BP Podcast 172: Breaking Into Apartment Investing with a 100-Unit First Deal with Jonathan Twombly


Have you ever dreamed of owning large apartment complexes? If so, don’t miss this powerful interview with Jonathan Twombly, a real estate investor whose very first deal had over 100 units! You’ll learn why Jonathan skipped the “small deal phase” and jumped right into big deals — and how he’s gone from nothing to over 400 units in the past several years. This show offers an incredibly realistic view of what it actually takes to break into the apartment complex market!

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This Show Sponsored By

We just waRealtySharesnted to give a shout out to our podcast sponsor on today’s show: RealtyShares. RealtyShares is a crowdfunding platform that allows you to invest in professionally managed properties without leaving your living room!

Learn more by visiting RealtyShares.com/biggerpockets!

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PATLive-LogoWe just wanted to give a shout out to our podcast sponsor on today’s show: PATLive. PATLive’s team of superstar receptionists will always leave your customers delighted. Every agent goes through a rigorous training course before they can answer calls, and we’ve got quality assurance down to an art.

Learn more by visiting PATLive.com/biggerpockets!

In This Episode We Cover:

  • How Jonathan got out of the law industry and into real estate investing
  • The partnership that changed his life
  • How you can always find deals within 100 miles
  • The details of Jonathan’s first deal
  • What to do when someone cancels the deal
  • How financing contingency works
  • How he structures his deals
  • Tips for establishing yourself with brokers
  • The due diligence list to show to brokers
  • The importance of asking your friends for introductions
  • Why you should focus on the relationship aspect of investing
  • The details of Jonathan’s first successful deal
  • Why you should consider buying the “unsexy” properties
  • Tips on looking for deals
  • How he makes money through syndication
  • His strategy on making 400-unit deals
  • How he manages properties
  • What you should know about underwriting a deal
  • Things he would done differently if he started all over again
  • And SO much more!

Links from the Show

Books Mentioned in this Show

Tweetable Topics:

  • “You don’t know what the heck you are doing, but you’ll figure it out when you start somewhere.” (Tweet This!)
  • “If you are a new investor, it’s not about how much money you have but about how many deals you have closed.” (Tweet This!)
  • “Persistence is 90% in business and then the other 10% is not being an idiot.” (Tweet This!)

Connect with Jonathan

About Author

Thanks for checking out the BiggerPockets Real Estate Investing & Wealth Building Podcast. Hosts Joshua Dorkin & Brandon Turner strive to bring top-notch educational content and interviews to our listeners -- without the non-stop pitch prevalent around the industry. With over 80,000 listeners per show, the BiggerPockets Podcast has become the biggest real estate podcast in the world. But don’t take our word for it. We’re the top-rated and reviewed real estate show on iTunes — check it out, read the reviews on iTunes, and get busy listening and learning!


  1. melissa nevich

    Thank you, Jonathan! Great info. We are trying to break into over 5 units – live in NY looking to buy in NC so this hit close to home. We lived in Charlotte for 8 years so I’ll start asking friends for commercial agents. I’ll keep pushing because these ‘on-markets’ are just silly!

  2. Marcel Duarte

    Great show this week Jonathan, Josh, and Brandon! It was really inspiring to hear about the perseverance it took to finalize the first deal after the initial two didn’t work out. I think most folks wouldn’t keep with it after that. It reminded me of episode 170 when Andrew Cushman said made over 4,000 phone calls to get his first deal. It’s no coincidence Jonathan and Andrew have had such similar accomplishments.

    I know you guys ran out of time at the end, but I would love to hear more about financing and syndicating these deals. I vote for a Jonathan Twombly Round 2 episode!

    Thanks again for another fantastic show.

  3. Joshua Keene

    Another great show! Lots of interesting nuggets of information and advice throughout. One part of the podcast that really caught my attention was when Jonathan mentioned checking the existing tenant’s credit when performing your due diligence to make sure the seller isn’t filling vacancies with unqualified renters. This can really hurt you and your deal if overlooked.

    Thank you Jonathan, Josh, and Brandon! Looking forward to the next podcast!

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