Co-founder of Adioso. Veteran startup guy based in Melbourne, Australia. Curious observer of economics, sociology, UFC.

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Part 3: Patience

Lorne, Victoria - by BMcIvr

« Part 1: Reality Check

« Part 2: Stunts

I stood in the middle of the street at the top of the hill, taking giant, euphoric gulps of air. I grinned with delight as I watched the moon shining through the scattered clouds and onto the rippling surface of the ocean. All I could hear was the wind in the trees and the waves gently lapping on the beach. With May ushering in a winter chill that normally lasts till about October, the seaside town of Lorne, packed with tourists during the summer months, had returned to its permanent population of less than a thousand. But with the locals all tucked up in bed, I had the town to myself. I gleefully trotted and skipped down the steep hill to the bottom, turned around, then sprinted back to the top.

Suddenly, the world seemed full of promise and hope. The problems were still on my mind: the panicking investors, the aggrieved former team members...

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Part 2: Stunts

« Part 1: Reality Check

GB Hotel, Richmond, VIC, Australia - by Hannah Koelmeyer

“It was just so off-brand for you guys.”

I didn’t really go for the marketing-speak, but I knew what she meant.

It was late April in 2011, and Jenni and I were sitting near the fireplace at the Great Britain Hotel, the delightfully offbeat pub in the inner Melbourne neighbourhood of Richmond, that had been my sanctuary and playground during my chaotic period of a few years earlier. Jenni, one of the people I’d come to rely on to tell me what I needed to hear, was home from London for a brief visit over Easter.

She was talking about the How Much Do You Heart Me? microsite we’d launched a couple of months earlier for Valentine’s Day. Until that moment, not a single person had straight-out told me they thought it was a bad idea. But Jenni was telling me something I’d known deep down all along.

The journey to How Much Do You Heart Me? had started back in...

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Part 1: Reality Check

“You took some funding, and you didn’t make it to the next milestone. That’s what failed startups look like”.

Palace of Fine Arts, San Francisco, by Sudheendra Vijayakumar

It was late on a gloomy Saturday afternoon in Mountain View, and we were doing a walk’n’talk ‘office hours’ session with Paul Graham - "PG” - on the street outside the Y Combinator office.

“What do you have to show for the funding you’ve taken so far?”

I tried to explain. “We felt we needed to build our own technology platform for flight search, because nothing already existed to support the product we were trying to build. So, basically we spent it on back-end engineering.”

“Well that sure was a mistake,” he huffed.

“How do you know your product is something people want?” The pg-bot had engaged.

It was hard to explain.

It was the way people’s eyes lit up as they exclaimed, “That’s exactly what I’ve been wanting for years!” when we talked about Adioso.

It was the emails...

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Google Flight Search means little for Adioso & Hipmunk

NB This post was republished on Tnooz on 15 Sep 2011.

Being located 17 hours ahead of Silicon Valley often has you lagging behind on the big news. On waking this morning at home in Melbourne, the inbox and Twitters were abuzz. Google had launched a flight search product.

As the “other” YC-funded travel search startup, people just wanted to be sure we’d heard the news. Most were just interested in our thoughts. At least one feared for our future.

Over at HackerNews, once you waded past the protracted debate over Google’s evilness, several commenters asserted with certainty that this would spell death for travel startups like Hipmunk. The news had one anonymous travel startup founder throwing himself out the proverbial window.

When Google first announced its intention to acquire ITA Software in July 2010, we at Adioso thought it was a huge deal that would materially influence our...

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Our Y Combinator interview experience

In November 2008, Fenn and I had one of the more momentous experiences of our lives. After six years working together on various startup ideas from in our home town of Melbourne, Australia, we were selected for an interview with Y Combinator in Mountain View, California. Here’s how we got through it.

The Preparation

After allowing ourselves a couple of days to come to terms with the surprise of our interview invitation, we set about preparing. As we already had a working product, we didn’t need to spend much time on our demo. From YC’s interview preparation guide, the most important points seemed to be that we should have a good idea of how we’d make money, and find someone to help us practice our interview skills.

As complete outsiders to Y Combinator and Silicon Valley, practicing with YC alumni or experienced operators in the Valley didn’t seem to be an option. We didn’t even...

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