Welcome to episode 29 of Offshoot. My guest today is Jack Cohen, a Managing Director of ArrowMark Partners, a Denver-based investment platform, and the founder of Dark Knight Ventures, Jack’s business consultancy, or “mentor capitalist” firm focused on helping smart, creative, salespeople be more successful. For Jack, it is a platform to teach and give away the things he’s learned on his journey as an intermediary, producer, principal, investor and consultant.
Jack’s main gig, if you will, was in my line of work. He took a single office mortgage banking business, Cohen Financial, from $200MM of annual loan production to 25 offices with $6B of annual production, and a loan servicing portfolio of over $30MM before a successful exit. Since then, he’s gotten on to a myriad of board and advisory positions while filling executive roles at some top-flight finance shops.
I heard Jack speak about 6 months ago and immediately knew I wanted to get to know him and perhaps get him on the podcast. I started by reading his book, was able to sit with him on a ski trip, and then again when he was in San Diego.
Jack’s the real deal. He’s hungry, he’s curious, he’s smart, he’s hard working, and he’s figured things out the old-fashioned way. He’s done the work and made the mistakes.
This is one of those podcasts that could have been twice as long. However, even in this short hour and a half, Jack drops a ton of knowledge and wisdom which is applicable across a wide swath of the industry.
Listen in as we cover topics that include:
“Stupid human tricks,” which Jack, in his self-deprecating fashion, labels his tools of the trade. They are lessons learned along the journey covering a myriad of scenarios.
The split between Jack and his father in growing the business with his father believing the business was to comprise “deal people and no one else that you need” while Jack operated from a leadership vantage point that meant accomplishing corporate goals through other’s work.
How the real estate business, and in particular the capital advisory business, is a to-do business, not a business to be outsmarted.
How not all strategy talk is in fact strategic rather it is people talking up their own playbook.
That standing for something, a why, is paramount to getting broad engagement from a team and how that provides common ground for people to rally from.
The idea that putting up one more success than failure, and getting up to try one more time, might be one great definition of success.
How you can be efficient with things but you need to be effective with people.
Why risk equals volatility of outcome and how smart investing chases excess return on a risk adjusted basis by identifying, assessing, mitigating, and pricing that risk.
Why many real estate assets have capital stacks with debt they can’t afford and will need to be repriced.
How a prudent operator or investor should seek deals, intermediaries, and collateral that they like before they engage in a transaction. If they don’t have all three, keep looking.
Why 2026 and 2027 might produce some of the best vintage of real estate deals in the last decade or so.
How self-awareness is the first step in the entrepreneurial journey which allows clarity and conviction to know how and why you are managing people and making decisions
Why bad experience comes from bad judgment and how that can lead to good outcomes.
Why fantasy is an important part of building a business.
Jack is a really great guy and he shares a boatload of wisdom in this, much of which can be revisited in his book, The Freedom Frameworks. For those that are curious, it’s a really solid book which I hope you take the time to read. Enjoy the podcast.
