Tips on dating a Suit

I want a man who is kind and understanding. Is that too much to ask of a millionaire?’

Zsa Zsa Gabor

Life is unfair.

Why do Fintech firms who have the leading technology solutions, boundless energy and real customer insights struggle for capital, clients and cashflow, whilst bloated legacy firms with 20th century technology, massive inertia and low-energy people still make bonus and vest share options?

Disruptive models will ultimately prevail, but how long that process will take is uncertain. Inertia is a particularly powerful force in financial services.

For a Fintech the reality is that you have to be right for quite a long time to be successful. For a legacy firm you can also be wrong for a very long time and still survive. Remember even in the road-runner cartoons, the coyote was able to take a few extra strides even when he was over the edge of the cliff!

Let me introduce myself. I was a suit (with a tie) for about 30 years. I ran several businesses of substance both in Ireland and internationally. For the past 6 months since I left corporate life, I have ditched the tie, and am now down to wearing a suit 2/3-days a week. My therapist says I am thawing but am not yet chilled (which is better than being burnt out).

Having reached the stage of personal independence I decided to look over the fence and see what life was like on the other side. It’s been a revelation – I genuinely never knew there was so much going on in the tech scene in Ireland.

For many senior executives; the corporate owner sets the treadmill at such a pace you don’t have time to see anything around you. Imagine the frustration of running on that treadmill all week only to find at 6pm on a Friday you are still in exactly the same spot as you started even though you are drenched in sweat. Welcome to my (former) world.

On leaving the corporate world, I decided to take an MBA programme from the University of Life. For me that meant a complete change by working with Fintech’s and other technology firms on how to scale their businesses.

The thing I have learnt the most is how little I know about API’s, biometrics and blockchain. It’s been energising working with brilliant people who have such boundless optimism. I never realised that Ireland has such a vibrant start-up scene.

However, the other thing I have learnt is that it is very hard for many Fintech’s to survive without active collaboration with legacy firms, particularly for those with B2B solutions. As unfair as it seems, the legacy firms are still the ones with all the customers and capital – that vital fuel Fintech’s need to scale and develop.

In any relationship you need a spark, and for Fintech’s and Legacy firms that spark is a shared love of the customer. The Suits and their colleagues have developed real human relationships with their clients over many years and regularly go the extra yard to deliver. Their current solutions may not be leading-edge like yours, but don’t ever doubt their commitment to their customers.

Growing up I went to an all-boys school which meant I never really got to understand women until I was about 28 (I got married at 25!). I feel the same is true of the Fintech community when dealing with suits. For such bright and insightful people, you need to update your dating skills. Many of you are doing it all wrong.

What do I mean? At the risk of sounding like an agony aunt, here is some basic advice when trying to get a suit to buy your solution;

  • Go hunting for a Whale: By and large the higher up the first person you meet in a legacy organisation the better chance you have of success. Most likely the person who can write the cheque will be in the Business and not in IT. Figure out who you need to talk to and use your network to get an introduction. Take your time and you will get there quicker.
  • Chat them up: Take time to get to know them and their world. As a suit, the best 1st meeting I ever had with a Tech firm was when they put their powerpoint to one side and spent the first 20 minutes asking me about my current issues and concerns. If you listen properly, the opportunity will likely present itself. Suits love talking about themselves – at the very least it will put him / her in a good mood.
  • Ditch the Tech talk: On an early date talking about you and your technology is a complete turn-off. The suit is just not interested. What he or she is interested in is what you can do for their business. Talk solutions and their eyes will sparkle.
  • Aim low: your chances of selling an enterprise-wide solution on a first date is almost zero, they’re just not that kind of suit. Instead try to find one problem or issue you can fix or improve in a 6/8 week window. Success will get you a second date and aiming low might just be enough to avoid a formal procurement process.

Believe it or not suits are simple souls at heart. Find out what is important to them and help them sweat less on that treadmill and they will become your friends.

Gerry Hassett is a former suit who now helps ambitious firms to scale in a mentor / advisor / investor capacity. Find out more at