When Toby Banta stepped in as Executive Managing Director at Eastern Real Estate nearly six years ago, the firm was hitting its stride. Even as COVID sent markets spinning, Eastern closed twelve deals in just two years - spanning multifamily, industrial, commercial, and hospitality - not only in New England but across the country. 

Then, the market shifted. 

Over the next three years, Eastern closed just two deals. For a fourteen-person office, a slowdown like this hit hard. But instead of forcing deals, Toby and the team stayed disciplined, passing on anything that didn't meet the Eastern standard. 

That selectivity is now paying off. 

Toby leads investment strategy and asset execution at Eastern Real Estate alongside co-founders Dan Doherty and Brian Kelly. His primary responsibilities span sourcing new acquisitions, joint ventures, and capital formation, as well as serving on the Investment Committee. Toby's expertise has been built on nearly twenty years in real estate, working across every side of a deal, and the completion of over thirty investments totaling more than $6 billion.

Inside this week's episode:

• Why the Eastern team structures every deal with multiple paths to success and refuses to make a binary bet 
• The $140 million, 360-unit ground-up deal in Portsmouth, and how Toby and his team got it into the ground in a market that institutional capital largely passed on 
• How Eastern's practice of putting its own capital into deals alongside its investors shapes the way Toby and his team evaluate risk at every stage 
• What Toby learned about risk and opportunity by working across leasing, capital markets, investing, and development before landing at Eastern 
• The legendary Wang HQ deal: acquired for $525,000 and sold for over $100 million just four years later

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