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About Gotham Gal:

Joanne Wilson, more frequently known as Gotham Gal, is a hugely successful angel investor, blogger, podcaster and feminist advocate who champions female founders and entrepreneurs to achieve their business goals. As well as an impressive investment portfolio, including 17 start-ups, Joanne is cofounder of the Women Entrepreneur Festival. She is a self-proclaimed ‘generalist’ in both business and everyday life: her career has spanned retail, wholesale, media technology and nonprofit leadership, as well as creating a wonderful life for her children and husband. Only in 2008, after encouragement from her husband, did Joanne take an interest in angel investing. Her first real investment, Curbed, was acquired by Vox Media in 2013 for between $20 to $30 million. As an unwavering success, Joanne is determined, passionate, and unapologetically confident, and serves as a prime role model for women and entrepreneurs looking to make a start. “Don’t wait” is one of her life mantras; a true philosophy to live by. 

In this podcast, she divulges a great deal into the secrets and surprises of investing and her personal life. As a professional, Joanne speaks highly of the founders she has encountered since embarking on her investment journey, as well as the best life hacks and advice to investors looking to start out. We also speak about the differences between male and female founders, and how that ultimately influences the business. The conversation ranges from the nitty-gritty aspects of an investor’s personal thesis to the best place to best in the West Village and the current state of democracy in the country. GothamGal is truly inspiring, and her effusive optimism and strength carried through in her voice. Listen to some of the rawest, real and motivating advice from one of the most forward thinkers in investing. 

Digest:

What is Gotham Gals background?

Joanne enlightens us on her childhood, her family, and what helped her get through such challenges so early on in her life. She links her childhood to who she has become today, in particular how she interacts with founders and behaves in business. Her situation growing up has made her “want to climb every mountain that came [her] way” and prove herself to others around her.

She also speaks about meeting her husband and family life. “Don’t wait,” she preaches, “nothing perfect.” Joanne surely advises female founders to have children when they want to, rather than putting their dreams of a family on hold to pursue their careers. She claims that the effects of being a younger mother are three-fold: you are in touch with your children’s generation, you have more stamina, and with a family and marriage you will become better founders and better managers. 

How did she get into and what was the biggest surprise about Angel Investing?

After assembling a hugely successful portfolio career in many different areas and setting up a family, Joanna decided to get back into business. Although she didn’t know what she wanted to do exactly, she had a clear idea of what she didn’t want to do: start a company or work for anyone. So, Angel Investing seemed to become more and more of a perfect option. Her husband was the final trigger, so she paired her knowledge of how to make money with her intuitive sense of how to build a business and started. Although ‘gut feeling’ is essential in investing, Joanne proclaims that “you never really know what’s going on, you might think you do, but you don’t.” Her life hack to getting to the root of who people are is founded on Malcolm Gladwell’s theory – if you meet enough people, and get an intuitive sense of their trust and reliability, you will just know. “Is this person tenacious enough? Are they in it for the long run?” are two questions that should always cross an investor’s mind. 

What are the key differences between male and female founders?

As a well-known investor into ‘female first’ companies, Joanne sheds some light on the differences she’s encountered between male and female founders. Females are more perfectionists, whereas men have “more swagger” and self-assurance that they will reach their goals. Joanne claims that the key, however, is to have both men and women around the table; they have different assets and viewpoints which work together to help a company thrive. “The perfect model is a male-female founder.’ An exploration of how to balance gender in companies, Joanne speaks about having to make a commitment to one’s personal thesis. She extends the example of Sweetums to show how making a company diverse on purpose can truly help it succeed.

To founders: what is one key piece of advice and what are the commonalities of success?

For Joanne, this one’s easy: “Don’t blow through the money.” Joanne provides expert insight into how to strike the right balance between being ‘clever’ and being ‘smart.’ It doesn’t happen overnight, she states, but you need to know how to build your company and have your foot on the gas at the same time. Timing is a key distinguishing factor of successful and unsuccessful founders: you need to know when to accelerate and when to exit. 

To investors: what do you look for and what advice would you new-comers to investing? 

As a vastly successful Angel Investor, there’s no better person to consult on making it in the investing work than Joanne. She speaks about how taking your time, doing in-depth research, finding and cultivating your personal thesis as well as understanding competition are all essential in making it in the investing world. When probed on whether market size or team comes first, Joanne doesn’t have a decisive answer; rather, she says it depends on what an investor is looking to get out of the investment. However, the key, she says, is that it’s all about the people.

Will Democracy prevail? 

Politics, the frontrunner of divisive topics, is brought up in conversation, and Joanne has a lot to say. To put it bluntly, her biggest fear is ‘the people running the country.’ Although she has hopes for the upcoming election, hopeful that “democracy will prevail”, Joanne speaks of the media, powermonger leadership, law and lawmakers, and the challenges of the government to know what’s going on in every corner of the administration. “You can’t sweep dust under a carpet, it will eventually come out.” 

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