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Meet The Cultivate Team

April 19, 2022

4 minread

Cultivate is built by owners, for owners. Entrepreneurism is inherent. At Cultivate, we believe business owners make the best advisors because they have the real-world experience to connect with our community and partner to work through challenging problems in the business. To continue supporting and positively impacting the small business community, we look for skilled experts with unique experiences from all different aspects of small business.

If you’ve ever wanted to know more about the backgrounds of our advisors, here are some of the talented members of our advising team.

Josh Seago | Business Advisor | Chicago, IL

Josh is your average former business banker turned raging craft-brew festival entrepreneur. Before joining Cultivate, he founded Lou Dog Events in 2012, where he spent 8+ years managing and producing a portfolio of festivals throughout the Chicagoland area. Josh believes in the importance of hiring the right people to complement your skillset and he used that mindset to create a unique business that fostered unification of full-time employees + 100’s of neighborhood volunteers to pull off events smoothly. Josh is an effective entrepreneur with a background in strategic management, marketing management, and leadership, and he loves to utilize his experience to help business owners achieve their goals and turn their vision into reality.

Jessica Osborn  | Business Advisor | New Orleans, LA

Jessica first started her career in fashion and, through that medium, launched her business, Privy Label, as a sustainable fashion consultant to boutiques. She effectively worked to connect her clients to US-based manufacturers and helped with their supply chain process to launch their own private clothing lines. She transformed her core business to be an automated online course. After working with a friend to stage a 2-day intense business boot camp to revamp their business’ focus/ processes/ leadership structure, Jessica felt the gravitational pull to work with more small business owners and impact helping others through her vantage point.

“I hope my clients experience the joy of learning how to control their time because time is the most valuable resource we have in this life. Over time my goal is to help clients build the company they have always dreamed of owning and the life they have always wanted to live.”

Jessica Osborn 

TJ Slattery  | Business Advisor | Denver, CO

TJ had a career in sales in the UK before embarking on an MBA program at the University of Denver, which led him to build and launch a Denver-based brewery. Along with a business partner, TJ grew the business over five years. His partner specialized in the brewing aspects, while TJ ran the business side. With extensive experience managing a broad range of departments and a focus on operational efficiency, and profitability, he loves partnering with other owners to support their business growth.

All of our advisors come from different industries with different experiences, but the one thing they have in common is that they’ve all run small businesses. If you or someone you know is a successful entrepreneur, looking to potentially transition to a new chapter where they can be entrepreneurial, but part of a team full of like-minded entrepreneurs, learn more about joining the team.

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