Rishi Shah, founder and CEO, ContextMedia, shares insights from his entrepreneurial journey at the Techweek Chicago Summit 2015. ContextMedia, founded in 2006 in Chicago, focuses on providing health information to improve health outcomes and facilitate communication between patients and their physicians through a media platform.

However, Rishi’s entrepreneurial journey began at a tender age which allowed him to gain immense knowledge and expertise to guide today’s would-be entrepreneurs. When he was 12, Rishi helped his father with investing and placing online orders. This fostered his interest in investing – “using numbers and computers to make money.” By the time Rishi graduated from high school, he was already an entrepreneur and had started exploring computer usages to a large extent.

Some of our key takeaways from the conversation:

  1. Tactfully Handling Incomplete Information while Decision-Making with a Level Head:
    Rishi feels that as a leader, an entrepreneur needs to handle emotional volatilities with a degree of level-headedness and should be able to gauge uncertainties as well.
  2. Why Healthcare?
    Rishi selected healthcare to try his business acumen, as 80% of healthcare costs are incurred by chronic diseases whose treatments are possible but, in most cases, timely decision-making is lacking. Therefore, to initiate a behavioral change for the consumers, Rishi felt the need to create a platform where content will be delivered in context at the point of care.
  3. Mistakes Take Place, But Learn How to Reduce Them at the First Go:
    Rishi shares what he thinks is essential for any company head to learn and avoid so that the journey remains smooth –
    a) Need to focus on one product with a specific budget line
    b) Validate this product for a product-market fit and choose a specific customer class for it
    c) Need to learn how to confront in an organization and build effective strategies to scale up the organization
    d) Develop a higher threshold of pain tolerance, as being an entrepreneur is not easy
    e) Need to align the organization properly and maintain the changes as and when it grows
    f) All employees are to be infused with energy, passion, and commitment towards results to be achieved for the organization

Below are some of the key points and moments from the conversation:

  • 0:07 – Rishi Shah begins his speech by first applauding Techweek on its success
  • 1:10 – Rishi believes that the entrepreneurial journey for each person is unique and special
  • 1:52 – Rishi’s journey began at the tender age of 12 by helping his father with investing and placing online orders
  • 5:09 – He started his own company when he was in high school and created a business for home computer consulting
  • 6:03 – He moved to Iowa to work on a political assignment and gradually developed an interest towards founding his own enterprise
  • 7:01 – ContextMedia was started in 2006, focusing on the healthcare industry
  • 12:09 – Struggling up the ladder, Rishi started his company with co-founders as a bootstrapped project
  • 13:37 – Key lessons which Rishi has learned throughout his journey helped him in setting up his startup culture
  • 17:35 – The first setback for ContextMedia was in 2008 when three international businesses verbally promised to purchase the business but couldn’t sign official agreements due to the impact of the financial budgetary crisis
  • 24:08 – Rishi analyzes the risk of starting a new business with growth challenges and pinpoints the lessons learned in the long run


Founder and CEO, ContextMedia