Joanne Wilson — Gotham Gal

Wednesday, May 25, 2022
The Gotham Gal herself, Joanne Wilson, tells us that department stores are dead, but gives us a glimpse into the future and her own upcoming cannabis store that will pair your cannabis with your needs, mood and even the food you’re serving that night.
We also cover the state of VC today and much more.

It is a treat to have Joanne Wilson with me today.  Joanne, also known as the Gotham Gal, is an angel investor with probably many more than a hundred investments in her portfolio. She has a really impressive blog at She has her finger on the pulse of trends and she lives in New York, but winters in LA. So, I will take that as a strong LA endorsement.

Joanne, thanks for taking the time today.  So, fair to say that you’ve got your finger on the pulse?

I think that’s fair to say. And I actually think it might be innate.

Interesting. Where does that come from and how does that manifest itself?

I mean, I have this horrendous T-shirt that I bought years ago that I never wear outside of my house. It says, “I like what you liked five years ago”. You know, it’s interesting, even my grandmother was like really ahead of trends. My mother was always interested in trends. I think, because I’m a generalist, that if you read enough fodder, that’s like great for cocktail parties.

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And you sort of tied those dots together, you can see where things are coming down the line, you know, and now of course we have AI and we’ve got, much more ability to scrape the back ends of websites and get real data and to see where things are going. But, you know, it’s something I’ve always sort of this gut thing about.


I mean, it’s a great question. I mean, I think they should really be looking at the next generation of kids, you know, gen Z and what is coming down the pike and what are those kids interested? The one thing about a brand is you should be thinking of a brand as a living, breathing.

Thing that if you don’t continue to feed it and let it evolve, it dies. And so, you know, people use companies to help them come up with logos or, you have a team that works with someone outside. It’s just like, great. We build it. Well, great. That’s just your foundation. Right? You have to continue to feed that fire Do you have tools for how people can do that?

No. I know.

How do you see retail?

Mean, I’ve been in retail?

God, since I was 15 years old. And so you know, unfortunately I believe that when you looked at the big players in the eighties, federated, Macy’s, Neimans, all of them is they really. We’re able to hire the best and the brightest who were creative but also had good business minds.

And when the shit hit the fan and Campo got in the markets and everyone wanted to stop being public and become a private company and take on all that tremendous debt that they lost. That pipeline of really interesting next generation of people. And then along came the web. And then people gravitated towards that.

And so department stores, you know, in general, which I’ve always loved is that, you look at your numbers on Monday, you looked at your numbers on Tuesday, you look at your numbers out Wednesday and you can make immediate impact. , I do think we can apply that to the web as well. But department stores need to become.

Much more interactive, a different way. They show their merchandise not so generalized, much more singular eyes so that you’re just like a brand we’re gearing ourselves towards this particular customerAndmaybe seeing everything in the store they leave and it shows up at their door, but there has to be a real understanding that e-commerce is the best.

And that’s the best because it doesn’t have the cost of having a physical location.

That’s right. And it’s efficient.

So the reason people do e-commerce isn’t as much that they it. This is going to a store. They still want to go to the store, but they just want to make their lives more.

 And is it. fashion changing as well. So sort of the experience as well as the merchandise is evolving.

Yes, definitely. I mean, fast casual conceptually was a great idea because from a technology perspective, you go back into. Early nineties, right? If you were a buyer for let’s say Dillard’s and you wanted to buy 600 units, not a big deal, but if you had a small mom and pop store and you could only buy 36 units, That amount of time you would send with the 36 units.

First, the 600 ended up being more. But now, because of technology, you could buy. And the cost of making it doesn’t cost any more than 600 units or any less. And so fast, casual is great because if there’s an item and people react to it, you can quickly make these products, get them back into the stores and you have the technology so that you don’t have to have thousands and thousands and thousands of units, you can react to them.

Purchases versus having all this inventory, the next generation, which is out there loud and clear is not interested in Having 700 black shirts in their wardrobe, right. they care about the planet. Fashion is the worst when it comes to that, But. People are more casual people aren’t as stressed up. We’ll probably see a lot of bright colors in the spring because people are like, want a bus out.

But I don’t think that this next generation is interested like the gap where everyone wore the same shirt. Everyone wore the same jeans. It’s a lot more individualized, which is good for. Casual, but on the other hand, how do you create products for that like individual units? So maybe your store only has 12.

It’s an addition when it’s gone, it’s gone. And the other issue is if you do it that way, you’re not going to find yourself in the position of we sell everything and then we mark it down. The markdowns thing I’ve always hated. It’s like, if you see something, you like buying a full price and create a full price model.

We had, I don’t totally understand it. Why do you dislike marking it down from whose perspective?

both. I mean, you have a different customer that comes in your store and then really what you think you’re going to get for the garment in terms of your margins are different than what you are going to get for your stuff. And you’ve trained accustomed. Why buy now because it’s eventually going to be marked out.

And so I think with smaller additions, you have a better chance of people buying at full price, because if they miss nothing left,

Hm. You have such a different, I don’t do anything in fashion. So like you’re predicting that we’re all going to have bright colors. Love it.

I’m not, I will know where I’m black, but I do think we’re going to have,

So interesting. Yeah. Keep going. Anything else on the business of fashion that’s worth knowing,

I mean, it’s very similar to. Not celebrities. The same thing like in restaurants, Right.

Restaurants were making money for a very long time. When you’re paying someone to clean dishes for $15 an hour, it’s really hard to make money. But on the other hand, you want to pay someone $15 an hour to make dishes and make sure they have healthcare.

there needs to be a way to make higher profits in a restaurant. And I don’t think anyone has yet to figure that one out. But you can’t survive as a restaurant anymore on the rents that they’re charging, particularly in this.

I mean, there’s a number I think right. Of sort of the robotic arm puts your king wobble together.

Yes, I’m a big fan but I don’t know how that plays into the restaurant world. I mean, certainly for McDonald’s it works great.

 right. There’s something making the French fries all day long and it’s not a human being.

And are you thinking of opening a store? Do you have a store?

I am working on a store?

Oh, I’m so good. What is your store? Tell me more.

So I haven’t really talked about lab, but I will talk about it out loud. So I, it wasn’t, I came out of the retail world. Right. So in the training. Spectacular. and so, you know, I’ve always had this idea for a particular store. I mean, literally in college it was like part of this thesis I had of a store.

And. I’ve never done it. And so with the changing of the cannabis laws in New York, I’m actually applying for three cannabis licenses. You can only get three to open three separate stores that will not only carry cannabis uh, products that will be from bowties. Operators within New York state but also a concept shop that is tied to cannabis.

So it could be, vintage ashtrays. It could be great streetwear. It could be a whole selection of coal cactuses, you know, as we drill down on what exactly the customer is and what we’re selling.

So. I am a big believer in cannabis becoming more.

a part of the community. And when you create a store like that, you can versus, you know, you go up to Massachusetts where most of the stores literally are just plastic buckets of weed. When you walk in the door and people look like they’re standing outside, waiting for their social security check like that, isn’t a good look.

And so we need to change the narrative. Just like you would walk into a wine store and say, you know, this is kind of what I’m looking for. This is what I’m eating tonight. And so, we want to be the premier store for people that can feel that with the products we are selling to them are the products that they feel good about.

I also feel like people in cannabis shop very differently. And I think a lot is influenced by the establishment. Like you walk in and someone says, smell this one. You’re like, yeah, it smells great.

Yeah, exactly. But it really is brand.


Very similar to the fashion world. Right. So I think you’ll see at one point smaller brands let’s say in California would be one person. Like there wasn’t the fashion world. It’d be like, I represent these eight brands. And so I’m selling them to these dispensary’s thinking of the year to come.

We’re going to see a massive wash out of a lot of brands because you can only do them state by state. And so you have to really have an operational bandwidth and have partners in other states to create those products, make sure the same in New York as they are in LA, even though someone else’s manufacturing them and using your recipe.

So you started by saying you had all this training in the fashion business, what is some of that training that you’re bringing here?

Well, certainly, I mean, I started out in. They’re the one thing was cool about Macy’s in the day

was you went in, you know, three months training program, which is the right amount of time to find the bathroom. And then they put you into a store as a store manager of a particular vertical based on what they thought you were capable. And I ended up going out to King’s Plaza, Brooklyn, and I was the manager for the cosmetic department, which was the number one cosmetic department outside of Herald square. And you know, as 150 women working for me, I was 21 years old. I always had good instinct for business and how to make money, and so I went into every single person that ran all the different cosmetics from. Clinique to Estee Lauder to whatever it was. And we went through every single case line and got rid of all the old inventory, had all the old people that represent it, take it back, learned how to turn our inventory so that we were making more money and make everyone feel that they had ownership in their particular cosmetic space.

So I loved managing.

And I love figuring out how to make the bottom line go up. And so that was an incredible experience. And then I went into assistant buying. It’s a very different experience. How you make your department profitable across at that point 16 and then eventually 28 stores. and I found being a buyer extremely boring, and I was ready to move up to the next job, which is running a store, which I would have loved. But I was told that women don’t move as quickly as men. And then I was like, I’m out of here. And that was the.

Wow. . , and did that catalyze, you sort of blazing this trail with your focus on empowering women?

Yeah. I think that the big takeaway when I quit Macy’s, and I had had. Impactful career within the organization. I was known and to say I quit

was scary,

but once I quit, once I realized, oh my God, I can quit again. And so I. A variety of different jobs over the course of a couple of years in the other side, which is the garment district. And once I filled my knowledge, I quit and I went on to the next, so I could fill my brain with more stuff. And so, you know, these businesses they’re down and dirty, but they’re really simplistic.

It’s you know how much you make, what’s the markup? How quickly do you turn the merchandise? And where’s the merchandise going, what’s coming down the pike. And if you can kind of have the perfect storm on that, when

. And do you, you know,, when you bleed that into your investing career, are you now drawn towards fashion or cosmetics or certain areas more than others

no, because I know too much.

right. Okay. Because you can see where they’re not thinking about it correctly or something. When someone comes pitches you.


I mean, even in the cannabis space, when I was like, this is going somewhere, you know, six or seven years ago, I really want to start investing in this stuff. And I found the, most of the people that were behind it were such Cowboys. You know, they saw an opportunity, but they really didn’t know how to run a business. And so I didn’t make as many investments as I thought I would just. Nothing came across my desk that I thought was worthy of my time.

. And did you enter cannabis? in part because of sort of a philosophy around the potential benefits to our society and wanting to sort of make it more mainstream

Well, that, that is actually one of the reasons. I mean, listen, I’ve been getting stoned pretty often since eighth grade. Right? I mean, when I had children, of course I stopped for awhile because I think it was something I should be doing when I was getting pregnant. But I will say even back then, I thought this is eventually going to become a legal cause.

It’s so stupid that it’s not. you know, we’ve allowed pharma to take over and take over our children in schools. And so they’re thinking other ways that maybe it would make more sense and be not as. overwhelming to put kids or anyone on the same freaking drug. Right. So I do think in the years to come, we’ll be able to take your, your undertake, your blood and say, this is the dosage for you.

and I think we can do that with any type of drug, . Well, that is exciting. So these stores are coming soon to New York.


and we have a whole social mission around it because that’s very important, which is , it would be profit sharing for everyone. Um, We’re also committed to hiring people out of nature, which is New York city’s public housing where 15% of the people in New York live. We’re also committed to hiring people that have been in jail.

Yeah. I’m selfishly like, sorry. It’s not happening in LA. Yeah.


Let me ask a question. Can you talk to me a little about like the different, almost style culture, like how you see the differences between the two cities? Cause you spent a lot of time in both.

Yes I do. Um, You know, it’s funny, I’ve never figured out. Style in LA. I’m still working on it, but um, you know, New York, I dress up every day. I mean, not dress up, like, you.

know, wear a suit, but like I definitely have a look going on. Right. . I put myself together every day, So I think it’s really important. I think LA is a much more casual town.

And depending on what side of the city you live in,

um, Depends on how late you stay up. But someone described LA to my husband, which is. In LA, you get up, you have your juice, you take your walk, you take your time for lunch, and then you end the day early, you have dinner and then, you know, you might have a glass of wine.

You go to bed in New York, you get up, you have your coffee, you work out, you go, go, go, you know, and all day long, your meetings all day, then you move that into dinner meetings. Or maybe you go to the theater or maybe you go to some live performance and you drink. And then. All night and you like roll into bed at like midnight, and then you wake up in the morning and do it all over again.

Yeah. Okay. Do you think that applies to the tech venture sort of style as well?

I think every city is doing. In terms of the tech venture,

I’ve found the LA community to be extremely embracive and thoughtful and helpful. And actually much more intimate. Right. Because when I started investing in LA, it reminded me of what it was like in New York in 2005. New York is just much larger.

I can see that. What is your view right now of tech and venture? When I started doing angel investing, which was very much a generalist, I thought that it was a very nascent business because. All of a sudden you can build a company on top of a platform for not a lot of money and the valuations were in line with what they were worth at that time or what they wanted to raise. Right.

So if you wanted to raise a million dollars, your post valuation should be $5 million and that’s fair. Because. That’s where you are. I think what’s happened is so many people have jumped into the tech VC world. The one thing that I find very frustrating is . Everyone is like jumping on these hot deals, like, and they happen overnight. And there’s not this ability to meet the founder and really take time to flush this through because like everyone wants to steal. but to come to someone who is a um, angel and say, You know, we’re, starting our seed round and our valuation is $20 million. It’s just like, oh, Hey, I’m at, And so I think that a lot of this has been pushed from a Y Combinator,

 And it’s not pretty Yeah. It is Hedy times. What about just adding value? Like what you were talking about actually adding value. What do you think? You know, the good VCs. VCs, , what have you seen in the board rooms?

The good VCs is if you open up their doors and really peel back the onion, you will see that they didn’t make money on one company. They made money on. 80% of their companies and the ones that fail, they figured out a way. To merge them in another company or get everyone to get a job. Right. They really care about all of them.

 Whereas the bad VC. That might own 10% of the company don’t do shit. Many of them send the associates.

So they never show for the board meetings. They only show once a month and they ask questions and poke holes, but they don’t give advice and how they get there.

And I have been very frustrated with some of the really bad VCs. I mean, also a really good VC, not only understands how to manage their portfolio from a financial perspective but also have a really good gut impact of what company.

Make sense. And our billing voids in markets that will be essential three or four or five years from now, whereas bad VCs, regardless of understanding financials, many of them just don’t have a gut for picking the right businesses. What’s amazing to me is they keep getting funded, you know, it’s mindblowing.

You know what goes up, goes down. And we’ve had certainly a long time of up and we’re all I’m, you know, is based on what’s going on today, over in Russia is like, I think everyone is., chewing their nails and wondering, like what’s going to happen to the markets. You know, why were we spending more time building alternative energies.

I mean, Russia is essentially a gas station,

Yeah. That’s a whole nother tangent, as you think about all +our portfolio companies with developers and teams in

Oh my God.

in Russia,

Yes.It’s very scary. it really is scary. and shame on our GOP for continuing to use crisises for political purposes. And you know, we got some bad stuff going on here too. I don’t know if you’re watching the show. I just started watching last night called 1883.


Oh, my God. So it’s basically what it was like in 1880.


hit all the high notes. It was a fricking cowboy show, people killing each other. There was no government, there was no law. It was an awful way to live. , and you think about what’s going on now where people want no government, no law lies and all those things. Um, It really sorta hits home of like, Well, that’s what the reality is. Like we should really think about what it is we’re looking for.

So without having seen the show, another big difference, I think is just the role of business. we have these huge global companies I’m really curious what you think. The business community. Should be doing and, you know, do we have a much bigger role now than we did even a few decades ago?

Yes, absolutely. And by the way, The other people that have a big role are successful founders

who have made insane amount of money. Like why are we going to Mars?

 Same question every time.

Right. I mean, how about we live? our feet are on this ground.


have all this fucking money, it could be towards cancer. It could be towards whatever it may be.

Give it a way, make a change in society. Aren’t we all responsible for that?

Why do you think. Miss that, whether it’s business leaders or founders or vendor or whatever, why do you think aren’t feeling the same way that you and I are feeling


you think.

IGA. I mean, I haven’t seen a woman trying to get to.

And do you think there’s a way to change the ego? I mean, I’m not just about getting to Mars, but like Having more impact. I feel like people aren’t as motivated as they ought to be.

And I don’t know why they’re not. I mean, most of them came from nothing.


I mean, at one point, how much do you need.

. Yeah. I mean, , okay, different question. You also have done a fair amount of media, right?

I’m super curious how you see news evolving

it’s so awful. It’s so awful shame on the media, but get it because the media’s business model is pretty fricking center. Advertising an eyeballs.

So Yeah.

we do have a responsibility to Share the truth and not be cited like Fox media.

I mean, they’ve definitely taken them out of the British media and they should take them out here. I mean, if you spend any time watching Fox, it’s just like, Then you think, okay, well maybe they’re lying. Maybe near cons is line, may wash them like where, where is the truth?

I mean, someone told me an amazing story is their father first-generation Korean came over here. The kids were all first generation live in Texas. It was a major dog. And very, you know, socially responsible, left Democrat. And all of a sudden he started like talking like a lunatic about all this stuff. And one of the kids said, check dad’s Facebook feed.

And sure enough, there it all was. They played around with all the settings and he returned to normal.

I didn’t realize also, did you say like in the UK that they’ve taken out sort of the

Yeah. Yeah. they’ve Stopped them. I think it’s not from printing or maybe it’s from air media, but yeah, they have stopped that.

. Okay. Let’s shift gears. I, cause I don’t have a solution on that one.

I don’t either, but it is really, really disturbing. And, you know, I know there’s a lot of new media things being launched, but shame, shame on all of the media for how they have amplified bullshit instead of reality.

Well, everyone’s dying unless they continue to innovate. right.

Which is what you’re investing in, which is outsiders. So are we going to fix all of our problems in climate. Yes. we have to fix that.

and we will, because it will be coming from outside. It won’t happen inside just like department stores. If they’re about to die, they’re all gonna die and we’ll have a new way because that’s what the greatest part of capitalism is.

Is that. You can create newness. You can change industries there is a constant cycle for the old goes out and the new comes back.

you’re a great speaker. You’re a really good podcast guest. I was just going to let you finish that code. Cause I was like, it’s such a good quote. Okay. I want to talk about you. I wanted to ask them about your inflection points. Like when did Fred become Fred and was that like, I’m

curious whether that was actually hard in some ways or whether that affected your career.


I mean, listen, I, was making three times as much as Fred,

And allowed him to go to graduate school then came back, got married. We had children. Boatloads of money at a young age, he was making shifts and he went into venture you know, and then there was the kids and changing or whatever, have you not, and like all of a sudden, like he became this fret, you know, and I always laugh.

I was like, wait a second. I was supposed to be Fred Wilson. Like, how did that happen? Right. I assumed I was gonna run a multi-billion dollar company and take over the world. And he was obviously. And the hammered with that and drawn to it. And so and he’ll say if it wasn’t, for me, he’d probably still be at the original venture capital fund.

You know, because I was like, no, you’re worth more. You gotta move on. You should start you’re on for her, you know?

but if you weren’t married to him, you would be Joanne Wilson. Like you would be a big figure on your own, but because you’re married to him, like he’s a better known name. I think, you know what I mean?

No he is. Yes.


for him. I mean,

it’s Because of where I come from and my upbringing, it was really hard for a long time. But we’ve always been partners. I’ve always been involved in everything he’s been invested in or what have you, not in the backend. And vice versa with tremendous respect for each other. And so there was a point in my life where I was like, you know, get out of my way.

Like I can do it just as good as everyone else. But I don’t feel that way anymore because I find little. Understood or acknowledged my own personal successes.

Yeah, I think I’ve heard you say in other contexts, you just don’t give a shit

No, I mean, I’ve always been a rule breaker. Right. You know, always. and so his friends, but he’s more. Pragmatic in some ways. And I think that for men, many of them, they start here and then they just slowly move up where women, because. We have children find that they have a very up-down up-down up-down career.

And um, you know, now, you know, we had our children young, which makes a big difference. And so, you know, we can do a lot of businesses together which is really nice, but yeah, there was definitely times where it’s been difficult, but I don’t think either of us think of each other.

Even in the public sphere is like, you know, Fred Wilson or whatever. You know what I mean? that’s not who we are.

Well, you live together. I

mean, you know, of course you don’t, but to other people who like read your writing or read his writing, you have a personality, like, It is still a big deal.

Right, but to us, it’s not

Of course, it’s not, you eat dinner with each other all the time. I mean, how did you, like, I don’t know if this is a fair question.

How did you get to the point where you speak with such confidence about things? You have this sort of, don’t give a shit persona. How did you get there? Like I want to get there more.

I want more. women to be there.

I really think it came down to growing up in a household with a extremely smart father and mother, but my father. Menza type stuff. And and he’s an absolute asshole.

And I think because of that,

And, and in a narcissist to boot that I was just like, you know, he didn’t make any of us feel that we were as smart or as important as him

and I was like wrong.

 And so I think that’s where some of that.

But now I feel like reading your blog. I feel like you, you lead a really good life. That was my summary. Reading your



Yeah, it was like good food, good conversation, Sundance skiing. what I saw.

Yeah. Yeah, no, we do live a great life, but we also work hard and play hard. And we have instilled that in our three children.

You know, and it is harder raising three children when we didn’t grow up with anything, you know, financially. And now you have these three kids who I have a very different outlook on the world because they have the ability to be anything they want to be, because they don’t have to worry about paying the rent.

Right. That’s not always helpful though. I mean, not criticizing your children just generally.

It’s not, but, you know, I think that we have been honest from day one and transparent with our children about what we have and just because you have doesn’t mean you should. And you, should work hard and you should play hard. And I think they all do that really well.

that’s wonderful.

Yeah. Well doing, I mean, congratulations. I feel like congratulations on leading a good life and doing meaningful work. And best of luck with your stores,

I’m really excited. .

Well, thanks for coming on the podcast today.Well, thank you now. This is great.