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  • Writer's pictureJohn Casmon

How Losing His $300,000 Job Sprung Him into Freedom with Jonathan Twombly

Picture being the sole breadwinner for your family and then losing your job. How would you feel? What would you do? Are you positioned to absorb this type of hit?

Jonathan Twombly is president of Two Bridges Asset Management LLC. He began his career as a corporate lawyer and focused on real estate and hospitality matters. In 2011, he was let go from a job that paid him over $300,000 and he says it was one of the greatest things to happen to him. He focused on real estate investing and created his company Two Bridges Asset Management.

He built a portfolio of apartments in the Carolinas and as the market heated up, he decided to pull back on acquisitions. He’s focused on building his investor base to prepare for new deals and is seeking distressed opportunities.

In this episode, Jonathan shares how he was able to have success as an apartment syndicator. He also shares where he sees opportunities in today’s market, mistakes new syndicators make, and how Jonathan grew his Facebook community to over 11,000 members.

Listen Here:

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Insights on Finding the Best Real Estate Deals

  • From a corporate lawyer on Wall Street to real estate syndicator

Getting let go from my job was one of the best things that ever happened to me because everything became a possibility.
  • Getting out of the proverbial golden handcuffs of a good-paying W2 job

  • Keeping up with the Jones’ will not help you towards your financial freedom

I’m not motivated by having more, but by how far out can I extend my freedom window.
  • Creating time freedom through real estate investing

  • Launching his syndication company Two Bridges

  • Building an investor base for future deals

  • The syndication market today, and where Jonathan finds good deals

  • The number one mistake new syndicators make

If you overpay, you set yourself up for real pain if anything goes wrong.
  • What to look for when analyzing a deal

  • How to determine whether a real estate syndicator has their investors best interests in mind

  • Syndication properties that are safe bets during COVID

You can’t focus on upside in this market, you have to be thinking about the safe thing to do with your investors' money.
  • How Jonathan grew his Multifamily Investment Community group on Facebook with 11,000 members

  • Multifamily Launchpad, an easily accessible, high-quality coaching program

Bullseye Round:

Apparent Failure: I made a lot of mistakes on my first syndication deal, and it became a nightmare. I learned so much more doing that deal than through any of my best deals.

Digital Resource:

ConvertKit (Email software)

Most Recommended Book:

The War of Art (Steven Pressfield)

Wish I Knew When I Was Starting Out:

How to build an audience and raise money. If you find a great deal, the money will find you, is not true.

Daily Habit:

The 90-Day Year planning system

Best Place to Grab a Bite in Brooklyn, NY

L&B Spumoni Gardens

Contact Jonathan:


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