How to Grow (and Not to Grow) as an Entrepreneur

Illai Gescheit
The Startup
Published in
4 min readFeb 13, 2020


There’s a lot of discussion around leadership growth for entrepreneurs. Being one, and working with many of them as an investor, mentor and advisor I find personal growth to be one of the hardest parts of being an entrepreneur. The reason is that growth is painful. It includes extreme mental states, ups and downs, frustrations, failures but also amazing things like sense of accomplishment, good reviews, building a team and sometimes company exits and financial rewards.

The key factor to determine the quality of entrepreneurial growth is the frequency in which those successes and failures happen and our ability as entrepreneurs to manage them in a why that we learn from them and grow. The optimal phase where growth happens in my experience is not when you have your success nor when you have that awful failure. It is happening in the transition between those states. Growth is accelerated when you are able to manage high frequency of transitioning between your successes and failures.

There are two types of entrepreneurs that grow:

  1. Entrepreneurs that grow old — ‘Grow Old’ entrepreneurs.
  2. Entrepreneurs that grow their mindset — ‘Grow Mindset’ entrepreneurs.

Who is the ‘Grow Old’ entrepreneur?
I’ve worked with so many founders who were not willing to fail and do it fast. They were not able to let go from refining their work over and over and learn from their mistakes. Their frequency between success and failure is so low, that their growth is linear. They just grow their mindset in the same pace as they grow old. They will usually keep developing their product without showing it to real users and will get biased feedback from people in their inner circle or that are not their target audience.

How do you identify ‘Grow Old’ entrepreneurs?
The ‘Grow Old’ founders will always have another feature to add or another bug to fix — they will find an excuse why NOT to launch now. There’s a simple test to identify these types of entrepreneurs. Simply ask them if they launched their product. If their answer is ‘not yet — we still have a few features to develop and then we’ll launch’, and they are operating their startup over a year now, they just grow old and are not willing to fail in order to succeed.

Who is the ‘Grow Mindset’ entrepreneur?
These are founders who are hungry to learn from reality. They are not afraid to fail and they are proud of whatever they build even if it’s scrappy and not perfect. They think they bring value to customers with their first version of their product. They understand that being vulnerable and expect failure to happen will help them learn and grow their mindset. The frequency in which they transition between success and failure is high as they know to get up on their feet quickly and pivot a failure into learning and then turning it to a success. These founder often work with methodologies such as lean startup, agile and ZIZO.

How do you identify ‘Grow Mindset’ entrepreneurs?
These are the entrepreneurs that are already in beta tests when they are only 2–3 months into the building of their product. They move fast and want to learn from feedback. You will not hear them say I asked feedback from my dad or mom, but you’d hear that they set a whole day at Starbucks and asked complete strangers for feedback about their business and their product. They exposed themselves by being open to rejection from users. You will find them hustling until they get answers to fix what made them fail. They are resilient and inspiring.

‘Grow Mindset’ entrepreneurs grow exponentially while others grow linearly
If you choose to stay in your comfort zone and not fail often you will experience linear growth — you’ll just grow old. But, if you do choose to fail, recover and leverage it to learn to grow your mindset then you’ll accelerate your learning and grow exponentially. If you grow exponentially most cases that your startup will grow exponentially with you.

Grow Mindset Vs. Grow Old

Do you want just to grow old, or grow your mindset? Leave your comments below and share your experiences of entrepreneurial growth.

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