WWW: Tell us about a scenario in the past where you wish you had an app like this to help guide you.

SS: Well, first of all, there are more scenarios than I can probably count. I think, for instance, I live my life on the go, and I’m not always in town when I’m filming; I’ve been filming out of state the last couple of years. You’re flying back and forth with really short turnarounds to go to these events in Los Angeles or New York. Sometimes I was in such a rush that I didn’t really get to think about the choices I was making with my outfit or hair and makeup; I was always so busy moving through life.

We’re all busy, but no matter how busy we get, we want to feel confident about how we look, because it can be really vulnerable if we don’t feel good about our look or our outfit. It can really sort of shake our experience. In the moments where I’ve been on the go, I would have loved it if I could have reached into my purse and gotten a second opinion on hair and makeup, feeling assured that I was rocking the perfect lip color for the dress I was wearing. It’s just that little boost of confidence that makes you feel like you’ve got this.

WWW: Tell us about the process of executing your business plan. What were some of the challenges that surfaced along the way?

SS: It’s no cakewalk; I’ll tell you that much. It was a really incredible process, learning the ins and outs of putting a business together. It was really the first time I had done something like this. Andrew has launched a few businesses before, so I was lucky to have his guidance throughout the process.

I think for us, one of the biggest challenges is that Tipster is a multifaceted app: You have a portion of the app that caters to users—people asking questions, seeking style advice, and wanting to cultivate inspiration for their own personal style. On the flipside, you have the stylists, makeup artists, and fashion influencers who are looking to monetize their followings from Instagram and other social media sites. They’re also have very specific needs, as far as building their portfolios and having a space dedicated to building their brands.

So you have these two complex pieces, and finding a way they can work together harmoniously—whereby the stylists are getting as much from Tipster as the users—was our biggest challenge. But we were able to do a lot of research; we interviewed a lot of people, and we reached into my Rolodex, where stylists and artists I work with all the time came in and did beta testing with us. It was really great, and we’ve had really good responses. And that’s sort of the magic behind Tipster.

WWW: How exactly does Tipster work, in terms of getting paired with a stylist? How did you go about securing a team of stylists?

SS: To me, selection is key. The first thing we talked about was, “It has to be the user’s choice.” For instance, a lot of people have called this “The Uber of Styling,” and I always say, “Well, sort of, but with the caveat that you get to choose.” With Uber, you just find a driver nearby. With Tipster, you get to choose the stylist you want to talk to.

We have a very specific vetting process, going through and making sure that all of our stylists, artists, and influencers are experts with legitimate portfolios. They either have a presentation or body of work that show they are experts in their field or they have amassed a certain amount of Instagram followers that we can really trust that they’re legitimate.

So we go through the process of making sure everybody is qualified to be a Tipster, and from there, we use specific information that the stylists put in about themselves—their specialties, areas of expertise, styles they identify with—and we pair that with the overlapping interests and preferences that users input when they develop their own profiles. When a user is looking to ask a question, we match them with the stylists who we feel overlap them the most.

So, for instance, when you ask a question, the 10 most relevant stylists pop up based on your preferences. Look through them; if you don’t see anyone you like, hit refresh and we’ll give you 10 more options. It really is a personalized experience that way. If you come to Tipster and you don’t have a burning question in mind—maybe you’re just looking for a little inspo—our feed features lookbooks made by the stylists.

Every stylist, artist, and influencer on Tipster can make lookbooks on their profile, and these lookbooks are little glimpses into things they’ve done, including photo shoots, people they have dressed recently, or just something that’s inspiring them. Lookbooks are constantly being added to the feed, so you can see what people are posting and discover style trends as well.

WWW: Hypothetically, if we were to be paired with a stylist who we want more tips from in the future, do we have the option of consulting with that person again?

SS: Absolutely. So let’s say you have a really great experience talking to someone; you can go to their profile page directly and request a consultation with them.

WWW: How long has it taken to put Tipster into action?

SS: The idea surfaced two years ago, but getting the app up and all the details in place has taken about two years, and we’re still fine-tuning. It’s definitely been a labor of love.

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