Business Answers with Tommy Boyle

Building a high-growth startup often forces founders to choose between commercial scale and core social values while pushing themselves to the brink of physical exhaustion. Managing these intense pressures requires a structured approach to business leadership, resilience, and executive health.
Our discussion explores how to navigate extreme operational setbacks, prepare for a successful company acquisition, and maintain personal well-being on the entrepreneurial journey. We dissect the strategic realities of unravelling complex cap tables, negotiating with international buyers, and executing post-merger integrations.
Former co-founder and Chief Executive Officer of Pipit Global Ollie Walsh joins host Tommy Boyle to share first-hand lessons on scaling fintech operations across emerging markets and surviving the intense business exit process.
THINGS WE SPOKE ABOUT
Launching a fintech startup with social impact at its core
Expanding payment platforms to serve unbanked migrant communities abroad
Navigating sudden business crises and managing severe operational risks
Surviving collapsed acquisition deals and building deep personal resilience
Unravelling cap table complications during a major company sale
GUEST DETAILS
Ollie Walsh is the co-founder and former Chief Executive Officer of social impact fintech Pipit Global. Over his twelve-year journey, he successfully scaled the business across fifty countries before its acquisition by United States payments firm Qenta. He currently lectures in marketing at the University of Galway and advises growing businesses.
MORE INFORMATION
Business Answers podcast, hosted by expert broker Tommy Boyle, explores the intersection of strategic growth, finance, and exit planning for SME owners and directors. Each episode features business leaders providing actionable insights to successfully scale, increase valuation, and build a sellable, sustainable, and profitable enterprise.
This podcast is produced by DustPod.io for BusinessAnswers.ie
QUOTES
The fit is the main thing. You're not selling what you have. You need to sell what they want or what they need. - Ollie Walsh
You know, it's a dangerous game leaving a full time job to go into a startup, - Ollie Walsh
You need to stay grounded when there's highs and stay focused when there's lows. - Ollie Walsh
KEYWORDS 
#Exiting #FounderSelfCare  #StartupCapTableManagement #FintechPaymentPlatforms

Building a business with the sole purpose of selling it requires a radical shift in how founders view their daily operations.
Success in this journey demands more than hitting revenue milestones. It requires systematic delegation, strategic advisor alignment, and the courage to step away from delivery. This discussion examines how to build an agency that runs without its founder, handles international expansion, and prepares for a clean acquisition.
Host Tommy Boyle welcomes Kathryn Strachan, former Chief Executive Officer of CopyHouse, to share her journey of scaling to over two million in recurring revenue before executing a clean exit.
THINGS WE SPOKE ABOUT
Transitioning from freelance copywriter to agency Chief Executive Officer.
Hiring permanent staff to remove the founder from delivery.
Overcoming operational bottlenecks by employing senior creative leadership.
Preparing an agency for acquisition from the very beginning.
Managing the severe personal and physical costs of scaling.
GUEST DETAILS

Kathryn Strachan founded CopyHouse, scaling her B2B technology marketing agency from zero to over thirty employees before its 2024 acquisition. She chronicles this experience in her book, Scaling Success: How to Build a Brand that Breaks Barriers. 
Currently a Fractional CMO and GTM leader for UK and US tech firms, Kathryn is a Fractional Chief Marketing Officer for artificial intelligence and technology companies, working as an international speaker and strategist. She also serves as Chair of Mother's Springboard, a charity supporting new mothers re-entering the workforce. 
MORE INFORMATION
Business Answers podcast, hosted by expert broker Tommy Boyle, explores the intersection of strategic growth, finance, and exit planning for SME owners and directors. Each episode features business leaders providing actionable insights to successfully scale, increase valuation, and build a sellable, sustainable, and profitable enterprise.
This podcast is produced by DustPod.io for BusinessAnswers.ie

QUOTES
Agencies can't be sold when the founder is stuck in the middle of it because they're essentially valueless. - Kathryn Strachan
If the goal is to sell an agency, you have to get yourself out of it, which means constantly looking at your workload and what you can move off. - Kathryn Strachan
A smarter play is to have these conversations all along and to be nurturing and building. - Kathryn Strachan
KEYWORDS #HowToSellAnAgency#FoundeIidentityShift#ScalingAnAgency#PostExitGrief

High-stakes business building can cost you everything—your wealth, your health, and your family. The journey of an entrepreneur is rarely simple, often fraught with crises, market volatility, and the devastating personal toll of potential failure.
This episode delves into navigating the pressure of scaling an enterprise and finding the line where persistence becomes self-destructive. You will learn how to create a "secure base," detach your identity from your company, and ensure your business is sellable and valuable, even without you.
Joining host Tommy Boyle is Dr. Pádraig Ó Céidigh, the 2002 EY Irish Entrepreneur of the Year. Pádraig is the visionary who transformed Aer Arann. He is an Adjunct Professor of Entrepreneurship and the author of the best-selling book The Purposeful Decision Maker.
THINGS WE SPOKE ABOUT
Remortgaging home to buy airline
Business success versus business ownership
Perfect storm and need for mentors
Detaching your identity from the company
Selling process: preparation and advice
GUEST DETAILS
Dr. Pádraig Ó Céidigh is a polymath entrepreneur and an Adjunct Professor of Entrepreneurship at the University of Galway. He is renowned for transforming Aer Arann into a regional powerhouse and was named the 2002 EY Irish Entrepreneur of the Year. Pádraig now mentors new leaders, focusing on purposeful decision-making and protecting one's "Safe Harbour" during business scaling.
MORE INFORMATION
Business Answers podcast, hosted by expert broker Tommy Boyle, explores the intersection of strategic growth, finance, and exit planning for SME owners and directors. Each episode features business leaders providing actionable insights to successfully scale, increase valuation, and build a sellable, sustainable, and profitable enterprise.
This podcast is produced by DustPod.io for BusinessAnswers.ie
QUOTES
If the business is less dependent on you, if it's heavily dependent on you, you're going to be locked in for a year, two years, three years into running that business and a handover, - Dr. Pádraig Ó Céidigh
I decided that there's more to me than this business. - Dr. Pádraig Ó Céidigh
I felt that I was in a prison, and I was held in a prison by my attachment to this business, and I needed to get out of that prison. - Dr. Pádraig Ó Céidigh
KEYWORDS #BusinessExit #SellingStrategy #PurposefulDecision #EntrepreneurLife #DetachmentPower

Selling a business for life-changing wealth is a dream, but the personal experience of exiting and then immediately starting over is rarely discussed. Colm Lyon shares his unique journey after selling Realex Payments for €115 million to Global Payments in one of the most admired exits in Irish tech history. 
He details the overwhelming sense of relief that followed the deal and explains why seizing the moment to sell is often a superior strategy to waiting for a higher price.
He also explores the crucial value of attracting strategic buyers and explains the actionable steps founders must take to make their business attractive and easily integratable. Colm reveals why he immediately launched his second venture, Fire, to tackle the coming wave of API-first payments and the unexpected role AI now plays in propelling his new business.
Colm Lyon is the Founder and CEO of Fire. He is a founding figure of Irish fintech and sits on the UK Finance Payments Board in London.
THINGS WE SPOKE ABOUT
Realex sold for strategic buyer value
Relief when your business exit closes
Why selling early is smart strategy
Focus on making business integratable
AI is driving payments innovation
GUEST DETAILS
Colm Lyon is the Founder and CEO of Fire. He is a founding figure of Irish fintech and currently serves as the founding chairman of the Fintech and Payments Association of Ireland. He was given the Outstanding Achievement Award at the National Fintech Awards in 2023 for his contribution to the Irish fintech ecosystem.
MORE INFORMATION
Business Answers podcast, hosted by expert broker Tommy Boyle, explores the intersection of strategic growth, finance, and exit planning for SME owners and directors. Each episode features business leaders providing actionable insights to successfully scale, increase valuation, and build a sellable, sustainable, and profitable enterprise.
This podcast is produced by DustPod.io for BusinessAnswers.ie
QUOTES
A sale is 100% contingent on the buyer wanting it, and you have to have demand for your business. – Colm Lyon
How do we build infrastructure that somebody will be almost jealous of? – Colm Lyon
Try and get your potential buyers to be customers before you enter into any process, so they get to know you. – Colm Lyon
KEYWORDS #BusinessExit #FintechFounder #SellYourBusiness #PaymentInnovation #ScaleUpStrategy

The process of selling a successful business often involves immense financial pressure, emotional turmoil and the risk of deals collapsing at the final hour. Many entrepreneurs struggle to maintain business momentum while discreetly navigating a protracted sale process, often leading to compromise on their ideal valuation and terms.
Our premiere episode details how to overcome these significant hurdles, focusing on maintaining discipline, negotiating firmly on valuation, and managing staff expectations covertly throughout the due diligence phase. You will learn how to insist on 100% upfront payment and why a strong negotiating position is critical to securing your dream exit.
Our guest is Marc O’Dwyer, a seasoned entrepreneur who has bought 14 businesses and sold nine over his 33-year career. Marc recently completed the sale of his cloud accounting platform, Big Red Cloud, for an all-cash deal.
THINGS WE SPOKE ABOUT
 - Tipping point triggers the decision to sell.
 - The importance of getting professional advice.
 - How to handle multiple failed sale attempts.
 - Negotiating for 100% payment with no earn-out.
 - Using Mind Store to visualise a successful exit.
GUEST DETAILS
Marc O’Dwyer is currently focusing on advisory roles for start-ups and private equity firms while preparing to launch a new business venture. Over his 33 years in business, Marc bought 14 companies and sold nine, culminating in the successful all-cash sale of his company, Big Red Cloud. His core strengths include his resilience in negotiation, a disciplined approach to balancing business and family life, and his ability to scale companies, previously making his firm the largest SAP Channel Partner in EMEA.
QUOTES
If you've agreed a price, and it's price you're happy with. If you feel you're right, you need to be resilient. - Marc O'Dwyer
I want the figure I want, I want paid 100% up front, and I don't want to work in the business. And I stuck my heels in the ground until I got that -  - Marc O'Dwyer
Have all your legal, tax and financial information up to date on a regular basis. You never know when somebody might come and knock on your door looking for your business. - Marc O'Dwyer
MORE INFORMATION
Business Answers podcast, hosted by expert broker Tommy Boyle, explores the intersection of strategic growth, finance, and exit planning for SME owners and directors. Each episode features business leaders providing actionable insights to successfully scale, increase valuation, and build a sellable, sustainable, and profitable enterprise.
This podcast is produced by DustPod.io for BusinessAnswers.ie
KEYWORDS 
#BusinessExit #SellBusiness #CloudAccounting #NoEarnout #EntrepreneurResilience