Jason Ekaireb
I have always embraced my entrepreneurial spirit, even while working within big organisations. My career began with a three-year training contract at PwC, after which I had the opportunity to work on the trading floor at Salomon Brothers. Within a year, I was entrusted with launching a brand-new trading desk — a joint venture between the interest rate and credit businesses.
Building on this entrepreneurial mindset, I developed new products, including the first cross currency credit card securitisation, and established new business areas within the organisation. From Salomon Brothers, I joined Goldman Sachs and spearheaded several ventures, including a joint initiative between asset management and trading.
I was promoted to Partner and continued to innovate in new product areas. Towards the end of my time at the firm I was asked to turn around an existing business, a challenge I successfully navigated. During this period, I started to connect with technology-focused private equity funds and discovered several unlisted companies, including Facebook and Airbnb—now household names. This experience broadened my understanding and enthusiasm for the evolving technology landscape.
Driven by a desire to innovate, I sought to create a new technology incubator at Goldman Sachs. Despite enthusiasm from senior leadership, the initiative did not ultimately proceed, and so in 2015, I made the pivotal decision to leave. Unlike many of my peers who continued excelling in their respective fields, I found myself questioning the relentless pursuit of financial success. I reflected deeply on what truly gave my life meaning. I still had so much life left to live and wanted to do so with greater freedom—free from the singular focus on accumulating wealth. Additionally, I aspired to create a lasting legacy for my two daughters. I didn’t want to hand down wealth but instead establish a family business they could work in, where they would learn and in turn, add value.
Naturally curious and drawn to innovation, I started to explore new areas that intrigued me. At the same time, I recognised that as an older entrepreneur, I needed to use my financial expertise to my advantage. Through extensive research and conversations, I identified a gap in the market for a more effective way to invest in property bridge lending. I saw an opportunity to revolutionise the space by crafting my own technology platform from scratch. In the summer of 2017, I launched LendDirect, offering investors a unique investment proposition in short-term property lending, through a structure that provides instant diversification and segregated liquidity. Interest grew organically, with friends investing in the platform. Since then, our growth has been entirely driven by word of mouth.
We have delivered strong returns to investors and prioritised exceptional customer service. Our technology provides investors with a transparent, real-time view of their portfolios. The best external validation has been that more than half of our investors have increased their investment with us, and every single investor has come through a personal recommendation. Of course, risk is inherent in any investment, and we ensure that potential investors fully understand these risks before committing.
Transitioning from the corporate world to launching a startup later in life has been incredibly rewarding. It has given me freedom, a renewed sense of purpose, and a legacy for my daughters — both of whom have worked in the business, with one still actively involved. However, this journey has not been without its challenges. Building a tech-driven business without a technical background was a steep learning curve. I engaged an external agency to develop the platform but had to master an entirely new lexicon of terms. Additionally, I no longer had the support network I once took for granted — lawyers, accountants, HR specialists. In the early stages, I had to take on all these roles myself. I then needed to find the right people independently, which required a significant amount of time and effort. Fortunately, I now have a great support network in place.
For those navigating midlife transitions, my advice is: find something that keeps you engaged and aligns with your aspirations. Approach it with the same passion and diligence that fuelled your success in the first half of your career. Importantly, don’t be afraid to forge your own path and be willing to deal with failure. Embracing challenges can be far more rewarding than simply sticking to what feels comfortable.
Circle Square Q&A
What 3 words best describe you? Visionary, creative, contrarian.
If you could offer your younger self one piece of advice, what would that be? Giving is infinitely better than receiving.
What do you consider to be your greatest achievement? My children.
Which person (dead or alive) would you most like to invite to dinner? Moses.
How has age strengthened your advantage? There is no substitute for cumulative experience.
What inspired you to join Circle Square? The opportunity to connect with people with similar opportunities and challenges.