Fourteen. That’s how many times I failed to raise money before I figured out what I was doing wrong. Fourteen times I put together a pitch deck, built a list of investors, and sent out emails, only to be met with a wall of silence. It was a brutal, soul-crushing experience. And it taught me a lesson that I’ll never forget: most of what you read about investor relations is complete and utter garbage.
I’m not saying that to be controversial. I’m saying it because it’s true. I followed all the advice. I read all the blog posts. I even paid for a course on fundraising. I was doing everything “by the book.” And it got me nowhere. It wasn’t until I threw the book out the window and started thinking for myself that I finally started to see results.
In this post, I’m going to share with you the hard-won lessons I learned from those 14 failures. I’m going to tell you what actually works when it comes to getting investors to pay attention to you. And I’m going to give you a simple, no-BS framework that you can use to raise money for your own startup. This isn’t theory. This is what I’ve learned from being in the trenches, as a founder who has raised millions of dollars and had two successful exits, and as an angel investor who has backed over 200 companies, including some of the biggest names in tech.
The Siren Song of “Investor Relations”
When you’re a first-time founder, it’s easy to get seduced by the idea of “investor relations.” It sounds so professional, so… official. You imagine yourself schmoozing with VCs at fancy parties, building deep, meaningful relationships that will eventually lead to a massive seed round. The reality is a lot less glamorous. It’s a lot of unanswered emails, a lot of awkward coffee meetings, and a lot of self-doubt.
The fundamental problem with the traditional approach to investor relations is that it’s based on a false premise: that you need to build a relationship with an investor before they’ll invest in you. This leads founders to waste countless hours on activities that have a very low ROI, like sending out monthly newsletters, trying to get “warm intros” from tenuous connections, and generally trying to force a relationship that isn’t there.
I fell into this trap myself. With my first company, I spent months trying to build relationships with investors. I created a spreadsheet of 100 VCs, and I systematically worked my way through the list. I sent personalized emails, I commented on their blog posts, I even flew to Silicon Valley to try and meet them in person. The result? A handful of polite “no’s” and a whole lot of radio silence. It was a massive waste of time and energy. And it almost killed my company.
The Hidden Costs of Chasing Investors
What they don’t tell you about fundraising is that it has a lot of hidden costs. It’s not just the time and money you spend on pitch decks, travel, and legal fees. It’s the emotional toll it takes on you as a founder. The constant rejection, the feeling of being judged, the pressure to be “on” all the time – it’s exhausting. And it can have a serious impact on your mental health.
I remember one particularly brutal week when I had three investor meetings in a row. The first one was with a well-known VC who spent the entire meeting checking his phone. The second one was with a partner at a big firm who told me my idea was “a vitamin, not a painkiller.” And the third one was with an angel investor who seemed genuinely interested, but then ghosted me after I sent him my deck. I came home that Friday feeling completely defeated. I started to question everything – my idea, my abilities, my decision to become an entrepreneur. It was a dark time.
But the biggest hidden cost of fundraising is the opportunity cost. Every hour you spend chasing investors is an hour you’re not spending on your product, your customers, or your team. And in the early days of a startup, that’s a trade-off you can’t afford to make. You need to be laser-focused on building a great business. Everything else is a distraction.
My 14 Failures: A Post-Mortem
Looking back, I can see exactly what I was doing wrong. My first few attempts were just embarrassing. I was sending generic, mass emails to investors I didn’t know, with a pitch deck attached. I was lucky to even get a response. Then I got a little smarter. I started personalizing my emails, referencing their portfolio companies and their investment theses. I even managed to get a few meetings. But I still couldn’t get anyone to bite.
Why? Because I was focused on the wrong thing. I was so obsessed with trying to impress investors that I forgot about the most important thing: building a great business. My pitch was all about the massive market opportunity and the amazing team I had assembled. But I didn’t have any real traction to back it up. I had a few vanity metrics, but nothing that showed I had a real, sustainable business.
My 14 failures weren’t really 14 distinct events. They were a series of painful learning experiences that all pointed to the same conclusion: investors don’t invest in ideas, they invest in traction. They want to see that you’ve built something that people want, that you have a clear path to profitability, and that you’re the right person to lead the company. Without that, all the schmoozing in the world won’t get you a check.
The Turning Point: From Zero to Acquired
The turning point for me came with my second company, MovieLaLa. We were building a social network for movie lovers, and we were struggling to get investors interested. We had a decent product and a small but passionate user base, but we weren’t growing fast enough to get VCs excited. We were on the verge of running out of money when we got an unexpected offer from Gfycat, a well-funded startup in a related space. They wanted to acquire us.
It wasn’t a life-changing exit, but it was a real outcome. And it completely changed the dynamic with investors. Suddenly, the same VCs who had ignored my emails for months were now calling me, asking for a meeting. They wanted to know what I was working on next. They saw the acquisition as a signal that I was a founder who could build something of value. It was a powerful lesson. The best way to get investors interested in you is to build something that someone else wants to buy.
I had a similar experience with my next company, RemoteTeam. We were building a platform to help companies manage their remote teams. We were growing quickly, but we were still having trouble getting the attention of top-tier VCs. Then, we got an acquisition offer from Gusto, one of the fastest-growing companies in Silicon Valley. The deal was a game-changer for us. And it opened doors that had previously been closed. The Gusto acquisition was a massive validation of what we were building. And it made it much easier to raise money for my next venture.
A New Framework for Investor Relations
After these experiences, I developed a new framework for investor relations. It’s simple, it’s effective, and it’s based on one core principle: show, don’t tell. Instead of telling investors how great your company is, show them with your traction. Here’s how it works:
Focus on the metrics that matter. Forget about vanity metrics like website visits and Twitter followers. Focus on the metrics that actually drive your business, like revenue, customer growth, and engagement. And be honest about your numbers. Don’t try to spin them to make them look better than they are. Investors will see right through it.
Communicate with investors like a CEO. When you do communicate with investors, be direct, be concise, and be professional. Don’t waste their time with long, rambling emails. Get straight to the point. And always include a clear “ask.” What do you want from them? An introduction to a potential customer? Feedback on your product roadmap? Be specific.
Build a “permissionless” relationship. Don’t wait for investors to give you permission to build a relationship with them. Start adding value from day one. Send them interesting articles, introduce them to talented people in your network, and offer to help their portfolio companies. Be a giver, not a taker. And don’t expect anything in return. The goal is to build a reputation as a smart, helpful founder who is always looking for ways to add value.
Create a “no-brainer” investment opportunity. The best way to get an investor to say “yes” is to make it a no-brainer. That means having a great team, a huge market, a differentiated product, and a ton of traction. It also means having a clear and compelling vision for the future. You need to be able to paint a picture of what the world will look like when your company is successful. And you need to be able to convince investors that you’re the right person to make that vision a reality.
The Bottom Line
Investor relations isn’t rocket science. But it’s not easy, either. It takes a lot of hard work, a lot of persistence, and a lot of resilience. But if you focus on the right things, and you follow the simple framework I’ve outlined in this post, you can dramatically increase your chances of success.
Remember, investors are just people. They’re looking for the same thing you are: an opportunity to be a part of something great. So go out there and build something great. And when you’re ready, the investors will be there, waiting for you. And if you're one of the lucky ones, you might even get to invest in the next Anthropic or OpenAI. I did, and it all started with those 14 failures.
Frequently Asked Questions
How long did it take to see results?
Most meaningful business results take 3-6 months to materialize. Anyone promising overnight success is selling something. The companies in my portfolio that grew fastest were the ones that stayed patient and consistent.
Can these results be replicated?
The specific numbers will vary, but the underlying patterns and principles are transferable. The key is understanding the context behind the results, not just copying the tactics. Every company has unique constraints that shape what works.
What would you do differently looking back?
I'd move faster on the things that were working and cut the things that weren't sooner. Most founders, myself included, hold onto failing strategies too long because of sunk cost. Speed of learning is everything.