An Entrepreneur’s Field Guide To Mentors and Advisors

This morning I had coffee with a young entrepreneur who is building a really cool business here in Dallas.

This entrepreneur and I talked about marketshare, technology, growth plans and he really seems to have a solid plan. The startup is a super lean one person show with some outsourcing, it is getting strong traction in a very big space and the potential acquirers are obvious and slow. In general I was super impressed and didn’t see anything that stood out as a problem. That is until…

Until he started talking about mentors and advisors…

When he told me about some of the people that he has been consulting with, getting advice from, and listening to. My jaw dropped.

As I mentioned in my last blog post, there is no shortage of people who want to be heard, there is no shortage of people who are willing to dish out advice if you’re willing to listen. This doesn’t just go for writing though, it goes for in person meetings, too.

I will say it – there are snakes in the grass, people. This isn’t specific to the Dallas startup scene, it seems to be the case everywhere. So, for those of you who send me dirty notes every time I blog in a tone that isn’t playing the part of “startup cheerleader,” this probably isn’t about you and it’s definitely not about any particular community.

People like to feel smart and important. It’s human nature. Unfortunately, for the small business and startup scene, there is this pervasive underlying message being spread that if you just listen enough and attend enough meet-ups, you’ll have strong knowledge of how to succeed as though running a business is somehow like joining Alcoholics Anonymous.

I will help you avoid the snakes. Pay close attention and you might survive the jungles of starting a company.

Part 1: Identification of Varietals, Discussion & Dangers

For the purpose of this article, I will help you identify the two kinds of snakes. There are the garden variety non-poisonous snakes and then there are the multi-colored venomous ones. Even snakes without venom can leave a mark.

Snake #1: The non-venomous, good-hearted, garden variety humanitarian:



There are a lot of wonderful, genuinely good, kind people who mean well and they have read enough “Top 10 Habits” lists and have been to enough pitch days that have been programmed like a Manchurian Candidate to react with certain messages.

When they hear the question “Should I pivot?” they immediately flash back to the thirty times they have heard somebody talking about pivoting as being a part of their success and say “Yes! Why, yes. Pivot, son. Pivoting is good. Pivoting is part of starting a company!”

When they hear the question “Should I raise money?” they begin repeating in a zombie like tone “Yes, raise money. Raising money will validate that your company is headed in the right direction and you need to raise money to expand and build a team.”


The garden variety non-venomous snake is easy to identify by the following two characteristics:

  1. Easy to identify. This snake is out and about and friendly. They make good house pets. You have probably seen their photograph many times and recognize them by sight.
  2. When asked specifically about their prior success in running businesses, there is no clear answer. They may be evasive, drop names of other non-venomous snakes and probably talk about some of the events they have been involved in, but at no point will they give you a dollar figure or point to specific experience that is relevant to your startup.


The garden variety non-venomous snake seems harmless and friendly but can carry the dangerous disease of TimeWastingBadInformationitis. TimeWastingBadInformationitis is treatable with time, experience and good research. Unfortunately, the delays they can cause your business may be incurable.

If you believe you have been bitten by a garden variety non-venomous snake, seek expert advice immediately.

Snake #2: The venomous, financially motivated snake:



If you think there are a lot of non-venomous snakes, just wait until you start paying attention to the financially motivated ones. The primary difference is that the venomous snakes are not as easily identifiable because of the variety. These snakes usually don’t attack until you either have funding or publicized traction.

There are many varieties of venomous, financially motivated snakes. Varieties range from the grey and black Corporate-cog-equity-taking-board-title-snake to the orange and yellow CPA-or-attorney-fee-seeking-snake. These snakes can be financially dangerous for your business.


The venomous, financially motivated snake can be identified by the following:

  1. They “specialize” in helping entrepreneurs.
  2. Their help requires compensation.
  3. Corporate-cog varietals generally have lengthy titles at the respective corporation.
  4. When asked specifically about their prior success in running businesses, there is no clear answer. If they mention success and are pressed for answers they are likely referring to a client who paid them in cash or equity or a company they worked for.


The venomous, financially motivated snake may cause pain or death of a startup. Advice is usually self-serving and their bills can quickly become enormous. The individuals they introduce you to are often paying referral fees (or reciprocating referrals). For the corporate cog snake, their equity can quickly become a stranglehold on founder control because they are found in dens and tend to attack in groups.

If you believe you have been bitten by a venomous, financially motivated snake, it may be too late to seek treatment. All you can do is continue on with your business and hope that their poison only slows you down.

Part 2: Survival and Proper Selection

The above identification guide was meant to be taken with a grain of salt. It is humorous, but not terribly off base.

Personally, I believe that you probably know and are capable of far more than you give yourself credit for. Ask yourself why you want advice. Look deep down inside and ask yourself if you are genuinely looking for advice or whether you are looking for validation. If you decide that you are genuinely looking for advice, identify exactly what you have questions about. Specific questions, specific concerns, specific goals make you look smarter and make the advisor feel more important.

Going in for a coffee or meeting with a potential advisor/mentor and expecting them to simply tell you how to run your business is foolish, because nobody knows your business as well as you do. Not only that but it’s uncomfortable. I am very good at certain things and very bad at others; the fact that you might assume I know everything puts a lot of pressure on me as a mentor. It also shows that you didn’t research me well.

As a great example, if you are looking for answers about how to manage people and be a great boss, I am the wrong person to ask. I’m a total asshole and don’t get along with many people. If, however, you are asking me about product, trends and systems, I can help you out tremendously.

So how should a young (or young at heart) entrepreneur find advisors and mentors and avoid the snakes?

First, seek out specific experts in your field. Are you creating an app for sorting widgets? If so, then you probably want to find people who are experts in app marketing and the widget industry. If these people are one in the same, then you may be discovering that somebody beat you to market.

LinkedIn can be a fantastic tool for finding experts/advisors/mentors. Seek out people with the expertise you need and then see who you have second degree connections with. If you have any, leverage those connections and ask for an introduction.

At one of my last company’s it turned out that I had a connection to the President of Nokia USA. Wow – in the telco business you really could not ask for a better connection. I politely asked our mutual friend for an introduction, explained honestly what I was looking for (introductions to VC’s who were interested in telco) and got an intro. A few polite e-mails and coffees later I had an advisor/mentor. That person helped me tremendously and introduced me to some wonderful connections. We remain friends to this day.

Second, when you do find a mentor that you actively sought out because of their qualifications, don’t immediately offer up stock in your company. The advisor/mentor relationship is no different than dating. Get to know each other, go to dinner, meet the families. If you consummate the relationship you are going to be attached to each other for a long time through good and bad times.

A good mentor should not immediately begin seeking compensation of equity. A good mentor has clearly identifiable success under their belt and has likely been helped by somebody else. They understand the struggles of running a business and should become a person who you can confide in about the challenges you encounter.

Remember, we stand on the shoulders of those who came before us. Good mentors know this and see the opportunity to advise and mentor as both a duty and a pleasure.


This article was originally published here.

Arlo Gilbert

#Inventor #Investor #Founder #Hustler #Husband #Dad - Voted most likely to find a loophole - Advising startups & running