Keshav Maheshwari is a second-generation entrepreneur from the family behind ALLEN Career Institute. However, his story is not one of inheritance but of intentional reinvention. As the managing director of ALLEN Overseas, Mr Maheshwari is expanding the institute’s footprint across the Middle East and beyond, reimagining coaching and academic support for the global Indian diaspora.

A Computer Science graduate from BITS Pilani (Dubai Campus) with an MBA in Family Business Management from SP Jain School of Global Management, he has lived, studied and worked across Dubai, Mumbai, Singapore and Sydney. Mr Maheshwari has also worked in various roles at EY, Zomato and early-stage startups and gained deep insights into market behaviour, operational scaling and digital transformation. In an engaging conversation with Sharmila Chand, Mr Maheshwari provides interesting insights into his personal and professional lives.

How did your journey as an entrepreneur begin?
I come from the legacy of ALLEN Career Institute, a brand built over decades by my family. But I did not intend simply to inherit my family legacy early on. I wanted to reshape and future-proof our institution in changing times. I started by immersing myself in every part of the business from classrooms and students’ feedback to technology and digital outreach. As managing director of ALLEN Overseas, I have led the transformation from a primarily-offline coaching institute to a hybrid, tech-led education enterprise. When COVID struck, instead of simply preserving the existing model, I pushed for rethinking how we deliver value even if it meant challenging tradition.

What are the key lessons learnt along the way?
Over time, several core lessons have become non-negotiables for me:

·         Processes must win over personalities: In family-run businesses, it is easy to let egos dominate decisions. But for scalability and consistency, you need systems that outlast any individual.

·         Change is the only constant: In education, digital overtook offline. Then the pendulum swung back. You must be nimble and prepared to reinvent.

·         Think in decades, not months: Every move should be strategic and forward-looking, not just reactive or short-term.

·         Growth over continuity: Continuity is important. But the focus should always be on enabling growth building the future rather than resting on past glories.

What are the kinds of challenges you faced, and how did you tackle them?
One of the biggest challenges was the existential shock that COVID brought to a brick-and-mortar coaching model. Overnight, physical classrooms could not function. Many institutions simply ported content online and lost their academic essence. I knew that would not suffice.

So, we took a dual approach: We re-engineered how lessons are delivered, building a technology-first platform, while preserving interactive pedagogy. We shifted mindsets internally, persuading faculty and staff to embrace new roles, new processes and to see technology as an enabler, not a threat.

The result: ALLEN became a hybrid model, combining online and offline, where the learning value for a student remains constant, regardless of channel.

What is that one trick which has helped you keep your work and personal life balanced?
The trick (or habit) I lean on is deliberate boundary-setting, carving fixed “off hours” or “no meeting slots” and respecting them as non-negotiable. In those hours, I do not check work email or take business calls. This protects mental space. Also, I schedule rest, hobbies and family time as if they were meetings, giving them equal weight.

How do you de-stress?
Music is a trusted reset button for me. I enjoy singing and playing guitar, and sometimes, I just plug into an instrument and lose track of time. I also like to take short breaks for a walk, reading something non-business or catching up with family and friends. Those little pockets of disconnection help me come back with clarity.

Do you play any game which helps you in your work?
I would not say that I play competitive games regularly. But I do enjoy strategy-based puzzles or mind games (like chess, logic puzzles). These sharpen my ability to forecast moves, think multiple steps ahead and hold patience. In business, you often need to plan not just for today, but anticipate reactions, counter-moves and adapt accordingly. Such games help discipline strategic thinking under constraints.

The broader lesson is to never rush into a move without assessing many possible outcomes; stay calm under pressure; and sometimes, sacrifice a small advantage today for a more sustainable win tomorrow.

What message would you like to give to youngsters on keeping work and personal life balanced?

·         Be intentional: Do not let life be dictated by the next meeting or the next deadline. Schedule family, rest and passion pursuits just like you do business tasks.

·         Protect your boundaries: Work expands to fill all available time, unless you draw a clear line.

·         Know your non-negotiables: Identify the minimal personal rituals (dinner with family, quiet time) you must maintain, and defend them.

·         Learn to switch off: Modern tools make us always reachable; practise disconnecting.

·         Pace yourself: A career is a marathon, not a sprint. Burning out early does not help your long-term journey.

What are you most passionate about?
I am deeply passionate about transforming legacy institutions into future-ready ones. That means blending tradition with innovation, preserving values but evolving delivery. Also, I care about helping next-gen entrepreneurs (especially in family businesses) to navigate the tricky transitions of legacy, identity, systems and ego. My podcast, The Keshav Konnect, is a part of that mission.

What lessons have you learnt in life as an entrepreneur?

·         Systems outlast people: Build scalable processes, not personal dependencies.

·         Resilience is built, not given: In disruption, you survive by adapting and reinventing.

·         Think long-term: Decisions should anchor the journey over years, not just quarters.

·         Ego is your enemy: In family business especially, detaching personal ego from business decisions is vital.

How would you like to define yourself?
I would define myself as a learner before a leader. Titles and designations are temporary, what stays is curiosity and the hunger to evolve. I see myself as someone trying to balance legacy with innovation deeply rooted in values, but never afraid to question convention. My journey is really about shaping an institution that continues to impact lives long after we are gone.