Jay Bowman

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Jay Bowman

Jay Bowman

@jaybowman

RE Investor of 18yrs+. Owner/operator of 18 short term rentals and counting. Follow to join me on this journey.

Louisville, KY Bergabung Eylül 2007
1K Mengikuti2.9K Pengikut
John Solwold
John Solwold@Solwoldjr74·
Reviews like this are the reason I'm in this business. These guests will never forget their vacation in the Smokies. I feel honored they chose my cabin and burdened to make sure my cabin is a positive part of their memories. My advice to fellow STR owners is make reviews like this your "Why" & you'll be successful.
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Jay Bowman
Jay Bowman@jaybowman·
I’ve never written a line of code in my life. I’ve happily left that up to people who worked much harder than me in school. I wouldnt even know where to begin without online tools. Panda and python were foreign words to me. Simply out of curiosity I wrote a script yestrday to identify owners within 15 mins of the coast in Pinellas County, FL who have had a Lis Pendens (foreclosure) filed against them and fall within the county jurisdiction and not a small city’s. And by “wrote” I mean I cut and pasted w AIs guidance. I pushed AI by acting like I was an 85yr old looking at a computer for the first time. I tried to break it by asking the dumbest questions. No anger or frustration from it. Just education and positive reinforcement and encouragement the entire time. I was like a child playing grown up in his dad’s hat and coat while sitting behind the wheel of his Ferrari. Unbelievably powerful.
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Taylor Jones
Taylor Jones@MrJonesSTRs·
Where are all those "Michigan is great" people from 6 months ago? Can't seem to find them
Tom Wachs, CBM@Tom_Wachs

This is unreal. @RobertRayWx from @foxweather was in Benton Harbor, Michigan on Wednesday night covering this intense lake effect snow band. It looks like a hurricane in the winter. One of the wildest live shots I've seen in a long time.

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Jay Bowman
Jay Bowman@jaybowman·
This is Steve. Steve owns and operates 101 SFRs in small town America. He manages them all from his cell phone and pick up truck. Steve is clearly the problem when it comes to a lack of affordable housing in America. It’s most definitely not the NIMBYs and fiefdoms that cities have created within themselves to maintain power over developers who (gasp) want to build nice properties to make a profit. It’s Steve. Steve is the problem.
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Jay Bowman
Jay Bowman@jaybowman·
When you wake up and find multiple overnight winter bookings.
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Jay Bowman
Jay Bowman@jaybowman·
@Fire5280 Or, if your LTV is too high, sell the minimum you have to and reduce the debt to 50-60% to protect yourself from any potential downturn in values or revenues in the future.
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Mile High FIRE
Mile High FIRE@Fire5280·
@jaybowman I hear your point, but i would pay off this mortgage with capital in a non-tax-advantaged Fidelity account. So the growth in that account would be taxed eventually.
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Mile High FIRE
Mile High FIRE@Fire5280·
One of our STRs, which has a $652,000 adjustable rate loan balance, is scheduled to reprice in February from $4,693/mo (P+I), up to about $5,617/mo, assuming a new rate of 6.375%. We have more than enough liquidity in our non-tax-advantaged accounts to pay off some or all of the remaining loan balance. If we paid it off in full, it would mean a guaranteed annual cash-flow increase of $67,400. If we instead leave that $652,000 invested in the market, it would need to grow by 10.3% annually to yield $67,400 in growth. I'm leaning towards paying it off, as it's hard not to jump on an opportunity to increase our monthly cash-flow by such a sizable amount. What would you do?
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Jay Bowman
Jay Bowman@jaybowman·
@Fire5280 Yes, but you’d have control over the amount removed to be taxed. Over time your debt would be reduced on the real estate and you’d achieve the same goal w/o the immediate taxation. It just takes a bit longer.
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Jay Bowman
Jay Bowman@jaybowman·
@grok What about Castle Rock and Steamboat Springs?
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Grok
Grok@grok·
Based on latest data, here are the continental US cities meeting all criteria (elevation ≥6000 ft, pop ≥12k, median income >$65k, within 1hr of commercial airport): - Cheyenne, WY - Colorado Springs, CO - Durango, CO - Flagstaff, AZ - Los Alamos, NM - Rock Springs, WY - Santa Fe, NM Let me know if you need details on any!
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Jay Bowman
Jay Bowman@jaybowman·
Hey @grok Tell me all of the cities in the continental US that are 6000 ft above sea level, within an hour drive of a commercial passenger airport, have a population of 12,000+ and have a median income that exceeds $65,000/yr.
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Moses Kagan
Moses Kagan@moseskagan·
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Andrej Karpathy@karpathy

Agency > Intelligence I had this intuitively wrong for decades, I think due to a pervasive cultural veneration of intelligence, various entertainment/media, obsession with IQ etc. Agency is significantly more powerful and significantly more scarce. Are you hiring for agency? Are we educating for agency? Are you acting as if you had 10X agency? Grok explanation is ~close: “Agency, as a personality trait, refers to an individual's capacity to take initiative, make decisions, and exert control over their actions and environment. It’s about being proactive rather than reactive—someone with high agency doesn’t just let life happen to them; they shape it. Think of it as a blend of self-efficacy, determination, and a sense of ownership over one’s path. People with strong agency tend to set goals and pursue them with confidence, even in the face of obstacles. They’re the type to say, “I’ll figure it out,” and then actually do it. On the flip side, someone low in agency might feel more like a passenger in their own life, waiting for external forces—like luck, other people, or circumstances—to dictate what happens next. It’s not quite the same as assertiveness or ambition, though it can overlap. Agency is quieter, more internal—it’s the belief that you *can* act, paired with the will to follow through. Psychologists often tie it to concepts like locus of control: high-agency folks lean toward an internal locus, feeling they steer their fate, while low-agency folks might lean external, seeing life as something that happens *to* them.”

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Jay Bowman
Jay Bowman@jaybowman·
@Fire5280 If the securities value fall beneath a certain level (LTV) they’re going to come knocking for cash.
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Mile High FIRE
Mile High FIRE@Fire5280·
I'm looking into possibly using a securities-based line of credit against my Fidelity taxable investment account, to pay off the $650,000 mortgage balance on an adjustable rate loan, that is looking likely to adjust up to 6.40% at the end of February. This route would eliminate a $5,618/mo mortgage payment from the books, and replace it with a $3,255/mo interest-only payment on the line of credit. This would increase my monthly cash-flow by nearly $2,400, and save me from having to liquidate any of my existing Fidelity holdings, which also saves me from any capital gains tax burden. I've never used a securities-based line of credit before, so I'd be curious to hear what others think of this plan. What are the pros and cons that I might be overlooking. Thanks!
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Jay Bowman
Jay Bowman@jaybowman·
“How did you get into real estate investing, Jay?” I was in Springfield, MO in 2000 and had gotten fired from my editing job at a local TV station. I’d been interested in getting my RE license bc “I was a people person” and “could make a lot of money.” 🫣 12 months into my RE agent career I remember seeing a small house for sale and thought, “If I could buy that and rent it out I’d make… (does math in head)… $150 a month.” I may or may not have been guessing. Didnt matter bc the seed had been planted. My mind raced. I’d only need 100 of those to make $150k! Fast forward 6 years and the seed had grown into a withered sapling: un-nurtured and stagnant. Hating my job in mortgage lending and not wanting to return to being a RE agent I found my way into my local REIA in Louisville. With a little bit of education and whole lot of fear I bought my first house in 2006 in a terrible area of town w a tenant in it for $11k. “This is awesome! They’re gonna give me $300 in cash flow every month!” 3 months later they moved out without notice into the house next door. 🙄 Sold that dog for $20k in 2018. Hard lessons learned in between that I wouldn’t give away at any price.
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Phil McAlister
Phil McAlister@phil_mcalister·
That sound you hear is me and every other real estate guy in Chicago furiously looking up ownership information on every large parcel near the highway in northwest Indiana.
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Jay Bowman
Jay Bowman@jaybowman·
@MrJonesSTRs We discussed this behavior in our last session Taylor…
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Taylor Jones
Taylor Jones@MrJonesSTRs·
I guess you could decide to live in Minnesota or Ohio…. But why would you? Long Florida 😎
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Jay Bowman
Jay Bowman@jaybowman·
@moseskagan Mindset issue. Their focus is the money and not the client.
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Moses Kagan
Moses Kagan@moseskagan·
Will never understand property managers who behave unprofessionally during the process of off-boarding a property. You're already losing the business, anyway. Why compound the damage by hurting your brand?
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Jay Bowman
Jay Bowman@jaybowman·
Operating large properties where families gather is a different beast. The holiday cleaning expectation is at the same level of a personal residence which, if we’re being honest, is already at an unachievable level. “Is that a leaf on the floor! Who walked outside and brought a leaf in! Animals… all of you!” Add that the guests are already on unfamiliar turf and every issue, real or pretend, becomes magnified. Queue the late night messages… But this is what we chose. “We thought ‘Sure… that carrot looks nice and juicy but have you tried the stick?’” So instead of complaining, stand up, put your big boy pants on and find the truth in the issues brought to your attention and attack them with the same passion with which the guests brought them. If that’s not your mindset, get out of the way and let true Operators do what they do best… operate.
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Jay Bowman
Jay Bowman@jaybowman·
How true STR Managers of large properties prepare for Thanksgiving guests.
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