Part I of a guide to people who are beginning their 'In-Between Time'. The phase between their last thing and their new entrepreneurial endeavour.

I have spent most of my weeks talking with people about how they can start something new. Over the past 15 years, the organization I started called prehype has ended up as a halfway house for entrepreneurial people in their 'In-between time.' It is that wonderful and scary period where people are extracting themselves from their last thing and figuring out what new mountain to climb. When it comes to building someting new, people tend to jump straight into chasing an idea for a startup, but I found that spending some time creating a personalized mental model that will help you evaluate those ideas is very helpful to most. The following are some of the mental models and tools I found works best. However, first a tiny disclaimer. There isn't one way of getting started. It's a highly personal journey where different approaches fit different people. Entrepreneurship should be a very wide definition, not necessarily resulting in a venture-backed startup. For some people, their path should lead to an NGO, running a solo freelance career, making an agency, taking an entrepreneurial role at a corporation, or just bootstrapped side project for the hell of it.

We have made a robust framework and set of protocols on how to ideate and test concepts. I’ll write about them in another post. However, when brainstorming ideas, lets explore how you make a small personal entrepreneurial test-harness first. This allows you to test your ideas not only against business viability but also if a concept is the right one for you to spend the next many years on. This exercise contains four steps:

1. An exploration of your micro-moments

2. Discovering the customer you would like to serve

3. Making a non family/friends support group

4. How you build momentum

"Micro-moments".

Abstract questions lead to abstract answers. An abstract question like, do you want to start something new or take a job? Or are you considering something in crypto or AI? Those types of questions are so broad that the honest answer is often. "It depends". Therefore, I like to start by trying to think of bright spots from my past. I call them "Micro-Moments," and they are very concrete episodes where you were in "flow", giggled, smiled a lot, or were the best version of yourself. They don't have to be professional, either. A few examples of mine are; walking to work over the Brooklyn bridge. Spending time with fellow founders talking about tactics. Exploring (playing with) new technologies and gadgets. Hanging with my dog. Being in the company of kind, thoughtful people. I keep a running list in Notion, and there are probably 25-30 things on it by now. My list of "Micro-Moments" allow me to evaluate projects and initiatives with the simple question, "Is there a good chance that this new thing will lead to more of these type of Micro-Moments"? The exercise is to make a list of small happy micro-moments.

Customer-Founder Fit

One of my prehype partners, Nicholas Thorne, has coined what he calls Customer-Founder Fit inspired by the more commonly used Product Market Fit concept. The important difference is a belief that one of a founder's most important jobs is to decide what customer they would like to serve. The better the fit, the easier the founder will understand their world, will have credibility amongst that affinity group, and will be able to understand which of their problems are worth solving. For Matt, Carly, and I at BARK, "our people" are dogs and people who love their dogs A LOT. For Saman, Rob, and Zach (at ro.co), it was initially their fascination with men with (embarrassing) health issues, and for Kylo, it's people who are gender fluid. It can be all sorts of affinity groups, like parents, developers, kids with mental health issues, and space explorers. So make a list of groups of people who you really really care for, understand, and can see yourself serving.

Review group

As you start exploring new ideas, you need to expand the surface of the people you talk to regarding your new idea. Your family and friends are biased to be supportive and may not have to experience in evaluating or helping in building something new. This creates the risk that you are going to spend too much time (or money) on concepts that are not right. You also want to avoid making all the mistakes that others have made before you. Some advice can be gained from the web, but a lot of mistakes are not documented as people (like me) tend to write more about the stuff that worked than the experiments that didn't. (Hint, there are many). That said, most experienced people in the entrepreneurial world are happy to share in person. Make a list of people who you have met in your career that you really like and are impressed by. Often they are ‘weak ties’. People you might only have met a few times. The list can include former colleagues, not close friends, people you went to school with and so on. If you have picked a few groups you would like to serve in the exercise above, make sure there are some people who fit that group on the list. This group of people will be useful later as you would need people to provide feedback to your ideas, it can be a target list for potential co-founders and if nothing else it can be people who can inspire you and get your out in the world and talk to new people. It can feel very daunting, but in my experience people are very kind with their time when people with entrepreneurial ambitions ask for advice in return for a coffee.

Momentum is oxygen

Starting something new often takes time. You will probably have a few false starts; you need time to explore, test, and start again. Building momentum is important because it's the oxygen that you need to get the ball rolling. The above-mentioned activities can be done while you still have a day job. I recommend that. Most people don't. They start their exploration when they have quit or are otherwise out of a job. That means you need to think of how you extend your own run rate because, as mentioned, things take longer than you expect. Thinking of projects that might get you closer to finding out what you want to build and that generate a bit of revenue is helpful. Start thinking about that right away. You will be happy later. That's the run rate. Now build momentum by starting a few smaller things to get practice. E.g., use our tool at audos.com to think of a small service you can make and use yourself (and potentially sell to others) or start to learn some of the tools that will allow you to build and test fast. We made the class that the prehype EIRs take available on systemize.prehype.com. DM me for a discount code.

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