Creative Capital for Growing Small and Mid-Sized Businesses
Flexible capital. Operator mindset. Long-term partnership.
“The right capital partner doesn’t just fund growth — they accelerate it by bringing experience, strategy, and the right connections.”
— Kevin Harrington, Shark Tank Investor
Chessler Holdings Partners with Kevin Harrington
David Chessler and Original Shark from Shark Tank Kevin Harrington sit down to discuss the compelling investment opportunity at Automated Retail Technologies(ART), a Chessler Holdings portfolio company.
Investing at the Intersection of Capital and Creativity
We provide flexible capital solutions for businesses that need more than a traditional lender or a passive financial sponsor. We focus on situations where structure, creativity, and speed matter. Our work spans asset-based lending, growth capital, turnarounds, and complex workouts.
Asset-Based Lending
Asset-based lending solutions to businesses with strong assets and working capital needs.
Growth Capital
Growth capital for small- and mid-sized companies scaling proven business models.
Turnarounds & Special Situations
Turnarounds and special situations where experience and structured capital are critical.
Strategic Partnerships
Strategic partnerships that help portfolio companies access connectivity, media, and technology ecosystems.
Led by Investor and Entrepreneur David Chessler
David Chessler has built, operated, and invested in businesses for more than two decades, beginning as the founder of ParView, one of the early telematics and GPS-based asset tracking companies. After a successful exit, he has continued to back companies across technology, media, and connected devices through Chessler Holdings and related investment vehicles.
Proven Experience That Drives Results
~20
Portfolio Companies Across Technology, Telematics, Media, and Entertainment
100%
Founder-Focused Partnering Closely with Operators to Scale Businesses
20+
Years of Investing in Small and Mid-Sized Businesses
Active Partnership
Strategic Capital
Operational Support
Industry Expertise
Long-Term Value
Growth Focus
Where We Invest
Chessler Holdings invests in sectors where we have deep expertise and strong industry relationships, particularly in connected devices, automated retail, media, and location-based experiences.
Connected Technology Solutions
Digital Media Platforms
Smart Kiosk Experiences
Tech-Enabled Services
Niche Value Sectors
Shark Experience - an on-course, cart-based golf platform that uses connected touchscreens and speakers to deliver GPS yardages, hole flyovers, music, and live sports.
Edison Interactive - a cloud-based hospitality technology company that powers connected hotel, TV and golf cart screen systems, transforming guest-facing displays into intelligent, monetizable media platforms for operators.
Automated Retail Technologies - an innovative foodservice company that delivers hot, fresh meals and other treats through smart, unattended kiosks.
PlaySight - a sports technology company that turns courts, fields, gyms, and rinks into AI-powered Smart venues with connected camera systems for live streaming, video replay, and performance analytics across all levels of sport.
Brick Street Farms - a sustainable farming company that uses high-tech indoor vertical and hydroponic systems in repurposed shipping containers to grow fresh, pesticide-free greens year-round.
A Hands-on, Partnership-Driven Approach
We invest alongside entrepreneurs and management teams who value a partner that can help structure the right capital solution and remain engaged as the business grows or undergoes a turnaround. Our role ranges from board-level support to deeper involvement in strategy, capital structure, and key relationships.
Flexible structures across debt, equity, and hybrid capital
Focus on aligning incentives with founders and management teams
Willingness to work through complexity in distressed or special situations
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Access to a network of strategic partners and operating talent
Selected Portfolio Companies
Our portfolio includes technology and services companies that benefit from both capital and operational support. Here are a few representative examples.
Automated Retail Technologies
Smart vending machines provide 24/7 access to delicious food with easy installation and convenient payment options.
Edison Interactive
Edison Interactive is a cloud-based platform powering hotel TV systems and 3D golf cart GPS across hotels and golf courses.
Playsight
PlaySight SmartCourt AI technology powers athletes and teams worldwide with its connected camera platform for broadcast and player development.