Osprey seeks to invest capital in niche-dominant, small- to mid-market companies/properties in a diversified fashion. Osprey holds equity positions in business services, commercial real estate, multi-family real estate, retail and manufacturing sectors.

DHR Global

HEADQUARTERS|Chicago, Illinois

Founded in 1989, DHR International is a leading, privately held provider of executive search solutions with over 50 wholly-owned offices spanning the globe.Read more


HEADQUARTERS|Chicago, Illinois

Founded in 1996, JobPlex was created initially to serve the middle management executive search market.Read more

Hertz Arena


Home to the Florida Everblades, Hertz Arena serves as a multi-use 7,181 seat arena hosting concerts, expos and more + 2 additional skating rinks for league play and community ice skating.Read more

Florida Everblades


The Florida Everblades are a minor league ice hockey team based in Estero, Florida; near Fort Myers, FL. They play in the ECHL and are affiliated with the Nashville Predators of the National Hockey League and the Milwaukee Admirals of the American Hockey League as of the 2019–20 season.Read more

5 Star Valet


Five Star Valet specializes in providing resort style valet parking services for hotels, resorts, restaurants, country clubs, shopping centers, corporate and community events. You only get one chance to make a good impression at your front door. Let our friendly and experienced valet associates handle the responsibility of providing a “Five Star” greeting to all of your customers or guests.Read more

Air Hoffmann

HEADQUARTERS|Chicago Executive Airport (Palwaukee, Illinois)

Air Hoffmann is an aviation services company that provides flexible point-to-point travel for today’s business leaders.Read more

American Farms


American Farms supplies annual and perennial flowers to FL and other regions through it's 100+ acre farm in Naples, FLRead more

Archer Wire


Archer Wire forms and finishes wire and metal products for a variety of industries. Read more

Augsta Wine Co.


Augusta Winery, founded in 1988, is located in the scenic town of Augusta Missouri which is nestled on the bluffs overlooking the Missouri River Valley.Read more

Balducci Vineyards


At Balducci Vineyards, family traditions run as deep as the roots in the rich soil. While the traditions started generations ago, the roots took hold in 1987 when Rick and Carol bought land in a Missouri river valley located in Augusta, Missouri.Read more

BaseCamp Executive Suites


Premiere executive suites & co-working space in Avon, CORead more

Board Prospects


BoardProspects.com is the world's largest boardroom community - providing its members with the latest in corporate governance news, education and board recruitment solutions.Read more

Coral Cay Adventure Golf


One of Naples’ top rated activities, Coral Cay Adventure Golf offers fun for adults as well as kids at this tropical mini golf course complete with caves, reefs, waterfalls, and harbor.Read more

Everglades Excursions


Let the experienced tour guides show you the mystery and ecology of the Everglades on a private excursion.Read more

Ferche Frames


Ferche Frames are the best commercial and architectural wood door frames available.Read more

Ferche Lumber


Ferche's Central Tennessee lumber concentration facility is the best in the Appalachian region. Read more

Ferche Millwork


Ferche Millwork is a full line of hardwood mouldings, veneered millwork, standard door components, OEM products and custom products. Read more

Global Jetcare


Provides global air ambulance services with dispatch in as little as 90 mins.Read more

GlobalWorks Events & Destination Management

HEADQUARTERS|Naples, Florida

GlobalWorks Events & Destination Management offers a full service one stop shopping experience for all of your destination management and event planning needs.Read more

Hillermann Nursery


Provider of landscape services, nursery and hardscape to the Greater St. Louis area.Read more

Hoffmann Creative Agency

HEADQUARTERS|Naples, Florida

Hoffmann Creative Agency is a comprehensive marketing company that oversees aspects of branding and advertising for Osprey Capital's holdings as part of the Hoffmann Family of Companies.Read more

Hoffmann Commercial Real Estate

HEADQUARTERS|St. Louis, Missouri

Hoffmann Commercial Real Estate is headquartered in St. Louis, MO and is an established real estate holding company.Read more

Hoffmann Executive Suites

HEADQUARTERS|Naples, Florida

Located in Naples, FL Hoffmann Executive Suites stands out as one of the best locations for an executive's office.Read more

Hoffmann Leasing Corporation

HEADQUARTERS|Chicago, Illinois

Hoffmann Leasing Corporation is a capital equipment leasing company that provides capital for businesses to obtain equipment in an efficient and cost effective manner.Read more

Hoffmann Media Group


Hoffmann Media Group, publishers of nine national publicationsRead more

Hoffmann Restaurant Group

HEADQUARTERS|Naples, Florida

Hoffmann Restaurant Group is a holding company comprised of notable restaurants throughout the United States.Read more

Hoffmann Sanitizing Services


Fully licensed and insured technicians using state of the art electrostatic fogging machines and CDC approved COVID killing chemicals to sanitize SWFL area businesses.Read more

The Java Butler


The Java Butler offers businesses throughout Fort Myers a wide range of premier coffee products selected with an Italian roaster, to add warmth and productivity to your establishment. We strive to be up to date with the latest, most efficient equipment for your office.Read more

Kaleidoscope Floral & Home


Kaleidoscope Floral is a luxury full-service floral design company based in Naples, Fl. Creating a completely customized event experience as well as premiere florals for the home, Kaleidoscope Floral continues to strive to be the leading standard in the industry. Read more

Kirkland Event & Destination Services

HEADQUARTERS|Lake Worth, Florida

​Kirkland Event and Destination Services prides itself on being your eyes and ears in South Florida working tirelessly to create a program to fit your specific needs and budget. Read more

Lark & Willow Events

HEADQUARTERS|Naples, Florida

Lark & Willow Events is a luxury event planning and design company located in Naples, Florida.Read more

Marco Island Water Sports


Marco Island Water Sports in conjunction with Naples Beach Water Sports offers diverse fun filled experiences on the waters of Marco Island and Naples.Read more

Mid-American Coaches


Mid-American Coaches, a family and veteran owned business, was founded in 1927 and grew from a local regular route operation to the charter and tour motor-coach operation it is today. Read more

Mitch's Cookies


In 2016, Mitch's Cookies developed their first old school drugstore soda fountain shop and Mitch’s Cookies Dessert Bar and Soda Fountain was born!Read more

Molly's Trolleys


Tootle Lou Trolleys, Inc dba Molly's Trolleys is a trolley transportation company that specializes in group events from corporate and convention delegates to family reunions, weddings, festivals and other special events. Our vehicles are elegant, charming, immaculate, and reminiscent of 1920s-style trolleys. Molly’s Trolleys operates trolleys that are Enclosed and Air Conditioned for all of our events. Read more

Montelle Winery


Established in 1970, Montelle's philosophy is to farm our vineyards with a respect for the land and the environment. Read more

Mount Pleasant Estates


With more than 150 years of winemaking excellence, Mount Pleasant Estates is what every Missouri winery aspires to be. Read more

Naples Beach Water Sports


Naples Beach Water Sports provides water adventures at the Ritz Carlton of Naples and Vanderbilt Beach in Naples, FLRead more

Naples Transportation & Tours

HEADQUARTERS|Naples, Florida

NT&T is the leading provider of reliable full-service transportation in Southwest Florida with a fleet of over 80 vehicles and 100 professional and courteous chauffeurs.Read more

Naples Trolley Tours


Join Naples Trolley Tours for a fascinating tour of the Naples area and experience the natural beauty, history, and charm of the city.Read more

NOA International


NOA International manufactures hydraulic tilt and recline wheelchairs which enhance the continuum of patient care,Read more

NOA Medical Industries


NOA Medical Industries is the leader in the development and manufacturing of high quality, fully adjustable, electric and manual high/low bed systems and sleep safety accessories for the long-term care market.Read more

Palm Beach Tours & Transportation


Palm Beach Tours & TransportationRead more

Peregrine Capital

HEADQUARTERS|Chicago, Illinois

Peregrine Capital is a private investment fund that is managed by the principals of Osprey.Read more

Port O Call Marina


Port O Call Marina has all of your water sport activity needs and much more! Boat Rentals, Paddleboards, Kayaks, Bike Rentals, Daytime and Sunset Cruises; Private Charter Cruises; Charter Fishing Excursions, Gift Shop, Snacks and Beverages.Read more



Osprey Meetings & Events is a global meetings and events planner that offers one leadership team from start to finish.Read more

Osprey Sports Franchise

HEADQUARTERS|Geneva, Illinois

Osprey Sports Franchise is the holding company for the partnership interests of the Kane County Cougars, a minor league baseball franchise affiliated with the major league, Arizona Diamondbacks. Read more

Red/Blue Line Insurance

HEADQUARTERS|Wilmette, Illinois

Red Line Insurance and Blue Line Insurance are captive insurance companies incorporated in the state of Missouri.Read more

Regency Water Sports


Operating on Marco Island since 1998 with two beach rental locations, conveniently located on the beach by The Club Regency and Eagles Nest boardwalks on Marco Island, FL.Read more

Retail Dynamics Incorporated

HEADQUARTERS|Chicago, Illinois

Retail Dynamics Incorporated is a venture capital firm providing small business start-ups the necessary capital to grow into a successful enterprise.Read more

Segway of Naples Tours


Segway of NaplesRead more

Stan's Coffee


Stan’s Coffee & Food Service has been serving Florida’s businesses for over 60 years.Read more


HEADQUARTERS|Naples, Florida

Sunmaster strives to furnish and install the best ornamental metal, canvas and storm products in the industry.Read more

Shepler's Ferry

HEADQUARTERS|Mackinac Island

Shepler's offers the fastest ride to Mackinac Island and is the best cruise line for weddings and charters in the Great Lakes.Read more

Tacos & Tequila Cantina


Funky unconventional Tex Mex at its best with popular Americana sprinkled into your favorite south of the border treats. Read more

Texas Bragg Trailers


For over 30 years, Texas Bragg Trails has set the industry standard in trailers with heavy-duty construction, reliable service, and longevity. Read more

Tier Electric


Tier Electric is an electrical contractor providing Commercial, Construction, Remodeling, and Residential Electrician Services for Southwest Florida.Read more

Town and Country Nursery


Town and Country Nursery offers landscaping, hardscaping, landscape maintenance services as well as a large nurseryRead more

Washington Vines

HEADQUARTERS|St. Louis, Missouri

Washington Vines is a premier wine which took life after converting a 70 acre golf course into a fruitful vineyard.Read more

Williams Bay

HEADQUARTERS|Chicago, Illinois

Williams Bay is a private investment firm that delivers superior results to investors and businesses in which we invest.Read more

World Wide Farms


World Wide Farms is the trusted producer of organic and conventional fresh herbs and select leafy greens to many of the nation’s top retailers such as Whole Foods, Kroger, Sysco and meal delivery company Home Chef under the name Meyer Farms.Read more

Ziglin Signs


Founded in 1997, Ziglin Signs has grown into a leader in the sign industry and is the preferred sign manufacturer for national brands like Margaritaville, Chipotle, Denny’s, and Walmart.Read more


HEADQUARTERS|Tacoma, Washington

Chrysalis offers sightseeing boat cruises, scenic tours and private charters in Tacoma, Washington.Read more

La Crosse Queen

HEADQUARTERS|La Crosse, Wisconsin

The La Crosse Queen is a modern-day replica of the grand river boats that plied the Mississippi River in the early 1900s.Read more

The Marco Island Princess

HEADQUARTERS|Marco Island, Florida

The beautiful 90' Marco Island Princess sails daily from her dock at Rose Marina cruising the pristine waterways of Marco Island.Read more

Minneapolis Queen

HEADQUARTERS|Minneapolis, Minnesota

Minneapolis Queen offers sightseeing boat cruises, scenic tours and private charters on Lake Minnetonka and the Mississippi River.Read more

Miss Naples Catamaran


Come sail with us aboard the newest Catamaran in Southwest Florida, Miss Naples. Our 48’ custom built Catamaran can accommodate up to 48 passengers and is your perfect ride to experience the beauty of Naples.Read more

Naples Princess

HEADQUARTERS|Naples, Florida

For Over 25 years, Naples Princess Cruises has been celebrating the breathtaking beauty of southeast Florida as a popular Naples attraction.Read more

Volunteer Princess


he Volunteer Princess is the only modern and luxurious dining cruise vessel on the upper Tennessee River, located in Knoxville, TNRead more

West Star

HEADQUARTERS|Seattle, Washington