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The Harsh Truth of Wholesaling Business

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Author

Jessey Kwong

Pebble Co-Founder

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The Harsh Truth of Wholesaling Business

Aug 21, 2025

Podcast

The wholesaling business isn’t all highlight reels and quick wins. Behind the scenes, it’s full of tough decisions, painful lessons, and resilience when everything feels like it’s falling apart.

In this episode, Jessey reconnects with Steve Enns to uncover the real story of building and scaling a wholesaling business. From quitting a six-figure job after just one deal, to growing a 65-person team, to downsizing back to 20, Steve opens up about what it actually takes to keep going.

You’ll learn why chasing shiny objects nearly destroyed his business, how he rebuilt stronger with less overhead, and why the “valley of death” is a stage every entrepreneur has to face.

In this episode:

  • Why mentors and coaches are critical when starting out

  • The danger of chasing other people’s visions instead of your own

  • Lessons from scaling up to 65 employees and downsizing back to 20

  • How to survive the “valley of death” and come out stronger


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© 2024 Pebble REI Inc. All rights reserved.

Try Pebble FREE
for 7 days

Land investing is messy. Get organized and grow your land business with one platform.

By subscribing you agree to with our Privacy Policy and provide consent to receive updates from our company.

© 2024 Pebble REI Inc. All rights reserved.

Try Pebble FREE for 7 days

Land investing is messy. Get organized and grow your land business with one platform.

By subscribing you agree to with our Privacy Policy and provide consent to receive updates from our company.

© 2024 Pebble REI Inc. All rights reserved.

Try Pebble
FREE
for 7 days

Land investing is messy. Get organized and grow your land business with one platform.

By subscribing you agree to with our Privacy Policy and provide consent to receive updates from our company.

© 2024 Pebble REI Inc. All rights reserved.