The Story Behind Haystack’s Investment In Pomerium

In early 2020, right smack before the pandemic arrived on our shores, my new colleague at the time, Aashay — not even a year out of college — surfaced this fledgling open source security company he found by doing some web research, Pomerium. We all reached out, talked to the founder, and encouraged him to come up from LA to meet us and some investors in the Bay Area. The creator’s name is Bobby DeSimone, and he took us up on our offer and visited SF.

We met Bobby a few times on that trip, introduced him to a bunch of investor friends, and tried to figure out if he wanted to raise capital for his project, and if we wanted to invest. Bobby left for home and thought about making one more trip in late February / early March 2020 to shore up the round. Bobby’s timing was unfortunately not great – various things began shutting down, then the NBA was suspended, and we were in full lock down mode. Somehow, we gained enough conviction in the opportunity and Bobby prior to the shut down, and so we joined Enrique Salem from Bain Capital and other friends like Kevin Mahaffey to co-lead Pomerium’s seed round in early March 2020.

Maybe Bobby’s timing was good. He took that seed round and embarked on the journey of turning his passion project into a full open source network and business. Along the way, other friends like Oleg from and others continue to support the company as it meandered through the product wilderness and dug in their heels for the very long product and feedback cycles with large enterprise users. Along the way, Bobby didn’t just face early-stage company building challenges — he also faced other challenges outside of work that made the world of startups less important, frankly. Bobby hung in there. There were times we thought to ourselves, will he tap out? We would’ve understood. But, he didn’t tap out.

I need to brag a bit about my partner, Aashay, here. Last summer, when Bobby finally felt ready to raise a bigger round of capital, he spent a LOT of time with Bobby refining the pitch, the vision, and the deck. Bobby is a builder, a quiet and deep thinker; he doesn’t play the VC game, and despite gaining real demonstrable traction with Pomerium, wasn’t as well versed at the time about how to “sell” the vision. Working with Aashay changed that, I can say that clearly watching up close first-hand.

So today is a sweet day for Bobby, for Pomerium, for Aashay, and for Haystack and our co-investor friends as the company announces their hard-earned Series A round, led by Eric Vishria at Benchmark Capital. You can read more about what Pomerium is up to by checking out the funding announcement here and blowing their Pomerium blog announcement here.

As you check out their site and offerings, I’d also encourage you to learn more about the ancient Roman concept of “Pomerium,” as well. While Bobby earned a bachelor’s degree in computer science, he also studied Latin and is a self-proclaimed history nerd, just like me, but I think he went a bit deeper on ancient civilizations.

He named the company “Pomerium” after the name around the wall inside Ancient Rome during the time of Julius Caesar. I love this line from the opening of the Wikipedia entry: “In legal terms, Rome existed only within its pomerium; everything beyond it was simply territory belonging to Rome.”

As the early-stage tech world begins to learn about Pomerium, you’ll start to see that Bobby’s original vision — inspiration drawn deep from history and bold in its modern security architecture — is perfectly positioned to offer large private and governmental organizations the highest precision secured access control in a world full of global cyber-espionage and novel, powerful, yet at times, slow and hallucinating, LLMs. We are very excited about the future of Pomerium and it’s been a pleasure to have been a part of the ride so far. Onward!