Best of 2024: Masterclass in Leadership, Innovation, and Resilience

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As we enter 2025, we can't overlook the valuable lessons 2024 has taught us. This week, I’m inviting you to join us as we look back at the most impactful insights from our incredible guests over the past year. 

Buckle up — this episode is a curated collection of the lessons, strategies, and stories that I believe resonated with you the most. From navigating rejection to building legacies, and from ethical investments to breaking stereotypes, this year has been a masterclass in leadership and innovation.

So, get ready as we dive into the "Best of 2024" and relive these powerful moments. Let’s get started.

Key Takeaway 1: Resilience Through Rejection and Growth – Failure is but part of the process

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To kick things off, we revisit a recurring theme of resilience. Some of the best stories this year came from founders who turned rejection into opportunity. 

Melanie Perkins, the co-founder and CEO of Canva, shared how over 100 VC rejections didn’t stop her from building a startup that soared to nearly a $49 billion valuation as of last October. Here’s Melanie on why persistence pays off.

Melanie Perkins: From over 100 VC rejections to building Canva into a $26B startup

Rick Baker, Blackbird Ventures (Clip):

How many no's did you get to record?

MP (Clip):

Yeah, more than 100. But then also that was from investors and then trying to find team members to join. 

So like trying to find engineers. So that was just like getting rejection just all over the shop. 

Yeah, so was a little frustrating, but worthwhile because it meant that we refined our pitch deck, meant that we ended up with the best people on our tech team that actually had the capability to build this crazy platform that we were dreaming up. 

So even though it was frustrating, I think in retrospect it was very valuable.

MP (Clip):

I think most people would probably give up before the 100th provision to their pitch, before the 100th investor their pitch to.

But it's just you have to believe in what you're doing before anyone else. Well, you have to keep on persisting and pushing through. 

And it's not easy. There's nothing about starting a company that's easy. It's like, by its very nature, it’s going completely against the grain, but it's so worth it. 

And if you enjoy a challenge, you don't get a better one than a startup.

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In a similar vein, Iman Abuzeid reminded us that rejection is a given when it comes to fundraising, but staying selective and focused on your vision makes all the difference. 

Iman Abuzeid: Rejection is the norm; tips for selective fundraising

Iman Abuzeid (Clip):

We were self-funded for the first year and a half, which I know is a very short period of time, it was just my co-founder and I who had put capital into the company. And then, raised our seed round in our first two and a half million dollars relatively quickly. Now, keep in mind, like, there's just an enormous amount of rejection that happens, even now, right? That seed round probably spoke to 80 investors, 71 said no. So, even at the series A, we were very established in California at that point, probably had 35 conversations, 32 said no. Even the series B, when I did the series B last year, Fantastic metrics and so on. Even then, it was, I think, spoke with 15 investors because it was pretty large check sizes we were looking for. So it was a small group. But yeah, 11 of the 15 said no.

So there's just like an enormous amount of resiliency you need to get through the fundraising process. Even if you have an amazing deck and an amazing business and great metrics and so on.

So, there were probably a couple of things that led to successful fundraising rounds. And I've raised almost $100 million over three rounds. First and foremost, be very selective about who you pursue. At the end of the day, fundraising is sales. And so I, as far as just the context of this overall discussion, I tend to only pursue investors that have already backed female CEOs. Like, wow, I'm not going to be the guinea pig. You know, it's 2022. Like, I don't, we don't need to be. I don't need to be and so there's definitely some selection that goes on there. Not to mention also, I'm looking for technology investors, marketplace investors, et cetera, right?

The second piece is just like, look, I know the statistics are bad. I think you mentioned less than 2 percent of venture capital is going to female. Yeah, the data's bad, it's clear, like there's a very clear structural bias in the system. But if you are a CEO who's pursuing your huge vision and ambition and your mission, you actually kind of have to compartmentalize and suppress that psychologically, right? Like you can't really focus on the 2 percent thing. You just have to go for it.

Key Takeaway 2: Pioneering in Business

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“Just because something hasn’t been done doesn’t mean it can’t.”

Next, we spotlight leaders who’ve dared to chart new territories. Julie Wainwright, founder of The RealReal, explained why first-movers need to embrace the unknown and listen closely to their customers. Let’s hear Julie talk about the courage to innovate and stay customer-centric.

Julie Wainwright: Just because something hasn’t been done doesn’t mean it can’t

Julia Wainwright (Clip):

I knew I wanted to go back and run an e-commerce business, and I wanted to do something I thought would be really hard for Amazon, because if it can be third party source, Amazon will do it. There's no doubt about it, and they'll do it better and they'll probably do it cheaper and then you're gone.

So I did have development of luxury products as a way, but I also knew I wasn't going to be able to compete with luxury brands. So I sort of tucked that away. And that's when my shopping exercise with my friend and web Lab, where she bought resale in a store in Menlo Park. The light went on. I'm like, that's it.

And that's when I started going around and figuring out how many consignment stores, brick and mortar consignment stores. And at the time there was something at 25,000. And how does eBay handle luxury goods? And the answer was poorly. And how big is that market? And you couldn't get real data, but look to be about eBay sales around that.

About 2 billion in luxury. But there was no real data. And then, you know, then you said, well, how do you sell jewelry where you don't open shop? Talk about unpalatable. How do you how do you sell art that maybe you bought at a gallery and you paid $5,000? The answer is you don't because no one wants to buy that art back.

You've got all this property that you had that you've been collecting. So that's what was the impetus was it was always like, we're going to resell things that eBay can't do because they don't have the authority because they're never going to really authenticate, and they're not a luxury experience. 

We can certainly be consignment stores because we can aggregate audiences and really have tried to get the optimal price for everyone using algorithms and and really technology where they can we can certainly beat pawnshops.

The universe we're in now. We've changed the way people shop. I wouldn't exist if customers didn't want me to exist. I mean, it's just like if you developed a product no one wanted, you'd be dead. World moves on, you know, and consumers vote every single day.

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Another standout moment came from this two-time CEO—Anjali Sud. Anjali transformed Vimeo into a B2B SaaS platform and navigated its IPO journey. And now she’s running America’s most-watched free TV service, Tubi. Her take on pivoting with purpose and reading market signals? You definitely don’t want to miss this—

Anjali Sud: Pivoting Vimeo into a SaaS platform and navigating public listing

Anjali Sud (Clip):

Vimeo started around the same time as YouTube and was sort of the ad free version, and there was definitely a period, you know, well before I got there where. It was unclear which, you know, which platform might ultimately kind of win. 

And the end of the day, when you're totally free for viewers, you can scale in a very different way than when you're paid, and because Vimeo was ad free, the platform couldn't monetize with ads, so you had to charge the creators.

And so Vimeo sort of stumbled on a SaaS very early on, it put the platform in a different trajectory. When I took over, it was really just to double down on that, and to say, by that point it was like, YouTube was YouTube, it was a behemoth, and,  and social media platforms were really taking off, and it was pretty clear that, Vimeo wasn't going to be a social media platform that made money on ads. So the question was like, okay, well, then what do we do. And we toyed with everything, I started to see organically in the data and in talking to customers,  more and more businesses were starting to embrace video, and this seems obvious today.

Yeah. But that was not obvious at the time, we thought we were inventing the future when we would say things like, one day everyone's gonna live stream a town hall and distributed teams are going to like, tune in instead of attending in person. Like that was not a thing.

And most investors were very skeptical. So I think it was really more about just like seeing the signs, seeing the signals organically of what's already happening in a platform, connecting that to maybe what's happening in a market. And that's sort of what led to the transition.

In my sort of six plus years as CEO, it was very much about executing that transition and doing it in a way that would help us scale. I think when I left we were about $400 million of ARR, but also be a sustainable, efficient, and enduring business that would be around and self-funding for years to come. And that's probably the thing I'm most proud of.

Going public was amazing and then hard when the stock price was coming down. And I learned a lot. What I feel like the impact I could make the most on the business was just putting it in a position where it's profitable today, no debt, plenty of cash on the balance sheet, significant recurring high margin revenue, predictable, and in a market that Vimeo can continue to invest and innovate and bring video tools to the world.

And so I think for me, probably what I've learned is sometimes the things that you think are the markers of success over time, over sustained periods of time, you realize it's usually those much more fundamental things.

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Making bold, life-changing decisions and taking risks – although not the glamorous side of entrepreneurship, this is where some of the most transformative innovations begin. 

Steve Chen, co-founder of YouTube, followed his entrepreneurial instincts every step of the way—from moving to Silicon Valley in 1999 to join PayPal, to then leaving PayPal to co-found YouTube. 

These pivotal moments happened quickly, and for Steve, the speed at which he acted was key to seizing these opportunities. 

Steve Chen: The ‘One-Way Ticket’: “If I have an idea, I'm just going to regret it if I don't take this opportunity now to actually try it out.”

Steve Chen (Clip):

Like many decisions, including starting YouTube or moving from Chicago to the Bay Area on a one way ticket back in 1999 to join PayPal. Those are generally life changing decisions that people dwell over for a while, but for me, usually they're made within six hours or something, like, let's do it.

I remember when I was leaving PayPal, it was whether or not, I want to be doing, I think it's 27, 28 at the time, and I was just doing the calculations and I was thinking, wow, it's going to be a while before I retire at 65 years old.

And so if I have an idea, I'm just going to regret it if I don't take this opportunity now to actually try it out. And even now when I'm giving talks to potential entrepreneurs, especially ones that have ideas ready in their heads and they're attending some of these events. My assertion there is always to them, it's like, look, if you have an idea, just leave your job and try it, and it takes three to six months.

It doesn't take a long time. It's not a huge sacrifice, and the earlier the better. Before you have kids, before you get married, before you have family, try out that idea, and if it doesn't work, I think you can pivot, you can pivot, you can pivot again, three to six months. Even if nothing comes out of that, even if you're not closing series A, B, C rounds, even if you're not going through acquisitions, it's a bucket full of just great experiences and great stories to tell that you're going to be collecting during that time, right?

Key Takeaway 3: Purposeful Investing

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As I often say, it wouldn’t be 2024 without discussions about AI. Conversations around impact investing grew tremendously last year, and our guests delivered invaluable perspectives about AI. 

For one, we discussed the catalytic power of purposeful investing and championing women in tech with Jack Selby. Here’s Jack on why we should invest with intention, especially with AI.

Jack Selby: Impact of capital and investing in art, film, and women in tech

Jack Selby (Clip): 

I think in Silicon Valley, we've done a very poor job at diversity in general, but I also would say not to make excuses. It's just kind of a notion. And so I think you'd be surprised by how many allies. If you just kind of raise your hand and people will engage.

But again, people are so busy and I don't think there's some sort of agenda that are trying to exclude people of any sort of type. And again, not making excuses, but I think that's unfortunately just how things are. All that being said, you know, we've gone out of our way to try to figure out a way to kind of help push things forward.

So for example, you know, I hired a woman that essentially is now the COO at our largest venture fund, Founders Fund. We've seeded three different funds that are run by women. And so I can't control how many young girls go into STEM training. But what I think you, my opinion is that where you can make the biggest bang for your buck is trying to figure out how you can allocate capital to female led managers. And I don't have a magic wand in terms of how to do that, but we've done that now with three managers that manage over a billion dollars. So I think that's at least a good place to start. 

AI is definitely the du jour topic that everyone loves to talk about. We can debate whether it's overvalued or not. My opinion on AI is that essentially it's a bifurcated world, so you have kind of the superpowers, if you will, so you have the Alibabas and the Googles and so forth, and then you have basically everyone else. 

And we can debate whether that's good or bad, but that's a topic for another day. But for everyone else what I'm actually surprised, pleasantly surprised by, especially in the context of this conversation, is that AI has become essentially a ubiquitous ingredient in the recipe that almost every startup uses.

And if you told me that was going to be the case five years ago, I would not have, I would have not expected that. So that, that progress, that acceleration is a great thing because it just makes efficiency that much better. And effectively it's a leveling of the playing field. So, you know, we, everyone can use this ingredient to make the process of whatever startup someone's making that much better.

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On a related note, a panel that I moderated in Stockholm on AI ethics and innovation reminded us that balancing advancement with responsibility is critical. 

AI Insights: Balancing advancement with ethics in AI investments

Nina Rawal (Clip):

I see AI as an enabler of solving those big problems that we as humanity face. I say that because, of course, that is the lens we invest through. I mean, we saw some of the previous presentations. You can do AI for anything, and I don't know how to speak to that because I don't understand that.

But I think through the lens of improving medical outcomes for people, I think it really the question really starts for us around what is, again, like the next pandemic, we know it will happen. We don't know what it will look like. And we are hearing over the past weeks that the world cannot unite around a new pandemic treaty and so on.

So we know what some of these very big problems that face humanity are. And that is really the goal we're trying to drive towards purpose, improving human health. And then using AI towards that benefit. I think it has to be in that order. 

And we've had so many conversations internally around kind of AI. And we get these questions, but what if this is early stage investing? What if the companies pivot and decide to do something fundamentally different? And I guess that's kind of our analogy, what you're saying you release something to the world and you don't know what the world will do with that.

As long as we are there in the boardroom, we are a so called Article 9 fund, we will do everything in our power to say that, that is not the goal here. 

Dorothy Chou (Clip):

So I spend a lot of time investing in undervalued markets with overlooked founders, and I think it's really important because Sandro and I've been both spent time in Silicon Valley and in Europe, and the vast majority of founders that are getting funding in AI are very one dimensional.

And it's a huge question and a problem about how we're thinking about what problems AI is being applied to solve first, to your point, because the truth is, like, usually what happens in Silicon Valley, where I spend a lot of time, is you just go the path of least resistance, which is going to end up in, like, personalized soda drinks before you get to anything in health or climate.

And so, the regulation is really helpful and important, but also for some investors feels like a barrier. I was just spending time at the Karolinska Institute yesterday. For example, how do we really think about directing investment and with policy help for updating some of these regs in regulated areas to facilitate the level of innovation to see?

Because I think most parents in developed countries are saying that they're afraid that their kids will be worse off than they are in many ways. And so AI can be helpful, but it takes actual work from a policy perspective, from an investing perspective to direct. The funding and the social change and the political change that's necessary for that.

Sandro Gianella (Clip):

I think just to say that I think this is particularly important in the next one, two, maybe three years, because I think we also all realize that the way the world is going to react, accept, and provide all of these companies and institutions that are pushing the frontier what I call sort of a social license not just to operate but to continue to advance.

I think is in large part going to depend whether we can tangibly show that real problems are being solved or that money is flowing into communities that can now solve problems that they previously couldn't. And I worry like Dorothy about the same thing where, I think it is going into kind of the usual places.

And I'm not saying it shouldn't go there and that's fine if you're solving that but I really hope with the advances of this technology, and what we've heard earlier today as well, is that it's going into really purposeful problems that we know are urgent and that we know need solving and that we're doing it in a way that advances the capabilities of this technology to push those that are developing it into, to really think about different things than they used to think before in the valley.

Key Takeaway 4: Leadership and Strategic Vision

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As the African proverb states, "If you want to go fast, go alone. If you want to go far, go together." Leadership in 2024 was all about partnerships, vision, and strategy.

Glenda McNeal from American Express shared timeless advice on building impactful partnerships and understanding consumer behavior. 

Glenda McNeal: Building partnerships and consumer focus as a growth leader

Glenda McNeal (Clip):

Partnerships are opportunities to really be strategic and add value and have an impact. And there are challenges when you try and bring brands together.

Oftentimes, however, that complexity is compounded by human behavior and personalities, right? And so the bigger part is really making sure that you understand the needs of the individuals that you're that you're working with. And sometimes, you have to understand that your values are not aligned or that the timing is not right.

I mean, I have a situation where I actually I have a portfolio of accounts And we actually bring in these accounts that we believe can really come to the table where, with, with the mindset of creating value together and going to market together. And we had an account we brought into the business and it would have fit everything that we were looking for.

It was in the travel industry and it was one where we felt our card members, it would resonate. It was a relatively, it was relatively new business model in the marketplace. And we had it in my account for about, my portfolio for about three years. And we really minded, but what we really found is that they weren't ready for partnerships, right?

They were still trying to figure out their own way of doing business. Their own way of being able to achieve the things that they wanted to with their customer base. And so sometimes the timing's not right. Now, we're about to re-engage in conversations with them because perhaps now it is the right time.

So not necessarily being aligned with values. And then sometimes the balance of trade, right? Sometimes the economics don't work. Sometimes it's not financially feasible. Sometimes you realize that the value that you envisioned really cannot be built around some of the key constraints that you have.

And you have to know, as much as you want to get a deal done, you need to know when to walk away and when it's not going to happen. It doesn't mean you walk away forever. It means that you walk away because it's not really in the best interest of either partner to move forward.

Key Takeaway 5: Breaking Stereotypes

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Finally, some of our most powerful discussions focused on breaking barriers and reshaping narratives. Shama Amalean Skinner, Former COO of Thinx, spoke about redefining women’s health and tackling stigma through advocacy and bold marketing.

Shama Amalean Skinner: Redefining women’s health and addressing stigma through advocacy

Shama Amalean Skinner (Clip):

We sort of reacted to what we were seeing from consumers and we reacted to what we were experiencing as consumers in the market. Right. And what I mean by that is what we were experiencing from the traditional had an underwear brands out there. So traditionally padded underwear brands were really buying into the stigma, really sort of marketing the discreet nature of their products.

It was all really doubling down on the stigmatizing narrative and we were these like young millennials coming in and thinking, Why? For generations we have been spoken to like this, why are we continue saying to speak like this about a normal bodily function? And so, this was phase one for us was how do we create this movement around destigmatizing periods?

And that was that journey into the subway, right? 

We wanted to go into the subways because we had just kind of mass ridership to be able to get some brand awareness around a new brand. And we just decided to go in there with a few images. We submitted a few images and one tagline, the tagline was Thinx Underwear for women with periods.

That's it. And we submitted this a sample copy and we got a letter back from the agency that owns the inventory in the subways, the ad inventory, and they said, we cannot approve this copy as is. And so we said, why? This is rather odd. It literally the copy that was just that one sentence. And so we got on the phone with them and I will never forget this.

This guy says to us, well, imagine if a nine-year-old boy was in the subway and he saw that and he asked his mother what that was. And we said, well, that is exactly what we are trying to do. Right. So it's okay for a nine-year-old boy to see breast augmentation ads and body slimming ads and so on, but not an ad about periods. 

And so we took that story to the media and the media was very pleased to report that story out. And we had immense organic traction. We basically went viral, so we had over 100 organic news outlets reports on us and within the space of 48 hours and this was globally.

And so that really sort of started the movement that was, I would say, sort of phase one, which, you know, the story and the narrative that started this movement around normalizing periods.

Closing Remarks

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And there you have it, the "Best of 2024" on Billion Dollar Moves! As we close this chapter, let’s take these lessons carefully into the new year. 

Remember, billion dollar moves start with bold decisions, a clear vision, and the courage to keep going when the odds are stacked against you.

Thank you for being part of our journey last year. If you loved this episode, again, don’t forget to subscribe, leave a review, and share it with someone who’s ready to lead, build, and invest better.

Until next time, this is Sarah Chen-Spellings and here’s to making #BillionDollarMoves in 2025.