype?
  • Is what I’m doing new?
  • Is this problem big enough that I will be able to sell my solution?
  • What kind of revenue can I expect? Will this be able to support myself? Will this be able to scale to be a larger company?
  • Is it technically possible to create the solution I want? Are there limits with current technology that would impede the development of my company?


  • What are the biggest risks to my company’s success? Customer interest? Money? Competitors? Make a list of all the potential known risks.
  • What can I do to mitigate these risks?


  • Who is my customer? What are their likes and dislikes?
  • Who are my most passionate customers? Who are the late-comers who would use my product or service when all of their friends are?
  • Is it clear from my product or service who my company is targeting?


  • Is the goal of using my product or service clear? What do people get out of it?
  • Write out the goal I intend people to get from my company.
  • Are there people who are using my company with different goals? What are these goals? How do these different goals interact with each other?
  • Are these goals concrete and rewarding? How do I evaluate whether they have accomplished their goals?


  • How much time do people interact with my product or service? Do they want to be spending more time or less time with this interaction?


  • Who has access to certain sets of information has incredible power. Who knows what on my platform? How would altering who knows what change the experience people have? Would it change power between different people? Would this shift in who holds information create a change in a larger field or market?


  • Are the rules for interacting with my platform or service clear?
  • Are there punishments for those who do not abide by the company’s rules?


  • How many times can a person use my product or service?
  • Is my company easily understood by newcomers?
  • Is there a way the use of my product or service deepens after longer use? How can I develop levels (newcomer, expert, etc.) to want people to keep coming back and growing their commitment?

Virtual vs. Physical

  • What would an all-physical version of my product or service look like? What would a fully automated version of my company look like?
  • What balance will I strike? What are the pros and cons of which parts I’m making physical and which I am making digital?
  • What mental model do people have of how my company works?


  • What feedback can I give to people signing up for my product or service that they have successfully done so?
  • What feedback can I continue to give them to help them further advance their goals through my company?


  • What data is the most fundamental on my platform?
  • What data is exchanged between different parties in my company?
  • On what channels am I transmitting this data? (face-to-face, phone, text, web)


  • Are people immediately interested in my company?
  • After they gain the product or service, does their interest decline or increase?
  • How can I get their interest to increase after using my product or service once?


  • What part of my product or service tells a story to customers?
  • How does the product or service fit into the story customers want to say about themselves?
  • How can customers personalize their story?
  • What meaningful choices can people make when using my product or service?


  • When is there a clear pathway of how a user should interact with my product or service?
  • Is there an open-ended route through my system?
  • The constraints vs. openness is likely to be related to how many different potential parties there are that use your company, and how many different goals they have.


  • Do I have a way to make money? What is this way?
  • Is the way I make money contrary to some of the interests and goals of the people who use my product or system?


  • What skills are needed to create my product or community?
  • What can my company offer to those people for them to join the creation of this product or service?
  • Do I have the right team to build this company?
  • Is there shared communication between the team? How can I develop a common communication foundation and style between people?
  • How do I get people to share new opinions but also all coalesce and agree around larger decisions?
  • Is there a shared identity, trust, and respect amongst team members?


  • How are decisions communicated amongst people in the team?
  • Where are communications stored?
  • How is information evaluated for importance, put into a calendar of tasks, and then tracked?
  • How is information communicated to customers? How is information communicated to investors or other stakeholders?


  • What is the smallest test possible to see whether people like this product or service?
  • Who will you do this test with?
  • Where will this test occur?
  • What questions will I ask?
  • What will a successful test look like? What does an unsuccessful test look like?


  • What can I convey to people about my company within 30 seconds on an elevator?
  • What next action do I want people to take when they leave that elevator?
  • What basic knowledge of my space does my pitch assume these people know?


  • Does my product or service make people better? Can it make people worse?
  • What is the purpose of building this company? The purpose for me? The purpose for my customers?

AI Method

Recently Chat-GPT has opened to the public. It has already caused several university professors to change around their course styles from take-home papers to in-person tests to combat potential cheating. It has spurred a host of start-ups to catch Chat-GPT created essays (Kelly). As Chat-GPT has passed both the New York bar exam and one of UPenn’s Wharton’s MBA final exams it forces universities to question why students need be going to school at all (Terweisch, Mollick).

In the midst of this uproar in the education landscape, Chat-GPT can be utilized to help founders uncover potential roadblocks. Especially for universities that might not have the funds to host events, or for students who need to work and cannot access many university events, Chat-GPT can serve as an important tool to get feedback early in the process. Even as AI upends much of the education system, within university entrepreneurial ecosystems it can serve as an incredible resource if students know how to utilize it. As a Community Manager, you can provide important structures to help them organize their thoughts and questions for the best results.

  1. Give Chat-GPT a rough understanding of your idea. Ask it to summarize your idea back to you.
  2. Start a new chat. Tell ChatGPT to act as an investor and give constructive criticism on your idea.
  3. If this initial question to the AI investor only generates positive critiques, ask Chat-GPT to identify limitations and technical hurdles. Ask it how much it would take to get such an idea up and running.
  4. Once Chat-GPT creates a list of hurdles or problems, create a list of experts that would have expertise in these problem areas. A lawyer would know legal issues, a manufacturing expert would understand supply chain issues.
  5. Ask Chat-GPT to pretend to be each expert and feed back the criticisms to it, asking each expert to find solutions to these problems.
  6. With a list of limitations and potential ways to solve them, it is important to not take these answers as the truth, but as an important starting point to research your start-up’s problem area.