Jessica LaShawn
The Jessica LaShawn Report · Interviews · News · Business EducationUpdated weekly from Chicago
BUSINESS IS PERSONAL.YOU DON'T KNOW WHAT YOU DON'T KNOW.EXPOSURE CHANGES WHAT PEOPLE BELIEVE IS POSSIBLE.GET YOU SOMETHING OF YOUR OWN.THE BLESSING NEEDS SOMEWHERE TO LAND.YOUR STORY IS PART OF THE STRATEGY.BUSINESS IS PERSONAL.YOU DON'T KNOW WHAT YOU DON'T KNOW.EXPOSURE CHANGES WHAT PEOPLE BELIEVE IS POSSIBLE.GET YOU SOMETHING OF YOUR OWN.THE BLESSING NEEDS SOMEWHERE TO LAND.YOUR STORY IS PART OF THE STRATEGY.
On The Couch — Interviews

Pull up a seat and hear it from the people doing the work.

Educators, founders, program directors, and community partners on what the headlines leave out. Long-form conversations, plain language, real receipts.

On The CouchIn Production

What funding season actually decides for kids

With: School district program director

Budget language sounds procedural until you follow it down to one classroom. We talk about what gets cut first and who notices last.

InterviewNow Booking

Building a program that survives its first grant

With: Founder of a youth workforce nonprofit

Most youth programs are built for the pilot year. We talk about designing curriculum, staffing, and outcomes that live past the check.

RoundtableComing Soon

Who is teaching entrepreneurship — and who approved it?

With: Educators, mentors, and small-business owners

Business education is politics with a lesson plan attached. Three seats, one table, and an honest conversation about who sets the curriculum.

InterviewNow Booking

When sponsorship becomes strategy

With: Corporate community-impact lead

The difference between a logo on a banner and a partnership that changes a neighborhood. We get specific about both.

Educational Business Politics

The news, and then the part that affects your program.

Every brief ends the same way: so what does this mean for the work? Then it points to the service that fixes it.

Education Policy

Career and technical education keeps getting rewritten mid-semester.

Every few years the mandate changes names, and schools are asked to deliver entrepreneurship outcomes with last cycle's materials.

So what

If your curriculum is tied to one funding cycle's language, it expires with that cycle. Build it to translate.

Curriculum Design
Workforce & Youth

Youth programs are measured on attendance, not on exposure.

Compliance metrics count bodies in seats. They rarely count whether a young person met somebody doing the work they'd never seen up close.

So what

Design the exposure on purpose, then report it. Funders renew what they can see clearly.

Youth Program Development
Small Business

Procurement and certification rules assume you already have a back office.

The paperwork that unlocks contracts quietly favors businesses with systems, records, and somebody whose job is the follow-up.

So what

Brand clarity and operating systems are eligibility requirements now, not vanity projects.

Business Education
Technology & Access

AI showed up in classrooms and boardrooms before the policy did.

Guidance is still being drafted while organizations are already making decisions about tools, data, and who gets trained on them.

So what

Write your own internal rules now. It is easier than retrofitting them after a mistake.

AI Business Systems
Community Investment

Community dollars are moving toward partnerships with proof.

Sponsorship conversations increasingly start with outcomes, documentation, and storytelling — not with a program description.

So what

Your receipts are your pitch. Build the documentation into the program from day one.

Community Programming
Branding & Trust

Trust is the last competitive advantage nobody can subsidize.

In a crowded market, the mentor-based brand — the one people can vouch for — is the one that gets referred into rooms.

So what

What people say about you when you leave the room is your actual marketing budget.

Mentor Branding
Latest from the Journal

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Jessica LaShawn speaking on a broadcast set about business education and community programmingJessica LaShawn in a mentorship consultation walking a client through their brand strategy
Bring the Conversation to Your Room

Panels, keynotes, podcasts, and press.

I talk about business education, mentorship, youth development, and the politics that decide who gets taught what — in language a room full of people can actually use.

The Newsletter

Come sit by me.

I probably have something to tell you.

New interviews, policy briefs, and stories about business, mentorship, and community — plus the occasional "now ain't that something."

Come sit down.

Read the stories, watch the interviews, then tell me what you're trying to build. We'll start there.