The biggest lie in Silicon Valley is that fundraising is a quick process. It’s not. Not even close.
I’ve spent the better part of a decade in the fundraising trenches. First, as a founder raising money for my own companies, RemoteTeam and MovieLaLa. We went through the whole circus – pre-seed, seed, Series A. I’ve pitched hundreds of VCs, gotten hundreds of “no’s,” and thankfully, a few critical “yes’s” that led to two successful exits.
Now, I’m on the other side of the table. As an angel investor, I’ve written over 180 checks to companies like Anthropic, OpenAI, Scale AI, and Hugging Face. I see hundreds of pitches a year. And after reviewing over 500 of them, I’ve noticed a glaring pattern. The founders who succeed, the ones who build massive, world-changing companies, think about fundraising completely differently than everyone else.
They don’t just show up with a deck and a dream a few weeks before they run out of money. They understand that fundraising is a process, not an event. And that process starts months, sometimes even years, before they ever ask for a dollar.
The Myth of the 3-Month Fundraise
Every founder has heard the story. The one about the hot startup that raised a massive round in a few weeks with a dozen term sheets. It makes for a great headline, but it’s a dangerous fantasy. It sets a completely unrealistic expectation for 99% of founders.
The reality is that a typical fundraise takes six to nine months. And that’s if things go well.
Let’s break down the math. It takes time to prepare your materials, research investors, get warm intros, and actually have the meetings. Each conversation can take weeks to schedule. You’ll have multiple meetings with the same firm, talking to different partners. Then comes due diligence, which can be a grueling, month-long process. And finally, you have to negotiate the term sheet and get the money in the bank.
I’ve seen so many founders fail because they underestimate this timeline. They start fundraising when they have three months of runway left, thinking it’s plenty of time. They’re wrong. By the time they realize how long it’s actually going to take, they’re desperate. And desperation is a terrible negotiating position.
How the Top 1% Play a Different Game
The top 1% of founders don’t fundraise. They build relationships.
They’re not just reaching out to investors when they need money. They’re building a network of potential partners long before they ever think about asking for a check. They’re providing value, sharing updates, and building trust. So when it’s time to raise, it’s not a cold outreach. It’s a warm conversation with someone who already knows them, respects them, and is excited about what they’re building.
I remember when I was raising for RemoteTeam. I had been sending monthly updates to a handful of investors for over a year. Not just the good news, but the challenges too. I was transparent and authentic. When we decided to raise our seed round, I sent an email to that list. Within a week, we had three term sheets. We closed the round in less than a month. It looked like an overnight success, but it was the result of a year of consistent, deliberate relationship-building.
This is the single biggest differentiator between the founders who struggle and the ones who succeed. The ones who struggle think of fundraising as a transactional process. The ones who succeed think of it as a relational one.
The Art of the Investor Update
So how do you build these relationships? It’s simpler than you think. You send investor updates.
An investor update is a short, concise email that you send to a curated list of potential investors every month or two. It’s not a sales pitch. It’s a way to share your progress, ask for help, and stay on their radar.
Here’s what a good investor update includes:
- A quick summary of your progress. What are your key metrics? How have they changed since your last update?
- Your biggest wins. Did you land a major customer? Ship a new feature? Hire a key employee?
- Your biggest challenges. What are you struggling with? What are you trying to figure out?
- An ask. Is there someone you’d like an introduction to? Are you looking for advice on a specific problem?
That’s it. It shouldn’t take you more than 30 minutes to write. But it’s the single most valuable thing you can do to de-risk your next fundraise.
Your Fundraising Timeline Starts Now
If you’re a founder, your next fundraise has already begun. It doesn’t matter if you’re not planning to raise for another year or two. The work you do today will determine whether you’re in a position of strength or a position of weakness when it’s time to ask for money.
So start building those relationships now. Identify a handful of investors who you’d love to work with. Add them to a list. And start sending them updates. Be consistent. Be authentic. And be patient.
Fundraising is a marathon, not a sprint. The founders who understand that are the ones who will be left standing in the end. They’re the ones who will have the capital they need to build enduring, iconic companies. And they’re the ones who will have the freedom to build on their own terms, without being at the mercy of the fundraising cycle.
Don’t be the founder who runs out of time. Be the founder who plays the long game. Your future self will thank you for it.
Frequently Asked Questions
Do all experts agree with this view?
No, and that's fine. The best ideas in business are often contrarian. I share my perspective based on my experience and data, but I encourage you to seek out opposing viewpoints and form your own conclusions.
What's the most common pushback you get on this?
People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.
How has this view evolved over time?
My thinking on most topics has changed significantly over the years. Early in my career, I held many conventional views that experience proved wrong. I try to update my beliefs when the evidence changes.
How can I apply this thinking to my own situation?
Start by identifying the core principle behind the opinion, not the specific example. Then ask yourself: does this principle apply to my context? If yes, test it in a small, low-risk way before going all in.