E358: Joanne Wilson, Co-Founder Womens’ Entrepreneur Festival, Blogger, Angel Investor

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Joanne “The Gotham Gal” Wilson joins Jason for a trip down memory lane and discussion about her female founder powered investments.

Show our guests some love!

http://twitter.com/thegothamgal
http://www.gothamgal.com

3:30:00 What was the first company you invested in?
3:45:00 What was it about that business & entrepreneur to make you invest?
5:15:00 How do you decide to invest in a first-time entrepreneur?
8:00:00 What are the biggest mistakes entrepreneurs make in the beginning?
10:30:00 Why did you invest in Mouth.com?
12:30:00 Do you think the Indie food movement is a national trend?
15:00:00 How do you get the entrepreneur to the next level with new personnel?
15:45:00 What are you investing in now?
17:15:00 What do you think about Bloomberg’s move on the food industry?
18:30:00 How has the industry changed since the Silicon Alley days?
20:30:00 This episode is made possible by New Relic
24:15:00 Why are you investing in so many female founders?
25:15:00 Do you think male investors have a bias toward funding female founders?
27:00:00 Do you think they up their game because other expect them to fail?
28:30:00 Do you think female entrepreneurs are higher performaning than men?
29:00:00 Do you think women take as much risk?
31:45:00 Why is Kitchensurfing a good business?
34:30:00 How did you find out about ScootNetworks?
35:30:00 How’s Food52 doing?
36:00:00 How did you get involved in MOUSE?
38:15:00 What were the highlights of MOUSE?
41:15:00 What’s your thoughts on the NYC school system?
43:00:00 This episode is brought to you by SquareSpace.
46:00:00 Are you going to start a proper Angel fund?
47:00:00 What is your conference about?
47:30:00 What do you think tips a woman into entrepreneurship?
49:15:00 What is the key to balancing a family and a career?
52:15:00 What do you look for in an entrepreneur?
54:45:00 What did that business pivot to?
55:30:00 Everyone follow @thegothamgal

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Full Transcript

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TWiST title sequence.

Jason: Hey, everybody. Welcome to This is ThisWeekIn Startups. The program where we talk about making a dent in the universe, creating companies, being a founder, investing in these companies. With me today, Joanne Wilson, the Gotham Gal herself, who I’ve known for 20 years, who helped me build my first business, who literally when I rang the cash register for the first time she was the one who did it, really helped me jumpstart my career. One of my oldest friends. Now angel investor in over 30 companies. Welcome to the program Joanne Wilson.

Joanne: Thank you.

Jason: God we have a long history.

Joanne: I know. It’s crazy. Actually I was thinking about this morning, before I got here, was about how when you, Josh Harris, me and Fred sat around our table and did that podcast.

Jason: Oh yeah. When you guys were doing the Wilson Family Podcast, like 10 years ago.

Joanne: Exactly.

Jason: When podcasting first started you guys were doing your own podcast. For people who don’t know you and I worked together on Silicon Alley Reporter back in the 90s. I was a snot nosed little bratty kid and you were my pit bull salesperson who just built the entire company. Boy did we have a fun time together.

Joanne: We did have a fun time. It was great.

Jason: This was at the dawn of the internet era.

Joanne: Yep.

Jason: Just when it started, 96-97.

Joanne: Yes. You were schlepping around five pieces of paper stapled together and you were going to write about this world that was going to happen.

Jason: The internet.

Joanne: Yes.

Jason: You had 3 kids.

Joanne: Yes.

Jason: You were a stay at home mom at the time.

Joanne: Yeah. I had three kids. I think Josh was like…

Jason: 2 or 3?

Joanne: No. Josh was like 4 months old.

Jason: Yeah.

Joanne: That’s when I lost it. I was like, “I cannot do this. I need to…”

Jason: Work.

Joanne: “I need to use my brain.”

Jason: I remember the day you showed up at Josh Harris’ loft, I was doing an event, Ready Set Pitch. You came and… I had talked to your husband, Fred Wilson, the famous venture capitalist who at the time wasn’t very famous. We were friends. Listen. He was a venture capitalist in New York.

Joanne: Right.

Jason: Which was kind of like a joke. You’re venture capitalist in New York.

Joanne: That’s right. He made his mark and said, “I’m going to invest between downtown and 96th street. FDR and the westside highway.”

Jason: Yeah. Which at the time was pretty radical considering there were no companies at the time worth investing in the footprint.

Joanne: No.

Jason: But boy did that work out for him. A lot of huge hits.

Joanne: Yes.

Jason: We’ve worked together for a number of years. But putting that aside, some time ago, 5 or 6 years ago you started angel investing. The first company you angel invested in?

Joanne: Curbed Media.

Jason: Curbed.com of course, Curbed Media.

Joanne: Curbed.com. So Curbed, Rack and Eater.

Jason: Run by a tremendous entrepreneur who’s been on the program twice, Lockhart Steele.

Joanne: Yes.

Jason: You’ve always been a foodie I know that. We’ve shared many great meals together and you’ve given me great recommendations. What was it about that entrepreneur and that business that made you want to… I think you were one of the first angel investors.

Joanne: You know, I had sort of been watching what was going on in the next generation of the web, right? Which to me was a hell of a lot more exciting than the first generation. As we all knew. Watch them all implode or…

Jason: Flame out.

Joanne: … flame out or whatever they did. But they’re gone.

Jason: Yeah.

Joanne: I’d been watching Lockhart from afar and I had been an avid reader of all the sites. I saw him in an event that we went to and I talked to him. I said, “I’ve been watching your sites whatever.” I love what he was doing. At home, of course, I was talking about all the new companies that I was seeing out there. Fred had come home one day… I had actually spoke to Nick Denton as well.

Jason: Yeah.

Joanne: He said, “I heard Lock is looking for money.” I was like, “Really?” Fred said, “You should invest.” I was like, “Seriously?” He said, “You would be great at this.” I was like, “Alright.” I called Lock, I got together and I put money in and that was it.

Jason: Of course Curbed covers real estate, food, everything.

Joanne: And shopping.

Jason: Shopping. Right. Eater, Racked and Curbed. He had worked previously at Gawker. But when you invested in him… still kind of an unproven entrepreneur. That was his first company himself.

Joanne: Oh. Totally.

Jason: So how do you get past, when your looking at a first time entrepreneur, investing in them or not? How do you know they’re going to make it or not or they have a reasonable chance?

Joanne: You assume they’ll get better as you go along, right? But I think that… For me it’s all gut. You just know. First of all you have to like the business. Then, of course, you have to think the entrepreneur is going to be able to execute on this vision and not be so stuck on that exact vision. Because these companies evolve into something so completely different over time that if your not open to that you’re never going to move forward. I really like Lock. I felt that what he was building was the future of how we’re going to consume content.

Jason: Right. Which is short bite sized but very insidery. He hires really knowledgeable people.

Joanne: Yeah. And it’s very snarky which I like. I think that’s one thing, at the level I’m investing in, is these things take time.

Jason: Yeah. You have to have patience.

Joanne: You have to have a lot of patience. Now I see angels that are involved get very frustrated. Like, “Oh my God. Now they’re raising this much. They haven’t really done this much yet.” It’s just like, you gotta believe and you have to be supportive of the entrepreneurs in a positive way not in a negative way. It does nobody any good being negative. Of course, unless things turn sour. In general I think also you have to be a bit of a cheerleader and their sort of den mother.

Jason: It’s hard enough as it is then to have your investors, who are supposed to be your cheerleaders, breathing down your neck about stuff.

Joanne: Yes.

Jason: If you did pick the person then you’ve already decided this is your spouse or this is your friend.

Joanne: Yeah. You’re married to these people.

Jason: You’re married so you might as well just love them for who they are.

Joanne: Yeah. I totally agree.

Jason: There’s no use picking somebody and then being bitter about it.

Joanne: No. It does not make any sense.

Jason: I picked you as a spouse and now I’m going to hate you.

Joanne: Exactly. There’s a fine line between love and hate.

Jason: Right.

Joanne: But I think it’s important as an entrepreneur to have some investors that are totally passive. Then a few that are engaged that can really help you move forward. It’s like having a great doubles game. You get together every 4-6 weeks. I actually force all of them to do that.

Jason: Wow.

Joanne: To sit around a table with the right people and talk about where you’re going, get out of the weeds, have a plan, what makes sense, who are you going to hire, where’s the money going to go. So even though I’m a generalist in the way I invest all of them have the same exact issues. building the foundation is no different really. It’s just different content.

Jason: What do you think the keys are? What do entrepreneurs need to get done that first year? Cause that’s when you get in there, the first or second year. In that very nascent state what are the things that people mess up the most and don’t focus on enough that then comes back to get them?

Joanne: I think one of the things people do is they get excited they have all this money and they think they can go wild, right? That is a big mistake. That’s a huge mistake. That’s number one.

Jason: They just start spending on Arian chairs or space or things that don’t matter.

Joanne: No. They spend money on too many people.

Jason: Ahh.

Joanne: You got to where you got because you were scrappy. Still be scrappy.

Jason: Ah. So they just start hiring because they think they can throw bodies at problems.

Joanne: Yeah. I even see companies that are pretty mature that I think, “What are all these people doing here.”

Jason: Right.

Joanne: Isn’t the point of building all these technology companies to be lean and mean machines?

Jason: Right.

Joanne: But whatever. I think that is number one. People do that. I think the second thing is that in the beginning you hire a bunch of people and then you realize, wow, I actually can now have a little more professional people. I actually know better what I need to do. So you have to make those tough decisions, moving people around, getting rid of the dead wood.

Jason: Right.

Joanne: I think now one of the most important things that I say to all the companies I invested in, “Figure out how you’re going to make money.”

Jason: Yeah.

Joanne: You gotta make revenues and you got to have engagement. If you can figure out how to make money sooner than later and you can cover your nut you get a longer runway. The longer your runway the more you grow the company and the better your valuation becomes and that’s good for everybody.

Jason: Everything starts working out. Less dilution. Curbed really did figure out one thing early, just in the selection process, real estate has a huge transaction size. The advertisers are brokers.

Joanne: Yes.

Jason: When they sell a home they make $100K or more here in New York City, at least, and in LA and San Francisco, certainly. So they just had this built-in endemic advertising base that was extraordinary.

Joanne: Yeah. Well the other thing is that what they have done is they’ve created a platform for the business model. So every architect, every real estate developer, every real estate broker reads it and so do people who are just interested in what’s happening in the real estate world.

Jason: Right.

Joanne: The same thing in Racked and the same thing in Eater. So it’s a B2B platform but it’s a B2C platform too. Which I think is really rare.

Jason: A B2B2C.

Joanne: Exactly. It’s sort of like Silicon Alley Reporter had a little bit of that. You had some people who were sort of consumers of technology then a lot of people who were in the business of it. Let’s talk about Mouth. We both invested in that, Craig Kanarick. Am I pronouncing that right?

Joanne: Yeah. And Sam Murray.

Jason: Yeah. New York Mouth. But they announced today actually of all days that they’re going to be Mouth.com.

Joanne: Yeah. Today is the day.

Jason: Today’s the day. Fantastic. Tell us about that business and why you invested in it.

Joanne: That is an interesting business. I first met with Craig and Sam… I love those guys. First of all they’re gray hair, they’ve both built businesses.

Jason: Razorfish, a huge business.

Joanne: Razorfish. Sam actually has built a serious family business that he ended up selling. So these guys know how to build a business and they know how to run an operation.

Jason: So you like a little gray hair?

Joanne: I like a little gray hair. I also like that Craig is the creative and Sam is the operator, right?

Jason: So some balance between the founders?

Joanne: There’s a total balance between the founders. I know that there are other businesses that have come before them that have been debacles in the same space. But I think they actually understand that timing in life is everything.

Jason: What is the space? Then how does it…

Joanne: Well you can’t drop ship. You have to actually buy the food and package it intelligently. You have to be a commerce store in a brick and mortar way online.

Jason: So Mouth is selling… To people who don’t know.

Joanne: Indie food. From the best beef jerky to the best hot sauces to the best chocolates. There about to get, I believe, their liquor license.

Jason: Wow.

Joanne: Which is going to be a huge score. Which is one of the things I said at the very beginning, “You guys gotta get a liquor license.” I mean that’s a marketing phenomena.

Jason: Right. That’s something that came out of one of your rap sessions with them? Or just hanging out saying, “Hey. Where are we going to take this business?”

Joanne: Yeah.

Jason: Liquor is just so clear.

Joanne: Liquor is so clear.

Jason: In California at least. Can you ship in New York?

Joanne: You can. You need a brick and mortar store in order to ship. Certainly, certain states you can’t ship to. But the liquor laws are changing. I mean you can see that they’re changing because everyone is making these small products. These tiny distilleries are popping up. So they’re only popping up because the laws are changing.

Jason: Got it. Do you think the indie food movement is something that’s like a national trend? You know, it took a little while for Whole Foods to make its way outside of the major cities. It does seem like they’re having Whole Foods in every major city across the United States. Do you think this is something that will make its way to Milwaukee or Detroit or Florida?

Joanne: I think it’s already in those cities. Absolutely not even a question.

Jason: Right.

Joanne: I think this next generation is very interested in doing things that they love. Being a cobbler, being a pickle maker, being a chocolatier. You know, making t-shirts right. Things that they really care about. People kind of going back to their roots.

Jason: Yeah.

Joanne: Then with the whole… you know, people getting sick and bad things happening. Our food laws are a disaster. We basically make products based on 1930 or 1940 laws. I think that there are a lot of people saying, “I want to know what I’m eating.”

Jason: And who made it.

Joanne: “And who made it. I want to support local merchants that are making things that taste good that are providing income for them and I know what’s coming into my body.”

Jason: Yeah. So Mouth.com is the site. I’m an investor in it too, full disclosure. People just go crazy for this product.

Joanne: People stay on that thing for like… 10 minutes is the average engagement. It’s amazing.

Jason: They just hang out on the site forever.

Joanne: You hang out. Cause you’re like, “Oh, my God. This is so good. This is so good. This is so good.”

Jason: The chocolate is ridiculous isn’t it?

Joanne: Yeah. The best is to go there Friday cause Friday is tasting day.

Jason: Oh. At their offices?

Joanne: At their offices.

Jason: Oh wow.

Joanne: Oh yes.

Jason: So they inventory this stuff.

Joanne: They inventory it.

Jason: Wow.

Joanne: They were down in South Carolina, I think it was. They met this guy who had taken red peppers and extracted it and made this incredible hot sauce. He had made 250 jars. They’re like, “We’ll take them all.” Cause this guy’s never going to ship, right?

Jason: Right.

Joanne: You want something to come in a beautiful bag, great marketing and that’s your product, right?

Jason: Right.

Joanne: You don’t want something coming from 19 different locations and the one guy who’s shipping the pepper sauce is like, “Yeah. I’m going to get to it today.”

Jason: Yeah.

Joanne: It doesn’t work.

Jason: It doesn’t work. So you were talking earlier about staffing and sort of upgrading staff being a hard thing. How do you get entrepreneurs to do that really hard decision to like… The people who got us here are not the ones who are going to get us there, to the next level. We may need to fire them or give them a boss. How do you have that discussion with the entrepreneurs who are, I think, sometimes pig headedly loyal to the people who got them there. Rightfully so, right?

Joanne: Rightfully so. I think that all of them are pretty savvy and pretty smart and know what they want. They want their dreams to come true, right? As painful as it is they do it. I remember one entrepreneur I had. I missed the board meeting. I don’t know why I couldn’t make it or whatever. So I talked to her like 3 days later. I said, “I just want to know what happened in the meeting.” She said, “Well everyone says my burn rate is too high.” “So what’s your burn rate?” I said, “It is too high. You need to cut about $70K a month off of that thing.”

Jason: Yeah.

Joanne: She goes, “They say I should do this and this.” I said, “Tomorrow. You fire those people tomorrow.”

Jason: Right.

Joanne: You know. It was painful but once you do it…

Jason: Yeah. Take the medicine.

Joanne: … you’re an adult.

Jason: Yeah. It’s not easy but the life of the business is more important than the feelings of a couple of individuals. Or your feelings even.

Joanne: That’s right.

Jason: You have to transcend that.

Joanne: It’s all about how you tell the message, right?

Jason: Yeah. What else have you invested in recently, previously.

Joanne: Recently I have a couple that are in the pipeline. I just invested in a company called Mercaris.

Jason: Mercaris. What is it?

Joanne: A really smart entrepreneur woman down in DC. She is basically building a commodities site for the organic and non-GMO market. It’s a $31B business marketplace today. We can only imagine where it’s going to go.

Jason: Organic and non-GMO.

Joanne: So no…

Jason: Genetically Modified Products.

Joanne: Right. So there is no marketplace. So if you are Whole Foods and you have to go out and buy a thousand pounds of organic flour because your making organic cupcakes at your stores what price do you lock into? Who’s making this stuff? Where are you getting it from? I mean there’s literally no up to date daily information on this stuff.

Jason: No infrastructure.

Joanne: None.

Jason: Yeah. The laws… We almost passed in California a… You have to label GMO food. Just like in Europe. I guess they banned it.

Joanne: Yeah.

Jason: In some places it’s been banned or you have to label it at least.

Joanne: I’m sure we’re going to get there.

Jason: New York seems to have done an amazing job around food. What do you think of what Bloomberg’s done in terms of like forcing calories, banning Big Gulps, all this kind of stuff?

Joanne: I think it’s a great idea.

Jason: Yeah.

Joanne: Honestly, I’d sign up for him for another 4 years.

Jason: Another 50?

Joanne: Exactly. I think that’s how most people feel. I mean…

Jason: Mayor King.

Joanne: Mayor King. Listen. We’re obviously a very democratic city. I think that sometimes in a democratic city it’s great to have a republican mayor because they’re pushing issues through that actually create a better financial workplace.

Jason: Right.

Joanne: He’s done a great job. I mean the city is in great shape. He has given everyone these incredibly long leashes to build communities and companies. I think that has been a real mash behind the tech industry in New York City.

Jason: Compare Silicon Alley 1.0 and 2.0 now. I mean it’s a massive transformation. Obviously we worked together during the first one when just starting a company in New York was like a handicap. It seems to be an advantage these days.

Joanne: It was costly.

Jason: Costly, a handicap. Like there was no support system in place today.

Joanne: No there wasn’t. I was the support system.

Jason: Exactly. You were. Silicon Alley Reporter.

Joanne: … support system. Everyone calls like, “I’m starting a business. Who should I use as a lawyer and who should I use as an accountant?”

Jason: Right. It’s like 3 people. Jay Rand…

Joanne: Jay Rand who I still use. He’s still my lawyer. I love Jay. You know, I think one of the things that has changed is, obviously, it’s not as expensive to start a business, right? We are such a unique city that as technology moves forward every industry can be and will be changed and disrupted. Even though I hate the word disruption. I’m so over it. But essentially…

Jason: Yeah. Reinvented, disrupted.

Joanne: Reinvented, right? So you’ve got media, you’ve got hospitals, health care, you’ve got fashion, you have… Now we’re starting to make products here again. So you have all these different industries and you have all these people in the tech industry changing each of those industries individually. So they sit in this really strange place. On one hand they’re in that particular industry they’re changing but on the other hand they’re in the tech community. There is support from both sides of the fence because everyone knows that the future is gong to be very different than the way we use any of those products today.

Jason: Yeah. In New York talent seems to be at an all time high. A lot of people leaving San Francisco to start companies in New York. Codecademy is here. Union Square is a backer of them. They went to Y Combinator then they came back to house themselves here. A lot of startups…

Joanne: Wouldn’t you want to live here?

Jason: Of course. It’s the best city in the world.

Joanne: It’s the best city in the world. So there you go.

Jason: A lot of people just moving back.

Joanne: I mean. I don’t understand why you would want to live out there.

Jason: Yeah. San Francisco is kind of a rough place… It’s kind of one dimensional compared to New York I think.

Joanne: I agree.

Jason: Hey. When we get back from the commercial break I want to talk about female founders.

Joanne: OK.

Jason: Everybody talks about funding them. You’re actually doing it. I want to get an idea of… God how do you… I gotta be really politically correct because I’m a guy. But how is this changing? Are we seeing more more female founders actually starting. Cause it seems that a lot of them don’t even start. How is that changing in the marketplace. When we get back from this very important commercial break.

Jason: What a great episode of ThisWeekIn Startups we’re having. This episode is made possible by my friends at New Relic. They are absolutely crushing it. What a great startup. There doing fantastic as a company. I’ve heard all kinds of great things from people in the business community about them. We use them here for their amazing web and mobile app monitoring. It makes all of our real-time applications faster and more seamless. You can see here. Here’s the browser load time. I can see, at different points in time, how my web app is doing. I see the Memcache is taking a long time. Maybe the database or Ruby. What is taking time with my app? As you know speed is the best feature you can add to any web app. Stability is the best features of any piece of software. If you can add stability and speed and constantly work on that and have that transparency inside your organization you’re going to win and you’re going to win big as an internet company. So you want to monitor the real user experience, as you can see there. You’re also going to want to monitor things like the servers and and exactly what’s taking time there. You know, I hate to say this in a negative way but you need to know who to blame when things are not going well. Is it your developer, is it your co-location facility, is it your hosting company, is it your CDN? Are you out of memory? Is it Ruby? What the hell’s going on on your server and how do you optimize that? It’s critical for you to know that. We use it here for the Launch Ticker and for ThisWeekIn Startups. We get these great emails. These emails go to the whole staff. So we can see… Oh my God. We’ve got 10K views this week. Well that’s a pretty good week. We see… Oh my God. Our uptime was 100%. Fantastic. I look at the views and the uptime cause that’s very… and the error rate is just .03, it’s nothing. Which is very normal. Our uptime was 100% everyday. Our load time was about 5 seconds a page. We have very big pages with a lot of images. So that’s the full-on load time. Then our responsive time… Just really good to see the error rate and the CPU utilization is like 1%. That’s great. Plenty of memory and the database is doing fine. All those things let us check off, “Hey. We don’t need to add more service.” But, hey, at some point the database might start grinding, page loads may take longer. You say, “You know, we need to get this database going.” You want to trust your service. Just like SkullCandy, Spotify, Nike, Zillow and Vonage have to our friends at New Relic. They do a great job. So many people who’ve been on the program say that they use New Relic. They made a great t-shirt. One of our fans designed this very cool t-shirt. If you create a free account over there by going to newrelic.com/twist and you sign up for an account, which is super easy and fast, with no credit card, you can get that TWiST shirt. So again, please go to newrelic.com/twist. Developers across the spectrum trust the critical performance of their apps to New Relic and you should to. Everybody thank @newrelic on their Twitter account. I personally thank you guys over at New Relic. I really appreciate it… and gals… for supporting the program. Let’s get back to this great interview.

Jason: Welcome back. I’m here with Joanne Wilson, massively prolific angel investor. 35 investments, Curbed, Mouth.com and many others, Food52. A bunch of them. Female entrepreneurs, female founders… Gosh. I remember in web 1.0 we saw none of them. Like there were one or two. There was this weird like… Oh my God. There’s a female founder. You had your Meg Whitman’s or your professional CEOs who were brought in the later stages but you never saw a female founder like starting something. So rare. iVillage being one of the few exceptions. Geraldine Laybourne, I guess. But today a lot more and you’re investing in them. Why are you investing in so many disproportionately to the percentage of women who are starting businesses?

Joanne; Well, I started blogging 10 years ago.

Jason: Gotham Gal.

Joanne: Gotham Gal. I started blogging because I didn’t want to lose my cred in the industry, of course. But what happened is the industry changed.

Jason: Right.

Joanne: So all these people I thought was going to continue, sort of, faded into the woodwork. So what I talk about… Actually somebody said this to me this morning… She says, “You know I love reading you because I know who you are. It’s like you’re talking to me, we’re having a conversation. I’m following you on the path to your life.”

Jason: Right.

Joanne: So it resonated with females.

Jason: Right.

Joanne: All of a sudden I started hearing from all these female entrepreneurs. First there was one then there was a second. I kind of became this chick magnet. The theme was constant. Which was, “Nobody wants to fund me.”

Jason: Interesting. Do you think there’s a bias by the male VCs and male angel investors to look at a female founder and say, “Probably not going to go at it as hard as male founder?”

Joanne: I think it is a subconscious decision. Yes.

Jason: So consciously they don’t think they have bias…

Joanne: But they do.

Jason: But they do.

Joanne: They absolutely do. Some of the comments that come out of their mouth is shocking.

Jason: Really?

Joanne: Oh, yeah.

Jason: Share. Not with the specific… don’t tell me who said it.

Joanne: I will not tell you who said it.

Jason: Please.

Joanne: Here’s one. “So you’re married. Are you going to get pregnant? Because I really don’t want to invest in someone who’s going to have a kid.” “So this is really a good business. I think it’s amazing what you’ve built but you know what? You’ll probably exit at $30M so I’ll never get my money out.”

Jason: Right.

Joanne: These are the types of conversations. “Oh. Is there a guy in there. I want to talk about… Do you have spending habit problems? I want to make sure you’re spending the money right.” Really? I built this.

Jason: So they basically, in their mind, think women are going to do it for some period of time until they start making babies. Then it’s over.

Joanne: Or whatever it is.

Jason: Yeah.

Joanne: Right. But the funny thing is… I’m invested in men and women.

Jason: Right.

Joanne: … is that women cross their t’s and dots their i’s. Which is a good thing and a bad thing. But I will tell you if you look at the statistics about success those women, every single one that I’m invested in, failure is not an option for them. They don’t care if it’s a longer runway to get there. They will make it happen. They listen and they calculate and they analyze and they are interested only in success.

Jason: Do you think they’re upping their game because they know the spotlight’s on them, they know that people are discounting them?

Joanne: No. I think they’re upping their game because they’re passionate about what they’re doing.

Jason: Yeah.

Joanne: Listen. There’s not even a question that there are companies that I’ve invested in that I believe will be $50M companies, others that will be $200M companies and others could be a $1B company, right? But the reality is that VCs invest in companies… and they’ll tell you, “We’re only interested in investing in companies that we believe will be a billion dollars.” The truth is they invest in a lot of companies that end up exiting at $50M-$100M.

Jason: Right.

Joanne: So you never know where they’re going to end up. That billion dollar business could be so poorly executed on that it ends up being worth nothing. So as these women start building their businesses and they actually have traction and they are making money I believe that they will have a lot more people looking at them on their next go round. No this one.

Jason: Interesting. So maybe they’re not as… Maybe the market today is this unconscious bias. Where there was outright bias previously.

Joanne: Oh yeah.

Jason: I mean there were VCs who say, “I just don’t invest in women. Why would you do that?” Now it’s sort of like, “Of course I’ll invest in women,” with some slight bias. You’re actually attracted to them… Do you think that they are actually higher performers than men right now?

Joanne: I’ve not loss one yet.

Jason: Interesting. So maybe there is. Do you think they have more diligence in how they perform? A little bit?

Joanne: Yeah. I do.

Jason: A little more diligent?

Joanne: You know what? They’re not as cocky and they’re not sort of like highfalutin. Like, “I can do anything. I need this valuation. I’m going to get this. I know what I’m doing.” Even though they don’t know what they’re doing.

Jason: So the ego thing with men… I think sometimes people like the ego of like the brash CEO. But a lot of times that just sends you way off track.

Joanne: You know, it depends on the person on the other side of the table.

Jason: Right.

Joanne: I would like to see more women be a little cockier.

Jason: Interesting. Do you think that they’re not leaning in enough as much or just not taking as much risk?

Joanne: I don’t think it’s risk. I just think it’s how they present themselves.

Jason: Ah. More muted, you think? Or understated?

Joanne: I just think a little more calculating, you know. Not so free willing and not so like, “Yo. I built this thing. If you don’t like it I’m out of here.”

Jason: Yeah. They gotta be a little more aggressive in that regard.

Joanne: I think they should be. But they become that way after they start trying to get people to give them money. Once, all of a sudden, they’re out there looking for money and they see, “Wow. We doubled our business this month.” Like they start to get a lot more confident when they go out and get money.

Jason: I think that’s probably part of the role that you play. LIke, “Hey. Let’s make the numbers go up.” Then things get pretty confident. When we worked together you took the revenue of Silicon Alley Reporter from $10K a month to $100K in 6 months. I became a cocky guy. I was like, “My business is doing great.” No, but it’s true.

Joanne: It changes everything.

Jason: It changes everything.

Joanne: That’s right.

Jason: But people don’t seem to focus on the fact that. In fact your husband, Fred, who is a good friend of mine and investor in my company… Actually you’re an investor in my company. You’re an angel investor.

Joanne: I am an investor in your company.

Jason: The Wilson are investors in Inside.com. Famously known as Mahalo.com. I’ll give you an update on that later. He’s kind of a swing for the fences, don’t worry about revenue guy. You guys are kind of opposite in that approach.

Joanne: Yeah. But I also think that that a time, right? I mean there was a time when the entire conversation was like, “If you get the eyeballs we’ll figure it out.”

Jason: Right.

Joanne: If you grow your business big enough and you have this many people that are engaging it’s going to be worth something. We’ll figure it out.

Jason: Which is true. Yeah.

Joanne: I think now the businesses that are being built, from helping large companies do a better job of what they’re doing, whatever it may be, I don’t think… People really, really have to understand what eyeballs are going to translate into revenue.

Jason: Yeah. So a Tumblr with a lot of consumers and 12-15 year olds is going to get a lot of eyeballs in order to monetize. They seem to have done that successfully.

Joanne: Yeah.

Jason: But for somebody who’s doing ecommerce or software as a service those eyeballs are worth a magnitude more.

Joanne: Yeah. I think a lot of the businesses that he’s looking at going forward are not so like, “I don’t care about the revenue model.”

Jason: Tell me about Kitchen Surfing. That one to me is fascinating.

Joanne: It’s a great business.

Jason: Tell me. Why? What is it?

Joanne: Chris Muscarella is the entrepreneur behind that. Very calculating, very smart guy. Even calculating in who he wanted his investors to be on the first round.

Jason: Very good. That’s always a good sign, isn’t it, when they care about who’s giving them the money.

Joanne: Yeah. He did it in a way that was a great idea. It is a great idea.

Jason: What is the idea?

Joanne: The idea is that chef’s, heavily curated at this point, can come and create their own site on Kitchen Surfing.

Jason: A profile.

Joanne: A profile of who they are or what they cook or who they’ve cook for, some sample menus. Then you go on the site and say, “I want to have a dinner party for 12 people. This is what I want to spend. I want italian food.” People come back and bid on it.

Jason: Oh. So you outline it then they bid?

Joanne: They can bid. I think that it will evolve into other things.

Jason: That’s revolutionary though. I love that idea because I can have this at a dinner party. I’m like, “Oh. I gotta find a chef.” Then negotiating with them… You always feel like when you’re negotiating with a chef that it’s almost like I want to have this be really special so I don’t want to have you cutting the cost. I want you to make it wonderful.

Joanne: Right. It’s all about how much you want to spend. If you want to have 4 or 5 people you and you want to spend $200 that’s going to dictate what the meal is.

Jason: Yeah.

Joanne: But it’s up to the chef to be creative and make that happen.

Jason: Right. It would be a hell of a roast chicken.

Joanne: It would be a hell of a roast chicken. So you are giving a lot of these people that are in industry that you have these accolades of these phenomenal chefs. They’re not making that much money, right?

Jason: Yeah. The guys at Mario Batali’s Place or Gordon Ramsey’s Place, they’re making minimum wage or $10 an hour or something, the line cooks.

Joanne: Yeah. They’re not making… right. They can go on Kitchen Surfing and they could actually make a name for themselves. There is one guy that I hired last summer who’s terrific. He went on to open a restaurant. I put money in his restaurant.

Jason: Ah. So they can really get their legs under them there.

Joanne: Yeah.

Jason: People bid on your dinner. That’s interesting.

Joanne: Right.

Jason: A lot of people are getting these chefs to do it on a regular basis for them. I noticed that trend in LA. That would be a great thing to.

Joanne: LA is one of the next stops.

Jason: LA is amazing because what people are doing in LA, even in Palo Alto, I notice that whenever I go to somebody’s house and you open their Sub Zero huge refrigerator it’s like boxes and boxes of food. Like those glass containers with dates. Like, “Oh. Here’s my kin wah.” “Here’s my kale salad.”

Joanne: Well you can have somebody come and do that for you for the week. I mean you can do whatever you want, right? But you have access to someone who’s a fantastic chef.

Jason: It’s sort of like AirBnB, a collaborative consumption of chefs.

Joanne: A hundred percent.

Jason: That’s a brilliant idea. Scoot Networks, that’s another great one. You and I were both scooter riders around Manhattan for a long time.

Joanne: Exactly.

Jason: Scoot actually launched at the Launch Festival two years ago. How did you find out about them? They’re only in San Francisco, correct? Tell us about Scoot.

Joanne: They’re only in San Francisco, which is kind of funny. I generally don’t do any deals in San Francisco but my husband told me about them. I called and talked to Michael. I really liked what he was doing because I got it.

Jason: Right.

Joanne: I said, “Why San Francisco? Of all the places to launch a scoot business.” They’re actually breaking even. They’re doing well in their first round. Which is pretty damn impressive.

Jason: Yeah. They’ve got 20 of them, 30 of them? $25 a day or something.

Joanne: Yeah. I don’t know exact numbers.

Jason: I ran into him in the street when I was there last time.

Joanne: He’s doing fantastic. He’s a great entrepreneur.

Jason: But that’s made for New York.

Joanne: It’s made for New York. The truth is it’s made for any urban city.

Jason: Dense city like a european city. Sure.

Joanne: London, Paris.

Jason: Barcelona.

Joanne: Barcelona, New York. Boston would be good. Right.

Jason: Interesting. Food52, that’s another great one. How are they doing?

Joanne: They’re doing really well. They just closed their series A, I want to say 6 months ago, with some really great investors. They are starting to kick off their ecommerce platform in a bigger way.

Jason: Let’s talk about MOUSE. I’m here in New York. I flew in.

Joanne: I know. Thank you.

Jason: Because you’re being honored tonight for the 15th anniversary of MOUSE, Making Opportunities to Upgrade Schools and Education. Non-profit founded by, I think, Andrew Rasiej. Then you were the executive director for a good portion of time. Tell us what is MOUSE and how did you wind up getting involved with it?

Joanne: I’m going to tell that story tonight.

Jason: Tell it here to my audience first.

Joanne: Going back down memory lane… I knew about MOUSE. We were also involved in our own lives in the industry. One day was like a year.

Jason: Yeah. There was a lot going on in the 90s.

Joanne: There was a lot going on in that time period. It was like insane. The first even that we put on from the Rising Tide Summit…

Jason: Right. I remember.

Joanne: … which took place at the New York Historical Society on…

Jason: Where is that?

Joanne: … on 78th and 77th in the park. At the end of the day Andrew brought on stage ten kids from high school who had never touched and never seen a computer and had never had any access to technology.

Jason: Wow. It was very powerful. Yeah.

Joanne: It was. I remember everyone in the room, I was one of them, was like, “Oh my God. Everything we’re doing is about technology. OK. If those kids don’t understand technology or have no access to technology…

Jason: This is like 97, 98 or 99 timeframe probably.

Joanne: Yeah.

Jason: 97?

Joanne: 97. How are we going to build our companies? Who are the next generation of entrepreneurs?

Jason: And consumers and everything.

Joanne: And everything. So I met with him. I met with Sarah Holloway who is really the co-founder as well. Then I left you.

Jason: Yeah. Brutal. It’s all right. We had Keith Long.

Joanne: That’s right.

Jason: We had a foundation. We were still on the upswing. The year after you left we tripled in revenue.

Joanne: Yes.

Jason: But you grew it from zero to four.

Joanne: Andrew called me everyday for 3 weeks at 3 o’clock on the dot. “Hey.”

Jason: “Hey. It’s Andrew.”

Joanne: Finally he’s like, “Whatever you want. You can chair it.” I was like, “Oh. OK. I like that. Sure.” That was it.

Jason: And you started working on that. What did MOUSE do during that sort of period? What were some of the highlights, some of the achievements, the accomplishments?

Joanne: I think the biggest accomplishment was the second we were in we raised a million dollars at the event that took place at the armory.

Jason: Right.

Joanne: Again, it was a different time. I raised, I think, $850K of that through emails. I mean there was so much money flowing.

Jason: Right. Everybody was taking companies public.

Joanne: Everybody was going crazy. “Oh yeah. I’m in 50, 25 sure no problem.”

Jason: Great. Let’s go.

Joanne: There was no, like, development. You had to hang out with these people. Even have a cup of coffee.

Jason: Right.

Joanne: You know, by doing that we grew an incredible base of an organization that depended on private money not public money.

Jason: Which was very innovative at the time when you think about it. Cause that’s really where a lot of philanthropy has gone is like private money to fund public good.

Joanne: Yeah. Then eventually they became involved in… The board of education pays them. But if you didn’t have that original private money that would never have happened. Then there was a lot of dart shooting. Should we try this program or try this program? Of course it was becoming wireless. We didn’t need to crawl through ceilings to put in wiring.

Jason: Yeah. The initial idea was to put internet in schools in New York. There was no money…

Joanne: To do it.

Jason: … to do it.

Joanne: That’s right. Then it became

Jason: There was unions trying to stop people putting it in.

Joanne: Yes.

Jason: I remember one of the first weekends we went to George Washington school. Was that the right?

Joanne: Washington Irving.

Jason: On Irving Place, 15th or 16th I think.

Joanne: 16th street.

Jason: We actually ran the cables. Nicolas Butterworth, myself, you I think, Andrew Rasiej.

Joanne: It was a major event.

Jason: We literally put the internet in the school and ran the cables to the computer classroom.

Joanne: That’s right. What’s interesting is that… Calvin Hastings actually came up with the concept of MOUSE Squad. Which is we basically hand pick a group of people in high school and junior high school as well because technology has changed. That group of people are the IT department for every school.

Jason: The students are the IT department?

Joanne: The students are the IT department. So there is still no IT department in the entire education system of New York City because of unions. It’s too expensive. Nobody could afford these people. So what happens to these kids is they become leaders in their community, they have access to technology, they get excited about technology and they know more than anyone else. This is the ticket.

Jason: Right.

Joanne: This is a ticket to their future.

Jason: Yeah. I mean if they’re the IT department in high school and junior high school they’re going to have a kick ass job when they graduate.

Joanne: That’s right.

Jason: Amazing.

Joanne: So most of them actually go on to higher education because… They have their own communities among them. So they have all these other people that are into technology. So yeah they have their friends but their it’s a community of their own within the school which is really important too. It’s vertical, it’s not horizontal. So you’ve got kids from 9th to 12th grade that are part of this group.

Jason: Ah. The New York City school system, has it become a total disaster? Has Bloomberg been able to make some progress on it?

Joanne: He has made some progress. You’ve got, I think, it’s a $26B business. It really should be blown up and start over again. I think Regents are a joke. I think that unions are terrible. I can go through a million different things. You know, funny enough, Fred and I just started a public high School. He’d been knocking on the door of the Board of Education for years then all of a sudden one day, “OK. Let’s do it.” Which is at Washington Irving high school.

Jason: That’s the computer school.

Joanne: That’s right.

Jason: What’s the name of it?

Joanne: The Academy for Software Engineering.

Jason: And you and Fred did this?

Joanne: Yes. So this is teaching STEM, right? But I don’t think that’s the end all be all either. There needs to be arts and music and computer science.

Jason: Well it would be great to have a STEM school in the system that specializes in it. We have Juilliard and whatever. Yeah.

Joanne: Particularly in New York where you have Bronx Science, you’ve got Stuyvesant. You have these sort of individual, unique schools. Next year they’re going to roll that ability for 10 other schools to use it. I think they’re starting a couple other of these schools so they’re will be one in each borough.

Jason: Oh wow.

Joanne: You know the hardest part was to find the teachers to teach these curriculums.

Jason: Right. They don’t exist in the New York City school systems as it is.

Joanne: There was one computer science school in Bed-Stuy.

Jason: Do or die.

Joanne: In Stuyvesant. Which is why it was just like, “Are you kidding?”

Jason: So you have to go outside the school system to try to find them or recruit.

Joanne: In the end I don’t know exactly how they went about recruiting but yeah.

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Jason: So your kids are all going off to college. When we met they were all kids. Babies in fact. What’s next for you? You’ve got the empty nest now, I think. Last one is going to college.

Joanne: Last one is going to college.

Jason: Are you going to start a venture firm?

Joanne: No.

Jason: A proper angel fund? What do you think?

Joanne: You know, I’ve been asked to do that so many time. I have a bunch of people who come in after me in every deal I do. I don’t want to be responsible for other people’s money.

Jason: Yeah.

Joanne: I really don’t. If I decide to take off for 3 weeks I don’t want someone to say, “Why are you doing that?” Right? I’m happy to engage those people. I’m happy to educate those people what it means to be an angel investor, right?

Jason: Yeah.

Joanne: I think it’s a much better way then just writing me a check. I also put on this conference every year. We’re going into our 4th year in January, called the Woman’s Entrepreneurial Festival. Which I do at the ITTP department at NYU.

Jason: Oh. OK. When is that?

Joanne: It’s in January.

Jason: It’s in January. Female founders or aspiring entrepreneurs.

Joanne: Yeah. Anyone from people that are from 18-65 basically attend the event. You have to apply to come.

Jason: How many people come?

Joanne: Last year was 300.

Jason: 300 women?

Joanne: Yeah.

Jason: Any guys come or no?

Joanne: Actually 3 guys came this year.

Jason: Security? The guy who was working the coffee. I want to come to that. Maybe I can sneak in and get an invite.

Joanne: Yeah. Apply.

Jason: Maybe I can interview somebody or something.

Joanne: No. It’s a great event.

Jason: What do you think is the thing that tips a woman over from not being a founder to being a founder? What do you think is that moment? Is there something that they see another female entrepreneur or something that happens inside them that makes them want to make that jump that we can sort of focus in on and make more happen or is it just a matter of time?

Joanne: I think it’s a matter of time. If you look most women are older that start a company. They’re not 22 and 23. That’s on average. That isn’t the norm.

Jason: Right.

Joanne: But if you look at women’s businesses over time, women tend to build businesses that fill a void in their lives.

Jason: Interesting.

Joanne: Right? I’m sure Robin Chase from ZipCar basically said one day, “Wow. Wouldn’t it be great if I could…” There you go. Now she built ZipCar. So if you look at things that women have built over the years, refrigerators, ladders when there’s a fire that drop through a window. I mean things that filled voids in their lives.

Jason: Which is really… if you think about it in terms of consumption… if you build something that you yourself want you can have pretty great product insight. There’s definitely going to be a market.

Joanne: Right.

Jason: Whether the market’s one person or 1%.

Joanne: Or thousands of people or millions of people. Certainly with a flatter world now you can have more people like yourself out there that may be interested in your product. So I think we’re going to see more women entrepreneurs. I have figured out how to have balance as working and being an entrepreneur working and then having a family.

Jason: How did you figure it out? What do you think the keys are? That is… I mean my wife’s going though this right now. She wants to be an entrepreneur. She has a little one at home. She wants to have another one possibly. Having a baby and taking care of a child is a full time job in and of itself. It’s tremendous feelings of guilt if you’re not with the child at all times. That can happen. You balanced it. What’s your advice to women who are trying to figure out how to balance having a family. It doesn’t seem like men seem to have a problem with it.

Joanne: Yeah. Men have no problem with it. I would say…

Jason: I feel guilty sometimes.

Joanne: A couple of things is… First of all, women that are waiting to have children, don’t wait.

Jason: Just have them.

Joanne: Have them. Do it. Have them as soon as you can. As soon as you start thinking about it have a child.

Jason: Right.

Joanne: You will figure it out. That’s number one. Number two is you just decide what is important to you. If you really want to go out and do something and start a business and be around for your children too you’ll figure out how to balance it. For me, I got off the train I got on the train. I’ve done that twice. I set goals. I set parameters. So I took the kids to school and went off to work. There was a point where I would also pick them up from school. So basically my life was in that small time period. Then at one point I didn’t have to have that small time period because nobody cared if I was at home until 5 or 5:30. But I did want to make dinner. I wanted us to sit down as a family. So I figured I had to juggle my life around that. Then the beautiful thing is I went to every basketball game because I could.

Jason: Right.

Joanne: So I think it’s just a matter of figuring out your priorities.

Jason: I think you have really good time management strategy.

Joanne: Well I’m like a freak of nature when it comes to organization. So yes. You do have to be very, very organized.

Jason: You gotta spend some time with my wife. She gets just absolutely over… I have like… Here I am in New York for just 72 hours. I start to feel a little bit guilty about not being around my daughter. Even though it’s like a 2 or 3 day trip. I used to take a week trip to New York. God. Take a couple of Knick’s games in. Well… that’s kind of brutal.

Joanne: So sad.

Jason: Did you ever have that sort of, “Oh. I’m missing my kids,” something?

Joanne: Yeah. But then when you get back and they see you, nobody remembers that you were gone for 3 days.

Jason: Yeah. Exactly.

Joanne: Right? It’s life. I think that it’s important for kids if you really want… You are the ultimate role model for your children, right? If they see that you don’t have a life for yourself, I don’t think that’s healthy either.

Jason: Right. Yeah. It must make them feel good to see that my dad or my mom are hard working, getting stuff done in the world.

Joanne: Yes.

Jason: You gotta set that example as well.

Joanne: Right. I think Fred and I have set that example for our children.

Jason: Yeah. Your kids turned out wonderful. My God they’re all doing incredibly well.

Joanne: Yeah.

Jason: Different schools and out of the house most importantly. Well Joanne Wilson this has been absolutely fabulous. Everybody follow @thegothamgal. If you’re a female founder this is the person you want to break bread with. This is your number one target in terms of getting an investor. What do you look for… I mean you said your gut but it’s got to be some tangible things that entrepreneurs need to have. I mean you don’t want people coming to you with ideas. You want to see a product.

Joanne: I want to see a product. I want to see traction. I want to see a road map.

Jason: Right.

Joanne: Granted zero of zero is zero at this point, right? So I’ve always been sort of a generalist like taking information from a bunch of different places. You know, like the woman who literally cold emailed me with this Mercaris. I read the deck… By the way I answer every email and I read every deck. I give feedback and I say I can meet you or not meet you. But I’m always nice.

Jason: Right.

Joanne: I said, “You know this is really interesting,” and sort of engaged her in conversation. Then as we started talking and I started understanding what she was building and why she was building it… I mean both of us started thinking big and having conversations on what it meant. So I think that that is the connection when you talk to someone. So when they’re sitting on the other side and you sort of become… LIke these two girls, Carla and Kimberly, who are the entrepreneurs between Have to Have. When I first met them… I actually had this conversation with them the other day… I thought this is a stupid business. I like them but I don’t like these businesses. I said…

Jason: You don’t like social shopping stuff.

Joanne: It was, you know, you make money on affiliate fees. Which makes zero sense to me. A $100M business and you get 10%. It’s not a business.

Jason: Or 5%.

Joanne: Or whatever it might be, right? Everyone is like, “Oh, yeah. They’re totally into it.” They just want money wherever they can get money, these affiliates. So they came back to me over the course of the summer. They kept me engaged with what they were doing. They realized two weeks into this business that it was not going to work.

Jason: It was a dog.

Joanne: It was a dog. They completely pivoted the business. Then they started working, working, working and got back to me. We had a conversation. They got back to me again. We sat down and they brought their CTO with them. We started talking about what they had built. We had this amazing conversation about now this is a business. It could do this, it could do this, it could do that. I thought to myself, “This is the kind of entrepreneurs I want to back. These women are going to figure it out no matter what.”

Jason: So you want to see that ability to think critically and debate and discuss stuff.

Joanne: Yes. And push things forward in an intelligent way. Hopefully down the right path. So that business now is doing unbelievable.

Jason: What is the business exactly now? What did they pivot to?

Joanne: They are basically a native advertising business but it’s with… A visual native advertising. So it’s commerce native advertising. Think of it as the new pop up ad.

Jason: Got it. Interesting.

Joanne: You can go on there as a brand, as a commerce site, as anything, very simply take their widget and go.

Jason: Interesting. I’ll check that out. Alright. Kitchen Surfing, Daily Worth, Food52, Vengo Labs, Scoot Networks, Videolicious, Have to Have, Loverly, Mouth.com previously New York Mouth. Lots of great plugs in there. Everybody follow @thegothamgal. Check out GothamGal.com of course. Her awesome blog and Joanne@SolomonWilson.com. That’s her email. Wow. Amazing having you on the program.

Joanne: It’s great seeing you.

Jason: Tell a funny Jason Calacanis story from back in the day.

Joanne: Oh my God I have so many I don’t know where to begin.

Jason: Tell them one… Cause the audience.. I have a lot of super fans. They’re kind of obsessed with me. Tell them one that’s particularly embarrassing or shows how naive or stupid I was as an early entrepreneur.

Joanne: So tell the one about how I wanted to sell your company and you didn’t want to sell it?

Jason: Yeah. Tell that one. What an idiot I was. Biggest mistake of my like, right? I could have made $20M.

Joanne: You obviously landed on your feet.

Jason: Right. Tell that story.

Joanne: So we had built this huge business.

Jason: Yeah. Millions of dollars a year in revenue.

Joanne: Millions of dollars in revenue. We had this glossy magazine. It was on every newsstand in New York if not other places. We had an event business. Which is fantastic. I love events. You get all the money before anyone shows up for the event.

Jason: Love it.

Joanne: We had started a rag. We had built a sales staff.

Jason: Yep.

Joanne: We had like a real business.

Jason: Yep.

Joanne: I believe there were two companies that were interested.

Jason: Macler was interested.

Joanne: There was another one too. It wasn’t Hearse but it was like a Hearse.

Jason: Yeah. Someone who was like tangentially interested.

Joanne: Exactly. It had a bunch of magazines.

Jason: Not as interested as Macler.

Joanne: I think it was $50M…

Jason: $20M.

Joanne: No.

Jason: It never got up to 50.

Joanne: I think there was a lot of conversations that were much higher than $20M.

Jason: Really? I’m such an idiot.

Joanne: You were like…

Jason: I’m going to build.

Joanne: … “I’m going to be the next Rupert Murdoch.”

Jason: That’s what I wanted to be.

Joanne: I was like, “Oh my God. I am so much older than you.”

Jason: You’re not that much older than me.

Joanne: I was. I am. I’m ten years older than you.

Jason: Are you? I’m 42.

Joanne: I’m 51.

Jason: God. You look like the same age.

Joanne: I’m older than you.

Jason: I need to get in shape. I need to eat more kale. You look the same age as me. You’ve aged gracefully. Not me.

Joanne: I was like, “This is a blip on the map. This whole thing is smoke and mirrors.”

Jason: It’s going to explode.

Joanne: “It is going to explode. This is your window. Tomorrow it closes a little more.” You’re like, “No.” I was like, “I quit.”

Jason: No. See I’ll tell you why.

Joanne: Then I quit.

Jason: You did. I thought… See I’ll tell you what I got right and what I got wrong. What you got right was you realized it was going to implode.

Joanne: Yes.

Jason: I was looking at the big picture and I said, “The internet will always be big.” Right?

Joanne: Yes.

Jason: But I had never seen anything explode in my life.

Joanne: I’m not so sure I did either.

Jason: Well maybe the 88 stock market crash and stuff like that.

Joanne: Yeah, yeah. I guess.

Jason: You saw the implosion coming. I didn’t think it was going to implode as bad as it did. You were right. I was wrong. I should have sold. But then you know what? I think a lot of times you need to go through that as an entrepreneur and make your mistakes. Also… I always tell this story… you thought we should go national and I was stuff on local. That was another big mistake that you saw way before I did. But you had 10 more years experience. But I always tell people…

Joanne: Yeah. I did want to go national. I was going on about the national.

Jason: You were like, “Go national.” I was like, “Naa. I want to do New York.” You know what? You can be right in the long term but so wrong in the short term.

Joanne: Yeah.

Jason: Then what makes you a great entrepreneur is your ability to ignore everybody and just do what you want to do. It can also be the thing that is your demise.

Joanne: Yeah. You know, listen, I am a grower.

Jason: Right.

Joanne: I’m great at the big picture. I know how to grow things. I know how to build businesses that make money.

Jason: Right.

Joanne: I think it’s innate. I’ve always been like that.

Jason: Yeah. Even in the smatza business.

Joanne: In the smatza business I made a lot of money.

Jason: Fred’s like, “You should hire my wife to do your ad sales.” I just put out an email saying, “I need an ad sales person cause I can’t handle all the ads that you want to put in.” He said, “You should talk to my wife.” I said, “What’s her qualifications?” He’s like, “She was in the smatza business.” I’m like, “What’s a smatza?”

Joanne: It’s clothing.

Jason: It’s clothing. 37th street.

Joanne: No. I think with Curbed it was the same thing. It was my first investment but Fred always said, “If you had one lemonade stand on the corner, you know, within a year you would run a chain across the country.”

Jason: Right.

Joanne: So it’s sort of not surprising that I wound up with 39 businesses that I’m involved in. But I love it.

Jason: Well listen. I never got a chance to thank you, I don’t think. But thank you so much for the hard work and putting up with me. I learned so much from you. Even to this day when I sell I tell people, “Just sell it. Ask for double.” Cause that’s what you used to always do. I’d be like, “Maybe we can sell it for ten.” You’re like, “Let’s try 20. Then we’ll discount to 15.” I was like, “Ah.” To this day… I like literally responded to an email today where somebody was selling the Launch Hackathon. One of our events. They’re like, “I’m a little concerned because we’re making this $15K and people previously paid $8K.” I’m like, “Well make it 15 and you can always discount it if you need to, whatever. But challenge people a little bit.” You always challenge people, I think, in terms of supporting things. I think that’s why you’ve had such a great success in your career. It’s that you’re never afraid to challenge people to spend money on products and services. Even MOUSE which is a non-profit. That makes the world better.

Joanne: Yeah.

Jason: You gotta be a little bit bold. I think you have a boldness to you.

Joanne: I do have a boldness to me. Which is, I think, why sometimes I want to go with those entrepreneurs and be the one pitching.

Jason: Yeah. You want to shake them up a little bit. Say, “Hey. Be proud of what you made.”

Joanne: Yeah. But I do. I spend a lot of time with them and say, “Hey. Let’s pretend that I’m the person on the other side of the table.”

Jason: Roll play. You have a boldness. I think that might wind up being your legacy and the big value ad you have with women founders. Cause I think at times they are a little mousy about things. They’re afraid to ask for that big number. I mean all entrepreneurs are but I do see it in women sometimes. They’re afraid to like have the big ask. Do you find that like sometimes they’re afraid to just, with gusto, say, “Give me $100K for this product.”

Joanne: I think it’s hard. There’s this one entrepreneur that we just closed her series A. Which I actually led. Not financially.

Jason: Just led the process.

Joanne: No. Jay did the paperwork. We led the process because you can now, right? There’s a lot of money out there in different verticals. The people in the verticals actually understand certain businesses. So we just closed this round. She was going back and forth with this one group of guys. She was very frustrated. I said, “When you go in there I want you to think I’m on your shoulder. Think, what would a guy do?” She was like, “I went and they were like aaaaa.” She said, “Are you guys in or out?” They were like, “We’re in.” She walked out. She was like, “Wow.”

Jason: Not like, “Well. If you guys are interested you could call me. This is my number.”

Joanne: Right.

Jason: She was like, “In or out. Let’s go.”

Joanne: “Let’s go. I’ve got things to do. I’ve got businesses to build. You’re going to invest in me or not.”

Jason: Right. Let’s just… I’ll take a quick no. I want a yes but I’ll take a quick no.

Joanne: I wish people would be better with the quick nos.

Jason: I am awesome at the quick no. I just tell people like, “Listen. It’s not a fit for me. I can’t help.”

Joanne: Which is great.

Jason: Move on to the next one.

Joanne: People say, “This is fantastic. Definitely get back to me. I want to hear more.” Then you never can get back to them.

Jason: Right.

Joanne: Why didn’t you just say, “No. This isn’t for me. It’s been a pleasure. See ya.”

Jason: Yeah. Or, “You can keep me up to date but it’s probably not a fit.”

Joanne: Right.

Jason: I tell people all the time… They’re like, “I have an ad network.” I’m like, “Stop. I can’t help an ad network. That’s not what I do.” You know. Like, “I’m going to do that.” “Nope. Stop. I don’t have knowledge about that. How can I be value added? I have to have it my way.”

Joanne: Right. I think that’s really important. I don’t know why people… Maybe because I was in smatza. Maybe cause I was on the other side first.

Jason: You were a seller or buyer?

Joanne: I was both.

Jason: Oh right. So you got to see both sides and what worked on both sides.

Joanne: Exactly.

Jason: You got to see people who were like, “Listen. Are you going to buy this or not cause I got somebody on line two?”

Joanne: Exactly.

Jason: “In or out.”

Joanne: Yeah.

Jason: “Let’s get going here.”

Joanne: Yeah.

Jason: Listen. Joanne Wilson… not only a friend but a mentor to me. My big sister. You’ve always been so good to me. I can’t thank you enough.

Joanne: You’re welcome.

Jason: See I learned so much from you. I’m so excited for you to be on here tonight. It’s so overdue. If you’re a startup founder, especially a female one, this is the gold standard, Joanne Wilson @thegothamgal. So great having you on the program. Continued success.

Joanne: Thank you.

Jason: Thank you.

Follow on Twitter:
http://twitter.com/jason
http://twitter.com/kirinkalia

LAUNCH:
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Launch Education & Kids Festival: http://launchedu.co
Launch Festival: http://festival.launch.co
Launch Hackathon: http://launchhackathon.com/

 

Special thanks to the members of the TWiST Backchannel Program!

 

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The first episode of This Week in Startups with guest Brian Alvey, CEO of Crowd Fusion.

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