35. One Woman's Empowering Journey From Wall Street to Solopreneurship With Charlotte Keesler

Show Notes

From investment banking and VC firms to a startup focused on reimagining the experience for next-generation women in the workforce, Charlotte Keesler has seen a lot. She shares her journey as a solopreneur in this episode.

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*Formerly known as Solopreneur: The One-Person Business Podcast*

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Charlotte Keesler (00:00):
This will solve this person's problems. But you know what's also important is solving problems for corporates in this macro environment and aligning incentives. So how can you create a product that is both beneficial to the user, but also could be a game changer from a corporate perspective,
Intro (00:17):
Bigger doesn't always mean better. Welcome to the One-Person business podcast where people who are flying solo in business come for specific tips and advice to find success as a company of one. Here are your hosts, Joe Rando and Carly Ries.
Carly Ries (00:37):
Welcome to the One-Person Business podcast. I'm one of your hosts, Carly Ries
Joe Rando (00:42):
And I'm Joe Rando.
Carly Ries (00:43):
And in honor of Women's History Month, we've had some pretty amazing ladies on as guests over the past few weeks, and Charlotte Keesler is no exception. Charlotte started her career in investment banking on Wall Street, after which she moved to Los Angeles to join an up and coming venture capital firm that grew five times during her time there to over 1 billion in AUM. Charlotte is now building a startup focused on re-imagining the experience for next generation women in the workforce through using technology to revolutionize mentorship, peer-to-peer interactions, and provide value added content. So Charlotte, welcome to the show.
Charlotte Keesler (01:17):
Thanks so much for having me, Carly
Carly Ries (01:20):
Charlotte, I'm always so intrigued by your business. Can you elaborate on it a little bit and what you're currently doing in the background that led you to want to be a one-person business?
Charlotte Keesler (01:27):
So what I'm working on currently kind of part of that larger platform that you mentioned in the intro, is I'm creating an app that guides users through building a board advisors for her career. Essentially systemizing and digitizing mentorship. That's kind of the first piece of this larger company I'm imagining that supports NextGen women in the workforce. In terms of background, that led me to this place that I'm at now, as you mentioned, I started in banking and then moved to venture capital and found during my time at both of those firms, that I just absolutely love working on things in the consumer realm. At the same time, I'm very passionate about building things and solving problems. So the next logical step was to create my own company, kind of focused on a pain point that I experienced myself.
Carly Ries (02:31):
Makes sense. So, question for you. You've worked for such large companies. What is your personal "why" for staying small?
Charlotte Keesler (02:38):
So my why for staying small, I would say that while I was working in VC I saw a lot of startups hire too many people too quickly. I think that can be a really tough mistake to make because although, technically, employees can be viewed as like a variable cost, they really should be thought of as fixed costs because they're very hard to remove both legally and from a workplace culture perspective and have a really negative impact. I think that's kind of been illustrated in the press recently with Glossier laying off a third of its corporate employees and, and kind of the backlash from that. So, I just really want to build kind of intentionally and right now that means staying small
Carly Ries (03:32):
Makes sense to me. So let's get into the nitty gritty a little bit. You have a very unique business, but you have to have competition in some sense. So how do you distinguish yourself from others in your industry? Or I guess, how do you position yourself?
Charlotte Keesler (03:47):
I think in terms of thinking about what I'm doing and how I might differentiate. First and foremost, I want to create something that solves a problem and provides real value. I'm doing this from the perspective of the user herself. So I think that, in itself, is kind of a unique point of view to be building something from. Not just like, "Hey, I see this problem from kind of an analytical perspective. I think this might solve it. " It's like actually having a very intimate understanding of the user's problem and their needs. That's definitely a differentiating factor, but I also am creating that kind of in the mindset of, of the, of the venture mindset, right? So it's like this will solve this person's problems, but what's also important is solving problems for corporates in this macro environment and aligning incentives. So how can you create a product that is both beneficial to the user, but also could be a game changer from a corporate perspective? And that's kind of where things start to get powerful.
Carly Ries (05:02):
Absolutely. Then the other question I had, just in terms of separating yourself and getting part of the share, how are you going about getting clients?
Charlotte Keesler (05:12):
So I think it's a little early to say that . We're still developing the technology. I have a strategy in place to do so, but I wouldn't say I'm necessarily in a position to share any foolproof tactics or learnings for others.
Carly Ries (05:31):
No, I love that. Just being transparent with that. So many people are in your shoes where they're in the development startup phase of their company. Even though it wasn't really the answer to that question, it was the perfect answer to that question,
Charlotte Keesler (05:43):
. Ok, great.
Carly Ries (05:44):
And let me ask, coming from the corporate world where you're probably surrounded by people all the time, do you ever feel lonely as a solopreneur? And how do you combat that if you do?
Charlotte Keesler (05:53):
Luckily my fiance works in banking with a focus on technology, so it's really nice. We both work from home and we're able to talk to each other a lot about work. Him kind of from more of a macro perspective, you know, publicly traded companies and me coming from a much smaller scale background, you know, in terms of working in VC but that definitely helps a lot in terms of, support and comradery.
Carly Ries (06:26):
Absolutely. Congratulations on your engagement. I don't think I knew that. So the journey to being a solopreneur can definitely be a daunting one. Is there anything you wish you would've known ahead of time before starting this journey that you know now?
Charlotte Keesler (06:41):
I would definitely say that I did not quite understand the stamina, discipline and patience involved in this. It's definitely a long journey and there are days where you get to work on really exciting things, but there are also days when it feels like a bit of a slog and you have to work on much less exciting things. So I think there's this notion of being inspired or motivated a hundred percent of the time, which is just not really true. It's so much more about discipline and yeah, there are days where I'm super excited about stuff, but there are days where I have to work on, you taxes, and other stuff like that. So it is just making sure that every day you're taking a step towards your goal, whatever it may be.
Joe Rando (07:29):
Charlotte, can I say something? I think anybody that understands what's really involved with starting a business and probably especially a One-Person business, probably doesn't actually do it. .
Carly Ries (07:40):
, Yeah, it's funny, I was laughing that you brought up taxes because I think I've mentioned this maybe every other episode, that of all the things that go into One-Person Business, my least favorite is taxes. I owe the world to my CPA for helping me out with that. To piggyback off of that, what are your favorite and least favorite parts of being a solopreneur?
Charlotte Keesler (08:01):
I think in terms of my favorite part is I love being the decision maker and seeing my vision progress over time. I definitely have a passion for the building and development of things and ideas. That's what gets me really excited. My least favorite thing is the pressure associated with it. It's really all on you and there's no way of getting around that. So, definitely struggle with that some days, but keep forging ahead.
Carly Ries (08:35):
Yeah. When things go wrong, it's all on you, but the good thing is when things go right, it's also on you. So glass half full in that situation. So I have to ask you, we were talking about your fiance and how you guys talk about business quite a bit, and for solopreneurs, sometimes it's hard to separate their work life balance because everything blends together. It kind of takes over. Do you have any tips for separating your work life and your personal life?
Charlotte Keesler (08:59):
Yeah, I'm a big list girl. I have massive to-do lists and every day I actually have a list of stuff that needs to get done as it pertains to my business and work and a list of things that need to get done personally. That includes working out if that is a priority that I wanna make sure gets done. So putting together these attainable lists and just making sure I get at least 80% of it done every day is a good way to not allow my life to just be a hundred percent one or the other.
Carly Ries (09:34):
So let me ask you, how do you stay focused enough to get that to-do list done when you're in charge? What makes you sit down and actually get it over with?
Charlotte Keesler (09:43):
I think it's just about before discipline and using the lists. It really is like every day, you wake up, you have the list, you could take, start ticking through it. And just having that discipline to do that helps to get things done because once you start doing things, it makes it easier to do more things. Then, sometimes you'll have chunkier problems or thinking about what's the right next step to take . In thinking about those things, I like to get outside and move around and get the juices flowing. That can be really helpful whenever you're feeling stuck. Just physically change locations and move. That can help your brain move.
Carly Ries (10:23):
Yeah, it is amazing what that can do for your mind, for sure. Now a quick word from our sponsor.
(10:30):
You may be going solo in business, but that doesn't mean you're alone. In fact, millions of people are in your shoes running a One-Person business and figuring it out as they go. So why not connect with them and learn from each other's successes and failures? At LifeStarr, we're creating a One-Person business community where you can go to meet and get advice from other solopreneurs. Be sure to join in on the conversations at community.lifestarr.com.
(10:57):
so let me ask you, becoming a solopreneur, you don't have this structured life that a lot of people do in their nine to five jobs. You don't always know what's coming. Not that it's a perfect science in a nine to five, but there are a lot more curve balls. There's a lot more uncertainty running your own business in regards to income, schedule and all of that. How do you embrace that?
Charlotte Keesler (11:16):
I think what helps me, usually, I don't think about the uncertainty of things on a day to day basis. Obviously sometimes you do, and jwhat always helps me is thinking about the greater goal of what you're trying to do. That always gets me really excited whenever I start thinking about that. Then, looking backwards and seeing how far you've come. I think sometimes, the uncertainty can make you feel like, What am I doing? Why don't I just get a job where I get paid weekly and all this stuff. It's like, well, look how much you've done and look what you're trying to do. This could be something really big and you've already done a lot. So I think reframing the uncertainty in those ways can be helpful.
Carly Ries (12:03):
That's a great way to look at it. You ended on a positive note and I'm gonna flip it back to a negative note, but then we'll go positive again. What has been your biggest mistake so far with setting up this business?
Charlotte Keesler (12:16):
I would say I would perhaps have done things in a different order. So, you start going down one path and then you realize, all right, I've got to take a couple steps back and kind of go this other way because that was a little bit preemptive or whatnot. I think the ordering of everything perhaps could have done a little bit of a better job with that. But at the same time, you're figuring it out as you go along so that's bound to happen in a certain sense, but you learn from it and you move on, right?
Carly Ries (12:50):
Yes, well said. So, okay, we'll flip it again. What has been the moment where you're like, Okay, I've got this, I'm on the right track, let's do this.
Charlotte Keesler (13:00):
I think one of the more recent moments, just in terms of this initial technology product that we're rolling out, I knew I wanted to do and create something around mentorship because mentorship can be so extremely beneficial for both individual and organizations. And like I said, I'm trying to align incentives there. Just to give a few stats, mentees are promoted five times more often than those without mentors. Then in terms of an organization, the retention rate with organizations for mentees is like 72%, mentors is 69%, and then employees not in a mentorship program, it's 49%. So it's a really big difference. I was thinking about, how can I create something around mentorship and what can we do there, and ended up coming up with this idea to basically create a tech product that walks the user through creating a board advisors for their career, started talking to people about it, and it was really resonating. I could just say one sentence and people understood what it was and or what it will be. So that was, I think a bigger aha moment. Okay, now we can build this technology product and launch that. Then we can start building, a lot of other functionalities off of it to create this work life ecosystem for the user, but anchoring this beginning point was a pretty aha moment.
Carly Ries (14:32):
Absolutely. Sounds like it. And those stats that you just shared about mentors and mentees are just fascinating. So I have to ask, what is the best piece of advice you've received as a company of one?
Charlotte Keesler (14:43):
I would also say it might be too early to tell . We'll see. Everything's still kind of in motion, so I don't really know what to share with you there yet.
Carly Ries (14:56):
That's okay. We'll have you back on a year from now and see if that answers changed.
Charlotte Keesler (15:00):
Yeah, right.
Carly Ries (15:01):
What tools do you use to manage your business?
Charlotte Keesler (15:04):
Like I said, I use a lot of lists. I keep all in One Note on my computer. In terms of visualizing those lists and putting them into focused pieces of different projects, et cetera. I use Monday.com, which I don't know if you guys are familiar with, but that's really helpful. And Trello also I use to coordinate with different external teams that I've worked with. Those are all really helpful from a process management perspective. Then of course there are a million other different online applications nowadays that we use, but I think those three have been really helpful in terms of organization.
Carly Ries (15:47):
I visited Monday.com site once, and I have continued to be, I'm convinced, their number one target around the internet ever since , their ads pop up everywhere,
Charlotte Keesler (15:59):
. Yeah, no, that's great though. You should try it.
Carly Ries (16:01):
Charlotte, do you have a favorite resource or multiple resources to help people on their solo journey? Whether it pertains to your business or not?
Charlotte Keesler (16:09):
I think especially when I was first starting out, I just listened to tons and tons of podcasts all about small businesses or business creation or startups or venture, whatever it was. I found those to be extremely helpful just in terms of a pretty easy, free way to learn about bunch of different things as it pertains to startups. Also, one of my favorite books on tape that I listened to towards the beginning of this journey was originals by Adam Grant. I would definitely recommend that to anyone listening as well.
Carly Ries (16:49):
Good to know. Do you remember any of the names of the podcasts that inspired you?
Charlotte Keesler (16:55):
Yeah, I can rattle some off. I love anything that Brene Brown talks about. Skimmed from the Couch is great as well,. How I built this is wonderful. Just to name a few.
Carly Ries (17:09):
Okay. Adding that to my personal list as well. . Thanks. So those were actually our big questions in regards to your business specifically. We always like to inspire other solopreneurs and see what works for people going it alone. So I have to ask, what is your favorite movie that always puts you in a good mood?
Charlotte Keesler (17:26):
? Yeah, sure, my favorite movie and I get made fun of for this a lot is Forest Gump.
Carly Ries (17:35):
A great movie, . Who's making fun of you?
Charlotte Keesler (17:38):
, everyone. It makes me tear up every time. It's just the ultimate story of perseverance and how someone can do such impressive things in their life. So I love it.
Carly Ries (17:55):
Charlotte, if it makes you feel better, I always say Tommy Boy. So yours is much more inspirational than Tommy Boy , but I'll stand by it till the end. What is your favorite song to pump you up?
Charlotte Keesler (18:07):
I feel like I listen to different songs at different points depending on my mood. But one song I tend to listen to on repeat is Venice Venture, which might be just because I live right near Venice. But it's great. I listen to it on repeat while I work a lot.
Carly Ries (18:31):
Well, we might need to add that to the show notes so people can join you.
Joe Rando (18:35):
Who did Venice Venture?
Charlotte Keesler (18:36):
Big Wild. I'm not even a fan of the artist. I just like the song.
Carly Ries (18:43):
That works. No need for excuses. And Charlotte, we're on our last question. How do you define success?
Charlotte Keesler (18:50):
I think success is definitely different for everyone. For me, success will be building a sustainable business that solves a real problem and helps real people. It's as simple as that.
Carly Ries (19:05):
Easy enough, no need to make it complicated. Well Charlotte, thank you so much for coming on today. Where can people find you if they want to learn more about you and your business?
Charlotte Keesler (19:14):
You can find per the work edit on Instagram and there's also a link in the bio that you can click on to add your email to our list so you can get email notifications and updates and when the technology is out and app is able to be used, you can sign up. So, definitely check that out.
Carly Ries (19:38):
Awesome. Well just let us know what we can do when the time comes to help promote that. Cause we would love to.
Charlotte Keesler (19:42):
Yeah, definitely. Thank you.
Carly Ries (19:44):
And there you have it listeners, thank you for tuning in to today's show. To listen to other episodes and subscribe, be sure to visit lifestarr.com/podcast. Or you can find us anywhere you listen to your shows. We'll see you next time.
Closing (20:00):
You may be going solo in business, but that doesn't mean you're alone. In fact, millions of people are in your shoes running a One-Person business and figuring it out as they go. So why not connect with them and learn from each other's successes and failures. At LifeStarr, we're creating a One-Person business community where you can go to meet and get advice from other solopreneurs. Be sure to join in on the conversations at community.lifestarr.com.