ABOUT US
Investing With an Operator's Perspective
Building trust through experience, transparency, and long-term partnership.
Who We Are
Chessler Holdings is a Florida-based family office that invests in small and mid-sized businesses across the United States. We combine flexible capital with an operator's perspective, backing teams that need more than a traditional lender and value a thoughtful, long-term partner.
From our base in Sarasota, we have invested in companies across connected technology, telematics, media, and other sectors where we can add value through structure, relationships, and experience.
About David Chessler
David Chessler is a dynamic and innovative investor with a history of entrepreneurship, turnarounds, and value-added investments in small- to mid-cap companies. He began his career in 1994 by founding ParView, one of the early telematics companies providing remote monitoring and GPS-based asset tracking. After building the business, he led it through a successful exit to Ingersoll Rand.
Since leaving ParView, David has invested in a wide range of industries, from connected kiosks and telematics to media and content delivery. Today, he sits on numerous boards and serves as Managing Director of Chessler Holdings and related investment vehicles that specialize in growth capital, asset-based lending, and distressed or special situation investments.
More than two decades of experience as an entrepreneur and investor
Founder of ParView, an early telematics and GPS-based asset tracking company
Experience across growth capital, asset-based lending, turnarounds, and workouts
.svg)
Board roles across a diverse set of portfolio companies
How We Think About Partnership
We believe the best outcomes come from alignment among capital providers, management teams, and other stakeholders. Our goal is to structure capital in ways that support growth, protect downside, and give companies the time and flexibility they need to execute.
Asset-Based Lending
Asset-based lending solutions to businesses with strong assets and working capital needs.
Willingness to invest time and energy in complex situations
Growth capital for small- and mid-sized companies scaling proven business models
Focus on real businesses, real assets, and real cash flows
Turnarounds and special situations where experience and structured capital are critical
Emphasis on long-term relationships over short-term trades
Strategic partnerships that help portfolio companies access connectivity, media, and technology ecosystems
The Chessler Holdings Team
While David leads the firm, Chessler Holdings is supported by a small team and a broader network of partners and advisors who help evaluate opportunities and support portfolio companies.
Priya Sharma
Investment Director
2 to 3 sentences on relevant investing, operating, or financial experience.
Neha Kapoor
Principal
2 to 3 sentences on relevant investing, operating, or financial experience.
Karan Malhotra
Operations
2 to 3 sentences on relevant investing, operating, or financial experience.
From Sarasota to a National Footprint
Chessler Holdings was founded in 2004 and is headquartered in Sarasota, Florida. From this base, the firm has built a portfolio of approximately twenty companies across the United States, focusing on situations where flexible capital and hands-on involvement can make a meaningful difference drive exceptional value.
2004
~20
20+
1
.png)
Related Investment Platforms
In addition to Chessler Holdings, David is involved in other investment vehicles that participate in select transactions. These include platforms focused on growth capital investments, asset-based lending, and distressed opportunities.
Growth Capital Platform
Focused on growth capital investments for scaling companies with proven business models.
Asset-Based Lending
Providing flexible lending solutions backed by strong assets and working capital.
Special Situations
Distressed opportunities and complex situations requiring experience and structured capital.