Sidestarter Information

Why is the “typical" entrepreneur in their 20s or 30s and not their 50s, 60s or 70s? We challenge this. Why don't more CEOs start a side business as their best offense and defense for their company's future? We help them do this. Why don't advisors or family offices recommend to their clients to start a business to diversify their assets and legacy? We make it possible and elevate their relationship. For over 25 years, SideStarter has built and self-funded its own ventures, while also partnering with select experienced professionals to help them transform their ideas into meaningful companies. Inspired by the model of an Italian Renaissance bottega, we combine shared systems, expertise, and compounding learning to help businesses launch faster, operate smarter, and achieve lasting impact beyond traditional startup paths. We measure success not only by scale, but by purpose, legacy, and long-term impact. Our team has had the opportunity to work with C-Level executives at over 50% of the Fortune 500, 90% of the AmLaw 200, 1000s of business owners, and venture capitalists and elite professionals from most of the top names in the business world. We’ve helped them publish a book, lead a webinar, join advisory boards and even start a business. Throughout our team’s experience, we’ve seen first hand the incredible business ideas from more mature professionals, who aren’t sure how to get started or find the resources needed to bring their ideas to life - especially that works for them in their stage of life. Thus, a few years ago we launched SideStarter Ventures for this reason. SideStarter was founded in 1999 by Jonathan Aspatore and is headquartered just north of San Francisco in Marin County, California, with employees all across the United States, and an upcoming office set to open in Italy in 2027.