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In this episode of What’s Your Deal?, Matt Uhler sits down with Keira Hamilton, a former high school English teacher with a master’s in education from UC Berkeley who made an unexpected leap into business ownership. Keira and her husband bought their first business — a San Francisco laundromat — in 2023, learned fast why “passive income” is often a myth, and then sold the laundromat in 2024 after improving systems and operations to make the business more transferable. From there, they moved to San Diego and acquired their next business: Sunshine Window Cleaning, an off-market service company they found through cold outreach. Keira breaks down what most buyers underestimate (especially proximity, staffing realities, and operating complexity), how transparency builds trust in a transaction, and why “perfect certainty” isn’t a requirement to buy — but courage, skill-building, and runway management are. If you’re exploring your first acquisition, thinking about “semi-absentee” ownership, or trying to understand what makes a business easier to buy, run, and sell — this one is packed with real-world insight. Timestamps: 0:16 – Meet Keira Hamilton: teacher → business owner 2:16 – Pivot from real estate to buying a business 5:27 – Finding the laundromat + broker challenges 8:02 – Cash offers, family financing & SBA realities 12:36 – Valuation: art vs science + speed matters 14:24 – Laundromat myth-busting & proximity lessons 19:23 – Why they sold the laundromat after 16 months 22:18 – Selling fast through transparency & systems 25:24 – Increasing value with SOPs and organization 32:38 – Off-market window cleaning acquisition 35:38 – Knowing when to stop searching & take the leap 44:10 – No industry experience & surviving the transition 50:55 – Working with a spouse + partnership lessons 55:59 – Gratitude, support systems & final takeaways Connect with Keira: / keirahamilton https://sunshinewindowcleaningsd.com/ https://www.instagram.com/ahigherflow... https://www.instagram.com/sunshinewin... / @keira_hamilton Follow Us on Social Media Instagram: @AmpedSuccess LinkedIn: Amped Success Tiktok: @Ampedsuccess YouTube: @AmpedSuccess 📧 Contact Us: Interested in sponsorship opportunities or being a guest on What’s Your Deal? Email info@ampedsuccess.com