Startups are businesses. Why do some people seem to forget that? Especially the people running them.

Not just ordinary businesses, but business at the hardest point in any journey; the start; where every minute, every hour, every day is valuable and irretrievable when wasted. Where every decision has consequences, where resources are extremely limited and where even if everything goes your way and luck is on your side, you probably still have, at very best, a 1 in 10 chance of success.

Lately, something has been worrying me. In the past few years, we’ve created, supported and facilitated the growth of an ‘entrepreneurism industry’ in Ireland that doesn’t give a damn about building successful businesses; how could they? They have no ideas what the measures of success are, they have no experience of building businesses, disrupting industries or creating businesses that will change the world. The majority of them have barely left their offices in a decade. Consultants flourish in this environment, but 99% of them are people with no relevant experience of building modern, high potential, high growth startups.

The biggest problem with this ‘industry’ is that it creates doubt and lack of confidence in new entrepreneurs ; who instead of trusting their gut and just going for it, wait around looking for others to validate their decisions and actions, looking for the right answers that often aren’t there. There are often no right answers when it comes to building a brand new business.

But what’s very scary is that we seem to have lost that core value that every entrepreneur has in common; a great work ethic. Instead of imitating the successes of leaders who’ve made it; like Pat Phelan, Colm Lyon, Jerry Kenneally, Brian Caulfield, Mark Little, Peter Coppinger and Dan Mackey, Ray Nolan, and many, many, many others; who all have basically one thing in common – they worked their asses off, every minute of every day until the got success and even then they just moved the bar higher and kept going; we look for easy solutions, quick wins. We look for every option apart from the one that’s so obvious and right in front of us – work harder and stop looking for easy answers from other people.

The easy road traveled never leads to a place no-one’s ever been before. And that’s where startups are meant to head, into the unknown. Successful entrepreneurs use every minute they have to advance their business. They don’t perform for others. They don’t waste time on trivialities. They focus on the next milestone, the next goal, the next thing that needs to be done in order to get even a fraction of an inch closer to the goal.  We’ve allowed Entrepreneurism to become a lifestyle and it has to stop.

Dedicated startup founders are not reality TV show contestants and don’t act like they are. Let’s face it, if entrepreneurism really was actually easy, wouldn’t everyone be doing it?

We were bricking it.

It was the final of Startup Battlefield, the highlight of Techcrunch Disrupt New York, the world’s toughest pitching competition. Four long days of preparation, working on slides, owning our numbers, researching the judges, trying to guess what sort of questions they’d throw our way, technical rehearsal, after technical rehearsal, with little or no time for sleep. The fact that we had even made the competition was national news at home in Ireland so the pressure was intense. The well wishes on Twitter, the emails of support and the crazy amount of support, led by chief cheerleader Karl Aherne, sitting in the front row were massively appreciated but added to the already crazy levels of pressure. But we were ready.

And now here we were, backstage, waiting for our call, when Pat Phelan would take to the stage and compress everything over the last month’s work into three short minutes that could make or break Trustev forever. In the audience were VCs and investors from every major venture fund on the planet, as well as at least 100 tech journalists from all the top publications. Also present were all the potential customers that we had spoken to over the past few days; some of the world’s biggest companies whose interest had been peaked and now wanted to see what we were made of.  Waiting to judge us was a panel of heavyweights; including new CEO of Yahoo, Marisa Mayer, no token judges, or sponsor’s representatives, just five industry leaders waiting to shred us to the bone. If it was a sport, it would have been as brutal as the UFC.

But that was then.

The era of the pitch competition is over, I’m calling it.

Times change and things get old. The real value in startup pitch competitions is gone and now they are nothing but a terribly destructive distraction for startups who should be 100% focussed on survival and growth – this means spending very waking moment they can spare talking to customers, not performing in dog and pony shows.

In the golden age of startup pitching, it was in rooms full of valuable investors, not make-believe investors or self-important egotistic investors who happened to have left their cheque books at home, actual people who could change your startup’s fate forever. They were packed to the hilt with media and freelance journalists looking for the next great startup story.  The winners would take home not just a substantial prize, usually a $50,000 or $100,000 convertible note investment from a sponsoring VC firm. But actually, the prize was irrelevant because victory usually meant a slew of investment offers from firms in the audience. For the winners, the opportunities were endless and even making the final was a substantial achievement that would help with future fundraising efforts.

But now it’s over. Too many competitions, too little value. Now that startup pitch competitions have gone mainstream, all the value has been removed from the large majority of them. They’ve become nonsensical performance pieces more resembling Dragon’s Den or Shark Tank than the actual pitch format that entrepreneurs experience when put in front of actual investors. They’re a perfect way to fill some empty time on a conference schedule. Organisers, please remember that Startups are businesses, please treat them that way. There is no value for them in making them dance for your entertainment. Promising them ‘exposure’ is the same crap that unpaid interns are fed. And please for the love of god, at the very least try to have a judging panel that is actually qualified to judge the startup’s unique business models, by including people who have actually built successful startups.

For Startups, remember there is no surer way to destroy your reputation that wasting time at events that serve no benefit for your business. Stop entertaining others according to their rules for no value whatsoever. The next time that you’re asked to take part in a startup pitch competition, at the very, very least ask what specific investors will be in the room and what the media opportunities for your business are.

Stop performing, just focus on your business.

Risk taking is part of being an entrepreneur, in fact I rate it as the defining characteristic of being an entrepreneur because its usually the paralysis from fear of the unknown that stops people from becoming entrepreneurs in the first place.

But for some reason we now live in a era that celebrates the cult of failure, where individuals who fail repeatedly are still held up as people to learn from. We’ve created an easy route out of difficult decision making and rough times because we’ve made failure easy.

In the past year we’ve lost some great businesses and ideas from individuals that I greatly respect. In the majority of these cases I have no personal worries for the individuals involved because the character they’ve shown as they shut down their companies and moved on, shows that they really understood the consequences of what they were doing. They had made mistakes, learned from them and they’ll be back, stronger, faster and smarter than ever.

On the other hand, moving from one failed idea to another and just repeating the same mistakes – we’ve had plenty of those too. Startup junkies of the worst kind, those addicted to the startup lifestyle, people who have pivoted so many times, are they even back where they started, those determied to retain their CEO title without understanding for one second what it means.

There’s a big difference between making a wrong call in a planned experiement and it not going to plan and actually failing because you had no plan. Yes, the biggest risk of all is taking no risks but only if those risks are planned and measured. Failure should always be the worst possible outcome, something that you avoid at all costs, something that happens only after you’ve exhausted all options, failure should (and does) cut into your soul and take a piece of you with it.

How do you know when you’re really failing? The really really serious kind? Well look at the core of your business, if that’s whats failing then you’re in very serious trouble. If your product isnt engaging with customers, if they dont seem to understand how great it is, they dont want to pay what you want them to pay – those are all life ending problems to be handled immediately.

Ask any good entrepreneur what their three biggest failures are and there’ll be no hesitation in them listening them off, they live with them every day and will never forget the hard lessons learned. They are battle scars that shape every decison and action they take going forward.

So avoid failure, embrace success and when stuff goes wrong, pick yourself up. learn from it and try again. Learning from mistakes is great, celebrating failure is not.

Failure always has consequences.

A lot of first-time founders and startups are going out to raise money these days. It’s pretty hostile territory at the moment.

And they usually start off awful, I mean really, really, really bad. Their only experience of this kind of finance is usually limited to their own personal finance stuff – applying for mortgages, car loans, personal loans etc.

Let’s get one thing straight before we start – A VC has as much in common with a Bank Manager as Sex in the City has with the Die Hard movies! (I feel like we should have a deeper discussion about that comparison at some point!).

A bank manager (and their process) is built for as close to 100% risk avoidance as they can manage. They want to lend you money, earn as much interest as they can over the duration and then once you’ve paid back, if it’s been a good deal, they’ll probably try and lend you more.

On the most basic level, raising money from VC’s is far more akin to taking on a new business partner in the business. A great VC is your new wingman, having your back, while introducing you to new opportunities, talking you up at every opportunity.

Never forget: it’s in every VCs interest for your business to grow, the more you grow, the more their investment in you is worth.

(1). Remember where the money is coming from.

Despite the snazzy dress sense of Dublin VC socialites such as Will Prendergast, Conor Stanley and Ian Lucey please, please, please remember that the money you’re seeking is coming from a fund, not completely from the VC partner’s pockets, a fund that just like your current efforts, someone had to go out knocking on doors to raise. And just like the expectations placed on you to deliver a return if you take their money, the VC partners have to deliver a return to their investors or they’re out of business and back to buying their clothes in Pennys.

So keep in mind a few things.

(a). They’ll invest primarily in areas that they know and understand best. Their knowledge of an industry will help them make their own predictions on success and they’ll be most comfortable working in areas that they don’t need to go out and learn about. So stick to pitching VC’s that have history in your space. If they don’t have a track record in your space then help yourself out by including extensive industry space information in your pitch – help them understand what success will look like in your industry space.

(b). The bigger the fund, the bigger the expectations. Everyone loves having a ‘household name’ fund as an investor but for most of the big funds anything less than a $100m exit will be considered a very poor use of investment capital. Be very clear about expectations, how big do you see the business getting and how does that relate to other companies in the fund’s portfolio.

(c). Human nature states that how far they are into the lifecycle of their fund will dictate their current approach to risk. If their fund is maturing then you can be damn sure that they’ll be starting to think hard about how they’re going to return to their investors so they will be far more likely to use remaining funds to double down on existing investments, than take on new ones.

(2). It’s a Partnership, stupid!

Here’s where most first time founders go wrong. They think that once the fundraising process comes to an end and the cheque clears, they go their separate ways, with the occasional update to keep the investors happy.

With investors, if you’re doing it right, you share openly all news, good news, bad news, you frequently ask for help (see below), you keep very open, very regular channels of communication with your investors and that way there’s no panic and no surprises. The absolute master of investor relations is Pat Phelan, my former chief at Trustev.

If you try to hide stuff from investors, they’ll find out. Remember they’re usually among the most connected people in any ecosystem and they’ll hear rumours, whispers, all the gossip, everything – if they’re on your side, they’re your best defence. If they hear something that you should have told them, expect it to become a major problem.

Remember investors are trying to manage a portfolio of dozens, sometimes hundreds of investments. The more open and transparent your chain of communication with them, the more likely it’s going to be a good relationship as you’re saving them a huge amount of work in keeping track of you.

(3). These guys are smart, very, very, very smart.

So when a VC asks for a business plan, financial projections or other documentation, in my experience, it’s usually more so that they can judge how fiscally responsible you are, how you are at managing money and how good you are at reporting than believing the actual numbers that you show them.

Even when discussing spaces that aren’t in their field of expertise, most VCs grasp the principles very quickly so they can be a huge resource for any CEO in being an independent, but still connected sounding block on pretty much any issue. Their perspective is usually fairly binary – good for the company or bad for the company, so it can often be incredibly helpful.

(4). You cannot ‘fool’ an investor out of money.

Due diligence – two words hated by every entrepreneur because it’s where all the problems start if you’ve been ‘fluffing’ or padding anything. A deal is on the table and then the deep digging starts. The books are opened, the technology and code are opened to experts, every single thing comes out in the wash, every number gets examined and all it takes is one lie or one exaggerated number and the house of cards falls over and you’ve burnt that bridge forever.

(5). Please remember Dragon’s Den and Shark Tank are entertainment shows.

This one is a bit tongue in cheek but with an important underlying message – fundraising is an exceptionally complicated process – legally, financially and psychologically – it takes months, not weeks. The deal has to work for everyone, investor and startup and nothing is done or certain, until everything is done and certain.

(6). Learn everything you can about their business.

If you want a real hands on (eyes on?) look at the sort of stuff that goes down during a fundraising process, I’d recommend reading up on how Rand Fiskin and Moz handled themselves during their fundraising adventures. First up is Rand’s extremely detailed guide on Moz (then SEOMoz)’s Venture Capital Process.

Then read, “What I l Learned About Sales But Foolishly Forgot When Raising VC” which points out the obvious, the process will be so much easier if you’ve focussed on a product and built your business so that it’s attracting interest.

Then read the brilliant “Misadventures in VC Funding: The $24 Million Moz almost raised” where Rand prints the actual email exchanges back and forth between him and potential investors. A mentor of Rand’s and cofounder and CTO of Hubspot, Dharmesh Shah, wrote this great public post with various bits of advice for Rand that are just pure gold.

I’d also recommend two great books – Brad Feld’s Venture Deals and The Art of Startup Fundraising by Alejandro Cremades as two essential pieces of reading.


The world of VC finance is challenging at the moment. Global economic uncertainty is having multiple effects on the funding environment for LPs and VC funds, which trickles down to startup funding.

So never underestimate the time it’s going to take to close a successful fundraising process, its always going to be measured in months, not weeks. And even once investment is agreed, dont start spending yet, as the time between an agreed investment and funds being in a bank account usually surprises everyone.

Update: The Guys at Atlantic 302 did an episode talking about the contents of this post (which is awesome… the podcast… not the post…. this isn’t a humblebrag…. I promise…)

It feels like sometimes the key failure in current policy towards developing a proper, fully functioning entrepreneur ecosystem in Ireland is pretty much based on the current assumption by the government and related parties that entrepreneurs are morons.

Entrepreneurs aren’t dumb (well most aren’t) so those who want to start their own business don’t need to be treated with kid gloves. They’re among the most capable of us, they find a path in the chaos, they find innovative ways to get stuff done. Point them vaguely in the right direction and they’ll find their way. Tell them to drive from Dublin to Galway and you don’t need to hand them a map or even car keys, they’ll find the way, someway, somehow.

In the minds of our government and local officials, every entrepreneur needs to be led by the hand through the entire process of starting a business from start to finish. We focus the limited resources our country has on a system that seems to replicate our national driving license setup; you get some lessons (mentors), fill in some paperwork (oh so much paperwork), take a test (judgment from a panel/board/etc) and then hey presto, congratulations! Here’s your entrepreneur license!

And then we wonder why we’re not creating more businesses with truly visionary ideas.

We put entrepreneurs, our best and brightest, some of the smartest and most energetic people our country has to offer, usually people with tremendously risky ideas, in front of, usually well intentioned, people whose very jobs are dependent on taking no risks and we expect them to have meaningful and productive conversations.

Yet what we’re doing in Ireland is creating a support system that cradles entrepreneurs inside a protective bubble instead of creating a dynamic environment and market in Ireland that supports entrepreneurs, whether or not they choose to engage with the support mechanisms of the state. We’ve created an advice economy where talk is valued over action, where drowning in paperwork is the number one* cause of death of most new businesses (* may be a made up statistic).

We need a modern system that creates a positive relationship between entrepreneurs and the systems of the state. We need policies that create a market in which entrepreneurs thrive and are the envy of their peers in other countries, not because of the handouts, but because of the hand up!

What do we need in Ireland? Well here’s some ideas to start, additions and suggestions are more than encourged in the comments;

(1). We need a system that creates learning from those who have actually been there.

Government and state bodies, STOP, stop now! Stop legitimizing the horrific ‘mentor’ culture that you’re financing! Stop putting people who’ve never jumped out of an airplane in charge of teaching people how to jump out of airplanes.

Stop supporting an industry that gets paid to give horrifically bad advice on topics that they know nothing about. In a world where ‘business best practice’ changes on an hourly basis, the only people qualified to give advice are those operating in it. Those learning from books entitled “How to be a consultant” need to stay far away from our startups. Create real conversations and real learning networks by bringing together entry-level entrepreneurs, with actual successful entrepreneurs, not ones who are just successful because their twitter bio says so.

Basically stop paying people to ‘mentor’! When did mentor become more a verb than a description of an individual? Entrepreneurs who’ve been there will help other entrepreneurs because of the bond that exists between those who’ve chosen the world’s toughest profession. Stop outsourcing the transfer of knowledge between generations of Irish entrepreneurs and instead focus on it as a priority.

Solution: We need more one-on-one communication between entrepreneurs who’ve been there and entrepreneurs that are trying to get there. What we need is better described as coaching, or even better described as, what we actually do, it’s called “getting a cup of coffee”. Buy 500 pre-paid credit cards with €100 credit on them and give them to successful entrepreneurs to pay for said cups of coffee, best money the government could ever spend. Job done. Ok, that’s massively simplifying the issue but the principle is sound – facilitate more discussions between those who have done and those who are just starting to do, and keep those who talk as if they’ve done, but in reality are just all talk, away from and out of the discussions.

(2). We need a system that encourages risky behavior.

That’s something that’s very tough for the employees of government or semi-state bodies to get their head around. In pretty much every other aspect of government, everything you’re ever taught is to avoid risk, embrace certainty and back the ideas with guaranteed outcomes.

There is no roadmap to success when you’re an entrepreneur, no safe, secure path and by discouraging entrepreneurs from taking risks we’re paralyzing them when it comes to the hard decisions.

Take the holy bible requirement of most government programs and supports, the all hallowed business plan; the playbook for a successful business. Anyone who tells you that you can predict the first three years of any startup business to the point of documentation is one thing and one thing only – a liar. The greatest and most masochistic piece of fiction since ’50 Shades of Grey’ your average startup business plan is designed with one thing in mind, giving validity and backup to whatever metrics and KPIs the reader and decision maker needs. Believing that a startup’s business plan represents a true picture of the future of their business is like believing that a program for government document is what will be delivered over a term of government.

Solution: We need a set of success metrics for government and state bodies that recognizes that sometimes the right decision is also the riskiest one. We need an understanding that taking the ‘safe route’ usually results in the entrepreneurial equivalent of a thousand papercuts, stopping them from taking the leap of faith that crosses the canyon and helps them arrive at the promised land of profitability. Let’s revise metrics to focus on the number of businesses started and then the success rate of those businesses, as opposed to the unrealistic obsession of jobs created.

(3). We need a system that recognizes the lack of global borders.

We don’t live in a world of 26 counties, we live in a world of 196 countries.

Firstly, when a company in Ireland launches, from day one they can, and often are, a global business. The idea that you crack the Cork market, then the Dublin market, then the Irish market, then the UK… oh fuck, we’ve run out of money! Business just isn’t that linear anymore. For most new businesses, the Irish market is simply too small to allow them to create the sort of breakthrough growth velocity to successfully make it into orbit, they have to take advantage of technology and get things growing internationally from day one.

Secondly, often startups need to hire key people from overseas, they need those people with very specific skills, at a particular experience level that our education system hasn’t delivered yet. Our third level institutions have reacted well to the skills shortage, but in some areas if you need someone with 5-10 years practical experience in a certain field, there may still be a need to recruit from overseas.

(On a side note, I do think that third level colleges would benefit greatly from more interactions with newer technology companies before setting syllabus and delivering technical courses. Many of the software languages and skills being taught may be relevant for older technology companies but are wide off the mark when it comes to the more modern company that most graduates will be drawn to).

We need to be able to easily facilitate these key hires to come to Ireland and work with the minimum of paperwork. I think Irish people will always have a bias to hire Irish people so when they need to hire an overseas hire, there’s usually a key reason why and we need to stop being a country that makes it overly difficult to do so.

Probably of most importance, from a policy perspective, is that the government needs to realize just how mobile startups are. Look at some of the countries often lauded success stories, people like Stripe and Intercom, both of whom it just so happens are US companies. It’s becoming increasingly easy for companies to bypass Ireland entirely and set up as US or UK companies so the government needs to realize that there is competition for where ‘Irish’ businesses actually set up in the first place.

Solution: We need to pay very close attention to what incentives other countries are putting into place to support startup companies. We used to be leaders in this space in Europe, but now we’re very much behind the times.

(4). We need a system that encourages employment.

Startups are nothing without their people. Sadly, probably one of the hardest things to do when a new business is getting started is to hire that first employee. It’s the moment when everything changes and where the risk all becomes very real for a first-time entrepreneur as now they’re responsible for someone’s livelihood apart from their own.

Hiring and the decision to hire is usually based around certainty of cash flow, the most important words in the English language for new entrepreneurs. So anything that we can do to assist them in this regard has a huge impact, whether it be a reduction in the cost of hiring that employee through reduced taxes or even direct subsidies, will have a huge effect on the number of people employed by our small businesses and might create the sort of growth conditions that allow a fledgling business to become self-sustaining.

Solution: We need to cut new businesses a break when it comes to taking on those first few critical employees. Austria recently introduced a system where any startup is relieved of the burden of having to pay auxiliary wage costs for the first three employees of during the first three years in business. It’s usually not the salary costs that make hiring hard, it’s all the associated costs, if the government could give a break for a year or two on some of these costs it would really encourage

(5). We need a system that prioritizes speed.

How do startups survive long enough to gain a market foothold in a world where every market has giant juggernauts trying to crush them? Easy – speed and agility, they can move so much faster than their corporate competitors.

It has often been described to me like a sprinter racing a hurdler on the same track, the sprinter has a clear advantage and can even take having to leap over the odd hurdle. But keep putting more and more hurdles in their way and eventually, they’ll come crashing down to earth.

Solution: Everything about our system needs to be designed for speed, we need 10 day, 21 day, 30 day guaranteed turnarounds for anything that involves interaction between a new business and a state body.

(6). We need a system to limit the middlemen.

I’m a huge fan and supporter of Enterprise Ireland and the work they do, however, they’re not without an issue or two, purely because of their size and status as a semi-state body, which isn’t really their fault.

You can’t operate a semi-state VC fund without huge difficulties, the very nature of investing in risky, innovative businesses isn’t very compatible with the responsibilities of managing public funds. So Enterprise Ireland are in a very difficult situation, their desire to provide funding to new and innovative businesses are tempered and limited by the need to be publically accountable for all funding. Let’s face it, if an Irish company is the first one to create transporter technology from Star Trek, it’s a huge bet for EI to take. Success means acclaim, failure means intense media questions around ‘irresponsible funding practices’.

EI’s exposure to so many Irish companies also brings with it a huge amount of knowledge which they could be better sharing through increased and more specialized training and networking activities. The experiences and expertise of some within Enterprise Ireland could be better harnessed than making them act as defacto loan officers.

Solution: Start by taking a small % of the money that’s going to these bodies and use it to finance direct support for entrepreneurs in the form of tax and employment incentives. Eliminate the absolute reliance on EI for direct funding of startups and let them focus on other areas that they do great at, like training and upskilling. We also need to encourage more diversity within the hiring in Enterprise Ireland, by trying to bring more experienced people from industry into their ranks.

(7). We need a system that recognizes that age no longer equates to experience.

Calm down, this isn’t a pot shot at the grey haired, just the simple reality that in this face paced, ever changing era of modern business, age no longer automatically equals experience. Some skills and instincts improve with age and the expert knowledge that many of our ‘more senior’ entrepreneurs and business leaders can provide in certain areas is invaluable.

However, 25 years of selling anything on the international markets only gets you so far when it comes to the huge changes in selling, distribution and marketing over the past two years alone. How business is done evolves on a near daily basis and an entrepreneur’s ability to react to that is now completely independent of age.

Solution: This one’s easy, we just need to listen. We need to stop assuming that youth means inexperience. When it comes to technologies like VR and products like SnapChat and Pokemon Go, who would you rather get your information from?

(8). We need a system that recognizes that startups are a team sport.

When traditional SME’s and business go well, they usually have one winner – the owners, so we have a capital gains tax system that recognizes that. Trouble is that in startups, the team usually wins (and loses) as a team and their remuneration packages are designed to reflect that fact. Early startup employees usually have a stock option as a significant part of their packages.

Compared to other countries, the Irish system when it comes to handling stock grants to employees is very difficult, not deliberately, it’s just the legacy of a time where only company directors and very, very senior employees were stockholders.

Solution: We need a manageable legal and tax system to allow for the sort of stock grants for your ordinary employees that are a standard part of the remuneration package in startups.

(9). We need a system that makes investing a profitable and positive thing.

Tax incentives – are they the dirtiest words in Irish politics? It often feels like this is something that’s going to be part of the Irish genetic memory for all times.

Here’s the simple facts – Someone has to provide the capital for innovation to happen, for new businesses to be built. It can continue to be our state bodies like Enterprise Ireland or we can create the space for the market to generate the investment capital.

Our current system just doesn’t recognize or reward the risks that investors take when they chose to invest in startups and SMEs. So few successful exits means that many investors, wipe their brows and consider themselves lucky just to get their initial investment back.

Solution: We need a proper tax incentive for investment in startups and small business. We need an incentive that recognizes the tremendous risk that the investor is taking with their hard earned money in backing a high risk proposition. In fact we need to minimize the total risk for them, while making a successful outcome attractive for them. So firstly how about a tax incentive tied to capital invested against an eventual payout? (invest 100K and the first 100K returned in the case of a successful exit or sale is tax exempt), the government will still make its pound of flesh on the balance of the payout but it encourages investors to place larger bets in the hope of a larger tax free amount. Secondly we need some element of protection for the investor, if the whole business goes belly up within two years of formation, we should let the investor take a tax break of at least 50% of their investment. They still hurt, but when making the investment decision in the first place it helps mitigate the potential risk.

(10). We need a system that recognizes the hard work and sacrifice of our entrepreneurs.

When entrepreneurs take on the huge risks associated with starting a business, a business that benefits the wider economy in terms of jobs, taxes and exports, surely they’re entitled to an expectation of a system that will do its best to support them and not just constantly put up roadblocks in their way? Life as an entrepreneur is pretty tough, low or often no income, long crazy hours, zero work life balance, betting everything on red or black with often a single spin of the wheel. That’s the life they choose, but when the bet pays off, everyone wins.

Primarily, from a government perspective, we need to look very differentially at different levels of entrepreneurs and stop pretending that everyone is a captain of industry who’s just looking for another tax break. We need to support entrepreneurs with policy action to create an environment that makes their lives just a little bit easier. We need to minimize the red tape and always bias for action over talk.


ln developing policy in this area, we need to do a long hard analysis of the risks, and then see if there are simple solutions to help reduce the risk, or share the burden. We need a fresh look at much in this space.
Sure, the government might need to temporally sacrifice some short-term tax revenues to put some of these ideas in place but there’s a cost involved if Ireland wants to be the ‘best small country in the world to do business”. We also need to stop using the fear that ruthless multinationals will exploit any new benefits put in place through clever legal manipulation, let’s face it that’s about forming proper legislation that puts appropriate limits in place so that the policies work for startups and small business but don’t effect larger and more established businesses.

In the end of the day, what’s holding Ireland back from being the best country in the world to start a business? From here it looks like a governmental fear of the unknown, a lack of actual experienced people with ‘in the trenches’ knowledge to help guide them, an obsession with listening to ‘experts’ so detached from the day to day struggles that most entrepreneurs go through, a worry that being seen to be ‘pro-business’ will be seen as being elitist. And there’s no way that creates a culture for startups to grow, develop and go global.

What could be better for Ireland right now than a government that prioritizes helping small business owners and first-time entrepreneurs achieve their dreams of starting and running their own businesses and creating a few jobs in their locality?

It always amuses me when people in the startup space talk about Unicorns as something to aspire to – an imaginary creature thats more fiction than fact.

Let’s face it, the guys and girls you want to meet and hang out with are the Rhinos, hard nosed motherfuckers that everyone respects, they’re basically armoured unicorns.

Joking aside, we need to have a proper conversation about the biggest challenge to startups; the ever insidious industry that’s developing around entrepreneurship and the biggest culprit of all – the overload of  ‘startup events’. It should go without saying, but unfortunately it needs saying –  as a startup founder, every meeting invitation, every event opportunity must be met with a single question – if I accept this invitation is my business better off as a consequence? Not every event is a waste of time but 95% of them are.

Here’s the most honest I can be about this – there is no loyalty card stamps for startup events, attending ten doesn’t get you a free cup of anything, except an eventual industry reputation for being unfocussed, hard truth maybe but hard to disagree with. If you’re spending anything close to a % of your time attending startup events, you are failing (and not in a good, flounders sort of way).

Every single startup business is very different, that’s the unique characteristic that makes it an investable opportunity. It’s also what makes it very hard to learn on the job. One of the worst possible mindsets that a startup founder can get into is thinking that generalised collective learning is a good idea, you have to focus on the problems and challenges facing YOUR business, not some sort of general ‘one size fits all solution’ which is usually the best that most startup events can deliver. The events that are valuable are the ones that before you attend you can clearly see the opportunity to learn or solve some issue you’re having and in these cases the shared experiences of others in the same situation can be very valuable.

Sit back and look seriously at the industry. You can directly correlate the successful businesses that are growing with their lack of attendance at startup events. Sure you’ll see their founders at events every now and again, but I guarantee it’s because that particular event is an opportunity for them, something about it delivers a clear benefit for them. They’re making strategic decisions to devote time to that event instead of the million other things on their plate that day. They arrive on time, leave on time and usually head back to work. And it’ll be one of a dozen events/entries on their calendar that day.

I’ve been lucky enough to see it first hand – the best startup CEO’s (both national and international) that I’ve been fortunate enough to meet are always that way. In the wings or greenroom backstage, getting that last email done before they get on stage, that last line of code, that last investor call. Coming off stage, there’s that urgency to get back to action and avoid hanging around that sometimes (unintentionally) comes across a tad rude, but here’s the simple truth – there just aren’t enough hours in the day to be a successful entrepreneur and you need every minute you have. Urgency and action are brilliant traits for anyone in startups at any level to have.

Sure there are some events out there that are ‘entry level’ events – startup weekends, hackathons, things of that nature but a lot of them are like the X-Factor’s of the industry – entertaining distractions where there’s a one in a million shot of a lucky break. But treat them like that optimistic distractions, social time, time off and away from your business. But don’t think that they count as ‘work’, no investor or customer will, so why should you?

All the things we talk about in terms of networking – sales opportunities, hiring opportunities, investment opportunities DO NOT come about because of event attendance, they come about as a result of having a reputation for action. If the following statement is news to you, then very seriously reconsider the path you’re on, but here goes – during a great recent conversation with Will Prendergast of Frontline VC, he mentioned to me that one of the key characteristics that Frontline look for when they’re investing is a strong bias towards action. That means an attitude of do, not think, actually go and carry out an action that will prove or disprove whatever you’re questioning instead of  just sitting around wondering where you’re going to potentially find the right answer.

It’s really what separates successful entrepreneurs from dreamers, a bias towards action. Most of the time it’s trying and failing, but learning something and then trying again. But it’s all about trying and doing. There is no silver bullet, there is no foolproof scheme that will guarantee your startup success. If you’re hanging around the Startup Industrial Complex hoping that you’ll eventually be indoctrinated into a secret circle who will reveal to you the secret handshake of success it ain’t there.

Think of it this way – if you’re extremely wealthy and go out and buy an extremely expensive McDonalds franchise, guess what you get for the privilege? Six months of working on the front line! Even McDonald’s know that business success depends on its leaders being in the trenches learning absolutely everything about their business – on site, with customers, not in some ivory tower somewhere. Leaders show up, leaders lead, leaders work harder than anyone else in the business and they work on the unpleasant stuff that no-one else wants to touch.

Next time you’re thinking about that startup event, pinch yourself and think – is there really nothing else that needs doing today? Could I schedule research calls with customers? Could I talk to my CTO about the product schedule?  Could I update my Investors and see how they could help me out with this issue I’m having? If all of those are covered, here’s a mad idea – spend time with your family, significant other, or friends, you’ll probably benefit more from that.

Your time is the most precious resource your startup has, use it properly.  

Today, I read something that made me weep. Well, actually, it made me angry, so damn angry.

In a advert for new ‘business mentors’ for a local enterprise board in Cork, it was highlighted as part of the application process that any applicants must have their own professional indemnity insurance, absolutely damning proof that it’s the belief of these boards that professional ‘consulants’ not actual experienced entrepreneurs are the sort of people who should make up these mentor panels.

This is absolutely everything that is wrong about Ireland’s approach to developing entrepreneurism summed up in one.

One of the biggest reputational challenges for Ireland as we seek to promote it as a great place to start a business is to combat the sickening development of an ‘entrepreneurism industry’ – businesses and consultants who, despite having little to no practical experience themselves, believe that they understand the challenges and difficulties of running a business enough to be able to steer a less experienced individual in the right direction.

My own profession, marketing, are the worst offenders of all in this space. Individuals with little practical industry experience, who’ve often never marketed or promoted their own products, and who’ve often just done a college course, or worse still just learned from a book, or online, preaching to others about how to market products without ever having been in the trenches themselves. The dangers that they can do to a fledgling business are astronomical.

Surely the sort of experience that the individuals approaching these boards are looking for is practical, feet on the ground, in the trenches, experience from experienced entrepreneurs, not paid consultants who’ve never had to deal with the pressures of real budgets, real numbers, real problems. Entrepreneurism is gut-wrenchingly hard and to get proper advice you need to get it from someone who’s actually felt it.

This isn’t consultant bashing – there are some individuals out there who are so connected to a wide variety of businesses and entrepreneurs that they genuinely do understand the challenges, but they’re hard to find and frankly they’re pretty busy individuals already.  That a governement body, by default, is looking primarilly for consultants, instead of entrepreneurs willing to share their experience is what makes me sad. Its a easier route for them, a cop out and its what’s keeping these bodies from having true connections and true relationships with their local entrepreneurial ecosystems.

That all being said, if you’re someone who’s been looking for a business mentor, keep a few things in mind.

  1. A mentor who hasn’t been on the actual journey you’re own is little use to you. It’s like learning to drive a formula one car from a cyclist.
  2. Age doesn’t equal experience. Everything is business has changed in the last ten years – how you sell, how you produce, how you make profits. Don’t assume that age equals relevant experience!
  3. Experienced entrepreneurs understand change and how it affects business and make adjustments, look for mentors with a successful track record in several endeavours, not just one.
  4. Mentors are just guidance, the best ones have more questions, than answers. The very best ones will frequently disagree with you, just to see if you can change their minds.
  5. Usually, real entrepreneurial mentors don’t care about the money, for them it’s about helping someone avoid the pitfalls and potholes that they drove into – its therapy and repaying karma as much as anything.

If you’re finding in hard to find someone like this or need a sounding board for ideas, drop me a line at and I’ll do my best to find you a like mind to talk to. If you’re someone willing to help out any entrepreneurs looking for some advice over coffee, drop me a line as well.

Update: A few people pointing out that the insurance issue is just a standard requirement for tendering for government work. My answer to that would be the same – why are enterprise boards taking the easy approach by outsourcing this critical function and one of the most vital parts of what they do. 

48 hours ago,  in one fell swoop, Stripe, a company famed as one of Ireland’s great missed opportunities, changed the game for a whole generation of new Irish technology companies.

Through its new product, Atlas, Stripe, already the payment platform of choice for the majority of new Irish startup companies has now enabled a new Irish company to cut through the red tape and set itself up as a US based, Delaware corporation from day one. No more dealing with the antiquated systems and set-ups here in Ireland. Your Atlas account comes with a fully functioning US bank account from Silicon Valley Bank, thrown in. It’s an incredibly well thought out product offering.

During the growth phase of any Irish startup, at some point, re-registering as a USA based company regularly comes up. Many USA based investors will insist on it as a condition of investment and in general, it’s seen as a commitment to the USA market, often the largest single market for a technology or software startup. Given how much Irish entrepreneurs hate dealing with paperwork and bureaucracy (despite it being in their best interests) this is going to be seen as a massively attractive proposition for many. Through stalling and inaction by government on the actual needs of a modern technology based business when it comes to tax affairs and banking, you’re now going to see a huge number of new Irish startups bypass Ireland entirely and from day one, set themselves up a US-based businesses from a legal and tax perspective.

Some would say that Stripe, built by the Irish uber-geniuses John & Patrick Collison, exists because of their frustration with trying to get an online payment setup in place here in Ireland, during an era where Irish banks were still completely focussed on “real world’ credit card processing. Que the now legendary journey of two young Irish entrepreneurs heading to the USA and now being two of best-known figures in Silicon Valley with a billion dollar company that’s now going to multiply in size.

And the most frustrating thing is the sheer apathy and inaction of the Irish government. We’ve never had an industry more anxious to engage with government, to show them first hand how the UK and other European economies are light years ahead in terms of their approach to technology startups. Whether it’s people like Brian Caulfield and Ian Lucey, talking about how far Ireland’s tax code is falling behind the UK or Dublin Startup Commissioner, Niamh Bushnell showing how far ahead many European cities are in their engagement and approach to startups, it seems like they’re preaching to an empty church. It basically takes entrepreneurs like Pat Phelan, appearing on the Late Late Show to even raise the topic of capital gains tax to any level of discussion.

Satya Nadella, CEO of Microsoft, is famous for a phrase “The technology industry doesn’t respect tradition, it only respects innovation”. An equally famous Cork man is often quoted as saying “Geography is history”. If Liam Casey from PCH can see this; if everyone in the world is accepting it, why do we still have a government in Ireland writing disconnected public policy as if we were all living on the island from LOST.

The last five years of my life have been absolutely incredible, a rush and adventure that I never thought I’d experience once, not to mind twice! And now I have some news but I guess like everything context is important so sorry if this gets lengthy but it needs to be said.

Like every good story there’s three parts.

Chapter One
Meet two incredible guys, Pat Phelan & Chris Kennedy with a crazy dream of transforming how the world tackles a huge, almost invisible problem. We all buy online, but few of us realise how rampant online fraud is and the huge costs that it causes the online businesses that we deal with.

Starting with a conversation at a damp and cold, outdoor smoking shelter at Heathrow Airport where Pat first outlined the idea behind Trustev to me, to moving into the, now infamous, waxing salon first office of Trustev, as we grew slowly, we knew there was something in the idea. At first it was hard to explain, complicated to demo and like every good prototype was ugly as hell, but it solved a big, big problem for an industry that traditionally resisted innovation at every step. Somehow, through sheer force of will and hustle, Pat managed to convince companies to take a chance on the unproven idea and slowly but surely it got easier… actually thats not true, it actually got harder, but the little successes grew into larger successes, the technology that Chris and his awesome team built started to grow legs and slowly and steadily the train started to chug forward. We raised the largest seed round in European history, picked up some nice accolades including the EU Commision’s technology startup of the year and the SXSW Accelerator Prize and started to get traction with customers.

Somewhere around this time, the urge for a change hit me and it coincided nicely with Pat’s plan to move to New York and base the Sales & Marketing functions of the business there, leaving the technical and operations parts in Cork. After chatting with Pat, which to this day is usually the easiest way to solve any problem or doubt in my head, he just encouraged me to go with my gut and that’s where the Trustev adventure came to a sad close.

You see, at that point for a while, I’d been noticing a certain other Cork business… and that’s where the story gets really interesting.

Chapter Two
Meet two incredible guys, Peter Coppinger & Dan Mackey who were already transforming how hundreds of thousands of businesses around the world get work done, all from Cork, all without investment or debt or any kind. is one of those stories that is hard to believe, until you get under the hood and experience the sheer commitment and hard work that goes into keeping each and every customer happy. is a success story like no other, built through sheer hard work and determination by Peter and Dan to build beautiful, intuitive software that really helps businesses get stuff done.

Honestly, I’ve never met a bunch of people like the team at As we grew from 12 people to now nearly 70 in just under two years and no matter how tough it was, we held onto the great culture at Teamwork where everyone worked so hard to ensure that each and every customer got everything they wanted (and then some). Q2 2016 will see the guys and gals at move into to their new, custom designed Teamwork HQ in Cork – I promise that you’ve never seen anything like it – you’ll be finding excuses to visit!

On a timely note, nothing beats the pride of seeing Peter, Dan and the team recognised by the home crowd of the Cork Chamber recently where won Cork Company of the Year at the Cork Chamber Awards, long overdue recognition for what they’ve built. Having regularly walked down the streets of New York, Austin, San Francisco and other cities in a t-shirt and get stopped by customers and fans, it’s about time Cork realised the juggernaut in it’s midst and I thank Cork Chamber for being the guys (and gals) who did so! Next step – getting the boys on the Late Late Show to keep the mammies happy!

Chapter Three
Present day. And here we get to the news. With incredible sadness, I have to tell you all that the part of my life is at an end. To be honest it’s like losing a limb. It’s so incredibly hard leaving a company that was the first and last thing you thought of every single day for so long. I’ll miss seeing each and every one of my teamwork family every day, I don’t think I’ll ever be lucky enough to work again with such a consistently amazing bunch of people who care so much about their customers. It’s like the mother of all breakups and yes, there has been nights of whiskey (and possibly singing)! (Teelings of course! Paul Hayes)

But here’s the thing – there’s this idea that’s been eating away at my brain for a while now; a problem that that I want to solve. I’ve spoken to a few people, infinitely smarter than me, who almost seem to think the same and that there’s something to the idea and so I’m making the leap, putting everything on red (cork bhoy!) and spinning the wheel. This means leaving the safety net of and heading out into the big bad world myself.

Starting today, I’m starting the startup adventure anew, but this time for myself, taking everything that I’ve learned from Pat, Chris, Peter and Dan and building a business that I hope will benefit all kinds of businesses and startups. All I know for sure at this stage is that it will be the hardest thing I’ve ever done.

Cork is forever still my home, if my time at and Trustev thought me anything it’s that all that matters when you’re starting a business is hard work followed by more hard work, with a little hard work at the weekends thrown in. It’s one of the few times where Location, Location, Location doesn’t take precedence. In the words of another Corkman who’s doing ok for himself, Liam Casey, geography is history and while certain things might be easier in certain locations, you can’t use geography as an excuse anymore. Cork, Dublin, London, San Francisco – wherever you go, hard work still awaits.

Huge thanks to everyone who’s supporting this big transition for me. The problem when a lot of your close friends are the hardest working startup people you know is getting the time to talk crazy ideas with them but over the past few months they’ve been incredibly generous with their time and I’ll always be thankful to them. I hate being a tease but for now, but cards will be kept a little close to the chest until we get a little further down the path, but we’re very pleased with progress to date, there’s the start of a business plan, the beginnings of a team and what I think is a great brand, name and identity for the new company.

And, yes, before you ask, it does begin with ’T’ – I’m not taking any changes and who knows? Third time lucky maybe? It’s worked so far!

DC Cahalane
Founder or possibly f.lounder (in training)

So with one week to go until the world’s attention settles on Ireland and the historic decision we have to make as a country, here’s a thought for the employers of Ireland.

You keep saying that you want the brightest, smartest people to work for you. You want people of character, who’ll take responsibility for their actions, who’ll stand up for their opinions. You want thinkers who act, do-ers with ideas. You want people who aren’t afraid to fight their corner. Most of all you want people who engage and are part of the solution, instead of sitting back and being part of the problem. Those are the sort of people you want working for you right?

So next Friday, make a special effort to accommodate your people in their efforts to democratically cast their vote. Don’t rig it so next Friday is the busiest day they’ve had all year, maybe accommodate those who want to vote early, vote at lunchtime, or leave work early to vote, whatever it takes. Don’t force them into the bottleneck of voting after work which is the danger zone. For people who need to travel home to vote consider letting them work from home for just one day (we do all the time here at and its never done anything except improve productivity). Encourage your people to vote, it’s what responsible people do.

It’s just one day but its the most important one in a generation. It’s the tipping point for Ireland, where hopefully we rise to the top of global opinion as a modern, democratic country where despite the hardships of our history, despite the asskicking recession we’ve come though and regardless of the challenges ahead, we recognise one truth over all – you just don’t interfere with love, if two people find happiness then let them be happy, without any terms and conditions applying. For the record that doesn’t make us a ‘forward thinking country’, it just means we finally recognise the oldest truth in the world – all you need is love (sorry Beatles)

Decisions are made by those who show up, make sure your people do.