105: From AOL Lawyer to Purpose-Driven Deal Maker with Jan D'Alessandro.

STUCK - 

Episode Overview

Meet Jan DAlessandro, who pioneered remote work at AOL in the 90s and now directs billions in corporate philanthropy at Pledge One Percent. Her story shows how lawyers can leverage their skills far beyond traditional practice into business development and social impact.

Key Topics

• How Jan invented working from home at AOL in the 1990s
• Transitioning from corporate law to business development
• Building win-win partnerships across tech, media and entertainment
• Creating sustainable corporate giving programs
• Navigating career transitions in times of uncertainty

Key Quotes

"I got to a point where I thought, I don't really care about the indemnity clause. And then I realized - you can't do this job anymore because somebody needs to care about that. And it wasn't me."

"Culture eats strategy for breakfast every day."

"As a lawyer, you're trained to think critically... to not take things at face value and see how you can turn it into something positive for both sides."

Practical Insights

• Use your legal training as a foundation for other roles: 
  • Critical thinking
  • Negotiation skills
  • Deal structuring
  • Understanding multiple stakeholders
• Look for opportunities to merge your professional skills with personal interests
• Consider how your expertise could apply to emerging fields like AI
• Focus on building win-win partnerships rather than just transactions
• Stay connected to what energizes you, even if it means changing roles

Key Lessons for Career Transitions

1. Be honest with yourself about what naturally energizes you
2. Look at what you spend your free time doing - there are jobs related to any interest
3. Focus on transferable skills rather than just industry experience
4. Don't underestimate the value of your professional training in new contexts
5. Consider how emerging technologies like AI create new opportunities in familiar industries

Guest Bio

Jan DAlessandro pioneered work-from-home practices at AOL in the 1990s before transitioning into business development roles at major tech companies. As head of Pledge One Percent's Equity Initiative, she's helped direct over $2.5 billion in corporate philanthropy. Her career spans law, tech, entertainment and social impact.

Resource Mentioned

• Marianne Williamson quote: "Playing small doesn't serve the world"
• Cheryl Sandberg's gratitude journaling practice
• The Innovator's Dilemma by Clayton Christensen

About Stuck

Subscribe to Stuck on Apple Podcasts, Spotify, or wherever you get your podcasts. Email us at stuck@213studios.com. Produced by Rob Curtis, Jamal Stockton, and Ximena de la Tijera.

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You can watch each episode on Youtube https://www.youtube.com/@areyoustuck

This show was produced by Rob Curtis, Jamal Stockton and Ximena de la Tijera

Transcript

Rob Curtis (00:15)
Today we're joined by Jan Delisandro, who pioneered partnerships at AOL and Yahoo back when tech companies were trying to figure out how to work with artists and creatives. She's since founded Blue Jay Strategies and leads Pledge One Percents Equity Initiatives, directing billions in corporate philanthropy. Jan's story is particularly relevant because she found creative ways to leverage her legal background far beyond traditional practice. Jan, welcome to the show.

Jan DAlessandro (00:39)
Thank

Jamal (00:39)
Welcome, Jan.

Jan DAlessandro (00:39)
you so much, Rob. Thank you, Jamal.

Rob Curtis (00:42)
In the 90s, you basically invented working from home at AOL. I'm curious, what did your colleagues think that you were crazy for back then that's completely normal today?

Jan DAlessandro (00:52)
So when I started at AOL, know, the headquarters were in Virginia, just outside of Washington, D.C.,

I was, it was...

my seventh year in private practice, the year I would have been made partner. And I decided I didn't want to be a partner in a law firm, I wanted to be part of building something. And he called me just right around that time.

so they offered me the job. And the deal that we structured was that I would live in California, but one week out of every month, I

would go to Virginia and I would spend a week at headquarters.

And it was incredible. my career at AOL started as a work from home career. I would go into the office in San Mateo most of the time. And then we bought Netscape. So I had an office there. And then we bought a music software company, spinner.com, that had offices. So at this point, I had three different offices in the Bay Area. And it became sort of silly for me to go in. So I would just really start going in when I needed to meet with people.

And I found instead of commuting an hour to an hour and a half, I could get more done if I was at home. And then I had my first child in 1997. And that really gave me a reason to not be spending so much time on the road.

So that sort of, it sort of happened organically, but it just kind of worked. And then I just took that with me. So every other company I went to after that, you know, I basically said when I took the job, you know, I spend the summers on the East coast, you know, I'll be here. and

The first job I took after AOL was in San Francisco. So I went in most days, but I sort of got in the habit of not going in every day. And then the next three companies were based in Silicon Valley. And it was, again, just not efficient to be commuting all the time. So one was in Palo Alto, one was in Mountain View. The other one had a hybrid. was half actually Los Angeles and half San Francisco. So I just sort of got into the habit of only going in two or three days a week.

And it just kind of worked. So it was my mother used to joke that I invented working from home.

Rob Curtis (02:50)
And look at what we've done since then.

Jamal (02:52)
walk us through that moment when Backplane was ending. What practical steps did you take?

to create your next opportunity.

Jan DAlessandro (02:59)
Yeah, that's a very good question. I started my journey to leave the strict practice of law at AOL. So I was hired by the legal department. But I'm a partnership builder, and I'm a people person. And so it got increasingly more frustrating for me, because really, is the job of a lawyer if you're in private practice as a corporate lawyer?

And even as an in-house lawyer, your job is to paper the deals. You're part of, you're negotiating the deals, but then, you know, at a big company like AOL, it became more and more just about papering the deals and negotiating and negotiating the legal terms. And I found myself getting super frustrated, you know, when I'd be on the phone with a lawyer from, you know, Warner Brothers Studios who was just hammering me on the indemnification clause. And I got to a point where...

I thought, don't really care that much about the indemnity clause. And then I realized like, you what, you can't do this job anymore because somebody needs to care about that. And it wasn't me. So I moved over into a more business development, business affairs role at AOL where it was more about, you know, finding win-win partnerships, know, win-win partnerships, you know, negotiating these big deals that were, you know, moving the needle in a massive way for both companies. And then I ended up moving over to run the AOL Time Warner Foundation.

And I got into that as, it was really as part of a deal. We created a product called Network for Good that AOL had a site called helping.org that was really information about good things that people were doing in the world. And we thought, we can do a lot more than this, particularly if we make it not be just an AOL owned property. So we created a joint venture with Cisco, Yahoo, and some of the big foundations. We spun it out and those companies.

We funded it for the first three years and then we said you need to create your own standalone business. Which we did and it became the preeminent tool that companies used for fundraising online for many, many years. So then I left AOL in 2002. The internet bubble blew up, things were a mess. I was pregnant with my second child who was born in 2001. I very difficult pregnancy on bed rest for three months.

And anyway, so then I took off some time to be home with my kids. I left a while, spent, you know, I was getting divorced. I spent four years home with my kids. And then when I went back in, in looking for work, it was sort of serendipity. You know, I ran into someone at my kid's school who we were taking an adult Spanish class and she said, you're a lawyer. My husband just raised a bunch of venture money and he needs a lawyer. So we went in and when I, when I was hired by this company,

because I had done both, legal and business development, that was the role that they hired me into, was VP of business and legal affairs. And so it was a hybrid role. And then each of my next three companies, they hired me as general counsel and head of business development, because it was sort of ingrained into it. So that's what I did. One of my companies was sold to Facebook, one was sold to Apple. As things go, one didn't make it.

You know, and then the company that Backplane was started by Lady Gaga. And that was a company, I did a brief stint in between my three startups at Yahoo, where I was running business development for sports entertainment and lifestyles. that was it, sorry, I'm really giving you a very long-winded answer to your question, but it's, you know, it's sort of part of the story. But so Yahoo, you know, I was doing deals, I had a team of about 10 people working for me.

doing big deals, it was kind of fun to be on the side of seeing how a big company looks at deals as opposed to being the startup who's begging people to take your phone call. But it was frustrating for me because Yahoo was on the wane. There were four CEOs in the one year that I was there. It was very difficult to get things done. There was a lot of jockeying position. And even more frustrating, there were a lot of people there who honestly were just collecting a paycheck.

They didn't care. The company had lost it sort of true north. weren't, they, know, and so I was able to do some really cool things and I loved my team, but I got really frustrated. And after a year, I had this opportunity to go work at a startup that was doing deals across sectors, the kind of deals that I like to do. so we, Backplane was a platform that was built to help anyone create their own social media network.

And it was really the idea was that if you are a fan of Lady Gaga's music and you go on Facebook or Twitter, she had 70 million followers on Twitter and 50 million on Facebook. But if you go on those sites and all you're doing is talking about Lady Gaga, your friends are going to get kind of sick at you. You know, like, my God, here you go again. Like, yes, we like her music, but enough. And so we built Backplane and we powered the back end of littlemonsters.com, which was basically, in essence, her fan club.

And so what it was was a million of her super fans. And we did some really interesting tests where we showed that marketing to your super fans really works. built tools that like when Live Nation did a $25,000 ad buy on littlemonsters.com and sold out the tour in an order of magnitude faster than they'd ever sold out a tour before. They said that it was the best ROI on a $25,000 investment that they'd ever seen.

You know, we built tools that allowed the super fans to market onto the other platforms, things like that. anyway, and then our mission was just, we said, all right, we don't want to be pigeonholed as a fan club platform. We want to be the tool that anyone who wants to create a private social network. So let's go out and do deals with the biggest brands in each vertical that we can. So we did deals with Cirque du Soleil and Conde Nast across all their verticals, the UN Foundation, Major League Baseball Players Association, know, Coca-Cola around soccer.

Major League Soccer, they're a big thing. Anyway, so we did this and to be honest with you, we ended up selling the company to a private equity firm after, I think I was there for four years when we sold it. what was interesting is, and this is true, I don't know if you've ever read Seth Godin's book, The Innovator's Dilemma, that was our problem, right? We were too early, because companies were still in the world of counting likes on Facebook and counting followers on Twitter.

and when we would get the deals done and then go meet with the marketing teams, they didn't know what to do. They were being measured on how many followers did you get. They didn't know what to do with us. And so we tried to, you we had a consulting arm, we tried to teach them and it just, wasn't a massive success, to be quite honest. So when I left, I thought, you know, I don't think I want to jump into another operating role again. I need to pause for a moment. You know, I've learned, you know, I've been doing deals for

many, years. I've got, I have this sort of unique skill set in knowing how to do deals across the San Francisco, Silicon Valley tech world and the New York media and publishing world and the LA entertainment world. And you know this Jamal, I mean, maybe you do too, but like the nuances, right? You know, in LA, you never have a bad meeting. You're amazing. You know, everything is like, and in New York, they're like, they're going to tell you you're an idiot the minute you walk in the room and know this is never going to work. Right. But

you know, there's, and that's, you know, I'm making light of it, but you know, there are certain nuances in what, you know, each of the different industries care about and how they negotiate and things like that. So I decided that, you know, I think, you know, I'm not, I'm going to take a minute. I'm not going to jump right into another operating role. I, know, I looked at, which I probably should have done. Like I was looking at jobs at LinkedIn and, you know, Metta, Facebook, it was still called Facebook then, you know, I don't know, Google, like that was, you know.

That was a mistake that I made when I left AOL, turning down a job at Google before they went public because I wanted to be with my babies. But I was like, what would I do with all that money? Pay for therapy. don't know. Anyway, so when I was at Yahoo, I was doing all the music deals and I met a guy named Jimmy Chamberlain, who's the drummer for the Smashing Pumpkin. And at the time he was running a tech company in Chicago.

Rob Curtis (10:31)
for the kids.

Jan DAlessandro (10:45)
And he's such a great guy. we had a really good time going around. And what we thought is, between the two of us,

We're extremely well connected. We know how to do deals. We know how to negotiate. And we thought like we can really help companies. So we did that, you know, for a few years. Most of my deal flow in the beginning came from venture capitalists who I knew, who would say, you know, I've just invested in this company. The founder could really use your help. And what I would do is help sort of with the developing the business development partnership strategy. Like what kind of companies should you

work with, know, how should you target, you know, always, always, I prefer doing a few bigger deals than a gazillion little ones, but sometimes you have to do both. And so, you know, and then because I, you know, at this point, you know, I can get to any company, you know, I just know so many people and I, you know, throughout my career. So it was great. And then after a few years, Jimmy ended up going, the pumpkins ended up getting back together. So he ended up going back on tour with them. And so

you know, we're still very good friends and, you know, refer things, you know, back and forth to each other, but he's, he's really a touring musician again. And, I found myself, you know, really drawn more and more to purpose driven companies. And I thought, you know, this is great. I'm helping all these tech companies, but some of them, you know, I won't say who, but I just didn't really care that much about what they were doing, you know? And I thought, you know, I really, at this point in my career, you know, and I had, I had, you know, at

AOL, had a role that was very focused strictly on philanthropy. At all of my other startups, I would sort of try to wedge the social impact into what I was doing. And it was great. At Top Spin, which is a music software company, I worked with the product and engineering team to build tools to help the musicians engage their fan base in philanthropy and activism.

at Backplane, I led the deal with the UN Foundation, which was really cool. We powered a social network for them. know, was all that. I thought, so I started getting more interested in companies like FinTech that were trying to democratize access to capital. I advise a company called Chime Bank, which is going public soon.

And so, and then I was approached by Pledge One Percent. So Pledge One Percent is a nonprofit that was started by Mark Benioff. When I was running the AOL Time Warner Foundation on the West Coast was when Mark was starting Salesforce and he had this, you know, did something really sort of.

you know, amazing and groundbreaking is right. One of his very first hires was a social impact leader, a woman named Suzanne DeBianca, who's the chief impact officer. He hired her in year one of the company and they came up with this model where they said, we believe that companies have an opportunity and a responsibility to give back and we want to make it easy. So they did what they say the one, one, one, one. So we're going to give every employee 1 % of their time.

which translates into three days a year of volunteer paid time off to go out and volunteer in the community. you know, interestingly enough, like on day one of orientation, new hires go out and volunteer for an hour at a food bank or whatever. They use that overseas service learning trips as a reward for top salespeople. So it's something, and it's really, you've sort of never seen anything like it. It's like a tech company that everyone is so excited and, you know, really, you know, it's a,

you know, it's something that is really ingrained into the company. One percent of product was also super interesting. They gave away any nonprofit who wanted to use Salesforce would get a one year free license. And then after the first year, they would sell it at an 80 percent discount and use 100 percent of the funds from that revenue stream to fund grants to other nonprofits. Interestingly enough, that became so successful that the head of sales said, please let me run that.

If you give it to me, I can make it even more successful and we can generate even more money. And they did. So they had a third party come in and value that business unit at $500 million. And salesforce.com wrote a check to salesforce.org for $500 million and brought it in-house and scaled from a thousand to 2,500 people selling into the nonprofit sector, continuing to create a virtuous loop. The 1 % of profits, as you know all too well, Rob, you do, Jamal, you actually run a real business that have products to sell, but most tech companies are not profitable.

Rob Curtis (15:00)
Not for a long time.

Jan DAlessandro (15:00)
for many years.

By design, choosing to invest in growth, not profitability, you know, that may be changing, you we'll see, but so the 1 % of profits, you I'll tell you about pledge 1 % with that because it was not relevant in the beginning. what Mark did is he said, I'm to donate 1 % of my company equity. So he did a warrant in between, I believe it was the series B and series C that became exercisable when they had a liquidity event, whether it's an acquisition or an IPO.

So he did that, then Salesforce goes public and all of sudden they've got hundreds of millions of dollars to give away. they went, Suzanne and Mark went and taught Google how to do it. It's what's funded, google.org. Scott Fakar, the founder of Atlassian, an Australian company, he caught wind of it and got in touch with them and he did it. And in Australia, the tax laws are such that it has to be founders donating the equity, but that's what he did. so they, together, Scott,

and Mark and Scott's CMO is a woman named Carolou Dietrich and Suzanne DiBianca. created Pledge One Percent 10 years ago as a nonprofit whose mission is to educate, empower and inspire every company to be a force for good using one or more of these four levers. So I knew about it because, you know, when I was running the AOL Time Warner Foundation, they were just getting started and what they have done is so unbelievable and groundbreaking and has inspired so many companies to file.

follow their lead. And I met the CEO of Pledge 1 % at an event and she called me, know, right when I was making the pivot with my consulting business to say, you know, I really want to work with more purpose driven companies and said, you know, we now have, this was four, maybe four and a half years ago, we now have 10,000 companies around the globe in a hundred countries who have joined Pledge 1%. We have maybe about 10 % due equity.

but we have a small number, eight or nine companies who set aside equity and then went public and together have generated $250 million in new philanthropy. And she said, know, there's a, challenge that we have is that if a company is already worth billions of dollars and so close to a likely exit, there's a feeling that it's too hard to get your investors to give up the dilution. So we need to figure out how can we inspire more companies. So I interviewed the CEOs of all these companies and their social impact leaders.

and we wrote a playbook that we sort codified into two different models how a company could set aside equity to fund their work. know, the earlier stage companies will do what Mark did with a warrant.

And the beauty of that is that, you know, they can lock in the social impact dollars, but the company's ability to take a tax deduction occurs when they have the liquidity event, when they may actually be profitable and have an opportunity, you know, to, I love that too, if a company is likely to exit through acquisition, which 90 % are, because then the shares don't, you know, they're not at risk because a warrant is a legally binding instrument. You can lock in the social impact dollars. And the only challenge is who gets to decide where the money goes. Is it the acquiring or the acquired company? So.

But we have ways to solve for that. As lawyers, know that, Jamal. But what we did was that for the later stage companies, we created a model where we said reserve the shares, disclose it in your S1, but then issue them in tranches over 10 years, 0.1 % a year. And then what we did is we published this book, then we built a coalition of we now have about 100 venture capitalists who are committed to supporting their portfolio companies and setting aside equity. And with these two tools, I've taken them from $250 million to $2.5 billion in new philanthropy created.

by companies following this model and building social impact programs, engaging their employees, engaging their customers. And what we see is that it's one of the most impactful things that companies can do to attract and retain top talent. So anyway, as you can tell, I'm so excited about this, I could go on and on.

may be surprising to you. was to me. that pledge 1 % grew out of the enterprise SaaS field.

maybe it's most likely probably because that's our network and those are the VCs who are supporting their companies. But these are companies that for the most part, they're selling business software, enterprise software that doesn't on its face have a social purpose. And so that these companies, they want to do something to give back and this is a construct that really works for them. And so it's...

You know, sort of cynical people will say it's, you know, cause washing, you know, it's a marketing and PR stunt, but it's not. You know, certainly not the companies who donate equity. It takes a lot of work and you got to go to your board and no one's going to do it if it's just for a PR stunt. And in fact, I've had many, many, many VCs say to me, you know, if a company really wants to do this, if the CEO really cares about this, I will support them.

If it's a PR stunt, I'm not going to, right? And it never, it usually never is. The other thing is, and the most compelling reason is, if you are a founder or even someone who's advising companies, having a social impact strategy and program is one of the most important things you can do to help attract and retain top talent.

people, know, young people do not want to work for companies that do not share their ethos for the most part. This is not, you this is a sweeping generalization, but you for the most part and having a social purpose, it's sort of like a guiding light and a true north that, you know, brings everyone together. You know, sometimes, you know, it's hard to get excited about selling enterprise software, but you know, but if you know that like, you know, every time I sell, you know, a big customer, I'm creating this much value, not just for that company, but also for the community.

both locally and globally and it's something that you see. This is also really interesting. One of our PledgeOne percent leading companies shared with me that the employees who are volunteering the most and unlocking the company matching program are three times more likely to stay at the company.

And so if you think about it, it kind of makes sense. It's just a different lens at looking at this data that, you know, these are people who care about their communities. They care about their jobs. They're, the top performers because they care. And so giving them something to sink their teeth into, you know, it really, it really does matter. And so that this is something, you know, I'm constantly asked with pledge 1 % like, how do you.

How do you convince a company that this is good for business? Well, that's the most compelling thing. And it's the same token with your customers.

You you asked at the outset, how are things changing? Well, there are not going to be legislative mandates to do good things for the next four years. We know that. I had this like sick, know, so Kamala Harris is a friend of mine and she actually married my husband and me in our living room in 2008 when she was district attorney. So, you know, we, like many of us, we were devastated when she lost, but.

I had this weird almost like delusional, I am a very optimistic, eternal optimist, maybe sometimes to my fault, but I thought, know, there's gonna be even more importance placed on the work that I and others like me are doing because companies are gonna have to step up voluntarily, not because they're told they have to, but, and why would you step up to give back is because it's gonna help you build a better culture.

And this is something that Mark Benioff talks about in his book, is culture eats strategy for breakfast every day.

Rob Curtis (22:10)
That's super interesting.

Yeah, I think I talked to a lot of early stage founders who perhaps once overlaid on mission without a business model and that's a lot harder to do these days. That's a really interesting take. Jen, just as bit of signposting on where we're gonna go from here, we're going to jump into some kind of lawyery type questions about skills, transferable stuff like that. I'm gonna come back to how the world is changing, AI, and we'll talk about...

Jan DAlessandro (22:19)
Yeah.

Rob Curtis (22:35)
the Marianne Williamson quote, and then we'll wrap up with some takeaways for people who are at this stage of their career. Cool, Jamal.

Jan DAlessandro (22:40)
Okay, sounds good.

Jamal (22:40)
Yeah.

I had a question while we were, and I was on mute there, so I was trying to interject. Yeah, no, you're fine. It was me. And we don't have to use this question. But I was recently watching something. It was a discussion at the World Economic Forum. And it was talking about philanthropy since we were just talking so intently about that. What's your thought about

Jan DAlessandro (22:45)
Sorry.

Jamal (23:02)
whether or not philanthropy is actually the answer to solving some of these social problems versus just taxing people appropriately in the first place and let the system work as it should.

Jan DAlessandro (23:12)
That's interesting. given, okay, let's just talk about the US and the current administration. I, as a taxpayer, would be very nervous about having faith that the money, that my money is gonna go where I think it should go, or in the most effective way. And so, you know.

We are citizens of this country and we have an obligation to pay taxes. But, you know, I don't, I, you know, but so for companies, know, so, you know, I, you know, I think this is interesting too, because I've actually spent.

A bit of time, I was fortunate enough to be invited to this organization called the European Entrepreneur Forum. And it's a network of about 100 CEOs of unicorn companies who get together once a year, and in smaller groups throughout the year, to talk about what they as a union can do to give back. And they do have a very different philosophy that the tax structures are not as encouraging to companies to donate as they are in the US.

of these countries pay a lot more taxes than we do and have a lot more social services than we do. They're horrified, you know, as are we, at the expense of health care in this country, that we do not have universal culture, that our public schools are terrible. You know, anyone, I I sent my kids to private school. I was fortunate enough to have the means to do so, but it was because I sent my kids to private school, I don't have a ski house. But I was like, like, you know, but you know, I'd rather, that was the best money.

I ever spent in my life because the public schools in San Francisco are not that good and you know I had the opportunity and anyone I know who has that choice that's what they make. you know the health care is so expensive when I was I now have sort of a hybrid role where I'm an employee of Pledge One Percent. so and one of the reasons I became an employee and not just a consultant is because I needed better health care. You know we were paying three thousand dollars a month out of pocket for health care that covered nothing.

You know, nothing. know, so anyway, you know, I'm sort of this is a roundabout way of answering your question, but in Europe and other countries, you know, they don't have the need for as much. The ones who do it are so happy that they did. And there's, you know, for instance, this is in your space, Rob Klarna, the founder of Klarna, you know, there are two founders, but he left the one of them left to start a foundation because he thought, you

helping people buy more shit, me, I don't know if you could see, buy more stuff, buy more stuff and you know I want to have a greater impact so he's taken all his money and put it into his own foundation that's focused on climate initiatives. And here this is another thing that I'll say is that every single company has to do something about climate and all of our Pledge One Percent member companies do.

Rob Curtis (25:29)
Mm-hmm. That's fine. Yeah.

The world is changing. AI is about to come. We're seeing AI agents enter the workforce. And I think many of the people that we talk to or that we hear from work in big companies, the Fidelities of the world, the IBMs of the world, where they're to wonder what the world might look for them if they leave. And I think there's almost a fear of moving away because the world's changed so much. And so I wonder, for somebody who's trained like you have in the law and is thinking about their next

steps, what would you tell them about the opportunities that are available to them as a lawyer that perhaps aren't just practicing the law?

Jan DAlessandro (26:24)
I sort of early on realized that for me personally, I'm a natural partnership builder. You know, the law firm, you know, didn't want me to leave because I was so good at bringing in business, you know, but it wasn't what I wanted to do. And so I think that, you know, in everything is like, you know, be honest with yourself about who you are.

you know, if you're someone who really is an introvert and prefers to just, I mean, you know, just...

you know, work on documents, that's fine. We need people in the world who love to do that. In fact, like one of my best friends from law school who's not an introvert, but she loves, she became a partner at a bankruptcy, she was a bankruptcy partner at a big New York law firm. For me, when I worked at White & Case in New York, I wanted to like shoot myself in the head when I would get these like 800 page documents. She loved it. She loved being smarter than everyone and finding the thing that no one else saw. I wanted to kill myself.

And she's not a introvert, but she loved it. So there's a place for everyone. And I think that in anything that you do, you've got to be honest with who you are and do what you love doing. Do what comes naturally to you. I feel so fortunate that sometimes my work doesn't even feel like work. I would probably do what I'm doing even if I wasn't getting paid.

I do have financial needs that must be met. So it's important to me that I have jobs that do pay me, but I would probably do a lot of what I do anyway. The other thing is I think you mentioned AI, and I think that's really important because...

I live in San Francisco. San Francisco, we've had a tough time with the homeless problem and everything else, but I believe AI is what's going to bring this city back. anyone who is, we should be scared about AI because there is, it is massive, but it's here to stay. It is going to change the way that we do everything. And if you look at, I don't know if you know this company Anthropic.

I love their ethos, right? They're amazing, right? Like their mission about like, you know, creating responsible AI and that they're about trust and safety. That's so important. because they're, you know, AI does have opportunity to create, put in the hands of wrong people and it will be put in the hands of wrong people. bad people, you know, we went through this when I was at AOL, like, you know,

Rob Curtis (28:10)
I use them every day.

Jan DAlessandro (28:32)
I think it's the same thing that for people looking to make a career switch,

look at what you're spending your free time doing. You know, if you're someone who spends a lot of times outdoors, know, hiking, biking, surfing, whatever, you know, there are jobs to be created in anything, you know, anything that you love to do. There's a job, somebody's doing it, you know, and so, and it doesn't have to be, that's just an example. If you're interested in the arts, maybe look at that. Looking at how AI is going to be used in the arts is fascinating. You know, my husband is a filmmaker and, you know, and he's worked in advertising in this and that to think about just, I don't know, I would say,

anyone today who's looking for a career switch, go take a course on how AI is being used in the industry that you care about. There's going to be so much opportunity.

Rob Curtis (29:15)
Exactly.

Yeah, and I think, you know, a lot of people are stuck in the...

in the mindset of how to stop that. I think, you know, very much adopting a kind of yes and mindset to AI is it can accelerate lots of things, but I think it still creates lots of uncertainty for folks. And unfortunately, the fog of war is pretty thick at the moment.

Jan DAlessandro (29:25)
Yes, exactly.

Yeah.

as a lawyer, you're trained to think critically, right? That you don't take things at their face, right? When you're presented with something, you know, whether it's, you know, a document or something that somebody says to you in a negotiation.

you're trained to think about that and not take it at face value and see how, okay, how can you take that and turn it into

something positive for both of you. If you're a deal person, you're negotiating with the other side. As a leader, you're negotiating with your team, with your boss, with your colleagues. If you're at a tech company, you're negotiating with the product and engineering team to build what you need for your deal.

if it makes sense, know, for the company, all of that. So I think negotiation skills and critical thinking skills are needed in any role. And I think that, you know, lawyers should not undermine that because hopefully if you're good, you know, you're better at that than almost anyone.

Rob Curtis (30:28)
one of your favorite quotes is, you're playing small doesn't serve the world. A Marianne Williamson quote. So for a person that's feeling like they need to shrink themselves to move forward,

What would you say?

Jan DAlessandro (30:40)
Well, I would say is look in the mirror and say, how does this serve me personally and how does this serve the world? It doesn't. If you think that obviously you've made it this far in your life that you obviously have skills and passions that...

that can be used to help anyone, including yourself. So I think when I, why I love that so much is it says, you know, we have to be honest, like we all face moments of insecurity and despair and thinking like, ugh, know, if you leave a job or lose a job or your child is not nice to you one day, now my kids are older now and they're so nice to me now most of the time, but like when they were younger, they weren't always, you know, and you thought, think, or somebody else isn't nice

to you. You think, ugh, you know, but you think like that you can't live in that place. You know, you have to live in a place and I just, you know, we've I've started meditating. You know, there's a lot of different, you know, coaches and this and that. But, know, what it what meditation practice does for you is it teaches you to focus on gratitude.

forgiveness, forgiveness of yourself and focusing on what do you like about yourself? What are you grateful for? What do you like about the people around you? Cheryl Sandberg, when she lost her husband, she wrote this great book and she said that she started a gratitude journal every night writing down what she was grateful that happened that day, pulling herself out of the depths of despair of losing her husband. And how it was like step by step that when she would even write, I was grateful

for that piece of chocolate cake that I had. It made it taste even better. Because she's like, I'm going to write about this in my journal tonight. So she almost got to experience the joy twice.

we're celebrating one of my best friends tonight who's the most generous person you've ever met. And people, there's parties for her every single night because people want to give back to her because she gives so much to so everyone else. And that's sort of how I feel about every day.

every year, you know, we try to come up with our New Year's resolutions. I always come back to the same one is assume goodwill and spread good cheer. Like, and I think that's one of the worst things in this world is when people think that someone has, you know, treated them badly or dissed them. It almost never has anything to do with you. You know, it always has to do with like, maybe they got in a fight with their spouse or their...

somebody got sick or they lost someone, you it has nothing to do with you. And so just like don't take things personally like that and just think about how you can, you know, make that person feel better.

Rob Curtis (33:09)
That's awesome, Jan. Thank you so much.