How an ex Goldman banker and PE associate broke into startup ops

What it actually takes to switch from finance to startups

Feb 08, 2026

Hi, I’m Hannah! Welcome to Nonlinear News, where I write for ambitious people with unconventional paths. Follow me for ~weekly posts on pivots, portfolio careers, and personal brands.
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I sound like a broken record every time I say this, but my favorite part of building a personal brand over the past year has been meeting people through content. I’m constantly grateful for the smart, thoughtful community that’s found me and resonated with what I share.

That’s why I’m excited to share this conversation with Andrew, who started his career in investment banking, moved into private equity, and transitioned into an operating role at a startup in London. He originally found me through content and has shared his story with me over the past year. (Small world - Andrew is also a Columbia grad who moved abroad to work in banking!)

In this conversation, we talked about how Andrew made sense of each move, what banking and PE taught him, why he started questioning the distance between his work and its impact, and what it actually looked like to try to pivot out of finance.

We also get into the less glamorous parts of the process: applying to dozens of roles, doing case studies while working full time, being seen as “too finance-y,” and learning to trust intuition over perfect analysis.

If you’re thinking carefully about your environment, motivation, and what kind of work you want to be closer to in the long run, I think you’ll find this one useful.

Early career and optionality

Hannah: How would you describe your career so far?

Andrew: I usually think about it in terms of values, because those have driven every move.

In college, I didn’t have a clear idea of what I wanted to do. I studied comparative literature and political science at Columbia, and I was interested in a lot of things, but nothing stood out as an obvious career path.

That background trained me to think critically, synthesize ideas, and connect things that are not obviously related. But when it came time to choose a job, I was worried about boxing myself in too early.

Finance felt like a place where I could build transferable skills and keep my options open. I also wanted something technical. I considered consulting, but learning how to understand businesses through financial statements and numbers felt valuable.

Banking and private equity

Hannah: What was banking like for you?

Andrew: The culture was very execution-driven. You are rewarded for saying yes, putting your head down, and doing things the established way. There is not much incentive to think creatively.

What stood out to me was how removed the work felt from actual decision-making. Even senior people were mostly pushing paper around. At the same time, I was constantly interacting with investors and felt like they were the ones actually shaping outcomes. That’s what pushed me toward private equity.

Hannah: Did private equity feel different?

Andrew: In some ways, but the core issue stayed the same.

I ended up in a niche credit investing role at Carlyle, focused on NAV lending. The work was intellectually demanding, but I still felt very far removed from the underlying businesses. We spent a lot of time writing long memos, building detailed models, and adjusting assumptions, and I kept asking myself what the real impact was.

Culturally, I also struggled with being in financial services more broadly. There is a lot of anxiety driven by fear of losing money. People tolerate difficult environments because of that fear, and over time it becomes draining.

That combination made me start questioning whether this was the right long-term environment for me.

Deciding to explore something different

Hannah: When did you start seriously exploring roles outside of finance?

Andrew: Earlier in 2025. I started pretty casually in the spring, just taking conversations and looking around, and then I really ramped things up in May and June.

Hannah: What did that process actually look like?

Andrew: Much harder than I expected. I applied to 99 jobs before signing an offer.

I completed around ten case studies, usually spending six to eight hours on each. That was honestly the most draining part of the process.

A lot of companies were very risk-averse, especially when it came to candidates switching industries. Even when I felt qualified, I could tell there was hesitation.

Hannah: Hesitation in what sense?

Andrew: Even my current company mostly hires former MBB consultants. Coming from finance, I was very aware that I wasn’t the obvious candidate. There was definitely a perception gap around whether my background would translate.

Hannah: How did you think about risk while making the switch?

Andrew: Financially, startups are obviously riskier. I tried to mitigate that by being selective about where I spent time.

I focused on companies founded by people with deep industry experience who had identified a clear gap in the market. I also cared that my current company isn’t VC-backed. It’s funded by revenue and angel investors, which made the business model feel more sustainable to me.

At the same time, staying where I was felt risky in a different way. I knew I needed to leave, even if the next step wasn’t perfectly defined.

Finding the role and positioning himself

Hannah: How did you actually find your current role?

Andrew: I took a very methodical approach on LinkedIn.

I searched for people in London with Ivy League backgrounds working in tech, not finance or consulting. A lot of people still fell into the latter categories, which made filtering easier.

When I found a company that looked interesting, I reached out to someone who was a Columbia alum. That initial conversation led to interviews.

The entire process took about four months and included multiple rounds and case studies.

Hannah: What did you learn about yourself during that process?

Andrew: Initially, I targeted strategic finance roles because they felt like the safest fit. But through the case studies, I realized I do not enjoy owning models or spending all day in Excel.

That pushed me toward broader roles like business operations or chief of staff.

The way I positioned myself was by emphasizing learning speed. I studied literature and political science, then learned finance from scratch. That story helped people feel more comfortable with the transition.

Life at a startup, careers and intuition

Hannah: How have the first few weeks been?

Andrew: The culture has been the biggest difference.

There is a strong emphasis on transparency and openness. My managers are approachable and involved, which I really value after my previous experiences.

The workload is real, but I am not working weekends, and I feel comfortable pushing back if needed.

The company is at a growth inflection point. A lot of my work is focused on revenue operations, defining our ideal customer profile, and building outbound strategy. That will be a big focus going forward.

Hannah: Looking back, what stands out about how you’ve made career decisions?

Andrew: Overthinking has never solved my problems.

Every meaningful transition I’ve made was driven by intuition. Either I was being pushed away from something that no longer felt right or pulled toward something that felt more aligned.

Trying to perfectly analyze the next step kept me stuck longer than necessary. Taking action and adjusting afterward has been far more effective.

Hannah: Looking back now, is there anything you miss about private equity or finance more broadly?

Andrew: I respect the attitude in finance of “we will get this done no matter what it takes.” My senior colleagues pushed me to my limits under this mantra, but also unlocked a sense of belief in myself despite adverse circumstances. My recent career switch is a good example of how natural it felt to push myself through rounds of interviews and case studies — I had lived experience of perseverance paying off despite some short-term pain.

Hannah: For someone in private equity or finance who’s considering a move into startup ops, what do you think they should be clear on before making that leap?

Andrew: Be honest with your intentions. Why do you want to leave your current job, and why might you thrive better in a new job? Many people in banking and PE have never had to truly question their occupational purpose, since for many IB → PE is a safe, default “path” out of college. The sooner you’re honest with yourself, the sooner you’ll find a path that truly fits you.

Also, use your company diligence skills to your advantage. As a startup employee, you’re effectively an equity investor in the business, so don’t be afraid to bring a DD list to management and grill them a bit. Good CEOs will appreciate your critical thinking, and solid answers reflect a good place to park your capital.

Trust that you’ve done enough thinking. Take action, then reflect. The answers will come quicker this way.

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