365 Amy Gannon: The Changing Face of Entrepreneurship

When most people think entrepreneur they think young dude in a hoodie eating ramen … somewhere in Silicon Valley … having dropped out of Harvard, MIT or Stanford. The face of entrepreneurship is changing and its about time.


I’m Melinda Wittstock and today on Wings of Inspired Business we meet an inspiring entrepreneur who is dedicated to identifying and unleashing startup talent in places where no one is looking for it.

Amy Gannon is dedicated to bolstering entrepreneurial ecosystems outside of the usual startup capitals – focusing in particular on encouraging women and minorities to start and scale businesses as the co-founder and director of entrepreneurial development for Doyenne.

And if this is something you think you don’t have time for …you probably are exactly the person who needs to make time. Because you’ll get further in those 4 days than you will in 4 months plus we’ll show you how to turn time from a scarce resource into a limitless one – we call it “return on time” … so you to have all the time you need for business, love, parenting, friends and fun. Wingsexperiences.com/apply

Now back to the Amy Gannon. Amy calls herself a “change agent” and her mission is to diversify the entrepreneurial talent pool by catalyzing more inclusive ecosystems for women and minorities.

Co-founder and Director of Entrepreneur Development for Doyenne, Amy is focused on creating communities where women are the designers, builders, and beneficiaries of the ecosystem, not just guests at someone else’s table.

Amy moves aspiring founders through the idea validation, launch and growth stages – and designs, plans and facilitates developmental opportunities for entrepreneurs, including: 2.5-day strategic planning retreats, a year-long founder series for leadership development, and one-on-one and peer coaching sessions. She is building Doyenne’s online platform with learning opportunities specifically designed by and for women entrepreneurs.

Also Doyenne’s fund manager coordinating its investment committee and accelerator, Amy is now building accelerator for community leaders who want to build a Doyenne presence in their own city. Launching in 2020, in an initial 5 cities, Doyenne has a 5-year expansion plan that will make it one of the largest, active communities of women entrepreneurs in the country.

Amy is also one of the founding organizers of the Social Good Madison Accelerator for startup projects and ventures with a social impact mission – as well as a member of the Startup Champions Network.

So are you ready for Amy Gannon? I am. Let’s fly!

Melinda Wittstock: Amy, welcome to Wings.

Amy Gannon:    Thanks for having me.

Melinda Wittstock:         You call yourself a change agent. What are the things that you most want to change?

Amy Gannon:    I think, I want to change the systems in communities that shut people out. I have a personal life mission that is more powerful women in positions of power period.

Melinda Wittstock:         We share that one. I mean, it’s really interesting because when women actually get together and work together, we’re unstoppable, and yet often, we tend to self isolate. It’s such a conundrum. What is the reason for that? Because when we do get together, I mean, it’s amazing, and yet I see so many women stuck in that scarcity and competing with each other rather than competing generally.

Amy Gannon:    I think that that’s the cultural narrative that has been put forward. It’s both structural in the sense that if there’s only one woman going to be on the board, I want it to be me. That tokenism that we’ve had for decades with women and people of color creates a dynamic of scarcity, and then the narrative that’s put forth that women have to fight for that single position is actually a piece that is oppressive to ourselves, and so when we move past, nope, there’s not going to just be one woman on the board. There are going to be three, and we’re going to bring each other up.

Amy Gannon:    Then the narrative gets shifted. It says women work together well. Women are powerful. They’re not going to compete. Within our organization, we try to create an organizational culture and an environment where women don’t feel that, where they actually feel like we all rise together and have to be better together than we are separately. I think, women actually… If that’s the rules of the game, they thrive in that space. It’s beautiful to watch when that happens. It’s really beautiful. It’s really important when you’re trying to create that space in your company or your organization to really give voice to we are all where we are.

Amy Gannon:    We all bring talent. We’re all permanently beautifully imperfect. We came to the planet that way. We’re going to leave the planet that way, so let’s just see what we can get done together.

Melinda Wittstock:         It’s interesting because if you look back at the resources and people who’ve done some research into our brains and how men’s brains and women’s brains develop differently over the millennia. Men, because they were out hunting Wildebeest or whatever, at a certain point, started commerce. They’re saying, “Okay, well if you have that and I have this, why don’t we trade that or whatever,” whereas women, we’re back at base doing everything. Doing everything else, really being the doers and really being connected in community. Actually, we’re relatively new in a way to commerce.

Melinda Wittstock:         One of the things that I see play out a lot, and this is interesting to me, I see women do things like haggle the price with other women, but not question the price with a man. Have you seen that too? I mean, I’m a little bit older than you, and maybe it’s a generational thing, but I see that all the time, or I see men who have a deal and they tell other friends about the deal, and they’re like, “Hey, you want to get in on this with me? I’m sharing this. I’m in. Are you in?” “Yeah, I’m in. Are you in?” Whereas women, not so much.

Amy Gannon:    What I want to be clear about is that one of the guiding principles in our organization going in is that women aren’t broken. We’re not in the business of fixing them. We’re in the business of fixing the system in which we operate. I think one thing that we’re clear about is that actually, all those things we tell women to stop doing, we need more of that in the world actually. We need more men [crosstalk 00:10:18].

Melinda Wittstock:         Right. Well no, I mean, I get that. I totally agree with you in the sense that our authentic feminine power is really stepping up into really owning our empathy and our relationship, our ability to connect the dots, all those things that are archetypically feminine. Those are strengths, not weaknesses. I totally agree with you. Yet, in entrepreneurship, being able to understand leverage, being able to invest, I find a lot of women really shy away from investing, for instance. Why do you think that is?

Amy Gannon:    I think that, well, that has not been presented to them as a viable opportunity in the way that it’s presented to men. Then I think the way that investment and particularly venture capital or angel investing is presented, that whole dynamic is not one that women really buy into, and so one of the things I think is that as women start to own… Women have incredible financial power, and we’re not leveraging it to build entrepreneurial economies. We will be philanthropists before we’ll be investors.

Melinda Wittstock:         Well, that’s interesting too. I agree. I think I’ve seen this firsthand as somebody raising money for some of my technology companies. It was interesting, I mean, you’d talk to women who had tremendous net worth and they would think nothing of writing a check for $1 million to a charity, but ask them for $20,000 for a startup that was solving the same issue that the charity was solving, likely even better, more efficiently, they would just freak out or say, “No, that’s for my husband or I don’t do that or whatever.”

Melinda Wittstock:         Irrespective of the fact that that 20,000 is also going to be a tax deductible thing, and it’s less money, and it’s actually going to create jobs. It’s going to do all these other things. There’s a disconnect there, and it’s a, I guess, personal mission of mine to try and get women a lot more interested in lifting other women in that way.

Amy Gannon:    And leveraging the various sources of power that they have to open doors. [inaudible 00:12:49] the same thing. The way women write checks versus the way men write checks is very different. I do think one of the things I think to get the way women grow into a role or an identity is by learning about it and through relationships. I think, the same way we grow more women entrepreneurs through Doyenne of giving knowledge, giving recognition to what you do know, making you visible to us, and then connecting you with other people who are having similar experiences the same way in a sense that we’re going to grow more women angel Investors and more women VC partners, because their path to isn’t, “I just decided I was going to be one and now I am.”

Amy Gannon:    They want to be good at what they do, and so they find education and practice and connection with other people as the means of crafting their sense of self as an investor. I think there are a lot of programs popping up and growing nationally that provide that pathway to becoming an investor that I think is really a way that women will identify with and how they will try on that identity, adopt that identity, and build that skillset. If we’re going to grow more creating the narratives that yes, you can be an investor, and then creating the mechanisms that allow them to embody it and grow their sense of self in that.

Amy Gannon:    Then when those gates open, all bets are off. I mean, women are going to… It’s going to be incredible.

Melinda Wittstock:         Amy I think so too. What strikes me is what is external to us that’s holding us back and what is internal to us that’s holding us back. Because when we’re in a changing environment, we can only come into a new environment and create that new environment from where we’re coming from. We do take a lot of old mindset issues or old fears. Actually, I see a lot of women with fear of success, “Wow, if I really succeed, if I really step up, I will like, wow, my friends aren’t going to like me or I’m not going to have a man or whatever.”

Melinda Wittstock:         It’s a really primal fear, like literally being cast from the tribe. We have these internal things that hold us back. Then we also have external things too, like venture capitalists …we only get 2% of the money. Where do you see that line and how do you see that changing?

Amy Gannon:    This relates back and is related to my ideas about what inspires me right now. When I think about this, I think that some of the internal fears women have were not they didn’t arise because we have ovaries. They arose because we’ve watched generation after generation after generation of what happens when a woman toots her own horn. What happens when a woman tries to negotiate? What happens? There are [inaudible 00:16:16] classes to that. The internal fears are based in a structural thing, but additionally, the path to breaking down those pieces, those structural patterns of behavior is to make it an internal decision that collectively we’re not going to tolerate it anymore.

Amy Gannon:    Collectively, we’re going to be powerful in our collective so that we’re powerful in our individuals. If there are many women saying, “I’m going to negotiate for more and you’re going to get used to women negotiating with you,” then the consequences become less real and we have to change things. There’s this internal rewriting the narrative in our own head, and through that beginning to rewrite the narrative of the community and society and what we hold out as what are the options for women.

Melinda Wittstock:         What advice do you give women when they’re walking into, say for instance, a venture capital meeting and everyone in the room is a guy, or when they’re walking into say a sales meeting, they’re doing like an enterprise sales type deal, and all the folks in the fortune 500 company with the exception of maybe there’s one woman in the room or maybe two? How should women handle themselves in that situation?

Amy Gannon:    I think some of the conversations we’re having with women is talking about… I’ll use the investor pitching as an example. The research shows that the differences between when a woman gives the exact same pitch that a man gives, same business, same pitch, men get questions about how are you going to make it awesome? Women get questions about how are you going to make it not fail?

Melinda Wittstock:         I know there’s some research on this, and it’s extraordinary, isn’t it? Automatically, women get on the defensive. I know this happened to me before I knew better. You just go into the justifying yourself and all of that kind of stuff. Oh my gosh, you got to change the question.

Amy Gannon:    Yes. That’s where I was going to go with that. Those are fundamentally two different conversations, and one’s a conversation that sees everything that’s wrong and one’s a conversation that sees everything that’s right. When we find that’s a pattern, it’s the pattern that’s been studied. We know going in, if the room is full of male investors, many of which are often older than the women who are pitching, we know that’s where they’re going to go. If we know they’re going to head down that road, we’re not surprised by it. Then we can start to navigate them away to the other kinds of questions.

Amy Gannon:    It doesn’t mean we don’t answer, but we can begin to think about how do we shift that question from not getting defensive like you said, and shift that question from what are the things that are wrong to what are the things that are right. Now, one of the things women do and the research also shows that women are pretty good judges of their own abilities, and they’re pretty good judges of where their businesses are at, whereas men have a tendency to way overestimate their own abilities and way over estimate where their company is. Women come into a context that expects overestimation.

Amy Gannon:    They come in with realistic, and so if we understand… There’s a song I like. It says, “I knew the rules of the game before I broke them.” We can’t shift the rules if we don’t know what the rules are, so really understanding the dynamics that are going to happen when you walk in the room from an objective point of view, this is what’s going to likely unfold and then how do I navigate that toward a better outcome? Many times, we just don’t know the rules of the game. We don’t understand how the system works.

Amy Gannon:    We’re often nervous going into these kinds of conversations, right? Then we get questions that are basically telling us we’re going to fail, so it’s incredibly challenging, but if we can know those dynamics, go in with the strategy for navigating those dynamics and not take it personally, we might end up with a much better outcome.

Melinda Wittstock:         Well, not taking it personally is very important. I think we take it personally when there is a little niggle inside us, consciously or subconsciously, that maybe we’re not enough. Maybe we’re not up to it. If someone then challenges us, we’re going to take it personally, right?

Amy Gannon:    We’re going to get triggered in that way and then react.

Melinda Wittstock:         Absolutely. I mean, and this comes around every time on this podcast. When we’re talking about business, we’re actually talking about personal growth because it always comes around to that. I mean, I’ve gotten to the point where those trigger opportunities for me, I welcome them because I’m like, “Oh my God, if I’m upset about something or someone or some situation, it means that I still have some stuff to heal within me or stuff to just let go of. It’s just not serving me. I don’t need it anymore. Goodbye.”

Amy Gannon:    There’s insight to be had if we’re willing to look.

Melinda Wittstock:         Yes. Absolutely there is. What do you think is going to change the game though for women getting access to capitalize? You saw many women with highly scalable businesses that could be Unicorns in the technology area primarily that just don’t have the funding that they need?

Amy Gannon:    I know that there are many ways of… I think there’s what we talked about in terms of getting more women leveraging their financial power as investors. I see some challenge to the current process of investing. It’s not just who’s investing, but the process of selecting businesses that there is some challenge happening there. As we keep challenging the ways investors do their due diligence and the ways they identify and select what businesses are great businesses will change, I think, more programs that really help women with getting ready earlier in their businesses and getting ready for how do I take investment, how do I seek investment, how do I pitch my business for investment that they are knowledge is power and networks are power, so getting more women tapped into a network and getting them more knowledge about how the system works.

Amy Gannon:    Then I think there are also just different pots and types of money that we need to grow that… There is funding for things that are not the gazelle, high growth, immediate return kind of investment, but that are… I sometimes call it slower money. I’ll take a smaller return for a longer-term play, a longer term investment. I think the more pots of money for different types of scalable businesses is better for the economy overall as we grow that. I think women will push that. I think, how women will deploy their investment dollars will look different than how men have traditionally deployed their investment dollars.

Melinda Wittstock:         I think that’s true. I think the VC model really is broken. I mean, it doesn’t really work for entrepreneurs. I mean, often what’ll happen… I mean, even for men, it doesn’t really work because the VC is basically playing a numbers game. He for the most part is saying, “Okay, out of 10 of you, I only need one of you to succeed, so I don’t really care what happens to the other nine of you.” A lot of founders will lose their businesses. Someone else gets hired. I mean, really when you raise that kind of money, you’re selling a piece of your company and so you have to be really, really conscious of what the terms are, not just the valuation, all these sorts of things.

Melinda Wittstock:         It’s really important for women to get educated about all of this. There are other ways to raise money that’s non-dilutive and all of that. I don’t know. I just think it would be great for women specifically to get into conversations about how we can fund each other as best as possible. For all the folks who come through your programs at Doyenne, what are the biggest single things that they’re struggling with? What is the hardest thing right now for women in business do you think?

Amy Gannon:    Well, I think in many ways, the things that are hard for male-owned businesses is similar to what’s hard for women on businesses, but there’s a layer there, so raising money is hard. It’s additionally hard when you’re a woman, right? Getting customers and getting attention in the noise of all the grants that are out there or all the companies that are out there, and how do you position yourself challenging for everybody and additionally challenging sometimes when you’re a moving entrepreneur. I think in that respect, the vast majority of our time is how do you build your business and what are the implications that arise based on your experience as a woman?

Amy Gannon:    One of the things, I think, and it’s been traditionally challenging for every woman building her career is navigating family life. This notion out here that… This is many ways changing our assumptions about what makes a good entrepreneur, and this assumption that you have to give up everything else in your life and work 16, 18 hours a day. If you’re not willing to do that, you’re not serious and you’re not committed and you’re not good. I actually excuse my language called bullshit on that, because, really, if we say what brings your A game to the work? We want your best self, your most creative, your most productive, your most efficient self doing a work at building a business.

Amy Gannon:    It’s certainly not somebody who doesn’t have any interests outside of work, who has no relief outside of that, who isn’t sleeping or eating or taking care of themselves. None of that leads to bringing your A game. I think when we shift this woman trying to… They just don’t live compartmentalize. They understand their life in an integrative way, and them trying to get legitimacy and build an entrepreneurial life that honors that I think is particularly challenging for women.

Melinda Wittstock:         Yes.

Amy Gannon:    You said just a minute ago about how the VC system is broken for men too.

Melinda Wittstock:         It really is. I mean, it really is. I think there’s other ways of doing business. This is where I’d love to see women really get together and collaborate and invent new ways.

Amy Gannon:    Then I think men will benefit from those ways, right?

Melinda Wittstock:         It’s interesting. It reminds me of this quote from the Dalai Lama who says the Western woman is actually going to help heal men by healing herself.

Amy Gannon:    I totally agree with that.

Melinda Wittstock:         I think it’s so interesting that you mentioned philanthropy that we’re women. I think it’s true, women do go into business much more on a mission driven basis. What’s fascinating about this is one of my companies looks at social media data. We saw using social intelligence algorithms and whatnot. One of the things that we have really seen over the years is that companies that have a mission and have a clean supply chain and diversity on the board and all these sorts of things. That step them up into much more of a social good outperform hands down their rivals that do not have those things in place.

Melinda Wittstock:         This is so helpful for women because we have a tendency to be more thoughtful about that. Not that men are not, but just that we do tend to gravitate much more to mission driven businesses.

Amy Gannon:                    I agree.

Melinda Wittstock:         What’s next for Doyenne? I know you guys started out locally. You’re in the Wisconsin area, Madison, Wisconsin, and you want to scale, and scaling is always a challenge. Tell me about that. What are some of the difficulties and challenges of scaling your business?

Amy Gannon:    Our mission with Doyenne is to create communities where women entrepreneurs from all backgrounds can thrive. While we provide direct service for women entrepreneurs, we’re actually mobilizing the community so that the entrepreneurial ecosystem is designed by, built by, and benefited by women. We’re not guests at that table. We are the owners of that table alongside men. When we scale, we need to find mechanisms that allow us to be efficient in multiple cities and mechanisms that allow us to mobilize the local leadership in each of those cities so that we can transform it.

Amy Gannon:    Our vision now is really what we are going to design is an accelerator program for Doyenne ecosystem builders. By the end of next year, we will open applications for cities to apply to create a Doyenne presence in their city. We’ll select five cities that we’ll work with over a 18 to 24-month period to get Doyenne launched in their communities.

Melinda Wittstock:         Oh, that’s great. That’s awesome. I’m curious though. I mean, you organize it as a nonprofit. Why did you do that?

Amy Gannon:    We really see it as… There were a couple of reasons why, but we really see it as a community activism versus an individual profit organization, and in that way a nonprofit for us, and certainly at that time made the most sense from a legitimacy perspective, from an access to, because we’re a nonprofit, sponsors and grant opportunities, and so that was how we made that decision to do that.

Melinda Wittstock:         I’m curious because I once launched a nonprofit for much the same reasons, and then ultimately ended up regretting it because I got so constrained by the terms of the grants. When it came time to be nimble and change and take advantage of other opportunities, I was constrained. It’s an interesting trade off.

Amy Gannon:    It is an interesting trade off. I would say when I talked to women, and they say, “I’m going to be a nonprofit,” I say pause.

Melinda Wittstock:         Right, exactly. It’s true. I mean, because I always… I like to ask this question too, because I always wonder if there’s something like, “You know, I don’t know. Make everybody else wealthy, but not me.”

Amy Gannon:    Personally, just… I suggest to women, “Just because you have a social impact you want to make doesn’t mean you have to be a nonprofit. So let’s really think through strategically why you want to do that and what the implications are.” There’s a lot more that the B Corp is… There’s more things coming down the line that are really recognized a hybrid nature. Secondly, personally, I would never found the nonprofit.

Melinda Wittstock:         Right. It is interesting, right?

Amy Gannon:    I would not [inaudible 00:33:12]. I love Doyenne. I’m happy that we’re a nonprofit. Personally, there are many, many challenges associated with that. I probably wouldn’t do it again, but I’m okay with that Doyenne is this. I’ve been thinking about that.

Melinda Wittstock:         No, it is. It is, and it’s interesting too, I mean, these social missions. Again, those sorts of companies are more profitable. It’s not an either or. I mean, the profitability and doing good go hand in hand. It’s so, so important. As you grow Doyenne, I mean, where do you think it is going to be and where do you think women in business are going to be in the next 10 years? 10 years from now, what would be your wildest dream of success for all of us to have pulled off in the next 10 years?

Amy Gannon:    For Doyenne, I would love for us to be the largest dataset of women entrepreneurs and have granular data about how they engage, what they want, where their success points are, the challenges they’re having so that we can create voice that is really powerful around the shifts that we need to make. Second, I’d like to see a lot more dollars flowing into women-led businesses. One of the things we are focusing on is second and third tier cities. You can really get a hold of the smaller size city and make a change in that city.

Amy Gannon:    If in 10 years we’re seeing cities that no longer have a gap, that women are fully equal within those cities, they create a model of what it looks like and feels like for there to be equitable entrepreneurial economies. If we can see bright spots like that, then we begin to replicate those bright spots and learn from them. One of the things that Doyenne is women navigate the world in a way that they’re always arguing for legitimacy, whether they’re consciously doing that or subconsciously doing it.

Amy Gannon:    Ee don’t even know fully what it feels like to not have to do that because it’s just always present. One of the things at Doyenne is you’re legitimate when you walk in the door. We’re not going to have that conversation. We want to know what are you trying to achieve and how do we help you get there.

Melinda Wittstock:         Right.

Amy Gannon:    Come into our setting and feel things that they haven’t felt before. Part of our goal is this is how it should always be, right? You shouldn’t have to come to Doyenne. If women in these communities say, “Yeah, I know what that feels like. I can go replicate that outside of Doyenne.” If we have cities pockets doing that, then people will say, “Oh, this is what it’s like,” and we will begin. It will be a snowball effect. I see it happening already. I actually think the next decade will be one that we look back on as a real turning point and pivotal if we do this right. I am excited about it.

Amy Gannon:    I have a 13-year-old daughter, and she and her friends are powerful in ways that I definitely wasn’t at 13, and 13 is pretty rough. For young girls to feel powerful at 13, as a middle schooler, I just see younger generations. Let me clarify. I’m hopeful and excited about my generation, and I’m inspired by and thrilled to see where the generations after me take the baton after we pass it on to them, when they grab it out of our hands and say, “This is the way to do it.”

Melinda Wittstock:         I love it. I love it. That’s wonderful. Well, I want to thank you so much for chatting with me about all these big problems and all the great solutions, and putting on your wings and flying with us, Amy Gannon. Thank you.

Amy Gannon:    Thank you for having me and thanks for all that you do to inspire and support women and entrepreneurs.

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Listen to learn the secrets, strategies, practical tips and epiphanies of women entrepreneurs who’ve “been there, built that” so you too can manifest the confidence, capital and connections to soar to success!
Instantly get Melinda’s Wings Success Formula
Review on iTunes and win the chance for a VIP Day with Melinda