Raising money is hard for a bunch of reasons. You have to clearly articulate your vision for a business that may be non-obvious. You will invariably suck at this at the beginning, and need to do it many times to distill the just-right way of communicating your profound message succinctly. And once you nail that, you will almost certainly need to deliver this pitch dozens of times to find the right investors to partner with who share the same passion for the vision that you do. …


Much has been written about how to start a venture firm, how to raise money from LPs, how to build one’s product and reputation and how to invest. Precious little has been written about how to return value to LPs and the venture firm/CEO dynamics associated with this process. This is one of those areas that while there isn’t a “right” answer, I believe the question subjects itself to a rigorous thought process and decision trees that are well-articulated and robustly debated. I recently shared some thoughts on the topic.

And I later added some more nuanced observations on…


It has taken some time for me to get used to Major League Baseball circa 2020. I’ve seen dozens of games cancelled hours before the first pitch, loads of (utterly predictable) injuries decimate teams and empty stadiums with piped in sounds that seem almost dystopian relative to our previous non-pandemic world. That all said, I’ve also witnessed some beautiful and unexpected things that have arisen from this odd, stilted season thus far. 7-inning games with loads of doubleheaders has added rapid fire action and strategic nuance like never before. Amazing performances from players who would still be deep on the…


Just minutes ago the MLB Players Association (PA)just voted down the owner’s last offer to resurrect the already tortured 2020 season. This will predictably lead to the MLB imposing a shortened schedule, some players opting out of playing at all, the PA filing a grievance against the league and the upcoming free agent class getting mauled. We’ve reached the point where there is nary an intersection in the Venn Diagram of each party’s requirements, with the likely result being a shotgun marriage of two reluctant participants merely adhering to the words of a contract. As a negotiator, this is absolutely…


I love baseball and have my entire life. Baseball has played a massive role in my family culture and in our community through having raised two accomplished baseball players, coaching our sons’ Little League teams for years and through leadership in and evangelism for the sport. Professionally I’ve had nothing to do with baseball: the first half of my career was spent in trading and senior management on Wall Street, while for the past 15 years I’ve been investing in and enabling brilliant founders to build ethical, impactful, fast-growing technology companies. These businesses now employ many thousands of people globally…


Quite simply, the decision as to whether or not there will be Major League Baseball in 2020 turns on the following facts:

Fact 1: Games paid (for) is a function of games played. This means prorated salaries. Players have contracts and are creditors. Owners own teams and enjoy the risks and rewards of the equity. The obligation is clear: the owners owe prorated salaries to the players.

Fact 2: Owners care less about regular season games than the playoffs for monetary reasons. This is why they’re happy offering proration on a 50 game season because of the value of playoffs…


If the MLB owners hadn’t gotten rich in whatever field enabled them to buy a baseball team, they could all start their own PR firms — or be politicians. Reading the cries of poverty by multi-billionaire owners around short-term cash flow issues leaves me cold. But somehow, some way, they get mainstream media to go along with the notion that pandemic-induced cash flow problems are the players’ problem, and that the players have to be the ones to bridge a large share of the cash flow gap suffered by the clubs in 2020. So, in rough times, you effectively ask…


Since the MLBPA does such a poor job communicating the nature of the players’ relationship with the MLB to the pubic, let me take a crack at it. As mentioned in my first article on the current conflict, the players almost always lose to the owners in the court of public opinion, substantially hampering their negotiating position. Why?

  • Most baseball fans don’t understand the restrictive nature of the Uniform Player’s Contract, as well as the terms in the Collective Bargaining Agreement dealing with issues of service time (remember Kris Bryant?) …


Let me start by saying that I don’t know Tony Clark. I enjoyed watching him play ball and have heard he’s a really good guy. But what I do know is that the MLBPA, as a tactical matter, has been on a slippery slope for quite some time and it’s only getting worse. It’s easy to get caught up in the emotions of what’s going on between the owners and the players: I mean, who doesn’t wan’t (read: NEED) the beautiful game of baseball to be played safely and in short order. But what I want or need isn’t really…


In the past few days I’ve shared some thoughts about the motives of the owners and the MLB Players Association as well as the dynamics of their positioning in the negotiations. Today’s piece is perhaps the most important as it deals with the most critical aspect of any constructive negotiation: trust. And trust is in short order today, perhaps more so than at any time in the recent past. But I’ve personally lived through the crushing work stoppages of 1981 and 1994, which I do not want to see replicated at a time when we need the love and the…

Roger Ehrenberg

managing partner @iaventures. working @thetradedeskinc @transferwise @signifyd @octanelending @memsql @robinhealthco @ethyca_. alumnus @UMich @Columbia_Biz

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