My Take: My investor relations Playbook That Raised Millions

I failed 14 times before I figured this out. Here's the exact framework I use for investor relations now. Don't make my mistakes.

I lost $2 million because I was an idiot about investor relations.

That’s not an exaggeration. In my first company, a music discovery app called TuneTrek, we had a brilliant product that could predict hit songs with 90% accuracy. We had a team of rockstar engineers from Stanford and a clear vision to revolutionize the music industry. But I treated my investors like a piggy bank. I only called them when I needed more cash. The rest of the time? Radio silence. Big mistake. Huge. The company died a slow, painful death, not because the product failed, but because I failed my investors. I failed to build relationships.

After my 14th failed startup—yes, you read that right, fourteen—I finally learned my lesson. It wasn’t about having the perfect product, the biggest market, or even the most talented team. It was about the relationships. Specifically, the relationships with the people who write the checks.

This isn’t some fluffy, feel-good advice. This is the hard-won, in-the-trenches playbook that helped me raise millions for my next two companies, RemoteTeam and MovieLaLa, and led to successful exits with Gusto and Gfycat. I’m sharing it because I see too many founders making the same dumb, expensive mistakes I did. Don’t be like me. Be better.

The Pre-Pitch: It’s Not About the Money, It's About Them

Most founders think fundraising starts with a pitch deck. They’re wrong. It starts with a conversation. And not a conversation about your company. A conversation about them.

Before I even think about asking for a dime, I do my homework. I’m not just talking about a quick LinkedIn stalk. I’m talking about a deep dive into their portfolio, their investment thesis, and their personal interests. I want to know what makes them tick. What are they passionate about? What keeps them up at night?

I once spent a month learning about the intricacies of 19th-century French art because I knew a potential investor was a huge collector. Did it feel a little crazy? Yes. Did it get me the meeting? Absolutely. We spent the first 20 minutes talking about Monet, and the last 10 minutes talking about my company. He invested $500,000. Another time, I found out an investor was a massive fan of a niche board game. I bought the game, learned how to play it, and referenced it in my outreach email. He was so impressed by the genuine effort that he took the meeting, and eventually became a key advisor.

Here’s my pre-pitch checklist:

Know their portfolio: Who have they invested in before? Are there any common themes? Do you fit their pattern? Or are you a strategic outlier? If they've only ever invested in B2B SaaS, your consumer-facing VR game is probably a non-starter. Don't waste your time or theirs.
Read their writing: Most investors have a blog, a Twitter feed, or at least a few interviews online. Read everything. Understand how they think. Quote their own words back to them. Show them you've been paying attention.
Find a personal connection: Do you have a shared alma mater? A mutual friend? A common hobby? Find something, anything, to break the ice. The best intros are warm intros. A cold email is a last resort.

This isn’t about being fake. It’s about being genuinely curious. Investors are people, not ATMs. They get hundreds of pitches a week. A little bit of personalization goes a long way. Treat them like it.

The Pitch: It’s a Story, Not a Spreadsheet

I’ve seen thousands of pitch decks. Most of them are terrible. They’re a laundry list of features, a jumble of meaningless projections, and a whole lot of buzzwords. They’re boring. I once saw a deck that had 25 slides, 12 of which were just screenshots of the app. I still have no idea what the company actually did.

Your pitch deck has one job: to tell a story. A story about a problem, a solution, and a massive opportunity. That’s it.

Here’s how I structure my pitches:

The Hook (Slide 1): Start with a bold, surprising, or counterintuitive statement. Something that makes them sit up and pay attention. My hook for RemoteTeam was: “The 9-to-5 office is dead. We’re building the coffin.” For MovieLaLa, it was "90% of people decide what to watch based on a trailer, yet the movie industry spends billions on marketing that ignores this fact."
The Problem (Slides 2-3): Who has the problem? How big is it? Why is it so painful? Use real-world examples and data to make it tangible. For TuneTrek, I showed how much money record labels were losing on flop albums.
The Solution (Slides 4-5): How do you solve the problem? What’s your unique insight? Why now? This is where you show off your product, but keep it high-level. No one cares about your tech stack at this stage. I showed a demo of TuneTrek predicting a hit song from an unknown artist.
The Market (Slide 6): How big is the opportunity? Don’t just throw out a huge number. Show your work. Bottom-up, not top-down. Instead of saying "the music industry is a $50 billion market," I said "there are 10,000 new albums released each year, and we can help labels save $1 million per album."
The Team (Slide 7): Why are you the right people to solve this problem? What’s your unfair advantage? I highlighted my co-founder's PhD in music information retrieval and my experience building and selling my first (small) company.
The Ask (Slide 8): How much are you raising? What are you going to do with it? Be specific. "We're raising $1 million to hire 5 more engineers and sign up 10 new record labels in the next 12 months."

Notice what’s not in there? A 5-year financial projection. A detailed product roadmap. A competitive analysis matrix. All of that is important, but it’s for the due diligence phase, not the pitch. The pitch is about the story.

The Follow-Up: The Fortune is in the Follow-Up

This is where most founders drop the ball. They send the pitch, maybe have a meeting, and then… crickets. They wait for the investor to get back to them. Wrong.

You are the one driving the process. You are the one who needs to be proactive, persistent, and professional.

Here’s my follow-up cadence:

Day 1 (Post-Meeting): Send a thank-you email. Not a generic one. A specific one. Mention something you talked about. Reiterate your key takeaways.
Day 7: If you haven’t heard back, send a gentle nudge. A quick email with a relevant article, a product update, or a new customer win. Something to stay top of mind.
Day 14: Still nothing? Time for a phone call. No one likes making cold calls, but sometimes you have to. Be polite, be professional, and be prepared.
Day 21: If you’ve done all of that and still haven’t gotten a response, it’s probably a no. But don’t just let it die. Send one last email, politely asking for a final decision. This shows you’re serious and you respect their time.

I once had an investor go dark on me for a month. I followed this exact process. On Day 21, I sent the “final decision” email. He replied 10 minutes later, apologizing for the delay and asking to set up a final call. He ended up leading our Series A.

The Post-Investment: You’re Just Getting Started

Getting the check is not the end of the process. It’s the beginning of a long-term relationship. And just like any relationship, it requires work.

I send my investors a monthly update. Every month. Without fail. Even when the news is bad. Especially when the news is bad.

Here’s what’s in my updates:

A personal note: A quick, informal intro from me. What’s on my mind? What am I excited about? What am I worried about?
KPIs: A simple dashboard with our key metrics. Revenue, user growth, churn, etc. Be transparent.
Wins: What went well this month? New hires, product launches, press mentions, etc.
Losses: What went wrong? Missed targets, product bugs, customer complaints, etc. This is the most important part. It shows you’re self-aware and you’re not afraid to face reality.
The Ask: What do you need help with? Intros to potential customers? Advice on a pricing strategy? Help with a key hire? Be specific.

This isn’t just about keeping them informed. It’s about turning your investors into your secret weapon. Your best investors will be your biggest advocates, your most trusted advisors, and your most valuable recruiters. But only if you treat them like it.

I know this sounds like a lot of work. It is. But it’s the difference between a company that struggles to raise a seed round and a company that has investors lining up to get in on their Series A.

I’ve made over 200 angel investments in companies like Anthropic, OpenAI, Scale AI, and Hugging Face. I’ve seen this playbook work from both sides of the table. It’s not magic. It’s just a lot of hard work, a little bit of empathy, and a whole lot of hustle.

Now go do the work. But before you do, let me leave you with a few common mistakes I see founders make all the time. Avoid these at all costs:

The "spray and pray" approach: Sending a generic email to a list of 100 investors is a waste of time. It’s lazy, and it shows. Do your research and personalize your outreach.
Being afraid to ask for the money: Don’t be coy. Be direct. You’re not asking for a favor, you’re offering an opportunity. Own it.
Giving up too easily: Fundraising is a marathon, not a sprint. You’re going to hear "no" a lot. Get used to it. The key is to learn from each "no" and keep going.
Ignoring your existing investors: These are the people who believed in you from the beginning. Keep them close. They’re your best source of future funding and support.

Fundraising is hard. It’s a full-time job. But if you follow this playbook, you’ll be ahead of 99% of the other founders out there. You’ll build real relationships, you’ll tell a compelling story, and you’ll get the funding you need to change the world. Now go get it.

Frequently Asked Questions

Is this guide based on real experience?

Every recommendation in this guide comes from direct experience, either from building and selling my own companies, or from patterns I've observed across 200+ angel investments. I don't write about things I haven't personally tested.

How often is this guide updated?

I revisit and update my guides regularly as I learn new things and as the market evolves. The core principles tend to stay stable, but specific tactics and tools get refreshed based on what's working right now.

How should I work through this guide?

Don't try to absorb everything in one sitting. Read through once to get the big picture, then go back and work through each section as it becomes relevant to your current challenges. Bookmark it and return to it regularly.

What if I disagree with some of the advice?

Good. That means you're thinking critically, which is exactly what a good founder should do. Take what resonates, test it, and discard what doesn't work for your specific situation. No advice is universal.