Reflections on startup life: Week 75

It’s been another busy week. Alex has progressed significantly with the new index and we are days, if not hours away from releasing it. There’s another change banked up behind this one already (allowing you to login in to Trunk.ly with Twitter) and a feeling of excitement that we’ll finally start moving forward quickly again.

For me, the highlight was been a trip to Sydney for two days. I went to meet with Rand Fishkin from SEOmoz who was there for a search conference. Rand is our biggest supporter and has been actively promoting Trunk.ly since our first beta release. Given he’s normally in Seattle, it was too good an opportunity to catch up and say hi for the cost of a cheap ticket. We had a great time, a nice lunch in China Town and a coffee and shared lots of ideas and product vision for Trunk.ly. I really appreciate his time, and he really helped me to firm up the product vision a little better.

I then spent the rest of my time in Sydney catching up with a few mentors who’ve been instrumental since “Bootup Camp” in launching Alex and I on our journey together, as well as some others in the startup scene to share news and ideas. Thanks all for your time and conversations, it was really appreciated (and special thanks to Brian and Janet for letting me crash their spare bedroom for the night and to Alex and Rob of MobLabs for letting me co-work out of their office).

With our upcoming trip to San Francisco (leaving in 7 days) very much on my mind, I really appreciated the opportunity bounce ideas, layout the vision and test the concepts with a new audience. It’s really refined it even further.

What I fear the most

With all these conversations and discussions about the future, one question has come up that caused some thought between Alex and myself, which is “What do you fear the most?” After tossing it around a few times, we still couldn’t answer this to our satisfaction. There are LOTS of things that we worry about all the time:

• Our design isn’t strong enough yet and we really need to improve the UX. But that doesn’t stop people signing up (although maybe others don’t). It’s not uncommon for us to see tweets like “Trunk.ly needs a serious webdesign — someone please help them, they are in need”
• trunk.ly needs a serious web redesign — someone please help them they are in need
• — Suhail Dawood (@suhaildawood) April 7, 2011
• . Still, if we can get funding, employee number one will be a UX designer and hopefully we can resolve this. Technically we’re strong here, the UX could do with some love.
• Competitors “what if Google builds it”? Well, we’ve shown in the last 18 months that we can iterate. 5 products, 4 launched to some degree in the last 18 months and we’ve shown we can iterate and change with the best of them. Sure I worry about a Google or someone muscling in our space, but I know we can iterate and change faster than they can too (size has some advantages).
• Search is very challenging — but it’s improving and will get better with the new release. Still, while some people have occasional issues, it’s good enough for lots of people and we get as many positive as negative comments about it. I don’t lose sleep over it yet (maybe Alex does).
• We know there are scaling challenges ahead, but again, this isn’t a fear — we’ve got a great team, they might hurt when they happen but we can resolve them (and if we get to that point, we’re probably in a better position resource wise to resolve them).
• Money / Funding. But I don’t fear not having money (I do WORRY a lot though!).

Last night I woke up at 3AM in the morning, tossing and turning and unable to get back to sleep. So what was it keeping me awake? Is this the “nightmare” that is my greatest fear?

Turns out that thing I personally fear the most is having to stop. I can deal with the worries — between Alex and I we’ve shown that we can tackle the challenges that this startup journey is throwing at us, we can keep iterating and moving forward, but the thing that keeps me awake at night is the fear that I’ll have to stop doing what I love, and go do something that pays. After 18 months of working with Alex, it’s the fear of NOT working with Alex that is my greatest fear. If startup is a marriage, then my greatest fear is divorce.

Highlights

• Meeting with Rand Fishkin and bouncing ideas with one of our most passionate supporters.
• Catching up with Brian Menzies and Bart Jellema, two of the three people behind Bootup Camp which is where Alex and I met.
• Twitter login finished (but not deployed as it’s now backed up behind the imminent release of the new site).
• Really pleased with the great work produced by an intern who wants to work with us and has completed our programming challenge successfully (which is non-trivial).

Lessons Learnt

• Sometimes we get too focussed on the technical, and don’t spend enough time talking about what we are doing. You can’t be all talk, but at the same time, the best way to hone and refine your message is to say it to real people (with real questions) again and again and again.

Goal this week

• Setup a few meetings for next week.
• Preparation for San Francisco
• Launch the next version of Trunk.ly!