Ideas for Care Package

It's not homemade, but I've sent the mixed dozen brownies from Embrace Sweets many times and am told they're delicious. That way, it's may send a
"friendly, but not too friendly" message.

Maybe what he really needs is a box full of SILLY!? Like a troll, a whoopee cushion, chips, snacks, lifesavers, a pet rock, a play doctor kit, a stuffed animal, etc....just funny stuff. You could find things that were trends from college.....
OR what about sending him a floral arrangement for the business, candygram, gift card for a local restaurant, bookstore card, Beer-of the month club....I agree ask your hubby for some advice. have your toddler draw him a picture to include!

That is so nice of you! Cookies are always a hit. You can include a note that your toddler "helped" you. That would be a subtle reminder that you have a family, but not weird. What about sending a nice bottle of scotch? You could bubble wrap it. Maybe your husband could help pick something out? That way it is a family effort for a family friend.

Added: Please try to remember this is a guy. Ask your husband if you don't believe me, but it would probably weird him out to get something like a picture frame, or anything "sentimental". He's having a tough time, not turning into a woman.

How bout an inspirational thought paper weight for his desk so that everyday he can look at it and remember that he has people rooting for him. I really like the "Bee Happy" Bumble Bee cookies too! And of course some money for beer.
Check these out:
http://beta.gifts.com/search/product/Personalized-Graduat...

I know that these were in the graduation category but they apply to personal success in life, not just grad. This site also has all kinds of gift baskets, desserts, wine baskets... etc...etc...

What a nice friend you are. A book that comes to mind is "We Got Fired ... And It's the Best Thing That Ever Happened to Us," by Harvay Mackay, "the best and the brightest tell how they bounced back, in their own words." Maybe a thought for searching for a book on Amazon. A thought triggered from a suggestion below . . Bamboo plants are also a symbol of prosperity. They used to sell them on Red Envelope along with some more manly ideas.

I like the *silly* ideas and the "toddler helped me" ideas and I think cards & sweets are great so I was thinking you could combine those things. Make a giant poster of a card and write out a story of how you're feeling and how you wish you could help cheer him up. As an example: You could start by saying "It sounds like you're at the end of your (and then attach a red rope licorice) so I thought I'd try to (then attached a megaphone with the word CHEER) you up!".. Get it?
Good luck - to you both. Nice friendships are important =)

Statistically speaking, most new businesses fail. I would also say that just before succeeding... things look very very grim. It's making it through this period that seperates the winners from the losers. It's important to keep his fortitude up.
Maybe you could find a good book on business stories that actually made it but didn't think they were going to, or businesses that made a turn around, and include that as a part of your package. There's also a slew of books on how to find your calling... but those books can also be the type to inspire balance that he may need right now in terms of keeping things in perspective. I'm sorry I can't think of any specific titles, but Amazon can probably help.
I also love to send care packages from Zingerman's in Ann Arbor MI. You can google them and they make all types - perhaps you could send some gourmet coffee for burning the midnight oil... some sweets to help him feel better... something like that. They ship anywhere.
You could also look up an Asian themed "charm" to send - I am not sure what that would be - but you can google it and pick up a jade symbol on a red ribbon for good luck and prosperity.
Perhaps a funny movie that is business themed? Something to take his mind off of it for a bit...
Good luck.

You could put together things like: a movie, w/candy, microwave popcorn, soda, add some playing cards, crossword puzzles, etc. Just put together a bunch of little things and then write him a little note letting him know that you are thinking about him and hopes this will cheer him up. Let him know you hope things turn around for his business. It doesn't have to be anything extravagant. Good luck.

maybe a saying in a picture frame.. like you can do it.. or something like a mug with hang in there... and maybe a few scratch off lottery tickets... just wish him good luck.. tell him to hang in there and you are available to talk... tell him your sending him a great big hug...

how about a mixed cd--really upbeat music? and maybe a drawing from your child too? i like the other ideas below too!

A good joke book? Did he used to spend time playing an instrument or being artistic? - maybe a music book or art supplies.

You are a very good friend to think of this for him. Perhaps a nice card would go along way to say how much you care. Package ideas would be anything that you think would make him smile, pictures of your child doing silly things, a few strips of his favorite comic, a dvd of his favorite movie and a bag of popcorn, a good book, a cd of his favorite band or a cd of music reminiscent of the time when you lived closer (ex. sound of the 80's) a souvenir from the past (or a recreated one) that is attached to a fun memory, mardi gras beads / trinkets, a smiley face pen. Given the qualities you listed anything out of the ordinary should work great, the idea is that you care and are thinking of his well being, not so much about what is in the box.

Sometimes just a good thinking of you card does wonders, he knows your are there and thinking of him. Maybe a giftcertificate to a favorite eatery so he can go out and "treat" himself with a freind.

I have found some fun and funny care package ideas in the articles here
http://www.celebrationideasonline.com/college-care-packag... I know he is older but fun and warm thoiughts are appreciated at any age.