Burn out caused Hirak Chakraborty to reassess his life, but it didn’t slow him down it just changed his focus from good enough to persistence.
What’s your story?
Small town kid from India. Big dreams. Bigger spreadsheets. Born into a family where optimism was currency and values were non-negotiable.
I swapped football cleats for financial models, trading spontaneity for strategy. Climbed from consulting to M&A, chasing deals like trophies – until exhaustion whispered a truth: success without meaning is just expensive emptiness.
Now I work at capitalism’s most interesting intersection: where technology meets transformation, where money marries meaning.
My journey taught me that your zip code predicts your start, but your conviction determines your finish. I’m still that small town guy, just with better questions.
What excites you most about your industry?
Controlled chaos. Methodical madness. IT / Tech, M&A, VC, startup – it’s where excel meets existentialism.
We don’t just move money, we value the future on conviction.
Next decade? AI drafts term sheets, blockchain executes them, humans decode the soul underneath. Outsiders see numbers, we see revolutions wearing suits.
Here’s what thrills me: every pitch deck is someone’s prayer, every deal closes with calculated faith. It’s capitalism infused with creativity, technicalities seasoned with stories.
The game isn’t won by the smartest analysts, it’s won by whoever spots patterns in chaos first. Value lives where courage meets capital.
What drives you in your career to push beyond what other people consider normal?
Simple: mediocrity is slow death. I watched “good enough” murder more dreams than failure ever could.
My fuel? Immigrant hunger mixed with midnight clarity, knowing that privilege unused is privilege wasted. Every deal I close, every founder I back, every implementation I wrestle at 2 AM is rebellion against settling. I’m haunted by opportunity costs and inspired by impossible math.
Here’s my framework: if comfortable, you’re coasting. If scared, you’re growing. If others say “maybe possible,” I’m already asking “why not inevitable?” Drive isn’t about working harder; it’s about refusing softer. Purpose & value add over pay check. Always.
What have been the most useful skills you have learnt and applied in your journey?
Four skills, infinite ROI.
Pattern recognition: I spot gold where others see gravel. Luck is just preparedness with better glasses.
Storytelling: Technical and pricing models don’t close deals, narratives do. I translate boring barrage of presentations into human belief systems.
Listening: Silence in negotiations reveals more than words. Truth hides in pauses. Grab more with eyes and ears.
Resilience: Survived wrong advices, misdirected transformation journeys, ego traps. Taught me elasticity matters more than strength.
My framework? Marry analytics with intuition. Together they build trust, not just transactions. Market rewards intelligence, relationships reward intelligence with humanity. Master both. Win everything.
What’s the best piece of advice you ever received?
Two.
“Those whom you watch on TV don’t have time to watch TV”. My mother. One of the wisest women I ever met. During my school days. That line set the tone of my focus in everything.
“Don’t confuse movement with progress.” Six words. Seismic impact. Said by a mentor who watched me sprint through 16-hour days, collecting titles like Pokémon cards. It shattered me : beautifully. Since that conversation, I’ve built rhythm over rush, intention over intensity.
Paradox alert: slowing down accelerated everything. I measure days by depth, not speed. The trick isn’t running faster, it’s the direction that matters.
Who inspires you?
Not one person but a pattern. Persistence.
From Buffett’s patient capital to Musk’s reckless genius, from street vendors smiling through uncertainty to founders betting families on conviction – persistence is poetry in motion.
It’s the ultimate differentiator when talent becomes table stakes. This reshaped my leadership : I now hire for grit over pedigree, conviction over credentials.
My inspiration comes from old and young, senior and junior, my family and my kid. Sometimes wild animals too. So much to imbibe.
Titles expire. Grit compounds. When evaluating people or deals, I don’t ask “How smart?” I ask “How stubborn?” Persistence wins. Always.
What have you learnt recently that blew you away?
Two big things. Agentic AI & longer fasting
Terrifying. Exhilarating. Liberating.
It confirmed my thesis: technology amplifies character, not creates it. The future isn’t man versus machine. Winners will marry intuition with intelligence, empathy with algorithms. Here’s my framework : AI handles patterns, humans handle paradoxes. Machines optimize, we improvise. The edge isn’t resisting change. it’s riding it with your humanity intact. Stay human.
Fasting is not just ritual anymore. It’s part of my life. If one can follow 16 hours fasting schedule with proper calorie intake, body will say a thousand thanks. Allow the body to heal itself. Thank me later.
If you had your time again, what would you do differently?
Fail faster. Worry less. Exercise more. Repeat.
I wasted prime years seeking “the perfect move” when mastery lives in imperfect repetitions. Should’ve built messily, asked dumb questions to smart people, taken bigger bets on smaller data, looked after my health like my studies.
Here’s the painful truth: my caution cost more than my mistakes ever could.
My framework now? Speed over polish. Action over over-analysis. If you’re not occasionally unimpressed by what you shipped six months ago, you’re moving too slow. Market forgives wrong faster than it rewards late.
Move (literally). Learn. Iterate. Perfection is procrastination in a tuxedo.
How do you unwind?
Music, movies, books, podcasts, family chats.
Long walks where my mind negotiates with my heart.
I write. Half therapy, half rebellion against my corporate life, spreadsheet thinking.
Sometimes football matches, reminding myself not every goal deserves a business plan.
Unwinding isn’t escaping work. I do not believe in the work life balance thing ! What’s that ?
Some of my best ideas arrive not at my desk but between steps, between chats, between songs.
Here’s my playbook: your body needs rest, but your soul needs rhythm. Don’t just recover, reconnect. To music. To movement. To memory. Rest isn’t weakness. It’s strategy.
What is a major mindset change, belief shift or ‘ah ha’ moment that you’ve experienced in relation to your career?
When I stopped blaming the leaders around me for doing wrong things (which they did) and reconstructing my mindset around the fact that I am in the middle of a masterclass, on what Not To Do and how Not To Operate as a leader.
My mental health improved. My learning capacity improved, my assertiveness started impacting others. That was a major relief for me and my family.
Leadership isn’t being the smartest person in the room, it’s creating a room where others feel smart. I learnt through decoding the wrong steps taken by the senior corporate honchos around me.
Everyone in business should read this book:
“The Psychology of Money” by Morgan Housel. It’s a mirror disguised as a finance book, therapy hidden in chapters. While everyone hunts hacks, Housel reveals the real edge: behaviour beats brilliance. This book changed how I evaluate founders: I stopped asking “What’s your model?” and started asking “What’s your relationship with risk?” Read it. Your portfolio will thank you. Your soul might too.
“Elon Musk” by Walter Isaacson. Masterclass in controlled chaos. Vision, madness, genius, and grit woven together. It teaches that greatness isn’t neat or polite. It’s messy, relentless obsession with building the future while breaking the rules.
Shameless plug for your business or career:
I operate where strategy meets soul. The messy, beautiful intersection of Tech, M&A, VC, and Startups. I don’t just close deals, I connect multiverses. Technology to transformation, capital to conviction, founders to funders, ambition to accountability.
Clients reach out when they need clarity amid chaos, when tragedy needs turn around, when valuations need values.
Think investment warrior meets a mindful monk. I bring rigor without rigidity, analytics with empathy. Whether you’re building, buying, or betting on future, I’m your translator between what’s plausible and what’s profitable.
Best deals don’t just make sense financially, they do philosophically. Let’s build something meaningful.
How can people connect with you?
Best way is to reach out through LinkedIn (https://www.linkedin.com/in/hiraksc/). Or tag me in X (Twitter) – https://x.com/aamiHirak
Social Media Links?
https://www.linkedin.com/in/hiraksc/
This interview is part of the CallumConnects series.