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How to be a Terrible Startup Advisor

WS
Wil Schroter
How to be a Terrible Startup Advisor

There ought to be some kind of test Advisors need to pass before they are allowed to give startup advice.

But there isn’t — literally, anyone can call themselves an Advisor and get away with it. Hell, I’m doing it right now!

Having been in the business of advising startups for decades, I can say this with conviction — most startup advisors are horrible, and they have no idea they are horrible. I’m not talking about bad actors or those trying to do something nefarious. I’m talking about the advisors who actually think they are helping, and instead are doing a lot of damage.

That’s also not to say that Advisors don’t have helpful or useful advice. The problem stems as much from their delivery as from their actual advice. Sometimes, yes, the advice itself is horrible! But more often than not, Founders fall into a trap of getting what could be good advice delivered in a dangerous way.

A State of Total Unawareness

The number one problem I see with Startup Advisors is a brutal lack of self-awareness. The issue isn’t that they are deliberately misguiding an aspiring startup; it’s that they don’t even realize they are.

Most startup advisors assume that because they have an opinion or experience, it must be fact. It’s not. But when you deliver an opinion with the same conviction as you deliver a fact, a startup Founder can’t tell the difference. Kind of like nowadays when AI tells you something entirely false with absolute certainty. It’s easy to overlook!
One of my favorite moves is when a startup advisor tells a Founder, “No investor will ever fund this!” The poor Founder runs home with their hopes and dreams shattered. In their minds, the Advisor has determined their outcome.

Now think about this. The Advisor’s ability to make that determination assumes they have the decision criteria for every investor on the planet. How many Advisors would have the ability to make a wholesale assessment of where the entire investment community stands on every investment? Probably none.

But that lack of self-awareness is the heart of the problem. Advisors don’t realize the limits of their own advice. How often does an Advisor open with “You know, I can only speak for myself, and my advice may not apply anywhere else, or it could be false, but here’s what I think…” I’ve heard that intro of self-awareness exactly zero times in my career as a startup Founder. And yet it’s probably the most useful framing any Founder could get.

The Bias of Bias

What’s also lost is the understanding of the Advisors’ own bias.

Everyone has a bias based on their own experiences. If every time you raised capital in the past it went horribly, you’re going to have a bias toward investors. If you’ve found that social media marketing has been a huge boon for customer acquisition, you’re going to recommend that all the time.

When Advisors then deliver advice with that same bias (usually without recognizing it), they are deforming the Founder’s view. The problem is that the Founder is rarely in a position to make an honest assessment as to whether the Advisor’s suggestion may be tainted.

I’ve had VC’s tell me in meetings, “That will never work!” (regarding my product) because they’ve seen it fail in previous investments. Taken at face value, that would be “good advice.” But in these cases, I knew they were verifiably wrong (I had already made it work), and I shudder to think of how I would have been horribly steered in the wrong direction based on bias.

Also, for the record, VC’s are the heavyweight champions of delivering opinions packaged as facts, and bias delivered as gospel!

Confusing “You Should” with “You Might Consider”

What ends up turbo-charging this bad advice isn’t just the conviction with which it’s delivered; it’s the implied consequence of not following it.

As Founders, we get into this weird parent/child relationship with Advisors. Advisors will often speak to us like they are telling a child not to touch the hot stove for the first time. They mean well, but when we go ahead and touch it anyway, they get personally offended. They make the mistake of treating our adherence to their advice as the value of the advice.

Frankly, I find that disrespectful to Founders. I always frame my advice with “You might consider” to imply that it’s your decision as the Founder, not mine. You should take what I have to say and weigh it against your own compass, not mine. I’m not soft-pedaling my advice; I’m putting it in perspective.

The idea that Founders should blindly follow advice just because an Advisor provided it feels narcissistic at best, and potentially dangerous at worst. The idea that the Founder should be made to feel bad for not following someone’s advice is just ludicrous.

With Great Advice Comes Great Responsibility

I take my role as a Startup Advisor very seriously. I think that’s because I give startup advice for a living, so I’m very accountable for the words that come out of my mouth in every Founder conversation.

What I’ve learned is that we can’t take our role as an Advisor lightly. Every word shapes an outcome, and while we intend those outcomes to be positive, we can very easily create negative outcomes with positive intentions.

The key here is reframing our role. As Advisors, our role is to provide a potential answer for consideration — not a directive. We need to shape the advice we deliver with an appropriate recognition of our own bias so that Founders can properly interpret what we say.

Our job isn’t to be Oracles. Our job is to provide options. What separates a great advisor from a terrible one isn’t just the advice — it’s how it’s delivered.

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