Create + Cultivate is a creative conference you founded for female entrepreneurs in the digital space. Attendees and speakers came from around the U.S. to be inspired and network, but what is something you took away from the day?

I think everyone thinks we have it figured out, but we’re such a tiny team and we’re new to this as well! I’m constantly learning. One of the panels that I really enjoyed was “Getting Niche: Finding an untapped market and creating a unique brand online”. As much as I love personal style [blogs] and all that stuff, I think the future of blogging is the sites that don’t require the person to be there to operate. [For example,] P.S.- I Made This could run on its own eventually, and that’s what I aspire to. I want Create + Cultivate to run on its own; I don’t even need to be there … I had a blog back in the day and it wasn’t going to run on its own. It had to have me in it, and I had to be the face of it. I just thought that was really good advice [to create a brand bigger than yourself]. I think everyone thinks they want to start a fashion blog, but it’s important to start something new and fresh.

Every step you took at the conference was an Instagram-worthy moment. I take it that was by design?

Exactly. That’s something we do for a lot of our clients [at my branding and consulting agency (No Subject)] too. When I go to events I think, “I want to talk about being here,” and sometimes there’s nothing pretty [to take a photo of]. Instagram is so visual. It’s beautiful, bright and clean. When we’re planning the event we’re always trying to create big patterns. We had that giant cacti wall, which was a huge investment but huge reward. We’re always trying to think about how can we create beautiful signage, beautiful florals and integrate them into the shot. During set up we’ll post some of the Instagram-able moments. They’re little teasers that get in your head and you know that that’s something that photographs well.

Aside from patterns, biggest tip for a great Instagram?

Lighting. Lighting is so important. If you go to a dark dinner or dark event you can’t shoot anything without it looking really awful. We had to uplight. The middle room was super dark, so we had to flood that room with light.

You launched your marketing and events agency, (No Subject), in 2010. When did you have the vision for Create + Cultivate?

It has grown so much over the years. It started as a partnership with Ace Hotel in Palm Springs. They approached us to program their Sunday nights. They weren’t getting a lot of people booking on Sunday nights. I thought, “Who can not go to work on Monday? Freelancers!” Freelancers make their own schedules. L.A. is a town of freelancers so I thought, “Let’s do a freelancers getaway.” And that’s how it started. It was a very similar format, but way smaller scale.

At what moment did you realize it could be big?

We thought about it as this side project. And then we just kept getting e-mails asking, “When’s the next one?” I think this was a theme of Chicago’s Create + Cultivate a little bit. When something just keeps getting your attention and momentum is happening you have to listen to it. You shift gears. We weren’t really thinking of it as a whole separate entity and then we brought it on the road. I thought, “Let’s take it and see what happens.” We did Portland, Montauk and Brooklyn. Again it was a smaller scale of 50-75 people. It was a press darling; press kept reaching out to us. It was gaining so much momentum and then last year I made the decision. I was like, “Alright, I’m gonna invest some of my own money into it. I’m gonna go boom or bust and just see if it takes off and if it doesn’t, whatever. No big deal. It was a fun experiment.” And then after L.A. I thought, “Oh my God. This is something.” We had 350 people in L.A. and 500 people in Chicago.

Why did you choose to come to Chicago?

Chicago is such a vibrant city of food, art, culture and fashion. We were so impressed by the startup scene, the caliber of content creators and the network of ladies— it was a no brainer!

Was there ever a moment you felt like the world was over when building your business?

My moment is pretty specific, and I don’t talk about it that much. I had a business partner. I had a business partner for the first few years and needless to say, money issues arose and money was in places it shouldn’t have been. I was 24 and we were having a great time. Our business took off unexpectedly. At the time I was so devastated because what had happened was so black and white in front of me. I had to make some really tough decisions friendship-wise and business-wise. It was one of those things where I felt like this had only happened to me. After I started talking to other people and they’re like, “Tale as old as time,” it made me feel so much better … It was a real life lesson. I literally went to classes on finance and business – YouTubed everything I could learn about QuickBooks … It’s one of the reasons I started Create + Cultivate. During that time period I had no idea what to do. I was literally so devastated. Female– even male– business partnerships and the things that go along with it is something I love to explore. I was not set up properly when I launched (No Subject). When I’m asked, “What’s your advice for entrepreneurs?” It’s not, “Be yourself. Be authentic.” I’m like, “Get a good lawyer. Get it in writing!” It’s the biggest mistake everyone makes.

Do you have a vacation spot you frequent when you need to unwind?

I haven’t been on a real vacation in so long. My boyfriend and I go to Ojai a lot. It’s one and a half hours north of L.A. It’s super close, so you’re not in the car for six hours. We bring our dog with us. It’s a gorgeous vineyard, farm town; there’s a really famous spa there. You just feel like you’re in another world. We go there quite a bit.

How did you meet your boyfriend?

We met on Tinder! I tell everyone that story because I was single for two years. I was barely on Tinder, I would just do it for fun. Maybe talk to someone every now and then, but he was super persistent. I almost canceled before our date. I just went in jeans; I never wear jeans. I’m usually in a dress. I did zero fuss. We went to get a drink and I thought, “This is kinda amazing. This is awesome.” Later we ended up hanging with my friends all night on our first date. We’ve been together ever since. We just moved in together. He did the big leaf painting [at Create + Cultivate]. He does all the graphics for Create + Cultivate.

Did you imagine you’d be with someone in the creative world?

No. My ex-boyfriend was a business owner– totally different industry. It didn’t work. It was really interesting because I felt like it was constant competition in a weird way, and no one was providing the balance the other person needed. David, my boyfriend now, is a graphic designer. I love graphic design and we bond over that. He’s a little bit older and wiser in a sense that he’s very good at saying, “You need to shut your computer and we’re going for a walk. You need to disconnect.” There are nights where I’m literally like, “I need to work all night.” And he says, “Here’s a cup of coffee.” He’s supportive both ways. One thing I like is that he gets excited about what I’m doing and gets it, but he’s not like, “I know this blogger.” He’s barely on Instagram. He’s so not connected to that world, and I think that’s really nice for me because I can go home and we don’t ever talk about it. On our first couple of dates we didn’t talk about work at all– which I thought was impossible. He’s just super normal. There are so many crazies in L.A.

Where did you and your team stay in the Windy City?

We got an Airbnb. It was awesome. It was near Wicker Park by the Blue Line station. Do you know where that coffee shop Big Shoulders is? It was a beautiful old school house: super narrow and three floors.

Is there anything you want to do differently at your next Create + Cultivate?

There are all sorts of levels of people attending, which was another thing that I think is interesting. I really want to integrate some higher level panels like raising money if you’re past the step of launching your blog.

From the outside it looked like a seamless event, so cheers to that! Were there any behind-the-scenes fires you had to put out?

We have this awesome pink neon Create + Cultivate sign. We spent so much money to get it there. When we opened the box it was in a million pieces. It was the last thing we opened on the night of set up. The main stage was going to have the neon sign instead of the white sign. I was so excited for that picture moment with the sign with everyone, so I was super bummed about that. I had to get over it and just move on!

If you could have a drink with anyone, who would it be?

Joan Rivers. I feel like it has to be a dirty martini if it’s with Joan. I’ve always loved her. She’s hilarious; she was always amazing. I watched the documentary “Joan Rivers: A Piece of Work” and it was such a game-changer. People think of her as a raunchy comedian. She paved the way for so many people. She’s just such a legend. And talk about someone who had a million “No’s” thrown her way. That perseverance is so incredible.

KIRSTEN MICCOLI PHOTOGRAPHY / A DRINK WITH AT HOWELLS & HOOD