Hi, it’s Sri! This is a weekly newsletter that’s part public diary and mostly essays on tech, policy, and finance. To receive this newsletter in your inbox each week, subscribe here. You can also find me on Twitter.
All opinions and thoughts are my own and do not reflect the views of any organizations I’m affiliated with. My writing should not be misconstrued as financial advice.
I only learned about venture capital once I started working on my company. I knew of venture capitalists-- there was press about VCs doing this and that-- but I didn’t know what they did.
I started my company-- Wordsmith AI-- during my master’s program. We spent many hours in the basement of Stanford’s engineering school, a part of campus I rarely spent time at as an undergrad. My friends joked that I transitioned to the “dark side”, going from studying the social sciences to becoming a “techie”.
But my engineering classmates and I were eager, and our professors filled our brains with notions that we could change the world. I posted sticky notes on whiteboards for my design thinking classes, felt immensely stupid as I debugged code next to my computer science friends, and pitched my company in front of strangers.
My brilliant cofounder Nishit and I had a vision to disrupt how we write. We wanted to build a Grammarly on steroids. This was pre-GPT-3 and before Google’s suggested email responses. Not only would it be a fancy spellcheck, but our product would also autocomplete sentences-- we were on a desperate mission to save people from email.
Our professors-- Pedram, Perry, and Jeremy-- pushed us, wanting us to be better. They asked us questions like why can’t Google do this? Who’s your target audience? Why writers? Who will pay for this?
These were all good questions, and it’s easy to look back and see all the things that went wrong, especially now being an investor. But at the moment, we tried our best. We pivoted and built out a mediocre minimum viable product, applied to accelerator programs, and pitched to VCs. Our professors warned that fundraising from a VC is like a marriage, and if all goes well, the relationship can last many, many years.
Some were so kind, like Heidi, who took a group of twelve students under her wing, along with Tina, through the Threshold Ventures Fellowship program. The pair taught us things like how it’s important to send a thank-you note to anyone who’s helped you. And my fellow cohort members were supportive even though I was checked out from our hangouts, panicked about my company’s future.
Other investors we met were also generous with their time, genuinely offering to help. One met with us at a cafe and connected us with another entrepreneur. Another invited us to their office and shared product advice. Others answered our questions over emails, made intros, and gave feedback to our pitches.
But I also met a few investors that I strive not to be. I was shocked at their rudeness, entitlement, and dismissiveness. Some only talked to my male cofounder, completely ignoring me. One was on his phone the entire time we spoke to him. Another one never showed up to the meeting.
In the end, Wordsmith AI didn’t end up working out. Nishit was beholden to his student visa, with another year left for his degree. I was graduating with my master’s, and I didn’t have the confidence to go full-time on it alone.
There was an immense sense of loss when we decided to quit. Everything that we had worked towards that year felt pointless-- all those hours spent hunched over metal tables in Blackwelder’s library, nearly a hundred user interviews wasted, our GitHub repository a relic of what could have been. We felt defeated, ashamed to even announce the company’s shutdown to the couple hundred users we managed to get.
It’s a well-known statistic that 90% of companies fail. But because my identity was so wrapped up with the company’s, I felt stupid. I couldn’t separate who I was from my company’s success, and I felt as though I had nothing to show for all the work that went towards building Wordsmith AI.
We couldn’t make it happen. But now that I’m sitting on the other side of the table, I think about those feelings-- how important my company felt to me back then, how much I wanted to see our product in the world, how much the failure stung. These feelings serve as reminders when I speak to founders today as an investor because, truthfully, they’re the ones making it happen.
Thanks for reading! Would love to hear from you if this resonated at all. You can respond back to this email, or find me on Twitter. Subscribe here to receive this newsletter in your inbox each week: