5. 2. 2025
10 min read
From Wall Street to Silicon Valley
Bringing you another insightful summary from The Startup Huddle podcast. In this blog post, Casey Woo, a Harvard-educated CFO/COO, founder, and investor known for his work with startups like WeWork, shares his expertise on the critical roles of finance and operations in startups and the strategic insights and business intelligence they provide. Find out how it can help you make better decisions and keep your startup on the right track.
Silvia Majernikova
Social Media Marketing Manager
Casey Woo left Wall Street to join a ten-person startup in Silicon Valley. Despite facing initial challenges, he eventually became the CFO and COO of several high-growth startups and raised over $600 million in debt and equity. Additionally, Casey founded FOG Ventures, a VC investing in early-stage startups, and co-founded Operators Guild, a community of the most talented company builders (CFO, COO, Biz Ops, CoS, early founders) in the world—sharing best practices through some of the highest engagement stats of any professional group.
What inspired your journey from Wall Street to Silicon Valley? Did you feel welcome there?
While I was on top of the totem pole of Wall Street, I had friends calling: How do I get into Wall Street? How do I become a hedge fund investor? I started to get bored. This is not because investing is boring; it's a very challenging, interesting job. I realized that I got bored because I missed my team. Being by myself in an office is lonely. And the second thing is I wasn't building anything. As an investor, you buy, sell, sell, buy, buy, sell. So, after 10 years, I took a big pay cut and joined a 10-person start-up in Silicon Alley in New York, and I loved it. I loved it so much that I told my wife, hey, I want to go where the best in the world are regarding tech. It's not New York; it's San Francisco, and that's where the really interesting stuff happened. I was not welcomed.
People that I spoke to didn't value finance. They saw it as budgeting or my expense report. There are only three first-class citizens. The first one is the people who fund - VCs. The second are the people who build it, product & engineering. The third is the people who sell it in sales and marketing. I didn't say finance, HR, talent, legal, IT, or ops; those are considered back office. It was hard to come in and try to add value or even explain to some of what I do. Our titles didn't even match what we did. I was called VP of Finance and BizOps. My expectations were surprisingly underwhelmed, and it was a tough transition.
What sparked the shift in Silicon Valley founders recognizing the need for strong operators?
It's a combination of things. One of them was the speed at which companies get built; it gets faster and faster and more complicated. And whenever you have speed, you have scaling issues. So finance matters a lot. People matter a lot more. So that was one of the things that made startups get more complicated fast, and you needed this operator to help keep it together.
The second is the DNA changed. More and more bankers and consultants from what I call the business side float into finance and operations. So when you have me versus more of a standard of someone from accounting or a controller, it's a very different approach. We're generally more into the business. We ask a lot of business questions. We forecast that we partner a lot with sales and marketing, which is not normally what a traditional CFO does. They're more on compliance and forecasting. So you have an increasing speed of business and the need for scalers to be there, and then you have this new breed where people see it.
Then the third is data. When you have data, you have insights. When you have insights, you have intelligence. When you have intelligence, you can add value. Systems and tools around the CFO have gotten so good now. We can provide that value that people value. The world of startups has gotten more sophisticated in terms of financial metrics and measurement and ROI, not just accounting. So all that combined has grown for over ten years, what I call the rise of the operator, and there's still more to go, but people get it now.
What’s been your most interesting CFO experience, and how has the role evolved with new technologies?
The most interesting one is WeWork - the speed at which we were building a physical business, not software. I love WeWork because it's a people business. I love WeWork because we would bring beautiful office space to people. I wasn't the CFO, so to be clear, but I was pretty senior. I got a lot of the joy of the building. I didn't have to fundraise the learnings of what happens at scale, what works, and what doesn't, without dealing with the politics and the crazy that everyone knows about. We built that scale; we were global. I had Chinese partners, Brazilian partners, and European partners. I loved that community, and the other one was talent. You bring in some of the best talent when you're a name-brand company.
How it's changed with new technologies is that the office of the CFO is becoming the Office of Business Intelligence, or someone coined it, Chief Performance Officer. We have more and more data integrated. We can finally access insights quickly. Whereas before, it took forever. Finance is one of the only functions that sees everything. I'll say it again. Finance is one of the only databases and functions that sees everything. Money flows through everything. What does that mean? That means before or 10 years ago, most of the data and intelligence sat under product engineering. Now it's all Stripe, Rippling, it's all there for me. And we've gotten so advanced that non-technical people can access the data. What about the return on the customer? That's even as important. The CFO office is gonna become very strategic.
At what stage do you think a startup needs a CFO to handle business intelligence?
If you have a "CFO," I think it's generally when you're getting closer to being public or when you have significant fundraising investor relations because it's very strategic. A lot of it has to do with investors. It's more of a political job than an operating doer job. At an early stage, you call it VP of Finance; you can call it CFO, but what they do is very different depending on the stage. The early stage is about building and fundraising. It's about building and measuring the metrics. At that stage, you should be insightful and business-intelligent. That shouldn't be something when you have a lot of money and a size, have a big operation, and need to split the duties, like dealing with investors or the board, right? Then, you need someone more senior, and you call them CFO. They can do everything, but that's not the best use of their time. Let me replace the CFO with strategic finance. The role of strategic finance should start early because the CFO of Google versus the CFO of Series B is different. Finance should be strategic early. So the answer is any head of finance should be doing strategic intelligence work at every stage.
Can you share the story behind starting Operators Guild, where it stands today, and the activities it focuses on?
OG, which stands for Operators Guild, is the organization I created that I wanted for myself. So there's 10 people in a lunch group that I met eight years ago who were operators like me lost that whole story about no one knowing what to do with us and I said, hey, would you guys want to create like a moms group, dad's group for operators where we meet every month and help each other. There were five rules. No promotion or solicitation. Give more than you get. Leave your ego at the door. What's said here stays here, and operators own, and that 10 is now 700. It was 98% word of mouth. So, what is the operator? We have four personas - CFO, COO, ops, Vizops, and strategy and early-stage founders. We're one of the most engaged and active communities in the world when it comes to a professional network.
Regarding activities, we have an incredibly active email form, Q&A form, where you get immediate, real-time, actionable, quality answers because you sit on top of 10,000 years of experience. That experience is not replicable. So that's number one. The second is social events. We host local dinners or summits, where we help support, talk, network, and make friends with other operators. So, the good old in-person friendships and relationships. The third is a bunch of stuff that I'll just call professional development. We have master classes taught by the best coaches or experts. If it's international expansion, we have experts there. So we become the home for whatever topic is relevant: job opportunities, networking, and, of course, investing.
I would love OG to become the global community for the world's best company builders in high-growth VC-backed companies.
You also founded Fog Ventures - can you share your investment thesis, the kinds of companies you focus on, and your typical investment size?
We're interested in C through B, pre-product, and post-product. We have two types of avenues. Number one is an operator tool. The test is whether someone in operations—such as G&A, finance operations, business operations, strategy, CEO, or COO—would purchase the product. So it could be compliance, it could be finance, it could be workflows. The other is FogX. FogX is any other company that cares about operators. There are crypto companies and e-commerce. Our specialty is operator tools because we are the buyer. The average check size is 200,000 - 400,000. We have about 30 to 50 operators in every deal. I'm most proud of a 100% track record across all 15 companies regarding CEOs who have given us the highest rating.
Why do you think your portfolio companies rate you so highly, and what value do you provide beyond funding?
Our biggest value is in terms of live demos. We've done over 1400 live demos. If you're in the sales business, getting in front of a decision-maker for 60 minutes, your pitch is very valuable. We can create 80 of those in a heartbeat. So, number one is demos. Number two is feedback. We write back a lot of feedback on the product and the go-to-market strategy, so that's invaluable. Most of the time, when you're pitching one-on-one, no one's giving you feedback on your sales page, right? And the other's advisory. So after we invest, we become your advisor set.
As a founder and someone who works closely with many founders, what defines the ideal founder profile?
I think it is a true passion for whatever you're building. Some founders start something to start something, and some people start because they believe in something. The other is hard work. I know many smart people, but hard work is the difference between smart people and successful people. Then, it is confidence. Founders should have some confidence or delusion, whatever you want to call it, because you must be a little crazy. Otherwise, someone else would have done it already, right? As I just got to like Elon Musk, I remember him saying, "I just wanted to start Tesla, so people realize that electric cars could be cool." Just this passion makes cool founders and long-standing, lasting businesses.
Have these handpicked highlights sparked your curiosity? You won't want to miss the full conversation with Sam Showering on our YouTube channel or your favorite platform. The episode dropped on April 18th, 2023.
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