A woman wearing a white tweed jacket and shorts, posing with a slight smile, against a light background.

Founder, Kaylan Boss

Writer, Editor, Entrepreneur — Kaylan Boss’ motto is living, working & traveling well.

From an early age, Kaylan has had an immense interest in content creation, writing, and photography/videography. After visiting Southern California in 2011 & 2012, she became inspired to blog about culture, wellness, lifestyle/home, and beauty.

Her platform began in 2014, after winning Miss Jr. Teen Tampa, with her twin sister Kat. When asked to describe herself in one word, she responded with ‘visionary,’ because she ‘believed in envisioning in the future, and creating a reality that [she] was passionate about.”

After her pageant win, she began to develop her brand, an online boutique, and a series of conferences honing in on self-confidence and self-love.

In 2016 she launched The Visionary Boss, an online publication to share wellness and lifestyle-focused blogs, her thoughts on self-development & the lessons learned from navigating college, entrepreneurship, career, friendships, and relationships. The Visionary Boss has evolved into a platform featuring candid interviews with today’s business owners & influential individuals with impact, and a blog destination for elevated food, drink & travel recommendations.

After working in the wellness space as a marketing & event coordinator, Kaylan started to help support and produce live activations and special events, In 2017, Kaylan along with her sister launched a pop-up event company, Suburb Pop to bring experiential & immersive shopping, retail, art, and culinary experiences to venues/event spaces in Tampa, and give brand visibility to BIPOC small business owners.

Currently, Kaylan lives in Tampa, Florida with her Yorkie named Cashew. Last year, she graduated with her Master’s in Business Administration. In her free time, she enjoys practicing her guitar, attending wellness & yoga classes, cooking at home, and capturing food photography.

The Visionary Boss Story

2011

Kaylan discovers BlogSpot, through her digital marketing class, and creates a blog about fashion trends, wellness, and beauty. The same year she visits Southern California, and falls in love with Beverly Hills’ idyllic luxury hotels, palm trees, lush views, and shops. This trip prompts her to write glossy, sun-drenched stories about the young, affluent & aspiring, and create a mock reality show/video blog called “SoCal.”

2012

The summer before entering high school, Kaylan makes another trip to California, and spends her break soaking up Cali sun, Tumblr re-blogging, journaling, and listening to lots of indie & alternative music. The idea of starting an online platform to share all of her interests is planted.

2013

Kaylan is invited to interview for The 2014 Miss Jr. Teen Tampa pageant. After a successful preliminary interview, she spends two months perfecting her pageant walk, attending pageant bootcamp, workshops, and creating a self-brand.

2014

During the second round of the pageant, Kaylan is asked to describe herself in one word. She responds with “I’m a visionary, because I believe in envisioning in the future, and creating a reality that I’m passionate about.” Kaylan is crowned first runner-up for the Miss Jr. Teen Tampa, and her twin sister Kat wins first place.

Shortly after the pageant win, Kaylan begins to develop a self-brand, and hosts a conference discussing self-confidence and self-love.

2015

The summer before her senior year in high school, Kaylan finds an interest in cinematography, filmmaking, screenwriting, and video editing. She starts documenting her journey of creating her brand “The Visionary Boss.” She spends her weekends learning about boutique merchandising, website design, and product photography.

2016

Kaylan spends six months building a website, creating an online jewelry & sunglasses line, and writing blog posts. Kaylan officially launches the TheVisionaryBoss.com a digital space for wellness and lifestyle posts, journal entries about mental health & self-love, candid think pieces (discussing entrepreneurship friendships, & relationships, & college), and interviews, featuring business owners, artists, athletes, and influential individuals with impact.

The Visionary Boss Shop has its first sale.

The Visionary Boss hits 10,000 views.

2017

The Visionary Boss Shop pops up at the release party of Kat’s book, Girl, Who Hurt You?

2018

Kaylan and Kat debut Suburb Pop, a pop-up event company bringing experiential and immersive shopping & retail, art, and culinary experiences to venues and event spaces in Tampa.

The first event generates local buzz, social media engagement, and encourages small business shopping, and brand visibility for BIPOC business owners.

2020

Kaylan guest-hosts Kat’s talkshow, The Girl, Who Hurt You? Talk Show, where she discusses the importance of self-love, self-care, and healing.

2021

Kaylan takes the stage at Tampa's Unlock Your Future Conference, and talks about the journey of self-funding and independently starting a brand, entrepreneurship, The Visionary Boss, and Suburb Pop.

Kaylan graduates from the University of South Florida with a B.A. in communication and business analytics & information systems, and begins are a career in business.