I didn’t stay in my lane!

What landing the lead investment in Perplexity taught me

IVP recently led a $73M Series B investment in Perplexity, the AI-powered knowledge engine and competitor to Google Search. The WSJ covered that news, and the NYT wrote rather glowingly about Perplexity and its potential.?

Perplexity was a highly sought-after AI venture-capital investment, and I encourage you to read more about why we believe in the company and founder/CEO Aravind Srinivas.?

This is, however, a different story. Or rather, a few intertwined stories about what winning Perplexity taught me about myself, as an investor, as a person. I was not the conventional choice to close this deal. To the contrary, I may have been one of the least likely general partners at IVP to close a lead investment in a consumer tech company as formidable as Perplexity. Because everyone knew I invested in infrastructure, not consumer, companies.?

Sure, I’ll describe the process required to get that term sheet signed. But even more than a roadmap to an investment that I’m hugely proud of, this is a story of the powerful lessons I learned along the way — about acting instinctively instead of overthinking; about ignoring self-imposed constraints; and about deciding when not to stay in my lane.

“Nobody, including me, expected me to suddenly hit the gas toward Perplexity”

Had I stayed in my traditional lane (Cack The Infrastructure Investor), IVP’s investment in Perplexity likely wouldn’t have happened. It wouldn’t have happened if I’d stopped to think about (or overthink and therefore question) what I was doing — the second-guessing so familiar to venture investors — or if I had continued to heed the singular, debilitating narrative about myself that I’ve carried around since childhood.?

If, if, if. In a flow state, you don’t deliberate, you just act — automatically, intuitively, seamlessly. So much of my work on the Perplexity investment felt much like an athletic flow state. As a professional runner for Nike after college, when a competitor overtook me, I didn’t waste time thinking about whether I should catch her, how long it would take or how much it would hurt. I just accelerated.?

“How did you win that?”

As a cloud infrastructure expert, I’ve made a living investing in technical products made for technical users — developers, CISOs and VPs of Engineering. Investing in consumer products like Perplexity was that “other lane” that I had always steered clear of.?

Nobody, including me, expected me to suddenly ignore the lane markers and hit the gas toward Perplexity like I did. When Clint Sharp, the CEO of Cribl, an IVP portfolio company, found out I had been point on the deal, his very candid response was, “How did you win that?” His emphasis was on the you.

Fair question! One I’d asked myself. It started, of course, with executing on all the fundamentals of investing and then hustling — really hustling.??

Perplexity’s founder and CEO, Aravind Srinivas, understood from the very beginning of our interaction that we believed in him and what he was building. From a distance this process can seem purely tactical. But our animating ethos in courting Aravind over the course of weeks was one of commitment, persistence and unwavering presence.?

If our meetings with him ran over time, we cleared our calendars and kept going. We personalized each interaction with him, making a point to meet face-to-face instead of over Zoom, sharing meals at local restaurants and inviting him to a VIP retreat with other CEOs, demonstrating a command focus on not just him but the experience he was having with us — every one of us. All those small, genuine gestures matter.?

“I was resolved, and that resolve saved me”

It began with an informal meeting on a Friday afternoon in late September.?

Aravind had invited me to Perplexity’s San Francisco office for a quick half-hour chat. Had it been over Zoom, this would have been the end of the story. But as we talked, 30 minutes gave way to 60, then 90, then 120 as our investment conversation deepened. Together Aravind and I went through a metamorphosis of a Friday afternoon. Whatever early-weekend plans either of us had made went out the window.?

I continued asking questions, Aravind continued answering them, I posed more questions….flow state.?

By the time I finally left, we’d made plans for Aravind to meet IVP’s entire investment team. Six weeks and an incredible amount of work later, we had a signed term sheet.?

Instead of doubts, resolve?

Many investors believe the hardest part of venture capital is deciding, yes or no, whether to invest in a company. That part is, indeed, difficult — because the stakes are so high and we’re often wrong. But I believe an earlier decision in the investing process is the single hardest one to make: whether or not to even pursue an investment opportunity. Because doing so requires devoting yourself entirely to an idea, a process, a team, and giving it everything you can give.?

Coming out of that meeting with Aravind, I never even questioned whether to pursue Perplexity. I was resolved, and that resolve saved me.?

It saved me from questioning whether someone on the investment team who is more consumer focused should take over and lead the process. Because, after all, I’m Cack The Infrastructure Investor. I could very reasonably have concluded that we would be better positioned to win if one of my partners took over.?

In our weekend emails one of them had noted, completely in good faith, “One idea is to recruit some of the Consumer team.” He was right, of course, and we did augment our deal with that consumer DNA, and to great impact.?

My resolve also saved me from a more personal, irrational burden: questioning whether I was smart enough. Childhood labels are powerful and tough to erase. In my family, I understood my sister was the smart one, I was the athlete. In Sibling Rivalry, the follow-up book to a classic parenting book by Adele Faber and Elaine Mazlish, the authors state, “We, as parents, have it within our power to help free our children from the prison of their rigid roles.” I do exactly that for my kids but have sometimes struggled — irrationally, I know — to do it for myself.??

But I’m working on it. At a IVP-sponsored founder retreat recently, in response to my declared intention to be more assertive in the firmwide weekly meetings, the moderator asked me: “What narrative would you have to give up to make that a reality?” I’d have to give up the narrative that my sister was the smart one and I was the dumb one.?

We can both be the smart ones.?