“At that time, if we realized the pain and suffering, and just how vulnerable you’re going to feel, and the challenges that you’re going to endure, the embarrassment and the shame, and the list of all the things that go wrong, I don’t think anybody would start a company. Nobody in their right mind would do it.”
These aren’t the words of a failed entrepreneur—quite the opposite. Jensen Huang, the CEO of NVIDIA who came on top of the AI boom and has a net worth of US$130.5 billion, said this.
Still, why do people leave their cushy corporate roles and predictability that comes with it to throw themselves into this mire of uncertainty?
That’s exactly what Dheeraj Pandey, Co-Founder and CEO of DevRev, along with Amit Prakash, Co-Founder and CTO of ThoughtSpot, will break down in this second episode of The Effortless Podcast.
The duo dive into how to determine if you’re built for startup life, what it takes to succeed, and how to evaluate a company’s founding team and vision. They break down the risks, mindsets, and frameworks necessary for both joining a startup and creating lasting impact. They cover the realities of startup culture, balancing ambition with practical skills, and the subtleties of “founder-market fit.”
What does it take to join a startup?
Before knowing this, Dheeraj gets one thing out of the way: who shouldn’t join startups?
He answers that people who’re really comfortable in their current role and feel like they have an impact in what they’re doing right now might ideally not consider joining startups. Those who think, as he puts it, “Let me just stretch the current runway I have and be good at what I do right here.”
So, now to answer the actual question. Joining a startup—whether you’re about to co-found the venture or come aboard as an early employee—demands a brutal self-assessment of your risk tolerance. From the get-go, Dheeraj and Amit confront the reality that startup life isn’t just about chasing big dreams but also involves embracing moments of doubt, unpredictability, and financial strain.
Both agree that hunger for autonomy is the biggest motivating factor for people to jump from a world of predictability into the world of startups.
Amit also points out that equanimity—remaining centered during extreme highs and lows—becomes non-negotiable. In a startup, you handle many unknowns, from shifting markets to new technologies. Amit reflects on whether people can maintain composure under swirling demands: “Everybody has some quotient of how they respond to highs and lows in life.”
The design advantage for startups
Design, according to Dheeraj and Amit, isn’t just a cosmetic layer. It’s a philosophy that influences your choice of algorithms, your user experience, and the system architecture that undergirds your product. Startups gain an edge precisely because they’re not bogged down by the legacy structures of big corporations.
In this age, design is always a competitive edge for startups because you get to rethink and redesign things and aspire for something delightful. When you’re an existing product, the existing complexity is the enemy of design.
Amit observed how critical it was to put design thinking front and center. He describes how large organizations, who have too much to lose given the size of their business operations, move slowly when it comes to innovation. Smaller setups like startups, by contrast, maintain the freedom to radically rework their assumptions, user flows, and tech stacks.
But in a startup, balancing speed and quality is an art. The markets move quickly. Competitors emerge from unexpected corners. Users adopt new technology at an astonishing rate. Yet if you cut corners too aggressively, you might wind up with a system that collapses under its own success.
As Dheeraj notes, “If something were to be hacked up in a month and the right thing was three months, I would do the thing in three months.” That nuance—knowing when it’s worth taking extra time for the right design—often spells the difference between a product that scales gracefully and one that falls apart under user demands.
Back in the 90s, it was IBM and Oracle selling big products to big companies. And I think ever since this evolution of VCs and startups, there’s a lot more disruption happening. So it looks like design plays an even more important role. In our lives, every decade, every year, every five years, we’re seeing a lot more emphasis on design.
When combined with the principle of building only what’s essential, design becomes the compass for both short-term actions and long-term survival. It ensures you don’t drown in complexity. It also aligns you with the vision of delighting your user, whether that user is an enterprise client, a small-business owner, or a consumer interacting with your platform. Startups that weave design thinking into every layer—from the UI to the backend algorithms—stand a better chance of not only meeting user needs but also surpassing them in unexpected ways.
Identifying a startup’s vision and market awareness
No matter how brilliant the product concept is, a startup rises or falls on its ability to fit that product into the market’s evolving puzzle. Dheeraj and Amit insist that founders must maintain a strong vision while remaining agile enough to pivot when reality intervenes.
A founding team must risk taking bold stances—like selecting a certain technology stack, or targeting a precise market segment. As Dheeraj says, “Not taking the risk itself is probably the biggest risk.” But, the founding shouldn’t cling so tightly to the initial plan that they ignore signals urging them to adapt.
Timing, too, is part of the founder’s calculation. You need enough awareness of market readiness to ensure you don’t push out a product the world isn’t prepared to adopt—or, conversely, cling to an outdated approach that has passed its expiration date.
If you are in a startup, you’re basically building from scratch and you’re moving towards the future a lot more than others. In fact, me and my co-founder used to talk about this that if we had started ThoughtSpot in 2016 as opposed to 2012, we possibly would have done much, much better as a company, because that’s when cloud in the data space became a lot more real.
Both Amit and Dheeraj urge prospective employees looking to join startups to educate themselves on all aspects of company building and check with the founders during the interview process to see if they align with your values of what goes into building a great company.
Dheeraj, in particular, highlights the importance of the “wedge scenario,” where the founders have a vision of sitting next to the incumbent market leader and be profitable, but still have the potential in the long term to eventually replace the incumbents.
The conviction in the vision, along with flexibility and adaptability for the mission and goals, are the important qualities for the founding team in any startup, Dheeraj notes.
Culture and conflict in startup environments
Few factors shape a startup as profoundly as its culture. When you’re joining a young company, you’re not just signing on for a job—you’re embedding yourself in a rapidly evolving environment where values, interpersonal dynamics, and even conflict resolution styles can change the course of the product’s future.
Amit points to a “zero-sum game” culture in large companies, which creates animosity between colleagues vying for promotions and furthering your career. As he describes it: “In large companies, mostly you end up playing zero-sum games, where your success means your neighbors lack of success because there are fixed promotion budgets and fixed budgets for teams in terms of comp and things like that.”
That environment can stifle true innovation. At startups, meanwhile, you have fewer layers, and success is typically a collective goal. You can’t hide behind departmental silos. Everyone’s success is intertwined.
Dheeraj points out here that during conflicts in startups, the tiebreaker is always the end user. This emphasis on the user fosters a healthy approach to conflict. Conflict is inevitable in any environment that encourages ambition. There could see differences in product direction, arguments over resource allocation, or tension about which user segment to prioritize first. But the secret is to reframe conflict as an opportunity for learning rather than a sign of dysfunction.
Then there’s the question of hiring employees across the globe. Dheeraj adds that candidates should also evaluate a company on whether they have a “taste for talent” while building the company—their ability to attract candidates from a global talent pool and building robust distributed systems that work like a single system together.
To have a healthy startup culture, he adds that founders must visit the offices located across the globe in person and maintain the human touch, so that the employees don’t feel like mere remote workers, but “employees who happen to be distant.” This way, startups can build non-monolithic systems with diverse employees that last longer and are more efficient than monolithic systems where most hires come from a similar background, Dheeraj emphasizes.
You need to build a distributed system that works on these individual nodes and then yet creates this facade of a single system. This, to me, is a really important way to build non- monolithic systems that probably will have a longer staying power than if you create a monolithic culture that’s just sitting in one city.
Wrapping up: Making the leap
What ultimately resonates from the conversation between Amit and Dheeraj is that startups represent an ultimate test of self-discovery. You find out who you really are once you can handle an environment defined by conflict, open-ended goals, and rapid shifts in direction.
“You should always be jumping into an entrepreneurial journey unless there’s certain things that hold you back,” Amit says, adding that candidates looking to join startups should introspect to see whether they’re facing self-doubt, having an impostor syndrome, or even financial commitments that hold them back from making the jump.
Whether you’re eyeing a role as an early engineer at a new AI venture or considering launching your own company, the impetus is similar: you want to push your limits, forge new intellectual ground, and potentially craft solutions that alter entire industries. Yes, you can cling to steady paychecks and known career ladders, but you risk waking up a decade later realizing you never quite stretched your capacity for learning—or for contribution.
Evaluate whether you can. Embrace the risk if you’re willing to value learning above short-term comfort. And your startup journey will be truly worth every effort.
As Dheeraj puts it succinctly: “You can never go wrong if you’ve got the ability to respect the process of building a company.”
And if you’re craving more ideas on embracing risk, refining your product design, or just hearing firsthand how leaders navigate startup chaos, head over to The Effortless Podcast Substack, where each new post peels back more layers of what it takes to build, lead, and scale with momentum.
