Jeff Glass is the Cofounder and CEO of Hometap Equity Partners, a novel platform with $1 billion of investments alongside a mission to allow homeowners to access their home equity without having to sell, stress, or borrow. Jeff started the business eight years ago after a series of successes as an entrepreneur followed by seven years investing at Bain Capital Ventures.

Our conversation covers Jeff’s early lessons in sales, entrepreneurship, and investing that led to the founding of Hometap. We then discuss Hometap’s investment strategy, including the chicken-and-egg problem of starting the business, sourcing homeowners, sourcing capital, and developing the team, culture, and infrastructure that brings it all together.

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Jon Glidden is the CIO of Delta Air Lines, where he oversees the company’s $16 billion pension fund. Jon joined Delta in 2011, when the plan had $7.5 billion in assets, a $13 billion underfunded liability, and the highest actuarial expected rate of return (9%) of any company in the S&P 500. Despite funded status that threatened the solvency of the company thirteen years ago, investment performance combined with corporate contributions that offset plan payouts have improved Delta’s funding status from 42% to 102% today, creating the largest corporate pension turnaround in history.

Our conversation discusses Jon’s independent thinking and innovative approach that led to his incredible feat. We start with his Naval and investment background and then cover the four forces that drive his investment philosophy - portable alpha, private equity, portfolio construction, and governance - and the implementation of each.

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Chris and Rob Michalik are twin brothers and co-founders of Kinderhook Industries, a middle-market private equity firm overseeing $8 billion focused on healthcare services, environmental services, and the automotive aftermarket. Chris and Rob joined me on Private Equity Deals to discuss one of their portfolio companies, Ironclad Environmental Services, and that conversation is replayed in the feed.

This time around, we discuss their story attached at the hip. We cover their background and path to starting Kinderhook, including rooming together for the first 26 years of their lives. We discuss the firm's family-like culture, three pillars of its investment approach, unwarranted scrutiny of private equity in the healthcare sector, and the recent example of their purchase of Stewardship Medical Group out of the bankrupt Steward Healthcare.

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