Teamwork & whatnot.

A woman with long, wavy dark brown hair smiling, wearing a mint green top with lace and embroidery, and the name 'Andrea' at the bottom.
A woman with long, wavy dark hair with light brown highlights, smiling and winking while wearing a teal leather jacket. The background is light gray, and the name "JESSIE" is written in white capital letters at the bottom of the image.
Professional headshot of a smiling man with dark hair, wearing a blue and red checkered shirt, against a plain white background, with the name 'Steve' in white text at the bottom.
Headshot of a young man with dark, textured hair and a beard, wearing a black floral shirt, smiling slightly, with his left arm partially visible showing a tattoo.

  • Founder

    Andrea is equal parts workhorse and class clown. Nobody laughs harder than her and nobody is more dedicated to getting the job done right.

    Professionally, Andrea worked in the beauty industry for over 20 years, including co-owning a successful hair and makeup services company, Flawless Beauty Chicago, with good friend and colleague, Christina Purtell. Andrea also worked for years on photo shoot sets, perfecting the art of wardrobe styling and photo directing.

    Andrea started her messaging and marketing business several years ago and owes her success to her proprietary “IT Factor” and “Power of 3’s” strategies, both of which she developed to help her clients achieve their business goals in the most authentic and effective way possible.

    Andrea is the co-host of the top rated, How Not to Suck At Divorce podcast with attorney Morgan Stogsdill and an editor for Uploader Magazine, where she writes about divorce and discovering your IT Factor.

    She has been featured on local and national TV shows, as well as in TODAY Parents, Uploader Magazine, Voyage Chicago, and Chicago North Shore Moms.

    You can follow her shenanigans on Instagram @theandrearappaport

    Andrea’s IT Factor:
    Her candor, wit, and wisdom. Her ability to take miscellaneous information and turn it into effective messaging that drives revenue. Her creative mind is coupled with her logic and heart. She makes clients instantly feel comfortable and supported.

  • Photographer

    Jessie has been a professional photographer for over a decade, and started her wildly successful business, Jessie Hearn Photography, six years ago.

    Jessie is regarded as one of the top family photographers in the Chicago area and it’s no secret why. She instantly creates environments where clients feel most like themselves, and is ready to capture every authentic smile, laugh, and thoughtful expression. She lights up any room she's in, with her infectious personality and quick wit. She’s never met a stranger, so even the “buttoned up” corporate clients will be chatting with Jessie as if they were summer camp bunkmates.

    She’ll have you smiling, whether you planned on it or not.

    Jessie and Andrea work seamlessly together, truly, the dynamic duo.

    Jessie’s IT Factor:
    Her ability to make eyes twinkle and make even the most uncomfortable clients comfortable in front of the camera.

  • Interview and Resume Coach

    Steve is an award-winning salesman with over 30 years of experience. His success is attributed to his top notch communication skills and his unique ability to authentically connect with clients. He uses these same skills with his interview coaching.

    Steve has the magic touch when it comes to effective communication. His clients are amazed at how quickly he can hone in on their strengths and offer them key strategies on how to stand out amongst the competition. He delivers information in such a way that feels like you’re having a drink with a friend, a friend who’s about to help you land your dream job.

    When Steve isn’t working with clients or crushing sales’ goals, he’s playing keyboard in some of Chicago’s most awesome cover bands.

    Steve’s IT Factor:
    He’ll make you feel instantly comfortable and he’s as wise as he is charming. But sorry, ladies, he’s taken.

  • Videographer

    Robert is a one of a kind videographer and editor. His extensive knowledge in the field, enables him to work quickly and effectively. He’s creative and pays close attention to detail.

    Robert has been producing professional videos since 2010 and He is the senior editor for the 2nd highest rated divorce podcast on Apple Podcasts.

    Robert works closely with Andrea to produce website videos, industrials, and social media videos for our IT Factor clients.

    Andrea jokes that although Robert has an affinity for Horror films, he is far from a nightmare to work with.

    Robert’s IT Factor:
    His calm demeanor. Even the most nervous clients are immediately comfortable in his presence.