Never Before had I … till I did.

Reetu Gupta
4 min readNov 5, 2021

Today I’m feeling proud of myself. Proud of where I started and where I have come. As a founder, and before that a very ambitious professional, I always look forward through the windshield at all the things that had to be done, achievement to be had and dreams to be realized. Today, I had to take a peek in the rear-view mirror, and I was impressed by myself.

This week, an investor asked me a question. He asked if I had done anything like building a startup and raising funds before, because it’s a grind. This sent me on a self-exploration journey. I have never felt threatened by things I hadn’t done before. In fact, I believe, it’s more thrilling the first time.

Do you remember how you felt after your 2nd kiss or buying your 2nd car? Now how about your feelings after 1st kiss and 1st car? When we conquer something for the first time, there is a thrill of achieving something you didn’t have before. Taking your 1st company IPO must be a huge thrill because you don’t even know where the bell is on the NYSE desk. Second times, it won’t be the same excitement.

So I looked back at big events in my life and many things came to my mind that I had not done before till I did, which most people do not do.

· Never before had I graduated from MBA class as a valedictorian with perfect GPA and two young kids (1.5 and 4.5 yr old) and a full-time job managing almost 100 engineers all over the world, till I did.

· Never before had I managed a $500 million ARR product line and all the challenges that came with it including a factory shut down for five days in Penang, Malaysia due to a soldering ball station problem, till I did.

· Never before had I put my software for testing on a live Air Traffic Control system in Maastricht that controls whole Europe’s air traffic, within 9 months of joining a brand-new industry and company, till I did.

Never before had I quit a good six figure salary career where I was a high-flying executive 3rd from the top, to follow my passion and my gut of building a billion-dollar company, till I did.

· Never before had I cold emailed to India’s Prime Minister and gotten a meeting with his education staff, till I did.

· Never before had I given a solo talk in SxSwEdu, the biggest educational stage in the country, till I did.

· Never before had I woken up on a Sunday with my picture and story on two full center pages in Sunday Magazine of Seattle Times, till I did.

Never before had I the worst mom’s guilt when my middle school daughter thought $2 Oreo pack was too expensive and stayed hungry while I was in a 4-hour pitch practice in Portland, till I did.

· Never before had I shared my personal story in front of 1,000 people on a big stage in Seattle, with Satya Nadella was the keynote before my speech, till I did.

· On a personal note, never before had I revolted against my family and society to marry a guy from out of cast, till I did.

And the list continues and will continue. There are many many “Never Before… Till I did” stories in my life. Someday I’ll write a book about these.

Never before had I built a billion dollar exit company, till I will.

And here are the two endcaps to this list:

· · Never before had I packed 2 bags with $2,000 in my pocket and immigrated to a totally different country across the world, till I did.

· · Never before had I survived 5 life changing events in 6 weeks -starting an intense accelerator for my startup, being air lifted in a basket from the beach (mission impossible style) after a really bad hiking accident, only bread earner in our family losing his job, 1st child moving to college across the country and a Pitbull attacking our dog,2 kids and husband sending them all to ER, till I did this summer.

Interestingly each one of these events turned out to be the best things that could have happened. These all were blessings in disguise. Not only total outcome was beautiful, but I was also stronger after each one of these.

Only thing I’ll say —DREAM IT, WISH IT, DO IT!!!

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Reetu Gupta

Changing the world w/ Cirkled In (www.cirkledin.com), Dreamer, Doer; Entrepreneur, Marketer, Engineer; Daughter, Mom, Sister, UW Foster, NIT Kurukshetra India