Villi Iltchev raised $160 million for his debut seed fund, Category Ventures.Villi IltchevBulgaria-born Villi Iltchev built an unlikely career as an early investor in now-public GitLab generating $900 million in profits from one deal among other unicorns like Remote. Now with Category Ventures, hes hoping to do it again this time for himself.After years working on the Autopilot driver assistance software at Elon Musks Tesla, entrepreneur Ian Glow wasnt impressed by the investors circling his simulations startup, Zeromatter. Then he met with Villi Iltchev, a managing director at Two Sigma Ventures.Iltchev didnt need him to explain why computer simulations were valuable for any industry using sensors to train for safety exceptions, Glow said. And Iltchev didnt presume to tell Glow how to run his business, despite Zeromatter being not much more than a pitch deck at the time.Villi understood my life arc as it related to my business, said Glow, who decided to work with Iltchev over several name-brand firms. He knew that Id reported to Elon for a while, and I didnt want a boss in a VC.A Bulgarian immigrant who came to the U.S. alone as a teenager and scrapped his way through schools far from Stanford and the Ivy League, Iltchev took an uphill journey to the ranks of top VCs. He paid his dues in executive roles at companies including LifeLock, Salesforce and Box before becoming a full-time venture investor. Even then, he opted to take partner roles at smaller firms August Capital and Two Sigma over flashier brands. At age 48, hes not a hotshot new arrival. Where others post thought leadership bait on social media hoping to go viral, he shares pictures of his lost collection of old (mostly bootleg) tape cassettes.Soft-spoken but with a hyper-competitive personality, Iltchev has quietly built a venture track record that stands up to more pedigreed peers. When GitLab went public in 2021, his lead check in the $20 million Series B of the developer software maker in 2016 returned August Capitals entire $450 million fund more than twice over, generating hundreds of millions in profits from just one deal. (GitLab now trades at a market capitalization just under $10 billion.) In 2020 at Two Sigma, Iltchev led an $11 million seed round in Remote that valued the distributed work software maker at about $30 million, according to startup data tracker PitchBook; within two years, Remote raised $300 million in fresh funding at a valuation exceeding $3 billion.Now, Iltchev is looking to do it again this time as the boss at a new firm, Category Ventures. He has raised $160 million for Categorys first fund, which plans to write checks of $1.5 million to $5 million to pre-seed and seed-stage startups on his longtime turf of enterprise software. Focuses will include applications, infrastructure and developer tools, as well as artificial intelligence.Iltchev raised the fund alone, making it one of the larger first-time solo funds to debut in recent years. He does plan to add more partners in upcoming months, with a goal of building a lasting venture brand for the next several decades.I cant control my judgment always being right, and I cant control the outcomes, Iltchev told Forbes. What I can control is what I bring to the table in terms of my ability to help and do the hard work.In Bulgaria, Iltchevs father was a physicist with a PhD and his mother a civil engineer when its communist regime toppled in 1990, plunging both their careers into turmoil. He was 15 when they moved to nearby Greece, where his father took up construction work and his mother became a maid. Eager to improve his prospects, Iltchev applied to a number of boarding schools in the U.S. and the U.K., hoping to receive a scholarship, even if it meant leaving his family behind.When a small school in Georgia obliged, Iltchev jumped at the opportunity, quickly improving his English and parlaying his talent as a youth champion at tennis back in Bulgaria into another scholarship to a small Christian college in South Carolina. From there, he worked his way up the ladder: a graduate accounting degree from Clemson University led to a job at PwC; an MBA from the University of Virginia secured a ticket to San Francisco via a banking job at Merrill Lynch. Next, it was the tech industry itself, through a string of corporate development and strategy roles starting at HP in 2008, then Salesforce, LifeLock and Box, a startup he met and helped back through Salesforce Ventures, the tech giants venture capital arm.Iltchev was an executive at Box when it went public in January 2015.Associated PressAfter Boxs 2015 initial public offering, Iltchev considered launching his own small private equity firm, but settled upon venture investing as a young partner at a 20-year-old firm, August Capital. There, he backed GitLab and helped bring in SendBird and MaintainX, both of which later reached billion-dollar valuations. Then, in late 2018, August imploded. Tempted to launch his own fund, Iltchev met with potential backers but ultimately balked. Instead, he joined Two Sigma Ventures, the venture arm of the multi-billion-dollar trading firm Two Sigma.As Two Sigmas billionaire founders began a messy public feud earlier this year (in August, they announced they would both step down as co-CEOs), Iltchev was growing restless. A market opportunity existed in venture, he believed, for a relatively bigger but still early-stage-only firm to take more ownership of seed rounds. An outfit like that could win head-to-head against multi-billion-dollar multi-stage firms he believed couldnt offer the same focus and hustle.Investors in venture funds, including funds-of-funds and institutions like the University of Chicago, were quick to agree. There are some excellent enterprise investors in the Bay Area, but they tend to sit in different kinds of vehicles, said Beezer Clarkson, who leads investing in venture funds for Sapphire Partners. Accolade Partners managing partner Atul Rustgi said Iltchevs track record was one of the best weve seen out there among first-time funds. His background is very important, too, said Rustgi. Working his ass off to come here and work his way up, thats motivation that is hard to quantify.Word of Iltchevs fundraising plans were first reported by The Wall Street Journal.Founders who worked with Iltchev said they werent surprised to see him launch Category. At startup Candu, cofounder and CEO Jonathan Anderson said Iltchev had made about 200 introductions for the product experience software startup since pre-empting its seed round, ten times more than other investors on the cap table. Hes exactly as he presents, Anderson said.When Iltchev does tell founders to rethink their strategies as he did at Candu about its pricing model, and more recently at Zeromatter, where CEO Glow resisted setting up even a simple corporate website that has since proven a major source of job applications hes often right, they added.A year ago, when one of Remotes cofounders was looking for a new place to live in San Francisco, Iltchev helped find him a nearby home, said CEO Job van der Voort. Theyre still happily next-door neighbors. Thats a pretty good data point that Villis a pleasant person to work with, said van der Voort. And apparently, he makes good pizza.For Iltchev, Category Ventures now represents the chance to build something for himself to outlast him finally, the face of the operation after a career as the self-described immigrant kid who had nobody, stumbling through.If I didnt do this, Id regret it. Its such an opportunity, Iltchev said. If I fall on my face, Ill be fine, and I want my kids to see it. And if Im successful, I want my kids to see that, too.