#82: Brandee Gaar breaks down how she built a leading Orlando planning firm, survived the COVID zero-events era, and accidentally launched Wedding Pro CEO via daily 10-minute lives and a Clubhouse “morning show.” We talk about the years that looked “successful” but paid nothing, the summers that almost sunk them, her husband quitting (twice going back to serve to keep lights on), and why their standing Friday money/ops meeting is non-negotiable.
We also hit mom guilt, kids who truly don’t remember the games you sobbed over missing, homeschooling for ambition, and the underrated power of a partner who says, “I’m not going anywhere.”
Hit play if: you’re a wedding pro, a parent, or a builder stuck in the middle.
FIND WHAT YOU NEED FROM THIS EPISODE:
00:00 — Meet Brandee Gaar and how she accidentally built a family business
00:48 — From wedding planner to CEO: 18 years of building Blush in Orlando
02:45 — Going live every day (when no one was watching) and why consistency mattered
04:08 — The Clubhouse “Morning Show” that sparked her coaching career
06:30 — Rebranding from She Who Dares to Wedding Pro CEO — and why the shift changed everything
07:40 — How Gary Vee and a pandemic turned her into an educator (against her plans)
09:50 — The early coaching days: Zoom calls from an RV and building the first offers
11:20 — When “successful” still meant broke — learning the hard way about profit and salary
13:05 — Finding purpose in her 40s and the late-bloomer advantage
15:30 — The reality of scaling a business with three kids and nonstop mom guilt
19:00 — When her husband quit his job to join the business (and how they made it work)
22:20 — The broke summers that taught her how to actually run a profitable company
24:30 — Why she only coaches “middlepreneurs” — the business owners stuck between hustle and sustainability
27:00 — Lifestyle business vs. legacy business: knowing what you’re really building
28:50 — The motherhood guilt spiral (and what your kids actually remember)
31:40 — Building now so you can be fully present later in life
33:10 — The perks and tradeoffs of both parents working from home
34:55 — Raising kids who see what real partnership looks like
36:50 — Boundaries, roles, and how to stay married while running a business together
42:00 — Conflict, communication, and believing the best in your partner
46:10 — What a modern “family business” really looks like (spoiler: messy but worth it)
50:20 — How to connect with Brandee and her team at Wedding Pro CEO
CONNECT WITH BRANDEE:
LET’S STAY CONNECTED:
Is video more your thing? Watch this episode on YouTube.
Join 1k others in my weekly unhinged newsletter where I get honest about entrepreneurship.
Learn more about the Ironically Serious podcast at www.ironicallyserious.com
Submit a guest or topic for the podcast here.
Follow the podcast on Instagram @ironicallyseriouspod
Stay connected with me @tay.hedden @chanelandlee
Submit your SOS to be featured on an episode here.
Leave me a voicemail here.
Be the first to comment