Cover of Like A Boss

Like A Boss

Like A Boss

By: Pilot Podcasts
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Being your own boss sounds great, until you realize nobody gave you the instruction manual. Like A Boss is an entrepreneurship and business podcast featuring candid, funny, and sometimes unbelievable conversations with entrepreneurs at every stage of their journey. From side hustles and startups to business failures, financial wins, and lessons learned the hard way, we get into the realities of building a business that nobody posts about on social media. Whether you're dreaming of quitting your 9-to-5, launching your first business, or figuring out your next big move, there's something here for you. Because everybody wants to be the boss. But do you know what it takes? A Pilot Podcasts Network Original Like A Boss is part of the Pilot Podcasts Network, where listeners help shape what gets made next. Join our community of Piloters to discover new podcasts, share your opinions, test upcoming shows, and help decide which ideas deserve the spotlight. Your ears. Your opinions. Your network. Become a Piloter: https://pilotpodcasts.com/listeners/ Hosted on Ausha. See ausha.co/privacy-policy for more information.Pilot Podcasts LLC Economics
Episodes
  • Don't Quit Your Day Job ... Yet

    Don't Quit Your Day Job ... Yet
    22 Oct 2026

    Thinking about quitting your 9-to-5 to become your own boss? Not so fast! In the premiere episode of Like A Boss, host Krystle Waters sits down with serial entrepreneur (and her big brother!) Harold Waters to talk about the realities of leaving corporate America, building multiple businesses, and knowing when it's really time to take the leap.

    From workplace haters and expensive business mistakes to unpopular opinions about hustle culture, Harold shares the wins, setbacks, and downright unbelievable moments that come with entrepreneurship. Plus, find out which songs make their ultimate hustle playlists!


    Because betting on yourself is one thing. Surviving the chaos? That's another story.

    🚀 Like A Boss is part of the Pilot Podcasts Network.

    At Pilot Podcasts, listeners help shape, test, and launch the next generation of podcasts. Join our community to discover new shows, share your feedback, and get access to exclusive opportunities.

    🎧 Become a Pilot: https://www.pilotpodcasts.com/listeners

    📱 Follow us on Instagram: @Pilotcasts


    Hosted on Ausha. See ausha.co/privacy-policy for more information.
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    1 hr and 3 min
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