Why I Drained My Life Savings For a Sailboat as a Broke College Student

I know the title sounds ridiculous. A broke college student draining his savings for a sailboat? But by the end of this, I think you’ll understand why it wasn’t reckless but it was the first time I chose a life that actually felt like mine.

Who I Am

Hi, I’m Bene, Skipper of Dog House, a 28‑foot sloop we rebuilt from abandoned to sea‑worthy floating home. I was born in the Philippines and moved to the US at 10. At 18, I enlisted in the US Navy as an engineer, and that’s where my adventures with boats began.

Quick TLDR: the military and the government it serves can suck it, but the family I made there means everything to me. I served on a Cruiser, small by Navy standards and the quarters were tight. When I left, I swore off boats forever.

Life After the Navy

After getting out, I used my GI Bill and enrolled in a Marketing program in San Francisco. I worked full‑time and picked up every odd job I could: Fraud & Organized Crime Investigator, house painter, newspaper delivery, even camera operator gigs in Hollywood. If it paid, I took it. I didn’t know what I was saving for I just saved.

How the Sailboat Idea Started

Like everyone else during the pandemic, I was doom scrolling on social media too much. But instead of dance trends, I found people stuck on their sailboats in Puerto Rico, Thailand, and other places I’d only dreamed of. If I had to be trapped somewhere, that didn’t look too bad.

It reminded me of living on a ship. Maybe enough time had passed. Maybe I wasn’t done with boats after all. I was rediscovering the pull of the ocean. So I started looking. But with so many types of boats, where do you even start?

Why a Sailboat Made Sense

Sailing is one of the oldest and most sustainable ways to move around and that mattered to me. A sailboat has way less space than a motor yacht, but the theoretical unlimited range? That was the hook.

One big problem: I had zero experience sailing. Living on a warship is not the same as owning and maintaining your own boat.

So I wised up and took an ASA introductory course, got my boating license, and finally felt confident enough to get on the water.

Finding the Right Boat (And Why a Project Boat)

Once I had the basics down, all that was left was finding the boat. Polished sailboats can cost as much as a mortgage, but project boats? Those get ignored. People avoid them because they can be money pits.

But for me, a project boat made sense. I wouldn’t be scared to make mistakes. I didn’t need to cry over every scratch. I could focus on what mattered: being on the water and learning.

That’s how Dog House came into my life. Rough around the edges, overlooked, but full of potential.

So Why Did I Drain My Savings?

Here’s the truth behind the title.

I didn’t drain my savings because I was reckless. I didn’t do it for aesthetics or to chase some Instagram version of freedom. I did it because, after everything, the Navy racks, the odd jobs, the long nights in San Francisco… I finally understood what I’d been saving for.

I wasn’t saving for a house, or a car, or some “responsible” milestone. I was saving for a life that felt like mine.

A project sailboat isn’t the obvious choice for a broke college student. It’s not the safe choice. But it was the first choice that made sense to me. A boat I could rebuild, learn on, screw up on, and eventually sail beyond the limits of whatever life I thought I was supposed to live.

So yes, the title contradicts itself. Why would someone with barely any money spend it all on a boat?

Because sometimes the thing that looks irresponsible from the outside is the only thing that feels right on the inside. Sometimes the “broke” decision is the one that makes you feel the richest. It was the moment I stopped waiting for the “right time” and finally bet on the life I wanted.

Thanks for sticking around. Subscribe. Come back for the next chapter of this wild little life we’re building on the water.