BONUS: Mid-Life Crisis or Trough of Sorrows?

Straight to you from Denver, Colorado, this is Precursa: The Startup Journey. We share the ins and outs of building a tech startup from inception to launch to revenue and beyond. If you’ve ever wondered what building a startup from scratch really looks like, you’re in the right place. With full transparency and honesty, we reveal it all about Precursa on our ride from idea to exit: the wins, the lessons learned, and the unexpected twists and turns. Hello, friends and fellow entrepreneurs. Welcome back. This is Precursa: The Startup Journey. So as I mentioned before we took the break, we are coming back full force with the next series of episodes. We are introducing two new segments, one that’s called entrepreneur experience. We’re going to interview other entrepreneurs and founders and business owners and you know, about not only their experiences, but also we’re going to talk to some spouses of those people and just kind of get a feel for what is this life really look like? What are the challenges, what are the, what are the benefits? You know, how do people perceive life as an entrepreneur? Right? And then the other segment is called investor insight, and we’re going to be talking to angel investors, VCs, PEs, and various realms. And just try and find out what is it that makes you invest in something, what is it that has an investor say yes or no to a project? And how can someone get a yes from you as an investor. So over, over the next few months, we’ve got a bunch of great guests. Some of whom I’ve already talked to in the episodes are in the process of being edited and scheduled. Some of whom are on the schedule and I’m really excited to talk to. And, you know, we’re going to get so much, really great perspective from other people about what is this startup journey? What does this thing look like? What does it mean? How do I engage with it and, and be as successful as I possibly can be if that’s something that you want to do. So, but today’s episode having a midlife crisis, which is manifesting itself in many, many different ways. The biggest of which is actually in how I’m engaging in Precursa and, you know, sort of what’s happening. And this is not intended to be a self-serving episode. What I’m intending to bring is first of all, I seem like I have this together a lot, right? I mean, I interview guests, I coach people, I’m a consultant and an advisor to lots of startups, I’ve built successful startups. And so it, it could seem like as a listener, you might go, wow, that’s really great for Cynthia and for her company, but she has so much experience and she has it all together and she knows what she’s doing. And that’s, it’s just not always the case. There’s a perfect storm, a confluence of events that has led us here today. And what that perfect storm is. I turned 40 a few days ago, you know, which is fine, age is just a number, whatever, but all of a sudden, there’s like sort of this thing that happens, which is that I feel like now I’m supposed to be an adult. I feel like now I have, you know, I have 25 years working as an entrepreneur, working in tech and in startups. And that, that means that I – I mean, that’s more than half my life, which means that I should, and I’m putting should in quotes, should be in a different place. Like I should have more money saved or in retirement, I should, you know, have more larger success under my belt. I should have had a, you know, a hundred million dollar exit by now. Like, so what’s happened is I turned 40 and the fundraising process for Precursa, you know, it’s just, it’s just taking a long time and there’s some realizations we’ve come to about why that is. And, and the one objection that we get every single time we talk to someone is a big indicator for why it’s taking longer. And so, you know, like any good business and, you know, like I would advise any of my clients, we have found small tweaks and pivots along the way in order to start addressing that and to re either remove that objection or show people that we have a plan that deals with that. And, and I’ll talk about that, you know, before the end of the episode, but it’s just taking a long time, you know, I mean, and it frustrates me to no end, every time I talked to someone new who knows me and who loves me, and they’re like, it’s only half a million dollars. Like, that’s just not a lot of money. And I’m like, I know, so can you help me find it? You know? And, and then there’s this piece of this whole thing, which is that as much as Paige and Sarah are my co-founders, they’re my partners, they’re they do so much amazing, incredible things to help keep us on the right track. 05:33 You know, we have now three developers who are working on the project. We have our UX designer and UX engineer, who’s doing phenomenal work, bringing this to life in a way that actually works for users, right. Which is amazing to watch. We have our video guy. He’s like all things video for us right now. And behind the camera. There are a lot of people who are working on this project and they’re all doing amazing jobs, and none of this is going to work ever without them. But ultimately it comes down to me and not me to do all the work or me to, you know, have all the expertise, but it comes down to me as the CEO, as the captain of the ship to give the right guidance to the people who are doing phenomenal work, to put the right people in place to have the right conversations and, you know, clear as day having fundraising conversations as the CEO, as the captain steering the ship that comes down to me too, because if an investor doesn’t believe that I have the capability and the, I have the skills and abilities and talents are that I am, I’m coachable enough to learn those things. As we go to make this successful, they won’t invest because especially in early stages, you know, people who are investing in Uber now, probably aren’t investing in the team. They’re investing in, what’s come before they’re investing in the future. They’re investing in a financial statement. Maybe they’re a little bit investing in the team, but let’s be honest, private equity when they get ahold of something, they’re turning teams over sometimes constantly, you know, multiple times in a year, right. But in the early stages, your idea and the execution of that idea that comes down to you as the person who ideated it, and, and ultimately as the CEO of the company, it comes down to you. And so there’s like I said, it’s just this perfect storm of like, have I done enough with my wife? Am I really in the place where I thought I would be?  The answer is no, but why did I think I would be there? And why am I judging the journey? Right. Like all those questions, but combined with this whole thing that people are spending time and energy and money and everything else on ultimately comes down to me and my ability to make the right decisions and choose the right people and do the right things. And then combined with how long it’s taking to fundraise. And just some of the realizations that we had in the business lately. Right? So maybe midlife crisis is kind of the wrong word, but something happened, you know, it was like, it was like, I’m going along and I’m in my thirties and this is all great. And I’m gonna make this thing happen. And then the day I turned 40, it was like, there was this realization that the likelihood is just say, my life is probably more than half over now. And for some reason it was like, did I waste half of my life? Was that really a waste? I mean, I don’t know that I can look at it that way. I can’t, because I can never be upset. I just, I, I don’t have a space for regret. I mean, this episode kind of makes it sound like we’re talking about regret, but it’s not, it’s not regret everything. I’ve been through everything that I’ve experienced, even the mistakes I’ve made, the successes I’ve had. Like all of it has gotten me to the place that I am today. And the reality is I love who I am. I, I’m not perfect. I’ve got flaws, I’ve got secrets, I’ve got hidden things, but I really love who I am. And I love, I love how, you know, in my twenties, I was telling this to my sister the other day. I was like, in my twenties, I spent so much time trying to be bold and trying to have my way and have my opinion be known and trying to speak my mind. And I alienated so many people. I ruined so many relationships and all of that experience has gotten me to this place now where I know how to be diplomatic. And it doesn’t mean that I’m any less clear about who I am or that I’m any less vocal necessarily, but I can honor other people and their individuality and their vocalness and, and, and their journey at the same time. Right. And it’s not my way or the highway, and it’s not, I’m right. You’re wrong. That is a really cool place to be. I mean, the number of times in the last few months where I’ve been in situations that in the past, whether it’s with David or with a friend or, you know, and I’m not perfect, I’m thinking of a particular friend of mine who we just have sort of lost each other for, and I’m not sure why, you know, so that’s another thing sort of contributing, but you know, so many situations I’ve been in that would have led to cutting someone off or just abandoning, abandoning ship right. 10:34 In, in, in a relationship or, or, you know, ruining a relationship or whatever. And we’re, I’ve just been so much more level headed. So I can never feel regret for that. Like I just, can’t what, what I am experiencing is if it’s half over, if the likelihood is, I mean, sure, we could, I could live to that. You know, my wealth advisors, like we need to plan for you to live to 96. And I’m like, oh my God, I don’t know if I want that. But if, you know, if, if that’s the case, what am I doing with the rest of it? How am I creating a better world for my family and a better world for the people that I love and my friends and people who I may not even know who are touched and impacted by Precursa or by, you know, whatever else I might do in the future. Right? Like, how am I, how am I doing it so that it’s not so much about me, you know, and transparently that’s, that’s tough because I have things I want, I mean, I, I still want, I want the billion-dollar exit. I want the unicorn tattoo. I want, I want the ability to put a hundred million dollars into figuring out funding and equity. So how do you have goals and have desires and have drive and ambition and not be selfish. And I don’t, I don’t have any answers and I, I just don’t have any answers. And I guess that’s why it kind of feels like a midlife crisis because it’s having this impact that I can’t explain. And I haven’t been able to just logic my way out of it. Right. It’s like, this is just, I feel like this is one of those things where I just need to feel it and get it. And I don’t know. I don’t know. I, so the, the analogy that came to me the other day was all of us have worked for someone. Right. And, and even though I have, you know, run several businesses as a consultant and, and, uh, an advisor and a coach and whatever else we want to, we want to call helping other people work through things, and yes, I have done it. But when you coach and consult, you’re still like a backup singer, right. You’re, you’re not the one who has to make the thing happen. You’re providing strategies, you’re giving oversight. Sometimes you have actual tasks to do, but ultimately someone else is the one who has to take that and turn it into a thing. And being the CEO of something, you know, my exits have been accidental when I started my first company. It was about, I got fired from being a barista and really missed having money to go do stuff. Right. And so I was like, okay, well, I’ve been doing this web thing. Let me get some people to pay me some money to build them some websites. And oh, if I put them on maintenance plans where they pay me a little bit every month and I have 10 or 20 people doing that, all of a sudden, I didn’t need that paycheck for my barista gig anymore. Right. I mean, so I didn’t set out to build something that was going to be acquired or that was going to be big. And so when I, you know, when it was getting to a point where there was actually really some cool stuff happening, and then I landed a really good client, one of my competitors really wanted it. And so they came in and bid on my company. Right. I mean, that, wasn’t something I set out to do.  And it wasn’t even something I set out to do the next time. I mean, it was really cool. And, um, you know, we had a product that time, which was cool cause the, the, the exit was larger, you know, and I was like, Ooh, product. That’s cool. I didn’t have to be there for it to be making money. Right. Like I wasn’t having to do as much work, but those are accidental. I didn’t set out to do that. And so when it happened, it was just cool. This is different. Like I said, the analogy that I keep hearing in my head is the difference between being a backup singer, where you show up and do the job. And, you know, you have to be a decent singer, but you don’t have to be phenomenal. I mean, you really don’t. In fact, they look for backup singers who can blend and mesh and, you know, that’s a skill its own. Um, but how many times can you point to where a backup singer actually became a front person or became a solo artist and was very successful? It’s rare. Uh, Sheryl Crow is one that I can think of. She was backup for Michael Jackson for a while, and obviously has had a very successful solo career. That’s rare. So, you know, we’ve all worked for someone or we’ve all coached someone, or we’ve all done something, but how do you go from that to being the person saying, I’m building a unicorn, I’m building a company with the intention of selling it for a lot of money because of the level of value that it provides. And that value in this cases, we’re challenging the, the preconceived notions of an entire industry. You know, we’re saying it’s stupid that we accept that nine out of 10 startups ultimately fail. Why, why are we okay, accepting that that’s not okay. 15:47 And we’re challenging that, and we’re saying it doesn’t have to be that way. And in fact, this is exactly what technology is good at. That’s huge, it’s bold. And it’s grabbing the mic and stepping out in front of the biggest crowd. You can imagine at Wembley arena or whatever, and saying, I’m gonna, I’m gonna, I’m gonna create an experience for you. Every single one of you is going to have a magical moment. That’s bold, it’s brash, it’s, it’s terrifying and it’s easy. It would be easy to let the fear drive what comes next. There are so many times where I find myself thinking it got to, I got too big. I talked too big. I made big promises. I believe something that is bigger than me and is that hubris. And there’ve been times where I’m really scared. And there are times where I wonder, can I really do that? And I guess this is just one of those times kind of on the heels of turning 40 and wondering if I’m doing the right thing with the second half of my life, right. I guess all there is to do is I make the bold statement. I’m brash, I’m unashamed because I just I’ve worked with too many entrepreneurs and I’ve heard too many stories. I just, I don’t believe that that that many people need to go through that level of pain, potential financial ruin. And for whatever reason, this vision came to me, this thing is asking me to make it real. What would be the only ones? No, of course not the second way, prove what we’re going to prove next year. And the second we start bringing on incubators and accelerators and entrepreneurs start getting results and an investor start getting results. Other companies are going to spring up. I welcome it, but I’m, this is my path to forge for the time being. There’s a forest and there is no path. And it’s for whatever reason, I’m, I’m the one right now. And then I’ll tell you, it would be so much easier to just keep doing the coaching and consulting thing and, you know, build a few million dollar a year business and just be content, right. Somehow that’s not the journey. You know, I said earlier, you know, um, I like who I am. I love who I am. Um, but I’m not perfect. And I have secrets and there’s hidden things and mistakes I’ve made. And some that people know about. And some that I’m pretty certain nobody knows about. And, you know, selfishly one of the biggest risks of actually building something big as spotlight that you come under. And I, I like feeling like, you know, you, my faithful podcast audience, and as it grows, you do see me a certain way. And you, you do buy in just because of my passion and because, but also because of my, my knowledge and my experience and my history, right? Like, but that’s vanity. And I guess what I’m saying is this is what the trough of sorrow, there is no vanity. When you question everything, there is no vanity when you’re certain that your vision is right. And you’re certain that you are the one that can make it happen and that you have brought the right team together and that all the pieces are falling into place. And yet the thing that you need most in most cases, money isn’t coming together. And is that some huge sign and you’re just ignoring it because you do have the resources and the ability to keep bootstrapping. But are you, are you ignoring something? Are you living in a fantasy? Are you? And I think, you know, they talk about the trough of sorrows in a, in a lot of different ways, but a lot of it has to do with fundraising and how ridiculous that, you know, the startup world is designed for raise a bunch of money. Don’t worry about making money, worry about growing really fast and, and getting the big exit and let someone else figure out how to make it profitable or let someone else figure out how to scale it in a way, you know, like, I guess what I’m saying is all the statistics and all of the, the assumptions and the preconceptions that we’ve just come to accept nine out of 10 fail, 42% are going to fail because nobody wants what they’re building as if that’s not preventable as if it isn’t all preventable. 20:55 It’s just a huge, it’s, it’s a burden to carry and experiencing moments of self-doubt. Those are the moments when I can’t stress enough, how important it is to have people around you who get it. It doesn’t even matter if they get what you’re doing, but who believe in you? I mean, Sarah jolly and I were on the phone the other day, and I was sort of, you know, trying to kind of work through some of this and talking out loud with her. And she said, you know, Cynthia, it’s, you’re, you’re working through what you’re working through and that’s okay. She says, just know that I see the vision. She’s like, I see it. And I have this picture of you coming out, coming out the other side of all of this triumphant and in a way that provides hope for other people who are struggling with it, or gives a path for someone else to follow. She said, that’s, that’s the hardest part right now is you, there is no path for you to follow. You’re making it so that other people can follow it. And she said, that’s. She said, I, I know it’s all gonna, it’s all gonna be great. And she said, so I’ll hold that. Even when you can’t, everybody needs a Sarah jolly. We say that all the time, because it’s true in every context. But in this context, I’m saying everybody needs someone who’s on their side. And whoever that is for you, the trough of sorrows is when you need those people, most like it’s such a stupid word. I hate that word trough of sorrows, like, oh my God, this deep dark it’s. So even that feels like a vanity thing to me, right? But this experience, this questioning, this, this build it and the money will come build it and they will come, right? Like that. You know, we all kind of buy into that. And this experience is real. And this is, this is the time when you need those people. The most, you know, you’re Sarah jollies and you’re David oper mins. And I don’t have any answers right now. There’s, there’s a bunch of different places you might be in as a listener. You know, you might be someone who’s like, I love the idea of being an entrepreneur. I would totally love to come up with an idea or I have an idea, but I’m not quite sure what to do or how I would turn that into, you know, a business or into a startup that could get funding or, you know, or maybe you’ve been down this path once before, several times before maybe you’re in it right now with something new. My goal here isn’t to make it seem hard, or it’s none of that. It’s only to remind us all you’re not alone. Being an entrepreneur is, can be very lonely, particularly being, like I said, the CEO, cause ultimately the only person on the planet who can make this thing succeed or fail or decide that it’s time to keep going or stop. It’s you, that’s a, it’s an incredibly lonely place to be. And having people around you who believe in you and listening to that, when you feel the loneliness and building a team that believes in what they’re doing, it makes all the difference. And sometimes just hearing that someone else is going through the same thing, you are someone else’s experiencing the same thing. You are, someone else has been where you are. Sometimes that can help too, because while it’s lonely, you’re not alone. I’ve been listening to the podcast startup. I can’t recommend it enough. It’s by Gimlet media. It’s actually the first season and a half or so is all about how did Gimlet become a company from an idea that Alex Bloomberg had. And then in later seasons, they’re following other startups are interviewing other other founders. And when you look at really successful founders, I mean, one of the, one of the seasons, they did a whole series of episodes on, um, dove Charney, who, who was the original founder and creator of American apparel. Right. And he built an enormous empire. I mean, there’s no other way to say it. He’s doing it again after, you know, all the scandals and getting, getting fired from, from it and, you know, losing his equity and all the things, but he’s manipulative and he’s very passionate and very charismatic, but manipulative and, and immature in a lot of ways. And you know, there’s a lot of examples of that. 25:47 And is that the only way do I have to be charismatic? Do I have to get people to buy into whatever I’m believing in or selling or whatever fantasy, you know, I’ve concocted today in order to be successful? Is that required? Because I don’t want to be that person. Perfect. Imperfect, whatever. I don’t, I don’t want to be manipulative. I don’t want people to turn around and go, huh? How did I get, how did I get here? Is that possible? I don’t know. Do I have to be someone that everybody loved that everybody loved her and everybody believed in her and everybody? Is that the only way? I just, I can’t, I can’t believe that I guess. And I, I don’t, I don’t think I accept that, that people can’t have free. Will the people can’t speak objections or question you? I don’t know. I just, there’s lots of examples of people who have manipulated, who have done shady things who have, uh, I’m not going to say conned, but it feels like being conned sometimes. Is that the only way to be successful? I don’t know. I hope not. All I can do is listen to my intuition, hold the vision, take the coaching. As it comes, recognize what actually fits in the vision and what doesn’t, and ultimately trust my path and trust myself because although a lot of other people have had success, they’ve done things really well. They’re not me. And this isn’t their journey and this isn’t their vision and this wasn’t given to them. So it might look different. Maybe it’s not a midlife crisis. Maybe it’s just the trough of sorrow says, find your SAR, Sarah jolly. That’s, that’s my advice today. Find that, find the person, find a couple of them, who they believe in you. And when they say they believe in you, you believe them. It’s not intended to get rid of all of the things, all of the other things. And it’s not going to make you feel better or less lonely, but you won’t feel alone. And I think, I think that’s a worthy aim and a worthy goal. Maybe the only one. So I’m 40. That’s crazy is I was listening to an episode of startup the other day. And you know, I’ve never, I don’t know what Alex Bloomberg looks like. I’ve only ever heard him on this podcast and through other Gimlet podcasts. And so in my mind, he was this late twenties, early thirties, whipper snapper, who was like, I’m going to build a podcast network. And, you know, cause he was a white, young, white dude, of course that was going to happen. Right. And he was T he was doing a pretty raw vulnerable episode with a business coach and mentioned that he was 50. He had turned 50 and I literally rewound it like three times. Cause I was like, did he just say 50? And it gave me hope. You know? I mean, one of the biggest fears I have right now is I am now in my peak earning potential peak career years. Right. I mean, I could, I could go find a company who would hire me for a lot of money stack away, a lot of money in a retirement over the next 10 or 15 years and know that I’ll be okay. Right. And that path doesn’t involve a unicorn. It doesn’t involve, you know, a windfall of 10 or 20 or a hundred or $500 million or whatever. Right. So that, that, that path doesn’t have the wealth upside potential, but it’s safe. And it means I won’t be eating dog food and working at Walmart when I’m ready, you know, as a retired person or never retiring. Right. And there’s something right now that is like, am I wasting? Am I spending that time building a startup? Is that a waste? Am I hurting myself? Am I hurting my family? Am I, is this for nothing? And if I, if I think about when Alex was saying he was 50, I was like, oh, and he just started that, that they were in like their second or third year. It just kinda gave me a little bit of space, like there’s time and I’m not going to be destitute and it’s going to work out promise. We just don’t always see how. And I think that’s probably the scary part. You know, I’m a control freak, which is good when you’re the CEO of a company and it’s up to you to execute on a vision, but also not good. So I’m 40, I’m building a startup. It’s been a while since I built a startup, it’s been a while since I had an exit and I’ve never gone into it with the intention of building something big and exiting for something big. 30:55 So it’s different. It’s scary. And in, in this way, I’m a first-timer and the more I think I can give into that for myself and pitch from that place. Yeah, I’ve done. I’ve done stuff. I’m not new, but I’m a first timer at this. I think that changes the game a little bit. Maybe it removes the chip on my shoulder. I’ve felt so much lately. Like I have this huge chip on my shoulder. Why can’t I raise money? Don’t look at my history. Look at my past, look at the exits. I’ve had like, look at my successes. Aren’t I worth investing in. I mean the light, I have a higher chance of being successful because of my, of my past. But this is a whole new thing. How many people do I know who have built really successful companies and then gone on to do a lot of failures. And I think just being honest about those realities, that’s all there is. All right, well find a Sarah jolly. You’re not alone. Even when you feel lonely and uh, whether it’s always happier, not as always happy entrepreneuring. And I will see you all next time. Thank you for listening to this episode of Precursa: The Startup Journey. If you have an idea for a startup and you want to explore the proven process of turning your idea into a viable business, check us out at precursa.com. Make sure to subscribe to this podcast wherever you listen to podcasts, so you never miss an episode. Until next time…