When you’re building a business that appeals to investors, you have to show that you can scale and stabilize at every level.

But here’s the thing - scaling isn’t clean or painless…it’s not supposed to be. It almost always means that things will break. Systems will strain, processes will collapse, and the business will feel unstable.

This is inevitable. Growth will always stress the business.

As a founder, your mindset shouldn’t be preventing stress; it should be preparing for it.

Every stage of growth demands that you adapt, fix what cracked under pressure, and put new structures in place that can carry you to the next level.

And part of that structure isn’t technical at all, it’s human. Your inner circle has to be balanced. Too many yeses and you’ll miss the weak spots. Too many nos and you’ll never take the risks growth requires.

What should early-stage founders be thinking about as they grow? How did my guest turn a $30K loan from his 401K into 20+ million in real estate and a $10M a year company?

In this episode, I’m joined by entrepreneur, mentor, short-term rental expert, and investor, Josh Hatter.

We unpack why scaling is supposed to feel uncomfortable, how to treat breakage as proof of progress, and why curating the right mix of voices around you might be the most important system you ever build.

• How Josh turned a $30k 401k loan into $20M+ of real estate assets and $100M under management

• How childhood chaos became his greatest entrepreneurial strength

• The real reason rental arbitrage is dangerous (and what to do instead)

• How to survive a once-in-a-lifetime industry collapse like COVID in hospitality

• Why scaling means breaking your systems on purpose

• The hardest balancing act in entrepreneurship

• Why owning the real estate your business operates in is one of the smartest wealth moves you can make

• How Josh formalized his mentorship group into a nonprofit

Guest Bio

Josh Hatter is a Short Term Rental (STR) and Bed & Breakfast (B&B) expert investor and entrepreneur. After working in Corporate America, Josh bet on himself to grow a $30,000 401 (k) loan to $20M+ of assets in 12 years of real estate investing through his principles of information arbitrage. He helps high achievers exit corporate America and reach financial independence through hospitality real estate. Visit https://www.joshhatter.com/, send an email to [email protected]. To learn more about the mentorship program, visit https://keyscollective.org, and to stay at Josh’s rentals, visit staycvp.com.

About Your Host

Jayla Siciliano, Shark Tank entrepreneur turned real estate investor, excels in building brands, teams, and products. CEO of a bi-coastal luxury short-term rental company, she also hosts the Seed Money Podcast, where she’s on a mission to help early-stage entrepreneurs turn their ideas into reality!

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The information in this podcast is educational and general in nature and does not take into consideration the listener's personal circumstances. Therefore, it is not intended to be a substitute for specific, individualized financial, legal, or tax advice.