Why This 28-Year-Old Executive Left Square To Become A Venture Capitalist http://www.businessinsider.com/jared-fliesler-square-matrix-partners-2013-3/comments en-us Wed, 31 Dec 1969 19:00:00 -0500 Sat, 27 Dec 2014 12:17:08 -0500 Owen Thomas http://www.businessinsider.com/c/5139a8ffecad04e06f00000f Charlie Fri, 08 Mar 2013 04:01:51 -0500 http://www.businessinsider.com/c/5139a8ffecad04e06f00000f Hey Owen, in your Rabois is "Silicon Valley's hottest commodity" piece, why did you mark my constructive comment questioning the objectivity of your piece offensive and then backdate a reply to the parent comment about keeping things constructive after the fact? This is very unprofessional. Do you have a relationship to Rabois, Fliesler, et al. that you need to disclose? You saw fit to run with my second comment on that piece about ownership stakes (which I left a few minutes after my first comment that you pulled your backdating shenanigans on) and produced subsequent pieces about Square's updated Alaska filings indicating new ownership stakes. You seem to be doing a lot of cheerleading for Rabois and company (Techcrunch is guilty of this as well). Perhaps you have a relationship with the crisis management firm that Square hired? For example, in this piece, you state that no actual lawsuit has been filed almost as if to exonerate Rabois. What happened to the alleged victim who has been thoroughly scrubbed from Square? What were the terms of his severance? We're obviously not going to get the full story, but Rabois seems to be getting a pass on this because he is a semi important Silicon Valley guy who is friends with a lot of people and knows how to run an effective PR campaign. http://www.businessinsider.com/c/5139148fecad04e65f000003 RozzSummer Thu, 07 Mar 2013 17:28:31 -0500 http://www.businessinsider.com/c/5139148fecad04e65f000003 I wish Fliesler good luck in his new career as a VC. However, I think he's in for a few really big surprises: 1) Partnerships are nothing like startups. Every large venture firm has a political environment so thick it can be cut with a knife. The agendas at play are far more complex and non-intuitive than in any corporate environment, large or small. Nothing makes me believe Matrix is any different. Jarad will quickly either adapt or get quickly washed out on that dimension alone. 2) If he is truly an Investment Partner, where his vote counts on making (or not) an investment, he'll find that his position comes with a level of overhead he's likely never experienced before: Writing investment memos, detailed financial analyses and scenarios, rounding up support in the partnership to do a deal (and agreeing to do other deals to get Partners' support on his, even if he doesn't truly like the investment thesis of the deal he has to support), dealing with internal partnership reporting (quarterly reports to LPs, portfolio reviews, etc), learning how to deftly handle LPs with lots of probing questions about the portfolio, and managing infamous "Monday Morning Partnership Meetings", which can easily (and usually) devolve into esoteric debates with those with history in the firm. Before long, he'll begin questioning his own abilities and talents. Recognize those meetings for what they are and stay focused. 3) It's impossible to dive as deeply in every deal he does as much as he desires to. The focus he had at Slide was a privilege not afforded a VC. There are far too many potential deals to review, too many 1st meetings he'll need to sit through (and as a junior partner it will be a large number of them), too many interviews to do for executives in his companies, all while making sure he's carving out his own brand and expertise while the senior partners ask him ("ask", but translated it's "go do") to help dig them out of the hole their in on troubled deals. 4) It's easy to believe that being a VC gives wide latitude in allocating funds to growing companies and access to vast amounts of cash allows making decisions that force a great outcomes. Unfortunately, that can only be said of the senior partners in the firm. Jarad will be put on a very short leash relative to investment size and risk. My advice to him: double the amount of cash you think you need to get to the milestones needed in each deal, and double it again when you argue for holding reserve capital for follow-on funding rounds in each of your deals. 5) At the end of the day, LPs don't care what great company you built, or how much effort you put into getting a base hit or a home run. In fact, they don't generally care if you invest in panty hose factories as long as you deliver great returns. Further advice: Don't ever forget that. I wish you good luck Jarad, but my sense is you'll find far more satisfaction doing the next Slide than being a great VC. Peace.