Parksy

I've been in the parking space since 2012. Started with ParkingMadeEasy.com.au in Australia after one afternoon in Sydney where I circled the block for 30 minutes, parked illegally, and got a fine that cost more than dinner — while three driveways on the same street sat empty all day.

The fix seemed obvious: connect drivers with property owners directly. No middleman, no booking fees, just a simple marketplace.

It worked. Tens of thousands of users joined. We expanded to North America with ParkingCupid.com. But for years we ran the same model most marketplaces default to — free to browse, pay to contact.

Then in 2024 I looked at the data and noticed something uncomfortable. Thousands of drivers were visiting every month and stopping just short of messaging a space owner. The intent was there. The friction was killing it.

So we tore down the paywall entirely. Free to search, free to list, free to contact. Not a trial. Permanently.

Within three months, traffic grew over 20% month-on-month. Sign-ups accelerated. Inbound leads started coming from markets we hadn't even targeted.

The lesson wasn't new — it's the same one Airbnb, Craigslist, and Gumtree learned before us. Solve the liquidity problem first. Monetise later. When you stop asking people to pay before they've experienced value, the network starts compounding on its own.

Monetisation now comes through premium memberships, parking operator advertising, and affiliate partnerships — none of which require charging users just to connect with each other.

We've since consolidated everything into Parksy.com — one platform, 120,000+ users, operating across the US and Australia. Still bootstrapped. Still building.

The parking problem is real and largely unsolved. Americans waste $73 billion annually searching for parking. Between 8–74% of traffic in congested areas is just people cruising for a spot. Meanwhile millions of driveways sit empty every day.

The answer was never more concrete. It was better connections.