Founders and Owners Dilemmas

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Happy Diwali

Some thoughts for Founders and Owners based on my interactions with the Founders of my Investee Companies (read more) and others, and my life experiences.

At the outset, I am very proud to be associated with Founders of my Investee companies and I admire these qualities in most of them which are as follows:

  • Have a Higher Purpose to make Positive Impact in the lives of people and live by Core Values.
  • Courage to create a Disruptive and Unique value proposition.
  • Youthful, Energetic and Curious.
  • Unwavering Faith in their Mission while trying to remain Confident and Positive at all times. 


All of them seem to be enjoying the journey of excellence despite the challenges they face in this journey. 

I have attempted to summarise some of “Founders and Owners Dilemmas” that they face during this journey, in my view, the Winners will be the ones who have clarity of thought with respect to these Dilemmas:

A. Should we be Obsessed with our goals or just be Passionate. Should we “Enjoy the Journey” despite challenges or Worry about chasing goals (negative energy has a compounding effect on our thoughts)

B. Do we just Dream or “Visualise the Dream”

C. Founders Philosophy of co-creating Business (Softer Aspects/ Foundations):

  • Do we have Complete Alignment on the Purpose, Values, and Philosophy of Building Business and should Founders be Clones of each other in this regard
  • Do we believe that  Core Values are the Foundations of the Business Building
  • Should we be thinking Exponential vs Linear, Parallel vs  Sequential, Abundance Mindset vs Scarcity, Right brain ( DilSe ) vs Left Brain, Solution vs Problem, Democratise vs Control, Trust and Respect Vs Mistrust, Beliefs Flexible or Inflexible
  • Should we document the Founders Agreement with Roles of each of Founder, Rules of engagement inter se and with the Company and defining consequences of Breach and Disagreements or leave it as an informal arrangement
  • Is “Time” the only Perishable commodity, if yes do we really act Fast and  ensure Urgency and speed in our decision-making process 
  • In co-creating our dreams, should we learn to Fail Fast and have Failure as a core value in this fast-changing environment where Speed of Change is Accelerating
  • Do we relate to the power of the same page across the company and ecosystem. Should we have a social responsibility in the fiber of our company 
  • Do we “Know it All”  vs engage with a “Coach” ( Guru in true sense, read more) who is your Clone and understands you Holistically 
  • Is our Existence because of our Network and Society or do the Network and Society exist because of us
  • Should we focus on the Health of our People and Extended organization, and should we continuously evaluate the health of the Organisation and Ecosystem partners, while running on a treadmill of building and scaling business

Founders thinking on Business Rules:

  • Should we think of building a business with a Legacy or Monetisation mindset. Do we really think hard on Valuation/Dilution vs Value creation
  • Should we be competing against ourselves or worry about competition. Do we think Global vs Local
  •  How quickly can we Scale and create our Brand for Sustainable long term advantage? While building Scale, do we only chase  Market Share or Profitable Growth, do we think about Unit Economics all the time or sometimes. 
  • Should we build Capabilities based on inside out and outside in, what capabilities to be Built vs Accessed. Do we build Backend for Scale now or build modular 
  • Do we relate to the Risk Management Framework, Regulatory and Environmental changes. Should we create the Framework Now or Later or will see.
  • Should we encourage Informal decision making or follow Formal Processes including financial decisions 
  • Do we fully integrate the Ecosystem with our company and do we relate to the power of  “Network” Do we have a philosophy of Sharing fruits of growth “Dil Se” with all Stakeholders.

  • Should one of the Founder be continuously on Fund Raise treadmill and raise money when available


Each Business will have different answers given their stage of evolution and complexity and emerging trends. In my view most of the decisions and thought process will change even for the same company depending on its stage of evolution. Some of the answers may not be about “Or but And”.

This is not a comprehensive list but only indicative, but I am sure this will set you thinking to create your own framework to solve for the Dilemmas. 

Happy to get your thoughts and feedback.

Stay blessed Stay Happy and continue to spread happiness all round. 

October 2019