Twenty Years of Betting on Founders: What I've Learned as a Fractional CFO

4 days ago

5 min read

Over the past two decades, I’ve worked with more than 30 startups across AI, SaaS, semiconductors, and adtech. Twenty-two of those companies were acquired. Two were shut down. The rest are still fighting in the best way. Along the way, I’ve been part of 12 exit teams. Those numbers mean a lot to me, but they don’t tell the whole story.

Why Fractional?

When I started doing fractional CFO work, the model wasn’t as well understood as it is today. Most people did fractional work through agencies. I didn’t see a reason to give up 30% of the fees.

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A fractional CFO is a particular kind of bet. You’re investing work and time in companies that are still becoming what they want to be. There’s nothing quite like a team that are builders and excited.

The Companies I Think About

I’ve had the privilege of working with some remarkable companies at early stages: Notion before it became a household name, Groq when it was still figuring out what a chip company could become, MyFitnessPal before Under Armour came calling, Glint before LinkedIn acquired it. And many more that most people have never heard of, because they were acquired quietly and efficiently, which is often the best possible outcome.

Each one taught me something. The semiconductor companies taught me about the particular financial requirements of building a chip company and the fab runs are expensive. The consumer apps taught me about how quickly burn can accelerate when growth metrics light up. The SaaS companies taught me revenue recognition in more configurations than I thought possible.

The CFO Nobody Talks About

Most people think of a CFO as someone who reads spreadsheets and says “no.” In a startup, the reality is far more interesting. I’ve served as a photographer : capturing a financial picture of the business so founders can see clearly where they stand. I’ve been a playground monitor: setting up the rules and processes that keep spending compliant and operations honest. I’ve been an oracle : building forecasts that help teams make decisions before the future arrives.

I’ve been a newspaper boy, chasing down the $2 that’s owed. I once helped a startup discover that their customers owed them $2 million, money the company didn’t know was sitting uncollected. We fixed the invoicing system, sent some firm reminders, and recovered it quickly.

Beyond the finances, I’ve also served as nanny: making sure employee benefits are competitive and legally compliant, because losing a great engineer to a company with better health insurance is an expensive lesson. And housekeeper: keeping the financial hygiene to survive a funding or an acquisition diligence process, which is a lot harder than it sounds when a company has been moving fast.

What Twenty Years Actually Teaches You

The financial mechanics matter: operating plans, board reporting, revenue recognition, audit readiness, cap table hygiene. But after two decades and over 30 companies, here’s what I know to be true at a deeper level:

Founders who are coachable about finance almost always build better companies. Not because financial discipline is magic, but because it forces honest conversations about what’s working, what isn’t, and how much runway you actually have.

Every acquisition is different — but the ones that go smoothly have one thing in common: someone got the house in order well before the conversation started. An acquiring company will not take on the liability of a company that isn’t well managed. The diligence on the balance sheet by IBM was an entire day for a company that was only 25 people and revenue under $1M.

The fractional model is underrated. For an early stage company, a seasoned CFO who has been on 12 exit teams and numerous rounds of funding is worth far more for 15 hours a week than a full-time hire who is experiencing most of it for the first time.

Everything Changes

The office of the CFO isn’t boring - the tech stack changes, metrics change, fundraising, and the role changes.

Long ago, people were using quickbooks and moving to Oracle or SAP. Then, people transitioned from quickbooks to Netsuite. Now, there are many modern ERP options such as Rillet . I recently used Rillet at a former client and I enjoyed seeing the automations of painful tedious work.

For expense reports, people were using paper receipts and excel. Now, modern solutions such as Ramp are far more efficient. Expense reports, corporate credit cards, and AI will make us more efficient but we need to be vigilant about security, privacy, and accuracy.

The metrics have evolved. Initially, it was the standard revenue, gross margin, and number of customers. Then, with mobile apps, it was MAU, DAU and downloads. For many years, SAAS focused on ARR - annual recurring revenue. Now, ARR means annualized run rate.

The expenses of companies have evolved as well. The top 3 expenses of many companies were people, marketing programs, and facilities - the rest was noise. For my semiconductor clients, the big expense was the fab runs. CAC became a trackable metric. Now, the big expenses are compute/tokens, people, facilities, and marketing. Facilities had once been cut down but people are returning to work.

Leadership matters. I have worked with CEOs with a variety of experiences and educational backgrounds. They have built great companies. The only thing that they have in common is great leadership: clear vision, strong moral compass, and self discipline. They also have a great team… Great marketing, sales, customer success, and people leaders will make a significant difference.

What I’d Tell a Founder Today

Get a CFO earlier than you think you need one. Not because you’re in trouble — but because having someone who has seen this movie before, sitting in your corner and watching for the cliffs, changes the quality of every decision you make. You don’t have to hire them full-time. You don’t have to sign a long-term contract. But do not treat your finances as something to figure out later.

Not having your finances in order is planning to fail.

Twenty years in, I still believe in founders. I still get excited when a company is six people with a big idea and a blank spreadsheet. The work hasn’t gotten old because the founders haven’t gotten old — every cohort brings a new set of problems I haven’t seen in exactly that configuration before.

That, more than any acquisition or exit, is what keeps me going.