Dear Jewish Fairy Godmother:

For years I worked for an executive who was very high-powered and
driven. Over time he began to lose his ability to do his job well and
eventually sold the company to younger folks. Five years later they
have paid him off and bought him out and essentially retired him. But
because he doesn’t know how to do nothing he has come up with a
plan that he started out calling “middle class services,” a name I have
convinced him to abandon. His theory is that double-working
households need cheap labor to do all the errands and chores that
they don’t have time for during the week, so they can have some
quality time together. Great theory. But he wants to set up a college
dropout into business to provide the kind of services the kid provides
him to others. That means going head to head with established
concierge and care companies, of which I found several with excellent
reputations and lower prices than he is proposing, all in a two-minute
google search.

He wants me involved as the lemon-sucker and offering to pay for
my time. I think the kid is just nodding yes to the guy who pays him
now, and is too lazy to build a business upon. I don’t mind consulting,
but I do mind batting my head against a wall knowing it is going to
get bloody and bruised.

The Assistant (No More?)

 
Dear Assistant:

You can earn your keep as you did in the past: by being a truth-telling,
lemon-sucking consultant. Before anyone starts a business they need
several important thing. In rough order: an idea for a product or
service that people want; an idea that’s not already being sold by so
many people or so cheaply that there’s not room for more
competitors; enough capital to get the process going and to outlast the
start-up period; intelligent committed staff who are willing to work
extra hard without a guarantee of success; and sufficient
communication, bonding, and common vision among owners and
employees that the folks on the ground can tell the folks upstairs what
needs to change, and the folks with the money can decide how much
they want to commit.

 
In this case, either you or the proposed employee can research the
market and suss out who is already providing those services. The
would-be entrepreneur may falter at your news. If not, he should take
a couple pages out of the multi-level- marketing playbook. That means
identifying all possible people he could approach or the erstwhile
employee could approach in his name to say, Hi, so-and- so has been
employing me to so x, y, and z and thought you might want a personal
assistant too. If he can connect with enough folks who will pay for his
time to fill up the FTE he is willing to work, you’ll quickly be able to see
if he is cut out for marketing and working. But if he’s just looking for a
middle management paycheck, it’s a great time to learn that you don’t
get to the middle till you start at the bottom.