Start It Up

Tom Jacobs
6 min readJul 18, 2015

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Over the course of my startup career, I’ve been lucky enough to have been taken under the wing of three different world class entrepreneurs.

My first ever job was working at Red Swoosh, Travis Kalanick’s startup before Uber. As a kid just out of college and moving to the U.S. to be part of the startup community, that ended up being a pretty good place to jump in. Working with Travis, I learned the importance of the hustle, and that the code wasn’t everything. I was a developer, so at that point, I didn’t care about any part of it that didn’t involve writing code. I had been writing software since high school, and had worked out that there was some connection from being able to make computers do what you want to being able to make a living from it, but I hadn’t worked out what that was yet, without just working a day job. That missing connection was the hustle. Figuring out what different groups of people want and need and letting them know that you have it or can build it. Hustle.

The next founder to take me under a wing and teach me a key piece of the startup game was David Barrett, CEO of Expensify. David gave me a front row seat on how to build a product. I headed up the development of the Expensify mobile apps, learning the importance of making something the best at solving a particular need in the world. We went from a theory that people would use a great app personally and then introduce it into their work life, to having a mobile and web app product used by employees at different businesses across the world, making them so much happier in their jobs. Product.

Back in Melbourne Australia building an army of Raspberry Pi WiFi sensors at Kepler, CEO David Mah has taught me the last piece of the puzzle: vision. Constructed from a careful combination of idea filtering, trend analysis, market research, and planning, vision is an important one to understand when running a startup. Also interesting to learn is seeing how fundraising gets done — coffee meetings. David raised over a $1 million in angel round funding for startups here, which is a feat in Australia. Vision.

Hustle, product, vision. I couldn’t think of a more perfect trifecta to learn in the startup world.

So I’d like to share a few things that others have taught me, a few things that I’ve seen that work along the way, and a few things that I’ve come to understand from starting businesses of my own.

Be the best
When deciding what your startup should be, find the area where you can be the best. No one cares about something that is pretty good. No one raves and tells their friends about the thing that gets the job done pretty well.

People want the best. The best website designer, the best video creator, the best app marketer. Especially if their business is at stake, they don’t want good enough. All else being equal, they’re going to use the best thing. So don’t go into that food delivery business, don’t go into that social network management space, unless you have the ability to care every day to make all the people who use your service rave about it, with how they think it’s better than any other way of doing it. If your competitors could make their product better for free, they would. You’re all going to make it the best you can. So find the particular unfair advantage that you have that your competitors can’t get to.

There’s opportunity everywhere, so long as you’re the best at it. So find the thing you are able to spend time crafting and caring about when it’s not perfect, for the sake of the people who ultimately make or break your startup: your customers. If you can’t see yourself hand delivering those tacos at 9pm or calling your 50th client on a Saturday to go through how their Instagram feed could get more followers, don’t bother. Find the secret that makes it easy for you. Find the thing that only you have the access to that allows you to just provide a better service. Technology, people, time, skill, geography, insight, experience; whatever it is, understand it, and understand how you could possibly scale it in the future. There might be a secret that is unique to your personality and situation, that you can take, teach, and replicate.

Another way to be the best is to be the only; if there truly is not comparable competition, you’re the best. This is rare. And doesn’t last long.

So now that you’re offering the best product or service, what else should you do to get it out there, perfect and scale it?

Learn as much about your area as fast as possible
No one runs the best digital content business, the best home cleaning business, the best dog walking business, the best app marketing business, at any scale, if they don’t intimately know the small intricacies of behaviour of the people who use these services. I love the story of Adeora Chung of Homejoy who not only took courses on how to clean homes to understand it better, but used gathered data to research what gave the best indication for determining which cleaners will have the highest customer satisfaction.

Talk to customers, feel their pain
You can’t sell something people don’t want or don’t need, just because it’s nifty. You have to see what pains them. And see if there are more like that.

Give them their dream, not yours
People have somewhat of an idea about what they want. Sometimes a lot of other people have similar enough wants. You have thoughts on what would be cool, but you’re going to most successful when what you’re offering meshes with that group want, rather than just giving them your brilliant idea.

Be curious
Curiosity is an underrated characteristic in a founder; it’s is just the vehicle you use to naturally improve your product by asking why users are doing what they are doing, and steering into that.

Be obsessive
You have to get past the mindset of a consumer and into the person behind the curtain making the product. Once you get the understanding that there’s always so much more happening behind the scenes for a product than the consumer sees, and that a product is often just a carefully curated, trusted package of some raw previously unconnected parts, you begin to see how much needs to be done to make something appear simple and great.

Be realistic
You should draw on your past experience of what actually ended up happening in situations where you previously were going to change the world with a great new idea. Couldn’t get anyone actually using the thing? That’s the constant struggle startups face; that no one actually cares.

Be smart
I think you can be smarter just by sitting and thinking about things for a few more minutes in different ways, like how you can be more creative by just sitting with the problem a little longer.

Lean the product into emergent user behaviour
Reddit and Facebook are famous for observing what users do, and making their product easier to do those things. Twitter is the opposite here, where they try to dictate an experience for users. Either way can work, but users are generally more happy when the product does what they want, even if they don’t admit to actually wanting it.

Design the product for user emotional feeling over technical coolness
Wouldn’t it be cool if you could do this in a browser? The user doesn’t care. Wouldn’t it be cool if this thing that the user does every day was just done for them and they didn’t even have to open their browser? The user loves it.

Design it to be used conspicuously in public, and privately initially
A lot of people want to look like they’re the best at discovering and sharing great new things, that they’re the trendsetters, but no one wants to look the fool. So people need to be able to try out the full experience of a new thing by themselves first, to see if it’s good or not, and then once they’ve been through the whole experience of it, then they can become a public advocate.

Seek what you want to spend your days on
And lastly, don’t seek big success. Opportunity is everywhere in areas that you can be the best in, so seek what you want to be the expert in, accept that you’re not currently the best in the world at it, have no ego in how good you are at it, absorb all learning about that area, think about it non-stop, and you can become great at it through enjoying being obsessed with learning about it. Enjoy the learning.

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