I’ve worn multiple hats in my career—from founder to investor. Over the years, I’ve built four companies and taken an active interest in startups, not just as an investor but as someone who genuinely enjoys being part of the journey.
Being a founder comes before being an investor for me, and every venture is an opportunity to bring something valuable beyond the check.
TL;DR
Angel investing can be more impactful when investors bring added value through experience, mentorship, and connections.
Both founders and investors benefit from networks built on trust.
Clear outreach and frequent updates help founders build lasting, productive relationships with their supporters.
Here are a few principles and lessons from my journey that I think are worth sharing with founders and investors alike.
It’s About Adding Value Beyond the Check
As a founder, I didn’t immediately see myself becoming an investor. I started angel investing to gain a return, but also to bring value to the startups I supported. After my first company sale in 20082010, I did four to five deals a year. But as time passed, I realized that pure financial gain wasn’t enough. The real value was working with startups where I could contribute more than just money.
I scaled back my investment pace significantly, focusing on startups where I could help with my experience in business development, sales, and fundraising. For me, the ideal scenario is where I can offer my network and guidance—essentially, being a contributor rather than just a name on the cap table.
Selecting Startups to Back
The most valuable investments come down to people and relationships, not balance sheets and forecasts.
When it comes to choosing where to invest, I’m not interested in a set thesis or sector-focused strategy. My approach centers around relationships and personal connections. For instance, my involvement with Daytona came from a deep trust in Ivan and a strong belief in his vision. I did my own homework, consulting technical friends who vetted the product, but it was ultimately my relationship with Ivan and his network of developers that made the decision for me.
Here’s what I consider before investing:
Relationships: I invest in people I trust and respect. If I’m confident in the founder’s character and capabilities, that’s often the deciding factor.
Network: A strong network is everything. Referrals and recommendations mean a lot to me, especially when they come from industry insiders I trust.
Track Record: I don’t need every founder to have a perfect record, but experience does help. I look for founders who understand their industry, even if they’ve had past failures.
Reaching Out to Investors
The best connections are often serendipitous – it’s about being authentic and showing your value upfront.
Founders often ask how to approach investors like me. Truthfully, it’s a mix of timing, authenticity, and relevance. When reaching out, it’s crucial to be concise, respectful, and, most importantly, clear about the ask. Here’s what I recommend:
Do Your Homework: Understand the investor’s background, interests, and portfolio before making the approach. Tailoring your message shows that you respect their time.
Make Your Ask Forwardable: When asking for an introduction, write a new, cleanyour email in a way that can be forwarded directly. I can’t hit forward on an email chain that goes back and forth with you for the last 2 weeks, and obligating the person you’re already asking for an intro also to write an email from scratch is tacky. Plus, they are unlikely to articulate your pitch as well as you. It sounds simple, but it’s a fine art that so many founders still get wrong all the time. Abut a clear, forwardable message makes all the difference in getting an intro or being ignored.
Know Your Audience: Not every investor is going to be the right fit. Sometimes, it’s about finding the right people within an organization who are genuinely aligned with what you’re building.
The Value of Regular Updates
Bugging your investors isn’t a bad thing – as long as you’re respectful, regular updates can lead to new connections and opportunities.
One of the most underrated tools a founder has is the investor update. When founders provide consistent updates, they’re amplifying their network and keeping supporters engaged. I’m a firm believer that frequent, brief updates with clear requests for support can lead to unexpected benefits. Here’s why:
Keeps Investors Engaged: Even if an investor can’t always help, staying top-of-mind is valuable.
Increases Visibility: Regular updates mean you’re actively reminding people in your network of your progress, making it easier for them to connect you when opportunities arise.
Fosters Trust: Transparency shows that you’re committed to the relationship, not just the funding.
Lessons from the Trenches
A single thoughtful connection can be worth more than a dozen poorly prepared introductions.
As someone who’s received countless pitches and introduction requests, I’ve seen firsthand where founders can misstep. Avoid these common pitfalls:
Failing to Prepare the Intro Request: When requesting an intro, make it easy for your contact to help you. A vague or poorly structured request will likely end up ignored.
Unrealistic Expectations: If you’re reaching out for support, be realistic about what you’re asking for. Just because I’m connected on LinkedIn doesn’t mean I can reach out to every contact at a moment’s notice.
Ignoring Follow-Ups: If you ask for help, follow through. Too many founders ask for support and then go silent.
Conclusion
Navigating the startup world as a founder or investor is about more than just financial returns. It’s about building genuine, lasting relationships that add real value to both sides. For founders, this means not being afraid to reach out and make requests, but also understanding the balance between asking for help and respecting the time and efforts of others.
To create partnerships that support long-term growth, keep your lines of communication open, provide regular updates, and ensure that every ask is thoughtful and purposeful. Each interaction is an opportunity to bring others into your journey, building a support system that’s invested in your success as much as you are.
In the end, the strongest networks are those built on trust, respect, and clear, authentic connections.
