Finding Opportunities in Underrepresented Markets with Billie Simmons, Daylight

June 7, 2023

Because of her open mind and willingness to say yes to most things, finding opportunities in the business world has never been too challenging for today’s guest, Billie Simmons! Billie is currently using her personal experiences in combination with community input to develop tools and programs that help LGBTQ+ people live their best lives.

In this episode, Billie talks about the potential that lies in underrepresented markets, the value in finding a balance between conviction and flexibility, and why it’s not actually a negative thing that we don’t have very much control over what happens in our lives!

About Billie Simmons

Billie Simmons is the co-founder and COO of Daylight, a company on a mission to help LGBTQ+ people live their best lives. Previously, she founded a startup to help trans and non-binary people access safe services. Her background is in marketing and software engineering (she taught herself to code when she was 10!) at fintech-focused companies such as Techstars and Anthemis Group.

Finding Opportunities Through Being Open-Minded

An open-minded entrepreneur actively seeks out diverse viewpoints, welcomes constructive criticism, and values continuous learning. As a result, finding opportunities becomes much easier! By being receptive to different opinions and approaches, you can discover innovative solutions, identify untapped opportunities, and adapt as needed. Open-mindedness allows entrepreneurs to explore uncharted territories, collaborate effectively, and seize unexpected chances for growth. It fosters creativity, resilience, and a willingness to challenge the status quo, paving the way for entrepreneurial breakthroughs and sustainable success.

Episode highlights:

  • When life presents you with opportunities, say yes! You don’t always need to follow a set plan. Billie’s approach has always been to follow her passions and do what she finds interesting, and it has taken her to incredible places. (01:59)
  • Lived experiences are the best blueprints for product development. It’s highly likely that whatever your pain points are, others have them too. So, to create something truly valuable, develop a product or service that meets your needs and improve it by listening to community feedback. (10:53)
  • “Any control you think you have over your life, you don’t.” This can be a scary thought, but if you shift your mindset, it can also be a liberating one. If you stop trying to exert control and instead embrace the fact that anything can happen, you’ll be able to find joy and success in so many unexpected places. (18:50)
  • Find a balance between conviction and flexibility. Whatever you are doing right now, commit to that 100%, but always be open to pivoting as you learn more about the needs of your target market. (22:05)
  • If your business doesn’t turn out the way you wanted it to, don’t see that as a failure. Regardless of the outcome, the lessons that you have learned along the journey will always be worthwhile. (26:35)
  • Sometimes the things you think you want aren’t actually the things that are going to make your life better. Don’t get caught up in external validation; what you think about yourself is far more important than what other people think of you. (33:35)

Billie’s best advice for entrepreneurs:

“Progress doesn’t seem linear, but it does stack. So even if you seem like you’re taking steps backwards, you still have all of the history that you’ve accumulated over time and the learnings and skills.” (28:16)

Connect with Billie:

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[00:00:50] A.J. Lawrence: I think it’ll be really fun. But as we were just chatting, I love your background because while you’re at school, you were interning, you were doing graphic and web design, you were doing all the sort of work of kind of getting your skillset together, as I call it, doing the reps.

[00:01:08] After you graduated, you were working at record label and doing social marketing, kind of doing all these different things. Then going on to an agency and then doing your own work before going to the Anthemis Group, where all of a sudden finance became something of great value before you then went on and kind continued developing your skills but then leaned more towards now developing Daylight. And I kind of would love just a little bit like, how was that? Did it just sort of stick like, oh, this is really more what I wanna do?

[00:01:43] I always love those things where you see someone and it makes so much sense in hindsight, but in reality our lives are pretty messy and they kind of just add up and then something clicks at some other point. So how was this journey towards co-founding Daylight for you?

[00:01:59] Billie Simmons: I was raised by parents who never had much of a plan for me. I feel like a lot of parents, they see their kid growing up and they’re like, one day you’re gonna be a doctor or you are gonna be a lawyer. And my mom in particular was always very adamant that I just do whatever was interesting to me.

[00:02:15] So really throughout my whole life, I’ve always just done whatever was the most interesting work that I wanted to do at the time. And that’s kind of as you’re kind of saying. From now, it looks like I had this great plan to get my reps in and do all these different kinds of works, but really I was just being open to different kinds of opportunities.

[00:02:33] And when I was offered things that seemed interesting or like they were going to expand a skillset or a worldview, I particularly loved doing things that I’ve never done before and getting to learn new skills and new things, I would say yes a lot. And that was really what defined my whole twenties was saying yes to basically anything that seemed cool or interesting or fun.

[00:02:55] And I’m a big proponent of that because I think that sometimes you can get distracted by the idea of a grand plan or a grand sort of goal that you’re heading towards. And at the time, particularly when I was a teenager, I wanted to be a musician. And I went to school for music.

[00:03:13] I always sort of joke that music was my first startup because you have to learn branding, you have to do accounting, you’re literally creating a product for people to consume. So there’s like product market fit, there’s team building, there’s all these different skills that you have to learn.

[00:03:29] And ironically, that was sort of what killed a lot of my passion for music over time was. Originally music was a sort of an artistic expression from my soul and from my emotions. And by the end it had turned into, what do my fans want to hear from me? Like what kind of music should I be making? Not from within, but what are the people that listen to my music, what do they want to hear?

[00:03:51] And yeah, I’d done all kinds of work. I’ve always been a very broadly creative person. I wanted to be a photographer for a while as well, I wanted to be a graphic designer. But I taught myself to code when I was 10, we started building websites after school in my after school club.

[00:04:06] And I always used to earn sort of pocket money as a child making websites for local businesses in my town. And so I had this skillset when I moved to New York to pursue music. That was really how I paid rent and how I made money. And I was still focused very much on becoming a musician.

[00:04:24] But Anthemis Group hired me to build a website for them and then later offered me a job to kind of do all sorts of different sort of technical marketing operations things with them. And I said, well, that seems interesting and I need health insurance and this seems like a cool company, so let’s do it.

[00:04:43] And it was a very eye-opening experience for me because it was the first time that I had fully committed to something full-time that wasn’t this grand plan that I had, and I really enjoyed it. And I got creative fulfillment out of the work and I could pay my bills with that work. And it was a real eye-opening moment just in terms of my own sort of personal perspective on work and on purpose and that kind of thing.

[00:05:09] And then it also really opened my eyes. I didn’t really know anything about startups. I didn’t really know anything about FinTech, and so this was really my first exposure to that entire world, and I loved it. I still love the energy, I love the optimism, I love that people in FinTech are genuinely trying to help people with technology and make their lives easier, make their access to money and capital fairer. And that’s kind of then been the driving force. And so I’ve kind of doubled down in that industry and that area for the rest of my career.

[00:05:40] But it’s been often through the same rubric, like what’s the next interesting thing? What seems fun? What seems cool?

[00:05:46] A.J. Lawrence: I noticed then having dive into development and then Techstars, I just really would like to know sort of a little bit about where Daylight came from. Where did that come from for you and your co-founders? And was that from your own experience? From the need? Let’s kind of just talk a little bit about that.

[00:06:05] Billie Simmons: Sure. So previous to Daylight, I had started a startup called affirm.space. And that was an app that I had built that was based off solving a problem that I myself have experienced as a transwoman trying to access safe spaces and safe service providers and affirming service providers, hence the name, in New York.

[00:06:24] And I’d gone to Flatiron School to level up my sort of software engineering skills, cause before that it was really pretty low level, building websites and JavaScript and that kinda stuff. Again, I was kind of I wanna become a real software engineer, which is ironic cause I don’t do any coding now. But what it did give me was the sort of empowerment and the ability to start building things for myself.

[00:06:45] As a musician, I sort of engaged with my identity to some degree but in my kind of "professional career", I hadn’t really. I’d sort of played down that part of my identity and wasn’t sort of forthcoming with the people I worked with and that kind of thing. It was really an opportunity to build something for myself.

[00:07:01] In promoting that product, I realized that there was a power to having built it for myself and that I needed to be forthcoming with my identity. That was a very uncomfortable experience for me but it was something that I knew was important and I knew that I had to do, and over time became much more comfortable with it.

[00:07:17] I did a lot of panels and I did a lot of speaking in order to kind of get the word out about this product that I’d built, and I met one of my future co-founders Rob on a panel at Google. He was working on an LGBT-specific app as well, and so we were both kind of in this space talking on a panel. I think it was a panel about mental health and technology, and I just remember being very, sort of impressed by him as a person.

[00:07:42] He and I have a lot of similarities in terms of the way we think about problems, our perspective on life, and we chatted a bit backstage and didn’t really think too much of it after that. And then about six months later, the pandemic had hit. I’d built an app that was about being in the real world and going to physical shops. And so that was not, not so great timing. And to be totally transparent, it was really hard trying to launch a startup by myself.

[00:08:09] I think that was the biggest takeaway that I had. I’m a verbal processor. I’m very much someone that needs at least one other person around me to kind of jam on ideas and to kind of hold me accountable, frankly. And so, things had kind of stalled with the app I was building.

[00:08:23] I was trying to figure out my next step, and Rob reached out to me and he asked me to do some user testing for this idea that he had been approached by an incubator to start. So there’s kind of a sort of a non-linear sort of beginning for Daylight, which is that a European tech incubator, Vacuumlabs had built this white label banking app, wanted to figure out if there was a community value prop for banking for specific social communities in the US.

[00:08:52] They had tapped Rob to kind of run it and to figure out what this thing is, and he had originally asked me to just do some user testing. I have lived in America at that point for four or five years and transitioned while I was there, so kind of have experienced banking not sort of outwardly as a transwoman and then sort of as a transwoman.

[00:09:09] And I basically talked his ear off for about three hours. And it was a light bulb moment for both of us. For me, it was a light bulb moment that there was a ton of experiences that I had normalized and hadn’t really considered were negative because of my identity. And for him it was, this woman really knows what she’s talking about. I should bring her in and figure out how we can work together.

[00:09:30] And so he asked me to join. And again, I guess the theme of this episode is the idea of this like grand plan versus what ends up actually happening.

[00:09:39] A.J. Lawrence: The journey.

[00:09:39] Billie Simmons: Yeah. But I remember at the time, I was interviewing for software engineering roles because I’d spent all this time training as a software engineer. I’d done a little bit of work as a software engineer and I’d been offered a job. And the job I was offered, alongside Rob, was originally to run community so not technical at all.

[00:09:57] And I remember my closest friend saying to me, you shouldn’t take this job. This is not the plan and you’re trying to be a software engineer. You need to get a job at a big tech company, you need to work your way up, and in 10 years time you’ll be able to do startups or whatever it is that you want to do. But no one was offering me a software engineering job.

[00:10:16] I didn’t have any money and someone was offering me work, and it seemed like interesting and cool work and so I said yes. Sometimes I wish there was like sort of more eloquent or meaningful reason but honestly, the fact of the matter was, I needed money and the project seemed cool and it did resonate with me. But yeah, it happened in a very sort of backwards way.

[00:10:35] And then as soon as I started, it was pretty clear that Rob and I were establishing a kind of co-founder relationship with one another. He started calling me almost every day to talk through bigger decisions that he was thinking through and we became each other’s confidant and friend and really built this thing together.

[00:10:52] Because we had the core banking features, but we’d not yet done the work of, okay, what is it that actually differentiates this product from any other banking product for the queer community? And so we ended up the main differentiator that we launched in 2020 was from my own lived experience, which is the absolute nightmare that is updating your legal name and getting that shown across all of your financial accounts.

[00:11:16] And so that was really where we started. And Rob is a gay man, and so both of us were using our own lived experiences to shape this product for our own community. And I think that’s really, that’s ultimately what we always return to. You can do a ton of user testing and we do do a lot of user testing.

[00:11:32] We’re always talking to our community. But in terms of where instinct comes from, where our core understanding of this product comes from, it’s from our own lived experience.

[00:11:41] A.J. Lawrence: Build for your own problem, but then learn from everyone else’s that come in. Because directionally, you’re always going to be the best customer. But the fine tuning, that’s where it gets really fun and interesting. Where it’s like, wait, you really want that?

[00:11:58] Billie Simmons: Yeah.

[00:12:00] A.J. Lawrence: Well, we’ll go down that direction. Maybe let’s talk a little bit about sort of like how Daylight helps families here? Just looking at it from a business point of view, you’re talking about dealing with bureaucracy and government over structure and then building their businesses based on your ability to fine-tune that. It seems like you’re marrying your customer knowledge, this deep base, within a relatively complex environmental environment to just increase the value that your users can get from this.

[00:12:34] You started with the ability to choose and display your name. Being able to utilize that and talk about this, how far deep do you see this going?

[00:12:45] Billie Simmons: We see it going very deep. So our mission is to help LGBT people live their best lives. That is actually the top level mission. And in terms of product solves for that, we’re pretty agnostic, right? So we have this banking product, we live in a capitalist society so to live one’s best life typically means accessing money in some kind of way.

[00:13:05] And so, the first version of this product was the ability to really be recognized by your financial institution as who you are. And the next thing we built in 2021 and 2022 was really around the idea of community and mutual aid, and really the idea that we’re stronger together.

[00:13:22] That is fundamentally what both a community and what a bank is, really. As we saw in the news, a bank doesn’t function as long as everyone that uses that bank is kind of all in and committed to the same idea. And a bank can’t run unless there is lots of people using that bank and putting all of their capital into that bank.

[00:13:39] And so, we launched community features. We launched cashback rewards for shopping at queer-owned businesses, and the next iteration that we launched, we’ve launched a few weeks ago now, is Daylight Grow, which is the idea of family planning services.

[00:13:53] And so this is really a double down on this mission because last year we sort of sat down I think the money product, we sort of have Daylight Money now and Daylight Grow as sort of two differentiated product. I think Daylight Money has done some really wonderful things in the industry and I think it’s a really powerful tool for those that are finding it useful.

[00:14:12] But there are plenty of LGBT people who want to use their own bank account. We wanna be able to help LGBT people who have a range of financial habits and so, what we’ve built now is a financial institution agnostic product that allows a member to go through the entire experience from choosing your method to literally delivering your baby.

[00:14:35] We support you every step of the way, both financially, logistically. We have financing options. We help you manage the costs, the budget. We’re launching a marketplace very soon that will be preferred providers, preferred rates and that kind of thing. And then we also have a concierge service that literally sort of guides you through this process – emotionally supports you, logistically supports you, helps you find legal resources, that kind of thing.

[00:14:59] And then again, at the end of the day it’s all community, right? I think we heard a lot in kind of customer discovery was, I’m speaking as the user here like I’m a gay man in my forties, I wanna have kids but none of my friends in New York wanna have kids.

[00:15:11] And so if I’m gonna go down this path, I’m gonna lose my support system and community to some degree because they don’t wanna be around kids. So how do I find a community of gay dads that are in a similar life stage and going through the same things that I am. And to me, that’s the really exciting part of using technology in this kind of context.

[00:15:33] Because where previously, communities might have existed in real life, you might have like put a poster in a coffee shop or something for a support group or something like that. Now, we have all this data so I can say, oh, I know three other gay dads in New York, maybe even in your borough and they all happen to have due dates that are the exact same as yours. So you’re all gonna have kids around the same time.

[00:15:56] I can put you in a Discord channel together. You can organize your own meetups. We might organize sort of generalist meetups for you. The power of using that data to connect people really is the thing that gets me very excited because no one’s really been able to kind of do that at scale before for this community.

[00:16:12] A.J. Lawrence: No. I moved to New York City in 94, I had grown up outside New York City but then I come back after university and grad school, and it used to be the joke that like, after the internet hit, you realized New York City had been the internet before the internet. It was the place you could find all the subniches or like there were the tons of niche, you know, self-published magazines with the ads that were specific to every subniche known to mankind in every type of direction.

[00:16:42] But now with the growth of the internet and then the ability to, as you said, to add data, that is just so cool because it’s like, wow, this was difficult enough to find everything. And again, this is a niche that is underserved and undervalued so finding that value and building it is really kind of a cool concept.

[00:17:00] You’ve gone this journey on your skills, you’ve gone on this journey, you had your own startup and kind of move now into this because you’ve built something really pretty cool. You’ve had this great background. Where do you see yourself on this entrepreneurial journey?

[00:17:15] Billie Simmons: I think if you’d asked me maybe even a year ago, I would have given you a very specific answer. And I’ve increasingly become of the opinion that when I genuinely didn’t know what I wanted to kind of do with my life, I attracted all of these wonderful opportunities and was able to say yes to them because I had no sort of rubric through which to say yes or no. It was just like, does as I said, does this seem cool and interesting? Let’s do it.

[00:17:42] And then for the first sort of two years of this journey with Daylight, for me it was all about exerting control over my life. And I think that was probably a direct reaction to where I was when I started Daylight, which was a place that felt very out of control.

[00:17:56] We were in the pandemic, there was all this ambiguity. My startup wasn’t working, didn’t have a lot of money. Like I was really freaking out to be totally honest. And so then I’ve had these 2 years of kind of really specific control being exerted over my life. Like I have my own apartment, everything is in its place.

[00:18:13] I have this very strict routine. I mean, you can go back. There’s like some very frankly ridiculous articles on the internet about my morning routine where it’s like 6:00 AM I get on my bike and I answer emails. But I was living like that. I really had this, and I had this, I had all of this plan.

[00:18:28] I had a partner. We were like, we’re gonna buy a house upstate and we’re having kids by this day, we’re gonna get married, and I’m gonna run this kind of business and do this, and do this and do this. And I’ve just realized recently that, that doesn’t serve me ultimately, and that I don’t get anything positive out of exerting control of my life.

[00:18:48] And it’s a fallacy, ultimately. It’s I don’t have control over my life. And again, to make it topical, this weekend was frankly a reminder of that. For 48 hours, I was like, I don’t know if I have a company to come back to on Monday. And I was hearing all sorts of things. I was hearing positivity.

[00:19:05] We banked 100% with SVB. So, maybe we’ll get help and maybe we’ll have our 250K FDIC insurance and that’s enough to meet payroll for a month, and then we shut down. That was a stark reminder that any control you think you have over your life, you don’t.

[00:19:21] And that might be scary to some people, but I think that you can make it a liberating experience. Because what it means is that, that anything can happen. And I think if you told me 5 years ago that this is where I would be in my life, running a startup that is so closely tied to my personal experience and even when days are really tough, I’m still doing the best and most exciting and fun work that I’ve ever done, it would truly be unfathomable to me 5 years ago that this is where I would’ve ended up.

[00:19:49] I wouldn’t even have dared to dream that I could have had my own company. And so through that, in 5 years time, whatever I’m doing in five years time is unfathomable to me now, as long as I don’t try and exert too much control over it.

[00:20:01] Who knows, like maybe I’ll be running a bakery upstate in a tiny village. Maybe I’ll be in politics, maybe I’ll be still running Daylight. Like who knows? And yeah, I think it’s really important as much as is possible for me now to kind of hold myself in that space, because it just means that you are more open to beautiful and exciting experiences to come your way.

[00:20:22] A.J. Lawrence: Yeah, I think this experience and just from having been on an entrepreneurial journey with lots of weird side journeys into microfinance and community development and all sort of other weird things, I can see Daylight moving forward, all these things because of the skill sets you are building and moving along. That is what I think is really cool.

[00:20:44] Also for many other people in the audience is that idea that when we go on these entrepreneurial journeys, it’s not a one-way road. Failure, there is external and internal failure. There is all these things, but the ability to develop our capability to handle or increasing our ability to utilize options and to have that.

[00:21:05] I think it’s really a fascinating thing. You’ve talked about just the way you’re dealing with the transitions of the business and those sort of transitionary phase as the business grows, and we can even just maybe even discuss like what happened and talk about more of a macro over the past week

[00:21:22] I know, like in my own experiences, that those types of macro experience hitting a business, really, a lot of the impact is going be how you are ready to handle it. It sounds like you were in a better because you were in the place to be flexible with what it would bring. How do you see yourself developing your skill to deal with sort of those transitions and the complexity of a business as you’ve moved along here and Daylight grow and it’s becoming a larger and larger entity. What’s helped you deal with that kind of increased complexity?

[00:22:00] Billie Simmons: Good question. You know I think, so to go back to a little bit of what you were just saying earlier, I actually have very strong opinions about optionality. I think people use optionality to mean to not committing to things.

[00:22:12] And I actually think that is the wrong thing to do. I think whatever you are doing in this moment, you should be committing 100% to this and only this. I’ve had countless of exciting offers, people have attempted to poach me. I’ve had founders be like, "hey, wanna build this cool thing with me?" throughout the last three years.

[00:22:29] But I am committed 100% to building Daylight right now. For as long as it makes sense for me to be the person doing that, that is what I’m doing. And I feel that way about every part of my life. Everything I do, I wanna do a 100% to it for as long as it makes sense if that is the case.

[00:22:43] And then, as you’re kind of finding out new things and kind of moving through life, you keep an open mind to that. I think conviction can be really good in a short term thinking way. We were very convicted on Daylight Money, and that is what we built for the past two years or for the first two years.

[00:22:59] And if we had remained really convicted on only Daylight Money, we wouldn’t have built Daylight Grow next. And so I think it’s about having that flexibility to know that you can both be sort of convicted and a 100% committed on something while also kind of keeping your options open.

[00:23:17] It kind of sounds like I’m sort of talking at sort of odds with one another, but there is a space that you can be in where you can kind of have your cake and eat it.

[00:23:24] A.J. Lawrence: There’s a tension in that.

[00:23:26] Billie Simmons: Yeah, there’s a tension. And I think really it boils down to the openness to be wrong, which is not to say necessarily we are wrong about Daylight Money. It’s still live, we’re still running it. But I don’t think we’ve ever been under the assumption that Daylight Money was the only thing that we’re gonna build for this community under the Daylight name, and I feel the same way about kind of my career at a sort of larger perspective too.

[00:23:46] There’s no wrong moves here. You’re always gonna learn something from anything that you do. And as long as you’re not blind to to being wrong, I think you can be open to kind of being flexible and handling that complexity.

[00:23:57] And then I think from a really tactical perspective, to be honest, I think my number one skill that helps me navigate through this is I’m really good at learning things and learning new things. And I’m very good at doing the fastest version of whatever it is that I’m doing. And so that allows me to juggle a lot of different tasks, that allows me to do the thing with a 100% commitment, but not spending a ton of time on it or a ton of energy on it still, which then allows me that kind of flexibility as we’re moving through.

[00:24:26] And that’s that’s good startup fundamentals, right? It’s like, what is the MVP of, I guess the rubric to use some real buzzwords here is like, what is the MVP of the task that you are doing? Does that get you through onto the next thing? And I think that is sort of instinctively how I just handle complexity and tasks and that kind of thing.

[00:24:46] A.J. Lawrence: I agree. I think a lot of times when I talk with people who are sort of hesitant on something, I usually push harder into the concept you believe will work if for no other reason than to break it.

[00:24:59] The hard work itself. I jokingly was talking about putting in the reps earlier in your career, but it’s the same thing in building something. It’s that idea that by building something or working in something to the focus of making it work, you actually will learn, if it will or not, better than if you just sort of do it.

[00:25:19] And then if you just sort of do it, you end up with the next, you know, not having developed for whatever that next situation may be. And in all likelihood, as you said, it will probably be Daylight.

[00:25:32] I very much can see, you make that work before. It’s hard and people miss that either one, doing everything they can to keep the options open.

[00:25:44] I had a coach who made me read, this was a great business coach, he always had me reading poetry, and it was around my 40th, there was some poem. It was all about the concept that men at 40 walk through doors that will not open again. The idea that as you move forward, there’s things. But once you cross through that door, you then once again, you have infinite choices at all time, but you direct that based upon the choices you make earlier.

[00:26:14] And I like the way you’ve put that thought process you’ve put into it, and I think that’s something a lot of entrepreneurs can [do]. It’s like when you’re hesitating, really look at it, and if it does fit, push into it because it will give you, I think, better opportunities in the long run, even if it doesn’t work. Though it’s a pain in the ass.

[00:26:34] Billie Simmons: Yeah. A phenomenon that I’ve noticed a couple of times when talking to people that have any kind of success is they become increasingly fearful of failure. Because as you sort of build up success, you build wealth around you, you built stability around you, you get further and further away from the version of yourself that wasn’t succeeding. And it’s terrifying to go back to that version of yourself or to conceive of going back to that version of yourself.

[00:27:00] To be clear, I’ve also experienced that fear, but what got you to that place in the first place was that lack of fear most likely. Because when you’re jumping into a brand new idea, it’s because, I mean certainly from my case, like I didn’t have anything to lose when starting Daylight. There was no real risk there for me.

[00:27:17] And as much as is like humanly possible, I try and remain in that space of, if I lose everything and I have to start from scratch, that is okay because I’m not actually the same person that started Daylight. I’ve had all of this experience, I’ve learned so much, I’ve grown so much. And who cares what the optics of that are externally if I have to go and, I don’t know, take an internship somewhere or an associate level position in some brand new industry or field because I want to learn about that.

[00:27:46] Just because I’ve been COO at a different company does that really, that only really matters to other people and to your ego. That doesn’t really matter to you and your sense of self and journey. And so, I think about that a lot actually, of startups and how we all have these sort of inflated titles and frankly inflated responsibilities.

[00:28:06] I was thinking about this over the weekend. I was like, God, if I have to go back and work a real job somewhere, what kind of job would I even have? Like, I don’t even know. I think it’s, I’m not really sure what my point is here, but it’s progress doesn’t seem linear, but it does stack.

[00:28:19] So no matter, even if you seem like you’re taking steps backwards, you still have all of the history that you’ve accumulated over time and all the learnings and skills.

[00:28:28] A.J. Lawrence: It’s brought to the picture. And I think you also added something on that is, the difficulty and then the work you were talking about doing, are they reviewing at least of it now?

[00:28:38] Realizing that this is not permanent – where we are, what we are, what we’re doing, all that. Because as someone who went through the dot-com, the little ones and then the big 1 in 98, 99, in my 20s, where it was like I had the inflated title.

[00:28:56] I was flying around the world first class, I was some senior biz dev role. And the reality was I was really just asking companies if they wanted fries with that. That was literally my skillset.

[00:29:08] I just happened to, you know, oh yeah, we need, we need this XYZ web. Okay. Do you want that with the basics or you know. I mean, literally my skillset was, do you want fries with that to help you? $2.5 million extra, thank you.

[00:29:21] And then after the dot-com, I did go. Then definitely after 9/11, there was that period where it was, well, why would I take a non-VP role? And you go through that and I think, that was part of my own journey and a couple of years of learning and growing and readjusting ego.

[00:29:41] Spending the time now, I think that is good that you’re evaluating because the industry can change, what we looked at last weekend, their economies can change, all different things. Technology, who knows what AI’s gonna bring us?

[00:29:54] The same thing that can take it away is also the same thing that makes it fun, because it could also give us new fun opportunities. So I like the way that you’re looking at building your capabilities as an entrepreneur but then also talking about the awareness that the title, the inflated value that sometimes we get from our success may not be the thing that really is the value.

[00:30:19] It is your capabilities you’ve developed and the skills that you’ve developed because you’ve done these things. Really are pretty cool. So how are you looking at what success is going to be for you?

[00:30:30] Billie Simmons: I think success for me is getting to exist in an environment where I have control- and I was just talking about not having control- but have control over my day ultimately. That’s really all I care about. That, and being able to do kind of interesting and intellectually stimulating things. I wanna work on interesting problems.

[00:30:51] I’m not super convicted either way on what those problems are. Like right now I’m very focused on this specific problem. Long-term, I don’t know. But realistically, I don’t think I could ever really imagine myself in a kind of traditional corporate job anymore, unless I did have a lot of freedom to kind of build what I wanted and to manage my time and energy how I wanted, which depending on the role might happen.

[00:31:15] But I think that’s really the only thing that success to me is not- as long as I can pay my bills and maybe one day buy a nice house in the woods somewhere. I don’t need like a big mansion or anything.

[00:31:28] I’m really not doing this to kind of build obscene wealth or kind of anything like that. It would certainly be nice to have some of those traditional hallmarks of success, to be able to retire my mother or pay off my brother’s student debt or things like that.

[00:31:42] But again, like right now I’m making more money than I ever have in my life, which is again, compared to other people, I’m probably not making that much money because I haven’t historically made that much money. But to me personally, I very much have all of my my cost.

[00:31:55] There’s not really anything that I can want for. And so I can’t really imagine if I made 4x the amount that I make now, I don’t think that would meaningfully change my life. I think it would change the different access I have to social circles or other things.

[00:32:10] I just, I’m not really convinced that’s important to me. Maybe at some point that might have been important to me, again, coming from like a place of scarcity or lack of control. But I think really the only thing I care about is how I feel on a day-to-day basis and what my day and my time kind of looks like, and having the ability to make free choices about that.

[00:32:32] Obviously I do 12 hour days very regularly at the business and my time is like often capitalized upon by meetings and things like that. But I’m doing that because I want to do that. And if I didn’t want to do that or if I didn’t think it was valuable to the business or something, then I would just walk away, or maybe not walk away, but slowly sunset my time.

[00:32:53] And so yeah, I think success to me is getting to wake up and getting to spend my day how I want and getting to do fun and cool things every single day. I don’t really need much else or need to have anything else really. I think the only add-on would maybe be one day not being dependent on a salary.

[00:33:12] I think that might give you sort of a feeling of true freedom. Because the place that I’m in right now, like I still have to work in order to pay my bills. I could maybe take a month or two off, but there’s no like, I couldn’t just take a year off or something and go travel the world right now.

[00:33:27] I think that would probably be the next sort of level of success. But beyond that, I can’t really think of any other hallmarks of success that I care significantly about. Obviously I’m very honored whenever we win any kind of award or I’m on any kind of list.

[00:33:41] Like those are nice, but those don’t really mean anything. You can usually pay to be on those lists. We don’t pay them as a rule and as a result, like you’ll see that we are not on certain lists sometimes. So when we are on list, it is meaningful cause it means I’ve not paid to be on there.

[00:33:55] But yeah, like I don’t, I don’t really. I think I can talk about this. I got interviewed for the Forbes 30 under 30 last year and I didn’t make the list. And it was my last year of eligibility. And I realized I had put quite a lot of stock in getting on that list and actually not getting it was the best thing that could have possibly happened to me in that situation because it made me realize that it had absolutely no bearing to my success, my sense of fulfillment.

[00:34:22] And I realized that the only thing I wanted it for was to send it to my family back home and to post about it on social media so that other people might take me more seriously. And that’s it. Like, it’s so meaningless.

[00:34:35] I think I’m in a really good place honestly. I feel very lucky to have ended up here.

[00:34:40] A.J. Lawrence: Very cool, Billie. How can people find out more about Daylight, about you, what you’re doing, and what you’re thinking about as you move forward?

[00:34:48] Billie Simmons: Joindaylight.com is always a good place for our kind of activities or our social media accounts. I believe our Instagram is joindaylightmoney. Most of our other accounts are just joindaylight. I’m terrible at tweeting, but I do have a Twitter. I believe it’s billie_simmons_.

[00:35:04] Honestly, the main output that I have is if I ever do podcasts. I will post those on my social media so that’s probably the best way to hear about what I’m thinking about. But I wish I was someone that was able to kind of devote more time to kind of output on things like that. I really respect and admire the people that are able, like yourself, to have like an output every week.

[00:35:25] Whether it’s like a newsletter or even like tweets. I have this rare psychological phenomenon where I go down to Twitter and I go to compose a tweet and I just have no thoughts. I have nothing to say and could never even think of anything to say.

[00:35:41] A.J. Lawrence: I love your background. I love how you’ve put together these things and approached the thing, so I would love to have back you forward and whatever happens happens.

[00:35:53] Thank you so much. We’ll make sure that we have joindaylight.com in the show notes, that we have Billie’s Twitter. We’ll have everything there, show notes, and our email when this episode comes out. I always say that and I realize that, I’m like, well, you won’t get the email, but still. And in our socials. So thank you so much for coming on, Billie.

[00:36:13] Billie Simmons: Thank you so much for having me.

[00:36:14] A.J. Lawrence: And everyone thank you so much for listening to today’s episode. I really, really appreciate it. This was a lot of fun. Please, if you like the conversation we had with Billie, go to beyond8figures.com and sign up for our newsletter. You’ll be the first to know when we have other really cool entrepreneurs like Billie come on the show.

[00:36:31] All right, everyone, I’ll talk with you soon.

[00:36:39] This episode of Beyond 8 Figures is over, but your journey as an entrepreneur continues. So if we can help you with anything, please just let us know. And if you liked this episode, please share it with someone who might learn from it. Until next time, keep growing and find the joy in your journey. This is A.J., and I’ll be talking to you soon. Bye-bye.

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