An animated gif of the core members of the squad

Meet our unfair advantage —
a squad of investors and creators
from diverse backgrounds and experiences.

Jeff Cantalupo

Founder, Managing Partner

Jeff began his career helping large brands innovate while at Leo Burnett. He now helps innovators create brands. Over the course of Listen, Jeff has invested in 20+ startups; providing brand and business strategy for consumer-focused companies in a variety of industries. Jeff is active in the Chicago entrepreneurial community through talks and podcasts, and is a Lecturer at Kellogg School of Management teaching Brand Strategy.

Kimmie Carey


Kimmie is constantly searching for brands that offer better for you products and reimagine customer experiences across every consumer vertical. She learned the ropes of startup investing at Silicon Valley Bank and Morgan Stanley. While an MBA student at Kellogg, she wore multiple hats in the entrepreneurial world, from founder to operator (Rothy’s) to investor (Techstars, Listen), and ultimately discovered her passion for identifying high-potential brands and partnering with entrepreneurs to develop creative strategies for growth

Joelle Cosmas

Head of Brand Platform

Head of all things brand and content at Listen, Joelle has spent her career developing creative campaigns and strategic marketing plans for worldwide and local brands. Before joining Listen, Jo sunk her teeth into business leadership at Leo Burnett, leading account efforts for brands like Phillip Morris, Beef It’s What’s For Dinner, Whitewave and TJX Companies. With a passion for curation, Jo is always looking for the next big thing to amplify our portfolio companies.

Rick Desai

Managing Partner, Head of Investments

Rick leads Listen’s investment team. In 2009, he co-founded Chicago startup studio Dashfire that built and invested in 40+ companies. He was awarded a Clinton Fellowship in 2008, supporting social enterprise in urban Indian slums. A graduate of Georgetown University, he was previously an investor at Madison Dearborn Partners. Rick is a Lecturer at Kellogg School of Management teaching Entrepreneurship, Digital Marketing and was awarded a Faculty Impact award in 2018.

Brentos Fernandez

Head of Creative

Part creative problem-solver, part brand whisperer, Brentos has spent his career creating content-driven campaigns for consumer brands. He led brand and campaign development as Creative Director at Leo Burnett, Barkley and DDB advertising agencies. While at Listen, Brentos developed our brand process, helping entrepreneurs apply a brand lens to all aspects of their businesses.

Hylton Irons


Hylton is always daydreaming about the future and what the world will be like in (insert literally any year). He built his skills analyzing the drivers that make a great business through his time managing IPOs, M&A transitions, and strategic alternatives in Equity Capital Markets at Morgan Stanley as well as Healthcare Investment Banking at Goldman Sachs in New York. During his years at Brown University, majored in Economics, was involved in “Black in Business at Brown” and Alpha Phi Alpha Fraternity, Inc and studied abroad in Granada, Spain. Hylton is our go-to guy for testing out new products and knowing the latest on the vegetarian food scene.

Nika Longo

Brand Platform Manager

Known to roll up her sleeves, Nika is the player you want on your team. Prior to joining Listen, she learned the ins and outs of building brands at DDB/We Are Unlimited and Energy BBDO where she led large-scale advertising campaigns. Nika’s can-do attitude solved business challenges for brands such as McDonald’s, Cape Line, and Jack Daniel’s. At Listen, Nika is your go-to for content and activation tactics as she helps to build the brands of tomorrow.

Ryan Sievert

Head of Design

From user-centered design to identity systems, Ryan has led design in a variety of industries. Steeped in digital, he has built brand experiences for a diverse range of creative companies including innovation agency IDEO, visual communication firm Someoddpilot and ad agencies Leo Burnett, DDB, and FCB. Before Listen, Ryan worked at startups Uptake, TrunkClub and most recently as Head of Design at RISE Sleep Science.

Shawn Dennis

Venture Partner

Shawn joins the Listen team as a Venture Partner as we raise our third fund. Shawn has an incredible history of business and operational leadership to drive sustainable, profitable, and scalable business growth for major consumer brands. She’s spent her career at GoldieBlox, DreamWorks Animation, Mattel, Dell and the NFL. Shawn sits on the board for many companies, including Slumberkins.

Mike Apostal

Venture Partner

Mike has a proven track record as a successful entrepreneur that makes him an incredible Venture Partner for Listen. As the Co-Founder and CEO of Factor, he has built a rapidly-growing, nationally recognized brand that was acquired by HelloFresh in November 2020. Mike was recently named an Entrepreneur Of The Year® 2021 Midwest Award finalist. With an impressive history of investing in and advising food and beverage brands prior to his time at Factor, Mike’s operations expertise is sure to bring 1000% to the Listen team.

Kofi Amoo-Gottfried

Venture Partner

When you’re building a consumer-focused brand, Kofi is the man to turn to for marketing magic. Kofi is the VP of Marketing at Doordash and a consumer marketing professional that is joining Listen as a Venture Partner. Named one of Ad Age’s “40 under 40” young marketing stars in 2014, he has led significant campaigns for Facebook, Nike, and Bacardi Global Brands.