8 Simple Rules For Dating Your Advisor

Getting time and attention from experienced advisors is a rite of passage for the first-time entrepreneur.

Entrepreneurial advisors provide everything from informed feedback, market validation and technical direction, to introductions that can lead to partnerships, investors and customers.
Advisors are often former serial entrepreneurs themselves with well-earned battle scars from risking, failing and succeeding enough times to have sharp
insights into the venture building process. They have a special empathy for the struggling entrepreneur. There’s satisfaction in helping an up-and-coming entrepreneur avoid the same mistakes, and giving them insights that will help accelerate their progress.
Not all advisors have the right experience, and it is very hard for the entrepreneur to know which advisors can truly help their company.  It takes many first dates to find those perfect matches. But advisors kiss a lot of frogs too: Frogs, hunchbacks, maniacs, dreamers, neurotics – and I suspect a few psychotics. Entrepreneurs come in all sizes and for advisors it can be exhausting to try to help them all – particularly those entrepreneurs who don’t really want to be helped, or who are not ready for outside advice.
So, for the entrepreneur about to go seeking advice from advisors, here’s some blunt, very blunt, advice:


1. Be honest: Are you really just looking for a hookup, eye candy, or a sugar daddy?

One night stands are so last-century. If you only want some quick nuggets of advice, then just read my blog – or better yet, hire a consultant. If you are using me to get to someone else – such as an A-list executive or an investor – then the chances are you won’t get it; at least not right away. My contacts are more important to me than you are, and I don’t want to waste their time. And really, if I think you can benefit from an introduction, I will offer without you even asking.
Entrepreneurs are always looking for funding, but the purpose of our date is advice and help. If you only want me for my money then tell me beforehand, because it will be still be obvious you’re just looking for a sugar daddy. Being coy will only make it look like you asked to meet under false pretenses.
Perhaps instead you are looking for some eye candy for your advisory board. You want to display experienced names on your website to increase your venture’s credibility and attractiveness. Not so fast. Any advisor who pimps-out their name so quickly is probably more of a consultant wanting to prospect for more business. We all know who they are, and walking arm-in-arm with them might damage your own reputation.
Corollary: We’re not going all-the-way after the first date.
I’m not that easy. By the end of the first meeting, I almost definitely will not sit on your board, be an official advisor, an investor or your partner. Assuming or implying this will probably be a major turnoff. It may indeed be in the cards, but we just met.  Unless you are the entrepreneurial equivalent of Brad Pitt, I won’t go all-the-way during our first date. I need some time to get to know you.

2. Don’t ask me how to lose 20 pounds the night before the prom.
obesity scale

I cannot undo your last 12 months of mistakes in one sitting, and neither can you. If you need miracles call a faith healer. Success is a habit, and it takes time to see the results of those habits. If you are desperately broke and running out of time then I probably can’t help you. I’m happy to try, but the fact is that you’re not attractive to investors or customers anymore. You need an extreme makeover, and makeovers don’t happen overnight. Your problems are more fundamental than merely lacking a white-knight angel investor.

3. Don’t play hard to get.

For that matter, don’t be cocky, condescending or evasive. Entrepreneurship is a constant struggle and no first time entrepreneur has it all figured out. Being a know-it-all is a major turnoff when you are asking someone for advice. If you’re so smart then why are we talking? You came to me, remember?
Corollary: Don’t wear heavy makeup. I can still see what you’re covering up.
Too many entrepreneurs try to embellish their company’s traction and status to seem bigger and more credible when they only serve to do the opposite. Your venture is not going perfectly so there’s no sense in trying to hide all the flaws and rough edges. I’ve been there before. I’ve seen it all, and I want to help. Trying to gloss over flaws or downplay obvious weaknesses only makes you seem more inexperienced and unattractive.
Oh, and don’t be late. It’s not about control or respect – by this point in my career I’ve have lots of both. I learn a lot about you by how you value other people’s time. If you are late or otherwise inconsiderate, why would I introduce you to my colleagues? And it’s not just about me; wasting my time means you are taking time away from another entrepreneur who needs help.

4. If you have to tell me how great you are – you’re not.

If your reputation doesn’t precede you or impress in one sentence, then don’t try. Your stint as a consultant, or even at that fortune-500 company means very little. That VP title you had at your former, well known company has a shelf life of about 10 minutes after you’ve left. You’re an entrepreneur now. Your new venture is all that counts. The more you mention your past credentials, the more insecure and inexperienced you look.
Please don’t misunderstand; being a ‘domain expert’ in a particular market is extremely important. It means you truly understand the market pain and opportunity, and have access to customers. Most new entrepreneurs are young and have no such deep domain experience. Other first time entrepreneurs (corporate refugees) overstress their titles or the brand of their former company: Neither of which means much in the entrepreneurship world. You may have been a star athlete in your former sport, but even Michael Jordan couldn’t make it to the big leagues when he stepped onto a baseball diamond.  Recognize that you’re playing a different game now, and that you need to go to spring training along with all the rookies.

5. If all you want is someone to rave about your idea, then call your mother.

Repeat after me: Ideas are a dime a dozen. Ideas are barely worth the paper they are printed on. Someone has thought if it before. Someone has even tried it before. Someone is probably already doing it. Pick one. Pick them all. Now, let’s talk about execution.
Corollary 1: Have a thick skin. Your idea is not as great as you think.
Just because you’ve never heard of a product like yours before, doesn’t mean it’s unique or valuable. Your idea probably has more holes than OJ Simpson’s alibi. Be prepared to discuss. That’s part of the entrepreneurial process – to find the right mix of market opportunity, customer ‘pain’ and unique approach. Often, there is nothing about the product that is unique, or needs to be unique.  Success is almost always about timing and execution.
Corollary 2: If you merely want someone to agree with you, then adopt a parrot.
As a startup entrepreneur you are deep in the trenches right now, whereas I can see the forest for the trees. It is much easier for me to look above from 10,000 feet and see clearly what is wrong (and what is right) about your venture. There are answers you don’t want to hear, new things you’ll have to do, or re-do.
Most likely you may have to change direction or strategy, or rethink some assumptions. You can fight me on every suggestion and try to convince me that everything you are doing is on the right track. Trust me, I know how much it sucks to scrap a major part of your product strategy or target market and have to start over.  It’s better to bite the bullet and do it now than to spend your life savings (and life) building the perfect product that no one wants.

6. Please be smarter than me – at least about your own business.

Chances are that I’ll have an iPad or smartphone in front of me. If I can search while you’re talking and know more about your industry and competition than you do – you’ll look arrogant and uninformed. You’d be surprised how often an entrepreneur sits down with an advisor (or worse – with an investor or customer) without sufficient knowledge of the problem, the market and the competition.
So Google. Google your industry, Google your technology, Google the problem; Google the solutions that have been tried before and are currently being tried by your competition. You should be an expert. You should be *the* expert.
While you’re at it – Google me. It helps to know a little about my own background – it not only tells me you value my experience, it shows me  that you’ve done your homework. If there is one common trait among entrepreneurs it is that they are not lazy, and it costs nothing to be informed.

7. Please tell me if you’re dating other people.

Few things are more annoying than spending time giving an entrepreneur advice when they are already secretly getting conflicting advice from others. If you are already set on taking advice from someone else, then don’t ask me! It is a waste of my time to help you craft a venture capital fundraising strategy when tomorrow you’ll decide to take your uncle’s advice and apply for a loan or a grant.
Shopping around for advice is an oxymoron since it presumes you know which advice is best: You probably don’t. What you’re really doing is talking to advisor after advisor, until you find the one that gives you the advice you want to hear, or advice that is easiest to implement – but not necessarily best for your business. Of course you will indeed have multiple advisors; it’s just that they should be complementary – each providing insights and expertise in different domains or different functional areas.

8. Promise you’ll call me in the morning.

I don’t run one of those old-fashioned advice booths where I dispense advice for a nickle to each person waiting in line. If I do spend time and energy helping you, then at least let me know how you are doing. Follow up. The more time, energy and knowledge I give you – give it back.
So don’t love me and leave me. It is rude to just take in all the advice and benefits of my experience, and my introductions without so much as an email follow-up; you’ll unnecessarily burn a bridge. You never know when I’ll have the chance to ‘talk up’ your company, but if you disappear after our first meeting, how can I help you? The more I help, the more I probably want to be involved; at the very least I’d like some feedback and acknowledgement that my advice is helping you. Aside from being gratifying, feedback helps me be a better advisor.
If this is the second time we’re meeting, you need to tell me how you’ve taken my advice or have learned something from our last conversation. If you disregarded my advice the first time, why would I waste my time again?
Remember, I used to be an entrepreneur, and I probably still am an entrepreneur. I’m on your side. I’ve been there. I know you better than you know yourself. I want to help you be successful. There is nothing more gratifying than helping the next Mark Zuckerberg, or being behind the scenes at the next Google. So, dear entrepreneur, please take this advice to heart – so we can have more dates, and more relationships.

Image Credits
creative commons icon banner

Attribution-NonCommercial-ShareAlike 2.0 Generic (CC BY-NC-SA 2.0)

Follow Me:

Share Now

Share on facebook
Share on twitter
Share on linkedin