Triplets, a Crash, and a $50k First Deal | Lynn Schwarber | Part 1 episode artwork

EPISODE · Jul 10, 2026 · 26 MIN

Triplets, a Crash, and a $50k First Deal | Lynn Schwarber | Part 1

from Chief Milestones · host Reshma Vadlamudi

This episode isn't about real estate advice. It's about what it takes to start a commission-only career the year after the housing market collapsed.In Part 1 of this conversation, Lynn Schwarber - agent with Comey & Shepherd and investor in long-term and short-term rentals - breaks down how she went from 20-year TV news anchor to full-time agent in 2010, right after the crash, with newborn triplets at home.This was not a career-change story. It was an income-risk problem.We cover: Why she left two decades in journalism to bet on a fully commission-based businessThe math behind starting full-time the year after the housing market bottomed outHow a routine house showing turned into a one-hour bidding-war decision - and her first AirbnbWhy 75% of new agents quit in year one, and what separates the ones who don'tWhy she's now cautioning against short-term rentals in markets that have gotten crowdedIf you're building something with no guaranteed paycheck, or making a bet on timing you can't fully control, this conversation will feel familiar.This isn't a highlight reel. It's a practical breakdown of how a real operator built a business under pressure, not in hindsight.Reach out: [email protected] Milestones is a video podcast featuring honest conversations with founders, parents, and investors about building real businesses, staying healthy, and raising families.New episodes release Tuesdays and Fridays.Youtube: https://www.youtube.com/@ChiefMilestonesInstagram: https://www.instagram.com/chiefmilestones/Spotify: https://open.spotify.com/show/7HLDAe7SP3GnJSTOgAQqLy?si=6e9ac82be46f413cApple Podcasts: https://podcasts.apple.com/us/podcast/chief-milestones/id1861185226

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This episode isn't about real estate advice. It's about what it takes to start a commission-only career the year after the housing market collapsed. In Part 1 of this conversation, Lynn Schwarber - agent with Comey & Shepherd and investor in long-term and short-term rentals - breaks down how she went from 20-year TV news anchor to full-time agent in 2010, right after the crash, with newborn triplets at home. This was not a career-change story. It was an income-risk problem. We...

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Triplets, a Crash, and a $50k First Deal | Lynn Schwarber | Part 1

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