On to the 8th Mile

Reflections on the past year and on turning 27

Jay Kapoor
Jay Kapoor
2 min readOct 26, 2016

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The 7th mile of the Bronx 10 mile race this year kicked my ass.

I was dehydrated, cramped, going much slower than I had ever run or really, ever expected to run. I was angry, confused, frustrated and dejected. I wanted someone to blame so I got mad at all the runners passing me. I imagined all my friends at the finish line having a blast and celebrating while I struggled to just put one leg in front of the other.

It sucked. It hurt. I always put the pressure of success on myself but during that mile, I couldn’t have cared less if I failed.

Then luckily, after many agonizing minutes and five-thousand two-hundred and eighty feet — it was over. I was on Mile 8 and I found my second wind.

Year 26 was my 7th mile. It kicked my ass.

It sucked. It hurt. I pressured myself to succeed but at times I was hoping to fail just so I could stop trying. I felt like I had undone all the progress I had made to date in my career and on my health. I looked for reasons why it all went sideways and found only myself to blame. Which only made it worse.

But 365 days later, it’s over. I’m here. I’m still running.

I owe that to the love and support of my family and friends, who put up with me over the last year and encouraged me to keep moving forward. Always.

I’m still here. I’m still running. I’ve found my second wind.

It’s on to the 8th mile. It’s on to Year 27.

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Jay Kapoor
Jay Kapoor

Seed & Early Stage VC investor | I read and write about Tech, Media, SaaS, & Investing | Don’t be afraid of failure. Be afraid of being ordinary.