The Gentleman Entrepreneur: Accessorizing via Startup

I have a new term I think needs to enter the popular lexicon.

“Gentleman Entrepreneur” – one who comes from wealthy background and so doesn’t need to work, but dabbles in new business ventures as it’s the latest form of intellectual credential. Commonly has far-fetched ideas that are only reinforced by “yes men” mentors and friends, stronger than normal emphasis on disruption and changing the world, doesn’t work very hard, and the startup primarily serves as an answer for what they do with their time and as an outlet for intellectual masturbation.

You see these people in the entrepreneurial ecosystem a lot, and they waste a lot of time. For them, their business is an accessary – a Prada backpack, a Supreme T-shirt, and a start-up.

Here is your guide to how to recognize them:

Key Traits:

Wealthy, or Seemingly Have A Sugar Daddy of Some Sort: Yes, most entrepreneurs come from privileged backgrounds, but there is a difference between graduating college debt-free and having a trust fund, or a wealthy backer that just believes in you so much you get a blank check. The Gentleman Entrepreneur has no pressure to worry about things mortals need to, like rent, and so their timetable stretches out forever and they don’t apply any pressure on themselves to refine their ideas, hence . . .

Farfetched Idea: A social network based around some social good, an app to solve homelessness, etc. A new blood testing method. Usually unbelievably broad in their application, Gentleman Entrepreneurs are never building the next recruiting CRM, or well, something people would actually use. These ideas are never challenged substantially because they have . . .

Yes-Men Mentors: Often their mentors have nothing to do with their industry, are referred to in general terms like “he was a high level exec at a fortune 500 company,” disguising the fact that the company has nothing to do with what they are buliding. The advisors are there for a similar reason the Gentleman Entrepreneur is starting his “business” – because they like the idea of it, the ego stroking that comes from advising a startup or a “revolutionary young man/woman.” Most of their advisory meetings have no challenging of ideas or assumptions, and are useless cheerleading and back-patting sessions.

Highfalutin Language & Discussion: Disproportionate use of words like disruption, innovator, change. Maybe an occasional reference to the Singularity. Likes talking about big ideas, with no real big interest in a practical first step solution to start solving the problem in a granular way.

Frequent Conference Attendance: Corollary of this is “Frequent Speaker at Conferences You Have Never Heard Of.” The Gentleman Entrepreneur is focused on all the trappings of success without any real success and never misses an opportunity to have a photo taken of them waving their hands with a mic on their ear. Definitely has gave a TED talk (it was actually TED-x Drexel University but same difference . . .).

There are common examples of this phenomena:

1) The Social Change Gentleman
Interested in a cause, from climate change or impoverished children, or something incredibly ill-defined and general like “human happiness,” and a ridiculously out of touch way to solve it. Went to burning man and has unrealistic expectations on how to integrate a barter economy back into mainstream society.

Archetype: Anyone who starts their pitch with a story about Burning Man.

2) The Party Gentleman

Starts a business that is mainly about him meeting and sleeping with women. No downside if it fails!

Archetype: Billy McFarland (Fyre Festival Dude)

3) The Hollywood Producer Gentleman
Daddy made his money in another industry, and the son went to USC or NYU film school and now has money to “invest” (read: throw away). Wastes people’s time because he doesn’t really know how the film industry works, and doesn’t want to do the hard work to figure it out. Even better variation adopts a social cause and produces documentaries, overlapping with the Social Change Gentleman.

Archetype: Kony 2012 guy.

4) Sugar Daddy NGO/Startup Gentleman
A less common variation is someone who actually isn’t wealthy, but they’ve managed to convince some wealthy backers, often around a social good, or just because they are so damn inspirational, to fund something that allows them to live like they have a trust fund while Instagramming from Davos.

Archetype: Elizabeth Holmes. Not wealthy but boy did she have a lot of old rich dudes (who were all from unrelated industries and yes-men) eating out of her hand . . .

5) The Early Unicorn Employee (credit to Pete Kazanjy for this one)

Early stage lottery winner from a company like Facebook, Google, Uber, etc. where riding the rocket ship is mistaken for steering/building it. Their second act is usually starting a company that raises easy funding due to their previous track record, but they have no pressure to succeed because they are sitting on a few million and once they realize there is a big difference to being Uber’s employee #300 and starting your own company, they just milk it.

The key for all of these people is this – they don’t HAVE to succeed. Whether they have money or not, their business is an accessory, nothing more than a fancy bag for them to pull out and show off at a cocktail party.

Avoid them.

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

This site uses Akismet to reduce spam. Learn how your comment data is processed.