Between Ventures

Illai Gescheit
3 min readJan 25, 2021


Throughout my career I founded 4 startups, was on the early team of a startup that was acquired for over $US 160m, Built ventures inside corporates and I advise and mentor many startups in different stages. One of the experiences that I remember very well is that awkward feeling after each entrepreneurial journey ended. Every experience was different for example after the startup I worked for many years was acquired and then shut down when we were already worked in the corporate, I started my own journey as a founder which led me to start my first business. The shut down of that business led me to a journey of self-search for of mental challenges that led me to advise startups, and then build another venture.

Everyone is talking about the journey of building a startup and I do to. I work with founders who are building their teams, help them reach product-market-fit, get their investment — I coach them and mentor them. Everyone also talks about the mental issues entrepreneurs experience while building a startup and believe me this is one of the core things I deal with and help others with.

However, what are we not speaking about. What happens with a founder that built a startup and ran out of cash? How is he feeling? how does the team feeling? does he have a plan what to do next? does he has goals, aspirations, plans to build another venture? or get a job? what about his or her family?

lots of questions…

Being in that place several times being ‘between ventures’ is a very unique experience that could be sometime amazing and fun and sometimes a roller coaster or in some cases a series depression. As a founder coach and mentor I believe in building trust as the fundamental layer to any relationship. A great coach is actually a ‘caring friend’ with some experience and patience. I believe that my personal goal when I’m working with founders closely is accompany them throughout their life-entrepreneurial journey. I am not mentoring them because of their business or their amazing product (well that too…) but the main reason I mentor them is because of them — I want to see them grow as founders and as human beings. This is why I am with them during the venture experience but also during their ‘between ventures’ times.

I’m extremely curious about this unique experience entrepreneurs go through between ventures. Therefore I’m starting a journey to understand, research, talk and help people make it a better experience.

As a starting action I decided to run a quick research on what happens to entrepreneurs who are or were ‘between ventures’. If you either exited your company, closed your startup, decided to quit and join another company, or got acquired and became a VP Product in the company that acquired you you entered the phase of ‘Between Ventures’. The idea of this research is to start to understand how long/short, how tough/fun and how mentally challenging this phase is.

If you are curious about this as well and experienced being ‘between ventures’ I would love for you to answer these 3 questions and if you are comfortable for me to reach out at a certain point, leave your Linkedin address.

If you haven’t been in that unique situation but know a friend, co-worker or someone you met once and happy to share this with him or her — please do.

Link to survey :

Stay safe and happy — we’ll get through this together.