Be the shark in a small pond

Why leaving NYC fast-tracked my path to CFO

Scott Galloway likes to say that if you want to maximise career-progression, you should move to big talent-dense cities like New York or San Francisco. He’s not wrong; but I think there’s another playbook that could accelerate your career even faster. It’s one I stumbled into half by necessity, half by instinct: go be the shark in a smaller pond.

My path has been all but direct, but today’s reflection is about how making some trade-offs significantly increased the velocity of my career, and my journey towards learning how to lead a company as CFO. In hindsight, the two sacrifices that catapulted my trajectory? (1) Going earlier-stage, and (2) sacrificing location (temporarily).

The cost of an operator’s education

When I left banking back in 2020, I was drawn to the idea of becoming “an operator” in a hyper-growth startup. I wanted to build, not just manage or contribute. Learn first hand how to really scale and create impact. So I started devouring podcasts, books, newsletters and anything I could get my hands on from experienced operators around the world.

But like most pivots, it was a humbling experience. 6 months with applications and interviews taught me some hard truths: everyone wanted “proven talent” for growth stage roles. But it was hard to find someone willing to take the risk unless you had on your CV that you’d done it before.

I realized that I had to go earlier-stage, even if that meant making sacrifices around compensation and risk of failure. And that’s how I ended up with my first role, a fuzzy title (Chief of Staff) with no clear job description at a pre-revenue Berlin-based startup.

It was a true operational crash course, where I built skills with hands-on leadership. But not the growth rocket I had imagined, and while I learned a lot, it was a few years with negative cash flow and a feeling of being “stuck”.

The small pond advantage

My real breakthrough came when I jumped into an even smaller pond. I hadn’t imagined moving back to Denmark - let alone a smaller city (Aarhus) - but it ended up being the accelerator to my career.

Talent density is great - but leverage can be better

The jump proved a good match; I found an ambitious team of founders who had raised a Seed round and found traction in the market already. For them, my background was rare - mix of entrepreneurial and big corporate experience. And for me, it gave a chance to land a role with a scope that would be hard to get in larger cities with more developed startup/scaleup communities.

In the years that followed, I scaled with the company and had more learnings in a short amount of time than any textbook could have taught me. From building and leading multiple operational teams, to raising multiple rounds of financing and growing the company 10x, the journey has brought me so many learnings that have accelerated the speed of my career.

The lessons from the smaller pond

What swimming in a “smaller pond” really meant for me, was that I could accelerate my access to learnings and networks dramatically, getting “years of experience” in a very short timeframe. I got into local CFO and leadership networks, and got access to learn from really smart and experienced people - all while combining it with “hands-on practice” building as fast as I could.

But perhaps the biggest hack was leveraging my experiences, title and responsibilities to then get into more senior and larger networks. It allowed me to build a lot of creditability that would be harder to gain in the larger markets with a narrower role.

Small ponds doesn’t last (if your ambition is larger) - but they can significantly compress your learning, and grant opportunities that are harder to get in bigger places. The catch? Finding the balance between sacrifice, for how long to stay and how to give back. If you get it right, you’ll outgrow the pond quickly and can bring all that experience & knowledge on to the next and bigger pond.

If you feel stuck waiting for someone to “take a chance’ on you; go where they need you more than you need them, and prove your experience there.

What’s your smaller pond?

I’d love to hear stories from others, who have traded in or sacrificed “the big pond” with a smaller one. What was your experiences, and what trade-offs did you make to accelerate your career & learnings?