20+ years of being early to things before they were cool.

I’m that person who sees the thing before it has a name. Not because I’m a prophet — I just really can’t stop analyzing the internet. It’s a whole thing. My therapist knows.

I always thought I was an entrepreneur, but that never quite fit. Then I realized I’m a builder. I see a problem, I get annoyed, I make a thing. Rinse and repeat for 20+ years.

No college degree. No roadmap. And when I finally built my own tech company… intentionally bootstrapped, because I’d already lived the VC route and chose differently this time.

The full story is below. But fair warning: it starts in a trailer on dial-up and ends with a software company built entirely on my terms. So buckle up. 🤠  

How I earned a PhD from FIOU *figure it out university* 😜 

1998 | a builder is born

My mom survived domestic violence, and what she showed me was simple: never stop, always fight for yourself. I was a 4.0 student earning college credits while still in high school, a varsity Track & Field athlete, an editor of my school paper…and I was working full-time. The second I turned 18 I moved out, proud as anything to have my own trailer for $325/month. That trailer is where I taught myself to build websites using Microsoft Server extensions and Dreamweaver…over dial-up, while working my way through 10 different roles at the Seven Feathers Truck Stop. Five years later, I hit the glass ceiling as operations manager. I’d already outgrown the ceiling before anyone noticed I was there.

2002 | a seller is born

Working full-time, side-hustling my Tupperware business, and teaching myself to code at night…over dial-up…all at the same time. This is where I learned what it actually feels like to work hard, build a team, change lives, and be recognized for it. That feeling became the fuel for everything that came after.

2007 | an CREATOR is born
(a.k.a. my Associate's Degree)

Then social media happened, and I took to it like a fish to water. I was an early adopter of MySpace…and I didn’t just scroll, I studied every platform so I could help others use them well. I built SKORCH, the first digital magazine for plus-size fashion…hand-coded with flipping pages in ASP because tools like ISSUU didn’t exist yet. I marketed it entirely on MySpace. It hit over 1 million views in its first year and was eventually acquired in 2016. I honed graphic design, advertising, promotions, web design, and I started to understand something brands completely missed: readers didn’t want to see models in the clothes. They wanted to see themselves. And at a size 22+, I wasn’t waiting for the industry to catch up. I just showed up anyway. MTV listed me as a Top 10 on Snapchat…a sentence I never expected to type, but here we are. That chapter? That was basically my Associate’s Degree.

2012 | a producer is born
(a.k.a. Bachelor's Degree)

I took my love of fashion and community and used them to rehabilitate and relaunch Portland Fashion Week®…creating a platform for independent designers and artists who needed one. We filled 30,000 square feet at the Oregon Convention Center, drew over 4,000 attendees over three days, and got covered in ELLE and Glamour with Project Runway and America’s Next Top Model alumni in the building. I produced all of it. I consider this my Bachelor’s Degree.

2014 | a vc-backed cofounder is born
(a.k.a. my Master's Degree)

I co-founded Society+, a digitally native, vertically integrated plus-size fashion brand built on one idea: help women feel confident and own the room. We were VC-backed. I taught myself everything…tech packs for plus-size women, sourcing, wholesale, Shopify, affiliate marketing, influencer management…and we launched tulle skirts and crop tops in sizes 12–32 for under $100 when everyone else was still dressing plus-size women in cold-shoulder florals designed to minimize. The point was to take up space unapologetically. Turns out, joy is a solid business model. Now that was my Master’s Degree.

2015 | a crusader is born

After 10 years of blogging and building in the plus-size fashion space, I posted something that went viral across every major news outlet. The idea was simple: confidence isn’t brave…it’s just confidence. Thirty million people agreed. It was the moment I realized my passion was never really about fashion. It was about women…their confidence in business, in rooms they were told weren’t built for them, in life. I was a crusader. I just finally had a name for it.

This time — no investors, no permission, no diluted vision. Bootstrapped by choice, because I’d already learned what it costs to build on someone else’s terms. And honestly? It’s intentional in a bigger way than that. I look at what’s happening in the market and I see it clearly: the future belongs to the individual entrepreneur. Gig work isn’t a trend — it’s a shift. The tools we’ve all been handed were built for a corporate world that is slowly disappearing, and nobody is building for the people who are actually showing up to replace it. That’s exactly who I built Geniechat for.

Every pixel. Every feature. The app branding, this website, the UI/UX…all designed by me, for you, with intention. Because the strongest businesses run on clear systems AND real relationships. Not one or the other. Both. Together.

At 42, I am happy to announce the birth of my newest baby — Geniechat. 🪄💜

2022 | a tech CEO is born

And then it happened. Lightning struck. After almost two decades of building something from nothing, over and over — learning marketing by jumping into social media and never looking back, never turning down an opportunity, leaning into hard moments because I knew they were teaching me something, never getting a traditional degree but logging 15+ years of the hardest kind of labor — it all culminated in this.

I saw a massive gap: I was teaching thousands of entrepreneurs how to have better systems while my own business was held together with sticky notes and vibes. Notes apps. Screenshots. Pinned DMs. Google Docs that no one…including me…could find. Classic.

So I built Geniechat. Because I needed it.

 

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clippings & awards

KNOW Women 40 Under 40
FORBESWomen Forum
Portland Business Journal – Woman of Influence Award
eTail Visionary Best-In-Class Finalist
Cover of Florida TREP Magazine
GrowFL Top 50 Florida Business to Watch
Top 25 Women Visionaries – Pose Magazine
Women’s History Month – Space Coast Business Magazine 

Interviews

Jessica Kane, CEO & Publisher
Accepts Award for BEST FASHION MAGAZINE

Jessica and her work has been featured in