When Andrew O’Shaughnessy first walked into the Entrepreneur Experience in 2011, he did not arrive as a seasoned executive dispensing advice. Instead, he arrived at Garryvoe Hotel in east Cork looking for it.

Back then, his Cork-based start-up was called Newsweaver and it specialised in email marketing.

His company was successful, but growth had started to flatline. O’Shaughnessy came seeking a way to boost growth and, if necessary, reimagine his business. 

He had been invited to the event by Michael O’Connor, the then chief executive of the innovation body CorkBIC. O’Connor had explained that he was organising a new event where 24 emerging entrepreneurs would be holed up with 24 seasoned entrepreneurs for 24 hours for intensive mentoring and group sessions.

O’Shaughnessy immediately said yes. “None of us knew what we were getting into or what it was about. But I just remember the seasoned entrepreneurs, as they call them, they were so into it. They were so giving, they put so much into it. It was just infectious,” he recalls.

A lot has changed since that inaugural edition of the Entrepreneur Experience. 

CorkBIC has been rebranded as AxisBIC. The event has found a new home at Ballymaloe. And O’Shaughnessy pivoted, rebranded his business as Poppulo, scaled it significantly after raising €30 million, and subsequently sold it.

Yet, the way he sees it, the ethos of the event remains the same – entrepreneurs helping entrepreneurs. 

It is why, seven years after turning up looking for help, he now arrives in Ballymaole each year to help the next crop of founders. 

“I was delighted to do it because it meant so much to me when I did it,” he recalls. “The other thing is that you are getting together with a group of people where there’s empathy and understanding, where you’ll get encouragement, inspiration, and just great advice.”

Hard truths and big decisions

I am meeting O’Shaughnessy as AxisBIC launches the applications for emerging entrepreneurs to attend this year’s event in October. Once again, the Cork entrepreneur will be in attendance. 

But as he reflects upon the event and the issues facing founders, it is impossible not to dwell upon his own journey because it highlights the importance of perseverance, values, and facing what O’Shaughnessy describes as “hard truths”. 

In 2013, two years after attending the event, he decided on the Poppulo rebrand and transformed it into a cutting-edge, internal communications company. 

The decision to pivot came after a hard look at the business and two years of hard work. 

“People will talk a lot about vision and achieving something, and doing something for the planet, and all sorts of stuff. And all that is true,” he says. 

“In the end, you also want to make it a financial success as well, and that was hugely important to me. And so after years and years, when we had a great company, great culture, running really well, but it was just sort of flatlining, and it wasn’t going anywhere.”

O’Shaughnessy says he “faced reality” and accepted this was not what he was in business for. He wanted to build a company that could be the best in the world and he knew this version of the business could not do that.

“It took about two years of searching and trying different things and different products that failed,” he says. 

“I didn’t just happen on to it, and when it did happen, it was only because I was looking, and only because we were trying different things.” 

With internal communications, he felt it could be the best in the world. “It was a huge risk. That was the pivotal moment when we decided, look, we’re not going to go half hard at it. We’re not going to do a pilot project or something. We know enough, this is an opportunity, and we put everything behind it,” he says.

The results spoke for themselves. Poppulo transformed into a rapid-growth business with blue-chip clients such as Rolls Royce, Bank of New York, HSBC and LinkedIn.

By 2019, it raised €30 million in funding from US private equity firm Susquehanna Growth Equity (SGE). After the deal, O’Shaughnessy and other shareholders still retained majority ownership.

Further growth followed. However, by  2021, O’Shaughnessy had started to think about selling. 

“I decided we were going to sell because a lot of things had aligned. It was the right time, valuations were really high,” he says.

“The second thing was that the industry that we were in was ready for consolidation, and we could be a kingmaker. Anyone who came together with us was going to be the leader. And so I went to the market with that.” That year, it merged with US-based Four Winds Interactive in a deal that created a business with combined annual sales of $100 million, and, according to Bloomberg at the time, a combined value of $1 billion. After the deal, private equity controlled the bulk of the company.

The combined entity retained the Poppulo name but, after bedding in the merger, O’Shaughnessy stepped down as CEO while maintaining a board seat.

“Personally, I felt I’d achieved everything that I wanted to achieve from us. I’d done everything. You grow again, you grow again. You pivot again. I’d done that, I was done, but done in a positive way,” he says.

Andrew O’Shaughnessy on investing in companies and founders

Since stepping back from running Poppulo, O’Shaughnessy has invested in a number of businesses, including Squid Loyalty, a fintech that specialises in managing loyalty cards. He has also backed CergenX, a Cork medtech firm that aims to revolutionise the assessment of newborn babies’ brain function.

“I look to see how passionate they are about what they do. Two, do they listen? Are they telling me or are they asking me? Now, they know an awful lot more about their business than I do, but there’s things you can help with. Are they listening? And do they take what you’ve said and actually apply it? That’s really important to me, and the business has to have the potential to really grow,” he says. 

“If it’s growing, you’re into something new all the time. So you’re having to learn all the time. Things that used to work when you were this size don’t work when you get bigger. So things are breaking all the time on the way up. Unless you’re watching, listening, and learning all the time, you’re going to flatline. So if they’ve got that kind of an approach and they’re passionate, and there’s the room to grow, then I’m really excited about business.”

Lessons from the journey

Within minutes of meeting O’Shaughnessy, his passion for business comes through. Before I get a chance to ask him a question, he rolls out a host of questions about the performance of The Currency. 

And, as he talks about the lessons he learned through his own business career, he also gives insight into what companies can expect at this year’s Entrepreneur Experience

“Starting a business is really tough. It’s hard. It’s because there are so many aspects to the business that you have to be on top of. There’s the product itself, whether that’s a service or a technology or a process, or whatever it is. And then getting that product-market fit with that. And then, of course, there’s the money aspect of it, all the stress that that brings,” he says. 

“You may be great on your product, but you have to go out and sell the thing then, and you might not be a salesperson. Hiring, managing people. There are just so many aspects of this that are hard,” he says.  

He also says it is hard to fit in starting and running a business with the rest of your life: family, relationships, children. 

However, a key learning from his own career was not avoiding the things in business he was poor at, or less interested in, and focusing instead on the things he enjoyed. It is a pitfall he believes many entrepreneurs fall into, himself included.

“What happens in the Entrepreneur Experience is, the seasoned guys in the room if you’re in a group session – and there are six or seven people there – they’ve been through it, they sniff that out. They’ll throw it at you straight. Not to show you up. It’s not like Dragons’ Den or Shark Tank. It’s just facing reality. They’ll pick the bit, and they’ve just put it to you straight,” he says.

The way O’Shaughnessy sees it, many entrepreneurs know the mistakes they are making, but are often afraid or unwilling to do something about it. This is where good advice and mentoring can help, he says.

“You know it anyway, but they make you face it. In my own career, learning to do that, to face the hard bits was probably one of the biggest learnings that I had. And once I did that, I used to go after it. We seek them out.

“In Poppulo, we had a culture of doing that, just going at them. I think the Entrepreneur Experience is great for that, because you can’t go through those sessions and not get found out. And that’s what you want. These people are on your side, they want to help you. There’s a wealth of experience in the room to be had there, and that’s priceless.

“It comes not just from the seasoned entrepreneurs. I think even if they weren’t there at all, and you just had 24 people at the same stage early in their business get together, just the cross-helping of each other would be great. It is just an inclusive, really helpful environment to be in.”

Another key learning from his career is the importance of mission and being true to yourself.

He admits he was “gung-ho when he launched the business”. He wanted to do something, anything. His view has long since changed. 

“I think it’s really important that you are in some way passionate about the thing that you’re doing. Let’s say you are successful, it’s a long road to build a business and to make it something big. You’re going to be doing it, you know, week in, week out, for years. So it’s so important that it’s something that you’re actually excited about. And for me, I wasn’t particularly excited about what I started out with, and I felt really stuck because I had years behind me. It was nearly successful, but not quite. You couldn’t walk away from it. You couldn’t leave it. I wasn’t enjoying doing it, and I was stuck. And that’s not a nice place to be,” he says.

“And in the end, how I got out of that was I started running the business the way I wanted to run the business. So it didn’t matter what I was doing; it was how I was doing it. It was how I was treating employees, and how we work together and the culture we created became the goal for me, or the thing that I got that satisfaction about. But there has to be something, because it’s so goddamn hard that there has to be something really at the core of it to carry you through.”

The 2025 Entrepreneur Experience™ will take place on Friday, 17 and Saturday, 18 October 2025 in Ballymaloe, Co Cork. The Entrepreneur Experience™ is a unique event for 24 emerging entrepreneurs to gain unparalleled access, advice and mentoring from 24 of Ireland’s most successful business leaders over 24 hours. The Entrepreneur Experience is organised and managed by AxisBIC in partnership with Cork City Council, Cork County Council, Grant Thornton, Broadlake, Quintas and The Currency.

For details on how to apply, click here.