Direct & Co-Investing for Family Offices with Randy Castleman

Randy Castleman advises family offices and institutional investors on their direct investing, fund investing, and fund formation. Years as a family office president, a managing GP of a venture fund, and allocating into privates for a large multifamily office give him a 360-degree view of private direct investing. Key Highlights:[00:01 -06:47] Opening SegmentIntroduction to Randy Castleman and how direct investing has changedHe shares his story of how he got started in family office managementHe was then hired at a large multifamily office to rip and replace their exposure to adventure and growth. His job is to work with families to discern their intention in doing deals, building intentional portfolios, and diversification  [06:48 - 16:01] Beyond Being TransactionalIt is essential to be open and honest about non-financial motivationsMany non-economic motivations don’t show up on questionnaires so it’s important to really ask questions and rephrase them when necessaryThere are unique advantages that family offices have within the direct investing spaceNot working within the same constraints that an institutional fund managerHuman nature such as messiness could sometimes be a disadvantage such as a lack of intentionality in portfolio building[16:02 - 33:52] How to De-risk the Disadvantages That Are Inherent within the Family Office Investing SpaceUnderstand the non-financial motivations and really talk through what you’re trying to accomplishStrategic versus Impact InvestingWhat financial returns am I looking for from this activity Consider the deal's lifecycle and its complete trajectory in the futureHave a sense of the behaviors of your co-investors[33:53 - 36:18] Integrate Best Practices without Undermining the DisadvantagesIf you develop your reputation for being good at a certain area amongst your co-investors, they will seek you outWhether a family office should have an in-house resource or not is half the battleYounger generations are more interested in direct investing.Advisors must be relevant and helpful not only to the current generation but to the next and the next[30:37 - 31:24] Closing SegmentConnect with Randy Castleman on LinkedIn, email him at [email protected], or visit www.srfmanagement.comKey Quote:“I think, along with an intentional portfolio comes an intentional look at any given opportunity.” - Randy Castleman“It's really important to think about the lifecycle of that deal, all the way to exit what sort of further investment will be necessary.” - Randy CastlemanLIKE, SUBSCRIBE, AND LEAVE US A REVIEW on Apple Podcasts, Spotify, Google Podcasts, or whatever platform you listen on. Thank you for tuning in and Stay Tuned for the Next Episode COMING SOON! Hosted on Acast. See acast.com/privacy for more information.