Always Be Closing 

Every entrepreneur should watch the movie “Boiler Room” with Ben Affleck and the classic “Glengarry Glen Ross” with Al Pacino and Jack Lemmon.  While I don’t propose using the hyper-aggressive sales tactics shown in the movies, I do believe that entrepreneurs need to focus on closing, at all times. How do you secure the next investor, the next customer, the next partnership, the next referral?

You have to close them.

You have to ask for money.

Not long after I started my orthodontic technology company, Lingualcare, an orthodontist told me something that stuck in my mind. We were discussing how he convinces patients who come in for a consult to sign up for braces on the same day. Like car dealers, orthodontists know that if the patient doesn’t sign on the dotted line before they walk out the door, the odds of turning them into a customer drop dramatically.

Most business-minded orthodontists have a treatment coordinator, usually a woman, who talks with patients post-consult. She will take them into a comfortably, well-lit room and explain the different options and pricing. It is her job to close. When I asked this particular orthodontist what made a good treatment coordinator he said, “She can’t have personal financial problems. People with money problems are afraid to ask other people for large amounts of money.”

Every small company I’ve ever been associated with has cash flow issues. It comes with the territory of starting something new. 

As entrepreneurs, do we wear our financial struggles our sleeves? 

Feeling financially insecure makes it hard to ask for money. It leaves you tentative, unsure. You feel compelled to apologize for requesting such a large sum, to start dropping the price and negotiating against yourself if they hesitate.

I know. I’ve been there.

The challenge is to avoid reinforcing our own financial insecurities. If you don’t feel confident enough to ask for the big order, continued financial fragility becomes a self-fulfilling prophecy. 

Recognizing the problem is a first big step to overcoming it.

Before you go into a situation where you are going to ask someone for a large sum of money, get out your notebook and write down exactly how you are feeling about money in that moment. Write whatever comes to mind.

  • The air conditioner made a weird noise yesterday. What if there is something wrong with it? How much is that going to cost to fix? I felt my stomach get tight when I heard it. 
  • My son wants to play lacrosse this year. I want to support him but all I can think about is how much the equipment is going to cost and how much time it will take to get him to and from practice and to his games. I hate disappointing him, it makes me feel like a bad parent.
  • My best friend is getting married and he invited me to bachelor party in Cabo. Everyone is going but I’d have to max out a credit card to afford it. I’m embarrassed to admit I can’t do it. I’ve spent all morning coming up with excuses to not admit it’s about money.

Keep writing until you have purged every bit of money-related anxiety from your brain. Include everything that crosses your mind. Even the smallest worries can make a difference in your emotional state.

Now you need to think about why you’re asking for the money? How are you going to use it? What value will the person giving it to you derive from the transaction? Write down exactly what you are going to ask for and why the person should give you the cash and why you are worthy to receive it.

  • I want this customer to buy $15,000.00 worth of software from me. I know that the implementation will take less than a month and after that it will take six months for them to break even on the investment. Example: It will save them from having to hire another customer service person. Example: it will speed up development of their next product by a year. There is nothing wrong with asking this customer to buy from me.
  • I want this investor to invest $500,000.00 in my seed round. Yes, it’s risky, but I am giving him/her a great deal, a convertible note with a 25% discount. If I didn’t believe in the potential of my business I would not be here putting in the time and effort to make it successful. This person’s job is to invest money. They do early stage investing despite the risks. They want the big rewards, high risk is the trade-off for that.. I’m offering a chance for them to make 20x on their money. There is nothing wrong with presenting this opportunity to them. 
  • I want this company to sponsor my event. It is aimed right at their target market and I believe they will get value from the opportunity to communicate with our shared audience. They have money allocated in their budget for events like mine. In the noisy world of social media I’m offering them a chance to talk directly to a valuable set of customers in an intimate setting. There is nothing wrong for asking them to be a sponsor.

The idea here is to remove the emotional aspect of asking for money, to empower yourself with the belief that you are not a beggar requesting a handout. You are a business person presenting a business opportunity. They need to decide if your proposal works for them based on their own criteria and if it fits their budget.

Don’t apologize.

Don’t offer up unsolicited discounts.

Ask for the order.



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