OK Roger

Our Story: Reflections from an Entrepreneur

Rajeev Bector

March 16, 2021


7 min read

I recently listened to a podcast where the well known Tim Ferriss interviewed Ed Zshau. Its a fascinating interview that taught me a lot. One of the things Ed reminds you is the importance of stories. Stories inspire us. Everyone and every startup has a story. Listening to this podcast inspired me to write & share our story - I hope some of you will find it interesting.


Entrepreneurial bug infested me a long time ago, though I must confess it was more serendipitous than congenital. I almost joined a bigco after finishing my Masters in CS - in-fact, I was days away from signing the bigco offer when I got a call from a smallco called Inktomi. This was circa 1998; I had been using a search engine called Hotbot, and at the bottom of the search engine, it said - Powered by Inktomi. That's how I had discovered Inktomi and when I saw some jobs that appeared interesting on their website, I did what most other graduate students would have done - submit my CV.

Since then, throughout my career, I've had the good fortune of being an early member of several amazing & successful entrepreneurial teams, at companies both large and small. All these experiences created an itch that had to be scratched, an itch to truly start with a blank slate.


When we lived in Europe for 2 years, I had the opportunity to travel all over - both personally and professionally. The frustration of having to surf dozens and dozens of websites to shop & plan for travel (in this case, many where in French or Polish or some other language) - doesn't need further explanation. Aiming to always nail it (that other bug - trying to be a perfectionist) meant - I often spent hours and hours of my valuable time, time that I didn't actually have.

In my last job as the CTO of an ad-tech company based in London, I had the good fortune of having a personal assistant who was our office manager. I could just text her or message her otherwise and she would make things happen - a very liberating experience indeed. She worked for the company so there was an implicit trust and I never needed to second guess her intentions or choices. She was of-course never trying to send us more expensive flights or hotels - her incentives were truly aligned with our organization and she understood the preferences of the executive team.

After returning to the US, I asked myself: What if we recreated that experience of having a trustworthy assistant and make it available to everyone who travels? This was the genesis of Roger.

Why are we all going to need assistants?

Let me describe the two key challenges we face to understand how our trusted assistants might help us overcome them

1. The Paradox of Choice

"Choice has made us not freer but more paralyzed, not happier but more dissatisfied" - Psychologist Barry Schwartz, in his Ted talk, The Paradox of Choice

Undeniable facts

  • We are only getting busier
  • We all could use some help

Have you asked yourself why?

While information has become practically free and accessible with swipe of your finger - you now have the additional obligation of making a lot more decisions; decisions you previously were delegating to someone else, are now yours to make.

2. Trust as a Currency

"Currency of the new Economy is Trust" - Rachel Botsman, Speaker and Author of Who can you Trust

Consider the following example : When buying real estate, why do you hire your own agent? Because you need someone who will take the time to understand you, help you understand what you need, has your best interests in mind and overall, is going to help you negotiate the best possible outcome that you desire (this is not an endorsement of the commission model in the Real Estate industry which suffers from some conflicts of interest)

One of the main problems we see with many services & businesses of today is that it's unclear whose side are they on and whose interests are they serving. While they may appear to be serving your interests, further analysis often reveals the contrary. And yet, at the same time, making every single decision by yourself all the time is completely untenable.

Let us use two other examples to further illustrate these inherent conflicts

  • Personal Finance : When you work with a personal financial advisor who are (usually) compensated by mutual funds they are helping you buy, do you really think are truly going to help you in an unbiased way?
  • Healthcare : The over-prescription of drugs in United States is a problem that seems to be exacerbated because of similar reasons (note - I had a really tough time getting any anti-biotics while I was in the UK; the doctors simply asked me to rest, do salt water gargles and drink fluids, almost every single time I approached them)

We hope that businesses of the new-age will solve this underlying lack of trust problem, so consumers and buyers are not having to spend the equivalent of a lifetime making decisions about such important topics as food & nutrition, medicine, finance, travel and so on. Their trusted assistants will help them make better decisions across every walk of life. 

In a nutshell

As technology inevitably disrupts how we live, work and play - for the better, evolution of new business models with inherent trust is a precursor for us to delegate some of our decisions to our assistants and liberate ourselves to focus on what truly matters to each of us.

A note of gratitude

One of the most important lessons taught by entrepreneurship is about the importance of humility.

Creating Roger has been an incredible journey so far, where I've benefited from kindness of many many people

  • from the partnership of all my colleagues and ex-colleagues who've taken the chance to join me in this journey
  • from the help of friends
  • from the wisdom of many mentors and advisors
  • support from my friends/family & our investors with their hard earned money
  • from the trust from our early adopter customers and users

And a non-stop faith from my family, allowing me to pursue this passion and follow my dreams. Along this way, I've learnt so much about myself, my own limitations and have made a countless number of mistakes!  I know I will never stop making more.

Where we are now

What initially started as a hobby project, has slowly evolved into a platform that's slowly becoming like an operating system where human assistants and machines collaborate to help traveling employees.
If you ever want to learn more about how our partners have benefited from having Roger as an assistant for their traveling teams, please don't hesitate to reach out. If you have ideas that you'd like to share, want to see how to streamline your own or your organization's travels or are just curious about how our platform works, how we apply technology, how we think about the role of AI and the role of human assistants - we'd love to have a discourse. We aim to write about some of these topics as we progress in our journey.

In conclusion: my greatest lesson

You can find the greatest satisfaction by allowing yourself to go where your heart takes you, as opposed to following a cook-book written by somebody else. Realizing that most of us have the liberty to follow our dreams, has probably been my greatest realization so far. I wish you the best in following your dreams.

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