Hacker Hustler Designer

How to hustle like a New Yorker

To aryrow a business you need a steady stream of customers and investors because cash-flow is the lifeblood of an enterprise. Yet lots of people around the world still feel uncomfortable with business development, marketing and pitching to investors.

Hacker Hustler Designer
Alley NYC brings together hackers, hustlers and designers.

In Silicon Valley there is a saying that the perfect combination of skills for a startup is a developer, a designer and a hustler. Often under appreciated, the hustler is responsible for ensuring that the business has a steady and increasing cashflow. The role of the hustler could be taken by someone with training in marketing, sales or finance. The art of the hustle is really just a combination of clear communication and hard work.

Learning to hustle, New York style

During a recent UK startup trip to New York I met lots of startups with a uniquely New York combination of skills. It seems that in NYC the best combination of skills for a startup is just a developer and a designer, because in New York everyone hustles.

The art of the hustle has nothing to do with misleading people like hustling a pool table by being deceptive about your skill level. Instead, the modern art of the hustle is all about sales, business development and a bias for action.

In New York you can’t survive (no matter what your industry) unless you can deliver a short and effective pitch for yourself and your product. New York is so competitive in every field that the ability to communicate and persuade is actually part of every discipline. Gary Vaynerchuk was the first to introduce me to just how important energy, enthusiasm and sheer hard work is to entrepreneurship. He’s a true New Yorker.

I have never met so many developers who were so confident in explaining their product, their go to market strategy and their business model. Nor have I ever met as many designers who were so confident explaining the value of design, the importance that their work held within their company and their role in championing the cause of the user.

Jake Dunlap Skaled
Jake Dunlap from Skaled taught us about how sales and Business Development are different for startups.

While in New York we met Jake Dunlap from Skaled who consults with startups on building a sales function. He’s a consummate hustler, always delivering value to people he meets, so they want more. He taught us a little bit about the different roles that a good sales team can play across the business.


What does a hustler do in a startup?

In London the role of the hustler is to “go get that money” so no one else needs to worry about it (which in practice means that they need to be responsible for marketing and capital raising). In New York, everyone gets involved in hustling and the art of the hustle is used in more diverse areas. Any time that you need to persuade another person to do something, then it’s time to hustle.

Strategy hustle

The strategic role of hustling is to interview customers, understand the marketplace and to engineer behaviour. The hustler isn’t afraid to get out of the building and go talk to potential users of the product. The key strategic function of a hustler is to be able to listen. Understanding a customer’s pain is the most important input into a good startup strategy.

Marketing hustle

The marketing benefit of hustling works across sales, business development, marketing, branding, advertising and public relations. The key part of this is business development because the hustler is responsible for results. They see branding as a way of supporting sales results. A good hustler is surprisingly metrics focussed and they are often very interested in conversion rates, website traffic and margins.

Finance hustle

The finance role of the hustling is to drive capital raising through venture capital, angel investing and seed capital investment. The hustler takes on the job of relationship building with venture capital investors. Investors are often more interested in the team and their relationships than in the product.

In many ways, the art of sales to customers and the art of raising capital from investors are simply about relationships, communication and persuasion. Therefore the hustler is important to both.

Learning to hustle along with your day job

If you are not based in New York then you can still learn the art of the hustle. In the case of developers, it is simply a matter of learning to communicate the value of good development processes and technology. Likewise, for designers, the art of the hustle is about articulating the value of design. Both groups can afford to learn more about how to “always be closing” (ABC) when it comes to social and semi-professional interactions where you can be conveying the value of the business.

When a developer goes to software engineering events, being able to hustle would mean being able to explain why the company is a good place to work and therefore attract other developers. For a designer going to design events, the art of the hustle would mean explaining what new and interesting things the company was doing so that they could attract new design talent.

Culture of hustle

I am very conscious of the need to hustle because I come from New Zealand. In New Zealand we are very apologetic, polite and reluctant to hustle. In fact, it is widely frowned upon in New Zealand business culture. Persuasion, communication and relationship building are all considered low quality and low paid activities that are often delegated to sales support roles.

New Zealand companies often struggle when they go to America to raise investment. New Zealand start-ups are often creative, technical and interesting businesses. But they struggle to raise capital because they are too apologetic and polite about their aspirations. The American investor wants to hear a good story, well told, quickly.

Only a determined hustler is able to persuade, communicate and build relationships quickly and effectively. In large law firms and professional service firms there is a long-standing idea of becoming a rain-maker. The rain-maker takes on the art of the hustle, but also maintains their core deliverable within the business; for example, continues to be a lawyer or accountant.

Hustling the network

At a networking event, hustling does not mean being the annoying salesperson who thrusts their business card into your hand and runs off. Instead, a true hustler will research and identify who their high priority targets are for the evening. They will then find those people and spend quality time building real rapport. If you find yourself in a conversation with a real hustler you will notice that they are 100% concentrating on the conversation with you. If you notice your conversation partner looking over your shoulder, it means that they are not a real hustler.

Klaus Bravenboer from FuelStory (also part of the Converge Collective) was on the trip to New York and found that follow up is the most important part of hustling in New York. If you meet someone in New York then you need to follow up within 24 hours to keep the contact alive. Klaus also noticed that you need to get other people’s business cards so that you can take responsibility for follow up, rather than handing out your card and leaving it to chance,

Brian Frumberg VentureOutNY
Brian Frumberg has bought together a diverse network to support VenutreOutNY.

In New York we were hosted by a true hustler. Brian Frumberg is the founder of VentureOutNY and an entrepreneur at large with DFJ Gotham. He has built real relationships throughout the New York startup community by making mutually valuable introductions and genuinely caring about people. Brian is a good networker but his main point of difference is that he works really, really hard.

Another participant on the tour was Ian Randolph from Prepict who is a New Yorker by heart. His conclusion from our tour was that no matter what your job description, everyone has to be a hustler. In the startup environment, there is no way to avoid the importance of relationships, communication and getting things done.

Learning to hustle

Anyone can learn the art of the hustle. My first recommendation would be to spend time in New York, the quality of communication and persuasion in New York is extremely high. Simply log on to meetup.com and go to networking events in your industry. If you can’t travel to New York then you can still go to more networking events, use these to practice describing your business and your role within it. You can also read “Crush It” by Gary Vaynerchuk and the old classic “How to Win Friends and Influence People” by Dale Carnegie.

The best way I have found to get better at hustling is to get out and do it more. Agree to go on sales visits with your sales team and try and arrange speaking engagements that force you to distil and communicate the essence of what you do. For me, the key to being a great hustler is to be open, honest, clear and direct.

4 thoughts on “How to hustle like a New Yorker”

  1. Inspiring article Pete – would argue quite strongly though that you could swap the word ‘investors’ out for ‘cash flow’ in the first sentence!

    1. Good point. – Spoken like a born hustler. You’re right that cash flow can come from multiple sources, but customers and investors are still the main ones. In accounting terms cash flow is going to be classed as either debt, equity or revenue. My favourite (as I’m guessing yours is also) is revenue.

    1. Yep, the combination of “make it work”, “make it usable” and “make it make money” is pretty powerful. Design, Business and Technology is at the heart of shy we started the Converge Collective. And Alley NYC has a pretty good Hacker, Hustler, Hipster summary on their website.

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