Gen Z Entrepreneurs On The Rise

My generation, Gen X, was the “latchkey generation.” We walked home from school and let ourselves in the house. We turned on MTV and then turned into “Couch Potatoes.” We were born between 1965 and 1980-ish. We grew up with parachute pants, Members Only jackets, and really, really, really great music.
We then got married and had Millenial and Gen Z babies. We walked them to the bus stop, handed them a phone or tablet to pacify them, and dressed them in flannel shirts and leggings. Musically, they listen to literally every genre of music… sometimes 80s pop.
Every generation has its differences and similarities, but Gen X and Gen Z are miles apart in one respect. Only 29% of Gen Xers took the entrepreneurial route. 60% of Gen Z plans to start a business and that’s the highest number ever polled in a generation. Gen X is statistically only half of a generation population-wise, which means folks my age who are business owners are few and far between.
And lately it seems the ages of business owners I meet are increasingly younger.
This week I met a 12-year-old Girl Scout who sold me some cookies. I didn’t catch her name, so I’ll call her Emily (the most popular girl’s name for Z, btw). Emily was smiling and confident as I approached the table in front of Kroger.
“I need a box of Thin Mints…for a friend,” I said. “Yes sir. But don’t you need some cookies for yourself?” Emily replied. It was the best upsell I’ve ever had. Emily had me hooked. I bought 4 boxes. The 12-year-old said she was going to open her own bakery one day. Wow.
On Wednesday I met a 19-year-old recent high school grad who started his own car detailing service. I hired him to make my Jeep sparkle. Wesley has a mobile detail service called Pristine Finish Pros that officially opened in January. He was kind, courteous, helpful, and did a great job.
I found the Girl Scout Cookie sale on Facebook. Wesley is running ads through Instagram. They both got this customer through targeted ads on my social media. I guess the algorithms told them I’m a fat guy with a dirty Jeep. #truth
For Gen Z the digital world is the world they were born into. They’ve already mastered the art of advertising on social media. To the next generation, I would say congrats and “go for it.” Do not let your fears hold you back from achieving great success as business owners.
MONDAY:
ST. PADDY’S DAY
After all of the shenanigans from St. Paddy’s Day weekend, the team signed on to our Monday Morning Meeting alive, awake, alert, and enthusiastic — most of us even wore green! If we had pics, I’d prove it. But we don’t, so you’ll just have to take my word for it. Senior Copywriting Manager Derek Fair and I scheduled a meeting at Rosie Connelly’s at 3 p.m. Monday. The meeting lasted 4 hours and was very productive. (Question: can I expense the bar tab?)
TUESDAY:
MNI @ M+M
This week’s edition of Team Tuesday was even bigger and better than the last two. We sat down with our partners at MNI to talk shop—discussing client updates, business goals, and how their capabilities can help us level up. One big takeaway? With MNI in our corner, we’ve got some of the most advanced targeting tools at our fingertips, allowing us to reach the right audiences both digitally and in the wild. Their cutting-edge tech keeps us ahead of the curve, ensuring our clients’ messages land exactly where they need to. That, and lunch from Little Mexico is always a crowd-pleaser. Big things ahead!

WEDNESDAY:
MOLLY W.’S BIRTHDAY/SEVEN YEARS WITH CARISSA
Wednesday was a HUGE day for celebrations at Madison+Main. Put on your party hats and join us in celebrating the birthday of our beloved President, Molly Whitfield, AND the seventh anniversary of Creative Director Carissa Ghaffari joining the Madison+Main crew. These women are two of the smartest, most capable women I’ve had the pleasure of knowing, and they deserve to be celebrated every day. From the bottom of the hearts of everyone at M+M, thank you for everything you both do!


THURSDAY:
ON THE PANEL
On Thursday morning I had a lot of work to do before noon. I’ve entered five March Madness Brackets. (1 for fun, 2 for fund$ and 2 for charity). After studiously entering my picks into ESPN, CBS Sports, and X, I raced over to University of Richmond for the Virginia Council of CEOs March Luncheon.
I was honored to sit next to Eddie O’Leary (Co-Lab), Ilsa Loeser (Letter Press Communications), TJ Ronayne (Gropen) and moderator Bryant Harrison (7th Wall). We each shared stories about what it’s like to replace yourself with a CEO. I had glowing things to say about M+M Chief Molly Whitfield.

FRIDAY:
NEW CLIENT(S) ANNOUNCEMENT
We are thrilled to welcome two new clients to the Madison+Main family! Sweetie Boy Transportation, a nationwide vehicle transport company specializing in safe, reliable, and hassle-free car shipping for dealers and consumers based in Richmond. And McCormick Hill Farms is a historic, family-owned pasture-to-plate farm in Somerset, Virginia that provides high-quality beef with no hormones or antibiotics.
We began work this week on brand vision, marketing strategy, and of course, and met their office dog, Hannah. #whatasweetie
Be on the lookout for some bada$$ new billboards and other sweet things coming your way.

A FEW OF OUR FAVORITE EVENTS
Richmond SPCA Dog Jog, 5K, and Block Party
Saturday, March 22 | 10:00 a.m. to 5:00 p.m.
Location: 2519 Hermitage Road, Richmond, VA 23220
Join thousands of animal lovers for the 23rd Annual Dog Jog, 5K, and Block Party, presented by our friends at Holiday Barn Pet Resorts and benefiting the Richmond SPCA! Participate in person or select the “run anywhere” option. RVA’s favorite family- and pet-friendly event is Back!
Expect a day packed with fun activities for the whole family. Your participation makes a lifesaving difference to pets in need. All net proceeds aid the Richmond SPCA’s efforts to rescue and rehabilitate homeless animals and to deliver crucial programs to pets and the people who love them.
“Things are goin’ great and they’re only gettin’ better. I’m doin’ all right. Gettin’ good grades. The future’s so bright I gotta wear shades.” – Timbuk 3, 1986