From Caravan to Exit: The Struggles That Built a Founder | Jacques Greeff
Sun Aug 17 2025
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
Follow Our Podcast Studio:
Follow Our Podcast Studio:
🎥 https://www.linkedin.com/company/candid-studios/
Nick’s Apps:
🧠 SCULPTED → https://sculpted.site
📚 LivFree → https://livfree.live
⚽️ B42 → https://b-42.com
Follow Nick:
🔗 https://www.linkedin.com/in/nicholas-kratochvil/
📸 https://www.instagram.com/nickratochvil/
Meet The Team:
🎬 Editor – https://www.instagram.com/jethropaco/
🎨 Design – https://www.instagram.com/shanika.j11/
🎙 Producer – https://www.instagram.com/_charlieslattery/
📂 Podcast Manager – https://www.instagram.com/alfiogangemi_/
Hosted on Acast. See acast.com/privacy for more information.
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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 Follow Our Podcast Studio: Follow Our Podcast Studio: 🎥 https://www.linkedin.com/company/candid-studios/ Nick’s Apps: 🧠 SCULPTED → https://sculpted.site 📚 LivFree → https://livfree.live ⚽️ B42 → https://b-42.com Follow Nick: 🔗 https://www.linkedin.com/in/nicholas-kratochvil/ 📸 https://www.instagram.com/nickratochvil/ Meet The Team: 🎬 Editor – https://www.instagram.com/jethropaco/ 🎨 Design – https://www.instagram.com/shanika.j11/ 🎙 Producer – https://www.instagram.com/_charlieslattery/ 📂 Podcast Manager – https://www.instagram.com/alfiogangemi_/ Hosted on Acast. See acast.com/privacy for more information.