Fintech entrepreneur Sid Vasili launched his first business in 1976. Ahead of its time, HMSL was a business outsourcing company providing services such as accounting to global firms. Vasili later founded and sold three other businesses in fintech, including an invoice fraud detection and processing business that uses deep tech, robotics and artificial intelligence. A hands-on investor in early-stage startups within fintech, Vasili describes how his investment strategy operates on dual tracks — acquiring luxury watches as his passion and investing in startups to stay busy. Vasili founded his family office, Vasili Advisory, in 2018 after the acquisition of Invapay, the last business he sold.
How did you create your family office?
I decided to start a family office only using our funds, not external funds. I set up a fund that would look at investing in high tech and fintech startups. I didn’t want to be persuaded or dissuaded by others.
How do you manage your family office? 
In general, all funds are allocated to investing in high tech and fintech startups — no exceptions. I don’t want to redirect my thought process. We have investment funds in a general market structure rather than a specific startup investment. We’ve got a balance of risk in our external investment portfolio. We use a third-party adviser to manage those funds.
What are your investing principles?
Gut feel is one of them. Do I like the person? Do I believe they can do it? I meet the founders, and they do an investor presentation. I look at the proposition and market opportunity and customer acquisition. I then do some market analysis myself and make the decision. A lot of it is very, very close, personal engagement. Do I trust them? Do they have the right team in place that’s going to meet the market need? Is it scalable? I don’t want to invest in a local business. I want to invest in a business that has scalability. I’m very hands-on. We’ve had to work extremely hard to make the money, so we want to make sure the money works extremely hard for us. If they’re not interested in me being part of the board structure, I step back. It’s not for me.
Advice for others?
Take extra care in defining your investment strategy. Ensure that your investment principles are clearly articulated. Thoroughly research any investment opportunity. Ask for and seriously consider advice from trusted friends, family, and partners.
Amy Guttman, who conducted this interview, has been covering entrepreneurs and startups since 2014. She contributes to Forbes and has worked as a correspondent for the PBS Newshour, BBC, Associated Press, CBS News and others. Amy is a podcast presenter and regularly participates in tech summits around the world conducting fireside interviews, moderating panel discussions and speaking about how to tell compelling stories.