Tips on Managing Risk from a Startup Veteran & Angel Investor

Adam Nash, CEO & Co-founder at Daffy, shares his thoughts on risk management, fintech trends, what angel investors look for in startups, and more!

In this episode of Startup Success, we welcome Adam Nash, the CEO and Co-Founder of Daffy, a not-for-profit platform that empowers people to be more generous more often.

Adam shares his valuable insights on managing risk and provides lessons for early-stage founders. Additionally, he delves into the intricacies of the fintech sector, and he sheds light on what angel investors look for when considering an investment in a startup.

Join us with Adam Nash as we:

  • Talk about managing risk at startups and valuable insights for founders
  • Discuss the landscape and future trends in the fintech sector
  • Evaluate the value drivers angel investors look for when investing in startups
  • Share Adam’s favorite Steve Jobs story from his Apple days (a must-listen-to for all founders!)

Adam is a 32-year veteran in the business world and has helped drive growth and innovation at companies like eBay, LinkedIn, Dropbox, and Wealthfront. He’s also a successful angel investor with investments in an astounding 129 startups!

This discussion with Adam Nash comes from our show Startup Success. Browse all Burkland podcasts and subscribe to the show on Apple podcasts.

Find Adam on LinkedIn and visit Daffy.

Episode Transcript

Host – 00:00:01:
Welcome to Startup Success, the podcast for startup founders and investors. Here you’ll find stories of success from others in the trenches as they work to scale some of the fastest growing startups in the world. Stories that will help you in your own journey. Startup success starts now.

Kate Adams – 00:00:19:
Welcome to startup success. My guest today is Adam Nash, the CEO and co-founder of Daffy. But I want to point out that Adam has a long history in the Valley. He’s worked Ebay, LinkedIn, Dropbox, Wealthfront. He was CEO and founder. He’s also a prolific angel investor. So I know today is going to be a great conversation. Welcome, Adam.

Adam Nash – 00:00:44:
Thank you for having me, Kate. Glad to be here.

Kate Adams – 00:00:46:
Thank you. I want to get into your background. I know you have a lot of great stories and you can share a lot of experience that will help startup founders today. But I first want to talk about what you’re doing now with Daffy because it’s a really interesting platform and I think it is of great interest that this is where you are now. So if you could give us some background and what led you to found it, that would be fantastic.

Adam Nash – 00:01:12:
Well, yeah, I think the founder journey is always a complicated one. I don’t know if there’s any one specific moment. I did set out in 2020 to start a new company and I think, like a lot of founders, I had that Google Doc of all these different ideas I’d been building for years. I think that Doc had 82 ideas on it, by the way.

Kate Adams – 00:01:31:
That’s impressive.

Adam Nash – 00:01:32:
And they were not all good. They were not all good. But there was one of the lists on that document were lists of great financial products that hadn’t been reinvented yet. Like, we’re more than a decade now into this kind of fintech revolution that really hit the Valley. Obviously, Wealthfront was very early on that and got to run that and see it firsthand. But as I thought about things going forward, I was looking at this list and there was the product there, a very sleepy product called the Donor Advised Fund, which I had personally had, which was all about it’s a tax advantaged account for giving. I mean, we have accounts for retirement, like the 401k, we have one for college, 529. It’s just this arcane little product, but it turns out the wealthy use it a lot. And maybe it was the pandemic, but talking to my co-founder, this idea of like, wait, what if we took all this energy that we’ve put into saving and spending and investing and shopping, and what if we put that same energy into giving? Right? And actually, the more I dug into it, some ideas you dig into and you feel like they’re fighting you, and then some ideas you go into. And the more you go into it, the more you get conviction, the more you’re like, wait, this is better than I thought. You look in like, oh, wait, how big is the audience here? How many people give to charity regularly? And you discover it’s like, no, it’s like 60 to 70 million households in the US. every year. That’s a big number. And wait, is it a lot of money? Oh, actually it’s almost half a trillion a year, right? It’s a bigger percentage of GDP if you measured it that way, than agriculture, right? And you’re like, oh, this is a huge sector. You’re talking about trillions of dollars over a decade. And it seems materially important to people. And so I don’t know if it was the pandemic, et cetera, but my co-founder and I set off to found kind of a modern platform to help people give. And we set this mission. We have this audacious mission. It’s very simple. I’m a very big mission vision kind of guy and leader. But the mission was simple. We’re going to help people be more generous more often, and that’s what we set up Daffy to do. So daffy. This is one of the daffy T-shirts. Not the only one, the logos on the back. But Daffy is the donor advised fund for you, right?, it’s a nonprofit, and you get this fantastic app that has every charity that’s legal in the U.S. in it. And anytime you want to put money aside for charity, you set a goal. If you want to give $500 a year to charity, $1,000. Daffy wants you want to put aside $10 a week or $50 a month, and then anytime you want to give, you have the perfect app to do that in your pocket.

Kate Adams – 00:04:04:
First of all, it’s so great to hear that there’s that much giving going on in the world, so that’s uplifting to hear. But I like how you made it so easy for people and so organized. That’s the one thing that I’ve always found difficult with charitable giving. I feel like I’m all over the place, and there’s not an easy way to do it. It sounds like you’ve really solved that problem.

Adam Nash – 00:04:28:
You’re spot on. It’s amazing how many members tell us we’ve only been out about a year and a half. We launched at the end of 2021. We raised our seed at the end of 2020. Yeah, a lot of people. It’s amazing. I always believe in customer development, user research, going out and actually talking to real people. And I did that before building the product here at Daffy, talking to dozens of people across the country about giving, and you hit on one. That actually was a surprise to me. No one is happy with going through donation receipts at the end of the year and just have like I’m telling you, if you’re younger, everyone has a Gmail search at the end of the year to find it. And if you’re older, you print it out and put it on a folder on your desk somewhere. I have this one.

Kate Adams – 00:05:08:

Adam Nash – 00:05:08:
But it’s funny, when you do use your research, you discover, like, there are these high level things like Daffy, what we’re excited about is just I mean, honestly, it’s probably pretty obvious to anyone listening that Acorns on the board of, has helped millions of people save. Like literally millions of people now use Acorns to get into a healthier financial place. Just a simple app that started with just saving your spare change. I mean, for us, it’s like, imagine if millions of people were putting money aside every week or every month for charity. Just the transformational difference that it would have on the industry. But sometimes it’s a simple thing. So all the donation receipts in one place, just setting a giving goal, just like a budget on just having a goal. This would happen, by the way, when LinkedIn went public back in the day, my accountant ended up asking me, how much do you plan to give to charity every year? And I was like, no one’s ever asked me that question. And yet it changed my giving, right? Having this goal, it’s like anything in budgeting, like, once you have it, it gives you freedom. And I do think that most people are trapped in this very transactional attitude. Someone’s running a marathon, someone’s volunteering, someone invites you to a benefit, your kids are going to a school that’s raising money, and they ask, and they do that. I’ve been on the board of nonprofits. They do that because they have to. That’s how the system works. But I don’t think that really gets to the heart of how people want to give. I think having an act of service where you intentionally set a goal for your giving, that’s right for you and your family when you pick the organizations that you support and then you support them regularly every year. I mean, I love in the moment I made the app, it was a very high priority for me that someone be able in the moment that if they see, if they get inspired to give, just make it easy, just let it happen, right? Like all that work we’ve done in user experience, like how to make apps so fast. Shopify is good, it’s too good. I learned this. But Amazon is good. Like, all these shopping sites are good. But we try to make it that easy to give. But the intentionality of it, of picking the organizations you support, having the peace of mind of knowing that if you give money to this organization every year, that it’s going to happen. I mean, these are easy things. Recurring donations, recurring contributions, search. I mean, we’ve done this in other areas. It’s just a very sleepy sector despite its size. Somehow a lot of the energy and fintech, et cetera, hasn’t gone to giving yet. But hopefully we can change that for the better.

Kate Adams – 00:07:34:
I think you are going to change it. I mean, you’re really speaking to me in the ease and the organization around it, because I’m one of those at the end of the year, I’m like, oh no, I didn’t give here. I thought I gave there. Where’s that receipt I printed? Let me do my Gmail search so I get it. And I also like something you said that you talked to users, you did a lot of research before you built this product, and you’ve had all this great experience. I’m sure you’ve brought that in to what you’re doing now at Daffy. Can you share some other examples of things you’ve done based on your success at LinkedIn, Wealthfront, other companies that you’ve brought into now, your building of Daffy? I think that would help our listeners a lot.

Adam Nash – 00:08:20:
There’s so much, I think that it’s part of the founder journey. Like whether you’re early in your career, middle career, later in your career. You can’t help it. You’re the founder, you bring all of that in, right? Like, you leave it all on the field, but it’s all of you. And I have been fortunate to work with some amazing people and I don’t want to embarrass anyone. I mean, the truth is, for me, despite the fact that I was a startup at the was at Apple, when Steve Jobs came back and I’ve written about those experiences, et cetera, a lot of the way I think about startups, that really amplified it was a combination of my first role in venture of seeing the other side of the table. Like what the venture capitalist experiences, hearing pitches, making decisions, term sheets, board meetings. I got a rare opportunity to do that in my 20s. And even though I decided not to be a VC professionally, full time, it affected the way it always helps, I think, to see the other side of any transaction. It’s easier to sell to someone if you’ve been the buyer. It’s one of those things. LinkedIn, for me, was very formative, and that’s in no small part to the fact that Reed Hoffman is an amazing entrepreneur and strategic thinker. And I get to count him as a friend and then a colleague and someone I’ve worked with multiple times. But one of the things that we used to always talk about at LinkedIn was how to think about risk. I mean, look at LinkedIn’s trajectory. It just hit its 20th anniversary. It’s more than 10 billion in revenue. I mean, thousands of people work there. No one even remembers the fact that no one thought that was a good idea. Almost no one. Like, why would I upload my resume if I’m not looking for a job? I cannot tell you how counterintuitive that was to everyone.

Kate Adams – 00:09:53:
You’re absolutely right. I remember that.

Adam Nash – 00:09:55:
But Reed has such a clear thinker. But we used to talk about risk. I know Jeff Bezos is famous now because he has his model for two types of risk and one way doors and that’s all great. I think Jeff is amazing and I don’t know him as well, but he’s obviously impressive on a million dimensions. But we used to talk about risk differently at LinkedIn and it really stuck with me. And so I teach my teams this at Wealthfront now at Daffy. I really think the problem with risk is that at a successful scaled company, big public company that’s working customers, they have a different view of risk and they have to necessarily because they’re playing a different game than a hypergrowth startup. Like if you’re a founder at a hypergrowth startup, there is too much to do and not enough time. And by the way, you have a limited window because there’s only so much cash in the bank and you’re not making money yet. So we tend to talk about these three types of risk. And so I still think of it this way, and this is a little bit skewed towards hypergrowth tech startups, very much the Valley thing. The three types of risk I tend to think about are fatal risk, painful risk, and embarrassment risk. Fatal risks are easy for a startup because you really are on the edge of going out, of not being around, right? There’s no guarantee you’ll be around to fight the next battle. And so knowing what could kill your company in that window, usually a lot of that’s financing in the beginning, so let’s be clear. But knowing what fatal risks are and avoiding them is critical, right? This isn’t like a video game where you get multiple lives. There are some risks where if you get them wrong, it’s just over. There are painful risks. These don’t kill you, but you only have maybe so many shots on goal. If you get this wrong, it’s going to be very expensive to reverse it or it’ll be very expensive, maybe just in time commitment to take many of those shots, right? And so painful risks are a big deal, but they’re not fatal. It won’t kill you, but you can’t handle too many of them. And then embarrassment risk, of course, is really an artifact of smart people and sometimes egos, sometimes you’re just wrong. And so the defect that a lot of smart people have and I’ve spent a lot of my career with a lot of very smart people. The problem with smart people is they over prioritize embarrassment risk, when really founders should spend no time on that, oh my God, no energy. Like move faster, like be wrong, great, learn something, go to the next thing. Obviously a bad experiment is anyone that you can’t learn from, but as long as you’re doing a hypothesis, you go out there, you’re wrong, get over yourself, you’re going to get a lot of it wrong. Maybe it’s because I liked baseball as a kid. I always talk about batting average and slugging percentage and you’re going for slugging percentage, right? And guess what? Home run hitters sometimes have a great slugging percentage and they strike out a lot. Doesn’t matter, not in the startup world. Slugging percentage what matters. And it’s great because there’s more than four bases in business. You can only get four bases in baseball, but if you get the right product piece, right thing, it’ll make up for 100 errors. And so my advice to founders around risk is always to don’t spend any time, if you can avoid it, arguing about embarrassment risk, et cetera, but push yourself to take more painful risks, right? Usually the problem you have with a startup is time. And if you’re overly conservative about taking risk, you’ll only get a small number of shots on goal. Sorry, I just flipped sports, but whatever. I’m not really a sports guy, so you have to forgive me. I’m an engineer. But the real problem for founders is they worry too much about embarrassment risk and they do not take enough painful risks. And so at Daffy, I know it’s counterintuitive, especially in the space around giving, but we really push a team. We iterate, we ship things, we listen to customers, we build things. Sometimes they make a big difference, sometimes they might be a puzzle piece that fits into the future. But one thing we don’t spend a lot of time at Daffy is worrying about embarrassment risk. What we do, do, is push ourselves to innovate, right? And when you innovate, you’re doing things that are unknown, right? Like, will customers love it or not is always the ultimate bar.

Kate Adams – 00:13:51:
I like how you framed those risks, especially embarrassment risk. I’ve never heard it referred to that way, but it makes a lot of sense. And then the fact that you talked about how you’re iterating a lot at Daffy as a fintech startup. Let’s talk about that, the fintech sector, for a second. We have a lot of fintech founders who listen to this show. You said something to me when we first joined that reminds you what’s happening in the fintech sector right now a lot about what happened with Web 1.0. Can we touch on that? Because I found that interesting.

Adam Nash – 00:14:26:
I can’t help it like you get to a certain point in your career. What’s that old quote like? History doesn’t repeat, but it sure does rhyme a lot. And that happens a lot in software, because the first principles, the fundamentals of what’s easy or hard in software, there’s theoretical capabilities and then there’s the reality of what machines and networks can do in your day. And it’s just different. This thing I love about tech, every five to ten years you get to relook at the same problems and go, oh, we can solve that differently now because computers are faster or more people are connected or we have devices. And so these transitions happen. And it happened famously with Web 1.0 to Web 2.0. And I saw this because I spent a long time at Ebay in the early days with web 1.0 and building one of the first scaled marketplaces and then going to LinkedIn, it affected my thinking. LinkedIn was web 2.0 user generated content, viral distribution. But fundamentally, I always thought of LinkedIn as a marketplace, right? How does talent meet opportunity? How do companies find people to work there and vice versa? And how you get marketplaces started and how you build them is a really hard topic. But a lot of web 2.0 was built on learning what did and didn’t work in web 1.0. I mean, obviously it was a famous blow up with the bubble bursting. But the truth was there were some fundamental flaws in web 1.0 businesses that web 2.0 then attacked and effectively defeated, which is why we’ve seen so much scale success. We don’t talk that much anymore about, but LinkedIn has been a big deal for a while. Obviously, I’m too close to that to be impartial, but it’s a big deal. And so I see the same transition in fintech right now. I think that a lot of early fintech companies, like early web companies, just took something online offline and then put it online. That was a lot of web 1.0. But it turned out that web 2.0 was very defined by novel products and features, things that couldn’t exist offline. Right? LinkedIn, monster was like, yeah, we can do job postings and put your resume online. LinkedIn imagined this different concept of a professional network. It was just transformationally different than what the job experience or what recruiters did previously. And so I’m looking a lot now in my own portfolio, my own efforts for transformational products, things that couldn’t exist offline or in the previous world. I think going from single player to multiplayer is another thing that was a big difference with web 2.0. Most the early applications were one player games. You do it yourself, it’s a tool. You go online, you can do it online. Great. Sorry, I don’t know if that’s a great podcast thing to do, but no. Awkward. But no. So a lot of the early web 2.0 applications thought, fundamentally, how do people come together? How do they create content together? How do they interact together? And it’s been harder than we thought. Let’s be clear. As an industry, we definitely some mistakes and problems have happened. If you’re going to build a transformational product, thinking about how to bring multiple people together is always more powerful in so many ways. And I think fintech mostly has launched single player products. And I’m very excited about financial applications. I mean, let’s be honest. Like the last exciting multiplayer application that came out of traditional financial services, this is what, like the joint account? Come on. All right, complicated enough. And then of course, the third thing that I get very excited about is the generational piece or the age piece. Fintech who would trust their money to software? I mean, when I started Wealthfront. That was the big question. And the answer turned out to be young people. First of all, less money, there less to risk, less brand loyalty. But also they grew up in an era of technology. They trust technology fundamentally differently than people who are used to other systems. And so a lot of early Fintech applications I mean, I did this too, but I mean, they were all millennial pitches, right? Like, almost everything you heard is a millennial pitch.

Kate Adams – 00:18:03:

Adam Nash – 00:18:04:
And now though, I think the Pandemic changed everything. I think we pulled forward my parents, who still going to the bank, that’s within their 70s. They used to take literally from their doctors, but they would actually deposit checks at First Republic on a regular basis. Pandemic got them no, can deposit checks in the app, right? They can do everything from an app, from service. And so I’m just excited about applications now that are multigenerational, that hit people for real use cases. I think we no longer have to pigeonhole Fintech to one small market segment. And more importantly, I don’t think you can anymore. I think the game has moved. These are all the things I’m excited about. Obviously, I’m talking my own book to some extent because Daffy is built around some of these concepts. Like, we rolled out our family plan last fall, and it sounds so obvious. Like, of course, if I have children, I have siblings, my parents, maybe we all want to have a fund where we can donate and discuss and give together and talk about the causes we support. I mean, the fact that my kids now, every time I make a donation, they get an alert on their devices that lets them know that the family donated this cause it comes up at dinner. I didn’t know we give to this or why do we do that? It’s amazing. As a parent, that’s what I’m excited about in the next decade for fintech. It’s what I look for.

Kate Adams – 00:19:17:
You were spot on in so much, especially the acceleration that the Pandemic caused and then what lies ahead. I really like how you summarized everything. One thing that caught my eye is that you’re an active investor, angel investor, I think you said. What, you’ve made 129 investments to date, is that correct?

Adam Nash – 00:19:40:
Yes. If you include ones from 2023, then yes, that’s correct.

Kate Adams – 00:19:44:
Yes. Everyone tells me they’re an angel investor. I would say you’re the real deal.

Adam Nash – 00:19:50:
There are few of us now this year than in previous years.

Kate Adams – 00:19:52:
Exactly. That’s very well said. So many aren’t anymore. But tell us what you’re looking for right now and kind of your investment philosophy based on your background. I’m sure you can spot some trends and are really good at picking out winning founding teams and whatnot.

Adam Nash – 00:20:11:
Well, this is one, again where I have to give credit to some great people that I’ve worked with. But one of my takeaways from working with so many great venture capitalists in multiple capacities is as an investor, it’s a different than being a founder. As an investor, I know this is going to sound counterintuitive when we’re talking about venture capitalists, et cetera. It does require a degree of humility to know what you don’t know. And you’ll find that the great investors I don’t want to say they stick to their knitting, but they have a certain type of business, a certain type of sector, a certain type of go to market that they have a lot of understanding. Maybe they have deep operational experience in that area, or maybe they’ve invested in these companies before. And so as an angel investor, I try to do the same things. But not surprisingly, I like to think of myself as a smart person. I probably comment on too many things on Twitter that I haven’t directly worked on. But as an investor, I try to look for small things. I’m a seed stage investor, right? And so I tend to mostly look for companies, founders, products, where I look for three things, right? One is in fintech in particular, I look for products that actually deliver value. There’s a lot of ways to make money in the world, and not all of them actually involve creating value. And I’m okay with that. There are frivolous things that people spend money on. That’s okay. But when it comes to building a durable business, you’re a seed stage investor. You’re thinking about a company that over the next decade could become one of the largest in the world. To me, the product fundamentally has to have real value. And in finance in particular, this is almost ethical thing for me. I teach this class at Stanford in personal finance now. And so for me, I look at the product value. The second thing I look for is authentic founder product Fit, right? Why do they want to do this? I’m okay with people who just say this is a great business. I want to build this business. But if that’s the only motivation is money and success, I hate to break to all the founders out there, there may be some easier ways to make money in this world than founding a company. I’m just letting you know. I’m not sure they have the same upside transformation for your life, but there are certainly easier ways to make money than founding a venture backed startup. But I look for something more authentic about why they’re building the product. Why do they understand this problem? Maybe it’s old fashioned, but through my career, the founders I’ve been most impressed with have been ones who saw a problem and then they went to solve it. Right. I think that’s a big deal. And then of course, the third thing I look for is I really dive into the products for the go to market because it ties to the economics, right? I want to know. I’m an engineer, but I probably talk more like a marketer these days. I don’t know how that happened through my career, but the basics of understanding who you’re targeting, what their options are, how they think about that purchasing decision. I mean, in Enterprise and B2B, when you’re talking about companies, there’s a very specific operational structure that will scale to deliver a venture class business. Consumer is different, but also has ways that you think through that in that process. But I have to see the glimmer. Look, I’m a natural optimist. It’s in my profile. I literally think I’m wired to be inevitably optimistic. And believe it or not, that’s not always great as an investor because I almost always want to take the founder’s side. This could be big if right, if this breaks our way, et cetera. And some of the greatest stories are that way. But I do have to be able to squint my eyes and kind of see the future in the distance and go like, oh, that could happen, I could see this and some of that. Just the market size. Sometimes that’s the go to market. I mean, acorns to me. For example, even the early days, the idea that some company would use a mobile first approach to saving to capture a large audience wasn’t that hard to believe if you were a believer in smartphones and how that ecosystem was going to play out. And one of my roles at LinkedIn was building out mobile. I was the executive at LinkedIn at one point that had to come forward and say, yes, I know, I know that less than 1% of our activity comes from mobile today. I said this in 2009. I said within five years, I think it’ll be over 50%. And it sounded insane to most people at the time. But not only did it turn out to be true, it left me with this strong feeling that there was a lot of opportunity to be had in the next decade around Mobile. That it was going to take time for people to absorb that the computer was no longer the most important device. But it was this one we were carrying around effectively. 24/7. So I look for those three things. Like I said, I look at the value of the product, founder product, Fit, and then kind of the go to market and long term economics. Will this build a venture class business?

Kate Adams – 00:24:42:
For any founder listening? I mean, those are three things that they should be paying very careful attention to. And I like how you weaved in that story about LinkedIn and making the shift to mobile because when you talk to companies like LinkedIn, that was a big shift in thinking, right, that people were going to start consuming the product on their phone. And we were all so surprised by that. But look, I mean, I think I use LinkedIn now on my phone more than my desktop, but. It’s that big shift. And as we wrap up, always ask guests to share a piece of advice with founders. But if you could weave in another story like that, I mean, I just think that would be great. Maybe from your time at Apple with Steve Jobs or something, because that was so spot on about what a huge change that was in the industry. That would be great.

Adam Nash – 00:25:37
Well, I mean, I’m happy to tell stories, and I do write about them on my blog, et cetera.

Kate Adams – 00:25:42:
Oh, tell us your blog. Where can listeners go find more of your stories?

Adam Nash – 00:25:46:
Oh, it’s a very obscure name. It’s just

Kate Adams – 00:25:49:

Adam Nash – 00:25:49:
You find all these product management articles and stuff. I’m happy to share stories. Like I said, for me, business history and these experiences, whether they’re first hand, et cetera, they get to the heart of the fact that there are elements to business and building companies, et cetera. You’re not alone as a founder, big turnarounds, et cetera. Like these things, bad things have happened before. This is my fourth, in some ways, tech recession in my career, going from the early 90s when everyone was laying off and HP did their first layout. I was in college. Terrible job market, early 90s, obviously, the bubble bursting, financial crisis, now this excitement. And so there are some patterns, but if it helps, I’ll tell one. I mean, always a crowd favorite. I wrote about this because it was very influential to me as I was there at Apple. So I had interviewed at Next when I was finishing my graduate degree, a lecturer at Stanford, was already working there, referred me in, Craig Federighi. Oh, was the guy interviewing me, who’s now back at Apple and running all software, et cetera. Amazing. Still energy, the hair, the energy. Same guy, I’m just telling you. And such a great guy. He’s such a great person in so many different ways, I will tell you. So I was interviewing, and the process halted, and I got this cryptic message, like, we’ll talk again after winter break. But it turned out Apple bought Next, or did Next by Apple, I don’t totally remember, but whatever. Anyway, the point is, I ended up taking my first role full time at Apple, working on I actually went to the old Next buildings, and so I was there when Steve kind of came back. I saw Steve with Next, and I saw Steve at Apple, and obviously he didn’t pay a lot of attention to me. I was a 22 year old engineer, although once or twice I did try to pin him with a question. And sometimes that works out, and sometimes it doesn’t. But I will tell you, I remember that speech I wrote about it when he passed away, because Steve was a mixed personality, et cetera. But as a leader, sometimes he could be so spot on. And I remember at the time, I know it’s hard to remember. But in the 90s, there was no hotter computer executive than Michael Dell. He was asked, of course, because Apple every newspaper. When I took my job at Apple, literally everyone looked at me like, are you saying Business Week? Literally saying the fall of an American icon? Like, this thing is going bankrupt. And I remember someone asked Michael Dell, I think, on a talk show or something. I don’t remember, what would you do with Apple? And Michael Dell on this public interview, said the equivalent of, like, some things you can’t fix. I don’t want to misquote him. He’s a great entrepreneur and leader in his own right, but he basically said, Some things you can’t fix. I would think about just returning cash to the shareholders or something like that. I mean, you could not get worse. That’s literally like and so Steve called a full meeting of the Rhapsody team. That was the team I was on. That was what became macOS 10 and iOS of the future. OS but it was called Rhapsody at the time. Whole team. So a picture, like 200 people called together, put Michael Dell up on the screen and said, michael Dell, who is one of the greatest technology leaders right now, et cetera, thinks that every day you wake up, you kiss your loved ones goodbye, you come to work, and you destroy value. He thinks it would be better if we all packed up and went home and just returned cash to shareholders. And you know what? He’s right. Because if we keep shipping more of the same products, the world doesn’t need more beige PCs. Compaq does. That’s great. Dell does. It’s great. The world doesn’t need more of that. And then he asked the question. He was like, do you know what BMW’s market share is, by the way? Sometimes when Steve asks questions you’re not supposed to answer.

Kate Adams – 00:29:15

Adam Nash – 00:29:17:
Everyone’s like, but you think you know how much BMW market share is? He said, you know what? It doesn’t matter, because no one cares. Because all you care about is the BMW you’re in or the one you’re watching drive by. He’s like, Apple exists to make product that people don’t just use, but that they lust for, right? And he talked about this whole thing, and I wrote about it because it sounds simple. And these parables, you can make business stories anyway. But this idea of this clarity for Apple that it wasn’t about market share was this amazing leader of saying, hey, we’re going to reboot this thing like we’re a $6 billion startup, and we’re going to have to work hard because this thing is going to go away if we don’t find a purpose. But he had this idea of differentiation. This idea of market share is not the measure, right? And actually, to this day, by the way, the reason Apple is so confusing to people is to this day, they still that genetic memory. They still don’t play those market share games. And this didn’t sink home for me until I was at Ebay, when Ebay had a similar situation and it had this choice. Like, is their destiny to grow in scale, to become a big ecommerce marketplace, just buy things just to buy stuff? Or is it the colorful, zany craziness of auctions and that engaging experience? But, like, pick a lane. And I remember at the time I was at Ebay, what I saw was that executives had a hard time picking one of the two. They wanted Toyota’s market share, but BMW’s design flair and margins. Like, Ebay wanted the high margins that come with that kind of focus and delightful product. But they also were 20% of ecommerce at the time. They wanted to grow. They wanted scale. And so watching how Steve handled that situation versus what I saw later in my career, these are the kind of things that you learn from, and it turns out to be invaluable because there always are ups and downs in businesses. And knowing how to handle them with your team, how to motivate around a growth opportunity versus a turnaround, there’s nothing that compares to actually seeing it done, whether it’s done right or wrong, it helps inform your future as a leader.

Kate Adams – 00:31:23:
Wow, those are great shares. And so spot on, especially with Apple. I mean, just the way you captured that today, people still lust after their iPhones and their IMacs, right? So it’s so true. So I wish we could talk for another hour, but since we can’t, I really want to encourage everybody listening to go check out Daffy, because based on all your experiences and the way you’ve described the platform, I think people will be very excited about it. Where do they go do that? Where do they get more information on Daffy?

Adam Nash – 00:31:58:
Yeah, so it’s as easy as going to You can go to, sign up. It’s free under $100. There’s nothing wrong playing with it. And like I said, I think you’ll find that having an app that makes giving more intentional is not just a financially smart thing to do, taxes and all that stuff thing, but it’ll actually make you feel better about yourself. But also say, you can just go to the App Store, type in Daffy. We were the first I know it sounds crazy for this decade, but we were the first fully functional donor advice fund in the App Store. So if you type Daffy into the App Store, you’ll find our app, download it, go through it, play with it. It will ask you some questions like, hey, what’s your giving goal for the year? Et cetera. But I think you’ll find it amazingly empowering to go through. And of course, we’re early. So give us your feedback. I would love to hear it. I’m just So feel free to contact me as well. Yes. And I’m happy, by the way, for your listeners or for anyone. If you want an invitation link to get an extra $25 to give to the charity of your choice, happy to do it.

Kate Adams – 00:32:55:
Wow, Adam, you shared so much wisdom, insight, a lot of great stories, and congratulations on all your success. But now daffy too I’m going to check it out. It sounds like it would be good for me and my teenagers to get on a platform like that to make it more organized and like you said, intentional. Right now it feels just too sporadic, too in the moment. So thank you for your time today. It was a great conversation.

Adam Nash – 00:33:22:
Of course. Thanks again for having me. Happy to do it anytime.

Kate Adams – 00:33:24:
Thank you.

Host – 00:33:26:
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