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All Forum Posts by: Josh Calcanis

Josh Calcanis has started 25 posts and replied 127 times.

Post: Buy and hold investments - Winter Park, Florida

Josh CalcanisPosted
  • Rental Property Investor
  • Orlando, FL
  • Posts 131
  • Votes 62

@Eric Boutwell Just to add to some of the areas listed by @Kevin Gidusko I'd throw the Mills50/colonial town north into the mix. I've invested in the UCF area, Thornton Park, and the Mills50 area so far. I found a great deal in the Mills50 area in 2017 and have lived here since then. There are always multis in the area up for sale and with the consistent development in this area you can find a good deal with some upside in a few years if you're planning on house hacking.

Post: Creative use of a Drone?

Josh CalcanisPosted
  • Rental Property Investor
  • Orlando, FL
  • Posts 131
  • Votes 62

Thanks for the awesome replies! Definitely looking into the possibility of a side hustle here, not my primary source of income. Sounds like some further degree or mapping/surveying might be the route to go.

Post: Creative use of a Drone?

Josh CalcanisPosted
  • Rental Property Investor
  • Orlando, FL
  • Posts 131
  • Votes 62

Hey BP!

I earned my Private Pilot Certificate about a year and a half ago. Shortly after that I took the test for the Part 107 Certificate (Drone Pilot) since I had already amassed quite a bit of knowledge on airspace, regs, etc. 

While I know aerial photography and videography is pretty common in commercial/residential real estate, I'm exploring new (possibly unsaturated) markets for something like that. So far I see some potential in insurance claims (hurricane damage/roof damage/flooding), undeveloped land (mapping/surveying), and construction sites? 

With the massive amount of knowledge and experience on here, where do you think there is potential to provide value as a drone pilot? 

Post: Is anyone investing in Florida market?

Josh CalcanisPosted
  • Rental Property Investor
  • Orlando, FL
  • Posts 131
  • Votes 62

Hey @Jacob Walls! I totally understand getting into a market you are familiar with. I did my first deal back in 2015 in Orlando, FL while I was still living in Seattle. Why? Because I was much more familiar with the market here vs any of the other states I had lived in. I've been doing one deal every 12-18 months since a lot of my time has been focused on the startup I'm at. So to answer your original question...

I have been focused on live and flip/long term rentals since I've started. I've found all the deals through searching myself and from off-market deals from the realtor I regularly use. I also have a craigslist alert set for foreclosures and other deals (haven't seen much benefit from craigslist yet). I'm also part of the local REIA, which meets on edge-water regularly. This email chain/meeting has a lot of deals that might not necessarily make it to the market.


I think you can find a great deal in any market (although it obviously will be more challenging depending the cycle the markets' in). For example, I found the duplex I'm currently living in for a steal in the Mills50 area from Redfin. This was one I had to find myself searching through the alerts I set up in Redfin.

Good luck!

Post: Orlando, FL mentorship

Josh CalcanisPosted
  • Rental Property Investor
  • Orlando, FL
  • Posts 131
  • Votes 62

@Shawn G. makes a good point. CFRI has a monthly meeting out of Edgewater High School. Pretty large chapter that has plenty of time to network and meet some of the vendors that hang out in the lobby. 

Another point is to truly understand what you want to do. I'm bias towards buy and hold for a first investment, but there are arguments for both (https://www.biggerpockets.com/renewsblog/2013/07/23/wholesaling-strategy-beginner-experienced-investor/). 

Depending on your finances, the money you would use to wholesale, you could put down on a duplex or triplex and move in using an FHA loan. Then partner with someone at one of those CFRI meetings on your first wholesale (or flip) and learn something. By partner, I'm not necessarily meaning someone is going to give you a piece of the pie for offering nothing in value, but someone you can follow through the steps and learn.

Post: Best Business Bank Account for REI

Josh CalcanisPosted
  • Rental Property Investor
  • Orlando, FL
  • Posts 131
  • Votes 62

Thanks @Logan Allec

From you're experience, what's the downside with Capital One?

All I'm looking for is an account/credit card I can run all these expenses/cash flow through. Just to separate personal income/accounts from my REI. I don't need a brick and mortar location at this point.

Post: Best Business Bank Account for REI

Josh CalcanisPosted
  • Rental Property Investor
  • Orlando, FL
  • Posts 131
  • Votes 62

Morning BP,

After 3 years of investing and 6 doors, I'm going to start treating my REI as more of a business. This includes doing a much better job at book keeping. I thought I was doing a good job until I went to my CPA last year and he absolutely ripped me apart in terms of keeping organized.

With that said, I have an LLC that I have not placed any properties in yet (would need to Quit Claim or push through a Land Trust into the LLC) and would like to start separating my REI cash flow, expenses, etc from my personal checking. In your experience, which banks have been the most small business friendly *business* accounts? I.E. lower running checking limit, no limit on transactions, etc.

I'd prefer to go with one of the larger banks (ease of use and accessibility), but if you've got a great local bank, for reference I'm in Orlando, FL.

Post: Amazon HQ2 - REI Opportunity?

Josh CalcanisPosted
  • Rental Property Investor
  • Orlando, FL
  • Posts 131
  • Votes 62

@Kraig Kujawa I agree with Miami with not being the best fit. I don't feel it fits the Amazon culture I was familiar with when I lived in Seattle. The metro isn't anything impressive either (as is Orlando's)

Post: Amazon HQ2 - REI Opportunity?

Josh CalcanisPosted
  • Rental Property Investor
  • Orlando, FL
  • Posts 131
  • Votes 62

To avoid starting another thread, I'll stick with updating this one...

News from this morning is they've narrowed it down to 20 cities. To be honest I'm surprised by some. Nashville for example in no way checks off the public transportation box and the highway infrastructure is already showing stress from the rapid influx over the last couple of years.

In terms of REI, a lot of the cities seem relatively low cost ( aside from NY, DC, Miami, LA, and Chicago) for an investor based off of what I've seen on BP. Keep in mind I live in Orlando and have only invested in Central Florida as of 2018, so take that comment for what it's worth.

Now that there is an updated list... what are your thoughts?

https://www.geekwire.com/2018/amazon-narrows-hq2-s...

Post: 3rd Deal with No (liquid) Cash Down

Josh CalcanisPosted
  • Rental Property Investor
  • Orlando, FL
  • Posts 131
  • Votes 62

@JR Paulemon Congrats! I haven't explored the AirBnB market, but there are a lot of people on here that are really successful with it.

You'll like the Mills50 area for sure. I feel it'll have the chance to become another College Park type area.

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