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Why "Investor" is a Difficult Language to Learn

Italian Flag by Dave Kellam via Flickr

When I landed in Italy last Fall from DC, where I'd lived for the last nine years, I knew hardly any Italian.

Ciao, Gratzie, Arrivederchi, and a handful of other catch phrases that I'd picked up from movies or books made up the full extent of my vocabulary.

When I'd try to say something and I didn't know the word, I'd say it in English with an 'a' or an 'o' at the end. If that didn't work and I could remember back to my high school days I'd try the French or Spanish word. Failing all those, I'd start waving my hands. Even now, I still communicate with a combination of keywords, infinitive verbs and charades.

It's humbling to have so much you want to say, but lack the skills to articulate it. Until I become fluent, all I can convey with simple words and gestures is just the tip of the iceberg.

Thankfully, Italians love you just for trying. Beginners like me are encouraged at any attempt of the language with ear-to-ear smiles and reciprocal gestures. It's fun and it's encouraging to learn Italian immersed in the culture and people.

Fundraising entrepreneurs don't have it so easy when they need to learn to speak Investor as they start pitching angels or VCs for capital.

Here are three reasons why I've found it to be such a difficult language:

It is as much about what you don't say as much as what you do

Sure, there are terms to know like preferred stock, IPO, pre-money valuation, EBITA, exit strategy. But someone who speaks Investor also knows to talk less about the product and more about the business case. They know the objections someone might raise and they address them before the questions are even asked. They avoid the things that raise more questions than they answer. They know to tailor their pitch to the audience, avoiding the industry buzzwords and acronyms others wouldn't necessarily understand. They know not to say that their financials are conservative. They know not to ask for an NDA.

You're not always surrounded by constructive teachers

In Italy, those struggling with the language are encouraged and embraced. In the venture world, not every new entrepreneur looking to learn to speak investor has access to such encouraging teachers. Most land in a Shark Tank. At Springboard we run a "how can we help" fast pitch program called Dolphin Tank designed to engage the audience in providing honest but supportive suggestions, criticism and connections for the presenting entrepreneurs. It's fascinating sometimes to listen to people provide feedback during these events. Even when told the purpose of the session is to be supportive, everyone's natural tendency is to go for the jugular.

You think you're speaking it when you're not

Like Italian, the best way to learn Investor is to immerse yourself. Recruit a Personal Advisory Board to coach and mentor you, seek out entrepreneur networks locally and nationally, and just go out there and pitch. But even if you immerse yourself in the process, you'll never quite know exactly that moment when you start speaking Investor. But keep trying, never stop learning from every presentation experience, and evolve your pitch after every investor interaction. Eventually you'll hit the pivotal moment. You can read all you want about how to pitch, but the only way to really learn is to do.


There are many entrepreneurs I've met who are building promising businesses, but are still talking the language of the customer, not the investor. When they present, the investor only sees the tip of the iceberg. The best investors I know ask the right questions, cut through the surface, and understand even from a poor pitch the real opportunity that lies beneath.

In the meantime, Springboard and many other organizations will be there to help translate for entrepreneurs and coach them to speak Investor.