Talking Digital Q&A #3: Tom Howard, co-founder Adioso.com


Tom Howard founded travel site Adioso alongside friend Fenn Bailey in 2008. Tom and Fenn had worked with eachother in various guises for 10 years – meeting whilst both working at pioneering Australian ISP OzEmail, and continuing to work together at Pacific Internet and then on their own various digital and development businesses.

Both are tenacious, creative and inventive guys. I should know. Tom and I went to university together from 1996-1999 and we then lived together from 2000-2003. I saw first hand Tom learn the fundamentals of code (he studied Accounting) and we even built a few websites together (2001 Offshore Festival, 2001 and 2002 Falls Festival). Since those humble beginnings Tom, alongside Fenn, have built a brand that has been funded by a bunch of Silicon Valley heavy hitters and has generated a lot of attention. Talking Digital spoke with Tom.

Talking Digital: When you and Fenn started Adioso, what were your goals? What were you trying to solve?

Tom Howard: We were just trying to make it easier for ourselves and our friends to find the best flight deals, particularly to South East Asia, but to anywhere really.  We found it bizarre that you couldn’t just search for the cheapest flights, say to Thailand or Vietnam in the next 2-3 months, without having to provide a specific date or airport.

When we started out 4-5 years ago, we didn’t have any more ambitious goals than that.  It certainly hadn’t crossed our minds to try and become a serious player in the travel industry or seek Silicon Valley funding.  It was only after we found that so many others had a similar need and reacted with such excitement to our product that we decided to focus on it.

Since then, the core goal really hasn’t changed a whole lot in terms of what we’re trying to do with the product, but the vision of the company has broadened to being about making it easier and more affordable for people to having awesome leisure travel experiences more often.

TD: Explain if you can, the process of applying for and being involved in Y Combinator?

TH: We applied in late 2008 and were accepted into batch of early 2009.

The application process just involves answering a bunch of questions on a web form, which are really about establishing that you’re a solid team and that you have a track record of building impressive things.

We didn’t think we had a huge chance of getting an interview, but sure enough we did, so we frantically flew ourselves over to Mountain View, California for the10-minute interview.

We learned later that for that batch, being the lowest point of the GFC, YC was particularly looking for teams that were extremely resilient and able to survive any hardship, so I think the fact that Fenn and I had been friends and collaborators for such a long time (about 8 years prior to that) and had made the effort to get there from Australia played well in our favour.

The YC program itself is really quite casual and informal.  You’re required to move to Silicon Valley for the 3 months, and the main part of the program is the weekly Tuesday night dinner, at which you catch up with the other companies to chat casually about what you’ve been doing the past week, then listen to a talk by a guest speaker.

We had some great talks by the likes of Jack & Biz from Twitter, Jawed of YouTube, Craig Silverstein of Google, Chris Sacca and Ron Conway.  The great thing about the talks is that everyone is sworn to secrecy and speakers talk a lot more candidly than they would in public, so you get some of the juicier insights into what went on in the earliest days of their companies.

For the rest of the time, you’re just back in your apartment working like crazy on your product, trying to get it to the most impressive state possible in time for Demo Day.  You’re able to make appointments with Paul Graham and the other YC parters to seek advice and guidance, but it’s all very informal.

Demo Day happens at the end of the 3 months, and for us it was a 6-minute presentation to a room full of angel investors and VCs (these days, because there are 60+ companies per batch, the presentations are about 2 mins).  After that we moved into fundraising mode and were able to raise a decent amount of funding to carry us through for the next 9-12 months.

So in short, the main point of the 3 month YC program is to just get a great product built, get as much advice and support as you can from smart, successful people, then get in front of investors.

After that, you become part of the Y Combinator alumni network, and even after 3 years, we still have a lot of contact with founders from our own batch and other batches, and can still reach out to the YC partners for advice and introductions.

TD: How do you balance the demands of being a product guy/strategist/developer/business guy? How do you find you balance the requirements of operating a business (finances, leases, contracts, funding) with the requirements of building a product? (coding, dev etc)

TH: I must stay I’m not particularly good at balancing a lot of different demands.

At the moment, the things that take up my time are: fundraising, hiring, conceptualising the product, and leading the company strategy.  Which really means I just spend most of my time talking to people.   It could probably be said that I’m the lead product designer, but that just means mocking up wireframes in Balsamiq then talking to the design and front-end dev guys about implementation.

I do miss writing code and working directly on the product, and I started getting back into that a little, late last year, and really enjoyed it.  What currently stops me from doing it more is that it needs uninterrupted focus and plenty of time to think about it when you’re away from the computer.

Paul Graham says he’s often observed that people tend not to get any product work done when they’re in fundraising mode, the reason being that it becomes the all-encompassing thing they think about all the time, including when they’re in the shower, so they just don’t have any attention left to give to product & code.  I can certainly relate to that.

I’m looking forward to having a solid round of funding closed over the next few months, as well as some dedicated business development talent on the team, so I can get back to playing a role in actually making the product.

TD: How have you seen the Australian start-up community evolve over the past 10 years? How do you feel it compares to the US?

TH: It’s changed a lot. When Fenn and I started our first company in 2003, it was the aftermath of the dotcom crash, and all the big names like Sausage Software, Davnet and LookSmart had come and gone from the local scene, and there just wasn’t any local tech startup community that we were aware of.  So we were pretty much going it alone, and interacting only with a handful of other small companies in the ISP & voice infrastructure space that we were in.  It was a pretty lonely place and there wasn’t a lot of support.

It was when we made our move into consumer web with Adioso that I started reaching out for a community of like-minded people, and sure enough something was starting to take shape.  Cameron Reilly had been running is MODM events for a year or two, and The Hive monthly networking events were starting to draw big attendances, and Twitter was taking off and making it far easier to connect with people.   Through those networks we started interacting with guys like Steve Sammartino of Rentoid, Johnny & Chris from Docoloco, who became kindred souls in the consumer web space, though it still didn’t seem like there were many of us.

After we came back from YC in mid 2009, it seemed that things had started taking off in a huge way, and now the local scene is extremely vibrant.  There’s now a huge range of co-working spaces (Inspire9, York Butter Factory), meetups & networking events (Silicon Beach, Social Media Club, Ruby, Python, Mobile Monday), incubators and early-stage funding groups (AngelCube, Aurelius Digital, Future Capital Fund, Adventure Capital) and newsletters like Startup Digest and The Fetch.  There are a whole lot of people who are working on interesting startups, some who have taken big funding rounds in the US (eg, 99designs & Kaggle), and plenty of people who are well connected to Silicon Valley.

So these days, it’s just much much easier to find co-founders and fellow-travellers on your startup journey, and there are many more ways to find the mentorship, funding and introductions you need to get ahead.

I sometimes worry that there’s a little too much hype and that some people might fall into the trap of just being in it for the sake of being part of the scene and forgetting that you still need to do the really hard work to build a great company.  But you can try to hard to find things to worry about at times 🙂  On the whole, it’s great.

TD: Given your years of experience and learning, what’s the best advice you could give someone thinking of starting a start up business?

TH: I’m not one of those people who says things like “just do it, it’s the best thing you’ll ever do”.  It’s not for everyone, and it’s well worth being very cautious about. I guess the best advice I’d give is that you should expect it to take a long time, and be willing to spend a long time doing it.  If you’re looking for a way to get rich quickly, a startup isn’t it. Contrary to a lot of people, I don’t think startup success is particularly difficult.  It involves some difficult experiences, like financial and relationship strains, and frequent hits to your self-esteem, but they don’t take genius to overcome, just persistence and resilience. All the skills that are needed to make it in startup life can be learned by simply spending enough time doing it.

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2 responses to “Talking Digital Q&A #3: Tom Howard, co-founder Adioso.com

  1. Interesting story, Ben and Tom. Fascinating peek into the AU start-up scene – I had no idea it was so advanced. So persistence and resilience beat genius … I’m sure that gives many hope.

  2. Great read – thanks for sharing.

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