Heather Wentler – One Plus One Equals Three | Conversations with Coaches | Boxer Media

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Heather Wentler | Conversations with Coaches | Boxer Media

Heather is an advocate for entrepreneurs who identify as women and historically marginalized gender/s; believing they are strong, independent individuals capable of success. Professionally trained as an educator, she co-founded the Doyenne Group, which brings a holistic approach to supporting the entrepreneurial journey & ecosystem.

In our absolutely delightful conversation, Heather shares her early beginnings as a teacher/mom/big-sis in her family, and how that led to her teaching middle school for years. Then, we discuss how she found herself coaching as the best way for her to have the kind of impact in the world that she really wanted to. We also dive into the importance of diversity in the entrepreneurial journey, the absolutely vital importance of “fit” when it comes to who you can best serve, and all of the different programs that Doyenne Group has to offer people at various stages of their development. 

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Kevin Stafford 0:00
Hello everyone and welcome to another episode of the conversations with coaches podcast. I’m your host Kevin and you might be able to tell I usually have some delight in my voice when I when I intro the podcast I have that usual delight here. It’s a little extra special because I got to have some laughs and, and some and some and some hearty, almost borderline cries talking about the state of the world in 2023 and how our families trafficking but anyway, let me introduce you to Heather Wendler. I’m already delighted to meet her and so let me introduce her to you. Heather is an advocate for entrepreneurs who identify as women and historically marginalized genders believing they are strong, independent individuals fully capable of success. professionally trained as an educator. She co founded the doyen group Am I pronouncing that right? doyenne? Excellent, which brings a holistic approach to supporting the entrepreneurial journey and the ecosystem that surrounds it. Heather, like I said, it’s a delight to meet you. I know I already said that you have an excellent energy. I feel like we’re already like pod friends. And so I’m excited to talk to you about about your passions, but what you’re doing in the world today. So

Heather Wentler 1:01
yeah, thank you so much for having me. I’m excited to talk to you as well.

Kevin Stafford 1:06
Awesome. Well, let’s go back. Let’s go back to the beginning. At the very beginning, we don’t need we don’t need that whole story. But I mean, unless it goes back that far, how did you? And I’d like to kind of put this almost cheekily, how did you get your superpowers? How did you how did you get your your origin as a coach? Did you have like a key mentor at the right time that kind of came in and like maybe gave you the right words to describe yourself or a certain opportunity or a desire just blossomed within yourself to shift? And then coaching was the answer to the kind of impact you want to have? How did you how did you get that start? How did you get that discovery about yourself?

Heather Wentler 1:39
I mean, I think it does kind of go back to my childhood. So I am the oldest on both sides of my family. And so plain as the there was a lot of like, being the mom, you know, the quote, unquote, Mom role for siblings, I have a sister, and then all my cousins. And I think that was part of it. But then the other thing, you know, when we would gather and hang out and play, we would play school, and I would always be the teacher. And I’d be like, it’s recess time, and I’m going to make worksheets for you. And I loved it. And like, that’s what propelled me to want to become a teacher and educator. And that’s what I was professionally trained how to do. So that’s what my degree is in. And what I noticed when I was teaching is I would be able to connect with my students. I taught middle school, which as you know, is the worst three or four years of your life.

Kevin Stafford 2:29
But kind of the best to teach. There’s all there. Yeah,

Heather Wentler 2:33
there’s so much fun, we could do a whole nother episode. But, you know, like that was, that’s where I resonated the most, because they’re in their mind that we’re trying to create all of these synergies between what’s happening in their lives to how does it apply to the curriculum that we’re using at school. That’s where I had to break from school. So that, you know, they wanted you to figure out how to divide up cantaloupes into equal numbers of pieces and stupid stuff like that. I did not understand. And my, my students were just like, what, so that’s where becoming an entrepreneur, my husband’s also an entrepreneur, so he had already kind of planted that seed in me as well. And then my co founder from Julia and I met her at an event here in Madison, Wisconsin, where we’re headquartered. And she was really like she was that coach, and my big sister, and a lot of ways that I needed. And that’s why we found a Doyon. And I did not think I would become a coach that was, you know, not something that was I ever thought was in my life journey, but love the work that I do. And I love hearing all the stories from people.

Kevin Stafford 3:48
Yeah, that’s interesting that that someone who became your partner, sort of in an interesting way ended up filling a similar role that you filled to everyone in your life when you got your start. And so you had that both that connection, but also that ability to have someone provide that for you even as you provided for them. That’s, I mean, that that feels like the like the secret sauce to a great partnership, doesn’t it?

Heather Wentler 4:08
Each other crazy, which was also great, because my, my like spreadsheet introvert totally would align with her like, very extrovert, I just kind of flow through life energy. So while we would drive each other crazy, we also knew that that was our superpower that we could complement each other so well. And that’s what resonated so much with the entrepreneurs that we were that we serve as well because they knew when to come to me and they knew when to come together for the different things that they were looking for in their businesses.

Kevin Stafford 4:46
That’s so lovely. I like in my head immediate like as you were talking and describing the relationship, it’s just one plus one equals three just like went on like a billboard behind my bike like in the back of my forehead and I was like, that’s exactly what this is. And that’s what a great partnership is like. And that’s I mean, it’s also what great coaching is like, where you really feel like that what you’re able to accomplish and discover together is more than you could find separately, even if you added them together, it’s just there’s a, again, that word comes up a lot, and animals hate using it. But that word synergy, it just keeps being relevant to relationships like this, and connections like this, and growth like this. And I just, I love that you found it in your partnership. And that represents, I imagine what you offer, to the people that you coach is that kind of one plus one equals three, synergy.

Heather Wentler 5:25
Yeah. And that’s where, you know, a lot of the theory behind Diane, for the programming and the coaching that we offer, it’s all Amy also was an educator, she taught entrepreneurship at a local university. And I should mention, because I’m using past tense of Amy, now, Amy did pass away at the end of 2018. So she was in an accident while on a family vacation. And so, you know, again, a whole nother story. But you know, like, the eight years we were together, that’s what we, how we built the organization, how we build all the programming that we do, and we continue to do and fill and trying to fill that gap of her not within the organization, but always going back to both of us are educators first. And so knowing how to take these very high level ideas, and how do we relate them back to what’s been, you know, the personal experience that the entrepreneur is going through? And what’s the pain point that they’re feeling right now? And so how can in relating it back, because, you know, I still, I still believe that even though they say the me mind, is only when you’re in middle school, while you know, like all those hormones are raging and your brains continuing to fully grow and function, we never actually grow out of it.

Kevin Stafford 6:43
I certainly haven’t.

Heather Wentler 6:45
Make it about me, I’m gonna care more about it. And so that’s really how our approaches and we take them seriously. And we listen and we validate. And that’s I think what a lot of entrepreneurs are feeling as missing when they’re out in the real world, or they’re so bombarded with nose or this is why you suck, that coming into doing and just feels like a total different experience where you are seen and heard until, yes, that did happen to you. And how can we support you through that and move forward or let that stuff go? I didn’t

Kevin Stafford 7:20
let that go. Yeah, and permission and the reasons why like, it’s not just, it’s not just, it’s not just apathy, which can be a very tempting shortcut to get by stuff like that, or dismissal or deflection. And it’s also not overly internal internalizing stuff, because, like you were saying, it’s such a, there’s so much negativity kind of just bombarding you on a regular basis. So many knows or not now, or this didn’t work outs, and all the things in between that, that as an entrepreneur, you’re pretty much the tip of the spear, and kind of most of the rest of the spear as well, at least you’re starting out. And there’s just so much that needs help to be processed. And I feel like a lot of entrepreneurs, when they get to that certain point where they’re like, You know what I do, I need help not just to grow the business, I don’t just need to build a team, but I need to help to build myself up, and to be the best that I can be, so that I can serve the people I want to serve and help you and I want to help and grow the business I want to have. And I love the way you kind of step in and not just give permission, but also sort of aid in the lack of a better term, the digestion, the processing, you know, there’s just like, just needs to pass through me in some way. And I need to know what to make sure it stays out. And then what I let in so that I’m actually growing constructively in building as opposed to just letting the garbage in and keeping the good stuff out. Which sometimes you get so much on your plate, you get, you know, lost in the sauce, and you can’t keep track of what’s what what you shouldn’t be letting in and what you should be keeping out and you are perfectly positioned to help or something like that. It sounds like

Heather Wentler 8:49
I do the best I can you know, as you know, to your point oh, like what’s my superpower? I always say your superpower is also your kryptonite. So sometimes it’s really hard to let it go. So one trick I’ve learned is when people are telling me about stuff, I’m like, so I’m a fixer. Are you telling me this? Because you want me to help you fix it? Or are you telling me because you just need to get it out. And we can talk through it and be able to move on from it. And so kind of, you know, letting the entrepreneur tell me how can I best serve them. But then also, I don’t feel like I have to carry all that on my shoulders as well.

Kevin Stafford 9:25
There’s that, that not shifting of a burden, but more of like an more even distribution of weight so that you’re not like not what not one part or one person’s being crushed by it. It really it creates a kind of space and a kind of extra energy and processing ability to really be able to not just dodge, you know, boulders coming down the mountain, but maybe, you know, break them down and build something with them.

Heather Wentler 9:47
Yeah. And one of our guiding principles is that entrepreneurship happens in a life. So, you know, I’ve had meetings where I’m like, Oh, you brought your kids today. Great. Let’s invite them to the conversation or I brought stuff that they couldn’t do that or, you know, you’re just recognizing like, what’s going on, you’re not seeing you’re not, you know, either coming across or I’m feeling these emotions coming out right now based on the conversation Do we need to take a step back? And a lot of other programs that are similar to what we do, they don’t allow for that. There’s no like, you know, we say life happens, life happens all the time. And there’s no like, I can’t just turn off whatever other identities I’m wearing and only focus on my entrepreneur identity right. Now that that doesn’t happen.

Kevin Stafford 10:38
We’d like to, we’d like, it seems like it would make it easier if it could. But even that’s kind of like a bit of a lie. It’s just there’s, it just seems like it might be too much. And I love that I love the way that you’re like, if your kids are coming to the meeting, come on in, we’ll we’ll involve them. Because as much as you might try to think or try to make it so that your family is not going to be a part of your entrepreneurial journey. They are they are.

Heather Wentler 11:00
And they have to be because your entrepreneurial journey, your venture lives and breathes just like I do, just like you do. It has its own emotions and complexities and personalities as well. Yeah.

Kevin Stafford 11:15
And I love the I love the the word that comes to mind immediately is the invitation. It’s like, it’s all invited, it won’t all get to stay. But it’s all invited in well, we have we’ll have we have many rooms in this in this mansion of your entrepreneurial life. And we’re going to make sure everybody finds the right room, everything finds the right room. And then when it’s time for certain guests to leave certain kinds of, you know, critical feedback, negativity, you know, whatever it happens to be, we’re going to make sure that they find their way out in a timely fashion. I just I love that there’s an inherent at the beginning. There’s always an invitation. I love that. Awesome. Yeah, let’s I think there’s so much I want to talk to you about I love getting into the conceptual stuff, because it naturally leads into the practical and it kind of starts to go back and forth. And I, I could do this all day. But I do want to give you a chance to talk a little bit about what doyang Group looks like today. In the context, in particular of I kind of like to ask this as a two part question cuz I feel like it kind of gets at the heart the nuts and bolts of a practice. Who do you coach? And how do you coach them primarily speaking again, and that’s the who could be like, you know, at what stage in their entrepreneurial journey, you know, it’s different sized businesses, particular industries that you find yourself focusing on or just have a large client base within and the how being, you know, one to one group coaching, masterminds, keynote speaking coursework, you know, books, all of the above, and then some, so like, yeah, who do you coach? And how do you coach them?

Heather Wentler 12:36
Yeah, so the average entrepreneur who comes through Dwyane, you know, is usually late 20s to early 50s. And also like, typically, has had some experience within the professional world. And usually what we uncover is, there was some sort of toxic, something that happened within that workplace structure as to why was the what was the final decision to help them make that leap into entrepreneurship. And not always toxic, but a good amount of time tax. Usually add is, you know, they they’re an emerging or early stage. So our mission statement within the organization said, says that we support early stage scalable ventures. But, you know, you can be pre market and still come to Doyin, we’ve supported ideation stage, we’ve supported, you know, I have a full fledged company that I’ve been running for 30 years, but I have this new product or service line that I would like to expand out in the company, we’ve supported them. So while we’ve technically supported over 21 industries, and we claim we’re industry agnostic, where our sweet spot really is, is the you know, anything except for brick and mortar, like, I don’t have a positive spin to put on that one. But there’s a ton of other services for brick and mortar companies within not just within our community, but with across Wisconsin, which is where we primarily serve. And so we will do a lot of referral back and forth with those other either coaches or organizations as to we can’t help you maybe this is how we can help you but we really think that this is more of that places sweet spot. So you should go over there because that’s another big thing for us is like we should do it should be a tool in your toolbox not the only tool. We want to make sure that you have a network and a community that you can rely on and receive support from not just a one stop shop. So that’s really who we primarily serve. How we do it, sorry. Hello, we do so we have three main areas that we focus on. The first one is really developed the entrepreneurs and that’s where the majority of our programming fits in. So we do one on one coaching. We also have some cohort type programming like our triple threat venture training, which is like a business accelerator esque program, I don’t really like using the word accelerator because we’re not like Tech Stars, we are doing a different approach. And we work with different types of entrepreneurs than someone who would go through a TechStars program, not to say you’re not seeking investment dollars. But, you know, like, different the different approach. And what you’re gonna get out of the program is different than if you went through like, one of those types of programs. We also saw the second pillar that we there’s a lot of other programs that follow that we have, we have online learning lab that we call our Netflix for entrepreneurs that anyone can access whenever and a lot of this stuff, like the vast majority of the stuff on there is free, so anyone can access it when they want it the most. And then the second pillar is really around funding the ventures. And so we do that internally within Doyin. So we have a program called our five by five by five, which has five women owned businesses, each given a five minute pitch one receives a $5,000 grant, we’ve also had an evergreen Fund, which provided grants and equity investments to companies. That is closed right now because all those dollars have been dispersed. And then the third key Oh, and we also have an investor accelerator program that we just launched last year, that’s really for how do you start thinking or understanding what it is like to be an investor and startup businesses, and also introducing those entrepreneurs or those participants to fund managers or entrepreneurs in the community that are looking for investment dollars. So 75% of our people who have gone through that program have made first investments in startups post program, which is pretty exciting. Yeah. And the third main area is, you know, the changing the narrative. So how are we making sure that when you think of the word entrepreneur, you don’t picture a white guy wearing, you know, a hoodie and skinny jeans who coded something in his dorm room.

Kevin Stafford 16:59
Like we’ve got that covered.

Heather Wentler 17:01
That is that is one representation of what entrepreneur looks like. But there’s so many others. And we want to be able to make sure that when you’re thinking about who is an entrepreneur, what does success look like? It doesn’t just look like I made a technology that I built on for three to five years, sold it at a huge, you know, a huge return to my investors, and moved on to the next thing. It says we will get success is defined by the entrepreneur. Seamless scalability is really defined by the entrepreneur as well.

Kevin Stafford 17:35
You, you’re up to a lot. You cover a lot and what you don’t cover you have. And I love that that focus and that investment in fit and alignment, it’s like we might not be the right tool for you right now. But we’re going to know somebody who does and we’re going to put you in contact and when the time comes, where we might be the right fit, we’ll maintain a relationship as such a core value of every good coach I’ve spoken to without fail, is that commitment to being the right fit and finding the right fit, whether it’s you or whether it’s somebody else, or whether it’s now or whether it’s later. And that’s that speaks that speaks well to the work that you’re doing in the world. And ever somebody has to somebody got a chance to interview just out of those earlier this week, I think it was maybe late last week, it all blurs together. But he was he called himself a recovering ad executive, which I love. I love that terminology. And he had had it he had been in an ad agency and he was talking about the problem he had with brainstorming sessions, in the ways is, in particular in creative in a creative set at the ad agency, the way that certain voices would naturally elevate due to the nature of a brainstorm people who were able to quickly express themselves in a loud way to use certain kinds of words to be able to dominate a room or not even dominate but to influence a room. It was a very particular skill set. And so the creative was coming out in a very narrow fashion. And he was like, You know what this isn’t? This isn’t good enough. This isn’t right. There are a lot of people who are just as if not more creative, who can’t get their voices heard in this environment. Let’s, let’s change the location, let’s change the environment, let’s change the way we do things. And that’s he went on to talk about it much more eloquently than I could but I was really it stuck with me obviously. And it reminded me of what the way you were talking about how we just we need to create the space and help people to move into those spaces where their voices can be heard where their entrepreneurial journey can be taken, where it can spread even more opportunity around because yeah, we’ve got we’ve got one representation pretty pretty well covered. understatement of the century, maybe it’s way past time, for there to be a lot more different kinds. And I want to throw the deep word out there but a diversity of experiences. And I know some people carry baggage with that word. I do not or if I do it’s baggage that I want distributed to the world. And I love your commitment to that work.

Heather Wentler 19:51
Thank you. I think diversity, you know, it’s got a bad rap, but I think there’s so many ways we can look at diversity, you know right now, and always should be a high Like, is that racial or ethnicity? Making sure how are we being more inclusive and more open to that, but also, like diversity does come from lived experiences, and also professional experiences, as well as so many other factors. You know, I was recently moderating, for a panel for an event. And one of the questions, it was a bunch of college kids, and one of the questions they asked was like, how do you overcome bias that you’re that you feel as a woman in your field, and I said, no matter who you are, what age you are, what your identity is, you’re going to face bias. And part of it is just reflecting, acknowledging, sometimes sometimes calling it out, if, if you feel comfortable doing that in that situation, or finding allies, supporters that can help call that out. But also, like, just know that, unfortunately, that’s the society that we live in. And we have to figure out how to navigate that, and change that as much as everything else. And there’s so many books I could point to right now on my, my bookshelf, in my office that’s like, here’s work I’ve done around like, how do you build brand culture? Working with entrepreneurs working in professional settings in general, around? How do we create this space? The hardest one is, it’s different for every single one. So that’s like, when we say, We’re safe space, what I say is, we try to be as safe a space as possible, because we’re gonna we’re gonna screw up. And, you know, also what happens when we do screw up? How do we recognize that and try to take steps back and move forward?

Kevin Stafford 21:38
Yeah, it’s an act. It’s an active living process, I often, I think about how it how it’s been working for me individually. And it begins with an understanding of my not just my own biases, but the biases I also face and just really committing to understanding the benefits and the pitfalls, depending on different areas of my life, my environments, things, you know, things that are that basically make it make make the make life beyond easy for me as opposed to difficult mode and things that make things a little bit harder to understand that grapple with that and keep that awareness alive. And then really commit and work hard to expand it out and understand how biases affect the people closest to me, and then start going outward in concentric circles and see it’s like, how are my biases interacting with the ones they’re facing in this collaborative environment on my own team, in my family, in my in my friend circle in my in my in my larger network. And that’s just that is an ongoing process that will inevitably lead to stumbles and pitfalls. And I think it’s important to embrace that because like you said, yeah, that’s it’s a very specific, unique personal identity, what the biases you face your personal experience, how you move through and live in the world. And when you have to respect that kind of uniqueness in common spaces, there’s there are going to be missteps. And I want those upfront, out loud, talked about interacted with growing, changing. So we’re ready for the next one and ready for the next one and ready for the next one on and on and on together as a team and I know I’m starting to get I’m starting to wax a little poetic because I get kind of I’ll get almost romantic about because I feel like it’s it’s like a great human journey together, that we get to all be on that can sometimes be really hard and really painful and really uncomfortable. And like speaking that out there. It’s like if it’s embrace it,

Heather Wentler 23:23
we need to be uncomfortable. Because if you’re comfortable what is that doing for you know, how are we changing things?

Kevin Stafford 23:33
Yeah, comfortable feels closed? Yes. And I don’t want to be closed. Man, I that hosting job, I warned you that I would, I would I would get into the conversation. I’m looking at the Zoom clock, we’ve been chatting for almost 30 minutes.

Heather Wentler 23:46
Oh my gosh,

Kevin Stafford 23:47
I know, I know, I could do this all day, I’m gonna have to have you back. Because like, it was very easy to talk with you about really important stuff very quickly. Like I’ve known you for 30 minutes. And I feel like I can talk to you about some pretty, pretty important and uncomfortable things. And that feels really good. And that speaks that quite frankly speaks right on the right on the target to your coaching. So it listeners out there it’s like this is the real deal. This is what it’s like we can get there and

Heather Wentler 24:13
laugh a lot. Sometimes. brown liquor drinks together like I mean, I will meet you where you’re at let’s

Kevin Stafford 24:23
once I hit stop record, we’ll talk about your your beverage of choice because yes, but before I let you go and before I hit stop record, where can people find out more about you doin group the work you’re doing? And also where can people best connect with you if they want to start a conversation? Start a relationship maybe, you know, learn more and connect. Yeah,

Heather Wentler 24:43
so number one head on over to Diane group.org There’s so much information to the point where I’m always like, I think we’re over communicating on our website, but there’s so much information. Um, there’s a lot of ways you know, sign up for stuff you can get on my coaching calendar. are over there. If you want to reach out and talk to me, please feel free to send me an email, it’s Heather at the door young group.com. Even if you don’t feel like you fit into the identities of women and or historically marginalized gendered entrepreneur, please feel free to reach out. Because you know what, there’s also a lot of ways that non entrepreneurs can support entrepreneurs. And there’s a lot of those opportunities within Diana as well. We have an army of volunteers. And that’s how we get so much stuff. So those are great ways. We are also on Facebook, Instagram, and LinkedIn all at Duang group. I’m personally on LinkedIn as well, for Heather went live. Just I don’t use social media messaging, that’s my big one. So people will get mad at me. So like, I sent you a message a month ago, and I’m like, um, I really suck at this.

Kevin Stafford 25:49
I checked your LinkedIn. No, you say it in your profile. It’s right there. It’s like I don’t I don’t check these messages here too, like trying to like pre warn people. It’s like, I’m not being rude. I just like, you know, I have 24 hours in the day. So please email me.

Heather Wentler 26:02
There’s way too many places I could get messages. And so I would prefer people to email me so that I can and then we can find other ways to communicate. But if you email me, then we can we can figure that out.

Kevin Stafford 26:16
I will be emailing you. I might I won’t direct match to you. But I’ll be emailing you to have you back on in a little while. I loved this conversation. I love I love the work you’re doing. I love the way you’re going about doing it. I love your story too. And I feel like we have much more to talk about but we respect your time and the time of the podcast. So thank you for being with me today. Hey there, it was. Fantastic.

Heather Wentler 26:34
Thank you so much. And thanks everybody for listening.

Kevin Stafford 26:37
Yeah, and hey, we will talk to you again very soon. Do yourself a favor find out more about doing ungroup and Heather in the work they’re doing. You know it’s you know what to do. You know, like, share, subscribe, comment all that podcast jazz and we will talk to you again here very soon.

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