Middy Matthews · Keynote Speaker

One philosophy, every stage.

Most audiences have been sold to so badly, so often, that they would rather lose a deal than become the thing they hate. Middy's message flips the script, you do not sell, you train. You train your clients on what they are actually deciding. You train your network to understand the value you offer. You train yourself out of the scripts that never sounded like you in the first place.

Over time, the people you trained become the only pipeline you need. It is the same long game that builds athletes, careers measured in decades, not quarters.

The Story

Three decades in the arena.

Middy's athletic life began in her teens with tennis and never slowed down. She competed at the college level, then taught tennis for twelve years, including junior instruction and the summer camps where she first learned that coaching beats commanding.

Today she races competitive mountain bikes, with finishes at 24-hour adventure races, 18-hour mountain bike events, and 200-mile gravel races, many on a tandem. The long arc of that practice, sustained effort, smart recovery, real teammates, is the lived basis of her speaking work.

Inside her professional practice, Middy is a top-producing realtor at Arbor Move Real Estate, working both the Chicago and Ann Arbor markets, where she also trains new agents in their first year. Earlier in her career she worked in advertising and photography, and she has facilitated wellness workshops for healthcare and nonprofit audiences.

"The best coaches don't push you across the finish line. They build the athlete who gets there on her own."

Tennis / Teaching

College competitor, then twelve years as a teaching professional, junior instruction, and summer camps.

Endurance / Racing

24-hour adventure races, 18-hour MTB events, 200-mile gravel, often on a tandem where teamwork is non-negotiable.

Real Estate / Sales

12+ years as a top producer across residential, luxury, and commercial, with a specialty in first-time homebuyers.

Creative / Community

A background in advertising and photography, a sponsor of regional bike races, and a regular in grassroots civic work.

Signature talks.

Four keynotes, one architecture. Each talk is tailored to the room, with timed session flows, workshop add-ons, and takeaways the audience can use Monday morning.

Sales · Real Estate · Entrepreneurs

Trained, Not Sold.

A sales philosophy for people who hate the word "sales"

The flagship keynote. How to stop chasing, convincing, and closing, and start training your clients, your network, and yourself, so the right people find you first. Includes a practical script audit and a five-year view of what a Trained, Not Sold practice produces.

Keynote 45–60 min · Workshop up to 2 hrs

Leadership · Management · Women in Leadership

Coached, Not Bossed.

Lead like the best coach they ever had

What twelve years of teaching tennis and a decade of training new agents reveal about leading people. The difference between managing tasks and coaching humans, and a framework for feedback, standards, and trust that builds teams who perform when you are not in the room.

Keynote 45–90 min · Leadership track sessions

Students · Youth · Student Athletes

Find Your Lane.

A keynote for the next generation

For ninth graders, student athletes, and young leaders. The race is long, and the fastest start does not win it. Lessons from junior tennis camps to 200-mile gravel races on picking your lane, ignoring the noise in the other lanes, and showing up again tomorrow.

Keynote 45–60 min · School assemblies & banquets

Wellness · Healthcare · Corporate Teams

Habits, Not Hacks.

Think like an athlete, last like one

Thirty years of competitive athletics with no off-season for burnout. Sustained effort, smart recovery, and the habits that keep high performers in the game for decades. Honest about scope, this is lived athletic practice, not clinical advice, and audiences trust it because of that.

Keynote 45–60 min · Wellness hours & half-days

Who She Speaks To

Every room, the same standard.

From conference main stages to intimate all-staff gatherings, Middy tailors every session to the room, with honest credential framing and zero recycled content.

Real Estate Conferences Sales Teams & Brokerages Women in Leadership Young Leadership Conventions Schools & Student Athletes Healthcare Professionals Corporate All-Staff Events Credit Unions Hospitality & Front-Line Teams Cycling & Athletic Communities Nonprofits & Civic Groups