Real Talk: Real Estate Discussions with Andrew Kirsh

Episode 86 (January 21, 2026):

From Music Executive to Multifamily CEO with Larry Jacobson

Episode Overview

In this episode, Andrew Kirsh sits down with Larry Jacobson, President & CEO of Jacobson Equities, to delve into his unique journey from music industry executive to successful owner-operator in the multifamily real estate space. They explore the transferable skills between two seemingly disparate industries, Jacobson’s transition into the family real estate business, lessons learned from both sectors, current market dynamics, and guidance for aspiring real estate professionals. The episode also offers personal insights, memorable music biz stories, candid market perspectives, and a lighthearted "lightning round" on sports, music, and TV.

Larry Jacobson’s Career Journey: From Law to Music to Real Estate

Early Career and Legal Foundations

• Larry started as a real estate lawyer at a major firm in the late 1980s (03:48).
• Quickly realized he was unfulfilled by law, despite bringing in business and receiving top bonuses.
• “As a third-year lawyer, if you had a killer year, next year you couldn't be a seventh-year lawyer... I thought that was really limiting.” — Larry Jacobson (04:41)

Spark for the Music Business

• Epiphany while listening to Faith No More on the freeway: “Nothing that I was going to do that day was going to make me feel the way that song made me feel. And I've always loved music… It was just in my soul.” — Larry Jacobson (05:16)
• Leveraged connections (notably his sister, Nina Jacobson, later a Hollywood producer) to break into the industry.
• Accepted a 45% pay cut to become the #2 lawyer at Giant Records (07:05).

Climbing in Music: Deals, Creativity, and Management

• Landed his first major break by securing the Dazed and Confused soundtrack for a bargain, leading to commercial success (08:28).
  • “It ended up going multi platinum... one of the most classic soundtracks in the music business history.” — Larry Jacobson (09:06)
• Transitioned into broader creative and business roles; eventually became partner at Giant Records and helped sign/break major acts like Disturbed (10:12).
• Later managed Avenged Sevenfold from discovery to global success (12:39), as well as other major artists: Alanis Morissette, Michael Bolton, Slash.
  • “That band has sold 10 or 11 million records, multiple number ones. One of the biggest touring acts in the world.” — Larry Jacobson on Avenged Sevenfold (14:05)
• Balanced artist management with legal acumen, eventually realizing he only wanted to manage select acts.

Pivot to Real Estate & Family Business

• Took over family real estate business in the wake of his father's illness (16:40).
• Previous experience managing and lawyering on family properties since law school days (15:18).
• Emphasizes the value of trust and reputation, especially in real estate syndication.
  • “Your most valuable currency as a sponsor...is trust.” — Larry Jacobson (17:30)

Lessons from Two Industries & Career Transitions

Transferable Skills and Mindset

• Structured deal-making and risk assessment are common ground between entertainment and real estate (18:53).
• “In essence, it’s about making deals. It’s about strategy…The similarities are greater than people might think.” — Larry Jacobson (19:41)
• Emphasizes the importance of ethical operations and protecting clients/investors/artists.

Family Business and Modernization

• Took over in June 2012, modernizing systems and investor relations (22:31).
• Worked to reassure longtime investors and expand geographic reach beyond California.

Real Estate Investment Strategy & Market Insights

Expansion Beyond California

• Jacobson Equities now invests across the U.S., moving into student housing and select Sunbelt/Pacific Northwest markets (25:19).
• Entered student housing unexpectedly via a deal in Chico, CA; philosophy was to learn from the best on-site teams (27:10).

Student Housing Approach

• Focuses on:
  • Proximity to major universities (Power 4 schools)
  • Affordable rather than ultra-premium properties
  • Targeting walkable, supply-constrained markets

Portfolio Reflections: What Works in California

• Notable surprise: Despite regulatory perception, best-performing assets (rent growth, occupancy, collections) remain in select California markets (29:51).
• “California buildings don’t have headaches right now. If you know where to buy.” — Larry Jacobson (33:03)
• Avoids cities with hyper-restrictive rent control but sees value where development is suppressed and demand is steady.

Regulatory Risk and Market Nuance

• Evaluates California’s state rent control versus unpredictable local regulations (35:01).
• Highlights that every market (e.g., Denver, Dallas) harbors its own blend of risks, from oversupply to regulatory changes.
  • “No market is perfect. Essentially, all we’re doing is trying to underrate the individual risks.” — Larry Jacobson (37:28)
• Current acquisition strategy is favoring California’s unique supply constraints.

Capital Sourcing & Syndication

• Traditional syndication remains core, with an eye toward institutional JV for larger deals (39:01).
• “We believe right now we’re in a very good place to source off-market opportunities...that will be appealing to institutions and everything else, we’re going to syndicate.” — Larry Jacobson (41:37)
• Newly hired team members with off-market access expected to drive new pipeline.

Market Outlook: Deal Velocity & Interest Rates

• Sees increased deal velocity ahead due to funds needing to exit or recycle capital, as well as necessary bank action on troubled loans (43:04).
• “I don’t think anybody really knows... So our attitude is you just roll up your sleeves, you just work harder, you uncover more rocks and you kiss more toads.” — Larry Jacobson (44:03)

Memorable Quotes & Moments

• On leaving law for music:

  “I drove down the 10, got on the 110... and I decided I was no longer a real estate lawyer. I was getting into the music business.” — Larry Jacobson (06:18)

• On career risk:

  “My mother said, ‘I’ve never seen so many people ecstatic over a guy that just took a 45% pay cut.’” — Larry Jacobson (07:05)

• On trust in real estate:

  “When people trust you, that’s really your most valuable currency as a sponsor.” — Larry Jacobson (17:30)

• On dealmaking similarity:

  “In essence, it’s about making deals... The similarities [between music and real estate] are greater than people might think.” — Larry Jacobson (19:41)

• On current CA market:

  “California buildings don’t have headaches right now. If you know where to buy.” — Larry Jacobson (33:03)

Notable Timestamps & Topics

• 03:48 — Larry’s early law career & why legal path felt limiting
• 05:16 — Life-changing moment inspired by music
• 07:05 — Move to Giant Records, pay cut, and parental reactions
• 09:06 — Dazed and Confused soundtrack deal
• 10:12 — Transition to executive/creative roles, signing Disturbed
• 12:39 — Serendipitous meeting with Avenged Sevenfold
• 15:18 — Early taste of family real estate business
• 16:40 — Full transition into real estate after father's illness
• 19:41 — Parallels between music business and real estate
• 25:19 — Geographic expansion from CA and move into student housing
• 29:51 — Reflection: CA assets consistently outperforming
• 33:03–34:27 — California's regulatory landscape and asset durability
• 37:28 — Market risks and current focus on CA
• 39:01 — Fundraising model: syndication versus institutional capital
• 41:37 — Leveraging off-market relationships for acquisitions
• 43:04–44:03 — 2026 market outlook, more deals coming, importance of persistence

Real Talk Lightning Round Highlights (45:07–58:09)

• Best golf course: North Berwick, Scotland (45:34)
• Best concert attended: Rolling Stones & Guns N’ Roses, LA Coliseum (46:50); Nirvana at the Palace before they were famous (47:12)
• Current favorite TV: Landman (49:04)
• Dream new real estate markets: Nashville, Salt Lake City, more student housing at large flagship universities (53:55)
• Biggest music regret/shift: Admits to mostly listening to classic rock these days despite career in younger acts (48:19)
• Dodger playoff emotions: Both host and guest joke about their intense fandom and playoff stress (52:14)
• Advice for new grads:

  “It’s about who you work for first. Associate yourself with somebody with the gray hair... In real life, you’re supposed to be educated by what people who are successful... have done and learn from them.” — Larry Jacobson (55:42)

Practical Advice for Aspiring Real Estate Professionals

• Seek mentorship from industry veterans with experience and strong ethics.
• Don’t rush into entrepreneurship; learn from the “giants” first.
• Stay humble and keep learning—never be afraid to ask peers for advice. (56:09–57:13)
• “In real life, you’re supposed to be educated by what people who are successful, who’ve achieved things, have done and learn from them. And it never ends.” — Larry Jacobson (56:09)

Episode Tone & Style

The conversation is candid, humorous, and authentic, filled with insider anecdotes and relatable career advice. Larry Jacobson is reflective about his unconventional path, openly shares lessons from both success and adversity, and offers a pragmatic, ethical lens on current and future real estate challenges. Andrew keeps the discussion lively and grounded, allowing the episode to resonate with both industry veterans and newcomers.

Listen for:

• Unique parallels between high-level music management and real estate investment
• Behind-the-scenes stories of A-list music acts
• Candid reflections on market cycles and what’s ahead
• Actionable tips for building a trustworthy career in real estate