Every founder’s got a story. Some start with a pitch deck. Tim Brown’s started with Cuban rum.

And while a pirate’s life was not to be, that first foray into business was just the beginning.

In Episode 3 of Risky Business, we sit down with Tim Brown; a former journalist-turned-aspiring-rum-baron-turned-EV-trailblazer and now CEO of WhipSmart, who’s helping Aussies ditch the petrol pump and plug into the future.

Tim’s path? Think less straight line, more treasure map. From rum start-ups and failed shortcuts to last-minute pivots, it’s been a ride, and one that’s now charging full speed ahead in EV leasing and finance.

He’s passionate about smart commercial ideas, technology, and the impact both can have on the world – especially in the green energy, automotive and sustainability space.

What’s Inside This Episode:

• The failed shortcut that set him back
• The one hire that can make or break a small business
• The everyday skill that still trips people up
• What he’d tell his 20-year-old self (and you should hear too)

And more..

The Rum That Didn’t Flow

WhipSmart officially launched in 2024, but it wasn’t Tim’s first rodeo. His earlier ventures (including Cuban rum) didn’t go the distance.

“I was going to be a rum baron. You know, pirating the high seas.”

Tim quickly discovered that in the alcohol game, logistics rule the day:

“What I learned very quickly… the whole alcohol game is won or lost on logistics. If you come to market with one single brand… that’s not how it works.”
It was a harsh lesson, but one that helped lay the groundwork for what came next.

That honest, confronting moment propelled Dave to step away from security into uncertainty.

Burn the Boats, Build the Business

He took those hard-earned lessons, put WhipSmart through an incubator program, and prepared to launch with a partner. That partnership didn’t pan out—and the business almost didn’t either.

“Everything was fired up for that partnership to kick off… but as it turned out, things fell apart with that, and I was, sort of left clutching at straws for a little while. And nearly the whole thing fell apart on me.”

Instead of folding, Tim pivoted.

“As luck would have it now, I fired it up on my own. I’m, you know, a majority shareholder. I’ve got full control.”

HR isn’t Just About Hiring

One of Tim’s biggest learnings?

“HR is probably the most undervalued issue that really takes time away from your day… It’s not just recruitment. It’s office politics, making sure people get along, knowing when to hire – and what order to do it in.”

In small teams, every person matters. Tim knows the impact one hire, or departure, can have.

“Everyone in a small business is some sort of linchpin.”

The Skill Everyone Underestimates

It’s not strategy. Or finance. Or even marketing.

“Just bloody general IT skills. Knowing how to turn something off and on again. Convert a PDF. Basic stuff, but it makes a huge difference.”

And when something goes wrong? Tim’s learned to figure it out—or at least learn from it the first time.

“If someone shows you how to do it, learn it. Do it next time yourself.”

The Investment That Paid Off

Despite his early tech frustrations, Tim’s biggest investment paid off:

“The website. One hundred percent. It’s in a massively competitive market, and we had to build trust from day one.”

Tim credits his website and specifically its design, UX, and polish as one of the most important parts of their early traction. Even if users were to come to a roadblock, leads came in thanks to the look, feel, and clarity of WhipSmart’s online presence.

The Business Book That’s Not a Business Book

When asked which book has shaped his business mindset, Tim doesn’t rattle off the usual leadership classics. Instead, he name-drops Fear and Loathing in Las Vegas by Hunter S. Thompson.

“I was originally a journalist, right. And Hunter just became a bit of a hero. Not so much from the movie, but that book.”

“So, the book that I always come back to… it’s Fear and Loathing in Las Vegas.”

At first, it might not seem like the obvious choice—but Tim sees inspiration in Thompson’s fearless creativity and relentless drive:

“It was just all about someone who had a lot of initiative and a lot of drive and a lot of passion just to do whatever the hell he wanted, but a lot of imagination. Yeah, the guy just had oodles of it, creativity. And that creativity is really what spawns good, good business ideas. And you know, if you’re not coming up with multiple business ideas, you know, in your sleep and you know this, you’re probably not coming up with enough to find the right one that’s going to work.”

“There’s nothing in that book necessarily that I can think of off the top of my head that sort of gives any good business advice, but it does show that, you know, you can take risks and you can do crazy things and you can be wildly successful.“

Words for His Younger Self

Tim’s parting wisdom to his younger self is a reminder for all of us:

“Concentrate. Work harder. And, you know, don’t spend so much time doing utter shit when you’ve got a few, you know, spare days.”

He goes on:

“It takes a while to build a career. It takes a while to get experience. But you can do things a lot earlier than you think you can.”

And the biggest confidence blocker?

“When you are 20, you think, ‘no one’s going to take me seriously’. There’s zero reason why you can’t be successful… doing something really impressive in your mid-20s.”

Watch the Full Episode Now –> Risky Business

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