My guest today is Joanne Wilson, a New York City based angel investor, writer, podcaster, trend spotter, and self-described “woman around town.” Joanne has had a multifaceted and winding career, and began angel investing a decade ago when she put money into NYC-based media company Curbed media which we discuss in detail. Since then, she’s invested in more than 90 companies and been pitched by countless more. She is an instantly likeable person, you can literally tell in 10 seconds you are going to have a great conversation, so it’s no surprise that part of what makes her unique among angels is a very close relationship with many of the founders she backs. We cover a lot of ground. We talk about the personality traits of entrepreneurs, Joanne’s evolving investment style, her focus on female founders, fashion, business models, restaurants and a lot more. Please my conversation with the Gotham Gal, Joanne Wilson.   For more episodes go to InvestorFieldGuide.com/podcast. To get involved with Project Frontier, head to InvestorFieldGuide.com/frontier. Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub. Follow Patrick on Twitter at @patrick_oshag   Show Notes 2:12 - (First Question) – How does Joanne orient herself towards what’s new, in the context of food in New York city 4:10 – Can that mindset of forward thinking be cultivated 5:18 – Latest thing that got Joanne excited before everyone else 6:57 – Why the new frontier is going niche and local 10:23 – Joanne’s first investment 11:48 – Why do VC’s typically stay away from media 12:55 – How Joanne got into her first investment as a customer 14:11 – What is the skillset of making money that Joanne as 14:45 – Can you sense if a founder has that innate ability to just make money 17:04 – Are there common traits in founders 18:07 – Joanne’s progression into angel investing after her first investment 19:58 – Red flags when looking at investments 20:40 – Impression on growth without goals 23:30 – Trends among Joanne’s investments 25:56 – How much knowledge is transferrable between different industries that Joanne invests in 27:06 – The dichotomy and unique challenges between raising capital with female founders vs male founders 29:07 – How does Joanne balance her time and stay engaged with all of her investments 30:50 – Time when Joanne has helped a founder side step a pothole 31:35 – Most memorable first impression Joanne experienced 35:05 – How often does someone not have the right idea but is still worth investing in 37:19 – Why Joanne won’t start a fund 38:22 – Data on female founders returns and time 40:38 – Criteria for identifying emerging trends, especially in the more creative/artistic fields  43:29 – The changing costs of launching a brand, in the contest of fashion 47:11 – What has Joanne most excited right now       48:11 – Interesting facts about the fashion business  52:01 – Kindest thing anyone has done for Joanne   Learn More For more episodes go to InvestorFieldGuide.com/podcast.  Sign up for the book club, where you’ll get a full investor curriculum and then 3-4 suggestions every month at InvestorFieldGuide.com/bookclub Follow Patrick on twitter at @patrick_oshag