Unlocking Capital Opportunities

Hosted By Lauren Conaway

InnovateHER KC

See All Episodes With Lauren Conaway

Kelly Ann Winget

Today's Guest: Kelly Ann Winget

CEO - Alternative Wealth Partners

Dallas, TX

Ep. #1236 - Unlocking Capital Opportunities

In today’s Startup Hustle episode, Lauren Conaway and Kelly Ann Winget, CEO of Alternative Wealth Partners, discuss unlocking capital opportunities. Listen to Lauren and Kelly Ann talk about alternative investment and when it is better for startup founders than VCs. They also discuss the importance of building and engaging a community, identity, exclusiveness in the investment space, and representation in entrepreneurship.

Covered In This Episode

Venture capital may be a traditional route for funding, but it is not the only one. Alternative Wealth Partners provides a platform to connect entrepreneurs with off-Wall Street opportunities.

Listen to Lauren and Kelly Ann talk about her background in the oil and gas industry. They also discuss alternative investments and diversification in that industry for capital opportunities. They agree on the importance of focusing on building and engaging your community to unlock these opportunities.

Get Started with Full Scale

The conversation turns to privilege, identity, exclusion, and representation in entrepreneurship and investment. They wind down with Kelly Ann revealing which talk show she wanted to be on as a guest.

Alternatives are always good. Learn how to unlock capital opportunities in this Startup Hustle episode now.

Best Entrepreneur Podcast Available on Spotify, Apple and Google Podcasts


  • Kelly Ann’s background (1:18)
  • Alternative investment to unlock capital opportunities (7:17)
  • Why alternative investments are sometimes better than VCs (9:20)
  • Alternative investments and diversification in the oil and gas industry (14:20)
  • Focus more on building and engaging your community (21:52)
  • Identity and exclusion in the investment space (30:37)
  • Privilege, identity, and representation in entrepreneurship (37:36)
  • Which talk show would Kelly Ann like to be a guest on? (40:33)

Key Quotes

There are companies that are spending a lot of time and effort trying to raise capital from VC when they should be really focused on either establishing a better relationship with a better bank or finding a private equity or private investor who can focus on the growth part of their business because they might be beyond venture or not make sense for that type of capital.

– Kelly Ann Winget

Founders should really focus on finding investors that align with what they’re doing because there are a lot of people out there. And then, from the investor’s perspective, you can actually have a lot of impact by using your own money to make these investment decisions outside of just, well, my advisor says Plan A is best for me.

– Kelly Ann Winget

A lot of coaches and consultants out there are really heavily focused on making your pitch deck perfect, and you’re making your pitch perfect. The reality is that, especially for early-stage businesses, more focus should be spent on building your community because that’s where your first check is going to come from.

– Kelly Ann Winget

When you engage the community around you, you create brand advocates.

– Lauren Conaway

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Rough Transcript

Following is an auto-generated text transcript of this episode. Apologies for any errors!

Lauren Conaway  0:00

And we’re back. Thank you for joining us for yet another episode of the Startup Hustle podcast. I’m your host, Lauren Conaway, founder and CEO of InnovateHer KC. And I gotta tell you, friends, today’s episode of Startup Hustle is powered by FullScale.io. Hiring software developers is difficult, but Full Scale can help you build a software team quickly and affordably. And they have the platform to help you manage that team. Visit FullScale.io or visit the show notes to click the link to learn more. All right, friends, we have with us today. Now, for those of you who listened to my episodes of the show, you know that I love talking about money. I love it. Love it, love it, love it, love it. And we have a new friend with us here today, Kelly Ann Winget, CEO of Alternative Wealth Partners, a private equity firm focused exclusively on alternative assets. So I’m sure we’re going to talk a little bit about what that means. We’re going to talk about all kinds of fun things. But first things first, Hey, Kelly Ann, welcome to the show.


Kelly Ann Winget  0:57

Thank you for having me, Laura. And I’m so excited for this.


Lauren Conaway  0:57

I don’t mean to, and I just want to tell you, I know that y’all might not be able to see this, but Kelly just threw up her hands. And I’m a very excited gesture, which means I can already tell that this is going to be a good one. So, let’s go ahead and kick it off. And I’m gonna ask the perennial question, Kelly Ann, tell us about your journey.


Kelly Ann Winget  1:18

Well, it’s been an interesting one. And I don’t have a traditional finance background. So, you know, the fact that I’m in private equity in general is strange. And then the way that I take it on the head at first in a different and innovative way. home, and I was fortunate enough to have two parents that were in financial services. So it wasn’t like a foreign topic at the table talk. And I’m five generations in oil and gas. So I was going to end up here one way or another. So, but my first my first business was actually selling golf balls back to golfers in my backyard.


Lauren Conaway  2:05

Did you go and, like, find them on the golf course or in the pond and, like, gather them up and then sell them back?


Kelly Ann Winget  2:11

No, we, I lived off the hole, and there weren’t very many good golfers at our country club. So they, I got free access to golf balls in our backyard. And their choice was either to give me $1 for it back, or it had to come into the yard with my giant black Rottweiler. So there, it was an easy choice for them to make. And that was my summer job, which was making dollars off of golf balls. But


Lauren Conaway  2:37

That’s crazy. So, really quickly, I just want to let you know that one of our podcast co-founders, Matt DeCoursey. Like, that’s actually his entrepreneurial origin story as well, like you’re telling us? Yeah, I feel, I feel like y’all need to meet because you have a lot in common here. But that’s so you’ve been entrepreneurial from a very young age. Yeah, clearly.


Kelly Ann Winget  2:59

And I’ve always like, wanted to do things my way. And even though I came from an affluent upbringing, it was very much understood that my parents money was their money. And, you know, if we wanted things, we had to go out and figure it out ourselves. And so, me being a bratty teenager wanting expensive pairs of jeans from Hollister, this is 2004. Okay. And, you know, so the bedazzled jeans from buckle or whatever. And my parents,


Lauren Conaway  3:32

by the way, just saying the same, but yeah, exactly.


Speaker 2  3:37

So, you know, I went out and I went out the back door, and I went down the street and I got a job at a carwash. And the only thing that they would let a 15-year-old girl do is run the register because women are terrible with money. So let’s give them the job to handle cash. The I was there for maybe a few months before I started out selling the service advisors outside. So they moved me into sales. So I’m like 16, and then 17 years old, making almost six figures part-time in high school selling car washes. So that was kind of my first taste of making a lot of money and understanding that there’s a connection between a customer’s need and the way to provide a service that no one else can. And I had exposure in a lot of different types of industries. When I graduated high school, I went into healthcare work for radiology firm, and then into construction working for a demolition company. And that’s kind of where I learned a lot of tangible skills as far as like software or, you know, building on databases, understanding data, and information in general, which helped me kind of leapfrog into the private investment space and that was through oil and gas. And I found my way there organically, just through a plethora of love, life, experiences between the time I was 18 to 21. Wow. So it was just it


Lauren Conaway  5:08

Sounds like one of the things that I find really interesting is like the through line of many, many entrepreneurial experiences that I know of is the fact that like, we were all kind of job hoppers, and we all kind of tried different things. And I really think that that was fantastic preparation for being an entrepreneur. Because the fact is, like in our roles, often you’re one of few, or sometimes you’re the only one doing the deal. And so you’d have to kind of do it all. And you have to have a very multi very dynamic perspective of business and what it can look like, do you think that your past experiences kind of Alcudia into the entrepreneurial space? Oh, yeah,


Kelly Ann Winget  5:49

I mean, a lot. A big part of that is being able to understand like a wide variety of personalities, when you work for 60 radiologists, which, if anyone in your audience is familiar with doctors are like that are the weirdest doctors, because they sit in these like bat caves and hospitals like staring at screens all day. And they have to know everything about everything. So they’re an interesting group to work with, and then flip flopping into construction, which is a completely different type of personality. So being Yeah, has been really helpful, especially now when I’m dealing with a wide variety of different types of founders or different types of investors, because those personalities understanding them and being able to process information with them differently. conversation to conversation is a really valuable skill.


Lauren Conaway  6:49

Yeah, for sure. Well, so I want to talk to you a little bit about alternative investment. Because we talk a lot about angel investment, venture capital investment, we talk about bootstrapping, in. So I think our listeners at this point know, there are a lot of different ways to fund your startup to fund your business. But I’m going to ask you to do me a favor and explain it to me like I’m five. Talk to you what is alternative investment.


Kelly Ann Winget  7:17

So alternatives in general, as far as an investment, like type is everything outside of traditional asset classes. So anything outside of stocks, bonds, and cash is considered alternatives. And this could be a real estate rental property, this could be crypto, this could be a venture capital investment, this could be private equity, this could be a note, it could be also different types of different things. And as long as it doesn’t fall into the category of a publicly traded stock, a bond or or just sitting on cash, is considered alternatives. Now, Alternative Wealth Partners focuses in private equity as a sector. And when it comes to the founder in the audience, and everything like that is that private equity is kind of the big umbrella of what the investment is. And then there’s different levels of capital and focus points of private equity. There’s venture capital, there’s growth, and then there’s like a leveraged buyout, majority stake kind of thing. And the way that we build out our portfolios is really blended across all three of those so that we invest in everything from a venture level investment to a buyout, and then across multiple different types of industries. And so being a part of the venture capital world, and dealing with different types of founders, there are companies that are spending a lot of time and effort trying to raise capital from VC, when they should be really focused on either establishing a better relationship with a better bank, or finding a private equity or private investor who who can focus on the growth part of their business because they might be beyond venture or not make sense for that type of capital.


Lauren Conaway  9:03

Okay, can you can you dig into that a little bit more deeply? Like, what are some reasons that maybe VC investment might not work for a founder, but alternative investment would? Can you give us maybe maybe even give us like some scenarios or something like that to give us some context.


Kelly Ann Winget  9:20

So there’s a lot of risk and VC and a lot of those venture capital investors are looking for early access to big opportunity. They invest with the, with the idea that they’re going to 10, 20, 50, 100x their investment. And they take significantly large pieces of the business. And kind of I call them a little bit predatory. Because there are businesses, especially with female founders, that I’ve learned that they’ve been able to bootstrap their business way beyond something that like a venture capital is going to come in or an angel invester, were there already generating over a million dollars in revenue. And so somebody coming in and saying, oh, I want to be an angel investor, oh, we’re looking for pre-seed or seed funding, when they don’t really need that. What they need is an advisor, or an a single or a couple of investors who really understand how to get them in a position that maybe bank financing makes more sense because they have a viable business. Or go ahead and find private equity that is focused on growth, capital, maybe not a majority buy out, but maybe a minority partner. And I think you’re seeing a lot of this kind of shift around as venture capitals kind of got an interesting reputation right now. And there’s a lot of these like private equity debt funds out there that are that are being spun up to help companies with growth capital because they’re no longer able to get that support from banks. I think that if you listen to any of my other, like interviews in the world, is that I kind of throw banks under the bus. Because you have such high rates, and banks don’t take that kind of risk to to, like justify a 10% interest. And their


Lauren Conaway  11:07

opinions like to give money to people who already have money to give money. To a certain extent, I kind of understand like it is a bank’s job to mitigate risk for their shareholders and like, I get it, but at the same time, I also I speak to so many founders who are like, you know, I got told by the bank, or I got told by the VC, let us know when you’re further along. And it’s one of those things where it’s like, there’s a bit of cognitive dissonance there because you’re not going to get further along unless you’re well capitalized, and you’re not going to be well capitalized by traditional manager, right? You’re further along, and it’s like this, it’s this cyclical failure cycle that you’re going to have. And so it’s your job to help founders and entrepreneurs overcome that. Right, right. You’re the the sticking point in that cycle, like how do we get assets, get investment, get money into the hands of founders who need it, who might not be able to rely on traditional banking institutions, right, right.


Kelly Ann Winget  12:12

It’s definitely a conversation of like the chicken or the egg and the cart before the horse and all that sort of thing. And I think that founders today are getting more nimble with how they bootstrap their business up to a certain point. And I have a lot of opinions about, you know, the number of companies that are going to stay private, over going public, and the kind of skip ahead to private equity, that’s going to start happening. And it’s because it’s removed, like the banks have removed themselves from the competition. So it really is the private investor who’s going to be able to use their money in and outside of the bank, to fund and get access to opportunities that they’ve never had before. As the traditional way of financing, these really big opportunities is gone. So it really is up to the private investor to decide, okay, I can put my money in the bank for 5%. And hopefully, the bank will be able to lend the money out at eight to 10%, in order to cover their spread. Or I can take my money out of the bank with the same level of risk and put it into the pump the private market and make my own 12 to 15%. So it’s an interesting thing to see shift. And I think that founders should really focus on finding investors that align with what they’re doing because there’s a lot of people out there. And then for the investors perspective is like, you can actually make a lot of you can have a lot of impact by using your own money to make these investment decisions outside of just like, well, you know, my advisor says Plan A is best for me.


Yeah. Well, in say one of the things you’ve alluded to this a couple of different times, and I see that it was something that came up on on the setlist that I’m looking at right now. So you, Alternative Wealth Partners, you have a focus on the oil and gas industry. Can you talk to us a little bit about that? What mean, what that means for you organizationally, like maybe why what niche what, what gap are you looking to fill with AWB?


Sure, so we do have a specific fund dedicated to oil and gas. But a majority of our products that we build out is focused on diversification. So I obviously have five generations that oil and gas and it’s something that I’ll always be invested in. But there really needs to be an investor that has both sides of the picture in mind, which is we have to have a sustainable path to transition to renewables. And you can’t do that when oil is at $90 a barrel and you can’t get oil down from $90 a barrel unless you make investment into that space to make it cheaper and more efficient. And so when you have cheaper oil or efficient industry that you then can afford to build out the infrastructure that you need in place in order to move into the renewable space, and you have to invest in both. And so, you know, that’s how we’re invested in both the traditional asset class of oil and gas. There’s a lot of incentives there. But using the returns, this has created generational wealth since the beginning of time. You know, my family has wells and our family that still paying out royalty checks almost 100 years later. So you’re talking about a generational asset that can provide the type of return that can self-fund transition. And the difference between how we do it and everybody else is that I’m focused on changing the invest in what the investor looks like. Because if everyone just keeps looking like me and is invested in oil and gas, then it’s going to just stay in oil and gas. But if I can make another woman or another minority, generational wealth from oil and gas, they are then going to be able to take that money, and invest it in something that matters to them in their community. Yeah, away from oil and gas. That stays in the same. Very whitewashed investor base.


Lauren Conaway  16:27

Yeah, well, and I do just want to note, either one of the things that you said that really resonates with me is the fact that we know for a fact the data shows us time and time again, that when women and minorities, and incidentally, this is my little soapbox, so feel free to disregard but I hate that phrase because it verbally excludes the possibility that women can also be minorities. But that being said, I’m gonna go ahead and use it for lack of anything better. So women and minorities, we know that statistically speaking, they reinvest back into their communities at higher rates than their white-male, cisgender counterparts. We know this with 100% certainty. So when you set up a family led by a woman or led by a person of color, or or led by any other kind of intersectional identity, we know for a fact that they’re those individuals are going to be more likely to support their insular close community, like that community. So for instance, the Kansas City community versus the global community. And then so wealth begets wealth, right? Like you’re you’re you’re putting wealth in the hands that are then using that money to create wealth amongst those nearest and dearest to them. So love that. I’m really, I’m really curious, though, about this oil and gas thing, you said something really, really fascinating to me, and I want to drill down on it. Understand, you said, and I’m trying to remember exactly how you said it. But you said understanding that renewable energy is the path forward, you know, so you’re investing in the oil and gas space, but you have in the back of your mind, like there’s an expiration date here. Yes. Hopefully, someday, we will no longer be dependent on oil and gas. And so can you talk to us a little bit how that manifests that that knowledge that, you know, there’s, there’s gonna be an end here? How does that manifest itself in your work and the investments that you make and in the work that you do?


Kelly Ann Winget  18:26

Well, we leveraged the tax advantages of oil and gas investing in the returns in order to finance projects, infrastructure, or technology that supports the renewable future. And it’s not that we won’t need oil and gas ever again, at some point in the future, we think we will always have to do that. But there’s so much innovation happening in technology, and not enough in the infrastructure and hardware around it, to support it. So you know, that’s where we’re focused on. I’m really, like, very bullish on the industrial space, and infrastructure and manufacturing. And not that I don’t like tech, I just think that it’s so well funded. And without bumpers that, you know, they can advance all they want, like take AI for example, you know, everyone in their mothers and coming up with a new AI product. The problem is that they are going to run out of computing power, not only from the hardware perspective, but also the cloud space and and the energy needed to power that. And if you don’t focus on creating the power structure to support technology’s growth, then it all implodes and none of it matters anyways, so that’s why I like the space so much is because you power electricity is makes everything possible.


Lauren Conaway  20:05

Yeah. Well, so I want to speaking of things that make everything possible, one of the things that we talk about around Startup Hustle a lot is the fact that you need to put a strong team around you. And I gotta tell you, friends, you know, one of the things that we talk about a lot is there’s software developers. There is there’s a dearth of tech talent out there. But finding experts, software developers doesn’t have to be difficult, especially when you visit full scale.io where you can build a software team quickly and affordably. Use the Full Scale platform to define your technical needs, and then see what available developers testers and leaders are ready to join your team. Visit FullScale.io or look in the show notes and click the link to learn more. Friends, we are here today with Kelly Ann Winget of Alternative Wealth Partners, a private equity firm focused exclusively on alternative assets. Alright, so Kelly Ann, we have been talking, well, we’ve been talking about Alternative Wealth Partners, and we’ve been talking about the oil and gas space. But now I kind of want to open things up a little bit. And I want to talk to the founders that are out there listening, you know, maybe AWP is not ready to invest in the the average founder who’s listening to Startup Hustle, maybe they don’t fit your niche. But that being said, what are some words of wisdom that you might have for founders looking for alternative capital assets? Alternative capital investment who are trying to maybe they aren’t ready for the banking institution? Maybe they are, but they don’t want to? Maybe, you know, maybe they don’t want to seek venture capital investment? What are what are some things that founders like that should do to make themselves more attractive to groups like AWP?


Kelly Ann Winget  21:51

I think that I’m going to give a little bit of a contrarian perspective, because I think there’s a lot of coaches and a lot of like consultants out there that are like really heavily focused on like, making your pitch deck deck perfect, and you’re making your pitch perfect. And the reality is, is that when you’re especially for early-stage businesses, more focus should be spent on building your community because that’s where your first check is going to come from. So it’s either a friend, a family or someone in that community. And, you know, I focused a lot when I launched Alternative Wealth Partners, not on marketing, materials, not on not on like advertising, alternative wealth partners, I spent a lot of time and energy and money on PR because I needed to establish myself from behind the curtain, right where I had existed for few years. And be like, I’m actually the brains behind this crazy thing that’s been going on. And here I am as a thought leader. And so I’m building my community around, like who I am as a manager, and who I am as a as an investor. And I feel like founders lose their story because they’re so focused on this perfect pitch. You’re going to have to have 9000 Different perfect pitches when you’re raising capital, or starting your business. Because you’re you’re going to be dealing with all these different personality types as far as your investors go, whether it’s an individual or family or family member, or whether you’re going to an institutional investor, like a VC, a venture capital firm, or private equity, or whatever. But you really just need to focus on your story, who you are, and who you are creating something for. Because really defining your community and building that out is going to be the the most impactful thing you can do for your business. Because not only does it create customers, but it creates support not only financially but just like organically out in the world. And so I think that’s my biggest piece of advice is like really focus on establishing who your community is, and less time trying to perfect a pitch deck because no one cares. I look at pitch decks for like two seconds. i Yeah, it doesn’t. These groups that spend six months going through due diligence on financials and stuff. I don’t know how long you can spend six months on financials for a company that’s been around for two seconds. You know, so it’s, it’s a forecasted picture of best case scenario. And the only time you should be spending on a best case scenario, financial picture is with the person who you believe is going to be making that true. And if you don’t believe in the founder, the founder can’t make you believe that it doesn’t matter what numbers that person puts on paper. If you believe in that person, and that person believes that they can make those numbers true. That’s what you’re investing in when talking about early-stage startups.


Lauren Conaway  24:59

and We’ve We’ve heard that time and time again, it’s so interesting to me because there there seems to be a little bit. Again, that cognitive dissonance that we find like we we put placed so much emphasis on, like, let’s create these really slick materials, let’s make sure that we have everything packaged up so beautifully. When in reality, we also know that investors tend to make very split second gut decisions about investment. You can throw all the numbers in the world up there on your pitch deck. But if they don’t like you, or trust, the founder, you’re not getting their money. In so in what you’re talking about with this community building thing, and I love that your your cornerstone of care seems to be that relationship building piece. But one of the things that we know for a fact is when you engage the community around you, you create brand advocates. And that’s what you’re talking about. You’re talking about brand advocacy. Yes. You’re talking about creating people who will then do your work for you exactly. In broadcasting your message to the world to the community to you know, the invested parties. That I mean, that’s what you’re talking about, right?


Kelly Ann Winget  26:11

Definitely what I’m talking about. And I mean, I wrote a book about this, and what call it’s where can we find this? places you can buy books, it’s, it’s called Pitch the Bitch. Yeah, grab it, Grab Your Financial Future By the Bags. And it’s specifically like anybody can read it. But it’s really focused on those that have been left out of the wealth, conversation, women, and the disenfranchised, right. So it’s really about changing the mindset, recognizing that there’s a pattern in the messaging that is that we don’t deserve access, that you don’t know what you’re doing here, money, let other people make these decisions for you. And so the book walks through, here’s the messaging that you’re hearing. And here’s how to recognize that those gatekeeping the the gatekeeping phrases, and how to start making these decisions yourself and educating yourself on money in general, it’s not about like, what you should be investing in, I don’t care what you’re investing in. But I want you to care about it for yourself, I want you to start making those decisions for yourself, on behalf of yourself and the things that you think are important. So I mean, that whole thing is connecting with anyone, I can only work with accredited investors. I can only work with people that have million plus net worse. But that doesn’t mean that I’m not going to talk to somebody who doesn’t have a million dollars. Right? It’s all about access. So the way that I’ve created the brand identity and writing the book, I wrote the book so that people could have the information for free. I don’t want to gatekeeper what the wealthy family offices are doing. It’s a system that can be implemented, whether you have $1 or a billion dollars. It’s just a mindset strategy. In setting yourself up correctly, to have generational wealth for yourself, and generational wealth means different things to different people, somebody having $100,000 in the bank, could be generational wealth for them. Whereas some other people might need $10 million in the bank to have generational wealth. Right?


Lauren Conaway  28:26

It just kind of depends on socio-economic circumstances. Are you historically excluded as a as a founder and investor? Is it really quickly I do just I just want to say this, because I’ve been like I’ve been waiting to see this. So I love the name of your book. Yes. And I do have to share with you a bit once upon a time. So we have that my organization InnovateHer KC, we have a startup founder pitch competition for women plus founders. And we call it Girls Just Want to Have Fun doing. But that being said, when we first came up with the idea, and we’ve done it three or four times now, when we first came up with the idea, our proposed name was Bitches with Pitches. But then we had ways who already found way too many potential sponsors be like, ah, can’t Sorry. So we were like, Alright, fine. But that being said, you know, when I saw your books, I just started laughing. I was like, Oh, we’re on the same page. Yeah, excellent. Yeah.


Kelly Ann Winget  29:25

But I don’t really care about whether or not you’re going to sponsor me. Already published the book.


Lauren Conaway  29:29

So, what well, I one of these days, we’re gonna do it. We actually had somebody sneak it into a naming contest. And I was like, hey, hey, all right. It’s still it’s still hanging around the community. They still want it. So one of these days we’re going to name something Bitches with Pitches and it’s going to be like one of the greatest moments of my life. Yes. But But all right, sorry, just wanted to say that. But kudos to you on your name and capabilities. Excellent work. But then the other thing that I Want to ask, you know, you are a little bit unique within the investment space. And we’ve been talking about those who have been historically excluded those who have been marginalized. And usually when we say that word, we are talking about women and minorities, and any kind of, you know, people who are disabled people who are immigrants, or anybody who is not the, I guess, archetypal, archetypal founder, which tends to be white cisgender. Male, you are very few of those things. And I’m wondering if you can talk to us about that, because you are a first and I love first. Yes,


Kelly Ann Winget  30:38

I am the first millennial solo female founded, openly LGBTQ private equity person.


Lauren Conaway  30:50

The first thing is first. Yeah. That’s, that’s like the entire audience cheering for you. Yay. I’m speaking for everybody. Congratulations, hashtag representation matters. But talk t us? Can you talk to us a little bit about that experience? Has it been? Has it been difficult? Has it been fairly innocuous? You know, what has that been like?


Kelly Ann Winget  31:12

So I’ve had the privilege to not deal with a lot of pushback on my identity growing up. But I did deal with it professionally. I never really talked about being gay, in the professional setting, until I met my now wife. So and that could have a lot to do with like, maybe I didn’t feel comfortable enough introducing somebody, but we deal with that as queer people professionally, that the stigma behind like bringing a different person to the holiday, you know, the office holiday party every year, is looked at differently than, you know, our cisgendered male counterparts who might have a different girlfriend every year is different for us. You know, if people are paying more attention to it, I think and it’s the same just for women bringing a different, you know, boyfriend around. Yeah, on a on a regular basis. And so those were things I just never wanted to deal with, especially since I was working in very, like conservative male dominated spaces like construction, finance, oil and gas. So, you know, it wasn’t something that was talked about, because in these investor meetings, you know, things are things are said that you’re like, Oh, you probably shouldn’t talk about that part of my life in this room. Yeah. And it wasn’t until I decided to go out on my own, that it was kind of like a big moment of, you know, what, if people have a problem with it, they don’t have to work with me. And so the power of being able to tell those people, no, you know, like, I don’t actually have to put up with this from you, is really empowering. And it was something that, you know, I really struggled with for a long time. So, you know, just in the last three to five years that I’ve been, like, really comfortable saying, like, This is who I am now that I hit it in my personal life. I just didn’t talk about it professionally. And so now, because I am the face of my own thing, and not representing other people. Yeah, you know, I can be authentically who I am and who I’ve been this whole time.


Lauren Conaway  33:37

Oh, my God, I love that so much. So just a full disclosure for our audience and for your Kelly Ann. I also identify as queer I am hit presenting, I married a dude. But you know, that’s just who I happen to fall in love with and marry. But that being said, it doesn’t make me any less queer. And so it’s one of the eight and it is one of those things where it’s like, it’s kind of your lens a little bit, and I’ll give you an example. So like, yesterday, I was making a graphic for an event that we have coming up for InnovateHer KC, and I was looking for women playing pool. So I put that into the little picture stock photography thing. And so there were a few things that I noticed. First of all, there aren’t that many pictures out there of women playing pool, which is a major bummer. But the other thing that I noticed is that a lot of the pictures had women but it also included men and in a lot of the pictures, the men were teaching the women how to play pool and they were doing it in that like couple the way where I’m gonna put my arm around you and get my breath in your ear and get real close. And I’m sitting here and I’m like, first things first. Why do we not have same sex couples doing that? We could say Hey, ladies do that to other ladies too. And that’s kind of that was kind of the image or the graphic that I was looking for it I was just really frustrated that I cannot find this. It was all a bunch of guys teaching women how to play pool and I’m like You know, I bet I could probably kick the ass of, I don’t know, 60% of the dudes who come my way and try to play me in pool and we just don’t see that pictorially represent No, really, the


Kelly Ann Winget  35:11

stock photo thing is really, it’s an interesting topic, you should have a whole podcast on this because there’s a there’s a female founders team. It’s two black women who have who have launched a whiskey brand. And they, you know, are trying to go through all their marketing stuff. And they’re like, you know, we’re trying to find pictures of women drinking whiskey because women actually really like whiskey. And, and so they’re like trying to find all these photos. And they cannot for the life of them find any photos of like women, or or black women drinking whiskey. They get wine glasses or whatever, but no whiskey.


Lauren Conaway  35:57

There are actually specific photo repositories that have been built specifically for people of color wearable is built, they’re not as robust. Like most of the stock photography sites, like the ones that kind of feature like the cisgender, heteronormative relationships and men, those stock photography, like they have had years to build up 1000s and 1000s and 1000s of images, you would think that with that many images, it would be easier to find what you’re looking for, but it’s not. So yeah, a lot of these repositories like they’re just really anemic or not great. But I think the larger point for our listeners that I was trying to bring home is the fact that like, what you’re talking about with your own experience, you’re talking about the privilege, or or lack thereof, previously, you did not have the privilege to be who you were and to love who you want to love. And then now, as a founder, I actually I enjoy the same thing. Like there’s nobody to tell me that I can’t say can’t say gay can’t say like, whatever word or whatever concept I want to talk about, there’s nobody there imposing values on me that do not belong to me. And therefore I can say what I want. That’s a lot of privilege. Right? Not everybody has that same privilege. And so I think that it then becomes incumbent on you, and it becomes incumbent on me to to use that privilege as possible. You know, it’s one of the reasons I do Startup Hustle, okay, I get to talk about these issues and make sure that people understand. They’re very real issues, and they’re very important, and they affect you just as much as they affect me. Yes. Is that kind of how you feel about it?


Kelly Ann Winget  37:36

Oh, yeah. And I mean, I get to do this kind of across the aisle investing style, because like, I’m a, I’m a queer woman, I don’t hide that. But my investor base is pretty diverse in the fact that we have, you know, a perfect a black professional woman, and a very conservative white farmer, invested into my fund, which I then invest in things like oil and gas, but also like, one of our portfolio companies is Dapper Boy, which is a gender neutral clothing companies founded by a queer couple, right? And so when they were when they were fundraising, it was this goes back to the community piece is finding an investor who understands, right. And I’ve been watching Dapper Boy’s story since they started right as an individual investor, but now having the opportunity to do it from the institutional lens, going into that company and being like, Well, I understand because I’m this person with this problem. And I am not a niche, right, this is the feedback they’re getting from investors is that they’re too niche. They’re too niche to have a gender neutral clothing company, which is just clothes that fit everybody is not niche, and especially when you have Gen Z and millennials who more than half of them identify as some sort of queer, right? And so they’re looking for an androgynous style clothing company like that is the lifestyle brand that they build out. And it is, and it works for both men and women and non-binary. And that’s the point. And men and women and non-binary include 100% of the population. So I get to that’s what everybody felt, right? That’s how many folks and so having having that representation for them, for me as an investor, right, being open that way, we can have an authentic conversation about what their mission is and the conversations that they’re having with their customers. Right? There are these life changing feedback from the people that are buying their clothes, and me being able to see that and be like, I see the value and getting other investors on board with me.


Lauren Conaway  39:42

Yeah, well, and I love that they again, I’m going to share a little bit of my personal journey like I have always identified as female, but I also I tend to dress more gender neutral, androgynous and that’s a personal choice that I make. I have many reasons but even like I’m looking at the Dapper Boy website right now, like full disclosure, I am paying attention to the conversation. But I got really interested. It’s


Kelly Ann Winget  40:08

so they’re soft. Their shirts are so soft.


Lauren Conaway  40:12

like, I want to buy these clothes and they weren’t, they weren’t they were built for me, but they were built for everyone. And so like that, and that’s that right there that said, That’s design thinking when you engage in Design Thinking you and you design for the most vulnerable, knowing that it will benefit all. Exactly.


Kelly Ann Winget  40:29

Yeah. Yes. Yeah, that


Lauren Conaway  40:33

was super cool. And I love that you are using your privilege, such as it is. And you’re using your privilege to help give voice and give a platform and give support, i.e., money to your organizations, and found that yes, it needed that. That is really, really cool. Congratulations. Now, we have come up with the human question. Are you ready? Yes, I did. Yes. So, if you could be a guest on any television. And you know what? I’m going to remove the television word on any talk show because we could do web shows. Which would it be and why?


Kelly Ann Winget  41:13

Kelly Clarkson.


Lauren Conaway  41:15

Wait, do you just do you just dig her? Like, she seems really cool.


Kelly Ann Winget  41:19

Yes. I love Kelly Clarkson. And I’ve manifested it to be so and so. I think that she just has such a, and she’s from, so I live in North Fort Worth. She’s not that far. Burlison is not that far away. So you know, we’re from the same area. And I have a funny story. I was in the post office in my little tiny neighborhood, and some old lady came up to me and she whispered, are you, Kelly Clarkson? I was like, No, I’m not. My hair is up in a ponytail now. But I do have large hair like she does. And I just think that her personality and talk show style are so cool and, like, friendly. I think that that would that’s probably where I want to go.


Lauren Conaway  42:07

All right. Well, I cannot tell you how much I appreciate you coming to the show today. Kelly Ann, it has been it’s been a pleasure chatting with you. Thank you very much for sharing your knowledge. But more importantly, thank you for sharing yourself and your expertise with those founders out there who need alternative investment. That’s the name of the game. Just very, very appreciative of you. And I cannot wait to see what you invest in next. I’m already planning on going on to Dapper Boy and buying.


Kelly Ann Winget  42:38



Lauren Conaway  42:41

But very, very cool to have you on the show. Kelly, thanks for being here.


Kelly Ann Winget  42:44

Thanks for having me, Lauren.


Lauren Conaway  42:46

Absolutely. And hey, friends. One more time, if you need to hire software engineers, testers, or leaders, Full Scale can help. They have the people in the platform to help you build and manage a team of experts. When you visit FullScale.io, all you need to do is answer a few questions and then let the platform match you up with fully vetted, highly experienced software engineers, testers, and leaders. At Full Scale, they specialize in building long-term teams that work only for you. Learn more when you visit FullScale.io, or you can check the show notes for the link. Alright, friends, I am going to ask you. I’m going to put out a call, I’m going to ask you to do what we always ask you to do. But it’s really, really important. Startup Hustle is a show that is by founders; for founders, we do this work for you. We also do this work because it’s super fun. And it, you know, breaks up the monotony of a Wednesday. But that being said, we really, really do this for you. And we want to hear your feedback. We want to know, as founders, what do you struggle with? What topics do you want to hear us talk about? What founders do you want us to interview? What companies are on the rise? What do you find interesting? We are here for all of it, and you can find us at StartupHustle.xyz or check down in the show notes. We are also on Facebook, we’ve got a chat group, and we have a LinkedIn page where you can reach out to us. There is a wealth of opportunities to reach out to Startup Hustle, and you can start it with a Google search and just find us. Let us know what you want to hear. We are here for it, and we are here to create a show for you. As always, we are very grateful that you came and you listened to us week after week. We hope that you continue to do so, and we will catch you next time.