“I don't know where I am going, but I know exactly how I am going to get there”
The Lion Trackers Guide to Life - Boyd Varty
It was 5:20 am on a clear May morning. The water on the bay was glassy-calm, a heron stood sentinel, waiting for its next catch. The world was in lockdown, and the company I had led had filed for bankruptcy weeks earlier. I had invested in this venture, brought our network into it, and every failure felt like my own. My strongest attributes—my energy, my ability to connect, my passion for coaching entrepreneurs—all seemed mute in a global pandemic. With my graying hair and ex-finance resume, I felt indistinguishable from countless others adrift in uncertain times. I had no roadmap to turn my life around, no strategy to lift the weight of culpability and shame from my shoulders.
As I watched the heron, its patience struck me. It stood unwavering, focused on its goal despite the stillness of the water. In that moment, a tiny spark of resilience flickered within me. Little did I know that this moment of despair, punctuated by a glimmer of hope, would become the catalyst for a profound personal and professional transformation.
So often I have been worried by what people will think of me, of my decisions. I have fretted over how my outcomes are perceived, If people think I am successful, smart, or that I do enough. I worry about what my mum and dad will say about my choices, whether my wife will think I am a good partner and more recently whether my kids will think I am a good father, a good role model.
I worry about being judged for earning less than my wife. I have felt uncertain being the only dad at drop-off, or flying solo with my 3 kids. It took me a decade to shake off my decision to leave finance and the judgement I perceived in others, through my own judgement of myself.
I knew that when I left finance, being out in the “real world” was not going to be easy, that earning a dollar would be much harder, but with all the cockiness and arrogance of a 31 year old “hedge fund guy” I figured I would be fine. I knew so many people, networking was “my thing” and I had so many ideas and avenues I wanted to explore, success would be sure to follow.
At the time, I thought I had a plan, but I know now I was so far from what I needed. It turned out, in retrospect and many years later that my plan was “I knew a lot of people and I had a lot of ideas”....!
In my first 2.5 years after leaving the City, I started a fine wine investment fund, joined a wine technology platform as the commercial director, took on numerous consulting gigs in finance and further afield as well as trying to learn and develop my knowledge and network in angel investing.
Amidst this exploration, my wife and I moved to New York with a 6-month old first child, fulfilling a lifelong ambition of mine to live in the big apple and driven by a big new role for her in her career.
Admittedly, being in New York in 2013, as the tech-scene was really taking shape, made adopting the role of angel investor a lot easier, especially with community builders like Charlie O’Donnell, who is now a good friend, being so open to collaboration and support. But I could never shake off the rampant feeling of impostor syndrome. Of not quite feeling like I really knew what I was doing. Of not knowing what the terminology meant, of feeling like everyone in the room already knew each other.
This feeling ebbed and flowed, particularly in the summer of 2014 when the first angel investment I had made was acquired by Pinterest after a serendipitous introduction I made for the company, briefly making me think I was “The Greatest Venture Capitalist of All Time” but that's a story for another post!
My angel investing was happening alongside 2 of my best friends, under the umbrella of our Nucleus Adventure Capital vehicle, which allowed us to project a larger halo than reality represented. However I was the front man for our activities as both my partners had day jobs.
I spent my days networking to source investment opportunities and grow our network with the aim of bringing friends, colleagues, high net worth individuals and ultimately family offices, into our investment orbit, as partners.
After our initial success in 2014, the following few years saw our investments follow a more traditional early stage path - a handful of failures, a number of stalling or stodgy companies and one or two maybe showing signs of promise.
Amidst this, one of my partners quit his job, but very shortly after, moved with his family to Atlanta, catalysed by his wife’s career. Despite efforts to integrate the Atlanta tech scene into our strategy, it became clear that we needed to refocus. My partner’s second move, this time to California brought new challenges, and ultimately, we had to reassess our future.
Around the same time, my self doubt about direction and destination peaked again and I decided to apply to do an Executive MBA @ NYU Stern. I made this decision while my wife was pregnant with our 2nd child. I was fearful of what my career might look like if the investing didn't work out - I was afraid of the question - what have you been doing?
While the worth of the Executive MBA is debatable, it gave me some invaluable experiences, some great connections and included an eye-popping week in Beijing.
Me on the Great Wall of China
As my MBA was concluding, I was offered the role of COO at one of the companies - an ice cream brand - we had invested in. The decision to take this job was rolled up into a whole bunch of feelings and fears, with ego and purpose very much at the centre. In the context of Nucleus, it seemed to fit with a narrative of investors, turned operators ultimately having a stronger pathway to realising the dream of raising our own VC fund.
The two years at the ice cream company was a rollercoaster and I feel like I could write a book on that experience alone - but needless to say, I learned more in that time than perhaps any other time in my career. In the immediate aftermath of my leaving, weeks ahead of the company filing for bankruptcy and a global pandemic, my feelings of fear and failure had never been higher.
I was terrified to talk to anyone I had invested alongside, had worked or partnered with - all because I thought that they would blame me for what happened.
During the lockdowns, in between homeschooling, zoom calls and visits to the grocery store with gloves on, to fight over eggs and bread, I did some deep soul searching as I stared into my apparent abyss.
Ryan Holiday’s “The Obstacle Is The Way” helped me move past self-loathing and blame. Like the heron waiting patiently, I had to learn to stand still, reflecting on the lessons of failure and the stillness imposed by lockdown. Slowly but surely I re-engaged in the investing world, through a mixture of advisory, consulting and mentoring.
As the world began to normalise and our investing activities expanded, including some liquidity events from early investments, the idea of starting our own fund began to surface and I was continually told that if my partners didn't want to do it, I should do it alone.
At the same time, I was introduced to the CEO of a nutrition company, initially because of our common passion for health and wellness, but which ultimately resulted in my becoming his executive coach, despite my protestations I wasn't qualified. He insisted “You have been coaching entrepreneurs and leaders for 10 years - I want you to coach me.”
For a time, I juggled both coaching and raising the investment fund. But when my partners’ interests waned, I realized I was clinging to an old dream. A conversation with a family office head brought clarity—was this really what I wanted?
With my wife having taken another big job 18 months previously - I had continually been dogged by the need to be more in my wife's eyes, in my family's eyes, in my friends eyes. I felt I needed to do more for my family, to do more for my wife such that she had an off ramp.
Sharing this with her lifted a weight off my shoulders. Together, we considered what each path meant for both me and our family. Her words stayed with me: I was enough, no matter what I chose.
Ultimately, I chose to pause my pursuit of a fund, realizing that true success lies not in what others expect. I now embrace the freedom to invest in what aligns with my values and the flexibility to focus on what matters most—being present for my family and supporting others in their own journeys.
I realised that I was chasing a goal I had set for myself almost 10 years previously, but had never really stopped to consider, if it was still something I truly wanted. I was going with the flow of what I thought I should do, what other people thought I should do and would approve of.
The main thing I love about angel investing is supporting incredible entrepreneurs to solve problems - being a sounding board and a resource in whatever way I can. It’s this aspect, above all others, that has always excited me about investing at such an early stage of a company's life - being a mentor, a guide, a coach.
In the aftermath of curtailing my pursuit of my own fund I leant into my coaching research, education and client development. I was helped immensely by Sunil Arora and Megan Dolce - both amazing humans and incredible coaches - and latterly by Steve Schlafman, whose writing and willingness to share are second to none.
My experiences—from finance to entrepreneurship—helped me realize the importance of perspective. This is the core of my coaching practice: helping others navigate pivotal decisions with clarity, confidence, and a grounded sense of self, free from external validation.
Even now, I wrestle with imposter syndrome, a feeling of being an outsider despite my successes. As a coach, I see this in many high achievers: the sense that they must constantly prove themselves. Overcoming this begins with recognizing that worth isn’t defined by external validation, but by cultivating a sense of fulfillment and purpose from within—by measuring success on your own terms, rather than through the expectations of others.
A few weeks ago, I found myself once again watching the sunrise over that same bay. The scene was eerily similar—the glassy water, the patient heron—but everything else had changed. As I sat there, no longer weighed down by shame but buoyed by purpose, I reflected on the journey that had brought me here.
The bankruptcy that once seemed like an endpoint had become a turning point. My perceived failures had transformed into the very experiences that now allowed me to guide others through their own professional labyrinths. The gray hair that I once saw as a liability was now a badge of hard-won wisdom.
As I watched the heron finally make its catch, I smiled, recognising the lesson it had taught me years ago. Success, like fishing, isn't about immediate results—it's about patience, persistence, and the willingness to stand steady even when the waters seem still. In embracing this truth, I had not only found my path but had become a guide for others navigating their own uncertain waters.