Accidental Entrepreneur: How to Build And Nurture A Winning Attitude

Ruban Kanapathippillai
3 min readJul 10, 2022

Hi Everyone,

Welcome to my 42nd weekly article as this week is called “How to Build And Nurture A Winning Attitude.”

In this article, I discuss some key strategies and principles I used to become successful in the startup world that is universally applicable to anyone on a similar path.

Also be sure to check out my Youtube channel for more content!

“வினைத்திட்பம் என்பது ஒருவன் மனத்திட்பம்

மற்றைய எல்லாம் பிற” — திருக்குறள் (661)

“Execution focus lies in the resolve of the mind;

all else is secondary” — Thirukkural (661)

We all thrive in the world to be winning and successful people. While few people achieve success in unplanned ways, many others attain success by practicing consistent strategies and consistent focus. As I have been part of teams with great success in the startup world, there are a key few lessons I learnt and practiced to become successful. I consider these strategies as winning attitudes with specific intent and deliberations. Below are some of the characteristic and approaches employed by people with winning attitude:

  • Positive People: The first and foremost environmental factor is surrounding oneself with positive people. I define positive people as those people with a “can do” attitude, while understanding and analyzing the practical aspect of every situation. These people are realists but don’t get down when things start to go down. They double down on the task at hand and find a way to solve the problem.
  • Problem Solvers: I like the phrase that “When the going gets tough, tough get going”. Problem solvers are the people who have a positive and winning attitude who find ways to solve any problem with the best available resources. This has been my blessing at my companies to hire and motivate the right problem solvers with appropriate responsibilities. Hiring those “right” people is an art too. Once you have the right people with the right attitude, as a manager, you can relax and focus on bigger problems.
  • Been there Done that: Hiring few people with experience is important as you get a chance to learn from their experience, both the good and bad, to use them as a sounding board for new ideas. Normally, these kinds of people with humble backgrounds can provide clear reflections on what kind of situations to avoid in the future. While I listen to these experienced people and respect their input, I analyze their input to evaluate whether their experience applies to my specific scenario. The bottom line here is that listen to the input but don’t follow it blindly.
  • Encourage Novel Approaches: As technology evolves, complexity of problem goes up, solutions need to match the level of the problems. This is where the new approaches, new tools, new methodologies, etc. become very important. Just like I was invited to modernize the chip design process at my first job at Rockwell semiconductor where I was introduced to new CAD tools and automation. I hired young people with great attitudes and knowledge to implement new methodologies/solutions.
  • Nuances, Nuances, Nuances: I write a lot about nuances in my writings and podcasts. I tell people that the difference between a successful startup and failed startup is mainly the nuances. Nuances in making decisions, nuances in hiring people, nuances in changing paths, nuances in asking “right” questions, etc. Developing the skill to understand the nuances of each step and pivoting at the right point creates a winning culture along with proud success stories.
  • Building on Small Wins: All complex problems take time to find solutions and build winning products. While building the ultimate winning product is the goal, as a leader, one needs to understand the method to achieve the ultimate result by breaking it down into small chunks. As one achieves those small wins, appreciate the small wins and acknowledge the team achievements. Small wins put together help the team build great ultimate products.

Team chemistry, team attitude and team togetherness are critical for success. Building those teams with a winning attitude is the foremost important requirement of all leaders. Eventually it all comes down to having the right people at the leadership and the right people at the working level. My request to up and coming entrepreneurs is to build and nurture winning attitudes as those people will help you reach great heights.



Ruban Kanapathippillai

Entrepreneur, Founder of multiple successful startups, Mentor/coach, Angel investor (Sandhill Angels) and Positive thinker