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What happens when you are grinding 14-hour days, hitting your financial targets, but still feel completely empty inside? In this deeply vulnerable episode, Tiffany sits down with Jenny, a highly driven entrepreneur juggling Airbnbs, real estate investing, and a brand new wholesaling operation. Jenny came in seeking strategies to scale her new acquisitions rep, but Tiffany quickly uncovered a much deeper issue: a severe lack of clarity surrounding her ultimate "end game."
Listen in as Tiffany shares the untold story of how the stress of running multiple unaligned businesses nearly broke off her engagement to Josh in their first year. You will learn why setting arbitrary financial goals like "$50,000 a month" will ultimately leave you unfulfilled, why your spouse might be joining the business for all the wrong reasons, and why managing a high-performing employee without auditing their calls is a recipe for disaster. If you feel like you are running in a million different directions and losing sight of why you started in the first place, this episode will help you confront the hard truths and redefine your path. Listen and enjoy the show!
You’ll Learn How To:
What You’ll Learn in This Episode:
Who This Episode is For:
Why You Should Listen:
It is easy to hide behind "busy work" and arbitrary financial targets, but eventually, the lack of a true north will catch up to you and your relationships. By listening to this raw coaching session, you will learn how to pause, ask yourself the hard questions, and rebuild your business around what actually brings you joy. You will walk away with actionable strategies to align with your spouse, manage your team effectively, and create a business that serves your life instead of draining it.
Connect with Jenny:
Follow Tiffany and Josh here:
By Tiffany and Josh High5
7373 ratings
Send us Fan Mail
What happens when you are grinding 14-hour days, hitting your financial targets, but still feel completely empty inside? In this deeply vulnerable episode, Tiffany sits down with Jenny, a highly driven entrepreneur juggling Airbnbs, real estate investing, and a brand new wholesaling operation. Jenny came in seeking strategies to scale her new acquisitions rep, but Tiffany quickly uncovered a much deeper issue: a severe lack of clarity surrounding her ultimate "end game."
Listen in as Tiffany shares the untold story of how the stress of running multiple unaligned businesses nearly broke off her engagement to Josh in their first year. You will learn why setting arbitrary financial goals like "$50,000 a month" will ultimately leave you unfulfilled, why your spouse might be joining the business for all the wrong reasons, and why managing a high-performing employee without auditing their calls is a recipe for disaster. If you feel like you are running in a million different directions and losing sight of why you started in the first place, this episode will help you confront the hard truths and redefine your path. Listen and enjoy the show!
You’ll Learn How To:
What You’ll Learn in This Episode:
Who This Episode is For:
Why You Should Listen:
It is easy to hide behind "busy work" and arbitrary financial targets, but eventually, the lack of a true north will catch up to you and your relationships. By listening to this raw coaching session, you will learn how to pause, ask yourself the hard questions, and rebuild your business around what actually brings you joy. You will walk away with actionable strategies to align with your spouse, manage your team effectively, and create a business that serves your life instead of draining it.
Connect with Jenny:
Follow Tiffany and Josh here:

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