Why Investor Ankush Gera Wants Entrepreneurs to Rethink Success

What does it truly mean to succeed as an entrepreneur? This is a question that would typically lead to discussions of lucrative exits, massive returns, and global recognition. Yet, seasoned investor and founder Ankush Gera, believes there is much more to this question than people would realize at first.

When Gera started his entrepreneurial journey back in the 2000s, his notion of success was not too different from the one held by so many founders. Today, after having founded three successful startups, all of them which he originally bootstrapped, and as an angel investor with close to 150 deals under his belt, Gera knows better than to equate a goal with the idea of success. This is because in his eyes, doing so is often troublesome both for the individual and the collective.

“We put entrepreneurs on a high pedestal simply for reaching an exit or IPO or raising millions of dollars in seed funding,” says Gera, who achieved those same milestones across most of the startups he founded. “Unfortunately, these metrics often fail to capture the whole picture of someone’s journey and impact. In fact, we are seeing a steady increase in the number of ‘successful’ people who turn out to be malicious actors, or just incompetent altogether.”

Gera has backed close to 150 startups and funds, including names as iconic as Airbnb, Devoted Health, and Cloudability over the past 10 years, meaning he has seen all sorts of founders. This, combined with his personal experiences as a founder and leader –including Junglee Games, which earned revenues of $300M – has allowed him to reevaluate his idea of success several times, something that hasn’t been an easy task.

“Reevaluating your goals can be quite a difficult task, but questioning what it means for you to succeed in life is on a whole different level,” explains Gera. “Doing so forces you to challenge assumptions about achievement and status ingrained in you by society, friends, family, and yourself since childhood. For me, this meant realizing that financial success and fame alone didn’t lead to lasting fulfillment.”

Gera talked about this process in a recent podcast with Grit Daily’s Phillip Lanos, where he expressed that his focus as a founder and investor early on was all about generating a higher return. Achieving this cost Gera “blood, sweat, and tears” only to realize that what they built might not have been as impactful as they would have imagined after paying the price.

“There are two ways you can go up from that point. You either remain a builder and move to create something new and more meaningful, or you can become a supporter by capitalizing on your previous success to help others achieve their vision,” adds Gera, who chose the latter after remaining a builder himself for several cycles. “While both options are completely valid, I found it easier to find a deeper purpose by supporting other people’s visions, it is only a matter of finding the right people.

Gera points to the epidemic of founder burnout as indicative of an unhealthy obsession with overnight success and scale. Such an obsession, he thinks, is not only unsustainable in the long term but also leads to a perpetuation of the same narrative. 

“Penelope’s shroud comes to mind when I think about the loop most founders fall into,” explains Gera, referring to the burial shroud Odysseus’ wife pretended to weave every day to delay her suitors, only to unravel it each night. ”Many founders get stuck in this unsatisfying loop, chasing the next funding round or exit without stopping to ensure their business vision aligns with their personal values.”  

The way to break the look, Gera believes, requires people to redefine their concept of “success” by understanding that no matter what idea you have, it shouldn’t occur in a vacuum. By regularly reconnecting with their values, motivations, and needs, entrepreneurs can ensure that their definition of success better aligns with their deeper purpose. A difficult task? Certainly, but so is getting a business off the ground in the first place.