Episode Transcript:

ADAM MCGOWAN [00:08 ]: Welcome to episode two of Ventures in Tech, brought to you by Firefield. This is Adam McGowan and on today’s show we’re going to be talking about the topic of advising and mentoring in the startup ecosystem. I’ll again be joined by my colleague Henry Reohr from Firefield who’ll be leading today’s conversation. And with that, I’ll let Henry take it away.

HENRY REOHR: [00:32 ]: Well, before we dive into a lot of detail, I want to start at a pretty high level. It would seem that when an expert is willing to share insights with an entrepreneur, that’s a pretty good thing. As with most good things, more is usually better. Do you think it would be fair to say that an entrepreneur should take all the mentorship advising they can get?

ADAM [00:56 ]: I wish it was universally fair, but I don’t really think that it is. I think one of the challenges is the fact that too much advice can actually be, at best, a bit confusing, and at worst, I think it could actually be misleading or even potentially paralyzing for an entrepreneur.

I do think there are a number of factors that play into the utility of a particular piece of advice. Namely, I think there are three. The first one I would describe as the circumstance of the start up, The second would be the background of the expert, and the third would be, what I would call, the context of the interaction between the entrepreneur and the actual expert.

HENRY [01:43 ]: Well, let’s take any of these one at a time. Can you talk about how the circumstances of startup plays into advising and mentorship?

ADAM [01:54 ]: Sure. Let me start it by breaking up what I call advice into two distinct categories. The first category I would call “personal based advice”. What I mean by this is the kind of advice you would expect that’s either somewhat inspirational or the kind of things that help define the character or the skill set of an individual – of the entrepreneur.

Having an entrepreneurial mindset; being able to sort of work through a collection of challenges all these sorts of things. The skills an individual needs to be able to be successful at bringing a new venture to life or growing one is really what I’m talking about, and there’s a lot of opportunity for mentorship here. This is a wide range… it ranges from, you know, kind of personal wherewithal, all the way through public speaking and being better at pitching.

But that’s really not what I’m referring to. I’m talking about the second category and the second category is what I would consider “venture based advising”. This is advice that directly impacts the company and not necessarily the individual. And this advice is contingent on what’s actually going on within the business itself. This has a lot to do with the industry; has to do with the stage of the company’s life cycle; has to do with their financial circumstances. It has to do with the nature of their customers and the list goes on from there.

So these venture based factors matter because the value of any advice, in my view, is going to be directly related to how it’s going to address a company’s very, very specific situation. So that’s why it’s important to be able to assess that upfront, particularly when you’re talking about this venture based advice.

HENRY [03:44 ]: So how about the person’s background? Are you suggesting that entrepreneurs try to make judgment calls on whether the expert offering them advice can actually provide them any value?

ADAM [03:58 ]: Yeah. It might sound a little bit strange, particularly if you consider a lot of entrepreneurs (particularly first time entrepreneurs) might not have a ton of experience; might be somewhat young or semi new to their space or to the field of entrepreneurship; and it might seem a bit of a mismatch. Whereas an expert may have decades of experience.

So the idea that an early entrant into the space who’s super ambitious is second guessing someone far their senior in terms of experience might seem a little bit odd, but I think that not doing it and not challenging those assumptions is probably one of the biggest mistakes that I see for entrepreneurs who are on the hunt for advice.

And I think the challenge there is that they don’t trust their own instincts. The reason I think that matters is because the term “expert” is unbelievably subjective. And one of the big problems is that it’s very easy to claim expertise but it’s also nearly impossible to discredit that someone is in fact an expert.

There are many different ways to assess someone’s credibility in their field but I think the point I’m trying to make is: because someone labels himself an expert, because they’ve had a lot of years in a particular field, it doesn’t necessarily mean the advice they’re going to provide is going to be ideal for you. I think that’s really what I was getting at it.

HENRY [05:26 ]: It seems like it might be a tough conversation for somebody to have with someone who’s supposed to be an expert in their field. Do you have any tips for how to go about asking an expert to justify themselves in that way?

ADAM [05:45 ]: That would be a very hard conversation. It would be extremely awkward, it would actually be something that might be so off-putting that it could really have an impact on the ability to even get any advice. So while I’m advocating for justifying the expertise of the “expert”, I’m actually not advocating to do it face-to-face.

What I’m really talking about here is a lot of work that’s happening behind the scenes. We’re talking about homework that’s being done before you go about having one of these sessions with an expert – before this mentoring or advising ever even takes place. An entrepreneur should use tools at their disposal, starting with things like LinkedIn, and Googling and taking off from there – to really understand as much as they can about the advice giver before they actually start collecting advice from them.

Search not only or what they’ve done as far as companies, but what those companies’ histories have been; what they’ve done outside of those companies; if they’ve done other advising or mentoring; how much depth they’ve had in that field, how much diversity they have in their background. These are all really important things to know.

And I think what an entrepreneur should try to do is to really use that knowledge and foundation that they’ve discovered about this person for the friendly, get to know you, initial phase when they are actually getting introduced and having to meet and having that first session. There’s a lot of this colloquial and congenial Q-and-A that happens at the beginning.

My argument is to make the most of it and have it actually be more than idle chit-chat. Start with your homework and hopefully try to fill in those blanks when you actually talk to one of these individuals, and I think that when you’re coming from a place of interest – when you’ve shown you’ve actually dug into their background – this won’t come off as off-putting at all.

This will actually be, probably, very complimentary to the individual. A lot of experts like to talk about their experience and why they have expertise. I just think that if you come at it from the right place, with enough foundation and information, it will actually work out really well and probably to your benefit.

HENRY [08:01 ]: So beyond doing your homework and trying to qualify the experts that you’re talking to, are there any red flags or tips for sniffing out particularly bad advice that you might get from someone?

ADAM [08:18 ]: I think there are. There’s a lot of different types of bad advice but I tend to lump them into three pretty broad categories. The first one I would describe as the “anecdotal” advice. What I mean by this is the idea that you hear a story from an expert – it’s one instance of something happening and then having that instance suggest that there is some sort of a trend..

One piece of data does not make a trend – particularly in the case of someone who has a lot of experience – and you would know this from doing your homework. The hope would be that they piece together a pattern of behavior and then use a pattern that they’ve experienced over an extensive career to be able to give you insights into how that pattern can apply to your situation. So I would be wary of the one off, the “anecdotal”.

The second one is, and this isn’t really a great term, but I would consider this the “narcissistic” advice. This is the idea that the expert believes that their opinion about something can be projected to the rest of the world. If you show someone your app and say, “What do you t