The pursuit of making entrepreneurship effortless: Startups, risks, and AI
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“Being long-term greedy is the hardest thing about entrepreneurship, because most people have started a lifestyle. They worry about their kids, their college, their mortgage, their cars, all this stuff. And that is what basically binds you in any way."
This nugget of wisdom from Dheeraj Pandey, Co-Founder and CEO of DevRev, captures the essence of the inaugural episode of The Effortless Podcast. Joined by Amit Prakash, Co-Founder and CTO of ThoughtSpot, the duo broke down the multifaceted nature of entrepreneurship, risk-taking, design, and the transformative power of AI.
Drawing on decades of personal and professional experience, Dheeraj and Amit engaged in a candid conversation that moved seamlessly between deeply personal anecdotes and insightful lessons, offering listeners a rich tapestry of ideas to rethink work, innovation, and growth.
Here’s a glimpse of the podcast. Check out the video below to catch the whole episode:
The origins of Effortless
The podcast’s title, The Effortless Podcast, encapsulates their shared belief in the power of intentional design to simplify complexity. Both Dheeraj and Amit have built their careers around the idea that success doesn’t have to feel like an uphill grind if you design your systems—whether in life or business—thoughtfully.
“I used to like the word frictionless, but friction has more of a negative connotation than the word effortless, which is also a much shorter word,” Dheeraj notes. The inspiration, he adds, came from the principles laid down by author Greg McKeown in his books Effortless: Make It Easier to Do What Matters Most and Essentialism: The Disciplined Pursuit of Less.
Eventually, a lot of it is really about design-designing our lives, our companies, our organizations, our day to day. And design is about releasing friction. And having the joy of working on things that are hard to begin with and yet the fact that it’s so joyous makes it look effortless.
Taking risks: redefining security and embracing uncertainty
Risk-taking, a cornerstone of entrepreneurship, was a recurring theme in the conversation. Recounting his time as a Tech Lead at Google, Amit says that his team contributed hundreds of millions of dollars to the tech giant’s revenue and he was compensated well. But leaving his lucrative role at Google to co-found ThoughtSpot was a calculated risk that he took.
There are a couple of ways that I thought about it. One was that, let's say if I take this leap and things don't work out, I will know if things are going really south maybe in a year's time, and I can come back to maybe not the exact same job, but something similar. So in that sense, yes, there was a downside, but it was bounded downside.
Dheeraj, too, reflects on an early moment of risk that shaped his life. At age 17, right after completing his high school in India, he appeared for the highly-competitive joint entrance examination twice to get into a computer science degree from the Indian Institute of Technology (IIT) at Kanpur, India (which, incidentally, is the same campus that Amit went to). The second time he took the examination, he earned a top-100 rank in 1993 and landed the computer science major at IIT-Kanpur, just the way he wanted.
Years later, after having started his career in the United States, Dheeraj demonstrated this same courage and risk-taking by turning down lucrative roles to join a small company like Zambeel to prioritize learning and building a strong foundation for his career.
He also recollected surviving through tough times—he was a software developer when the dot-com bubble burst in 2000 and became an entrepreneur by co-founding Nutanix in 2009, right after the global financial crisis.
Just keeping your heads down, hunkered down, learning, learning, learning, not worrying about how everything around you is melting down, is actually very important as well early in life.
Balancing and letting go: an entrepreneur’s mindset
Citing the trifecta of autonomy, mastery, and purpose from Daniel Pink’s book Drive: The Surprising Truth About What Motivates Us, Dheeraj said that he was always driven by a sense of autonomy, which made him take the plunge into entrepreneurship.
But what are the building blocks of the entrepreneur’s mindset? Dheeraj says that you need to have a bit of a cognitive dissonance where you need to have both paranoia and optimism. Entrepreneurs can’t afford to be too optimistic or too paranoid when it comes to making business decisions, so paranoia and optimism has to be the yin and the yang—a constant balancing act between conflicting forces.
“You’ve got to have that tightrope walk feeling every day, every week, every month. And it’s the hardest part of entrepreneurship,” he acknowledges. An analogy he gives is a “marathon of sprints,” where you need the stamina to go the distance while also making rapid, tactical decisions every day.
Another building block of entrepreneurship that Amit and Dheeraj agree upon, and something that’s as hard as the first one, is the ability to let go. Amit talks about how there’s a sense of starting from scratch while founding a new company after being an executive in a large organization. From being at the top of an organization to becoming a one-person team who’s looking to raise a seed round requires you to “reset your mindset,” which is only possible when you have a lot of conviction in your idea, he elaborates.
At some point, you have to take a leap of faith and say, I don't know all the answers, and yet I have enough conviction to bet a large amount of capital, some people's career, and your own reputation in there.
AI’s transformative potential and the role of good design
AI, both Amit and Dheeraj acknowledged, is reshaping industries and redefining innovation, as advanced reasoning AI can make much of intellectual grunt work redundant. To highlight AI’s transformative potential, Dheeraj even drew the parallel between AI’s capability to transform businesses to what the invention of fire did to humankind.
AI is going to be oxygen. It's going to be everywhere. The question is how do you make money on it, and how do you really make it useful? Not just make money, but how do you make it useful for the end user?
He goes on to describe the “three-layered cake” approach to AI at DevRev: The first core layer being data, second layer being large language models, and the final layer on top will be the apps and surfaces.
But regarding the third layer, Dheeraj notes that apps and surfaces have to be redesigned as the apps of the last 20 years might not be able to retrofit AI, much like how cloud computing couldn’t be retrofitted on on-prem software.
To illustrate how important design is, Amit gave the example of ChatGPT. While instruction-tuned LLMs have existed before and got little public attention, OpenAI gave it a “design twist” by making it a conversational chatbot, which made it much more usable and accelerated the AI boom. The message here is that AI models need design to serve the needs of the end user.
I don't think that just raw AI will deliver the full potential. We would have to bring the design thinking and empathy for the user and understanding of use cases and pain. And when you combine those two things, that's when sort of the magic will happen in this era.
Wrapping up: The power of context
Towards the end of this first episode of The Effortless Podcast, Dheeraj and Amit drive home a crucial word: context.
Context is the foundation for navigating the risks and rewards of entrepreneurship. Whether you’re founding a startup or joining one as an early employee, understanding context is key to making informed decisions and maximizing your impact.
Dheeraj noted that founding a startup isn’t the only condition for an entrepreneur, but joining as an early employee in these startups too is entrepreneurial. To set some context for the next episode, Amit suggests discussing how to read the visible and subtle signals that determine whether a startup will be successful or not for those contemplating their next career move.
Hungry for more insights? Dive deeper into the world of effortless entrepreneurship, design-led AI, and the future of work by following along on The Effortless Podcast Substack. With every post, you’ll uncover new layers of context—essential knowledge for building and leading the startups of tomorrow.
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