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Month: September 2026

When to Double Down and When to Walk Away, According to Adrian Vanzyl

Posted on by Adrian Vanzyl

Every investor eventually faces the same uncomfortable moment. A portfolio company is struggling, and a follow-on round is on the table. Adrian Vanzyl has sat across that decision many times. He’s done this both as an investor deciding whether to write another check, and as a board member watching a founder fight to keep momentum alive. There’s no formula that makes this decision easy. However, there are patterns worth understanding before the moment arrives.

This isn’t really about picking winners in advance. Instead, it’s about recognizing which signals actually matter once a company is already underway.

Why Sunk Cost Is the Biggest Trap in This Decision

The single most common mistake in follow-on investing is anchoring to money already spent. This happens rather than focusing on the company’s actual prospects going forward. Specifically, an investor who’s already committed significant capital can feel pressure to protect that investment. As a result, they write another check regardless of whether the underlying business has genuinely improved.

This instinct is completely understandable. After all, nobody wants to admit an earlier bet isn’t working. Yet the money already invested is gone either way. The only question that should matter for a new check is simple: does the company, as it exists today, represent a good investment on its own merits? Everything invested before that point is irrelevant to that specific question, even though it rarely feels that way in the moment.

The Difference Between a Struggling Company and a Broken One

Not every company that’s missing targets is in genuine trouble. Some are simply early, or navigating a market that’s taking longer to mature than expected. Others have a fundamentally broken model that no amount of additional capital will fix. In practice, telling these two situations apart is the actual skill here. It’s also far harder than it sounds from the outside.

A struggling-but-viable company usually shows specific signs. The founder understands exactly what isn’t working and has a credible plan to address it. Metrics are moving in the right direction, even if slowly. Notably, the market opportunity hasn’t fundamentally shrunk. A broken company, by contrast, tends to look very different. The founder keeps changing the explanation for underperformance. Metrics stay flat or decline despite repeated pivots. The market itself has moved on entirely.

Why Founder Behavior Under Pressure Reveals More Than Metrics

Metrics matter, but they lag reality. Founder behavior under pressure often reveals what’s actually happening faster than any dashboard can. Consider a founder who gets more transparent as things get harder. That founder shares bad news early and asks for help before it’s requested. This is exactly the trait that predicts recovery.

By contrast, a founder who becomes defensive shows a very different pattern. The same is true of one who starts hiding bad numbers, or blames external factors exclusively. This behavior doesn’t guarantee failure on its own. Even so, it removes a critical ingredient that struggling companies need most. Specifically, it removes an accurate, shared understanding of the actual situation between founder and investor.

The Case for Walking Away Even When It’s Painful

Declining to participate in a follow-on round feels like giving up. This is especially true on a company an investor has believed in for years. In the end, that emotional weight is real, and it shouldn’t be dismissed. Still, continuing to invest capital into a company with a genuinely broken model doesn’t actually help anyone in the long run.

It delays a founder’s ability to face reality and make necessary changes. On top of that, it ties up capital that could go toward companies with a real path forward. In fact, walking away from a struggling investment isn’t a failure of loyalty. Rather, it’s an acknowledgment that continued capital only helps when the underlying business can actually use it productively.

What Adrian Vanzyl Says Doubling Down the Right Way Looks Like

When doubling down does make sense, it should come with more than just money. The investors who add real value during a difficult stretch increase their engagement alongside their capital. They make more introductions, ask harder questions, and show up more frequently, not less.

This pairing matters more than it might first appear. A check without increased engagement signals confidence in the wrong thing. It’s often mistaken for confidence in the founder, when it may really just be confidence in the sunk cost already spent. Real conviction shows up as time and attention, not simply as capital.

What This Means for Investors Facing This Decision

For any investor sitting across from a difficult follow-on decision, the practical discipline is straightforward, even if it’s not comfortable. Evaluate the company as it exists today, not as it existed when the first check was written. Watch founder behavior under pressure as closely as the metrics. And if the decision is to double down, commit real engagement alongside the capital, not capital alone.

That’s the discipline Adrian Vanzyl applies to every difficult follow-on decision, whether the outcome is another check or a hard conversation about walking away. It’s a discipline any investor facing the same crossroads can apply just as well.

Why the Best Exit Isn’t Always the Biggest One, According to Adrian Vanzyl

Posted on by Adrian Vanzyl

Most conversations about startup exits focus on one number: the headline valuation. Adrian Vanzyl thinks that focus is misplaced. After decades spent investing in and advising technology companies, he’s watched founders chase the biggest possible number and later regret it. He’s also watched founders take a smaller deal and end up far better off. The difference rarely comes down to price alone.

This isn’t an argument against maximizing value. Instead, it’s an argument for defining value correctly in the first place.

Why Headline Numbers Hide the Real Terms

A big acquisition number attracts headlines. However, it rarely tells the full story. Earn-outs, escrow provisions, retention requirements, and equity-versus-cash splits can all quietly change what a deal is actually worth. In practice, a ten million dollar deal paid entirely in cash at close can be worth more than a fifteen million dollar deal loaded with contingencies that may never fully pay out.

This matters because founders under pressure to close a deal often focus on the top-line figure first. The structure gets negotiated second, and often with less scrutiny. As a result, this happens right when careful attention would matter most.

The Overlooked Cost of the Wrong Acquirer

Price is only one variable in an exit. Fit matters just as much, even though it’s harder to quantify. An acquirer who genuinely values the team, the product, and the culture tends to integrate well. That kind of acquirer preserves what made the company work in the first place. By contrast, an acquirer chasing the deal for defensive reasons, or simply to remove a competitor, behaves very differently. Often, the acquired team and product quietly wither within a year or two.

Founders sometimes discover this too late. The acquirer’s real intentions become clear through action, not through promises made during negotiation. A slightly lower offer from a genuinely committed acquirer often produces a far better outcome. That’s compared to a higher offer from one that isn’t.

Why Timing Can Matter More Than Price

Selling too early leaves value on the table. On the other hand, selling too late risks missing a window that may not reopen. Both mistakes are common. Neither is easy to diagnose in the moment, since the right timing only becomes obvious in hindsight.

A useful discipline is separating the emotional pull of a big number from an honest read of the company’s trajectory. Consider a high offer that arrives while momentum is genuinely accelerating. That offer deserves serious scrutiny before acceptance. By contrast, the same offer arriving after growth has already started to plateau deserves very different consideration. After all, it may represent the best price the company will ever see again.

The Founders and Employees Who Get Forgotten in the Structure

Exit negotiations tend to concentrate attention on the founders and the largest shareholders. Early employees often took on real risk for below-market compensation. Yet they can get treated as an afterthought in the final structure. This isn’t usually malicious. Rather, it’s simply where the negotiating leverage sits by the time a deal reaches the table.

However, how a company treats its early team during an exit says something durable about its founders. Word travels through a startup ecosystem quickly. A founder known for taking care of early employees builds a reputation that pays off in the next company they start. Meanwhile, a founder known for the opposite carries that reputation forward too.

What Adrian Vanzyl Says a Good Exit Actually Optimizes For

A good exit balances several things at once. These include fair value, an acquirer genuinely equipped to carry the work forward, defensible terms for the people who built the company, and timing that reflects the business’s real trajectory rather than short-term market noise. Optimizing for headline price alone, at the expense of the other three, tends to produce a specific pattern. The outcome looks good in a press release and feels disappointing in practice a year later.

This is a difficult balance to strike under pressure, especially when a founder has spent years building toward this single moment and understandably wants it to feel unambiguously like a win.

What This Means for Founders Approaching an Exit

For founders weighing a potential exit, the practical lesson is to slow down exactly when the instinct is to move fast. Scrutinize the deal structure as carefully as the headline number. Evaluate the acquirer’s real intentions, not just their stated ones. Consider the people who helped build the company, not only the largest shareholders at the table.

That’s the standard Adrian Vanzyl encourages founders to hold themselves to. It applies even when a tempting number is sitting right in front of them.

What Adrian Vanzyl Learned Building Teams Across Three Continents

Posted on by Adrian Vanzyl

Most leadership advice assumes a single cultural context. Adrian Vanzyl never had that luxury. Over a career spanning the US, Asia, and Australia, he’s built and managed teams across dramatically different work cultures. As a result, he’s developed a clear view on a question most leaders never ask directly. Does good management actually look the same everywhere?

His answer is no. However, it’s a more useful no than it first sounds.

Why Management Style Doesn’t Travel Automatically

A management approach that works well in one country can quietly fail in another. This happens even when the underlying company values stay identical. Direct, blunt feedback might read as honest and efficient in one culture. In another, the same feedback might feel disrespectful or even alarming, regardless of intent.

This isn’t really about right and wrong. Instead, it’s about legibility. A manager’s signal only works if the team can actually read it correctly. Consequently, the same words, delivered the same way, can produce completely different outcomes. It depends on where a team sits and what it’s used to.

How Adrian Vanzyl Approaches the Mistake of Exporting a Single Playbook

A common mistake among leaders scaling across borders is exporting one culture’s playbook wholesale into a new market. This usually happens with good intentions. A leadership style worked well at headquarters, so naturally it should work everywhere else too.

In practice, though, that assumption breaks down quickly. This pattern shows up again and again for leaders scaling across companies and regions. A rigid, one-size-fits-all management style tends to produce quiet disengagement rather than open conflict. Employees rarely say the approach isn’t working. Instead, they simply stop bringing their full effort. As a result, the damage shows up months later in retention numbers, rather than in any single dramatic incident.

Why Listening Has to Come Before Adapting

The instinct to fix this problem often leads leaders toward research. They read about a country’s business culture, study its norms, and prepare accordingly. That’s a reasonable start, but it’s incomplete on its own. Cultural generalizations, however well researched, can’t substitute for listening to the specific people on a specific team.

Direct conversation, rather than secondhand cultural summaries, tends to be the more reliable guide. A generalization about how one culture handles conflict says very little about how a particular team actually prefers to handle it. After all, every team carries its own history and its own personalities. Real adaptation requires asking, not assuming. It also means staying open to being wrong about an initial read.

The Real Skill Is Translation, Not Imitation

There’s a tempting but flawed alternative to the export-a-playbook mistake. Some leaders try to fully imitate local norms instead, dropping their own instincts entirely to blend in. This tends to backfire just as often. Teams can usually tell when a leader is performing a culture rather than genuinely engaging with it. Consequently, the attempt often reads as less authentic than simply being direct about the adjustment being made.

The more durable skill is translation rather than imitation. Specifically, that means keeping your core values and standards consistent, while genuinely changing how those values get communicated and enforced. The substance stays constant, even as the delivery adapts.

What Consistency Across Cultures Actually Requires

Consistency doesn’t mean identical behavior everywhere. Rather, it means identical underlying standards, expressed through locally legible language and behavior. Consider a leader who holds every team to the same bar for quality and accountability, while adjusting how that bar gets communicated. That leader is being genuinely consistent. By contrast, a leader who insists on identical communication style everywhere, regardless of how it lands, is confusing consistency with rigidity.

This distinction matters enormously when scaling a company across borders. Teams notice quickly whether standards are actually being held evenly, even when communication styles differ. What erodes trust isn’t different delivery. Rather, it’s different substance disguised as fairness.

Why This Matters Beyond International Companies

Even founders building a single-market company benefit from this lesson. After all, most growing teams eventually include people from different backgrounds, even within one country. The core skill, adjusting delivery while holding the underlying standard fixed, applies just as much to a diverse local team. It matters just as much for an operation spread across three continents.

What This Means for Leaders Scaling Right Now

For any leader building a team beyond their own cultural default, the practical takeaway is straightforward. Research helps, but it’s only a starting point. Real understanding comes from direct conversation with the actual people on the actual team. Hold your standards steady, and let the delivery flex to fit.

That’s the balance Adrian Vanzyl has spent decades calibrating, one team and one market at a time. It’s also a balance any leader can apply, regardless of how many borders their team happens to cross.

What Adrian Vanzyl Wishes He Knew Before His First Angel Check

Posted on by Adrian Vanzyl

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.