Jason Lippman’s entrepreneurial journey includes scaling a real estate portfolio to hundreds of homes, losing everything during the 2008 financial crisis, and rebuilding a successful financial services company from scratch.

At one of his lowest points, his wife called from the grocery store because her debit card had been declined — and there was nothing he could do about it.

In this episode, Jason shares the hard lessons from losing everything, the mindset required to rebuild, and why fast-growing companies often face their biggest challenge: cash flow.

We discuss:

• The rise and collapse of a vertically integrated real estate business
• The painful lessons of the 2008 financial crash
• Rebuilding after financial devastation
• Why growth often makes cash flow problems worse
• Building a remote-first financial services company
• Hiring experienced operators instead of junior staff
• Leadership lessons from endurance sports and aviation

This episode is a candid look at resilience, leadership, and the realities of entrepreneurship when things don’t go according to plan.

Feeling stuck in your business?

It’s ok. We’ve all been there… You simply don’t have time for vision and growth. You feel frustrated, anxious, and stuck because goals aren’t being met, processes aren’t followed, and your team isn’t on the same page. Time after time, you’re putting out fires only fast enough for the next one to pop up.

Get OUT of the Sh*t Show

Let’s build your team and guide them to the next level.