A recent post by Lolly Daskal (President and CEO, Lead From Within) was titled 65 Quotes That Will Dare You to Do Great Things

I followed the link and took a look at the list and it WAS inspiring … but then reality came crashing in.  How on earth was I ever going to remember them all? 65 of anything is way too many!

I needed to get to the essence of the list, so I leveraged data analytics and machine learning by pouring the entire list into worldle.net.  The result is the attached word cloud.

The answer is … Leadership requires Risk!

The subtitle of Lolly’s article says it well.  “If we are to do great things, we must always be motivated to take bold risks.”

That I can remember.

A recent post on the New Ventures BC website asked the question, “Is it Courage or Something Else that is Critical for Startup Company Leaders?

The author said courage, and later added, “a fierce desire to learn and to change”.

Someone responded with naiveté.  Someone else said patience.  Another response was Integrity, Intensity, Immediacy.

Still another said  “I think it is wrong to single out one character trait as most important for an entrepreneur. I will support an entrepreneur if he is “the package” … Other traits also important … drive, determination, focus, work ethic, ability to sell, natural desire to sell, resourceful, ability to get help, inspirational, confidence, integrity, likeable, successful in life, energetic, energizing.”

Jimmy Pattison says that the most important characteristics an individual needs for success are: honest, hardworking, intelligent, able to communicate, able to work in a team.

My own personal list includes leadership and entrepreneurship and paranoia and audacity.

  • Leadership (standing up and choosing a direction).
  • Entrepreneurship (acting like an owner).
  • Audacity (the willingness to take (big) risks).
  • Paranoia (the coldly calculated essential foil for audacity … the part that allows you to take the risk but also forces you to do everything possible to avoid ending up in the trees at the end of the runway).

And sometimes the ability to be distracted is equally important.  The story that comes to mind is the learning to fly method described by Douglas Adams in the Hitchhikers Guide to the Galaxy.  In the end, the ability to fly is directly linked to the ability to fall and miss the ground.  And the only way to do that is to have the ability to be distracted in the moment before impact.

The challenge with definitions like these is that they evolve and are understood differently by different people.  And, as you can see from the lists above, we start with just one word, then one phrase, then several phrases, and then a paragraph, and still none of them feel solidly complete and accurate.

In my view, it is not a case of either this quality or that quality or the single most important quality.  It is really a multidimensional both-and structure.  It is everything in “the package” of the entrepreneur AND their team AND the landscape in which they are operating AND AND AND.  You have to listen and talk and walk around and see what you smell and see what you trip over as you explore the landscape around the Startup Company and its Leader(s).  And then you will hopefully have gained some insight into whether or not they have whatever traits are important for that time and place.  Just remember that it may not apply to later and elsewhere.


I found myself talking about “dumb money” today with an entrepreneurial friend. In our conversation, “dumb money” referred to money that came with hidden harm.

We could each tell stories of companies that were seriously affected as a result of taking “dumb money”. This one blew up (think detonation, not acceleration). That one imploded (think black hole). Another one sold for pennies (what’s the ROI on that?). And on and on.

As this article observed, entrepreneurs tie themselves with alarming frequency to investors who are actively harmful to their company. Just as the body can have a malignant tumour, companies can have malignant lines on their cap table. Start-up investors typically have tremendous power over their portfolio companies, generally over a period of many years.

So, how should an aspiring entrepreneur avoid the pitfalls of “dumb money”?

They need to know what to look for … (taken from here and here and here)

  • Smart Money is money plus the promise of help that’s worth paying for. This type of money is not damaging to the entrepreneur.
  • Mostly Money is mostly money. This can be called benign money and is not damaging to the entrepreneur.
  • Dumb Money is money plus hidden harm. This can be referred to as Malignant Money or Cancerous money. This type of money is certainly damaging to the entrepreneur

Then they need to do their due diligence on any potential investor. Don’t assume any investor won’t be harmful. Do the diligence to prove otherwise:

  • Do you trust him?
  • Is he going to waste your time?
  • Will he provide his pro rata in the next round? (Not so important for seed funds and angels.)
  • Are his financing plans aligned with yours?
  • Are his hopes for top line growth aligned with yours?
  • Will he support you if the company is going sideways?
  • Does he have impeccable references?
  • Does he want control?
  • When it comes time to sell the company, will he let you?
  • Will he let you expand the option pool to hire someone great?
  • Does he want to replace you as CEO?
  • Will he try to merge you with a dying company from his portfolio?
  • Do you want to marry him for the life of the company?
  • Would he make the wrong board member?
  • Is he committed to investing in startups and does he have a reputation to protect in the startup world?
  • et cetera…

With all that said, I really like this advice from Venture Hacks.

Whether you raise Smart Money or Mostly Money, you should raise money as if your investors were Mostly Money. In other words, unbundle money and value-add.  Get money on the best terms possible and get value-add on the best terms possible.

You can buy advice and introductions for 1/10th of the price that most investors charge. An investor will buy 15–30% of your company. An advisor or independent director will require 0.25–2.5% of your company with a vesting schedule of 2–4 years.

Happy Hunting!