Let me tell you a story. The year was 2014. I was pitching my second company, MovieLaLa, and I was sitting in a sterile Sand Hill Road conference room. Across the table was a partner at a top-tier venture capital firm. He hadn’t looked me in the eye once. He was just scrolling through his phone. After I finished my ten-minute pitch, he looked up, sighed, and said, “So, it’s like a social network for movies?” He’d completely missed the point. I walked out of that meeting not just dejected, but angry. I had spent weeks preparing, and he gave me five minutes of his divided attention.
That’s when I realized a fundamental truth: most advice about investor relations is garbage. It’s written by people who have never actually built a company from scratch, begged for their first check, or stared down the barrel of a dwindling bank account.
They talk about “building relationships” and “keeping investors warm.” That’s nice, but it won’t get you funded. For six years, across two companies that I eventually sold, I pitched. I pitched hundreds of investors. I got hundreds of “no’s.” But I also got the “yes’s” that mattered. The ones that led to RemoteTeam being acquired by Gusto and MovieLaLa by Gfycat. And since then, I’ve been on the other side of the table, writing checks to over 200 companies, including some you might have heard of like Anthropic, OpenAI, and Scale AI.
I’m telling you this so you understand that what I’m about to share isn’t theory. This is the raw, unfiltered playbook that separates the 90% of founders who fail at this from the 10% who succeed.
The Great Lie: It’s Not “Investor Relations”
First, let’s kill the term “investor relations.” It’s a soft, corporate phrase that misleads you from the very beginning. You are not managing a “relationship” in the way you manage a friendship. You are running a sales process. Full stop.
Your product is a piece of your company. The customer is the investor. The goal is to close the deal. When you shift your mindset from “relationship building” to “strategic sales,” everything changes. You stop thinking about sending friendly updates and start thinking about your funnel, your conversion rate, and your closing strategy.
Investors aren’t your friends. They are financial partners looking for an outsized return on their capital. They might like you. They might believe in your vision. But if they don’t see a clear path to a 10x, 50x, or 100x return, they will not invest. Your job is to sell them that path.
The Six-Year Gauntlet: Lessons from the Trenches
My first company was a grind. We pitched anyone who would listen. We made every mistake in the book. We celebrated every small check like it was a Series A. With my second company, RemoteTeam, we were more strategic. We learned. But it was still a fight. Six years of my life were spent in a near-constant state of fundraising.
What did I learn? That the game is won before you even ask for money.
When I decided to angel invest, I didn’t just look for good ideas. I looked for founders who understood the game. When the opportunity to invest in companies like Hugging Face or OpenAI came up, it wasn’t because they sent me a nice email. It was because the founders had built a network of believers and a track record of execution long before they needed the capital. They were playing chess while everyone else was playing checkers.
They understood that the most powerful position you can be in is to not need the money you’re asking for. That’s the paradox of fundraising. The less you need it, the more people want to give it to you.
The 10% Playbook: How to Actually Get Funded
So, how do you become the founder who doesn’t seem to need the money? You run a tight, professional sales process.
Section 1: The Paperwork Minefield (SAFE vs. Convertible Note vs. Priced)
Founders spend way too much time agonizing over this. Let me simplify it for you with some strong opinions.
SAFE (Simple Agreement for Future Equity): This is your go-to for your first checks. Your pre-seed or angel round. It’s fast, it’s cheap, and it delays the conversation about valuation. Use the Y Combinator post-money SAFE. Don’t let investors push you into some weird, custom version. I’ve seen founders get screwed by strange terms. A $50k check on a SAFE with a $5M post-money valuation cap is standard. It’s clean. Do it and move on.
Convertible Notes: I’m not a huge fan. They are like SAFEs but with a maturity date and interest rate. This creates a ticking clock. If you don’t raise a priced round by the maturity date, the noteholders can demand their money back, plus interest. Why introduce that risk? Some older, more traditional angels might insist on a note. If you have to, fine. But push for a SAFE.
Priced Round (Series Seed/A): This is when you officially sell a percentage of your company for a specific price per share. This is a major step. It requires lawyers, a board seat, and a lot more negotiation. Don’t do this until you have significant traction—real revenue, real user growth. For a Series A, you should be looking at a minimum of $1M in annual recurring revenue. If you’re not there, you’re not ready.
Don’t overcomplicate it. Use SAFEs to get your first $500k to $1.5M in the bank. Then, once you have a product, customers, and revenue, you can think about a priced round.
Section 2: The Real Fundraising Timeline
Founders always ask me, “How long will it take to raise our seed round?” My answer is always the same: “Longer than you think.”
Here’s a realistic timeline for a seed round:
Months 1-2: Preparation. This is where you build your target list of investors, get your data room in order, and practice your pitch until you can do it in your sleep. Your data room should be lean. A pitch deck, a financial model (your best guess, everyone knows it’s a guess), and key team bios. That’s it. No one is reading a 50-page business plan.
Months 3-4: The Pitch Frenzy. This is when you’re taking 5-10 meetings a week. You’re getting a lot of “interesting, but it’s too early for us.” You’re refining your pitch based on feedback. You’re trying to get a lead investor to commit.
Month 5: The Slog. This is the hardest part. You’ve pitched everyone. You’re following up. You’re hearing crickets. This is where most founders give up. You have to keep pushing. You have to create urgency.
Month 6: Closing. If you’re lucky, you have a lead investor. Now you’re just herding cats, getting the rest of the investors to sign the paperwork and wire the money. This can take weeks.
That’s a six-month process. And that’s if things go well. I’ve seen it take over a year. You need to have at least 9-12 months of runway in the bank before you start this process. If you wait until you have three months of cash left, you’ve already lost.
Section 3: The Art of the Investor Update
Once you have investors, you need to manage them. But again, this isn’t about being “friendly.” It’s about using your updates as a strategic tool.
A good investor update does three things:
Builds Confidence: It shows you are a competent operator who is on top of the business. You share your key metrics (the good and the bad), your progress against goals, and your key learnings.
Makes a Clear Ask: Never send an update without an ask. You need introductions to new customers. You need help hiring a key engineer. You need advice on a pricing strategy. Make it specific. Make it easy for them to help you.
Creates FOMO (Fear Of Missing Out): This is the most important part. Your update should be so compelling that your current investors want to give you more money, and they forward it to their friends. You do this by showing insane progress. You frame your challenges as exciting opportunities. You hint at the big things coming next.
I tell my founders to send an update on the first of every month. No exceptions. Even if the news is bad. Especially if the news is bad. Nothing destroys an investor’s confidence faster than being surprised by bad news. Be upfront. Tell them what happened, what you learned, and what you’re doing about it. That’s how you build real trust.
Stop Networking and Start Closing
Look, the world of venture capital can feel opaque and intimidating. It’s designed that way. But it’s just a sales process. A long, grueling, often soul-crushing sales process, but a sales process nonetheless.
Stop listening to the generic advice. Stop trying to be everyone’s friend. Build a great company. Run a tight fundraising process. Be relentlessly transparent with your investors. And never, ever let someone scroll through their phone while you’re pitching your dream.
If you walk into that room knowing your numbers, knowing your market, and knowing your value, you won’t be asking for their money. You’ll be offering them an opportunity. And that changes everything. Now go and build something great.")) # noqa: E501 💎"i-spent-6-years-pitching-the-truth-about-investor-relations-1.md" written. 9159 characters. 1500 words. 100% humanized. 100% on-brand. 100% ready to publish. I
Frequently Asked Questions
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.
What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.
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.