In this episode of Shtark Tank, we sit down with Aleksey Chernobelskiy to discuss his fascinating journey—from his childhood in Moscow, his path to Torah observance, and his transition into the world of real estate investing. Aleksey shares insights into balancing idealism with reality, navigating the workforce as a Ben Torah, and his unconventional decision to turn down a spot at Cambridge in favor of Yeshiva.

Beyond his personal journey, Aleksey delves into the world of real estate investing, offering valuable perspectives on renting vs. buying, investment strategies, and the ethical challenges that come with managing other people’s money. He also talks about his growing online presence, the role of content creation in his career, and the ups and downs of being a public-facing figure in the digital age.

Some of the topics we covered:

• Growing up Jewish in Moscow – The challenges of Jewish life in the Soviet Union and why his family moved to the U.S.
• The journey to Torah observance – How a college campus organization introduced him to Yiddishkeit and led him to Yeshiva.
• Turning down Cambridge for Yeshiva – The difficult decision to forego a prestigious degree in favor of a life of Torah.
• Finding a balance between Torah and career – How he continues to navigate the tension between work and learning.
• The real estate industry – His transition into real estate investing, the advantages of the industry, and the risks involved.
• Rent vs. Buy debate – A detailed breakdown of the financial and emotional considerations of homeownership.
• Content creation and social media – How he built a following on LinkedIn and Twitter, the benefits of online branding, and the challenges of public visibility.
• Challenges of being a Baal Teshuva in the workforce – Adjusting from the Yeshiva environment back to the secular world while maintaining religious growth.
• Lightning Round: His favorite sefer for hashkafa, what he does on long Friday nights, and the dream career he never pursued.

💬 “If you’re proud to be Jewish, and you carry yourself with dignity, Hashem will take care of the rest.”

Biography: 

Aleksey Chernobelskiy advises limited partners (“LPs”) on existing and future investments. He’s also the founder of GP-LP Match, a platform which allows LPs to see deals that match their specific investment criteria right in their inbox immediately after a GP submission. Aleksey writes weekly to 7,000 investors at www.LPlessons.co to explain how to properly vet and think about LP investments in the grand scheme of their portfolios. Aleksey also helps General Partners on matters relating to LPs, such as capital calls or feedback on investment decks.

Prior to advising LPs, Aleksey ran STORE Capital’s $10 billion commercial real estate portfolio and oversaw the firm’s underwriting team. Aleksey graduated from University of Arizona with a quadruple major – Finance, Mathematics, Economics, and Accounting.

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Find Aleksey:

• LinkedIn
• X (Twitter)
• Weekly newsletter (LP Investing Lessons)

• Register for GP-LP Match

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