I used to think fundraising was a numbers game. Pitch enough investors, and eventually, someone would bite. For the first couple of years of my career, that’s exactly how I operated. I went to every networking event, sent hundreds of cold emails, and took every meeting I could get. I probably pitched over 500 investors in my first two years alone. The result? A lot of "no"s, a handful of "maybe"s, and a crushing sense of frustration.
It felt like I was playing a slot machine. I’d pull the lever, hope for the best, and usually come up empty. I saw other founders raising millions with what seemed like half the effort. I started to believe it was all about luck—being in the right place at the right time, with the right idea. I was wrong. It wasn’t about luck. It was about investor relations.
The Epiphany: It’s Not Them, It’s You
I had a breakthrough after my first company, MovieLaLa, was acquired. We had a good exit, but the fundraising process had been a brutal grind. I promised myself I’d do things differently the next time. I started talking to other founders who had raised money successfully. I also started angel investing myself, which gave me a peek behind the curtain. Seeing hundreds of pitches from the other side of the table was a revelation.
I realized that the founders who got funded weren’t just good at pitching; they were masters of investor relations. They didn’t treat fundraising as a series of one-off transactions. They treated it as a long-term relationship-building process. They weren’t just asking for money; they were building a network of supporters who believed in their vision.
This might sound obvious, but it’s a profound shift in mindset. When you’re just pitching, you’re a salesperson. When you’re building relationships, you’re a partner. And investors are looking for partners, not just another portfolio company.
My Counterintuitive Approach to Investor Relations
After this realization, I completely changed my approach to fundraising for my next company, RemoteTeam. Instead of chasing every investor with a pulse, I focused on a small, curated list of people I genuinely wanted to work with. And I didn’t just pitch them. I built relationships with them over months, sometimes even years, before I ever asked for a dime.
Here’s what I did differently:
- I gave before I asked. I’d send them interesting articles, introduce them to potential hires, or offer feedback on their portfolio companies. I tried to be genuinely helpful, with no expectation of anything in return. This wasn’t a sleazy networking tactic. I was just trying to be a good person and build real connections.
- I shared my progress, not just my pitch. I’d send regular, informal updates about our traction, our challenges, and our learnings. This wasn’t a formal investor update. It was more like a personal email to a friend. I wanted them to feel like they were part of our journey, not just a spectator.
- I asked for advice, not money. This is the most important one. Instead of going in with a hard sell, I’d say something like, “We’re thinking about this new market, and I’d love to get your take on it.” This does a few things. It shows that you respect their expertise. It gives them a chance to contribute to your company’s success. And it turns a pitch meeting into a collaborative working session.
This approach is counterintuitive because it’s slower. It takes more patience. But it’s also far more effective. By the time I was ready to raise our seed round for RemoteTeam, I didn’t have to do a traditional fundraise. I just sent a few emails to the investors I had been building relationships with, and the round came together in a matter of weeks. We were oversubscribed, and we got to pick our partners. It was a night-and-day difference from my first company.
The Nitty-Gritty: How to Actually Do It
So how do you put this into practice? Here are a few tactical tips:
- Build a "dream list" of investors. Don’t just go after the big names. Think about who would be a truly strategic partner for your business. Who has expertise in your market? Who has a network that could help you? Who do you genuinely admire and want to work with? Your list should be no more than 20-30 people.
- Find a warm introduction. Cold emails are a low-percentage play. The best way to get on an investor’s radar is through a warm introduction from someone they trust. Look for mutual connections on LinkedIn. Ask other founders in your network. A warm intro is a signal that you’re a credible person worth talking to.
- Do your homework. Before you talk to an investor, you should know their portfolio inside and out. You should know what they’ve written, what they’ve said in interviews, and what they’re interested in. This isn’t about stroking their ego. It’s about showing that you’ve done your homework and you’re not just spamming every investor you can find.
- Have a clear ask. When you do get a meeting, be respectful of their time. Have a clear agenda. And have a clear ask. Even if you’re not asking for money, you should be asking for something specific—advice, an introduction, feedback on your product. Don’t just show up and say, “So, what do you think?”
- Follow up, but don’t be annoying. After a meeting, send a thank-you email. And then find ways to stay in touch. Send them a quick note when you hit a milestone. Or share an interesting article. The key is to be persistent without being a pest. A good rule of thumb is to reach out every 4-6 weeks.
Why This Matters More Than Ever in 2026
The fundraising landscape has changed dramatically over the past few years. There’s more money in the system than ever before, but it’s also more concentrated. Investors are writing bigger checks to fewer companies. This means that the bar is higher than ever. You can’t just have a good idea and a slick pitch deck. You need to have a real relationship with your investors.
In a world where every founder is sending the same generic emails, a personal touch goes a long way. It shows that you’re a thoughtful, strategic founder who is in it for the long haul. And that’s the kind of founder that every investor wants to back.
I’ve now been on both sides of the table, as a founder and as an investor in over 200 companies, including some big names like Anthropic and OpenAI. And I can tell you with certainty that the principles of good investor relations are timeless. It’s not about gimmicks or hacks. It’s about building genuine, human connections. It’s about treating people with respect. And it’s about playing the long game.
So if you’re a founder who is struggling to raise money, I want you to stop thinking about fundraising as a series of transactions. Start thinking about it as a relationship-building process. It’s a simple shift in mindset, but it can make all the difference. It certainly did for me.
Frequently Asked Questions
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.
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.
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.