I. What inspired you to become a founder?

Maggie S: Tell us about your founder's journey. Why did you want to become a founder? What was the inspiration behind your startup?

Lisa Skeet: I would say, like most entrepreneurs, I found LandIt trying to solve my own personal pain point, which was a career inflection point.

So chemical engineer by training, that means my teenage boys think I know something about math and science and started off in engineering and product development at Procter and Gamble. Got recruited way to join a startup. That's where I caught the bug. I'm like, This is great. How do I do this for more people?

Richie Serna: Yeah. I think I had a pretty nontraditional path to starting a company. I actually started my career in management consulting out in New York.

Anvi Patel: So the journey to entrepreneurship for me has been sort of a winding one. I grew up as the child of small business owners, so I've always had that influence around me. But it took me quite some time to find my way to it. I started my career very, I would say traditionally at Procter and Gamble at large companies had an incredible experience running and building big brands, big consumer brands everywhere at Starbucks and Adidas.

But my mind started to go towards the calculus of what am I spending my days on. And the pain and friction that parents kind of face every single day. And I started to have these questions about why were things feeling so broken as a new parent? And it would take until having our second daughter a couple of years later for me to actually kind of jump into my first main startup, Poppy, which was focused on solving childcare for families.

Julia Cheek: So I started off really well, like many founders, based on my own personal experience that I had with the health care system and just knowing that I was super passionate about solving a problem.

In my late twenties, I had a really bad experience with an odyssey of doctors to diagnose some basic hormone and vitamin deficiencies, really focused on the fact that I had to pay thousands of dollars out of pocket or towards my deductible for a bunch of different lab tests, none of which I got the results for or I had any useful data from, or even frankly, was able to get a real interpretation from any one of my doctors. And so it was that experience that really prompted me to realize that this was a huge problem, that every person who needs a medical diagnosis goes through. And there had to be a better way to bring technology to the process and make it better for the actual patient and really the consumer of health care, which is you and me.

Sheila Lirio Marcelo: So there's really two companies right now that is near and dear to me. One, I founded a company about six years ago called Care.com. And so that combination of what we call in the care industry being sandwiched between child care and senior care was really the inspiration that started a company called Care.com that I founded again 16 years ago and then took it public in 2014 and ran that for about seven and a half years. And so, that combination of what we call in the care industry being sandwiched between child care and senior care was really the inspiration that started a company called Care.com that I founded again 16 years ago and then took it public in 2014 and ran that for about seven and a half years. And then, the second Founder's Journey story, and you'll notice this about me and social impact, is that we then sold Care.com February 2020 to IAC.

Now fast forward, I'm a private equity venture partner at NEA Private Equity Firm, and I was doing diligence on a company called YGG and I watched this documentary. And in this documentary was a grandmother who had downloaded a crypto wallet, purchased cryptocurrency, and was making more than the average rural wage and a local province in the Philippines in this new technology. And so what really inspired me was how do we create impact and help people like this grandmother, Lola, Virgie. So started a new organization in EdTech called Proof of Learning Where We Want to be the leading edtech platform in the Metaverse. And our very first project is training Web two to Web3 developers.

II. Raising Capital as an Underestimated Entrepreneur

Maggie Sanchez: And we know that raising money is the Holy Grail to get any business off the ground. So tell us about your experience raising money from early stage to follow on capital. What was the hardest part and do you think there were any anything was unique about being a female founder?

Richie Serna: I think there's really three things that are really key to it. First one is having grit. The second one is really practicing your pitch and really honing it. And the third one is really running a process. And so I like to think about fundraising as both an art and a science. And so when it comes to creating a great pitch, the first part of it is just realizing at the very beginning that you are going to suck and that you're going to be very bad at the first few pitches that you do. And so that's where grit really comes in. I think I probably got rejected maybe 75, 85 times before I got my first. Yes. And it's okay to suck at this, right? There's not you don't go to school for fundraising or pitching. And I think that's a very key characteristic that any founder has to have, is realizing that almost every single job that you're going to have the company. And as a founder, you will pretty much have every single job at the company. You won't be great at it, and that's okay.

The second part that I would say is really practicing and by yourself practicing with others, practicing with your VC friends, practicing with your family, just really trying to hone that story because a big part of it really is nailing the narrative. It's about the storytelling aspect. Relatedly, to the specific issues that they're funding matters a lot, whether that's early stages, because again, it's a hope and prayer deck and a team. And so that attachment to the intuition of why they would invest and how they can relate to it matters. But I found relatability also matters even by taking a company public, because I remember pitching the concept of care.com and a bunch of analysts, mostly majority men, were behind their computers and they just wanted to plug in the number into their computer. And many did not have kids yet. Many did not have pets to take care of because they were juggling banking know investment banking job. Many did not have aging parents yet and so for care even the relatability later as a public company also mattered.

Sheila Lirio Marcelo: I remember when our CFO was new, Michael Berg joined us on the team. He started joining joining me on the investment meetings. We would do these roadshows. I said to him, it's going to be different if there's a woman in the room, if it's a group session that we're trying to educate them on care.com. And when you see that, the conversation will change. And in fact, it did happen and he was very surprised by it. We got a question from a male investor who typically always starts with, "why would I need care? You know, I hire a nanny and why would I need care.com after that?" And, when there's a woman in the room, she will say, I don't know about you, but you don't understand that hiring caregiving is difficult and the turnover is high and there's always different needs in the household. And, I've used Care.com eight times, so I don't know that your question is relevant. So you add one woman in the room and the conversation changes.

Julia Cheek: I speak about raising money often. I am a solo female founder, first time founder, nontechnical, and I was raising money for an idea that I had no industry experience in, and I was based in Texas. I had a lot working against me. Perhaps, what I had working for me is, frankly, I'm white, which is, as we know, a significant benefit, unfortunately, as well an HBS grad. Those were the only two factors that I think had any kind of a pattern recognition for investors. And I had so many no's. There were, frankly, male founders around me raising term sheets pre product market fit at three or four times the valuation. I had people tell me it was a terrible idea and it would never work.

In fact, the way that I used to get meetings is that the staff at VC firms who are typically female, the admin staff, the recruiting staff or the spouses of partners would say, hey, we're using this incredible company, you should talk to them. That's not unusual in the sense that it's not uncommon for investors to want to invest in things that they know and understand the problem. But that means because there were and are so few female venture investors, there's inherently an information asymmetry about the problem.

Lisa Skeet: Yes. So I would say fundraising is probably only second to having a simultaneous root canal on every single one of the teeths in your mouth. But I would say it's challenging for most people, but it's really challenging when it comes to either being a woman or a person of color. That's why only less than 1% are actually able to secure financing, But that means if you're not in the room, then it's even more challenging.

I was fortunate in the end to have had allies and others that invested, but the process to get there was quite challenging and that's when I realized the importance of product market founder fit, not just product market fit, but also your proxies for success. And so as a first time founder, even I had worked for quite some time, I had to surround myself with people to derisk what this looked like.

Anvi Patel: We talk about this or it's talked about often, but in VCs it's all it's the game of big numbers, in fact, because a lot of investments are going to go to zero. Some will maybe return just the capital or maybe one or two X, but the ones that they're really going for are the ten x plus. That's the vein in which a founder needs to pitch or sell the VC on how is this the best place to put that $1 that is disproportionately going to get you that ten out?

III. Advice to underestimated entrepreneurs

Maggie Sanchez: Based on your success, what is your advice to female founders, the founders of color as they think about raising money. What can help them succeed quicker?

Lisa Skeet: It comes down to access and acceleration. How do you accelerate an entrepreneur's time to goal. I have the vision, I know where I'm going, but what are the things that you need to know so that you can have those proof points? It's almost as if you are giving people a playbook.

Sheila Lirio Marcelo: The second is a sense of authentic boldness, is the key piece of advice I always give, which is there's always this feels like diametric opposites between those two words. How can you be authentic and vulnerable and yet be bold? And I often say authenticity drives, and that vulnerability, in fact shows your strength and confidence that you're open. And investors actually really like that, that this person is going to be transparent, we're going to give them their give them our money, and they're going to be responsible around it and and can talk to us and get their our advice.

And the boldness is the willing willingness to take risk. And somehow that sense of vulnerability is an inner confidence to go take risk and try different things so that you can learn.

Julia Cheek: You have to have a thick skin. You also have to take feedback and understand when the feedback is real and when it's really something to ignore. And so that can be a really hard process because mentally you have to be ready for a lot of rejection, and yet you have to be able to still come back to the table and say, okay, I'm going to take this under advice, under advisement, I'm going to change my story. I'm going to work on these things before I go back out to raise.

I think having some advisors who are neutral to the process and can really help you understand what you need to focus on and what you can ignore is really important. And then the last thing I would say is you have to start early, especially as an underrepresented founder, a female person of color, etc., nontraditional background. I think that you have to start even 1 to 2 years before. Now, that can be really hard if you've just now started your company. But for example, our first institutional money from a fund came from someone I had pitched to 18 months before, and I started to build a lot of those relationships. It was a no before, but once we started to build traction, it became something where they were kind of knocking on my door to invest.

Take a no seriously, but unpack it, understand the nature of it, and really start to build those relationships as early as you can in the process, especially if you're a first time founder.

IV. Aha Moment

Maggie Sanchez: What has been your biggest aha moment?

Sheila Lirio Marcelo: That the journey of building and creating at the core of it is really in service of others. And that's a hard one because as an entrepreneur, every day you have to get up and motivate yourself. And there's just a lot of voices in your head that you have to deal through. And I just come down to that. The confidence and the ability to conquer difficulty is to sometimes have an out-of-body experience. Who says, it's less about me and it's about the people I'm serving. The purpose in my heart for my team, how we're going to make a difference. It's life short. And so I think that that message, if you're clear in your head, can get you through many things. And it powers the resilience to get through it and to just build, build for others is really what I want to share.

Julia Cheek: I think it probably goes back to finding that very, very, very initial product market fit. Before we raised our series A, we'd raise a little bit of money and I remember I had like four employees and we couldn't actually get customers to buy the product. Now, to be fair, we'd only been at it about six weeks, but in my mind that was enough. And we were going to throw in the towel and one of our first employees said, Give me two more months. And I remember I had we use Stripe as our as our payments processing, and I had every single transaction set to ding my phone. And I remember it's like like clockwork. There were a couple of weeks where it started digging a little more frequently.

I just remember all of a sudden the dings started coming multiple an hour and then multiple a minute and then it just stayed. That is sort of to me is a really clear representation of what it looks like and feels like when you finally get product market fit.

Richie Serna: I think the biggest aha aha moment is that there's really no secret sauce or secret recipe that's out there that somebody has that you're not capable of achieving something. Right. When you think about startups and you read about these individuals in TechCrunch, you think that maybe they're smarter, they're, you know, harder working or they have some secret genius idea that you just don't have. That's not real. I've met all these people, you know, and when you sort of, you know, get into the room, right. And you kind of look around, you're like, you're just as capable, if not more capable than these individuals, because you had to work twice as hard to get there. And I think, you know, being a part of these, you know, incredible portfolios, being backed by some of the best venture capitalists, that aha moment is very liberating and inspiring to just now, like you can do it.

There's often a sense of sort of imposter syndrome, but you are more than capable. It's about getting out there and putting in the hours. It's about putting yourself in positions that make you uncomfortable and just knowing that you just have to keep going. That's like the secret part of a lot of this stuff is that most of these folks who made it just didn't quit.

V. Leadership

Maggie Sanchez: Now I'm going to shift to building a team. We know that it's critical, right? The team and the leadership is so important. So when you experience building the team

Julia Cheek: Building and managing a team is the hardest part of, I think, any founder — or, frankly, any leader's job in any company.

I think the team is both what makes and breaks the company. There's a lot when you are part of a really fast-growing startup, there's a lot of learning and there's a lot of experience compressed into a very short amount of time. And so it's really about who can scale with the company, who, you know, you could work at a startup for 18 months and it's like seven years at another company.

And a lot of it goes back to making sure that I as CEO and reflecting on who am I as a leader, where my gaps, where do I need to fill in from other types of leaders that I can hire. And what's the very best talent that I can get on the team?

Richie Serna: I think one of the key things I've learned over the last few years is really that the team and the entire company for that fact really follows your energy. Both positivity and negativity are really incredibly contagious. And so when you're happy and you're up and you're energized, the team feels it. They feed on that, inspires them to work harder, faster. It makes a much more energetic and collaborative environment. But on the flip side, if you're stressed, if you're not taking care of yourself, if you're terse with people, that will also trickle through the entire organization. So a key part of really managing the team is managing those dynamics, is understanding that you're always being watched and that whether it's your negativity or somebody else's negativity that you have on the team, it can be very toxic and you have to cut it out like a cancer to make sure that you can have a really healthy team dynamic.

And I think the last part is that any healthy team, any successful team is. Going to have to rely on a really strong degree of trust. And when it comes to starting a company, there's a lot of things that are going go wrong. There's going to be a lot of high pressure situations. And the only way to get through and persevere in those moments is based on the relationships that you have with each of your team members.

Anvi Patel: It's probably one of the most critical things and it's probably the trickiest things.

What increases the probability of success for this idea this company to actually make is and having multiple people that share a vision that can carry this little spark and let it continue to turn into a flame, turn into the blaze, that's really critical.

Sheila Lirio Marcelo: One of the key things on the journey of building teams in my life is really focus on long term relationships. I think when you start to attract people, they want to know that you are there for them throughout their careers rather than the transactional, specific thing that needs to happen for the company.

I think it's it's being true to the humanity of respect and really seeing people that makes a difference in building teams.