Derrick Barker is the co-founder and CEO of Nectar, a real estate tech financing company that provides liquidity to commercial real estate sponsors across the country. Nectar has completed more than 140 deals across 29 states, deploying over $40 million to lower middle market and middle market operators who need access to equity trapped in their existing assets.

After leaving Goldman Sachs, Derrick built his real estate portfolio to more than 4,700 units and $400 million in asset value across multiple brands, including Civitas Communities, a multifamily platform focused on transforming distressed assets into quality housing, and DOMOS Co-Living, a co-living concept renting larger units by the room.

Derrick began buying real estate from his dorm room at Harvard, where he also founded a student organization connected to Wall Street that became his first major business success. After graduating, he spent three years trading complex securities at Goldman Sachs while simultaneously building a 500-unit portfolio in his hometown of Atlanta before leaving to focus on real estate full time.

Derrick Barker on Multifamily Growth and Tech-First Lending

When Derrick Barker was four days from his earnest money going non-contingent on a Koreatown property, his lender came back short. He had equity sitting across his portfolio at 40% and 50% leverage. He didn't want to refinance. There was no clean way to access it without tripping a covenant. That's the problem Nectar exists to solve.

Building Nectar meant becoming a technology company first. Derrick went through Techstars, built AI-native processes from the ground up, and created tools his borrowers use to run their businesses more efficiently. The platform is built to provide both data and liquidity to commercial real estate operators.

In this episode of The Dealmakers' Edge, Aaron Strauss and Derrick Barker discuss how he built a multifamily portfolio while trading at Goldman, how Nectar is structured to give sponsors access to trapped equity without tripping existing loan covenants, and why relationships matter more in the age of AI than they ever have.

1:44 - Starting his first business at Harvard and how it connected to Wall Street

3:14 - What it felt like walking onto Goldman's trading floor right after the crisis

5:37 - Why rebuilding the community he grew up in drove his early real estate bets

6:59 - What the Civitas model was built on and why distressed assets were hiding demand

8:07 - How DOMOS Co-Living came out of watching single people navigate shared apartments

11:29 - Being four days from non-contingent earnest money when his lender came back short

13:01 - Why Nectar had to be a technology company

15:39 - Running businesses with his wife since college and what makes it work

17:54 - Why he anchors his identity outside of the next success

19:52 - Keeping his personal life low leverage and cash flowing while taking big swings

21:26 - Why relationships matter more in the age of AI and advice for anyone starting out

Nectar | Nectar LinkedIn

Derrick Barker on LinkedIn

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Purpose-built student housing wasn't always an institutional asset class. When Jared was tracking the sector in college, two public companies dominated it and most developers hadn't touched it. His first deal in Syracuse required staking out an unresponsive seller on his morning commute just to get a conversation going — and delivered 40% net returns in 18 months when it sold to a publicly traded company.

From that first project, deal sizes have grown from $18 million to $100 million-plus, and the capital stack has evolved alongside them. What started with friends-and-family money has shifted toward institutional partnerships as the sector matured and larger players began paying attention. Aptitude has stayed ahead of that curve by sourcing deals directly, doing the heavy lifting on underwriting before ever approaching a capital partner, and being selective about the markets worth betting on.

In this episode of The Dealmakers' Edge, Aaron and Jared discuss how he broke into student housing before institutions cared about it, why large state schools are the only markets worth betting on long term, how to design buildings that hold up against 18-to-22-year-old tenants, and the mindset that keeps him steady through the volatility of development.

1:20 - Falling into real estate by accident and discovering entrepreneurship through development

7:19 - The eight-month pursuit of a seller that launched Aptitude’s first project

11:15 - The importance of disciplined land basis and refusing to “lie to yourself” in underwriting

13:58 - Scaling from friends-and-family capital to institutional partnerships

18:10 - The set-up of Aptitude’s executive team and launching an in-house management platform without team bloat

23:19 - Why student housing is operationally intense, but fundamentally durable, and designing for durability with 18-22 year old tenants

28:23 - Competition within the student housing asset class and why large state universities represent a long-term bet on enrollment stability

33:06 - Creating liquidity through quality construction and long-term market selection

34:19 - Jared’s resilient mindset for when things aren’t going well

Mentioned In Pioneering Student Housing and Scaling a Development Business with Jared Hutter

Aptitude Development | LinkedIn

Jared Hutter on LinkedIn

Enjoy the show? Have a guest in mind? Email us at podcast@aystrauss.com to let us know your feedback and who you want to hear on the next episode.

Connect with Aaron and the A.Y. Strauss team:

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Jeff Gronning is the CEO of Cannon Hill Capital Partners, a vertically integrated real estate private equity firm formed through a management-led buyout of the investment management business of Columbia Property Trust. Prior to founding Cannon Hill, Jeff served as Executive Vice President and Chief Investment Officer at Columbia Property Trust.

Before Columbia, Jeff spent 15 years at Normandy Real Estate Partners, where he co-led the growth of a vertically integrated real estate private equity firm. Prior to Normandy, he served as CFO of Morgan Stanley's real estate investing division.

Insights from Jeff Gronning on Capitalizing on Market Cycles in Commercial Real Estate

After 35 years navigating market cycles from the RTC era through the financial crisis and COVID, Jeff Gronning recognizes the current setup in office real estate. Values are down 40% to 70% from peak, and capital has been flowing away from the sector for years. In late 2025, his firm Cannon Hill Capital Partners announced a partnership with TriPost to acquire up to $1.5 billion in distressed office assets across the Northeast.

Jeff's conviction is rooted in what he's lived through before. When the financial crisis hit in 2008, he and his partners at Normandy Real Estate Partners had dry powder and capital markets expertise that allowed them to acquire assets like Boston's John Hancock Tower while the rest of the market stayed frozen. He believes this moment offers the kind of opportunity he hasn't seen in 15-plus years.

In this episode of The Dealmakers' Edge, Aaron and Jeff discuss what it takes to stay unflappable through multiple market cycles, why persistence and hard work matter more than timing, and what makes this moment feel like a generational opportunity in distressed office.

1:39 - Growing up in Northern Virginia and starting at Coopers & Lybrand during the RTC era

2:56 - Moving to Morgan Stanley and working on Real Estate Fund No. 1

4:44 - Leaving Morgan Stanley in 2005 to co-found Normandy Real Estate Partners

8:17 - Acquiring defaulted loans and controlling assets like John Hancock Tower

12:06 - Negotiating the Normandy-Columbia merger in late 2019 and closing in January 2020

13:13 - PIMCO's take-private transaction and navigating activist investors

15:24 - Spinning out 55 people to form Cannon Hill Capital Partners

17:12 - Announcing the TriPost Capital Partners strategic partnership in Q4 2025

18:25 - Office values down 40-70% and the opportunity in distressed office

20:19 - Three-part strategy: distressed debt, gap equity, and conversions

24:39 - Developing the mental edge to stay unflappable through market cycles

25:50 - Controlling what you can control and grinding through with persistence

Mentioned In Capitalizing on Market Cycles and Office Distress with Jeff Gronning

Cannon Hill Capital Partners | LinkedIn

Jeff Gronning on LinkedIn

Enjoy the show? Have a guest in mind? Email us at podcast@aystrauss.com to let us know your feedback and who you want to hear on the next episode.

Connect with Aaron and the A.Y. Strauss team:

• Our website (www.AYStrauss.com)
• Aaron's website bio page (Aaron's bio page)
• Aaron's LinkedIn account (LinkedIn)
• Our Twitter account (@AYStrauss)