Rajeev Kapur is a 3x CEO, has had 3 exits and is now an author with his book, Chase Greatness. 

And in today’s podcast, Rajeev reflects on the hard times that he’s experienced as a founder — the recession and COVID. 

Rajeev is no stranger to reflection, and has established a framework that helps him to maintain a strong mindset. It can be applied to just about hardship you experience in life, particularly entrepreneurship.

The recession of 2008 — as a new founder

Rajeev’s first point of discussion is 2008. 

He was the co-founder of a start-up. Things were going well, and they had successfully got their first round of funding. 

Rajeev distinctly remembers going for dinner with his co-founders on a Monday in October. And by Wednesday, the recession had hit. 

The recession was the worst that the world had experienced since the Great Depression. The stock market had its great falls and their investors were not immune. 

Four of Rajeev’s investors had gone bankrupt in the crash. And one came literally begging him for the money back. 

Although legally he didn’t owe him a thing — Rajeev’s morality kicked in. 

They weren’t in the position to be making such a move. A lot was at stake. But the investor had literally lost his business in the space of a month.

After talking with his co-founders, Rajeev decided that the best thing for him to do was to follow his compassionate side, show empathy, and give the investor 35% of the money back. 

Choosing this route taught Rajeev that human needs always come first in times of crisis — even if it doesn’t work out for you.

With the money returned, they had to bootstrap the business. But they didn’t get the money that they needed. And ended up having to exit. 

Personally, Rajeev suffered a lot in this first hit. His mental health wasn’t good. His stress levels were at an all-time high, so much so, his heart rate shot through the roof and he ended up in hospital. 

The recession was tough on everyone. But Rajeev looks back on it with gratitude. If he hadn’t experienced it, what came in 2020 would have been much harder. 

Maintaining a Strong Mindset in the Pandemic

When COVID initially hit in the states, Rajeev was with his current company 1105 Media, a B2B marketing services company that was very heavily focused on hosting events.

Within just 48 hours of the pandemic being announced, Rajeev was contemplating if the business would survive. 

There was no article or book written on how to deal with a pandemic. There were no 5 steps to follow. And he didn’t sleep that whole time. 

Everyone in the business rallied together to keep the company alive. Offering furloughs, laying people off and re-negotiating with vendors. As companies had to do. 

Rajeev refused assistance from the government. And survived with his people-first mentality. In the end, he was able to refund pay cuts, rehire people and eventually have a full event cycle once more. 

A Mentality That Inspired a Book

With all his experience of turmoil, Rajeev recalls someone asking him what his personal “why” was. He’d always struggled to think what it was. 

Having known him for some time, they had a clear idea of what it was “to honour other people’s dreams”. When he honours other people’s dreams, he’s able to honour his own. 

This was the foundational story for Rajeev’s book Chase Greatness

Rajeev explored this was careful consideration. It had planted the seed for him to reflect on his core values. And he’s fitted it all into his acronym, GREAT. 

Representing gratitude, resilience, empathy, accountability and transparency. 

Rajeev lives by this acronym.

We talk about how this framework plays out in life, and what it means for him. 


  • The primary role of empathy in entrepreneurship
  • The difference between luck and timing for success
  • The importance of having that personal “why”
  • And why you should tackle hard situations face on

Rajeev remains grateful for all the struggles that he has experienced. 

He sees the writing of his book as a cathartic reflection on how his core values have guided him on his journey.