Trusted by Top Venues, Praised by Clients

Chicago Venues

  • Medinah Country Club

  • RPM Events

  • River Roast

  • London House Chicago

  • Merchandise Mart

  • InterContinental Magnificent Mile

  • Sheraton Grand Chicago Riverwalk

  • Swissotel

  • Chicago Winery

  • 90th Meridian

  • McCormick Place

  • Hyatt Regency

  • Chicago Illuminating Company

  • VU Rooftop

  • Four Seasons Hotel Chicago

  • Soldier Field

  • The Salt Shed

  • Ambassador Gold Cost

  • The Honeycomb (People’s Gas Pavillion)

  • Wicker Park Inn

  • Ovation Chicago

  • Colvin House

  • La Grange Country Club

  • The Westin Chicago Lombard

  • Cantigny Park

  • The Easton Downers Grove

  • The Morton Arboretum

  • Lake Barrington Shores & Recreation Area

  • Geneva Commons

Destination Venues

  • Arlene’s Grocery (New York, New York)

  • Cobra Nashville (Nashville, TN)

  • Spirit (Pittsburgh, PA)

  • Harmony Hill Vineyards (Cincinnati, OH)

  • Minocqua Country Club (Minocqua, WI)

  • GATHER at Deer District (Milwaukee, WI)

  • Baird Center (Milwaukee, WI)

  • The Delafield Hotel (Delafield, WI)

  • The Boardwalk (Benton Harbor, MI)

  • The Cheney Place (Grand Rapids, MI)

  • Revival Wedding Barn (Dowagiac, MI)

  • Fountain Square (Cincinnati, OH)

  • Twin Lakes Country Cabins & Wedding Venue (Derby, IN)

  • Evangeline’s Bistro & Music (St. Louis, MO)

Past Venue Map

 
A man with a beard and curly hair plays an acoustic guitar and sings into a microphone, standing near a window with a cityscape of tall buildings behind him.

Past Corporate Clients

Stylized depiction of a bear's head with its mouth open, using orange and black colors.
A logo for the PGA TOUR featuring a white silhouette of a golfer swinging a club on a blue background with the words "PGA" and "TOUR" in bold red and white letters.
Milwaukee logo in red with a stylized lightning bolt underneath.
Paycom logo with a green abstract symbol and black text
Logo of VENTAS, featuring a stylized letter 'A' in blue with a black accent at the bottom, followed by the company name in black capital letters.
Money Live North America logo featuring a stylized M and a geometric design
University of Illinois Urbana-Champaign logo with an orange block I and navy blue text.
Close-up of thin crust pepperoni pizza on a white plate, with melted cheese and pepperoni slices.
Logo of Fresenius Kabi featuring blue wavy lines and the company's name in blue letters.
Willis Tower logo in black text
ND Paper logo with red circle containing yellow 'ND' and green text 'ND PAPER'.
Logo of Warren-Newport Public Library, featuring stylized illustration of a building, with abbreviation "wnp" in large colorful letters.
Noah Medical logo with circular graphic of purple and blue dots and the company name in black text.
Netrix Global logo with purple and gray stylized 'N' and bold black text.
A black and white logo with the initials 'DSI' in tall, narrow letters.
Suddath logo with blue and yellow colors and stylized emblem
HYATT logo in blue with a stylized arch underneath
Logo of Lagunitas Brewing Company featuring a dog's face above the company name, with a red ink splatter on the right.
A stylized highway route shield with the text 'FIFTY WEST' at the top, the number '50' in the center, and a letter 'W' on the right.
A black octopus tentacle forming the letter 'O' above the word 'OCTOPI' with the same tentacle curled into the letter 'O', all in black silhouette on a white background.
Green background with gold and white text promoting Guinness Open Gate Brewery's St. Patrick's Day VIP event at OGB from March 13 to 17, featuring shamrock graphics and a harp logo.
Community Transportation Network logo with red and black text and a stylized speech bubble.
The word 'Steelcase' in large black letters on a white background.
Logo of CB1 Capital with blue and black text on a white background.
The logo of Janko Hospitality with text in blue and black.
Benzinga logo in dark blue text on a white background.
Distalmotion logo with a stylized wave and arrow icon in a blue square, and the company name in blue text.
A logo with a large tree and the words 'thrive WEALTH MANAGEMENT' underneath
Illustration of a plant with roots, leaves, and flowers, and the text 'JUST ROOTS' at the bottom.
Holland logo with a star and the text 'Holland Built on Integrity'
Coveatus logo with the word 'covetous' in dark blue lowercase letters and a geometric design of interlocked squares in red, dark blue, and teal.
Logo with the text 'The Salt Shed' in blue, stylized font on a black background.
Logo of Conquest Racing with stylized swoosh design.
Blue background with white text reading 'charles SCHWAB'
TD Synnex logo featuring a stylized wave icon and the company name in teal and black text.
NETJETS logo on a dark background
Blue cloud with the word 'salesforce' in white text.
Liverpool Football Club logo with the phrase 'You'll Never Walk Alone' at the top and 'EST 1892' at the bottom.

Past Events

NETJETS logo on a dark background.
Stylized logo for PGA Tour featuring a golfer swinging a club, with text "PGA TOUR" in blue, red, and white colors.
Man with a beard playing an electric guitar poses next to a sign at the Presidents Cup golf tournament, surrounded by yellow flowers and white hydrangeas, in an outdoor setting with large trees and event structures in the background.

Providing ambiance for NetJets and the PGA Tour at the 2026 President’s Cup at Medinah Country Club

Ryan at the iconic Soldier Field performing at an event for the Chicago Bears

Graphic illustration of a bear's head with open mouth, in orange and black colors.
Man standing inside a stadium holding a guitar case, with empty seats and a field in the background.

Ryan with Matthew Lewis (Neville Longbottom, Harry Potter series) at Soldier Field performing for 3,500 people for Liverpool FC and Leeds United.

The Liverpool Football Club crest featuring a red Liverbird, with the motto "You'll Never Walk Alone," established in 1892.
Two men smiling and standing close together outdoors. One man is wearing a black t-shirt, beige pants, and a cap with gold writing. The second man is wearing a yellow sports jersey with black and white trim, black shorts, a watch, and a cap. There are people and trees in the background, and cloudy skies overhead.
A man with a beard and curly hair tied in a bun wearing a gray jacket and blue shirt playing an electric guitar. He is standing in front of a white wall with soft lighting and is near a microphone with a stand.

Performing live for guests of Charles Schwab in Chicago, IL

Charles Schwab logo with blue background and white text
A man with a beard and curly hair tied back, smiling while playing an acoustic guitar outdoors. He is wearing a cream-colored shirt and black pants, with a strap over his shoulder. There is a microphone in front of him and greenery in the background.

Yearly performance for Chicago Non-Profit “Just Roots Chicago”

Illustration of a tree with various plants and roots, with the text "Just Roots" underneath.

Solo acoustic performance for the C-Suite at Ventas, Inc. on the coast of Lake Michigan

Logo with a stylized letter A in blue and black and the word VENTAS in black uppercase letters.
A man standing on grass near a body of water holding an acoustic guitar, with a cloudy sky overhead and green plants along the shoreline, and benches in the background.

The Ryan Shephard Trio performs on a live broadcast for MeTV’s show “Toon In With Me”

MeTV logo with black and white text on a yellow background.
A band with three members performing on a colorful stage decorated with bright props and a sign that reads 'ToonY Bash'. The band includes a man playing a pink electric guitar, a man playing drums, and a man with a bass guitar, all smiling and facing the camera. There is a disco ball hanging from the ceiling and stage lighting above.

Interested in booking an event? Fill out the form below to set up a conversation and receive a custom quote!

Solo performances starting at $2,000

Tisdale Shephard Duo starting at $2,500

3-4 piece band starting at $3,500