Description

In this episode of The Wisdom, Lifestyle, Money Show, host Scott Dillingham interviews Sean Lippert, a serial entrepreneur from Windsor, Ontario, known for ventures like surprise weddings, nightclubs, hot body contests, nail salons, coaching the University of Windsor's volleyball team, running Canada's largest volleyball league (WAMBL since 1976), and operating Scarehouse Windsor—a top haunted attraction. Sean shares his mindset: taking risks, learning from failures, and falling in love with the process, starting from selling chips in grade school and DJing at 16. He recounts viral success with his wife's surprise wedding (millions of YouTube views, TV appearances on Ricky Lake/Rachael Ray, Sports Illustrated feature) and pivoting businesses amid challenges like border changes affecting American patrons.

The spotlight is on Scarehouse Windsor: 13 years of scares with annual tweaks (20% revamp cycle), now featuring immersive dinner experiences (e.g., Cabin in the Woods for 16 people, Mad Hatters, Cursed Dinner for 10)—blending horror themes with meals, expanding from a 2020 trial to 30+ sessions, quadrupling in 2025 amid Windsor's event recovery (post-COVID capacity limits easing, per local trends). Sean emphasizes hustle, family influence (blue-collar roots building thick skin), and no-fear failure (e.g., early Scare House losses turned profits). In 2025's Windsor scene (CMHC forecasts stable tourism/growth), this episode motivates aspiring entrepreneurs with actionable advice on innovation (e.g., bylaws for haunts) and community impact (WAMBL's 45+ years). Perfect for Canadians seeking inspiration in business pivots, event planning, or Windsor's haunted entertainment amid 2025's BoC-driven affordability boosts.

Guest Bio
Sean Lippert is a Windsor-based serial entrepreneur with diverse ventures, including DJing, nightclubs, hot body contests, nail salons, coaching University of Windsor's volleyball team, leading Canada's largest volleyball league (WAMBL), and co-owning Scarehouse Windsor—a premier haunted attraction since 2011. Known for his viral surprise wedding (millions of views, TV features), Sean embodies risk-taking and process-loving innovation, turning failures into successes like immersive horror dinners. Passionate about community (e.g., WAMBL's 45+ years), he inspires with blue-collar roots and no-fear mindset. Connect at scarehousewindsor.com, on Facebook at facebook.com/scarehousewindsor, or Instagram @scarehousewindsor for tickets and events.

Key Takeaways

• Start small: Sean's entrepreneurial spark began selling chips in grade 8, leading to DJing at 16 and self-created jobs like nightclub promotions.
• Embrace risks: From hot body contests (hyped crowds via mic skills) to a viral surprise wedding (planned secretly, featured on TV/Sports Illustrated), failure thickens skin—family "razzing" built resilience.
• Pivot relentlessly: Turned post-2006 border issues into Scare House success; annual 20% revamps ensure freshness, evolving from "terrible" start to profits.
• Innovate experiences: Scare House's immersive dinners (e.g., Cabin in the Woods for 16, Cursed for 10) blend horror themes with meals—trial in 2020 grew to 30+ sessions, quadrupling in 2025.
• Community focus: Coached Windsor's volleyball team, runs WAMBL (Canada's largest league since 1976)—opportunities arise from circles, like teacher handoff.
• No perfect path: Diverse roles (bingo caller, pop boy) show "just do something"—process love over planning paralysis drives success.
• 2025 Windsor outlook: Stable events amid CMHC's easing forecasts—ideal for haunts like Scare House with pre-booked timed ticketing.
• Mindset tip: "No one's perfect; tinker until it works"—apply to business roadblocks for growth.

• (00:05) - Introduction to Sean Lipper
• (07:24) - The Surprise Wedding Story
• (10:35) - Embracing Risk in Life
• (13:07) - The Journey to the Scare House
• (15:02) - Coaching Volleyball and Running a League
• (16:24) - Immersive Dinner Experience at the Scare House
• (17:53) - Planning Your Visit to the Scare House

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