Digital Irish Podcast

Digital Irish podcast celebrates Irish innovation and the Irish startup ecosystem: connecting founders, investors, and innovators across Ireland, the diaspora, and beyond. Each episode features candid conversations with VCs, entrepreneurs, and business leaders sharing the real story behind building companies: the setbacks, the playbooks, and the lessons you don't find in press releases. Whether you're plugged into the Irish startup scene or part of the Irish community abroad, Digital Irish is your window into one of the world's most connected startup communities.

In this episode, we sit down with Stephen Tallon, a Partner at McCann FitzGerald, one of Ireland's leading law firms, where his practice focuses on emerging companies, venture capital, and M&A. Stephen trained in Ireland before spending almost a decade in London at Orrick, a global firm with deep roots in Silicon Valley, where he worked on some of the biggest deals across Europe and the US — including transactions involving Stripe, Revolut, and Salesforce Ventures. He's since returned home to Ireland with his family and joined McCann FitzGerald, which has one of the largest and most experienced emerging company and VC teams in the country, advising founders from pre-seed all the way to exit.
In this conversation, we get into the legal side of fundraising that most founders overlook until it's too late. We cover:
What investment readiness actually means from a legal standpoint, and what VCs are really evaluating in those first conversations

Why your cap table could make or break a deal before it even gets started

What founders consistently get wrong before and after signing a term sheet

The key terms founders should push back on and which ones are genuinely non-negotiable

What a Delaware flip actually involves for Irish companies pursuing US investment, and when to do it

If you're an Irish founder thinking about raising investment, this episode is packed with practical, honest advice on how to protect yourself and set your company up for the long run.

About Stephen Tallon
Stephen Tallon is a Partner at McCann FitzGerald LLP, where he focuses on emerging companies, venture capital, and M&A. He trained in Ireland before moving to London in 2017 to join Orrick, a global law firm headquartered in San Francisco, where he spent almost a decade advising on landmark transactions across Europe and the US with companies including Stripe, Revolut, Butternut Box, Graphcore, Salesforce Ventures, and Macquarie. Now back in Ireland, Stephen works with founders and investors at every stage, from pre-seed through to exit.
About McCann FitzGerald
With over 640 people across four countries and more than 480 lawyers and legal professionals, McCann FitzGerald LLP is one of Ireland's premier law firms. Operating from offices in Dublin, London, New York, and Brussels, the firm provides expert legal counsel to clients in Ireland and around the world across corporate, banking and financial services, disputes, and real estate. McCann FitzGerald has a long-standing reputation for innovation and excellence, and its emerging company and VC team is one of the largest and most experienced in Ireland.
Want to get in contact with the Digital Irish team? Email us at podcast@digitalirish.com

Marty Loughlin is back for round two. Where the first conversation was about why Irish founders think globally, this one's about what actually happens inside the room. Dave and Marty get into how DIVF makes decisions, what they do after the cheque is written, and some pretty blunt advice for any founder preparing to raise.
Marty Loughlin is a partner at the Digital Irish Venture Fund (DIVF), the fund built on the back of the Digital Irish Angels investment group, founded in 2016. DIVF backs Irish founders scaling globally with a particular focus on those entering the US market, drawing on a network of Irish-American business leaders across the diaspora.
What we cover
What Marty looks for in a first founder meeting
DIVF's playbook after the cheque is written
How to know if you're actually ready to raise
The pitch deck advice every founder needs to hear
Get in touch
Marty Loughlin: marty.loughlin@digitalirish.com
Learn more about DIVF: digitalirishfund.com
podcast@digitalirish.com

In this episode, we sit down with Marius Smyth of the Digital Irish Venture Fund (DIVF) for a follow-up to our earlier conversations with Marty Loughlin. Where Marty walked us through how DIVF picks founders and the realities of pitching the fund, Marius zooms out to the layer underneath: how DIVF is building the Irish diaspora into a working venture ecosystem rather than relying on it as a goodwill network. He is leading the build-out of a physical “Green Room” for Irish founders in New York, architecting the fund’s co-investment strategy, and thinking hard about where a fund of DIVF’s size best fits in an industry increasingly polarised between mega-funds and solo angels.
In this conversation, we get into:
Why the Irish network is a sourcing engine, not just a hospitality network — and what DIVF is building to keep it commercial rather than a mutual appreciation society.

How DIVF co-invests alongside other funds without becoming dependent on whoever is leading the round.

Why the right place for an Irish venture fund right now is not at either end of the cheque-size spectrum, and where DIVF deliberately sits.

The most practical first step for a founder coming out of Ireland with no US network, plus where the gaps still are in the Irish ecosystem itself.

If you’re an Irish founder building for the US market — or thinking about the next layer of infrastructure the diaspora needs — this episode is the strategic counterpart to Marty’s tactical advice from the earlier episodes.
About the Digital Irish Venture Fund (DIVF)
DIVF is an early-stage venture firm focused on Irish and Irish diaspora founders building for global markets. The fund operates as “friendly operators” rather than traditional shark VCs — providing hands-on operating help, warm introductions, and access to a diaspora network across New York, London and Dublin after the cheque is written. DIVF co-invests alongside other funds and works alongside the broader Irish ecosystem — Enterprise Ireland, universities, accelerators, and angels — to bring strong Irish companies into the US market.
Want to get in contact with the Digital Irish team? Email us at podcast@digitalirish.com

In this episode, we sit down with Michael O'Loughlin, Managing Partner at Argonautic Global, to get into the practical realities of Irish companies entering the US market. Michael has spent two decades working across banking, payments, regulation, central banking and venture capital — with experience spanning Ireland, Europe, the Middle East and the United States. Before his current role, he served as Chief Advisor to the Deputy Governor at the Saudi Central Bank and Strategic Advisor to Fintech Saudi, helping build one of the region's fastest growing fintech ecosystems from the ground up.
This episode is about what actually works when Irish companies come to the US — and what doesn't. We cover:
Michael's journey from Ireland to Rochester and the investing lens it shaped

The different types of investing he's involved in, from angel to growth equity, and why that full picture matters

The readiness threshold — revenue, product maturity, team size — before a US move makes sense

The mindset shift required when moving from raising in Ireland to raising in the US

Where Enterprise Ireland's support ends and where the founder has to take over

How much warm introductions actually matter versus cold outreach, and how to get in the room

What investors want to understand first when looking at an early-stage company

What a well-prepared founder looks like walking into a meeting

Red flags that signal a company isn't ready, even when the product is interesting

What Irish companies that land well in the US do differently

If you're an Irish founder thinking about the US, or anyone working in the Irish startup ecosystem on either side of the Atlantic, this one is worth your time.

About Michael O'Loughlin
Michael O'Loughlin is Managing Partner at Argonautic Global, focused on AI, fintech and emerging technology infrastructure across global markets. Over the past two decades he has worked across banking, payments, regulation, central banking, venture capital and international ecosystem development, with experience spanning Ireland, Europe, the Middle East and the United States. Previously, Michael served as Chief Advisor to the Deputy Governor at the Saudi Central Bank and Strategic Advisor to Fintech Saudi. He remains actively involved in the Irish technology and investment ecosystem through initiatives including Blockchain Ireland.

About Argonautic Global
Argonautic Global invests in AI, fintech and emerging technology infrastructure across global markets, with a focus on identifying and backing companies with the potential to scale internationally.

Connect with Michael
LinkedIn: https://www.linkedin.com/in/oloughlinio/

Argonautic Global: https://argonauticventures.com/
Blockchain Ireland: https://www.blockchainireland.ie/