#5 Challenges of Being an Entrepreneur

The most pressing initial challenge of an entrepreneur is assembling a competent team of co-founders

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Every triumphant entrepreneur has had his share of grapples and mishaps before he could bring home the bacon. You will seldom come across an enterpreneur who does not have an interesting tale to narrate about the challenges he faced during his voyage.


The most pressing initial challenge of an entrepreneur is assembling a competent team of co-founders with a motive of making mobile app engagement more relevant, contextual and subsequently personalized. Our POA was to build the ver.1 of the concept and make sure the product is effectively solving a real world problem.

Having understood the modalities of user platforms, my Co-founders and I started exploring the scope of re-targeting the same set of users and convert them into potential clients. As techies with decades of experience our compatibility was instantaneous. We had worked together as a team with a unified target of making an evolved product which could solve real-time problems and thus giving positive impact on our product and customers in-turn.

From an Organized Structure to Bootstrap Mode  

Post working in an organized corporate structure, switching over to the bootstrap mode was an alluring challenge, but that wasn’t something which could pose a hurdle considering the excitement building something from the ground up entails. Essentially we needed a space to bundle up but a shoe-string budget did not allow us the luxury of having an office at the outset. Our friends at Freecharge extended an olive branch by sharing their office space with us. This leg room enabled us to kick start on a collaborative note.

Test Run Results were Satisfying

Being techies at heart, all three of us could easily switch over to core programming without a glitch. Soon the test runs were initiated to ratify the efficacy of the product. The results were extremely satisfying. However, very often what might appear as infallible gold in an entrepreneur’s eyes might not win favor in a customer’s view. Thus, securing our first major customer was a sizable challenge. We bagged our first customer in BookMyShow. Considering the quantum of operations at which BookMyShow was doing business, it not only reinstated our claim of a dire need for a product like ours, it also provided a much-needed throttle to our conviction and confidence.

Challenge of Securing Funds

Our next challenge came in the form of seeking and securing funding. Experienced entrepreneurs have an edge over newcomers when it comes to sourcing funds for a new business. Looking at the inherent potential of the product, the initial round of funding worth USD 1.6 million came from Accel Partners in seed funding in the year 2014. Once we had received seed capital; our next challenge was to prioritize the allocation of these precious financial resources. These funds were eventually directed towards sourcing a competent team, setting up a conducive workplace and amplifying product development. Subsequently, in the next round of funding in August, 2015 we raised USD 8.0 million from Sequoia Capital, India and Accel Partners in Series A funding. Since then there has been no looking back.

In essence, no entrepreneur’s journey is ever without challenges and obstacles; that have to be overcome. That is precisely what makes the entire journey exciting, rewarding and fulfilling. Creating value and positively touching businesses and consumer lives is an altogether great feeling.

Anand Jain

Written By

Anand Jain is currently the Co-Founder of CleverTap. Previously, he was the founding CTO of burrp.com, India’s largest local reviews and recommendations platform of Mumbai. burrp.com was acquired in 2009 by the publicly traded yellow pages company, Infomedia 18 Ltd (now merged with Network 18). Prior to burrp.com, Anand was based out of the US - in Seattle and San Francisco, where he has worked with Motorola, AT&T and Brience. Anand has more than two decades of experience architecting and building software. He's a management professional with significant experience leading engineering, design, quality and IT teams.