776 Jaclynn Brennan: The Power of Female Mentorship

Yes, women are a good investment, so why are so many female founders struggling to find the capital to grow the scale their businesses, and what can be done about it? More and more female founders are turning their entrepreneurship skills to advance other women, and today Jaclynn Brennan shares how her network-as-a-service platform Fyli (feely) is succeeding at connecting women to capital as she’s grown her community almost 12,000 strong.

MELINDA

Hi, I’m Melinda Wittstock and welcome to Wings of Inspired Business, where we share the inspiring entrepreneurial journeys, epiphanies, and practical advice from successful female founders … so you have everything you need at your fingertips to build the business and life of your dreams. I’m a 5-time serial entrepreneur who has lived and breathed the ups and downs of starting and growing businesses, currently the game changing social podcast app Podopolo. Wherever you are listening to this, take a moment and join the Wings community over on Podopolo, where we can take the conversation further with your questions, perspectives, experiences, and advice for other female founders at whatever stage of the journey you’re at! Because together we’re stronger, and we soar higher when we fly together.

Today we meet an inspiring entrepreneur who like Coco Brown who we heard from in our previous episode, has made it her mission to help women entrepreneurs grow and scale their businesses – and get the funding to do it.

Jaclynn Brennan is the CEO and Co-Founder of Fyli (feely), a Network as a Service (NaaS) business for early-stage female founders, offering education, accountability, peer-to-peer mentorship, leadership advancement and funding opportunities.

More women than ever are starting businesses, and more women than ever are achieving billion dollar exits, totaling now some $59 billion. Yet the playing field remains uneven, and many women are learning that if the rules of the game don’t work… change the rules.

Jaclynn Brennan is on a mission to help early stage female founders grow and scale their companies with her Network-As-A-Service platform Fyli (feely). Fyli focuses on a mix of personal and professional development for women, helping us all to be unapologetic about creating wealth, legacy, and impact. Fyli also connects founders to funders, helping members raise $2mm so far.

Jaclynn herself climbed the corporate ladder as a creative executive and branding expert, with 12 years experience as a creative director for luxury fashion brands and leading 22 major corporations to execute winning brand strategies. All that experience is paying off with Fyli, which is growing fast in major startup areas like New York, Austin, Los Angeles and elsewhere. Fyli recently aligned with SOHO House as a global partner, secured a global tour for UBS Bank called Own Your Worth, and partnered with Milan Fashion Week to host the first diversity and inclusion impact experience for US investors and female founders.

Let’s put on our wings with the inspiring Jaclynn Brennan and be sure to download the podcast app Podopolo so we can keep the conversation going after the episode.

Melinda Wittstock:

Jaclynn, welcome to Wings.

Jaclynn Brennan:

Thank you so much, Melinda. I’m happy to be here with you today.

Melinda Wittstock:

Oh, likewise. Well, I think you’re doing something so interesting for women in business with Fylí. Tell me what was it that led you to found it?

Jaclynn Brennan:

Well, Fylí was built as a passion project because it was something that I actually needed. I worked in fashion corporate for about 12 years as a creative director for many different brands. I then left the fashion world to start a tech company with a few male partners. And honestly, Melinda, it was a really challenging time. I did not come from startup life and tech culture. I was really unprepared and I built Fylí because it was something that I needed. I never thought it would turn into a full-time cash positive business.

Melinda Wittstock:

The thing that we do that we’re called to do is often the thing that we’re meant to be doing. And so what was it about, I’m curious what it was about the tech startup that made you say, oh God, I really should just go out and help other women with this?

Jaclynn Brennan:

Yeah.

Melinda Wittstock:

What was the experience?

Jaclynn Brennan:

Exactly. Well, it was just interesting being around my male counterparts, watching how they raised capital, what conversations they were having, and just really realizing that there weren’t many resources available for women. And when I winded up leaving the tech company in 2018 and walking away, I really did a lot of deep dive research into communities that are out there for founders.

So I found different resources like traditional mastermind groups that were about 25,000 to $75,000 a year buy-in, which are completely unaffordable. And then I found things like Chief, which are great, but they’re focused on corporate executive women and not early stage female founders. And then you find things like accelerators and venture studios, but they take equity of your business. So I really did that research to see what is out there on the market for early stage founders that do not take equity and there’s not much. So that’s really what led me into realizing that Fylí could be a full-time business, a private membership community. And I’ve the term NAAS, Network as a Service.

Melinda Wittstock:

I love that ‘network as a service’ because one of the things that women are naturally good at doing, but we don’t do enough in business, is the networking part of it. Because so many things about business is to do with your relationships and especially fundraising for a business and all these different things that we have to do. So I love that it’s a network as a service. So tell me a little bit more about Fylí and what it actually does for women, and who are the women who are your ideal clients for it?

Jaclynn Brennan:

So Fylí is a NAAS, Network as a Service for early stage female founders offering education, accountability, peer-to-peer mentorship, leadership advancement and funding opportunities. So our mastermind is really focused on cohorts. Those are small, highly curated groups of women, usually between eight to 10 women per cohort based upon skillsets, ambition, goals, and commitment. Really to create that 360 ecosystem of thought leadership over a yearlong commitment. So you have to apply your vetted and it’s really based upon those ambitions, goals, dreams, and skills. And we run this 12 month curriculum really focusing on all of the things you would need to go on your founder’s journey from conquering imposter syndrome, to building your advisory board, to perfecting your pitch, to learning about what types of capital you’re able to raise for your business to marketing and P&L. So it’s that full spectrum.

Melinda Wittstock:

So I know when I was starting out as an entrepreneur, there were no real resources like this. I think even for men, there weren’t very many. Masterminds even were a relatively new concept. And just that feeling of oh my God, I got to do it alone. And now it’s so great to see so many different resources. And I was beginning to think, oh God, well, all these things are solved now for women now that I’m on my fifth business. But to hear you speak about it, Jaclynn, none of them were really hitting the specific thing that women need. So when they apply and they come to you, what stage, they’re early stage, but have they started their business? Where are they on that trajectory?

Jaclynn Brennan:

That’s such a great question, Melinda. And I would say we really break it down into two different profiles for founders. One is completely early stage. So pre-revenue generating, you have the idea, you have the business plan, you’re ready to rock, you have left your full-time job or you’re consulting as you’re ready to grow and scale and step into this business. And then the second profile is a more experienced, seasoned founder up to Series A. You’ve raised some capital, you’re generating revenue and now you’re ready to really fly. Or this might be your second or your third business and you want to have support along the way as you’re building.

Melinda Wittstock:

Oddly enough, I’ve been looking for something like this and there are a number of different women’s groups that I’ve found that are specializing in certain areas. I haven’t found exactly the right one where you are with other women who literally are going through the same thing as you’re going through. Because there’s not that many of us, really.

Jaclynn Brennan:

And it’s interesting because there’s so many amazing groups out there, but I have yet to find one that’s really focused on building out those skill sets. So there’s a lot of networking happening. There’s a lot of online courses and subscription communities that are self-led and self-taught. But what I found is that when you’re paired with a group of women of like-minded women who are non-competitive, so it’s industry agnostic, every woman sitting at that table in your cohort is going to have a different skillset, expertise, and superpower to be able to contribute, you’re going to hold each other accountable. It’s so much more than just hopping on a Zoom and sharing about your month, your day, what’s happening in your life. But it’s saying, Hey, what do you think about this strategy? Or who knows the connection to here? Or I’m following up with you, did you do that thing that you mentioned you were going to do last time? Holding you accountable.

Melinda Wittstock:

I love that. So are all the women really disciplined about actually doing that? Because I know so many people talk about this, that we all need this, we all need to do more than you go girl, but actually… Buy from each other, mentor each other, teach each other, invest in each other’s companies, these sorts of things, actually really showing up. Do a hundred percent of the women actually do that?

Jaclynn Brennan:

So I’d love to say that a hundred percent of the women do, but I would say at least 85% of the women actually do. They’re there to help each other to support each other. We have seen women within our cohorts investing in each other’s companies.

Melinda Wittstock:

Oh that’s great.

Jaclynn Brennan:

And then build relationships, long-term relationships so far in terms of looking at our retention rate, we have had women that have joined cohorts up to three years in a row. So it’s been incredible to see that.

Melinda Wittstock:

It’s actually why I started this podcast, to really try and kickstart an ecosystem where women, especially women who have had exits, actually paying it forward to other women. Or it shouldn’t be too hard to just buy from each other or promote each other.

Jaclynn Brennan:

Absolutely.

Melinda Wittstock:

Or all these different things. So bravo or I should say brava to you for actually doing this. How many now in Fylí as a whole?

Jaclynn Brennan:

Wonderful question. So for 2022, we ran four different cohorts. So up to 40. And our global community are friends of Fylí, which means that they activated our events, they get our online subscription details and emails 11,500. And now we’re welcoming in our new batch of cohorts for 2023. So we’re opening our January cohort next week at kicks off on January 10th. And then our next batch of cohorts are going to open in April.

Melinda Wittstock:

So is this Zoom, virtual based or is it in person?

Jaclynn Brennan:

It’s mostly virtual. So we have women from all over the world. 65% are US based, but we do have quarterly meetups that are optional in person.

Melinda Wittstock:

Oh, that’s fantastic. And where are they?

Jaclynn Brennan:

Mostly in large cities like New York City, Los Angeles, Miami, and Austin.

Melinda Wittstock:

All the startup hubs. So meantime though, you’ve really grown this in the past year, your revenue is up by what, some 60% and you’re growing really quickly. There’s a lot of demand. And I am going to hazard a guess that a lot of women have come into entrepreneurship post pandemic.

Jaclynn Brennan:

Correct. We are seeing entrepreneurship fly at this moment as it relates to female entrepreneurship and women starting businesses after the pandemic. And then we’re seeing a huge increase of millennial and Gen Z women starting businesses.

Melinda Wittstock:

Yeah. Because I think there’s a certain point. And in my entrepreneurial trajectory, there was a certain point where I think I launched my first business when I was having my first child.

Jaclynn Brennan:

Wow.

Melinda Wittstock:

Because of the flexibility. Now, I wouldn’t necessarily advise a business when your daughter is six weeks old. Basically the funding came through right at that point. So my life was insane. I don’t even really know how I did it, but you just make it work. But just the flexibility, the actual fact of can you create a business that supports the life that you actually want to lead as opposed to getting stuck in the proverbial glass ceiling or in that corporate thing where you can’t really innovate and you’re always going to have your salary, you’re not really going to generate wealth, not significant wealth. Do you think it’s the desire for flexibility that’s motivating a lot of women now to come into entrepreneurship? Or is it something more? It’s just like, look, these problems are significant problems and nobody’s addressing them. I’m going to put up my hand and I’m going to go and address it because nobody else is? Or a combination of both?

Jaclynn Brennan:

I think it’s a combination of both. I also think what we’ve just all experienced with the pandemic and working from home, it taught so many individuals that you can work from home. It’s not easy, especially when you have children, but there’s certain boundaries you can put in place. And now that so many corporate companies are demanding individuals to go back into the office, I do think that’s playing a major role in people saying that they want a flexible schedule and they want to be able to build something on their own time.

Melinda Wittstock:

So what are the biggest issues that most of the women in the cohorts have? What are the biggest challenges that you’ve seen putting your pattern recognition brain to work?

Jaclynn Brennan:

Well definitely funding is the biggest challenge. As we know, only 2.5% of venture capital is going to women and less than 1% to non-white women. So that is a really interesting statistic that we’re still battling today. It’s definitely funding. Another one would be access to mentorship. So many women are claiming that they are not able to be successful, 48% because they do not have access to a mentor. So being able to build these cohorts and give these women what they need in terms of mentorship, guidance, the resources to grow, it’s incredible to see what they’re able to accomplish in just 12 months when they actually have the support that they need.

Melinda Wittstock:

That’s surprising to me on the mentorship side of things. Is it because women who are ahead of them or have succeeded just aren’t giving back or they don’t have time? Or are these women seeking mostly female mentors or just mentors generally?

Jaclynn Brennan:

So I believe that it’s happening because women don’t ask for things. Oftentimes, women are not asking for what they want and what they need. We’re taught from a young age not to ask. It’s impolite. So I feel like we’re not getting mentors because we’re not putting in the asks out there.

Melinda Wittstock:

Right. Because I’ve found whenever I’ve asked for something, I usually get it. Just even going on LinkedIn and you find somebody who’s doing the thing that you want to be doing and you say, hey, can you help me? Usually people who are very successful often tend to be the most generous people. You got to figure out how to ask. Hopefully, you can be useful to them as well. But what’s the best way of getting that ask muscle activated and approaching a mentor or somebody that you really look up to and you want to learn from and you don’t know them or you don’t know anyone who knows them? What’s the best way to go do that?

Jaclynn Brennan:

So I say definitely look at LinkedIn as your best resource and then make an educated ask. Have something clearly defined in your mind. Go after it, make sure you’re showing up on time for that virtual Zoom date. And then do a really thoughtful follow up.

Melinda Wittstock:

Yes. Because you don’t get what you don’t ask for. So I think learning how to ask is really important. I see that with women too often not asking for help, not hiring early enough, being worried about or seeing hiring a team member as an expense rather than as an investment. What is that person? Not just what are they going to do, but what return are they going to provide for your business? And really thinking more in terms of leverage, which I think that whole concept of leverage comes a little bit more naturally to men in business. They’re used to it, but with women not so much. So sometimes women I think can feel like, oh gosh, I have to do it all myself. And not only that, but I have to do it all perfectly.

Jaclynn Brennan:

Yep,

Melinda Wittstock:

Exactly. That slows down business growth faster than anything. It kills businesses to be in that perfectionism or trying to do it all yourself.

Jaclynn Brennan:

Absolutely. I 100% agree. So I definitely think that it’s teaching women how to make educated and inform asks. And that’s something that we do early on in our cohorts. We make them make asks, we teach them the art of the ask. It’s actually part of our curriculum structure.

Melinda Wittstock:

I love that. The art of the ask. Yes, this is so important. Do you also have an AA for perfectionists?

Jaclynn Brennan:

We say we’re recovering perfectionists. As a founder, there’s no way you can be a perfectionist. You have to be flexible. You’re constantly changing, pivoting, shifting. There’s no perfectionism allowed.

Melinda Wittstock:

No, it’s impossible. It’s actually impossible. And after a while you get used to the fact and you look back and you can easily connect the dots looking backwards. And you see that all the times when you grew as an entrepreneur, when you actually learn something, it was when you were presented with a challenge, you had to figure out how to overcome every step of the way. And so we like to call it failing forward, right? Because-

Jaclynn Brennan:

Yes, failing forward. Absolutely.

Melinda Wittstock:

Because it’s just part of it. I guess another metaphor is a scientist in the lab, you keep trying until the eureka moment like, oh okay, I finally have the formula. And so entrepreneurship isn’t all that much different. I want to pivot though into the big thing though is funding. It is so hard for women to get funded. And what do you think are the main impediments there? Is it just that we’re not networked into the Silicon Valley Boys Club basically? We just don’t have the relationships? Is that the-

Jaclynn Brennan:

I do. I think that’s a huge piece of it. I do think that it’s also because we don’t have enough women sitting on the other side of the table. And unfortunately, when we look at women led and run funds, they’re much smaller funds than the big boys. So it’s really hard to be able to get the capital that you need from a woman-led fund because most of their fund sizes are only 20 million tops, which that is starting to change. And there are some really good resources out there. I actually just published a piece in Forbes that I’d love to share with you about venture funds that are focusing on women that are larger funds. So they’re starting to come out there, but I really believe that it’s because women have not been educated on how to create and craft their pitch on how to speak and ask for what they want and what they need. It’s building that confidence.

Melinda Wittstock:

It really is. I find though that in my own experience with fundraising that the goalposts continue to shift. Like, oh, talk to us when you’ve got, I don’t know, product market fit. So you’ve got product market fit, people are paying, you’ve proven it out. And they’re like, okay, but no, no, no, actually no. Talk to us when you have traction when you’re growing at this rate. And then it’s like, okay, no, no, no, no, you’re still too early. Talk to us when. That I see happening to so many founders, particularly female founders in the tech space. Whereas men are getting funded at an earlier stage, women are having to prove so much more really to the point of de-risking the deal altogether where the word venture seems like a misnomer. It’s not venture at all by the time women get funded. And so staying in the game, women get really good at doing a lot with very little, arguably you could say that creates better businesses in the end. But what do you think about that goalpost moving issue? Have you seen-

Jaclynn Brennan:

Yeah, that I do see that all the time and it’s one of the things that really gives me the motivation to wake up and do what I do every day with Fylí. So when I see things like that, the proof is in the data. And I have some data points that I’d like to point out that I point out to venture capitalists all the time. And that is number one, startups with female founders are exiting one year faster than average on the market. Number two, the value of exits for startups with female founders has skyrocketed to 59 billion. So more than 40 points higher than the overall market. And lastly, when VCs invest in women, they make more money. Women-run businesses deliver higher revenues equating to more than twice as much per dollar invested. So I lean back to the facts.

Melinda Wittstock:

See? This is so compelling and yet these men don’t know that. So we all need a little pamphlet or a little slide in our slide decks that say this.

Jaclynn Brennan:

I actually have one in our C deck. And literally, it’s titled Women are a Damn Good Investment.

Melinda Wittstock:

Right. We all need that same slide in every single pitch, seriously. Because I think it’s interesting, the other thing that happens to women, especially if they’ve created a business that’s really innovated for a predominantly female marketplace where the male investor just doesn’t understand that marketplace doesn’t understand the customer. And I’ve found myself, well, mentoring also a lot of women entrepreneurs who are in that space, whether it’s like fem tech or whatever it is, and just telling them to say, look, you’re an investor, you’re not our customer. This is a huge market. It’s a massive addressable market. And just being really on that and you have to repeat it almost sometimes over and over again. You can’t assume necessarily that you’ve even been heard just because you said it.

Jaclynn Brennan:

Absolutely, absolutely. And just my other piece of advice that I say is if someone’s not getting it and they keep asking you to come back, then they’re not the investor for you, then you have to go seek out someone else. It took me, as we were raising our pre-seed round for Fylí, it took me probably about 120 no’s before I got a few yeses. And it’s an uphill battle. It’s really tough to constantly hear no and to keep confident and keep believing in yourself. But there are people out there that are going to believe in you and your mission and it’s just a matter of finding them.

Melinda Wittstock:

Ah, a hundred percent. So how do you see Fylí growing over time? What’s your ultimate vision for it?

Jaclynn Brennan:

Great question. So I see Fylí being the Chief for early stage female founders. So there’s a few differentiating factors other than Chief. Chief focuses on corporate executive women. We focus on early stage founders and Fylí is already global. So we already have women in the United States and Europe and Latin America, and now in China within our cohorts. So we are looking to grow Fylí in a large way and we’re looking to build our tech component and our app. So we’re now raising our seed round. We just opened it this week, actually. So pretty exciting.

Melinda Wittstock:

Oh, fantastic. Good luck with that. That’s amazing. It’s exciting.

Jaclynn Brennan:

Thank you. Very exciting. And yeah, we’re looking to basically become the Chief for early stage female founders.

Melinda Wittstock:

I could imagine a great argument to all the VCs and angel networks or whoever you’re talking to. It’s like, look, you guys are deal flow for all these guys.

Jaclynn Brennan:

Absolutely. Absolutely. Hundred percent.

Melinda Wittstock:

And you’re qualifying them and giving them the training. You’re de-risking deals basically for all these folks.

Jaclynn Brennan:

Absolutely.

Melinda Wittstock:

Very good. I think sometimes just in the way we talk about things, it’s an interesting delicate balance between being authentically who you are, not trying to be a man because we’re not, we’re obviously women. And so being in authenticity while at the same time, being able to speak that very masculine language, how do you reconcile those two things? I think that’s hard for a lot of women.

Jaclynn Brennan:

It is. It really is. And for me, I think it really boils down to authenticity, showing up as your true self. I’m not trying to be a man, I’m not trying to speak like a man, but you do have to stand firm in your beliefs and you have to go about pitching with confidence. Because what I’ve learned is that an investor, the average time they’re going to spend looking at your pitch deck, which I can actually track it with Docusend, I encourage every founder to use that when you’re sending out your deck, the average amount of time they’re looking at your deck is one to two minutes. That’s it. So they are basing their investment on the pitch and on you as a founder.

Melinda Wittstock:

Right, right. And making sure… If you’re a first time founder, that’s tricky because you don’t have say an exit or a previous or whatever. And it is you. I’ve been told that like 60% of the investment decision is basically on the team, on the founding team. Are these people going to be able to… They have a plan, it’s not going to go according to plan because it never does.

Jaclynn Brennan:

Yeah.

Melinda Wittstock:

Are they going to be resilient? Are they going to be able to pivot? Are they going to be able to work well together? Are they going to be in all these sorts of things? And it’s hard to get that across if you’re just looking at a pitch deck for a minute.

Jaclynn Brennan:

Exactly. Exactly. So you have to be able to show up as yourself, but also to show up strong and resilient and confident.

Melinda Wittstock:

It’s funny, a long time ago I was part of a cohort of an organization called Springboard. It was started in 2000 because women weren’t getting funded. And it was an early version, I think of what you’re doing where there was a bootcamp, teach us all how to do our pitch decks and that kind of thing. It wasn’t as much master-mindy as you, but I remember we had this bootcamp and we had to do a two minute pitch about the business and then we had to do a two minute pitch about ourselves. And it was amazing how many women forgot to mention these amazing accomplishments of theirs. Like a woman who had had a $500 million exit and forgot to mention it. Or another woman who literally was doing something in the space area. And she’d actually been an astronaut, but forgot to mention that.

Jaclynn Brennan:

Oh my goodness.

Melinda Wittstock:

And I remember thinking, wow. And then the other thing that we noticed is a lot of women, when it got to the point to ask for or how much they were raising, sometimes it would be like, I’m raising 5 million? Like it was a question mark at the end of the inflection of the voice. And so there are little things like that that really like, oh gosh, we have to get better at being able to brag on ourselves and just really know what we want and be comfortable. Again, going back to asking for what we want, all of these things. So it’s so good that you’re helping with all of this. This is a big, big thing. So how do people apply to join Fylí?

Jaclynn Brennan:

Great. So people apply by visiting our website, fylitribe.com and just hit click on apply. And right now we’re currently taking applications and hosting interviews for our April, 2023 cohort.

Melinda Wittstock:

Well, I’m going to check it out and I know a lot of women, oh gosh, who could really, really benefit from this. And so honestly, Jaclynn, thank you so much for doing this work. It’s so important for everybody.

Jaclynn Brennan:

Thank you so much, Melinda, for having me. It was wonderful chatting with you today.

Melinda Wittstock:

Yeah, I really appreciate it. Well, good luck with everything and good luck with your round. Keep us posted, and thanks for putting on your wings and flying with us.

Jaclynn Brennan:

Thank you so much. Take care.