From Caravan to Exit: The Struggles That Built a Founder | Jacques Greeff

He grew up sleeping on bricks in a tent extension of a caravan — and turned that raw struggle into a life of building and exiting companies.

From bankrupt parents filleting fish in New Zealand to bootstrapping a tech platform out of the printing business, this is the story of resilience, obsession, and choosing struggle as a way of life. In this conversation, the masks come off: money raised too early, founders eating tuna and rice for years, and the real cost of chasing KPIs.

Key Episode Highlights:

From signboards to tech platforms — how a “boring” problem created a powerful business

Why bootstrapping teaches lessons no VC cheque ever could

The brutal caravan childhood that forged founder resilience

Struggle meals, scams, and survival abroad

Honouring family sacrifices while building something bigger

Why business becomes identity — and the richest version of life

The crossroads of raising VC vs. keeping control

Why monetisation is the ultimate validation test

100 true fans vs. 500,000 free users

Tall poppy syndrome, Gen Z ambition, and thinking differently in Australia

Timestamps:

00:00 Intro – Business talk finally begins

00:01 First Startup – From signboards to tech platform

00:04 Bootstrapping – Hard lessons and discipline

00:07 Market Validation – Data, pain points, and talking to users

00:11 Struggle Story – Growing up in a caravan

00:16 Chosen Struggle – Founders chasing hardship

00:17 Struggle Meals – Scams, survival, and hunger in Germany

00:18 Family Sacrifice – Honouring parents’ struggle

00:20 Business Identity – Why founders keep building

00:25 VC Crossroads – Deciding whether to take funding

00:29 Monetisation – Paying users vs. free noise

00:31 100 True Fans – Why depth beats scale

00:36 Content Leverage – Documenting, building in public, and strategy

00:40 Tall Poppy Syndrome – Thinking differently in Australia

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