Grabbed your attention?  Good.  Should mention that the title to this post should be:

“Why I, former ad sales executive, make for a very bad fundraiser… but a freaking good entrepreneur.” 

To be perfectly honest, I think that sales people are bums when it comes to fundraising.  Put plainly, we’re polar opposites.

Let me explain.

As salespeople, we’re driven to close deals.

Some of us are driven by money, others less so.

But we all like the art and science of the deal.  The more deals we secure, the better.

Fundraising requires that:

- you play hard to get,
- you overplay your hand,
- you pretend that you’re just not, you know, all that into the other party.

Ultimately, while few will admit, funding is meant to be a means to an end, but judging by the anemic rate of exits, it is the end game apparently.

Ironically, closing a sales deal should be the end, but sales people are driven to repeat and up their feat, so they view the first deal closing as a means to and end: more business and growth.

In an odd, strange twist, the salespeople tend to demonstrate the trait investors seek in fundraisers, and fundraisers tend to swoon the way you’d expect a commission-rich salesperson to behave.

Salesmanship requires that:

- you follow up,
- you hustle,
- you offer more value to close the deal.

Personally, I’ve not raised “outside money” because I am dumb enough to think that I am too smart for my own good when it comes to the draconian clauses that VCs shove down entrepreneur’s throats. I don’t accept them.  I tell them what I think is a fair deal, and while ironically (or dare I say fittingly) clients view my terms and proposal as fair, VCs don’t.  The hell with them: having had a decent-sized exit under my belt, I also didn’t absolutely need to bend over for a VC, either.

I will be the first to admit that I’ve failed as a fundraiser, but in the process, somehow, some-freaking-way, I am winning as an entrepreneur… and I don’t for one second think that is a coincidence.

Coffee is for Closers

Each time VC money’s been close enough for me to smell it, something else draws me away.

Maybe it’s the smell of money from actual sales and revenues; you know, from clients (that crazy concept).

Whatever it is, it’s pretty clear that fundinistas are good at spotting suckers who are willing to fund ideas that, let’s face it, have no business being funded, but are funded nonetheless and continue to get funded no matter how freaking futile and feable they are.  Good for them, those lucky f***s.

Of course, that is what many say of my company and yours truly, but I’m not the one handing out pink slips these days, now am I?

Sales people, on the other hand, can’t be bothered to spend six months making love to a spreadsheet.  They spot the money and go for it.  It’s a strange concept, but I promise you, a more fruitful one.

Bottom line: To be successful as an entrepreneur and a salesman, you need BALLS.  Brass balls.

To be successful as a fundraiser, you need to kiss ass.  Lots of ass.  We’re talking proctologist-levels of ass.

If you’re sick of tossing salad and want to develop some balls, I’ve embedded a clip for your viewing pleasure.

Happy April Fool’s Day, and remember, if you want to be your own boss and not have to be a dick of a boss, try for as long you can to avoid VCs.

One day, I will run down the long, long list of financiers I hit up over the years and tell you with full candor what I did wrong with each one, but for each one, I will also list the 5 or so clunkers they invested in…

In the meantime, enjoy this: