For most of my career, I've held two identities simultaneously: the enterprise professional managing Fortune 500 relationships by day, and the entrepreneur building businesses in every other hour. Most people who know me from one world are surprised to learn about the other.
Why Both, Not Either/Or
The standard advice is to pick a lane. Quit your job, bet on yourself, build the startup. Or stay corporate, climb the ladder, get the comp. I rejected this framing because I think it's a false choice — and because the two paths made each other better.
Managing enterprise accounts at Sprinklr — Microsoft, Citi, Activision Blizzard — taught me how big organizations think, make decisions, and buy. That knowledge made me a dramatically better entrepreneur. I knew how to position, how to structure a deal, how to navigate procurement. Skills you can't fake.
And building businesses on the side made me a better CSM. I brought real operator empathy to client conversations. When a client talked about growth problems or operational complexity, I wasn't nodding along — I was living the same things.
The Real Cost
I won't pretend it's free. Doing both means early mornings, late nights, and weekends that other people spend recovering. There were stretches at Sprinklr where I was managing multi-million dollar accounts during the day and rebuilding Amazon PPC campaigns for Ramp Nutrition after my kids went to bed.
The cost is time and energy. The benefit is optionality. I've never been in a position where I felt trapped — where a job was my only path. That psychological freedom changes how you show up, how you negotiate, and how you take risks.
What I'd Tell Someone Starting Out
Don't quit your job to start something unless you have real evidence of demand. Use your employment to fund experimentation. Build systems, not just hustle. And find the intersection between what your day job teaches you and what the market needs — that's where the real leverage lives.
The goal was never to escape corporate life. It was to build enough that I always had a choice. That's still the goal.