Angel Investing and Trend Spotting, w/ Joanne Wilson – [Invest Like the Best, EP.65]

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 enjoy my conversation with the Gotham Gal, Joanne Wilson.


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