1977
Born in Cincinnati, OH
October 22. Son of Joyce and Robert Penebaker.
About Khary
Built from
the Ground Up
From Cincinnati to the national stage. From $0 to $35M in revenue. From personal tragedy to purpose.
The short version
Real story.
No script.
I was born in Cincinnati on October 22, 1977. I was 22 months old when my mother, Joyce, died by firearm suicide. My father raised me in Milwaukee, and that loss became the thing that shaped everything.
In 2002 I started a commercial roofing and sheet metal company out of my garage with nothing, and built it into one of the top five roofing firms in Wisconsin. When the recession hit, it ended in an involuntary Chapter 7 in 2011. I climbed back, learned sheet metal inside out, and went on to help grow another company from about $5 million to $35 million with 180 people, working across EPDM, TPO, GAF products, JM insulation, and the full building envelope.
In 2016 I ran for Congress in Wisconsin's 5th district. I lost, and I learned more about leadership in that campaign than in a decade of business. From 2017 to 2023 I served as DNC Representative for Wisconsin.
Now I am Division President at MetalMaster-RoofMaster, running the Upper Midwest division of a commercial roofing and architectural sheet metal company out of McHenry, Illinois. What I care about has not changed: leadership under pressure, mental health, racial equity, and what resilience actually looks like when it is tested.
I lost my mother to suicide before I could walk. That's not where my story ends. It's where it starts.
$35M+
Revenue built
180+
Employees led
88+
Media features
82K+
Social followers
Career journey
The Journey
Everything is connected. Every job, every loss, every campaign. Here's how it stacks up.
1997
University of Wisconsin-Milwaukee
Studied business. Started building the foundation for everything that came next.
2002
Founded Penebaker Enterprises
Started a commercial roofing and sheet metal company from scratch. EPDM, TPO, GAF products, JM insulation.
2011
Grew to $15M revenue, 50 employees
Nine years of grinding. Took the company from zero to $15M in annual revenue with a team of 50.
2011–2013
Metal-Era
Took a $350K product line to $1.5M in one year. Trained national sales reps across the country.
2014
Joined Roofed Right America
Helped scale the operation to $35M+ revenue and 180 employees. Deep expertise in building envelope, ANSI/SPRI standards, sheet metal.
2016
Ran for Congress (WI-5)
First run for public office. Learned more about leadership in one campaign than in a decade of business.
2017
DNC Representative for Wisconsin
Elected to represent Wisconsin at the Democratic National Committee. Served through 2023.
2018
Grew company to $35M+, 180 employees
Revenue, team, and impact all at their peak. Built something real.
2020
National stage
Speaking at the DNC Convention. 82,000+ followers on social media. Gun violence prevention advocacy reaching millions.
2026
Division President, MetalMaster-RoofMaster
Leading the Upper Midwest division of a commercial roofing and architectural sheet metal company out of McHenry, Illinois. Same playbook as before: build the team, fix the systems, deliver the work.
Core beliefs
What I Stand For
Authenticity
No scripts, no performance. What you see is what happened.
Resilience
Getting knocked down is guaranteed. Getting back up is a choice.
Equity
Real equity work is uncomfortable. That's how you know it's working.
Service
The point of having a platform is using it for people who don't.
Recognition & service
Credentials
Wikipedia Notable Person
DNC Representative 2017-2023
Board President, Planned Parenthood WI C4
Everytown for Gun Safety Fellow
82,600+ Social Media Followers
88+ Media Features
Ran for Congress, WI-5 (2016)
Off the stage
The Rest of the Story
Engaged to Anne. Three kids: Josie, Kyan, and Sydney. Based in Waukesha, Wisconsin. Still figures out parenting one day at a time, same as everyone else.
That is the short version.
Want the whole story?
All of it: the $35M, the campaign, the grief, the rebuild. In my own words.
Or get in touch any time