Jessie Dillon

Get ready for an exciting episode as we dive into the incredible journey of Jessie Dillon – a powerhouse in the real estate and beauty industries. Join us as Jessie shares her inspiring story of overcoming obstacles, taking risks, and building a successful empire that’s all about helping people achieve their dreams of feeling beautiful and retiring early.

Whether you’re an aspiring entrepreneur or simply looking for motivation to pursue your passions, this episode is for you! So tune in and get ready to be inspired by Jessie’s infectious enthusiasm and unwavering determination to make a difference in people’s lives. Trust us! You won’t want to miss it!

In this episode, we cover a range of fascinating topics with the incredible Jessie Dillon, including:

  • What inspired Jessie’s journey toward becoming a successful real estate investor and beauty industry leader, and how did she achieve semi-retirement?
  • What pivotal experiences led Jessie to explore the beauty industry and real estate, and how she navigated each transition?
  • Jessie’s battle with anxiety – how she learned to overcome it and invest in herself with the help of a coach.
  • The exciting story of Jessie’s very first real estate deal and the valuable lessons she learned along the way.
  • Jessie’s best pieces of advice gleaned from her years of experience in both the beauty and finance industries for aspiring entrepreneurs?
  • Based on all she’s learned along her journey, what Jessie’s current self would tell her younger self.

Sneak peek into what’s on the horizon for Jessie’s world in the next six to twelve months.

Join us for this illuminating and inspiring conversation with Jessie Dillon, and discover the secrets to her success in real estate and beauty! Listen to the full episode here:

Connect with Jessie here:

Click To Read The Transcript

Jessie Dillon Shares Her Journey to Semi-Retirement through Beauty and Real Estate

Kevin Harrington
Hi, I’m Kevin Harrington, an original shark from the hit television show Shark Tank and you’re listening to the underdog podcast

Pamela Bardhi
Hello, everyone, and welcome to the underdog Podcast. Today I have an incredible guest here with me, Jessie, how are you?

Jessie Dillon
I’m very good. How are you?

Pamela Bardhi
I am awesome. We were just saying, you know, move for this call and how much I ignored your energy. You know, we met at a meetup that I was speaking at. And I was like, Hey, can you send me your story and I was like, Holy crap.

I’m like, this girl’s gotta get on the podcast. We got to talk about it. because you’ve done some amazing things. And you’re headed in like this crazy, amazing elevation. So I’m so excited to have you here today and share your story.

Jessie Dillon
Yeah, I’m happy to be here. I really love sharing because I feel like I’m at a point that’s still very relatable to people. who are just trying to get that first deal. I know that when I listen to podcasts where people are talking about 1000 units syndications and stuff.

That’s not really relatable to me. So it’s not that inspiring. But I feel like what I’m doing is still at a level where, like, if you’re just trying to break through. it just feels so doable. And I think that’s going to inspire people to take action for sure.

Pamela Bardhi
Absolutely. Desi, absolutely. So what inspired you on your journey to where you are today. and I know it’s been a long road. what inspired you a little backstory

Jessie Dillon
for anyone who doesn’t know me, I’m 31 years old. I live in Central Massachusetts. I’m a wife, a mom, I own two businesses. I’m semi-retired in terms of real estate. I have five units, which are valued at around 1.5 million. What inspired me to get into real estate is just, I don’t wish to trade time for money for much longer.

In fact, I want to get out of doing that as soon as possible. And the work that I do in my beauty business, which is what got me into entrepreneurship. starting my beauty business about five or six years ago. The work that I do in that business is definitely more physical work.

And I started to have a lot of physical health problems with my neck, my wrists, my back. and I was like, I definitely can’t do this forever. There’s gotta be some way out. There’s got to be a backup plan, or a next phase of this. where I don’t have to do this physical work.

First, I discovered this whole fire thing through like a Facebook clickbait article is how I discovered it. And the girl that was featured in the article. I messaged her on Instagram and was like, here’s my situation. If you were going to recommend one book to me, what would it be?

And she recommended The Simple Path to Wealth. I’ve read it, I loved it, I was like, I can do this. I have a really high savings rate. I’m going to dump everything in index funds and retire early. but it was still gonna take me 11 years. So I was like, Oh my God, that’s like a gut wrenching reality to think I have to do this for 11 years.

like still going hard, still just torturing my body. and forking over half my income every month for 11 years. So I’m like, There’s got to be another way. on one of the fire podcasts, there was a real estate investor. And he said, you can easily do this in two years.

paid off your regular income while you’re trading time for money and swap it for investment property income. So in two years, I can totally do that. I’ll do anything for two years to get that end result of not having to trade time for money anymore. So that’s kind of that springboard for me is hearing that on that podcast.

Pamela Bardhi
That’s amazing. Like, what’s so cool these days is like podcasts. and just all of this knowledge that never existed before. You know what I mean? Like I remember, I wish I had seen a clickbait ad. that had something to do with this when I was in high school.

And it changed my whole trajectory. But I didn’t learn until much later. So it’s so funny how like the way that knowledge has been spreading almost. like YouTube could be more valuable than I could call it education sometimes.

which is so nuts to like, think about Sonos. and think about like, just I wouldn’t really go all the way back to with you back to almost like childhood. Like what did you want to be when you grew up? Like what was like your dream?

Jessie Dillon
Oh my god, I have no idea. I never saw past the age of 20. When I was in middle school, junior high high school. I just couldn’t even fathom that there was life after school. And I think a lot of kids feel that way. Right? Like you just can’t even picture it. You just hope that your life is good or easy.

So or you can see your parents and see like. I do want what they’re doing or I don’t want what they’re doing. And my parents have always worked super hard like especially my dad. he always worked super, super long hours overnight to provide for our family. which is amazing.

But I didn’t see him quite as much as I would have wanted to. And I just knew that I never wanted to be someone. who had to go to work nine to five or more and do that until I’m 65. I was never a hard working person. And I thought that was like a huge flaw in me, like.

in all of the hourly jobs that I had up until I really found my passion in the beauty industry. In all of these dead and merrily jobs. I was a really bad employee. And I thought like it was just me. and that I just am a bad employee. I was lazy, and just didn’t respect the whole process at each place of work.

But it was just that I didn’t find my passion. and that my passion definitely was not working for someone else. High school was tough, I was dealing with really bad anxiety. So I actually missed a lot of my senior year and almost didn’t graduate on time. And that definitely didn’t set me up for success.

I took a gap year and didn’t know that I was going to lose all those scholarships. if I took a gap year because I did get great academic scholarships. So after high school, it was kind of I tried out college. I went for one semester.

but I had to work full time at the same time, and it was just too much. And it was a lot of just one menial job to the next. until I found the beauty industry and really love it. So it just took me a long time, I felt like finding my footing.

Pamela Bardhi
And that’s totally okay. Because like, look at where you’re at now. It’s amazing. Well, when you mentioned being a bad employee. like I was probably the worst as well. Like I literally I was always overthinking. I was always overdoing it, I was always like. Well, why do I have to do this? Why don’t we just do this process? Instead? It’s gonna be faster for you.

And like the owners are like, can you just lik. do what you’re told? To do? And I’m just like, Oh, my God. This is like a waste of my life. What do I do, you know, like, through like, like college jobs and stuff. it’d be like random stuff like that. So I can definitely resonate with that.

Thank you so much for sharing that about anxiety. because there are so many people that are struggling with that at this current point in time. like all around the world. I mean, thank God more people are talking about it. But Jesse, how was that one way that you helped kind of mitigate that?

Because then you almost didn’t graduate because of that. And then look at you now fast forward now. I mean, it’s obviously a work in progress. And it’s a day by day thing. What was something that helped you in that journey?

Jessie Dillon
Yeah, I mean, I definitely won’t try to say that my anxiety is gone. because that’s absolutely not true. But I was watching a Netflix documentary that said that 30% of people deal with some type of anxiety. or anxiety disorder, right. And I’m like, Damn, that’s quite a bit like, I know. We talked about it a lot.

But I feel like that statistic is even higher than I would have expected. I think doing a lot of mindset work has been the most impactful for me when dealing with anxiety. And as someone who’s fully self employed, I have no paycheck to rely on. That definitely caused more anxiety for me at the beginning.

I’m fortunate that my husband was so supportive and still is so supportive in every way. And that helped. But you know, I do still experience some anxiety with my businesses. but not quite as much as you would think. I think doing the mindset work. whether you have anxiety or not. is really the only way to survive self employment.

then it sounds so corny. but my mom had always told me you should try yoga for your anxiety. And I’m like, That’s so stupid. That doesn’t do anything. And a year ago, I finally tried it and had to admit to her that yes. It does make a big difference. But yeah, I think just mindset work and yoga actually have been really helpful for me with anxiety.

Pamela Bardhi
That’s amazing. And like when it comes to yoga. I think one of the reasons for that is because emotions get trapped in areas of our body. and with yoga, you release. So it makes sense that it would almost like to release certain emotions.

and certain things you kind of feel almost instantly better. And the mindset that you talked about. like what has been like. because there’s always quotes and mantras. Like what has been one that has always stuck with you. One big

Jessie Dillon
one is like, everything is always unfolding in my favour. Nothing is ever happening to me. It’s only ever happening for me. And just the whole you know, the universe has your back type thing. I’m not a religious person. but I really do believe that like there is this greater system going on that plays chess pieces.

you know what I mean? And like, just everything’s always going to be fine. I can worry until I’m blue in the face and it’s not going to change anything. For anyone else who’s struggling with mindset issues, too. I really love manifestation babe.

My name is Catherine’s and kina. she’s a mindset coach that one of my clients is excellent at. and introduced me to when I was starting my own business. And I really feel like getting into her work at that time is like a huge part of my success.

Pamela Bardhi
Amazing. That’s amazing. Oh my god. Jesse, I love that. I mean, it’s just, it’s so cool to hear. like all the different thing. but one of the biggest things that you said, I’m not religious. but I’m super spiritual, right? So understanding like the universe is always conspiring in your favour.

And whether or not you want to attract negative thoughts to x. If you think negatively, you’re gonna you know, the universe like, Oh, crap, well. she’s saying this, or she must want this and then it just attracts more. It’s like your mind is touching. Grazie tool, and you gotta know how to use it.

Because you could, it depends what energy comes to you. But the universe is definitely always conspiring in your favour. And like you said, it’s working for you and not against you. I love that. So like, walk me through how you got into the beauty business initially.

Jessie Dillon
So you know, as I said, I was working all these like dead end jobs that I gave up on in college. that wasn’t for me at that time. I do think it could be for me in the future. But you know, it wasn’t for me at that time. I was working these seven jobs. And my best friend actually went through beauty school.

I was like, you know, I think I could be into that. I always was like, messing with my own hair and colouring it and cutting in. And I’m like, you know, I could be into that for sure. So I went to an adult programme that was a year long at night. I was working at Sally Beauty Supply during the day, and then went into school at night.

And I was making like 750, at Sally’s. I vividly remember, I was working full time. and I couldn’t even pay for my car insurance. And I was just like, I’m out of the house from 7am to 11pm going to work and then school. I can’t even pay my own car insurance. like my parents had to come in and rescue me with that.

So after that, I was like, I’m so over this hourly thing. like I could do so much better if I just have control over my success. like, these people don’t care about my success. They don’t care about my car insurance, you know what I mean? No one’s ever gonna care about it as much as me. So they should not be in the driver’s seat.

They are my bosses at these places. But anyhow, I went through Beauty School. you go to Beauty School, and generally the plan is you’re going to be a hairdresser. Immediately. I was like, I don’t want to do hair. But I had borrowed the money to go to school from a family member.

So I was like, I have to finish, I have to get the licence at least I got out of school. And I’m like, Alright, I don’t want to do hair. So what can I do with this. I got a job at a big box beauty retailer. And I got it because of my skincare experience in beauty school. they were really trying to drive education and sales to skincare.

So I got a role as kind of like the in store trainer. So I would train everyone on skincare stuff, new products. And I stayed in that position, going to a larger store. moving around different supervisory roles for about five years. And I really, really loved it. I loved what I did at work every day.

Of course, there were some downsides because ultimately. you’re a manager at the mall. So there’s still all the bad things that come with that, like this schedule. And I was like shooting for the stars with that company. I was like, I want my own store. I want to just keep growing and growing and growing. And all these promotions kept coming up.

They were ones that I was a perfect fit for. I thought and I was doing all the work, I was going above and beyond. I was doing all the extra projects, meeting all the metrics. And after I didn’t get the third one, I was like something’s going on here. And ultimately, the supervisor above my supervisor above my supervisor. you know what I mean?

Like three people up the ladder from me. told me that my voice makes me hard to read. And that’s why I wasn’t getting promoted. So from that moment, I was like, I gotta get out of here. There’s nothing I could do about my voice. obviously, I just gotta go. So I started kind of making my backup plan.

I’m like, Oh, wait, I have this Cosmo licence that I haven’t been using for five years. So I took a class on lash extensions. And I started doing those one day a week. So now I’m working six days a week. Then I took a class on microblading. And I started doing that another day a week.

So now I’m working seven days a week. but I’m feeling amazing because I’m building my own safety net. I’m making my backup plan. my escape plan just a couple months after my husband pointed out to me. you know, staying at your full time job is costing you money.

like you could be making so much more money in so much less time. If you had time to just take a couple more Microblading clients on your days off. so I’m like Am I really gonna do this insane like psycho person. move and quit my full time job with no real plan?

Yes, I was so I quit that job. I’m like, I can go full time at the salon. that I was doing these things at on the side. I’m like, I can go full time there. So my first week of going full time there, I quit that too. Because I’m like, I don’t love the way this place is being run. It’s not working for me.

So I call my husband and I’m like, I quit this job, too. So now I have no jobs. And he’s like, Okay, this is fine, like, this will be fine. And everything just fell into place, I started taking clients from home. I got an opportunity to rent somewhere a couple of days a week. I got a freelance job for a cosmetics brand to kind of fill the gaps.

And within nine months after that, I was opening my own studio. So it was like just this rocket took off. when I just cleared my plate of all these bosses. all these other people’s schedules and other people’s processes. and could just do my own thing. It was this huge springboard for me.

So I opened my own place. I’ve expanded once I have a team of like around seven people. seven service providers. We offer Permanent Cosmetics as in cosmetic tattooing, lash extensions. all sorts of beauty services, except for hair and nails. Yeah. So that’s how I get from point A to point be

Pamela Bardhi
insane. Oh, my God, just above that. I love that. We’re gonna have to talk about how you scaled that though. Because the entrepreneur, that’s one of the hardest things.So you started your own beauty business. So you were working by yourself for a while.

And then you know, slowly, maybe you brought in one person. and kind of like scaled it up from there walk me through that scaling process. because I know, there’s so many entrepreneurs that are like. this is the worst part of it all. bring in more people bringing employees in that kind of thing.

Jessie Dillon
Yeah, so it was just me. And the space that I had, I could have accommodated a maximum of three other people. So I was like I’m paying rent in this unit. And it’s kind of just the space going two ways. You know, there were two treatment rooms. I was kind of bouncing back and forth between them. doing different services three or four days a week.

So I’m like the other days of the week, it’s a total waste. So I need to at least get a couple people in here just using the space. And if they cover my rent, great. And I also really needed help with some behind the scenes tasks like social media type stuff. just reposting certain stories and engaging with potential clients on social media.

I started looking for somebody to to help me with that three hours a week. very minimal, that made it easy to transition into building my team. because I found somebody who I was actually pretty close with and I have worked with in the past. So I knew that she was amazing.

She came on board to help me with that behind the scenes stuff a couple hours a week. And she’s actually still with me, and she’s more full time now. And she’s fully remote, she moved out to LA. she was probably my first pseudo hire. When I started bringing on additional people in the beauty business.

I started with renters. So I started bringing on people who basically just paid me every month or every week. and they had their designated days in those rooms. And that didn’t really work out for me. because I didn’t feel like I had that much control over the client experience.

It was easy, but it just wasn’t what I imagined. So about a year later we were closed for three months. because of COVID, I found a bigger spot. and I started hiring actual employees. which was a little bit scary. But when you’re hiring commissions. people, they don’t make money unless you make money.

So it’s not like you’re on the hook to pay them if they’re not bringing anything in. but now I’m actually transitioning back to having all renters. now that I understand the business a little bit more and understand. how I can set that up in a way that it would be more suitable for what I want for my brand. You know,

Pamela Bardhi
amazing Jesse. That’s amazing. It’s just so cool to see, like, going from you with no backup plan quitting your two full time jobs. You know, to be like starting this and really expanding it. That is so amazing. Oh my gosh. And then from your beauty business. jumping into real estate, walk me through that journey. Like, how did that happen?

Jessie Dillon
I mean, obviously, when I started my beauty business. I had no freaking idea what I was doing. like, yeah, I was a supervisor at the mall. So that was the extent of my business management experience. but like you had said, you can learn literally anything. from a podcast from YouTube from Google.

Like, there’s no shortage of free information out there. The reason that everyone’s not doing it is. because when it’s free, you’re not really on the hook to actually use it. It’s not like you invested money in learning the information.

So it’s easy to just listen to the podcast that tells you exactly how to do something. and then you just go about your day and forget about it and don’t use it right. And I was like, you know, I’ve already done this once where I had to just be scrappy.

and figure it out myself because if I didn’t, then I don’t buy groceries. like there was failure was not an option. especially because there were a decent amount of people in my life. who didn’t think it was going to work.

So that’s enough for me to be like now I’m going to make it work twice. as hard and like egg on your face. because I’ll do better than you ever thought I possibly could have at my full time job. So I was at a point where I was taking clients four days a week. it was gruelling physical work, you wouldn’t really think so.

But you know, you’re hunched over all day, lots of repetitive movements. So I was like, I was going to physical therapy twice a week. and I was going to cupping once or twice a week. and I was getting a massage every two weeks.

And I was doing the PT exercises at home and like all of the stuff wasn’t helping. So I’m like, you know, I just can’t do this forever. I need to figure out a way to get away from doing this. As much as I love it. It’s just not feasible. So, you know, as I said, I discovered the whole fire thing.

And then someone started talking about real estate investing on one of those podcasts. and about how you can achieve financial freedom so much faster. So I heard about bigger pockets and started listening to the rookie podcast. And this was maybe a year and a half ago. prior to listening to the BP real estate rookie podcast.

And I’m like, wow, I can definitely learn everything I need to know. to get into the first deal from this podcast. It’s not going to be the best deal of my life. But as long as I break even, I’m happy. And I spent probably two or three months just listening to it. And nonstop, every client that I had at work. had to listen to this podcast.

Because I don’t really have a commute. So I’m like, I’ll listen to it all day while I do clients. I invested in the rookie boot camp. which at that point I felt was kind of redundant. I already learned all the stuff from the podcast.

but because I paid for the boot camp and told people I was taking it. that was like an extra kick in the ass. And I invested in some one on one coaching calls with someone. that I had heard on the rookie podcast. like one of their guests, Amelia, I found her on Instagram. but was messaging her and within a couple of months. of even learning what real estate investing was.

and that I didn’t have to be a rich old white guy to do it. I was making offers. And I’m like, This is crazy. I’m using like I’m putting basically like half my life savings on the line here. because I’m in an expensive market. And you know, I can’t get into properties with like, 10 grand as easily.

So yeah, and you know, two months later. I closed on the first one. That was it all happened really fast. But I’m definitely a big fan of just do it messy. and you’ll figure it out. It’s never going to look perfect. You’re never going to find the perfect deal. Like just do it be sloppy, you’ll figure it out as you go. Oh, absolutely.

Pamela Bardhi
I love that. So it’s almost like that coaching almost pushed you into action. Now what was some of the most important things that they said. that helped you kind of feel comfortable and grounded. in like wanting to make a decision that move forward in the first place,

Jessie Dillon
I think I picked the perfect person to invest in coaching with Amelia. because we’re around the same age. she’s a full time investor. She’s based in Iowa. So like, the cost of entry is definitely a lot lower. And you know, the cash flow is lower. but the cost of living is also lower over there.

So it’s easier to achieve that financial freedom by learning from somebody. who I felt was pretty similar to me. like also woman and around the same age as me. I’m like, This is proof. Don’t need to come from real estate. You don’t need your parents to have done real estate.

You don’t need to be wealthy, like you can figure it out. Anyone can do it. And maybe it’s gonna be a little more challenging for some people. like some people get a head start, but I’m like, if she can do it. I can totally do it.

And she just had this unwavering confidence in me. like the way that she talked about real estate investing and still does is just like that. There’s no doubt in your mind that anyone can do something like this. Just no question. Like, it’s so it’s so obvious, like Yeah, of course you can do that.

Pamela Bardhi
That’s so awesome. I’m telling you, those cheerleaders make all the difference in your life, no joke. Like, they literally push you and you’re just like. you know, to see something in yourself that you just ignore sometimes. you know, we always forget about how great software is and what we’re capable of.

And when someone’s kind of almost shining that mirror. It just makes all the difference. That’s so cool. So how did you decide on your first deal? Like how did you run the numbers on the first deal? And walk me through that one a little bit.

Jessie Dillon
So I do really love using the BiggerPockets calculator. but now I’ve actually I like more to physically write it out in like an Excel spreadsheet. because a lot of the deals that I will Looking back now there’s like. you know how it looks today and then how it’s going to look in like
a couple of years when it’s stabilised.

But um, I think I use the BiggerPockets calculator for that first one I was doing. you know, 5% vacancy 5%, cap x 5% repairs. like I was just trying to do it the way that everyone else is doing it. And with this specific deal. I actually knew that I was going to best case scenario breakeven for nine months.

And that was a little bit scary. But at the time, I had such a high income. because I was just busting my ass in my beauty business so hard that I’m like. even if like we have a bad month, we can cover it. we were gonna just barely break even.because there was a long term tenant in the back unit. who was paying less than half of market rent.

and I was in a high interest interest only bridge loan. and I use that product. because then I could put just 10% down because I got it under contract. for so much less than the appraised value. even though it was listed on the market for sale.

You know, it was listed for about 100 days. I went directly to the listing agent. me and my husband and I really built a rapport with her. And when I sent her my offer via email, I included which is so extra now. but like I included all the maths as to like this is really why I can only pay this much.

I really really want this house, my husband’s an electrician. he said the electrical work looks beautiful. like the house is amazing. It’s so well kept. But this is why it has to be this price. So it was listed for 410. It was appraised for 420. And I got it for 357. Wow.

And this was also you know, it was an incredibly competitive time. This was when I got it under contract in November of 2020. So it was a very, very competitive time. I think most people who were looking at it.

They wanted a single family home with an in-law. but because that tenant in the back was on a long term lease. they couldn’t have used it for that. So I think that’s why it was still listed for so long.

Pamela Bardhi
Wow. That’s a crazy deal, though. I mean, you got like what, like walking in with almost 70k in equity.

Jessie Dillon
I know I was very happy about that. And then like six months later. I did a cash out refinance. because the value went up to 450, I pulled out like 11,000. And I got my five year ARM. So the monthly payment went way down. So my cash flow went way up.

Pamela Bardhi
Wow, that’s amazing. And that was the first deal. And then immediately, I think within months you picked up the second one.

Jessie Dillon
Oh, yeah. So the second we closed on that. I’m like, oh, yeah, like, I’m gonna take a rest and take a little break. No, I immediately started. Like I couldn’t resist, I started looking for the next one. I like, I want to short term rental. Now. I want to try this. I think I could do really great with it.

Because I’m amazing with customer service. And I do really feel like Property Management anyway is a customer service business. But with short term rentals. especially I’m like I would kill it with hospitality. Like I already have to do that day in and day out. So February of 2022. I started looking and I got under contract in April.

But then we fell out of contract. because there was so much wrong with the inspection. and we just couldn’t come to an agreement. I was totally bummed out that I spent like 1500 bucks on inspections. but we had to just throw in the towel with that one. And then two days later. I got under contract for something way better.

which is the one that I do have now it’s up by Lake Winnipesaukee in New Hampshire. it’s a single family home. Yeah, it’s super cute. And it’s nice that we also get to use it sometimes. like getting to share that house with friends and family is really cool.

It’s definitely been a very interesting journey. learning how to set up all the systems. and everything to run a short term rental. without having to do a lot of work every day. I will say I don’t super love the seasonality of this specific area for short term rentals.

So I’m looking into right now, possibly trying to find someone. to do like a corporate lease and then they can go ahead. and use it as a vacation rental if they want. So that’s kind of what I’m dabbling with right now. I fell victim to like short term rentals are sexy. But I realised now I’m glad I had the experience. because I it made me realise I do just really love the totally unsexy long term rental.

Pamela Bardhi
I love that. Oh my god lessons everywhere when it comes to these things, right. And I mean, like, you know, everyone’s trying to find different niches. especially in the real estate space all the time. All different types of new investments are coming out. and short term rental sounds really great. but it has its caveats.

So I’m a big fan of medium term rentals. Those are my favourite because you’ve got those work best. and transient areas, metropolitan areas, downtown areas. and stuff like that where there’s hospitals or schools. where there’s plenty of people coming for a short amount of time.

You know, the minimum 30 days a day. and then kind of expand out Boston’s a huge market for that. So that’s why I’m the biggest fan ever. And plus, we bypass STR laws, too. so MTR, I call them mtrs are so freakin great. So, right. Oh, man, I love that. Jesse, question for you like.

what would be your best piece of advice for anybody. who’s looking to jump into real estate and really go full throttle. because what I find amazing about you is. you’re a business owner. and like you were able to step into this different realm.

and be able to create this financial freedom for yourself working towards and consistently. as you’re mastering your craft and building your unit. like, what would be your best piece of advice for anyone looking looking to jump?

Jessie Dillon
I think investing in coaching is probably one of my best pieces of advice. because a lot of people just aren’t going to take action. when they learn something through a free podcast or a free video. Whereas if you pay somebody for their time. and they’re teaching you the same exact thing.

you’re just more likely to actually go use it. because you have skin in the game now. and you have somebody that you’re going to answer to on your next call with them. when they’re gonna ask, Hey, did you do the thing that we said you had to do? You know, and then another piece of advice would just be to find a buddy.

find other people who are doing what you want to be doing. and figure out how you can spend more time with them. how you can kind of insert yourself into their projects. how you can just run in the same circle as those people. because if your circle is not full of entrepreneurs. or business owners or investors. it is just going to be harder to hold yourself accountable. And it’s going to feel more lonely.

What Would Jessie Older Self Tell Her Younger Self

Pamela Bardhi
Right? Absolutely. I love that. Because that was the same thing that I just watched. Yeah, I mentioned that when I spoke at the meetup that you know. I invested in the coach as well. And that’s really what propelled me forward because they hold you accountable.

And they, you know, they teach you that Been there done that. I love that. And now this is my favourite question. What would your older self tell your younger self based on what you know, now,

Jessie Dillon
you’re not a bad employee, these jobs just suck.

Pamela Bardhi
That you’re meant to be an entrepreneur? Yeah.

Jessie Dillon
It’s crazy to think how much farther I could be with my self employment journey. Now, if I had started even just two years earlier. those two years would have been that much messier. because I had that much less experience. But I’m the perfect example of like, holy shit. Look at how much can happen in a year or two years.

A year and a half ago, I listened to my first real estate rookie podcast episode. And now a couple months ago, I was a guest on the podcast. A year and a half ago, I went to my first meetup. And now next week, I’m speaking at the meetup.

And it was so funny because me and my husband were sitting there at that first meetup we went to in Worcester. And I was like, jokingly, I’m like. I’m gonna be up there talking one day in like. give me like a year. And now a year and a half later. I’m gonna be the one up there talking. It’s just crazy. How much can happen in a year. So I wish I had started even just like a year earlier.

Pamela Bardhi
Oh, my God, I just got chills everywhere when you mentioned that. So amazing to see that like, this is exactly it. Like you just kept going. You executed and like, there were no excuses.

You just kept building and kept going. I love that, Jesse. So like, now because you’ve built a $1.5 million portfolio. within literally 1.5 years. What’s happening in the next six months for you? Like, what’s what’s going on?

Jessie Dillon
Like many, I ran out of money to invest. And I was like, Did I screw up somewhere? I feel like I shouldn’t have this problem right now if I did well. like with these first three deals. and then I went to BP con and I realised literally everybody. either has hit that point and figured out how to move forward.

They’re at that point now and don’t know what to do. Or they hit that point, and they gave up. so I’m like, I didn’t screw up. It just really is a team sport. After a couple of deals. I found a really great silent equity partner that I’m going to be. I’m looking for the next deal with so she’ll be bringing the money to the deal.

I’ll be doing all the work and we split all of the equity and cash flow 5050. So we’re looking for something minimum 12 units within like an hour and a half from Central Mass. something that ideally is maybe just a little mismanaged like under market rents.

but we’re not looking for any like major rehab or renovations or anything. and the plan is to add 50 more rental units with silent partners this year. so that’s why I’m looking for minimum 12 units. because I’d love to bang it out and no more than four deals.

Pamela Bardhi
Oh, that look You go girl. Oh my god, and I know you’re gonna get there. The fifth units is gonna happen without a doubt. Because you are amazing.

I love your story, I love your energy. Like seriously, where everything’s going for you. I absolutely love it. You’ve got to let everyone know where to find you now. but where can everybody reach Jesse?

Jessie Dillon
Instagram is definitely where I hang out most. I’m on a little social media hiatus right now. But it’s on Instagram. I’m Jesse Dillon with an underscore at the end

Pamela Bardhi
thank you so much for being here today. You’re an absolute Rockstar. and I can’t wait to see where you are in like six months or a year from now. So that’s it for today’s episode of underdog.

catch us next week, always dropping on Thursdays. And remember, if you’re interested in real estate or want to learn how to create more money. and magic in your life, check out meet with and let’s chat sending you so so much love



Tune in to the episode to hear the rest of my incredible interview with Jessie Dillon.

If you found this story worth your time and made changes in your life, we’d love to hear from you! Subscribe and leave a review.

The Underdog Podcast host is none other than Pamela Bardhi. She’s rocking the Real Estate Realm and has dedicated her life as a Life Coach. She is also Forbes Real Estate Council. To know more about Pam, check out the following:

If you’re interested in elevating your life 10x, and owning your power, Pamela invites you to join her for a 15-minute call to set your goals straight and get clarity. Start building your game plan now: