What Adrian Vanzyl Wishes He Knew Before His First Angel Check
Nearly every experienced investor has a story about an early mistake. Adrian Vanzyl is no exception. Looking back at his first angel investments, he’s candid about what he got wrong. More importantly, he’s clear about what those early mistakes actually taught him.
This matters because most angel investing advice comes from people who’ve already forgotten how confusing the first few checks feel. As a result, the lessons that actually help beginners rarely get written down honestly.
Why the First Check Feels Deceptively Simple
Writing a first angel check often feels straightforward. You like the founder, you like the idea, and you write a check. However, that simplicity is misleading. Behind a decision that takes an afternoon sits years of pattern recognition. Experienced investors have built this up, often without realizing how much they’re relying on it.
New investors don’t have that pattern library yet. Consequently, they tend to substitute something else in its place. This might be excitement about the product, comfort with a familiar-sounding pitch, or simple enthusiasm for the founder’s energy. None of these are useless signals. Still, none of them are substitutes for real diligence either.
The Mistake of Falling in Love With the Product
One of the most common first-time mistakes is investing in a product you personally find exciting. This differs from investing in a business you’ve actually evaluated. A slick demo or a clever feature can create real emotional pull. Unfortunately, that pull has very little to do with whether the underlying business will work.
Adrian Vanzyl has been candid about learning this the hard way. A product can be genuinely impressive and still sit inside a business with no real path to distribution. It might also lack a defensible advantage or a credible plan for revenue. Falling for the product first, and asking the harder business questions second, is a pattern almost every new investor has to unlearn.
Why Diversification Matters More Than Conviction
New investors often want to concentrate their capital in the one deal that feels most exciting. This instinct is understandable. It’s also usually a mistake. Angel investing is a game of outliers. Most individual bets fail, and a small number of wins carry the entire portfolio’s return.
Given that reality, spreading capital across a meaningful number of investments matters more than betting big on a single favorite. Consider a portfolio of just one investment, however promising. It exposes an investor to total loss on a single roll of the dice. By contrast, a portfolio of fifteen or twenty gives the eventual outliers room to emerge. This helps compensate for the inevitable losses along the way.
The Overlooked Cost of Being a Passive Investor
Many new angels assume that writing the check is the end of their job. In reality, that’s just the beginning. The investors who add real value stay engaged after the money lands. They make introductions, offer perspective when asked, and show up for the founder during hard stretches, not only during good news updates.
This connects directly to a lesson Adrian Vanzyl has emphasized elsewhere: presence matters more than prestige. A passive investor who never engages again after the wire transfer isn’t just missing an opportunity to help. They’re also missing the chance to actually learn from watching a company evolve. That kind of experience is exactly what builds the pattern recognition future investments will depend on.
Why Founder Access Matters More Than Deal Flow
New investors often obsess over deal flow. They assume that seeing more opportunities is the main constraint on good outcomes. In practice, though, access to genuinely strong founders matters far more than volume. Ten mediocre deals reviewed carefully will never outperform one exceptional founder taken seriously.
Building that kind of access takes time. It comes from being known as an investor worth having in the room, not simply an investor with capital to deploy. Early on, this means saying yes to a smaller number of thoughtful conversations. It means resisting the urge to review every single deal that crosses a desk.
What This Means for Anyone Considering Their First Check
For anyone weighing their first angel investment, the practical advice is straightforward, even if it isn’t glamorous. Expect to be wrong more often than right. Build a real portfolio instead of concentrating on one favorite. Stay engaged well after the check clears, since that ongoing engagement is where the real learning happens.
That’s the process Adrian Vanzyl went through the hard way. It’s also the same process he now recommends to anyone just getting started.