Blog by Jason Shuman / May 7, 2015

From Entrepreneur To VC…6 Observations From My First 60 Days

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Two months ago I was starting my 90 day fellowship at Corigin Ventures and wrote my first blog post “4 Reasons Why I’m Fired Up To Be A VC.” Today I’m proud to announce that I’ll be skipping the remaining month left in my fellowship to join Corigin Ventures full-time.

The past eight weeks have been a hectic time of learning, reflecting, meeting awesome people and a total lack of sleep. While the NYC tech community welcomed me with open arms I wish I enlistedGimlet Media to do the VC version of the Startup Podcast (if you don’t know what this is I recommend that you check it out!). However, since they didn’t, I’m using this outlet as a way to reflect on some key observations that I’ve made since joining the VC world.

Time Management is Critical — Time management as a VC is one of the most challenging adjustments. In theory you could spend every hour of the day meeting with new startups, but the question is whether or not that’s the best use of your time. I try to meet with as many people as I can (especially being in a new city), but I find myself having to book meetings a couple weeks out now. In order to be effective at my job, I’ve started to put aside regular time slots for reading, blogging and exercise. I’m also finding that the occasional Sunday at the office can be a good way to get away from email and focus on gaining a deeper understanding of markets, performing a great deal of due diligence or work on other projects for our portfolio companies.

Goal Setting is Challenging — If you’ve read any of my other blog posts then you know that I’m big into goal setting and your general state of mind. In startups it’s fairly easy to quantify you’re goals. The fact is that things in startups move so quickly that projects and deals get finished weekly. All of which is pretty quantifiable. However, one challenge I’ve recognized in Venture is quantifying your goals. The reality is that every week is different so while one week you may be focusing on deal sourcing and the number of meetings you take, the next week may be purely focused on closing a deal or making a hire for a portfolio company. Clearly defining these goals is a challenge, but a challenge which makes the job fun.

Conviction is Key — A few weeks ago I was in Boston at an Ask a VC panel where Rob Go from NextView described his firm by saying something along the lines of “we’re high conviction investors” (sorry if I’m paraphrasing, Rob). Truthfully, this struck a chord with me. In a positive way. The reason being is that in about 60 days I’ve worked on 2 deals that have closed, but “killed” over 50X that. Throughout that time I’ve felt varying levels of conviction when it comes to different teams, products and markets that I’ve come across. Without a doubt though I’ve felt the strongest levels of conviction with the investment theses I put together for our two recent investments.

With that said, it makes me curious as to what level of conviction Dave McClure has in each deal and how much it varies. Each firm has a completely different strategy, but I would be very interested to sit in on a conversation about this topic between the two of them.

VCs Talk. A Lot. — As a young entrepreneur I don’t think I understood the magnitude of how much VCs talk amongst themselves. From deal sourcing to due diligence, VCs are communicating with each other constantly. They form strong relationships with one another and it especially occurs at the associate level. As a result, I can completely see why some of the best firms today have been put together by former associates from a mixing pot of firms. And I can definitely imagine a few of my colleagues in NYC starting some firms that I’d love to be an investor in as well.

Entrepreneurs Need To Talk More — The bigger point that I’d prefer to make is that as much as VCs talk to each other about you, you should be talking to other entrepreneurs about the VCs. In my conversations with startups I try to be straight forward and transparent about what I perceive to be our strengths and weaknesses, and where we add value. I aim to provide them with specific examples of each and would urge them to followup with portfolio companies to see if we’re on the same page. If we’re properly managing our product as a VC then the portfolio company CEOs should agree. However, I don’t see Founders practicing this enough and I imagine that it has caused issues for venture backed companies for years.

I Miss Operating, But Enjoy Adding Value — It’s been an adjustment going from working on your own baby to now investing in someone else’s. I miss being in the trenches, but I enjoy helping a number of companies and meeting some inspirational founders. Since starting I’ve been able to work on Series A pitch decks, assist with hiring (and finding my friends jobs) and chime in on corporate strategies. Because of the lean team that we have at Corigin I get exposed to a great deal and that’s why it’s one of the best places that I could’ve asked to work at.

Everyday that I wake up I aim to learn something new and VC has certainly been providing me with that opportunity. I look forward to keeping everyone up to date on my journey in the VC world and want to thank everyone in the NY Tech scene that has welcomed me with open arms (and a free drink or two).

If you ever come across an interesting startup or want to talk startups, email me at or follow me on twitter @BoatShuman. I’d love to hear the thoughts of fellow VCs and those aspiring to become one.