Name: Ciaran Hynes

Title: Managing Partner

Organisation: COSIMO digital

Ciarán Hynes is co-founder and Managing Partner at COSIMO Digital, where he also serves as COO/CFO. Decades of entrepreneurial and investment experience allowed Ciarán to realize the transformative possibilities of blockchain technology from the outset. Since then, he has been helping COSIMO Digital’s expansive network of startups, partners, and investors navigate the complexities of the digital economy to achieve success.

A serial entrepreneur, Ciarán has founded seven companies, led five as CEO, and successfully completed multiple buy-side and sell-side transactions. Throughout his career, he has raised over $100 million in capital, brought more than 25 products and services to market, and served as a board director for over 20 companies.

Additionally, he is an ICCA International Marketing Award winner and was honored as one of the Irish America Wall St. Top 50 in 2019 and again in 2023. He has spoken at many prestigious international conferences and events. Beyond his professional achievements, he completed the Dublin City Marathon in 2008 and played Minor and Senior Hurling for Dublin.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Ciaran's answers will encourage you in your leadership journey. Enjoy!

Cheers,

Jonno White

1. What have you found most challenging as a leader?

Hiring the right people, making hard decisions about letting people go, and doing it early enough.

Obviously, hiring the right people reduces the likelihood of facing the difficult decision to let someone go. When leaders focus on bringing in talent aligned with the organization’s goals and culture, the chances of underperformance or misfit diminish. However, even with the best hiring processes, circumstances change—business priorities shift, and tough decisions still need to be made.

Leadership is not about avoiding tough decisions but about handling them with integrity, empathy, and a focus on the greater good. Making hard decisions, like letting people go and hiring the right people, are two sides of the same coin—they shape the organization’s future and its ability to succeed. Leaders who excel in these areas set the foundation for a resilient and thriving team, but it always presents a challenge.

2. How did you become a leader? Can you please briefly tell the story?

I think it evolved and was largely driven by my involvement in sports as both a player and a coach. Those skills were highly transferable and quickly became apparent in the business side of my life.

Growing up in Ireland, Hurling was my chosen sport, and my school was fortunate enough to play in a Dublin Colleges Final in Croke Park, our national stadium, in 1984. We were ranked underdogs taking on one of the giants of Dublin, ironically St. Davids. We won the game by a single point, but not without several of us standing up that day to lead the team to victory against all the odds.

A few years later, I had the honour to captain my club, Kilmacud Crokes, to a U-21 championship victory, and in 2006, I was the head coach when the club won the U-14 championship title, once again against all the odds!

I think you must be a leader to be an entrepreneur. I started my first company at the age of twenty-five and have been an entrepreneur since.

3. How do you structure your work days from waking up to going to sleep?

I wake at 6.30 am and check/answer emails from Europe if urgent and file the rest for later. For breakfast, I make a protein and fruit shake and drink half, work out at the local Y, which I do six days a week, and when finished, drink the other half.

Most of my day is spent on Zoom calls with my team, our portfolio companies, or companies we can partner with. I always leave time for action items on fundraising, operations, and finance.

Evenings and weekends are spent generally with my kid's sports or practice, which I thoroughly enjoy. I also watch Jeopardy and the occasional TV series. As a huge sports fan, I will also watch the Red Sox or Celtics if they are playing.

I am a huge believer in proper sleep and the importance of sleep. Having read Outlive by Peter Attia, I won’t allow myself to have less than eight hours of sleep a night and take his suggested sleep-aiding capsules prior to bed, which is 9.30 pm or 10 pm at the latest.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

Hire for talent, not for role.

Not a new principle or lesson, but one I was reminded of recently. It is so important to seek out individuals with high potential, adaptability, and core skills rather than focusing solely on their immediate fit for a specific position. This forward-thinking strategy aligns hiring decisions with the organization’s long-term needs and its ability to thrive in an ever-changing environment.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

“Good to Great” by Jim Collins.

It speaks about getting the right people on the bus before you decide where to drive it! It emphasizes the importance of building a team of the right individuals before determining the organization’s direction. This approach prioritizes talent, values, and cultural alignment over a rigid focus on roles or immediate tasks.

When Steve Jobs returned to Apple, he focused on assembling a team of innovators and visionaries who could bring his vision to life. His team, including Jony Ive and Tim Cook, was instrumental in transforming Apple from near bankruptcy to one of the most successful companies in history.

6. If you could only give one piece of advice to a young leader, what would you say to them?

You have two ears and one mouth…..and for very good reason.

The phrase “two ears, one mouth” was one my mother reminded me of often. It serves as a simple yet profound reminder of the importance of listening over talking. It highlights the need for leaders, team members, and individuals to prioritize understanding and connection through active listening. I really believe you learn more by listening more and not loving the sound of your own voice.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

My business partner, Rob, told me the story of the OODA loop that he learned as a Navy Pilot. The OODA loop, developed by U.S. Air Force Colonel John Boyd, is a decision-making framework that stands for Observe, Orient, Decide, and Act. Originally designed for military strategy, it has profound applications in entrepreneurship, where agility and strategic decision-making are critical for success.

The OODA loop is a powerful framework for leaders and entrepreneurs, enabling them to act decisively and adapt swiftly in dynamic environments. By embedding the principles of Observe, Orient, Decide, and Act into their processes, entrepreneurs and leaders can foster innovation, outmaneuver competition, and build resilient businesses capable of thriving in uncertainty.