EE: 22 – AskPaul.ie (Part 1) - The Personal Brand that changed the Financial Planning Industry

If you’re trying to buy your first home in Ireland right now, what should you actually do?

He went from selling 100 houses a year to watching the market completely fall off a cliff. Today, Ray Cooke has built one of Ireland’s best-known estate agency businesses with almost 100 employees, 10 offices, approximately €11 million in revenue and more than 1,000 homes expected to be sold in 2026. And it all started with Ray on his own in November 2005, admitting he knew very little about the industry but deciding to give it a go anyway. In Part 1 of our two-part episode with Ray Cooke, founder of Ray Cooke Auctioneers, Lettings, Property Management, Financial Services and Elron, we go right back to the beginning of the journey. Ray takes us through the incredible highs, the difficult years and some of the decisions that completely changed the direction of the business. We discuss: How Ray started the business by himself in 2005 with little experience in the industry. Selling 90 houses in 2006 and 100 in 2007 — before the property market collapsed in 2008. How he survived the financial crisis by pivoting heavily into lettings and positioning the business as a lower-cost letting agent. The meeting with his bank manager during the crash that helped him get everything in order and navigate one of the toughest periods of his career. Opening a new office in Tallaght at the end of 2008 when many others were pulling back. The extraordinary growth from selling just 13 houses in 2011 to more than 1,000 expected in 2026. How important office locations have been to the growth of the business — and what Ray looks for before entering a new area. Why social media has become such a powerful growth engine for the company — despite Ray originally setting up his own social media account simply to prove a point to someone. The conversation with his brother that changed how he ran the company forever — stepping away from personally selling properties and allowing other people to take responsibility. Why moving from working in the business to working on the business became one of the best decisions he ever made — both for the growth of the company and for giving him more time with his children. Growing the company to almost 100 employees and 10 locations. Why Ray is now actively looking to acquire other estate agents, including the recent acquisition of a business in Clonmel. The launch of Elron — helping people who want to invest in property but don’t have the time to find, buy and manage those investments themselves. And Ray’s ambitions for where the business goes from here. This is Part 1 of our conversation with Ray. Part 2 is entirely focused on money and property — including first-time buyer advice, the buying process, Ireland’s housing crisis, adding value through renovations, the rental market and investing in property.We’re delighted to announce that Sons Hair Loss is officially partnering with The Hidden Hustle Podcast! 🤝 This is a partnership we’re particularly excited about because it’s a product we genuinely believe in. Alan has been using Sons products for the past 9 months and has noticed an incredible change in his hair. In the video, he explains why he started using Sons, his experience so far and why we’re delighted to now have them on board as a partner of the podcast. And we’ve got something for our listeners 👇 🏷️ Use code HH40 to get 40% off your first Sons order. Links & Resources: Ray Cooke: https://raycooke.ie/ Follow Ray on LinkedIn: https://www.linkedin.com/in/ray-cooke-1aa7343b/ And all the other social media platforms for some great content!

He went bust, lost everything, and started again from zero. Now he's built a €40 million ARR SaaS company with ambitions to hit €150 million in the next few years — and he's only getting started.

From €60,000 in Revenue to €10 Million: The Incredible Story Behind iCabbi In part 1 of this episode, we sit down with Gavan Walsh to learn about the business he founded iCabbi. In part 2, we discuss life after the iCabbi sale from setting up an investment company and now getting back into the tech start up game. It started in Portugal, with Gavan not being able to find a taxi and wishing something was available on his new iPhone to order one. That was when the idea for iCabbi clicked: what if you could see live taxis on your phone? Gavan tells us how that idea grew into one of the biggest B2B taxi software providers in the world. But it nearly failed before it got started. The original B2C model struggled. The technology was too slow, the market wasn’t ready and the business ran out of money more than once. Something had to change. iCabbi stopped focusing on the consumer app and started building dispatch software for taxi companies instead. One customer became another. Ireland led to the US. And revenue grew from just €60,000 in 2012 to around €10 million by 2018. The journey was anything but straightforward raising money, running out of it, technology failing, family holidays interrupted, expansion into the US and even attempted sales that fell through. Eventually, Gavan sold a majority stake in iCabbi to Renault a life-changing moment that made years of sacrifice feel worthwhile. We discuss: * The holiday in Portugal where the idea for iCabbi was born. * Why iCabbi’s original B2C model failed. * Running out of money and fighting to keep the business alive. * The pivot from a consumer taxi app to dispatch software. * Winning their first customers in Cork and Dublin. * Growing revenue from €60,000 in 2012 to around €10 million in 2018. * The unexpected phone call that brought iCabbi to America. * Why entering the US market was far more complicated than expected. * How Uber changed the taxi industry by challenging its traditional rules. * Building iCabbi into one of the world’s biggest software providers to taxi companies. * Why reliability became one of iCabbi’s biggest competitive advantages. * The reality of being permanently on call while building a technology company. * Raising money, running out of money and dealing with constant setbacks. * Family holidays interrupted by problems back at the business. * The attempted sales that fell through before the eventual deal. * What it felt like when the life-changing sale finally happened. * Why the business you start with is often very different from the business that ultimately succeeds. A brilliant conversation about pivoting, persistence and the reality of building a business when success is far from guaranteed.

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