Learning as You Go: Intuition, Mentors & Entrepreneurship | Maggie Williams

What if you didn't have to have everything figured out before taking the next step?

In this episode of Court-side Conversations, Courtney Headley sits down with entrepreneur and commercial real estate professional Maggie Williams to explore what she's learned from building an unconventional career, investing in opportunities before she felt completely ready, and navigating entrepreneurship one step at a time.

Maggie shares why she believes the best opportunities often come from learning as you go, trusting your intuition when things don't feel right, and surrounding yourself with people who can help you grow instead of trying to have all the answers yourself.

Together they discuss:

• Why taking action often matters more than having the perfect plan
• The career lesson behind "Who, Not How"
• How mentors and masterminds can accelerate your growth
• Learning to trust your intuition when self-doubt shows up
• Why optimism can be a competitive advantage in entrepreneurship

If you've ever felt like you needed to have everything figured out before moving forward, this conversation will remind you that confidence is often built by taking the next step...not by waiting for certainty.

Pull up a chair, grab a drink, and join us Court-side.

Connect with Courtney
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🎙️ YouTube: www.youtube.com/@CourtneyHeadleyOfficial

About the Podcast

Court-side Conversations is a podcast about leadership, self-trust, and the moments that shape us.

Each episode features a candid conversation with remarkable women about the experiences that helped them trust themselves, navigate challenges, and move forward with confidence and integrity.

Hosted by Courtney Headley, founder of Center Court Collective.

New episodes released every other week. 

Transcript

Why I'd Rather Take More Risks

SPEAKER_01 0:00

I've learned for me, I would much rather take more risks and have it be a little more exciting than stick with one thing that's safe if I'm if I'm not interested in it.

SPEAKER_00 0:12

Hi, and welcome to Courtside Conversations. This episode is for the woman who's realizing who she surrounds herself with is more important than knowing everything. I hope you enjoy. Today I am joined by Maggie Williams. And to me, when I think of Maggie, I think of like boss lady. And so I admire Maggie for knowing what she wants and going after it. And so, Maggie, I am so excited to have you here and learn from you. Thank you so much for joining me.

SPEAKER_01 0:51

Yeah, thanks for having me. Excited to be here. I love what you're doing. Thank you.

SPEAKER_00 0:57

Okay, Maggie, can you tell us a little bit about yourself?

SPEAKER_01 1:02

Yeah. So currently living in Austin, Texas with my husband of a little over a year, so still kind of newlyweds. And our two fur babies, Teddy and Chai. And um so yeah, a little bit about myself. Um, have been in some sort, some form of real estate most of my career in terms of work. Um, have worn a lot of different hats, done a lot of different roles, but always somehow relating to real estate. I love to travel, I have a twin sister. Yeah, life's good.

SPEAKER_00 1:38

Everything's pretty good right now. Okay, and then Maggie, I always ask people, how do you and I know each other? We are cousins.

SPEAKER_01 1:47

Yeah. Dan, my stepdad, and your mom, Chris, are siblings. That's so love that.

SPEAKER_00 1:54

I remember growing up always like looking up to you and Kate. Oh, so cute. So cool. That's really cute. So fun. And then what are you drinking today?

SPEAKER_01 2:06

I'm drinking a bae. This is like my favorite just every day. I probably go through like three of these a day, and it's not sparkling, which is hard to find.

SPEAKER_00 2:16

Like it's flat, but they're so good. So I also am drinking water, but I prefer sparkling water. So I've got just uh sparkling grapefruit water. So all right, Maggie, before we start, cheers. Thank you so much for joining me. Thank you for having me. Okay. And so

From Bartending to Boutique Hotels

SPEAKER_00 2:35

I know you told us a little bit about your background in real estate, but could you share a little bit more? You said you've worn many different hats. Can you kind of walk us through your career journey?

SPEAKER_01 2:44

Yeah, absolutely. Um, so after college, I wanted to be in fashion, I thought. And I got a job at Guest at their headquarters, downtown LA. And I was super excited. Um, but I was there probably, I think, three months before I just was like, unfortunately, my boss was gone all the time, and he never left me anything to do. And I was just bored out of my mind. And going from college to that was just such a shock to the system. So yeah, I only lasted three months and I ended up quitting and getting a job bartending. From there, I kind of actually fell into real estate. Uh, when I was working at the bar, the guy who lived next door to the bar owned a mortgage company and uh ended up just bringing me on board. He had lost his main processor and basically just threw me into it. Like, here's a manila folder with a credit report inside. Go turn this into a deal. And I knew nothing. So learned really by just getting thrown into it, but it was the best way to learn, honestly. So yeah, did that for a few years. Then I switched to commercial lending and loved that. From there, I moved to New York. I did residential real estate in New York. Um, and then I moved to Austin three years later and have had a variety of gigs out here. I worked for a multifamily syndicator, um, worked for a glamping developer. Um I've worn a lot of hats, but looking back, it might look like I've jumped around a lot, but it's it all kind of put together a more holistic view, I think, of real estate for me. And so now I went back to commercial lending. Um, but in between that, uh own and manage some Airbnbs. And then my husband and I bought a boutique hotel a few years ago and renovated that, and I managed that from afar. And that's been really fun. Um a big learning curve, but really fun and and kind of the direction I hope to see myself going in. I would love to do another one now.

SPEAKER_00 4:55

So and we're yeah, Miami, like that's in Palm Springs, right?

SPEAKER_01 5:00

Yes. So the the hotel's called the Muse, and it's in Palm Springs, and it's a cute little 1960s hotel. It's got nine rooms, it sleeps 22. Yeah, it's been it's been fun. I want to get out there and and check it out sometime. And I highly recommend it.

SPEAKER_00 5:17

Okay, and that's where you're where you hope to go in the future.

SPEAKER_01 5:21

Yeah, and you know, it's funny because I I left um a job that I was doing that was very comfortable in Austin, but I just got bored. Honestly, I got really bored after a few years. I was sourcing deals, but I wasn't doing much else. Nothing analytical, nothing creative. And, you know, people were like, What? Why are you leaving? You have such a cushion job. At the time, I was like, is this crazy? Am I crazy for leaving this? But I've learned for me, like I would much rather take more risks and have it be a little more exciting than stick with one thing that's safe per se if I'm if I'm not interested in it.

SPEAKER_00 6:03

So if someone

The Messy Part No One Sees

SPEAKER_00 6:04

were to look at your career and like they see you've done all these different things, worn different hats, what would they not see?

SPEAKER_01 6:13

Oh gosh, how messy it is, how messy it can be in between. Um yeah, you know, it's interesting because when I look back at how I started in real estate, the first property I bought by myself in Austin was under construction and it was in an area that I could see was really going to explode. So I just knew this is going to be an amazing opportunity. So I needed, I think the minimum you could put down was 5%. But I didn't even have that. I borrowed from my dad just to make the deposit. And that gave me enough time because it was still a year out before when we would actually get the loan and um it would be built, and I actually had to finance it. Um, but yeah, I I borrowed half of that down payment and ended up being able to pay him back within the year. I think I bought it for five ABD and whatever. Say it went to one one in the next few years. So from there, I was able to pull cash out as a cash out refi and buy my next project and then another. But you know, people don't see like I didn't start with anything really, and I was able to kind of grow it. You don't need a lot to start if you're finding the right opportunities. It's harder now because real estate has exploded so much, but uh, there's opportunities everywhere. You just gotta be creative. Yeah.

SPEAKER_00 7:43

Yeah. So I love sort of the, you know, the for lack of a better metaphor, like the glass is half full. Some spectral. Yeah. All the opportunity because I don't often hear that. So it's really refreshing.

SPEAKER_01 7:55

It is. And I mean, it is hard to stay that way because we're just inundated with bad news and you know, things that can go wrong. A lot of times I'm uh too positive and not looking at all the negatives. But, you know, being an entrepreneur, you kind of have to have that outlook or you would never do anything because there's so many risks involved with being an entrepreneur and building things. And I think if you don't have somewhat of a glass half full, you won't, you won't ever take that leap.

SPEAKER_00 8:29

Yeah, you won't take the leap. Yeah, exactly. I love that. Okay, Maggie, can you tell me about a time at work where you either felt like you truly belonged or a time when you realized you did not belong?

SPEAKER_01 8:42

Oh, um well, I would say commercial real estate has generally been uh kind of an old, old boys' club. Especially when I first started in commercial real estate, had a great boss, but it was really kind of an old boys' club. And especially because I was in Texas and working with men like twice my age who had a ton of experience. And a lot of times when they would get me on the phone, they'd be like, Can I just talk to your boss thinking I'm the secretary or something? So I would have to kind of like blow them away with like my knowledge and just be very straightforward and kind of like, no, I'm the analyst and you're talking to me. And usually very quickly, they'd be like, Oh, wow, she really knows what she's talking about. That was tough in the beginning, especially I was still in my 20s. You're still kind of figuring things out. So having to just put yourself out there and, you know, learn as you go, but also, you know, not apologize for what you don't. So I would say didn't initially feel like that was my crowd. I think, you know, as women, like it's hard to keep that balance between being assertive and knowing what you bring to the table without you know being called a bitch or something. That's a challenging um line to walk, I think.

SPEAKER_00 10:09

Yeah, it is it is unfortunate though that like we are having to like temper ourselves so that we aren't perceived as a bitch, but also say enough that they're like, oh, you know what you're talking about. Okay. Can

The Career Advice That Changed Everything

SPEAKER_00 10:23

you tell me about either the best or worst career advice you've ever received and how it's shaped you today?

SPEAKER_01 10:31

You know, something I'm still always learning, but I think in the last five years, I've really learned a lot more is they say who, not how. But, you know, if you find mentors or the people who have done what you're trying to do and just get around them, you don't have to know everything yourself. Quite oftentimes, the most successful person is not the one who knows everything, but the one who knows everyone and who to put in the right roles and to surround themselves with the right people. I've started going to a lot of these masterminds. I'm a part of a boutique hotel owner's mastermind, and I was part of an Airbnb manager's mastermind. And it's not just like what you learn at them, but the people you meet and then the relationships that carry forward and then the deals you might make with those people. So just being in the right rooms is huge. And it also does carry over to your personal life. Having people around you that challenge you, it make you be better and are interested in things that you're interested in and elevate you as a person, it's the who, not the how. Yeah. I love it.

SPEAKER_00 11:45

Okay, and so Maggie, knowing

Learning to Trust My Intuition

SPEAKER_00 11:47

that you index towards positivity, is there a time throughout your career in your life when like you have had self-doubt? Yes.

SPEAKER_01 11:54

Every time I jump to some new opportunity, I'm like, oh my God, what did I just do? When I left that pretty Kush steady job, I probably jumped the gun a little too soon. There was one job that made me leave that Kush job. It was a startup with a multifamily syndicator. Two women owned the company. They were great. Um, I was so excited about that role. And I was wearing a lot of different hats. They had hired me to be an analyst, but then I ended up doing the business development and the acquisitions and the underwriting and negotiating all the contracts. And I was wearing myself so thin. And during this time, I realized some things that were happening, not only in the market, but with deals that they had done. They were basically just um not underwriting in a way I would. If one little thing went wrong, I could see like all these investors are gonna lose their money. And it became super, super stressful. And I was new to the company, but I saw what was happening. And at the time they didn't really believe me. Or they were like, you know, I don't know if you're right. So I ended up leaving, and that was really devastating because at the time I was really doubting myself. Like, am I being too uh cautious here? It just felt like a failure because I was so excited about that gig. So I think, you know, what comes out of that is like trusting my intuition a lot more. I learned a lot, actually. Um, and it wasn't that I was a failure. There were other things happening, you know, beyond my controls. That feeling comes up all the time when you're entrepreneurship. There's no guide and you're just guessing as you go along. There's not a right decision always. There's different decisions and you they'll take you different ways, but there's not just one right answer. So that's right. Realizing that I think helps.

SPEAKER_00 13:46

Yeah. Yeah. And to your point around trusting your intuition, it's almost like just trust yourself just to take like the next step and then just see what happens, right? And then you can continue to pivot, just yeah, move and see.

SPEAKER_01 14:00

See what and I think when you are pushing against your own intuition is when it falls apart most. But if you kind of relax into it and let things happen, the universe kind of brings you what you need.

SPEAKER_00 14:15

So the next time your inner critic shows up for you, what do you think you'll do differently to just move forward?

SPEAKER_01 14:22

I was in a mindset uh mastermind, I guess, recently. I wouldn't say I'm like super woo-woo, but there are a lot of uh skills that that were new to me and stuff that I learned in that that I really think are super helpful, like positive affirmations and visualizing things going correctly and how you want prior. I've gotten more into that. Um I really do think when you put yourself in the right energy, you're so much more likely to succeed and attract the right people. And it's just changing your energy. Now that's the only difference, but it's huge. The reaction of that energy really matters. So I'm much more conscious of that now. I I would like to say I do it every day. I don't, but I try to at least uh reflect on that more. Do those affirmations and visualize it going the way I want. Yeah. Yeah. And like also just not taking things so personally, you know, that's a big one. That's so hard.

SPEAKER_00 15:31

Like I feel like, especially as women, if something doesn't work out the way we hoped, we make it mean something about us. Yeah. I agree. Okay, I love it. Okay, and then Maggie, if you were starting your career today, knowing what you now know, what, if anything, would you do differently? Oh God, buy a lot more real estate back in 2000.

SPEAKER_01 15:53

Yeah. Um gosh, of course, yes. But I think I would have found mentors earlier on and really like not being afraid not to know everything, but just finding the right person who does and learning from them and asking questions and being a fly on the wall or just getting in the right rooms, you know. I don't think I realized how important that was until much later in my career. Yeah.

Lightning Round

SPEAKER_00 16:20

Okay. Are you up for like a fun lightning round? Sure. Okay. So my rules are just first thing that comes to your mind, there is no right or wrong answer. Try not to overthink it. And all the questions are gonna be work related. So okay, just no that. Um, okay. Do you prefer to do business in person or virtual? Um in person. It's more fun. Um, okay. Least favorite office jargon.

SPEAKER_01 16:49

You know, the one I hate, but I use. I hope this email finds you well. It's like, yeah. I don't know why I use that. It's so annoying, but I it's just like you gotta say something nice before you just barrel into what you need. Biggest workplace pet peeve. Like loud crunching while eating, you know, when someone's eating and and they're working and they've got all their food all over.

SPEAKER_00 17:12

If you came with a warning label, what would it say?

SPEAKER_01 17:17

Probably something about the battery. Turn it off, like because I'll run out of battery. I'll just like keep going and going and then run myself ragged.

SPEAKER_00 17:27

If little Maggie were to see you now, what do you think she would say?

SPEAKER_01 17:31

I think actually she'd be excited, impressed. I don't regret my uh path at all of that.

SPEAKER_00 17:39

Well, Maggie, I so, so appreciate you joining me today. I have learned so much. One thing I'm taking away from you is it's all about the who, not the how, and surrounding yourself with people that inspire you and make you want to do more and be better and challenge you. I think that's really important. I asked my guests, do you have a favorite toast or just a toast that you would like to close this pod with?

SPEAKER_01 18:06

Oh, I wish I had something clever.

Cheers to Women

SPEAKER_01 18:09

Um, cheers to women.

SPEAKER_00 18:11

Yeah, they're here. Cheers to us, ladies.

SPEAKER_01 18:14

Thank you, ladies. I like it.

SPEAKER_00 18:17

I appreciate you. Yeah. Thank you. Okay, listeners, thank you so much for tuning in. If any of this conversation with Maggie resonated with you, please do share this episode with a woman that you love. And if you and I are not yet connected on LinkedIn, please come find me and say hi. I'd love to chat. And until next time, I'll see you courtside. Cheers, y'all. Thank you.