Founder's Story - She Was Told to Give Up—Now She Funds the Startups That Change the World | Ep 255 with Erika Aquino

Episode Date: August 7, 2025

Erika Aquino opens up about her journey from a psychiatric hospital to becoming one of the most respected investors in emerging markets. Diagnosed with bipolar one disorder, cyberbullied, and a survivor of abuse, Erika refused to stay down. Instead, she built a life—and a portfolio—rooted in empathy, wisdom, and comeback power. She now writes the checks that change lives and rewrites the rules of what success looks like. Key Discussion Points: Her battle with mental health, stigma, and public shame The role creativity played in rebuilding her confidence Why she looks for pain-driven founders, not pitch-driven ones The brutal questions she asks before writing a big check How gender bias shows up in boardrooms—and how she navigates it What most founders get wrong when approaching investors Why failed founders often make the best bets Her global thesis: funding the people who rarely get funded Takeaways: Resilience isn’t a buzzword—it’s Erika’s investment criteria Emotional intelligence is as important as financials Great investors don’t just back winners—they help build them Real change happens when capital meets compassion Closing Thoughts:Erika Aquino is more than an investor—she’s living proof that our lowest moments don’t define us. They refine us. This episode will challenge how you think about leadership, failure, and the true meaning of success. Get more leads and grow your business. Go to https://www.pipedrive.com/founders and get started with a 30 day free trial. Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising.

Today's episode is sponsored by Pipe Drive, the number one CRM tool for small to medium businesses. I am excited to share more about them later in the episode. So, Erica, I know we were just talking before we started, and you have this incredible story, and I know that the audience is going to be super inspired, and we're going to talk all things around investing, what you look for, but we're going to start heavy today. Sure. And you have this journey, you have this journey, you wrote this book, you had moments in your life where you were going to give up and you did it.

How did that work for you? Okay, so roughly about eight years ago, I was diagnosed with bipolar 1 disorder. It was a whole thing. You know, I started my entrepreneurial journey really not knowing. what I was in for. And I found myself in over my head seriously. And I've made some mistakes. I've made critical mistakes and not knowing as well what I was facing internally, because I didn't know I had it. I ended up being a victim of cyberbullying. That's not without my own fault also. I did have a hand in instigating it in a way. and I ended up in a psychiatric hospital where I was diagnosed with bipolar one disorder.

Of course, I got checked out. I went to therapy, but, you know, there was also a journey of that, of coming back from that. And that was extremely difficult. I'm not going to lie. My self-esteem was shot. I didn't know if I could do it. In fact, I fell into one relationship a few years ago where I actually became a victim of, I'll say it out here, abuse. And it was tough. Again, I didn't know if I could do it,

but then I had a wonderful support system. I went to therapy. I dealt with those issues. And I came back from it stronger and stronger than ever. And I wish people would know that whatever low you're feeling, it's not the end. There is some way out of it. How I dealt with it, I kept creating. I kept at it. I knew what my strengths were. In fact, I think, you know, the word game boggle, where you shake the, yeah. I was very good at Boggle, and I'm still very good at Boggle.

And I would beat other people with Boggle. And I'm like, if I am good at Boggle, I'm good at other things. So I kept creating. I kept, I consulted with different entrepreneurs. I helped out in a foundation that gave educational access to underprivileged children. I headed that foundation, actually, with a few programs. And I kind of evolved from there. I realized, okay, I have my talents.

I have my gifts. Let's focus on that and keep going. And, you know, maybe atone for things I've done wrong and maybe climb up from whatever struggles that I've had in the past. So, yeah, here I am now with that. Well, thank you for sharing and being so vulnerable. Of course, yeah. I've also had moments in my life that, you know, might run parallel or similar things, like you said.

And sometimes I've always struggled with as I start to slip back into something, it's like creating habits in that moment so I don't go backwards. Besides being creative, is there something that you do in those moments where obviously business is stressful, investing is stressful? and I think stress sometimes can cause, you know, these feelings and these emotions that are very negative. How do you get yourself out of that feeling when you see it starting? You know, it's so easy to kind of wallow in your emotions. It's very easy. And, you know, once you start doing that, it's a spiral. It's a downward spiral.

So I talk. I reach out to my therapist. I reach out to friends. I play with my niece and nephews. I make sure that I'm not alone in these moments. It's hard, of course, but, you know, if you share your struggles, other people, people who care about you would gladly, gladly step in and really just help you out, you know?

I think we're seeing a lot of stigmas around, you know, mental health and feelings and just going to therapy and getting help. I think we're seeing a lot of these stigmas. the walls are breaking down at least in the u.s it's been that way for a while i know in the philippines i spend quite a large amount of time every year there i think there's there still is at least from what i've heard um there still are some stigmas around mental health and therapy although it seems like it's getting better but how do you feel around this space because i think founders you know it can be a lonely place right it can be it's a place where we probably need help but it's not

is it so easy, thinking about how people will judge us if we do, say, get therapy or talk about it, let's say on social media. Right. Absolutely. So my thing there is, you know, to name it, is to tame it, essentially. So if you know what you're dealing with, it's easier to kind of tackle it from there. With the Philippines, yes, there is a stigma in the U.S. as well. But, like I said, find your people.

It's not hard once you start talking about it. And people will stand up for you. And there are resources back home in the Philippines or here in the U.S. that you can turn to for free. In fact, one of the ventures that I've dabbled in is a mental health startup that allows employees of companies to avail of these mental health services. And companies can easily make it afford.

and even free for their own people to access good mental health facility. So, yeah, it's really just about talking about it. Keep talking about it. Never mind the stigma. Who cares what they say. Focus on yourself, right? One of the biggest game changers I've seen for founders isn't another pitch deck, another tool, or even another investor.

It's how you manage sales. And I'll be real, when we first started, we were getting leads. We were getting business, but the pipeline was so messy. Leads were falling through the cracks. We weren't following up. We were losing tons of revenue and money and everything was all over the place. It was chaos. That's when we started using Pipe Drive, today's sponsor and the number one CRM for small and medium businesses. But the thing I love most, Pipe Drive AI, it actually helps you work smarter, not harder. It gives you real-time deal recommendations, writes your emails with one-click prompts, and even summarizes entire email threads in seconds. For us that met no more guessing who to follow up with or what we said last week. We focused on closing great clients and more deals. If you're a founder or creator trying to scale your sales, you need this. Over 100,000 companies are already using it and you can try it right now. Go to pipe drive.com slash founders for a 30 day free trial. No credit card, no commitment. Just head to pipe drive.com slash founders

and see why I trust it every day to grow my business. That's what I always say. like that. And I like the fact that you're investing and you're a part of these companies that are making impact and things that obviously are impactful for you. So when you're investing across borders, because you have companies that you've invested or your own ownership in or equity in all different parts of the world, is there a one, is there a universal trait that every founder has no matter if it's in Asia, if it's in North America, if it's in Europe? Is there one thing that you're seeing like, wow, this founder has it, or the most successful founders I've invested in, no matter where they are, they have this one trait.

Absolutely. Yes, there is that common trait, and that is, you know, the best ideas, first of all, come from people really close to their pain points. It's not necessarily the loudest voices in the room, but these are people who have lived and breathed their pain points. For instance, I've invested in a founder whose son lives with autism. And he created an app that tackles nonverbal children with autism that helps them out and gives them resources as well as their families. And his pitch, he closed his pitch with saying, at the end of the day, I'm just a dad who wants his son to tell him that he loves him.

And for me, that was impactful. And I could see his path to profitability, but I could also see his passion. They're obsessed with a problem and not just the pitch. they're easily coachable, but they're not easily shaken because they know at the end of the day that they are solving a problem that exists, that they want to help solve. Was there ever a founder that you backed that other people were like, I don't think this makes any sense. I don't believe in this. And it really paid off for you. Yes. There have been several. But again, that one founder stands out where I think I wrote the first big check for him. where he said that, you know, I literally approached them and said,

I like you, can you please pitch to me? And he did. I saw his fundamentals. I saw his pitch. I saw how passionate he was about the subject and where he was going. And honestly, right now, he has revenue. He has downloads and I believe not just the Philippines, but in Canada, in Saudi Arabia, in the, in, at,

UAE, the United States. He has downloads in several countries, thousands of downloads. So, yeah, I think it's paying off. I mean, that's amazing. So before you, is there something that you think about? Before you write this big check to someone, you've heard the pitch, you're sold on it. Is there something that you go over or something that you think to yourself before you actually write that check and give it to them? I actually slap founders with questions that they haven't necessarily heard before or things that are things that are.

that they're not used to. One question I ask is, what are you going to do if you're going to fail? And that kind of rocks them. I kind of, I see how they, there's no right answer to this, by the way. It's just I want to see how they're dealing with the mental stress of being a founder and whether I can help them in one way or another. I ask, what would it take for you to ditch this complete, ditch your day job? and, you know, just embrace this hustle or this new startup completely.

What would it take for you to make this your entire life? I evaluate the qualitative and the personal questions, aside from the data room. I have my CFO who lives and reads the data room and she's awesome. And their answers with that together with the answers that I asked, the questions that I ask, they're kind of, I see how chemistry, founder of funder chemistry, and I see how the resiliency of the founder as well when they tackle their own struggles or their own challenges when building a business. I like that.

Founder, funder relationship and then resiliency. Yeah, I mean, business is all about failures, right? Like one failure turns into your next success. So what do you think that founders are. doing wrong when they approach an investor? And then what are a few things that they should be doing right? Okay. When approaching an investor, you know, I've had cold, cold emails, etc. Honestly, cold emails are fine. But you have to acknowledge and do your research, I believe, for who your funder is. I've had one pitch where it was a cold email. They approached me and they actually asked

So what do you do anyway? Are you a supplier? Are you an investor? I'm like, in my head, I'm like, I'm easily Googable. You can, you can Google me. That takes two minutes. That for me, if you don't know who is at the table, please make sure that you do or else you just don't belong there. Another mistake that I see is just lack of knowing their numbers and knowing what their business is. I ask, I tend to ask, what. what external factors there are that could make their business a success. And they tend to get confused by that, by that question. You know, what current events or what things that are happening outside your own business that will make your own business a success? And if they answer that, that means they know the landscape out there. And they're not, they don't just have tunnel vision.

It is wild how you have Chatsybt and LLMs. It could do all the research for you, yet people are still not prepared. I always crack up when I get those emails or messages. It says like, hey, company, right? Like, it's totally not specific to the person. Definitely, that's like a delete. So I started thinking about something that happened a couple years ago or many years ago. My wife, who's also from the Philippines, somebody reached out to her because they wanted to invest or they wanted to acquire one of her companies.

And they said, do you need to talk it over with your husband? but as in but they were saying it as in like you're not really the one who made the business your husband did even though I had nothing to do with it and I always I always thought of that like wow that kind of inspired me to do this show to do thing just because it's you know there are stigmas out there and it's quite sad in the business world I see this we go to events and people will ask me oh what do you do thinking she's like just the wife even though she's a business owner at this event And I'm just a TED. It totally happens to me whether it's, with my boyfriend, my partner, he's amazing.

But, you know, they tend to ask him first. He doesn't notice it, but I do. And I think it just happens so often that sometimes even I forget. And that's kind of sad. But also the reality is it's also a filter, a good filter for me to gauge how people think in a way. Am I just this person, this, this Filipino that is with somebody else who may have boosted her up, maybe, but, you know, it's not.

That's not the truth. So it's a really good filter for me, socially, business-wise, et cetera. So how do you navigate that when you're, I imagine if you walk in a room with maybe other investors, do the founders talk to you? Maybe you're the main investor. I've heard of these issues where they won't talk to the woman, but they'll talk to the men, even though the woman's like the main investor or the one that's controlling the money. How do you navigate these scenarios? Well, actually, my partner's great at saying, oh, she's the one. You go talk to her. She's the one with the money. Same thing with me. I also, it's not about really asserting myself,

but I quietly watch, honestly. How will they navigate this space? How do they navigate themselves socially? That's also something I watch out as an investor. Again, funder, founder chemistry. How do they view a woman investor in general if they're not a woman? I see a lot of nuances, and what I like to do is really watch those nuances at play socially. I mean, I travel a lot, so sometimes it's a culture thing, sometimes it's a personality thing, and I tried to discern what this was.

Yeah, thank you for sharing that. I really like this funder, founder chemistry. I think that that's very fascinating. And I haven't heard people talk much about that. Talking, you know, going through your journey of what you just, what we were just talking through, has this inspired you to be able to fund more maybe female led, organizations, because I know women, from what I've read, they get a couple percentages of one is being invested in women-owned or led organizations. Is this inspiring you of how you look for companies to invest in? Oh, absolutely. I don't just invest, honestly. I try to advise. I connect them with the right people. I try to amplify what they're talking about or what they believe in. And I think it's really about giving the microphone, giving that amplification to those who may need it the most.

Investment isn't just about, or angel investment isn't just about the profit or the bitch. It's about creating an impact. And for me, creating that impact is giving that piece, backing founders who are not just diverse, but are reflective of the world as it is and how it will be. And that for me is really quite important.

Wow, that's very special. And it excites me because there's so many problems we can solve. Absolutely. And you talked about it earlier, you solved the problems that you many times have experience in. So there's so many problems that will never get solved if these people are not being invested in. And these people are not given a chance. So if you think back to the many founders that you've come in contact with, that you've had experiences with, and you look at the ones that were absolutely the most successful out of those bunch.

Was there one or two things that they did along their journey that other people can learn from? Oh, they failed. They absolutely failed and got right back up the horse. They have experience in either closing a company, selling a company, starting a company. they have corporate experience, they have the network, they've failed miserably certain times in their life, but they got back right up there. It's really about coming into things with that wisdom of what it takes to be an entrepreneur. I was thinking about this a few days ago around you're mentioning the failure piece. And I've always wondered, how do investors see this? So if you

invest money in me and I fail. And then I come back to you and say, Erica, I failed. You watch. This is the reason. But I've learned this and this is my new idea. I would like for you to invest in my new idea. I always wondered, how does that play out knowing that the money that you first invested is now gone? And now they're coming back again. Is that a like how does that all play? I've never, I've always wondered. It's about how they got back up. First of all, what was the issue in failing in the first place. It could have been something external to the founder, something internal to the founder. I've had one where the founder was going through a very rough divorce. And that, of course, affected her mentally. But at the same time, she was able

to pivot in a way. Yes, she closed that first business. But on that, business, she kind of built up something else that was similar to it, but she had the knowledge about it. And, you know, I think I always love a good comeback story. So again, it really depends on what the issue was, how they're rising up, et cetera. And of course, I mean, again, I love a comeback thing. It's my thing. So I would really like to see a founder come back from wherever it is that they failed. Thank you for sharing that, Erica. I also love a comeback story. I mean, that's like Rocky. Like, yeah, of course. I mean, so many movies is like, we love to hear the comeback story. I know you just written a chapter and a book, Unreserved, rewriting the

rules of business. And I know it's also written by Ashley Deland and people can find out on Amazon. Yes, absolutely. What can they expect when they read this? So this is, a book of 24 women who wrote their own chapters of resiliency in a way. These are comeback stories. These are women who've suffered deaths, abuse, all these things that, some unimaginable things. And it's a story of how they rose up and got to work and started their own businesses, investments, etc. I'm actually the last chapter there. close out the book. So, yeah, you'll read, yeah, the finale. You'll read more of my story on that, in that chapter, yes. Amazing, Erica, unreserved, rewriting the rules of business. I can't wait

to read the book on Amazon, but this is, I'm super inspired today. You gave so many nuggets and takeaways. This has been amazing. And I'm just, yeah, I'm so inspired by the fact that you're just global, that you're in all these different places. You know, you're not focused on one market. You're focused on many markets. And I can imagine how that just also helps the portfolio as a whole. And I can't wait. Absolutely. I know you have so many things you can't talk about that are coming down the pipeline.

So you've got to come back. Yes, yes. Come back. Absolutely. Let's talk about it again. But Erica, thank you for joining us on Founder's Story. Thank you very much for having me. Yeah.

I love my time here. Thank you, Daniel. One of the biggest game changes I've seen for founders isn't, another pitch deck, another tool, or even another investor. It's how you manage sales. And I'll be real, when we first started, we were getting leads, we were getting business, but the pipeline was so messy. Leads were falling through the cracks. We weren't following up. We were losing tons of revenue and money and everything was all over the place. It was chaos. That's when we started using pipe drive, today's sponsor, and the number one CRM for small and medium businesses. But the thing I

love most pipe drive AI. It actually helps you work smarter, not harder. It gives you real-time deal recommendations, writes your emails with one-click prompts, and even summarizes entire email threads in seconds. For us, that met no more guessing who to follow up with or what we said last week. We focused on closing great clients and more deals. If you're a founder or creator trying to scale your sales, you need this. Over 100,000 companies are already using it and you can try it right now. Go to pipedrive.com slash founders for a 30-day free trial. No credit card, no commitment. Just head to pipe drive.com slash founders and see why I trust it every day to grow my business.