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Vinny Smith’s Investment Picks

Did Vinny Smith catch a 75-bagger with his early investment in Alteryx Inc.?

While he’s not revealing how big that home run was, it was clearly a winner. He began investing in the Irvine-based company in 2013 when it was valued at under $100 million. It now has a $7.6 billion market cap and it’s made a billionaire of Chief Executive Dean Stoecker (see separate story, this page).

We ranked Smith at No. 13 on our annual list of the wealthiest in Orange County, with an estimated net worth of $2.4 billion, or about a 20% increase from last year (see entry, page 14).

Smith’s initial fortune came from selling his Quest Software to Dell in 2012 for $2.4 billion. With the cash received, he began Toba Capital, which now has $1.1 billion in funds under management and is the largest venture capital firm based in Orange County.

Fifteen of Toba’s investments have been sold to other companies, while three more went public, including Alteryx, which we estimate Smith invested about $6 million in.

When Alteryx went public in 2017, Toba held a 7.2% stake. Since then, it’s been gradually selling its shares, although it still held a material stake earlier this year.

Toba has stakes in 38 companies, including several in OC.

The fun-loving Smith, who’s a golfer, skier and surfer, clearly has the Midas touch. When we asked Smith which of his investments we should keep an eye on, he pointed to these nine:

• NextVR Inc. of Newport Beach broadcasts live events in virtual reality. It has attracted Chinese investors, who in 2016 valued NextVR at close to $1 billion.

• Funraise Inc., based in Long Beach, built a fundraising platform that is designed to make scalability a priority for nonprofit entities. Toba led a Series A fundraising of $9.7 million last year.

• Conversica Inc. in Foster City makes artificial intelligence software that helps 2,000 companies worldwide generate sales and marketing ideas. The AI software, which can communicate in at least six languages, talks to potential sales prospects who have contacted a company through its websites, emails, texts or social media. Toba invested in a Series B round that raised $34 million in 2016.

• Coupang Corp., a South Korean e-retailer that generated about $2.4 billion in revenue in 2017, got a $9 billion valuation last year after its latest round, which included $2 billion from SoftBank.

• Deliveroo is a London-based restaurant delivery service that received a $3.5 billion valuation earlier this year after an investment round that included Amazon. It has 60,000 “riders” who deliver meals from a network of 80,000 restaurants. It has 2,500 employees in 500 towns and cities across 14 markets. It’s not yet in the U.S.

• PatientPop Inc. of Santa Monica supplies an all-in-one solution to doctors and other independent healthcare providers to improve every digital touchpoint of their patient’s journey. It has 400 employees. Toba was a sole investor that provided $10 million in 2015.

• Robinhood, a Silicon Valley startup, permits consumers to invest in stocks, ETFs, options, and cryptocurrencies from a phone or desktop. Its last Series E financing gave it a $7.6 billion valuation.

• Seal Software Ltd., a San Francisco-based firm that has a $30 million investment from Toba, permits corporations such as banks to use artificial intelligence to study contracts of any file type across their networks to quickly understand risks and place them in a centralized repository. Seal now has more than 250 employees including 30 on-staff lawyers.

• Wallarm, based in South San Francisco, is an AI startup focused on website security. Wallarm was ranked No. 7 in the security category in Inc. magazine’s 37th annual Inc. 5000. Toba led an $8 million Series A investment in 2018.

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Peter J. Brennan
Peter J. Brennan
With four decades of experience in journalism, Peter J. Brennan has built a career that spans diverse news topics and global coverage. From reporting on wars, narcotics trafficking, and natural disasters to analyzing business and financial markets, Peter’s work reflects a commitment to impactful storytelling. Peter’s association with the Orange County Business Journal began in 1997, where he worked until 2000 before moving to Bloomberg News. During his 15 years at Bloomberg, his reporting often influenced financial markets, with headlines and articles moving the market caps of major companies by hundreds of millions of dollars. In 2017, Peter returned to the Orange County Business Journal as Financial Editor, bringing his heavy business industry expertise. Over the years, he advanced to Executive Editor and, in 2024, was named Editor-in-Chief. Peter’s work has been featured in prestigious publications such as The New York Times and The Washington Post, and he has appeared on CNN, CBC, BBC, and Bloomberg TV. A Kiplinger Fellowship recipient at The Ohio State University, he leads the Business Journal with a dedication to uncovering stories that matter and shaping the local business community and beyond.
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