red-carpetThere are no shortage of examples of how and why startup celebrity integrations don’t work. Most are misaligned from the beginning in terms of the expectations of both parties and the compensation changing hands. Giving up a significant chunk of equity can be demoralizing to a startup and yet of little motivation to most celebrities unless success is obvious early on. And paying for endorsements is tough because those celebrities you can afford, you don’t want, and those you want, you probably can’t afford. Without the proper incentivization, celebrities are unlikely to put in the time and effort necessary to make an integration truly worthwhile.

So does this mean that working with stars is always a bad idea? If done traditionally, the answer is nearly alway yes. But there are some creative alternatives that can make things interesting for everyone involved.

Los Angeles-based custom shoe startup Milk & Honey has been rather effective in combining celebrity and charity. The Launchpad LA alumni company has previously run campaigns with Ginnifer Goodwin, Kate Mara, Malin Akerman, Rachael Ray, Amber Valletta, and AnnaSophia Robb in which the celebrity personally designs a shoe which is then featured on the site and the proceeds of all sales of that shoe go to their charity of choice. Today the company is rolling out its latest celebrity design from Whitney Cummings, star of NBC’s Whitney, to benefit her charity Operation Smile.

The model is a win win for both Milk & Honey and for the celebrity. The startup breaks even on each sale, and gets significant publicity and brand value by being associated with these highly fashionable women – which it otherwise could not afford to work with. The celebrity, on the other hand, gets a fun and authentic way to express themselves while doing something positive.

Co-founder Dorian Howard, one half of the duo behind Milk & Honey along with her sister Ilissa, has the advantage of coming from the Hollywood world, having previously worked in production for Paramount Pictures and New Line Cinema. This doesn’t mean she can pick up the phone and get a hold of anyone she wants – although she’d likely be more effective than you and me – but more importantly she gets the “rules of celebrity.”

“Celebrities get offers in every category and across every channel all the time,” Howard says. “And they get free stuff all the time too, most of which ends up going to their assistant or friends.” The young executive recognizes that to a celebrity, their brand is their greatest asset, meaning they’re unlikely to align themselves too closely with a risky early stage business, lest it fail and their image get dragged down along with it.

In a charitable context, it’s much more difficult to come off look bad. Every shoe purchased gives more money to the charity, but no one is standing there with a scoreboard measuring campaign effectiveness. It’s fairly close to a win, win.

One thing that pleasantly surprised Howard was how personally involved each celebrity was in designing their shoes. The company offered to do the heavy lifting of creating a few custom designs from which the stars could choose, but were rebuffed at each turn with the stars insisting on coming into their design studio and being personally involved in the process. These are fashionable women after all, and creating custom shoes isn’t something you get to do every day.

The other thing that the Howards did right was to make the experience as easy and non-threatening as possible for the celebs. There was a strict no picture taking and no autograph requesting policy around the office. And there were no gushing blog posts written about the experience either. By keeping it casual, they ensured that the women didn’t need to worry about hair and makeup and a stylist before coming in to create their designs.

Milk & Honey has been introducing a new celebrity design each quarter as of late although that will likely accelerate to a rate of every six to eight weeks. The campaigns have been popular and they have been equally effective at driving women to the site to create their own custom designs, as they have been at selling the charitable shoes.

The company isn’t the first brand to integrate charity into their DNA. Toms and Warby Parker have built their entire brand identity around giving back. Similarly, H&M’s “Fashion Against Aids” and Gap’s “Product RED” have offered strong examples of authentic corporate charitable initiatives. Celebrities have integrated fashion and commerce into their social campaigns as well, such as Rachel Roy’s Hearts for Haiti earring line introduced after the 2010 Haiti earthquake.

“Obviously, one benefit we get from being a start-up in LA is our proximity to celebrity,” Howard says. “If we’re not going to be in the fashion capital – NYC – or the VC capital – SF – then we need to highlight what LA offers. We were shocked how accessible celebrities are when you give them something that’s actually interesting to them.”