I’ve been a big fan of the Hobbit since I was a little kid, and it’s gratifying to see my favorite characters brought to the big screen. I feel like I’ve been journeying with Bilbo Baggins in my mind for as long as I can remember, from the soft meadows of the Shire to the warmth of the Last Homely House of Rivendell, through the depths of Mirkwood and Laketown, into the Den of the Dragon itself, under the Lonely Mountain.
- Gandalf sees an opportunity and recruits a CEO. In the new scene, Gandalf meets Thorin in Bree ("this isn’t an unexpected meeting, is it?"), and convinces the Dwarf prince to go on the journey to reclaim his homeland. Gandalf is seeing a bigger threat to Middle Earth – a broader market if you will, and he sees that Thorin's background would fit nicely, if he could be convinced to run this one adventure. An effective VC or advisor keeps his or her eyes on the broader market opportunity, and really great ones will actually encourage entrepreneurs to start companies to take care of specific niches in this broad market.
- Gandalf sees something in Bilbo that others don’t. Gandalf decides that the Company needs a burgler, an everyday sort who can get in and out of the Dragon's Den without raising suspicion and inviting disaster. The others think that Bilbo doesn’t have the courage or werewithal to go on such a journey (neither does Bilbo himself!). A good VC or angel investor or advisor can sometimes see things in us (or in team members) that we might not see in ourselves. I've often thought that that people really knew how difficult running a startup can be (compared to the popular concepts), many would-be entrepreneurs would never start. But as in Zen, not-knowing is a good thing, as it allows us to come up with fresh solutions to the problems that crop up, which is what happens with Bilbo before the end - all because Gandalf saw something in him that he didn't see in himself.
- Gandalf convinces people to do things that will help the journey, whether they know it or not. In the movies, it’s clear to Gandalf that they need to go to Rivendell, though Thorin is resistant and doesn’t want help from the elves. Gandalf also recognizes that if Elrond knew the true purpose of the dwarves journey, he might not help them at all. Finally Gandalf realizes that if the dwarves ask the White Council for permission to go on the Quest, it will be denied. In my opinion, this is one of the great ways that we see Gandalf’s age, experience, and knowledge of human (not to mention dwarvish and elvish) nature really shines through in the movies (even if it deviates slightly from the books). He gets Thorin to go to Rivendell out of need, he withholds enough information from Elrond so that he helps to decipher the map (a moment that Peter Jackson says gets Thorin to “truly” trust the wizard implicitly), and then counsels the dwarves to leave before the Council can tell them no! Sometimes in startups, people don’t see the whole picture – they just see their little sliver, and it’s necessary for someone (preferably someone older and wiser who can see the big picture) to show them partial views, until they are able to embrace their role and grasp the bigger picture.
- Gandalf’s prior contacts get the company out of many scrapes and keep the Quest alive. Without Gandalf’s prior contacts, ranging from Lord Elrond to the Eagles to his knowledge of Beorn, our heroes would have been toast – literally in the scene with the Goblins and Wargs setting the trees on fire. It turns out that in a past life, Gandalf had helped out the king of the Eagles, and this brings the Eagles in to help the company get out of the frying pan and the fire! Whether it’s making an intro that leads to a big customer or to an acquisition, or bringing in extra cash to keep the company alive, a good VC or advisor utilizes their rolodex and previous relationships to help out the team in ways they couldn’t do themselves.
- Gandalf steps away to let Bilbo and the company spread their wings. At certain points in the adventure, Gandalf steps away from Bilbo and Thorin and the Dwarves, off on urgent business. It’s during his time away that Thorin and the dwarves really develop confidence in themselves and particularly in Bilbo. Moreover, Bilbo develops confidence in himself and saves the party several times. It’s important that any startup founder or CEO or leader be able to deal with situations on their own, without always relying on their advisor, mentor. Sometimes this leads to mistakes, but overall it builds the courage, character, and inventiveness of the team. A good entrepreneurial team, no matter how they start up, should end up with much more wisdom, self-knowledge, and confidence in themselves by the end of the journey, whether he venture is a financial success or not. A good advisor or board member knows when to step away, and when to engage more deeply.