Andrea LaRosa’s Stories, Lessons & Insights

Andrea LaRosa shared their story and experiences with us recently and you can find our conversation below.

Andrea, so good to connect and we’re excited to share your story and insights with our audience. There’s a ton to learn from your story, but let’s start with a warm up before we get into the heart of the interview. What is a normal day like for you right now?
Right now, I’m in a major transition—and honestly, it’s an exciting one. I’m in the process of selling my matchmaking business so I can focus full-time on hosting my podcast Date Smarter. Sexier. and marketing my second book. It’s a big shift, but it feels like exactly where I’m supposed to be.

I usually start my mornings with mushroom coffee and a workout—either a run or weight training. Taking care of my body and my mind is a huge priority. Once I’ve gotten that in, the rest of the day is a mix of podcast production (recording episodes, meeting with guests, connecting with listeners and brands), consulting with clients, and marketing the book.

I also consult with small businesses to help them grow and communicate more effectively, which ties in perfectly with my background. This will actually be the third business I’ve built and sold, so at this point, I’ve got a real soft spot for helping other entrepreneurs get where they want to go—without burning out or losing the passion.

No two days look exactly the same, but they’re all packed with purpose. I’m building what’s next, and I’m loving the freedom and creativity this chapter is bringing.

Can you briefly introduce yourself and share what makes you or your brand unique?
I’m Andrea LaRosa—author, podcast host, communication coach, and a three-time entrepreneur with a deep obsession for helping people connect better, in every sense of the word. I spent years running a successful matchmaking company before shifting my focus to what I’ve found truly moves the needle in relationships and business: communication.

I’m currently kicking off the sixth season of my podcast Date Smarter. Sexier.—a show that’s part real talk, part expert advice, and always unfiltered. I also work with individuals and businesses to improve how they show up in conversations that matter, whether it’s a first date or a high-stakes client meeting. I just finished writing my second book and am in the thick of marketing it, while also wrapping up the sale of my third business.

At the core of everything I do is the belief that better communication leads to better lives. I’ve seen how learning to express yourself clearly—and actually listen—can transform everything: relationships, confidence, business success, and even the way you show up for yourself. That’s what keeps me going. I’m passionate about helping people communicate with more clarity, connection, and courage—whether that’s on a date, in the boardroom, or just in their everyday lives.

I’m also deeply committed to giving back and supporting my local community. Whether it’s mentoring new entrepreneurs, consulting with small business owners, or offering free education through the podcast, I care about making these tools accessible. I’ve been through my own pivots, reinventions, and rebuilds, and I know how important it is to have someone in your corner. If I can help someone feel more seen, more confident, and more capable of creating the life they want—that’s the real win.

Amazing, so let’s take a moment to go back in time. What relationship most shaped how you see yourself?
Hands down, it’s my current relationship with my partner. For years, I was teaching clients how to attract the kind of love they truly deserved—how to stop settling, how to communicate their needs, how to choose someone who could actually meet them. I was out there helping people build healthy, lasting relationships… and meanwhile, I wasn’t fully taking my own advice.

I spent a long time in and out of relationships with men who, quite frankly, couldn’t handle someone as driven and ambitious as me. But to be fair, I wasn’t exactly showing up for them either—not in the way I thought I was. I was so used to being the one who knew better, the one who had the tools, the one who could do the emotional heavy lifting. I had this subconscious belief that, because I was a coach and a matchmaker, the responsibility to “make it work” was always mine.

This relationship shifted all of that. My partner has shown me what it looks like to be supported equally. He shows up for me in ways I didn’t even realize I needed—and he does it without being asked. We have each other’s backs. We communicate, we grow, we mess up and own it. It’s real, and it’s mutual.

He’s reminded me that being strong and independent doesn’t mean doing it all alone. That I don’t have to over-function to be loved. And that the kind of relationship I spent years helping others find? I was allowed to have that too.

Was there ever a time you almost gave up?
Almost every day—no joke. Being a business owner isn’t for the faint of heart. It looks glamorous from the outside, but the reality is that it ebbs and flows constantly. One day you feel like a genius, the next you’re wondering why you thought this was a good idea in the first place. And unlike having a traditional 9–5, there’s no safety net. All of the responsibility, the decisions, the client wins and the losses—they fall squarely on your shoulders.

There have been plenty of moments when I questioned whether it was worth it. When launches flopped, or people didn’t show up, or I felt like I was pouring my heart into something and getting silence in return. It’s exhausting. It’s lonely. And sometimes, it just straight-up sucks.

But here’s what I always come back to: I didn’t build my businesses because it was easy—I built them because I knew I had something valuable to offer. Because I believe in helping people communicate better, love better, live better. And that mission is what pulls me through the hard days. That, and knowing that I’ve made it through the messy middle before—and I will again.

So yes, I’ve almost given up more times than I can count. But I’ve never actually quit. And that, to me, is what makes all the difference.

I think our readers would appreciate hearing more about your values and what you think matters in life and career, etc. So our next question is along those lines. Where are smart people getting it totally wrong today?
Honestly? In how they approach relationships. Too many smart, driven people are dating like it’s a box-checking exercise—chasing a curated list of qualities instead of focusing on what actually creates a lasting, supportive, real relationship.

We’ve become obsessed with the idea of “not settling,” but most people have that concept completely backwards. They think “settling” means choosing someone who doesn’t hit every bullet point on their wish list—when in reality, the real settling is staying stuck in shallow relationships with people who look good on paper but can’t show up emotionally. Settling is ignoring the red flags because the package looks shiny. It’s prioritizing chemistry over compatibility and wondering why nothing sticks.

Attraction and ambition matter, sure. But so do communication, emotional availability, kindness, and the ability to handle conflict like an adult. Smart people often miss that part. They focus so much on aesthetics or status that they overlook whether this person will actually feel good to share a life with when things aren’t picture-perfect.

Dating isn’t about optimizing your chances like a business deal. It’s about connection, alignment, and trust. When you lead with that, everything changes.

Okay, so let’s keep going with one more question that means a lot to us: If you retired tomorrow, what would your customers miss most?
Honestly? The straight talk. I’m the one people come to when they’re tired of sugarcoated advice and just want someone to tell them the truth—with compassion, but without the fluff. Whether it’s dating, relationships, or communication struggles, I’m known for being the person who will lovingly call you out, help you see your blind spots, and then hand you the tools to do something about it.

Even when I’m not “on the clock,” I’m always dishing out unsolicited dating advice—and somehow, people keep coming back for more. I think it’s because I make tough conversations feel easier. I create a space where people can get real, be vulnerable, and actually feel understood. And I genuinely care. I want people to thrive, not just survive their relationships.

If I disappeared tomorrow, I think people would miss that mix of warmth and realness. The voice that says, “Yes, it’s hard—but you can handle this.” And the reminder that better communication really can change your life.

Contact Info:

• Website: https://www.datesmartersexier.com/
• Instagram: https://www.instagram.com/stories/datesmartercoach/
• Linkedin: https://www.linkedin.com/in/andrealarosacoach/
• Facebook: https://www.facebook.com/datesmartercoach
• Youtube: https://www.youtube.com/@datesmarter
• Other: https://www.tiktok.com/@datesmarter