The Tough Economics of Fashion vs. SaaS Scale

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.

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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