From Rock Bottom to Blueprint: Building a Business with Audacity and Resilience

To date, we've done about 500 weddings, so we've definitely had some crazy ones. One of the craziest, I'd say, is an Indian wedding. We planned it from start to finish in 2 weeks. It was in Malibu at this private estate. The company who was putting this together didn't bring enough sandbags, and this was on a helicopter pad, so super, super windy. And so it almost fell off the mountain. And meanwhile, the bride and groom are over here taking their photos, like, totally unbeknownst to them. So I had my assistants, like, hold the mandap down during the ceremony, the hour-long ceremony.

Danielle, welcome to Driving Impact, the Top 5% Method. I'm so excited to see you today.

Thank you so much for having me. I'm so excited.

And are you joining us from Joshua Tree?

Yes, I am. Technically Yucca Valley, and out here it's very important to distinguish Joshua Tree versus Yucca Valley. But yes, we're in the high desert.

That's amazing. I don't know the difference, so you'll have to educate me later. So I'm joining you.

Will do. I didn't either.

I know everybody has these little quirks. So Pod and Collective, today And we have Danielle Leilani, who's the founder— first, she's a celebrity wedding planner, and she's also the founder of Leilani Social. So Danielle, please tell me more about you.

Yes, uh, well, you did a good intro there. Danielle Leilani, founder of Leilani Social. Um, what started as a wedding planning business almost 10 years ago has kind of evolved into a lifestyle brand. So now we work with brides, we work with brands, uh, we now launch products, and Most recently, we're working on starting a venture fund to work on funding some of the brands that we work with. So one of my main passions is working with brides, and I've always been into girl power. I have like fun anecdotes about that from when I was little. But now we've kind of expanded. So we work on both sides, you know, doing weddings originally, we work with a lot of brands, you know, and as much as important as our couples are, so are the brands that we work with. So now we're kind of serving both sides.

I was reading the US— USA Weekly newspaper and I don't know, I got like so excited because they said the wedding planning extraordinaire is the go-to girl for celebrities, influencers, and everyday brides. And I was like, you make me feel like I need to get married again.

I love that. Oh, well, if I can inspire that in women, that's exciting. You know, marriage comes with its challenges for sure, but and opportunities, right? But planning a wedding is so, so fun.

So what are some of the celebrities that you helped organize their wedding?

Yeah, the first celebrity we worked with was through a referral from one of our brands. It was a band that we had worked with on a wedding in Orange County, just randomly. It was the couple had found that band and then they had hired us. But we really had great rapport and we worked well together. And so years later, I got a random call from Jason Earles. He was on Disney Channel's Hannah Montana alongside Miley Cyrus. And I remember I drove to LA to meet with them that day. So it was exciting. That ended up being in In Touch magazine. That was only our first year in business. I think it was about a year into the brand. So that was a big deal for us, kind of launching us into that realm. We've worked with Jillian Rose Reed. She was on a show called Awkward on MTV. Morgan Simeoner. She was on a Netflix show called Cheer. I was a cheerleader and a cheerleading coach for a long time, so that was a really fun one. And yeah, we've been really, really lucky in that, in that space.

And how did you get started in wedding planning originally?

Yeah, so I went to school for journalism and anthropology. I was the first person in my family to attend college. I was raised by a single mom, so we were just kind of winging it. I really didn't have much guidance as far as, you know, go to school, study this, and then this is going to lead you to this certain path. So I kind of went in blind. I just studied what I wanted to, and that randomly led me to wedding planning. Interestingly enough, I really use my degrees in various ways through not only wedding planning but building and growing and leading my company. Um, but yeah, during college I had an internship with an event planning company. They were more corporate And then I still was pretty set on being a full-time writer. So I actually pivoted and started writing for the Orange County Register. I was a cheerleading coach and then took me a few years to circle back to events. And I had an epiphany. I actually was on a road trip with an ex-boyfriend and we had a conversation and I was kind of having what I call a quarter-life crisis. I was saying, you know, this is what I like to do. These are my skills, these are my passions. I don't know how to put everything into one career path. And he said, you know, you'd be a good wedding planner, I think. He was actually a wedding photographer. I like to share that he was the catalyst to the idea, but I was totally self-made, I like to say. He was really into— girl power, you know?

Yeah.

But he was really into advertising online, so he really wasn't in the space of like networking and like meeting planners and, you know, like the networking side of business. He really just focused getting all his leads online. So he kind of instilled the idea in me. The next day I bought a ton of wedding planning magazines to really get inspired and then cold-called wedding planners that next week and, you know, gave my little elevator pitch on the phone. And then the rest is history.

It's amazing. And I saw some of the decors, like very bohemian. My— I think my wedding was in Catalina Islands. I lived in San Francisco back in the days. And one of my coworkers when I worked at Google, she's like, why don't you go to Katheline Jean-Pierre Islands? Because I didn't like to throw money right and left. I wanted to get married in Bali. And then we did this. I didn't know who to hire, so I found this girl. I had 13, we had 13 grooms and, and, and, um, how do you call these girls again?

Bridesmaids.

Bridesmaids. So the wedding planner got super overwhelmed.

It's a lot. You know, one of the biggest, the hardest things on the wedding day, I would say, is wrangling the troops, like the family, the wedding party. Obviously, you know, people are drinking, partying. And so I feel for her. Yeah.

What is like— I think if I think about my wedding, what was the worst was that suddenly all my friends became super clueless. So they were calling me like, how do I get a cab and stuff? And it's like, dude, this is totally insensitive. So I literally took my phone and I gave it to one of my friends and I said, this is your phone for the day. I do not exist. So I just— so what is it? What is one of the craziest wedding stories that you witnessed?

Oh my God. You know, to date we've done about 500 weddings, so we've definitely had some crazy ones. I've had uncles get really, really intoxicated, let's say, and they start fights at the reception. I've had grooms Uh, you know, probably things I shouldn't say on this podcast. Nothing too crazy, but we're in California, so maybe you could put two and two together. Um, but one of the craziest, I'd say, is an Indian wedding. We planned it from start to finish in two weeks. It was in Malibu at this private estate. And so Indian weddings, where they get married, it's called a mandap. So it's like the kind of like how American weddings have like an arch or a backdrop, they have a stage. It's usually a raised platform. It's beautiful draping. It's a structure that they sit in with typically their parents and the priest. Well, the company who was putting this together didn't bring enough sandbags, and this was on a helicopter pad. So super, super windy. And so it almost fell off the mountain. And so during ceremony— That's scary. Right? So scary. And I remember when it happened, one of my assistants came up to me and said, "Namunda fell." And I turned and I saw it like almost off the cliff. And meanwhile, the bride and groom are over here taking their photos, like totally unbeknownst to them. And so what I had is they had no idea. To this day, they probably have no idea. It'd be funny to reach out to them 10 years later and say, I have a fun fact about your wedding. So I had my assistants like hold the mandap down during the ceremony, the hour-long ceremony.

Oh my goodness. I mean, you're a great planner because you don't want to disrupt this moment. You want this moment to be magical. I think my funniest wedding story is so our first wedding, we got married at City Hall. And then we had a big one in Catalina Island. And at City Hall, there were some photobombers, like, somewhere in Asia. They all came. It's like a rotunda. They all came and took their phones. And just for them, it was like just a moment. Oh, they're getting married. They're kissing. I'm just going to take a selfie during the moment. And I was like, this is so disrespectful. I just thought it was crazy. They were shameless. They were like 10 of them.

They were shameless, right? It's like you're a tourist attraction. Kind of nice, I guess. Sort of flattering, but also like, please get out of my photos.

No, I'm happy I had more than one because otherwise I would have been so pissed off. I'm like, this is ridiculous.

No.

Okay, so this is amazing, Danielle. I love your story, but it hasn't been always that easy in your life because once you and I talked before, you said that you leveraged your rock bottom to create your blueprint to become your best self. So you turned pain into capital. Can you tell me a little bit more about What was that rock bottom about?

Yeah, you know, my life has been, I would say, filled with adversity. Everyone has struggles, but I was raised by a single mom. Like I said, she actually ended up passing away almost 11 years ago. So she passed away, I remember, about a year before I started my company and I had a wedding that weekend. And so, you know, that was definitely It was hard, but I loved that. I felt really grateful to have my career, something I was so passionate to fall back on, to not distract, but just, you know, to pour into. I think when we go through something hard, if we have something to pour into, to kind of, you know, we have to channel that energy somewhere. So that was definitely a difficult time. And I think part of that, you know, my company Leilani, her name was Leilani. And growing up, she always said, you know, Leilani is such a pretty name. I love my name. I wish that was your name. So it's my middle name. And so when I started my company, it was kind of an homage to her. So that was definitely a big piece of diversity. Most recently, you know, our company has really transitioned and I've done a lot of research on, you know, a lot of changes in my lifestyle. Like, about 3 months ago now, I started wearing all white clothing. I had been playing around with minimalism for a few years. So long story short, we went through an accelerator program back in 2023 to kind of learn about how to— because I was thinking about starting a tech project, which is kind of potentially still in the works for our brand. So a lot of our intellectual property can really best be used via a software or an online platform. So that's potentially in the works. But long story short, I went through an accelerator program to kind of learn the ropes and, you know, how to create a deck, how to pitch founders, kind of shifting from a mindset of small business owner, wedding planner, creative to a founder. So that was extremely helpful. I ended up going to New York City for 6 weeks. It was supposed to be a 2-day turnaround trip, But basically found a potential technical co-founder. That was a relationship that didn't work out. So last year, you know, kind of was, was in this one playing this waiting game, really, you know, obviously the brand was still running and the business was still thriving in some ways, but I was really ready to kind of pivot and take things to the next level. Like I said, lifestyle-wise, I was just getting really disillusioned by LA. I'd been there for 5 years. Originally in Orange County, wanted to taste that LA life, but really felt like it had run its course. So on Christmas Eve last year, I decided to get rid of 99% of my belongings in 48 hours.

That's a purge.

A purge, yes. I just gave it to the neighborhood. Like, people were coming, they would tell their friends. I didn't even want to sell anything. I just wanted to get rid of it. So in 2 days, everything was gone. People would tell their friends, they would come by the car full. I said, take as much as you want. And I set out in my Jeep. I'd always wanted to do Jeep life, van life. So that was a huge transition. That was totally by choice. I've always liked to do things a little bit against the grain, a little bit different. That was definitely the biggest kind of leap and challenge. And so I was living on the road for about 7 weeks. This place here is so, so inspirational. I really needed a new change of pace. A new lifestyle. And so when I say, you know, I've hit rock bottom or how rock bottom really led me to the next thing, I feel like sometimes in life, especially as a founder, you really need that, that catalyst to, to push you towards what's next. And living in a Jeep and moving from L.A. to the desert definitely was that for me.

That's a big deal. So what was the catalyst that made you, like, give away— like, most people try to sell their things— what made you give away your belongings? Live in the Jeep for 7 weeks.

Yeah, well, all of last year, I guess. Yeah, this is last year. It feels like years ago, but it was just last year. I really was starting to do a lot of research on just things, conspiracy theories, if you will, politics, what's going on in the world, our history as humanity. And we had started taking on a lot less weddings and events, so I had a lot more time on my hands while I was building this tech and working with this partner. Again, just really became disillusioned the more and more research that I did and wanting to kind of be a rebel in the sense like stick it to the man. Like, why am I paying all this rent in LA month after month? I just want to become basically go from zero and able to flourish in another way. So I think it just happened incrementally really since 2020. I remember back then I was speaking to one of my team, girls on my team, and I cried to her on the phone and I said, I don't I don't want to keep running my business the way I'm running it. I'm becoming very disillusioned. It's just, it's not too much. I'm a workhorse, but in the way that it was building, you know, we've been bootstrapped. So all the training, most of the client servicing is me creating the blueprint in which we train our girls. That's me, the marketing, the PR, the writing, copywriting, sales. It's a lot, especially without a solid team. And so people would come and go, you know, I felt very taken advantage of throughout the years. And so yeah, it had been, it had been a long time coming.

So it's what I'm hearing from what you're saying, Danielle, it's kind of like you wanted to free yourself, get, gain more freedom, because it's really— LA is a very expensive place to live in. It's expensive, everything costs a lot. And yes, it's not the only way we can live. Like, there's some podcasters and other people who just move to Dubai or move to Bali or move somewhere else. And of course, when you move somewhere else, there's a shift of energy. But I think also the exercise of letting go of everything and fluttering and then finding this, this different alternative lifestyle. I have a bunch of friends who are nomadic. Um, I went to the Tools and there was a meetup from the Tools at some point. It was like digital nomads. And then I was like, yeah, I went there and I'm like, I'm not a digital nomad, but I just want to see how you people live. I'm having kids.

Yes, so freeing.

If you have a kid and when you have a kid that has a school that's a type that's very hard to get into, and then you win the lottery and you're like, I'm gonna stay here forever. I think it's important to figure out what is this alternative lifestyle such that it's not like you don't have to do as this work, because I feel like the hustle part of work is the old school way of thinking. And I have a lot of friends who like strong-armed themselves to building their business and at the end, they feel shattered. So for you, what was the catalyst of this?

It's hard to pinpoint one moment because it really did happen incrementally. But I, you know, I think it started with feeling, you know, I was very grateful to, to find a full-time job in the industry for 2 years. So I was basically an executive assistant, lead planner. I started an internship program with that company. So I was really the intern coordinator. I was like the sales manager. For this small business in Orange County, and I worked there for 2 years before I started my business. So, you know, I had seen all sides. I had seen working with a small business owner and her relationship to me, my relationship with our interns, the intern's relationship with me and the company and the founder. You know, the climate has really changed. I would say this is back in like 2013. So in terms of what I'm trying to say is, you know, I feel very grateful and especially because I'm a millennial. I think, I think there's something about millennials where we, you know, we were in the age of like unpaid internships, paying our dues. And I do think the climate has changed. So long story short, there, I'd say one of the biggest things is really feeling taken advantage of, you know, there's, there are very few opportunities to work full-time in this industry, especially as a brand new person, a lot of like any job, any industry, right? They want to see on that resume, one year, two years, or more of experience. So I have always really been an advocate of giving people opportunity and wanting that to, to take them under my wing and train them, because I felt so grateful to get a full-time job when I first started in the industry. Another thing, I had only been in the industry for two months when I got this full-time job, so I barely— I had done as an assistant like two or three weddings. I really had to sell myself. I remember I did like two rounds of interviews and the business partner was like, so why should we hire you? You have no real experience. But I said I could do this, that I've done this, and I was a shop girl, and I was a cheerleading coach, and I, and I was a writer, and I was a, you know, I, you know, it's like I kind of sold myself. So, but I feel very grateful for that. And without that opportunity, I don't think that I would have started my own business so quickly, 2 years into a brand new industry at the age of 26, which in hindsight is pretty young, especially the relationships I had to build, um, you know, the team I was managing, the money I was managing for my clients, and just like the responsibility of handling 40 to 50 people's weddings in a year, you know, it's handling millions of dollars basically, and all the responsibility emotionally that comes with that. So yeah, that's a really long-winded answer, but feeling disillusioned by feeling taken advantage of, you know, I had come from a headspace of feeling very grateful for my mentors and where I'd come from. And, you know, without an executive team, feeling like I was training and retraining and retraining again, and then and, you know, really ran into some, some interesting things intellectual property-wise, like girls using our work as their own online, you know, I'd see people go off to start their own businesses and see them using our proprietary work, you know, on their, as they're on their own. That was another thing I was a big advocate of, you know, when I started my business, I didn't have anything in my portfolio. I had done probably 40 weddings, big Indian weddings, a lot of South Asian weddings. That's what the company specialized in. At the Montage, Laguna Beach, at the Terranea Resort, you know, really high-end weddings.

Terranea is so high-end. It's beautiful with the view, I think.

Oh, I know, right?

You got the first job also because it seemed like you sold yourself as you could do anything, and you, you've done a lot, which is a definite advantage. Why do you think they hired you?

Thank you so much. Um, I think my tenacity is something that I'm most proud of. And my confidence, I'd say. There was no doubt in my mind that I was the person for the job, and I sort of got creative. I think people get very stuck in, "Well, I don't have the experience directly, so maybe I'm not qualified." I kind of took the back door and I said, "Well, I may only have 2 months of experience with weddings, but I was a cheerleading coach at age 19, and I organized, I ran 20 middle school girls, a team of 20 girls. We had practice 3 times a week. I ran uniform fittings," competitions and, you know, as a teenager, really. And so, you know, once you start to think outside the box, I think more opportunities open up, essentially. Yeah.

And I have a similar story. And I remember somebody online said, but there's more to the story. Like, you talk about tenacity. What I'm hearing as well is resourcefulness. And so you're very tenacious, but you're resourceful. Thirdly, you disregard the impossible. They say that women normally would wait until they have every single bullet point on the job description to jump in, but you were like, I might have not done all these things, but this is what I bring to the table. And at the end, right, when you're an employer, you want to hire someone who can do anything because the job of being the right hand, even if you're a VA or an EA, So an executive virtual assistant or executive assistant, you're the right hand of the CEO and whatever they're doing, they need somebody they can offload to. So I can relate to that a lot because when I jumped out of corporate, I launched— when my podcast exploded with the top 200 in Apple's business podcast. But like when I hired someone, they're like, what do you want me to do? I said, this, this is— but that's a lot. I said, well, that's what I do.

Welcome to my world.

And they're like, well, I think that's a 5-people job. I said, I agree.

Right.

But so I don't like to see jack of all trades or the Jacqueline of all trades. Yeah, I think you were able to position yourself as the Jacqueline of all trades. So you started as a celebrity wedding planner with big names, then you pivoted into social media agency. Is that correct? How did that happen?

Yeah, so mostly working with brands, really. So, you know, lots of weddings. Working with couples is amazing. Working with families is amazing. And I will always be so, so passionate. And I mean, I always say I could plan a wedding in my sleep. You know, it's really second nature now to me.

You know who to call. Yes, exactly.

Yeah, I already have, you know, all our vendors that we love. I could plan a wedding really in like a week. Like give me a week and like show up and everything will be—

Anybody wants to elope, this is your moment.

Yes, we do quick turnarounds. And, you know, because I'm crazy, clearly, right? I love the challenge. Like one time we met, we were doing this Instagram campaign where we would find like influencer-like type girls that were posting on social media and offering wedding planning and coordinating. And one girl messaged at like 7 p.m. her time. She was on New York time. And she said, oh my gosh, I wish that we had found you sooner. We are getting married tomorrow in New York. So not in California. And she's like, we're getting married tomorrow, tomorrow in New York. And I said, well, we have a team in New York. If you're open, like, we could totally make this happen for you. And so we had our call with my planner in New York. Such a trooper. She was like, yeah, let's do it. I'm free tomorrow. Saturday was a Saturday. And, uh, yeah, we had our call at like 10 PM. I think it was like 1 a.m. New York time and the planner was there by like 7 a.m. her time. Oh, we executed the wedding and she was so, so grateful. She thought she wasn't going to have a coordinator, but I love doing stuff like that.

So yes, you, you're magical because that would just send people in a major spiral, like spiraling.

So there's something about my brain, you know, like a little chaos.

It's a lot of chaos. And I think the single moms— my mom was not a single mom. She was married. But she was the chief household officer and she could spin things on a dime. And that's sometimes a bit scary because you can take your time or you can spin it on a dime and you don't want to have a heart attack, you don't want to burn out. How do you— do you have any rituals to be able to be grounded, stay grounded, and take care of yourself while you're spinning all these wheels for people who want to have the day of their dreams or the campaign of their dreams?

Yes, I'm a huge advocate of wellness. So as much as I say I'm crazy and I'm a workhorse and I love to be busy, I think wellness, that's always really been important to me. So 8 hours of sleep at least a night. When I was younger, maybe that's a little bit more negotiable, but definitely now in my 30s, it's definitely more important. Also Bikram yoga. I've been practicing Bikram yoga pretty much on average, I'd say 4 to 5 times a week since I was in college. So that's been really grounding. I remember in like our busiest years, you know, and what I call Ilani 1.0, like when we're in Orange County and just starting and doing just like a crazy amount of weddings, me personally running around, I would always get to yoga, like an 8 PM class. I would work all day, maybe a couple meetings, maybe even a networking event. I would still go to yoga and then I would clock in again and work some more after the class. So yoga is really great. Make sure you're getting sleep. Drinking water is super important. And also finding— I'm kind of a loner, I'd say. But I think my advice for most people would be to have community. I do have community in my own way. I do like to— especially nowadays, you won't see me out and about as much. But I think it's important to have a work-life balance. Yeah.

And I think having community to support you, having kindred to understand you and I've been evolving with you as well. And what are your top 3 career advice or top 3 career advices for people who want to be able to thrive in their career?

Yes. One is, you know, actually, let me, let me, let me start with— so I had a podcast and it was called the Leilani Method, and the tagline was think big, live boldly. And make it effing happen. So I guess I'd go with those three, you know, like think big, think outside the box. Like we talked about earlier, don't think like if you don't have this exact skill and this exact skill, well, maybe you have these, these three skills over here that can translate well, you know. So think outside the box, think big, don't limit yourself, live boldly, you know, don't be afraid to go after your dreams. Sometimes that means asking for forgiveness, not permission. Having audacity.

Yeah.

Being okay with the fact that you might ruffle some feathers, you know. So that's thinking big, living boldly, and then just making it happen. You know, I guess they're all kind of related. I'd say making it happen is just not taking no for an answer, not thinking in terms of scarcity mindset, but more of an abundance mindset. Like thinking, just having, having kind of a ridiculous kind of level of audacity and confidence in yourself. Fake it till you make it is what I've shared a lot online, you know, obviously with responsibility. Like for example, planning weddings, like in the very beginning I sold myself for that company. I wasn't— I, I was very honest, you know, obviously they had to train me in on Weddings 101, but I started in that company, uh, November 2013, and then by March 2014, I think that's, you know, what, 5 months or so, I was already coordinating weddings. So you want to fake it till you make it. You always also want to make sure you're doing it responsibly, but, you know, it's all about mindset. If you think you can do something, chances are you can.

It's amazing. And then how do you ground yourself? So I know you do Bikram, but do you have any other practices that can help people stay grounded as they're aiming to be wildly audacious.

Yes, I'd say, you know, also stay very present. All we can do in this life is try. I always say I'm a trier, you know, what will be will be. I am spiritual, so I think on some hand, you know, like what is written is already written, you know. So don't take yourself too seriously, but try, you know, it's a fine balance. You know, you don't want to give up on your dreams, but you also don't want to be so rigid. I actually I say that now, but, you know, 10 years ago when I started in my career, about almost 15, 16, no, 13 years ago, 2013, you know, I definitely was like pretty intense and like very Type A and did ruffle some feathers and like came in like bull by the horns, like charging and, you know, was spiritual and like did my yoga and stuff. But I was still like pretty like tense. And so, you know, I think that comes with experience though. But if you can take one piece of advice from me in that realm, you know, don't run yourself ragged. I had experienced actually some health scares along the way, some skin condition for a brief time, not drinking water, nothing too serious. But, you know, I definitely could see the toll that I was taking on my body. At some point I was pretty underweight, I'd say, about 3 years into the company. So you definitely don't want to— you don't want to go that route. You want to stay healthy throughout the way.

Like you want to protect your temple, make sure that you're hydrated as you are being wildly audacious. I think it's— and meditate and stay centered. I think that's for all of us. I'm building right now and I'm like, it's more work than any job that I've had. So I think this is really a message at some point. So everybody can find, find you online at Leilani Social. So Leilani is L-E-I-L-A-N-I, Leilani Social. And then we'll stay in touch. Thank you so, so, so much.