Desmond Mitchell

Jan 4

3 min read

Evolving Entrepreneurial Mental Models

“You can prepare until the end of time. At some point, you just have to jump.” I have heard multiple iterations of the same phrase from countless individuals and the more I hear it the more truth I find in it. Learning and growth are naturally uncomfortable. And the growth that I have experienced has been uncomfortable yet at the same time incredibly rewarding.

As a series of evolving thoughts on my entrepreneurial journey, I have been reflecting on preparation models from what I have experienced so far. This particular model focuses on 3 areas: Knowledge, Skills, and Attitude.


It has become incredibly clear that as a solo founder you have to be an expert in multiple modalities. Specifically, I have seen the benefit of being known as both a subject matter expert (SME) and an industry expert. The easiest way to differentiate the two aligns with a line that I heard from an investor at Emerson Collective- Jarrod Barnes. He said the best entrepreneurs are able to view the world with a microscope in one eye and a telescope in the other.


Having an in-depth understanding of challenges and problems is invaluable to understanding solutions. The ability to understand personas, speak to what has and has not worked in the past, connect with peers and others in the field, and understand the impact and implications for any solution can make or break a solution. While this does not have to be within a specific sector, being able to speak the language of all stakeholders around the problems lays a foundation to build upon.

Industry Expert

Simultaneously, understanding what is happening in the larger ecosystem tells a different but important story: a story that provides hints to the larger ecosystem’s appetite for change.

I am seeing that successful companies combine great ideas with great timing (and of course, a healthy dose of luck.) Great ideas emerge from having subject-level expertise and timing is often very closely tied with understanding the larger industry ecosystem.


Founders which I have spoken to are exceptional in at least one of the following skills:

  • Selling
  • Product
  • Recruiting

Rarely have I met someone that is the best at all of these skills but it is so important to excel within at least one function. Personally, I have had some exposure in all three areas and I am pushing to develop my selling and recruiting skills, knowing that while I will be involved in product- there will be much of this work that I delegate.

And it makes sense. If the role of the CEO is often the chief evangelist, selling, setting a vision, inspiring others, and driving the product forward tie into all three of these core parts. The next step is just finding awesome people to support and strengthen those pillars for the team!

Mental Modalities

Last but not least is mental modalities. More specifically I have been reflecting on two frames of thinking that I have had to consciously focus on to continue driving this vision forward. Somehow putting one foot in front of the other through all the ups and downs. Those two mental attributes are confidence and resilience.

I would be remiss to not mention that much of my growth in these areas has come from having a supportive partner to pull me up from those down moments, yet I have had to mature individually as well.

Resilience for me is finding ways to keep moving. On good days it is packaging up the feelings of joy and elations, holding those feelings for another day, and trying to stay humble. On the bad days, it is recognizing that my work is not who I am and feedback is a reflection on an idea not me as an individual. It is taking a lot separating the venture from my identity and building an exterior coat to help me through the ups and downs is making this current chapter much easier.

Confidence on the other hand is taking much more work. My partner constantly reminds me to let my light shine and only through allowing it to shine can I support others. In a role where my biggest goal is to support an idea and others who are aligned in the vision, I am learning that it all starts with my belief in both the idea and self.