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All Forum Posts by: Jessie Dillon

Jessie Dillon has started 12 posts and replied 304 times.

@Steve K. these are specific to women :) @Elisa Michals they also have a wiire facebook group! 

Post: Do I sell and set myself up OR keep as a break even rental?

Jessie DillonPosted
  • Investor
  • Hopedale, MA
  • Posts 319
  • Votes 210

if your goal is cashflow, but you don't want to self-manage a STR or MTR, then selling to make that equity work harder for your somewhere else is the only thing that makes sense.

q: would your time be better spent focused on flipping & letting that rental break even, or going through the process of turning that equity into cashflow via a 1031? 

Post: Hi 👋🏼 BP community

Jessie DillonPosted
  • Investor
  • Hopedale, MA
  • Posts 319
  • Votes 210

hi samar! welcome! i'm a value-add multifamily investor & would love to help you along on your journey. feel free to message me and let me know exactly what you are needing help with. i have experience with long distance, partnerships, LTR/MTR/STR, as well as rent by the room, househacking, creative financing, and wholesaling.

Post: Phone used for Landlord?

Jessie DillonPosted
  • Investor
  • Hopedale, MA
  • Posts 319
  • Votes 210

i personally use my regular phone but you could use a google voice number or an actual physical work phone with a different line. i'd do google voice so you're not carrying around 2 phones. :)

so most people will have to be as leveraged as possible to scale (at the beginning). as in, keep your LTV high and focus on buying 'as much' ($$) RE as possible. this is if you're doing a pretty run of the mill REI strategy like buy and hold. i came across an interesting guideline once: if you could sell today and net 7x+ your annual true net cashflow, you should cash-out/refi, or sell/1031. think of it this way: if your portfolio in a year is worth 1m market value, and you owe 600k, and have a lender that will do a portfolio loan at 80% ltv, you could cashout refi and get 200k to play with (minus closing costs). when you compare the now-lower cashflow from the existing portfolio (higher LTV & maybe different rate), to what you can do with 200k cash, THAT'S where it gets fun. maybe you lose 1k/mo in cashflow on the original portfolio (literally just made up a number, idk), but you can gain 2500/mo in cashflow with that 200k.. then doing the cashout/refi earned you a net increase in your monthly profit of 1500/mo, plus you're getting debt paydown and appreciation on "more" real estate, probably getting bigger tax benefits, etc. & how does the 1500/mo in increased net profit compare to the closing costs you paid on the cash-out/refi? that COULD BE looked at as your COCR in moving around this equity.

but to answer your actual question, it depends on your long term goals. if you want a million units you'd be better off in multifamily. if you want a small but mighty portfolio that you're always optimizing, maybe have some STR some MTR in there, self-manage, keep it simple... you could stick with SFH and probably have an easier time managing.

Post: Which real estate strategy works best to escape the 9-5 rat race?

Jessie DillonPosted
  • Investor
  • Hopedale, MA
  • Posts 319
  • Votes 210

if you have that one finite nest egg to work with & will not be able to quickly keep saving more, then your best option is going to be either BRRRing or gator lending. my opinion!

i was at a retreat a year or so ago with a girl who started with an 80k nest egg BRRRing single-family homes in dallas, and has scaled to i believe over 80 of them? starting with just that original 80k of her own money! her and her husband both retired from their day jobs and have all these gorgeous renovated SFRs. the key was that they got better and better at BRRRing and the nest egg grew just a little bit with each cashout/refi, so they could do bigger/better deals, then multiple deals at once. this obviously took time, but they're getting ALL the perks of REI: debt paydown, appreciation, tax benefits, cashflow, the opportunity to provide beautiful safe housing in the city they live in... if you BRRR'd your way to a few STRs instead of LTRs, you could probably arrive at that 7k/mo number pretty quick. also consider BRRRing to MTRs.

gator lending is short-term / transational lending, usually to wholesalers for deposits. pace morby has a course on it. most people i'm sure take the course, do nothing with the information, make no money, then complain and say the course didn't work lol. but i do know tons of people actually make great money gator lending.

flips obviously work too but you usually LOSE money on the first one, break even if you're fortunate... it's very active work too, so doing flips while you're still working full time, idk, not a fan personally. you'd have to KEEP flipping to KEEP making 7k/mo, vs with BRRRing you'll eventually get to that 7k/mo and can stop or regroup.

I'm writing this as I'm on my flight home from the Phoenix retreat, which was my third one, & have to share!

If you haven't heard of WIIRE (women invest in real estate), it's a mostly-online community created by @ameliajorei and @grace.investing (instagram handles). I originally heard these two on the BP Rookie podcast a couple years ago, loved their energy, and loved seeing other younger women doing what I wanted to be doing, so I connected with them on IG & have been watching WIIRE evolve since then.

The whole WIIRE brand is about authenticity, fun, collaboration, everyone belonging, finding your confidence, cheering each other on.. It's a really unique vibe that I don't get from any 'similar' groups.

They do have some great online courses, but a few times a year, they also host 3-day retreats in different cities for 17-20 strangers, who seriously do leave with lifelong friends at the end. 

I've gone to the Denver, Orlando, and now Phoenix retreats over the last few years, and would highly recommend these to anyone who's either a beginner investor (1-2+ deals), or 'middle investor,' and doesn't really have many investor ladyfriends in real life to lean on. 

Some of what we usually do over these 3 days: Small group hot seats (3-4 people), masterminds, small group goal-setting.. The mastermind topics from this trip were partnerships, creative financing, and tech/software. With just 17-20 attendees, you can really get to know each person's 'haves and wants' to see how you could collaborate, and the masterminds are so interactive, more like a discussion, so everyone feels comfortable asking questions and gets really thorough answers. There's a good amount of downtime baked in too so that you can dive deeper with anyone you're really connecting with, or get some solo work time in to start implementing what you're learning.

Side note: They always book huge, gorgeous houses, and there never any no shortage of fresh food & drinks. The cost includes your stay, all food, drinks.

I know many women go with a specific goal in mind, but there is so much power in just BEING AROUND people who you can relate to, who are doing what you want to be doing, and who usually happen to have creative solutions to problems you've been stuck on & had no one to brainstorm on with!

Amelia and Grace really foster such an amazing atmosphere where everybody truly feels like they can be themselves, be silly, ask the 'stupid questions,' be VULNERABLE, etc. No one has to put on a front at these retreats. It's so refreshing. And unlike a lot of other coaches/mentors/personalities in this space, they participate in all the activities on the schedule themselves, too!

I seriously feel like I leave these retreats with solutions, feeling un-stuck, feeling inspired, feeling validated, motivated, reassured, confident... If only they had them quarterly lol.

They did just open their waitlist for the next one which is in Utah in September. If you're on the fence about making the investment, literally just figure it out and make it happen because these are so game-changing. 

I had zero real estate investing experience, no one in my family did it... I did have small business experience, but only so much can be applied... And I managed to 8x my net worth via real estate in the last 2y, 99% thanks to WIIRE & the people I've met through this community.

TLDR; Highly highly recommend these retreats to any woman who's ISO a community of like-minded, fun, authentic ladies to help pull them forward. 

Feel free to DM me if you have any private questions about these retreats, happy to chat!

Post: What to do with $1,000,000.00?

Jessie DillonPosted
  • Investor
  • Hopedale, MA
  • Posts 319
  • Votes 210
Quote from @Kevin S.:
Quote from @Jessie Dillon:

when you say 'approaching retirement,' how long are we talking? one option would be using it to BRRRR enough properties to generate the desired amount of monthly profit in the end. as far as cash vs down payment, if you want to build more wealth over time, i would definitely use debt so that you can buy 'more' ($) real estate. leaving it in index funds isn't a BAD idea, but if you have the resources (time/knowledge) to invest in RE & do it wisely, you will likely come out so much farther ahead. another question here is, how much monthly income are you looking for this nest egg to generate in retirement?


 How much monthly income can 1M generate in about 9-10 yrs in RE (leveraged)?  Try to leave 'it depends' out. LOL.  Guesstimate based on normal, average, median, 50% percentile.  Thanks. 


'the limit does not exist' - you could BRRRR at lightning speed

Quote from @Kalp Mehta:

@Jessie Dillon

Hello neighbor!

It's great to connect with someone from South Central MA! Your point about buying turnkey properties at a significant discount for BRRRR is key. How have you found the market conditions in the area for securing those favorable deals? Any specific strategies or tips you'd be willing to share with a fellow local investor?


for sure! finding turnkey properties at a discount isn’t easy. it happens though! high days on market & you just so happen to offer low in the right way at the right time.. but mostly you’ll have to go offmarket to buy a nice property at a discount. from a seller who needs to move fast and doesn’t want to (or doesn’t have time to) hire an agent. in more expensive markets especially, people with nice properties know they can sell high on-market, so they’re less likely to take a low offer offmarket, but it’s not impossible. 

Post: Coming to the US - Where should I start?

Jessie DillonPosted
  • Investor
  • Hopedale, MA
  • Posts 319
  • Votes 210
Quote from @Marco Spaziani Brunella:
Quote from @Jessie Dillon:

if you're looking for high-cashflow areas, for LTRs, the midwest seems to be the place to be. but if you're doing MTR or STR strategies, the shenandoah area might be the next hot spot for mountainous STR markets. wholesaling is a ton of work up front & i feel like a smaller % of people succeed in it, vs the larger % of people who succeed with actually buying rental properties.

 Thanks for your input, Jessie. That was my impression as well about wholesaling. I'll add those areas to the watchlist.

As a new immigrant, I am concerned about how quickly you can build your credit score to talk to lenders. How is the local lending environment in the area you suggested? Do they do DSCR loans on MTRs/STRs?

When I moved from Italy to Spain, I carried my credit history with me as the two countries have a very tight relationship and very similar systems. The US is much different in that sense.


 i’ve heard it’s pretty difficult to get loans at all if you are not a citizen, but you may be able to do hard money / private money or partner with a citizen?