Business Opportunity: How should I go about this?

So long story short: I quit my job a few weeks ago to start my own company. Upon leaving on my last day there, I was approached by both my immediate supervisor, as well as his boss, who’s one of the highest-ups in the company. Both took an immediate interest in my new company and expressed an interest in working together once I got it up and running.

Well, that was about a month ago and here I am, just about ready to launch. What I’m wondering is how I should go about this. Should I email both of them at the same time? Or just my immediate supervisor, who I was much closer to than his boss?


Hmm, in general I don’t thinl we have enough facts to have any meaningful input. Let’s start with: why don’t you want to include your supervisor’s boss?

Well, I do want to include him. I just wasn’t sure if it may cause offense to one if I include the other? Almost as if I were going over his head, as it were.

Small business owner checking in…

#1 Do you have funding to support hiring them at any meaningful wage?
#2 Have you ever worked in any supervisory capacity before, esp one involving payroll and such?
#3 Why do two tiers of your superiors want to work for you?

It could be that they think you have the coolest thing since chunky peanut butter going on but I would seriously wonder why my bosses suddenly want to be my minions.

Sorry, I should have clarified this before. We wouldn’t be funding them–we would be providing content for their website. They’re interested in me because I was the only one who worked there and wrote the type of articles I did. Now my new site is based entirely around the same type of article I used to write for them, except now in video form.

But to answer your questions anyway:

  1. No. But again, if anything, they’d be paying us for the content.

  2. Not really–I do have a few people working for/with me now, but for free.

  3. Well, both were the heads of the editorial department, where I worked. Except my boss’s boss more so. I interacted with both sort of regularly, but I reported to my supervisor who reported to the head editorial guy. They both want to work with me because I rock and wrote great articles, but also they have no one to replace me for the time being, and working with my new site would be a quick and easy way to fill that gap.

Dear Name and Name,

Well, things are going great here, just about to launch the business and see how it goes. Naturally, I’m always delighted to discuss any opportunities for productive co-operation or collaboration, and I just wanted to make sure you had my contact details. All the best,

  • Sign Off

Agree. Send the message to both of them. Your OP sounds like they want to come and work for you. But I think what you meant to say was that after you got up and running the wanted to “do business with you”, i.e. have you be a supplier to them.

I myself would call them up and possibly go to lunch with them. Barring that, I would certainly send them an email.

You have two people in your field who want to send you work. This means you have them and everybody they talk to if you play it right. My advice is: let them send you work. Make it really easy and attractive for them to send you work.

Phone call is better than email here, imo. Order not as important, but call both. Courtesy on each call would be to let them know you’re talking to each so they can decide amongst themselves Who’s going to be your main contact.

Call them AND email them. Give them your website link. Send them any brochures or other related literature. Put them on your mailing list, etc.

Good luck. Have fun.

^^^^ This.

If I were you, I’d offer some sort of incentive to these guys for getting you new business in the form of a referral fee or giftcards to a nice restaurant or something.

At first, I was suspecting that they were wanting to steal your idea.

Now, I think that they plan to get free work from you. Free somethings, in re what you are doing. “Hey, Red, what’re you working on now? Uh-huh. Sounds great! Why not send me a copy?”

Could be wrong, tho.

Best wishes,