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fearlyss media

Overview

Fearlyss Media is a full-service social media agency. We are experts at crafting a strategy that brings your content to life and connects you with your ideal customer. We take the guesswork out of social media marketing so you can focus on your business. We have fun and forge lasting relationships which shine through everything we do. We are intentional, strategic and FEARLYSS. Fearlyss Media offers the following: 

Designed for busy business owners and executives who understand the
power of a strong social media presence but lack the time or expertise to perfect it.

Aligning your business goals, value and story to create an effective online presence.

Critical for brands to connect with their audience and stay competitive in the digital age.

Helping businesses harness the power of social platforms to achieve their goals.

Supporting businesses in all aspects of their marketing and sales funnel.

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Meet Our Team

Alyssa Olerud

Alyssa Olerud

Founder & CEO
Social media and personal branding for business owners and professionals | Trained 500+ on authentically selling online

FOUNDER & CEO

Alyssa Olerud

Alyssa Olerud is the Founder and CEO of Fearlyss Media, where she empowers business owners and professionals to share their stories and connect with their audiences on social media.

Before diving into entrepreneurship, Alyssa pioneered a remote program for a nationwide sales team, teaching them to leverage social media to expand their territories. Results boasting a 24% increase in success metrics and since then, she’s trained hundreds of sales reps on how to best utilize social media and works with business owners to manage their social media presences.

She lives by the philosophy that social media doesn’t need to be complicated; rather, it’s a powerful tool for finding your next best client. And if anyone knows a thing or two about balancing complexity, it’s her — juggling the chaos of raising two toddlers while fearlessly navigating the business world.

Alyssa is a New York native who now calls North Carolina home. She’s an avid reader, a die-hard sports fan who started her career working for the New York Yankees and Philadelphia Phillies, and someone who’s never shied away from dreaming big.

Josh Olerud

Josh Olerud

Growth Advisor
With over 18 years of experience in sports business leadership roles, Josh Olerud is a seasoned executive adept at driving strategic growth initiatives, business development, operations management, sales, and marketing. He currently serves as the Advisor for Strategic Growth here at Fearlyss Media, where he partners with the team to develop and implement strategies to propel the company's expansion. Josh is the Senior Manager of Business Development at Tar Heel Sports Properties, where he creates strategic partnerships that tie together the community and Tar Heel athletics. Josh's extensive experience also includes successful tenures as the President and Chief Operating Officer of the Scranton/Wilkes-Barre RailRiders baseball team from 2015 to 2019. Before that, he spent five years as the Executive Vice President and General Manager of the Potomac Nationals, managing day-to-day operations, sales, marketing, and staff leadership.
Austin Dempers

Austin Dempers

Community Manager
With over 10 years of leadership experience in mission-driven organizations and non-profits, Austin has cultivated a deep understanding of customer-focused communication and community engagement. Starting her own event business and transitioning it to a brick-and-mortar, she learned firsthand the unique experiences that small business owners face. Austin thrives in communication and community building, working with business owners who have a mission at their core. With years of personal and professional experience in brand building, she knows the importance of keeping passion alive and understands the value of outsourcing when necessary to maintain momentum. Her ability to craft engaging narratives and foster connections makes her an asset in social media management, helping businesses grow their online presence while staying true to their mission. Austin grew up in Michigan and lived in Denver for 12 years before moving to North Carolina. During her down time you can find Austin hiking with her dog and soaking up as much of the outdoors as possible and also finding a way to spend time with other animals that could use a little extra love.
Madison Scholl

Madison Scholl

Community Manager
Hey! I'm Madison Scholl. I am originally from Myrtle Beach, SC but currently located in Durham, NC. I attended the University of South Carolina where my love for videography and photography flourished. At South Carolina, I worked as an intern with the Creative Media Department where I learned the ins and outs of sports media. My sports career has brought me to some notable places including Texas A&M, The Big 12 Conference, NCAA Championships, and The University of North Carolina. These days you can find me freelancing for a variety of projects from graduation portraits to sporting events. In my free time, I love to spend time with friends and family or craft. I love being creative and having multiple outlets to do so.
Lauren Jacaruso

Lauren Jacaruso

Director of Brand Strategy
Lauren graduated from Emerson College in 2013 where she was a Division III Collegiate Softball player. She earned her degree in Marketing Communications and a minor in Business Studies, both with a specialization in entertainment. In 2021, she earned an MBA in Data Analytics from Louisiana State University - Shreveport. Lauren is an innovative marketing professional that has accrued ten years of experience working with national brands and athletes. Eight of those years took place within the professional baseball industry.