EPISODE · Jun 24, 2026 · 34 MIN
She Made $80K on Her First Flip, Then Lost $75K to a Contractor
from The Millionaire Blueprint · host Anna Mendoza, Ashley Cleary
After making more than $80,000 on her very first house flip, Ashley Cleary thought she had the process figured out. Then her second deal took a completely different turn, leading to delays, contractor issues, and a $75,000 lesson that tested everything she thought she knew about real estate investing.Hosts Anna Mendoza and Ashley Cleary turn the tables for a deeply personal episode as Ashley shares how she went from working as a nurse and living paycheck to paycheck to making $80K on her first flip, replacing her husband's W2 income, and navigating one of the biggest setbacks of her investing journey. From managing contractors and running projects herself to Airbnb investing, cost segregation, and balancing family with entrepreneurship, this episode is packed with hard-earned lessons for anyone looking to build wealth through real estate.Timestamps00:00 – Why Real Estate Investing Will Always Involve Risk00:4101:28 – How Ashley Cleary Got Started in Real Estate Investing04:13 – Making $80K on Her First House Flip05:20 – Managing a Renovation Project Without Experience07:59 – Turning a Fallbrook Property Into an Airbnb10:53 – Contractor Delays and Having Control of the Project14:42 – How Ashley Would Handle Contractors Differently Today16:53 – Why Local Real Estate Investing Beats Long-Distance Investing19:22 – Cutting Costs and Pivoting to Stay on Budget25:02 – Building Equity Through Airbnb and Value-Add Investing25:49 – Using Cost Segregation and Real Estate to Replace the W2 29:52 – The Mindset Shift Every Real Estate Investor Needs33:44 – Wrapping It UpTopics CoveredHouse flipping for beginnersContractor mistakes in real estateLosing money on a renovation projectAirbnb investingReal estate investing in CaliforniaCost segregation explainedLeaving a W2 jobReal estate tax strategiesBalancing family and entrepreneurshipWomen in real estate investingLearning from failureBuilding wealth through real estateKeywordshouse flipping, real estate investing, contractor horror stories, losing money in real estate, Airbnb investing, cost segregation, real estate tax strategies, California real estate investing, women in real estate, passive income, financial freedom, leaving the W2, value-add investing, house flip mistakes, beginner real estate investing, real estate podcast, West Coast Wealth BuildersHashtags#RealEstateInvesting #HouseFlipping #AirbnbInvesting #WomenInRealEstate #FinancialFreedom #PassiveIncome #ContractorHorrorStory #RealEstatePodcast #HouseFlip #Entrepreneurship #MillionaireBlueprintPodcast
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She Made $80K on Her First Flip, Then Lost $75K to a Contractor
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