Money is a Tool: The CEO's Guide to Financial Boldness

18:23Jeannette:That said, in our mastermind level program, which is a holistic business program, it isn't just about sales. We cover sales, marketing operations, and mindset, which is really where that purpose piece comes in. We actually have a vision tool that we've created that asks them about how they want their life to look, how they want it to feel, what they feel they were born for, and it'll spit out a plan for them to ensure that they're not missing what matters most. Also, I do an annual sabbatical 30 days with my family and on that sabbatical, I'm not working. So it's 30 days to 45 days where I can just do that deep dive spiritual reset on making sure I'm still in alignment with what I am here to do.

19:03Jeannette:But for a lot of people, they feel very passionate and or multi passionate and where they lack is a plan. So we really come in when you're ready to take all that passion, put it into a plan and profit from it. In our mastermind program, there's one-on-one coaching, there's more support for that. And so there's more work on the vision and on the mindset. But for a lot of businesses, to be frank, they're not surviving because they don't have the cashflow to survive. So we really do want to make sure that they're able to live another day, feel aligned, but also ensure that they're able to survive another day in business.

19:39Ashley Kirkwood:Yeah. And you know, Ashley, you were sharing your journey earlier about how you started life, the different things that happened to you in the corporate world. What's been the most difficult thing for you, would you say, in business?

19:54Team.

19:55Ashley Kirkwood:Do you want to expand on that?

19:57Jeannette:Well, I think anyone who's scaled a bit, well, at least for the majority of people that I've talked to who have scaled their business, multiple millions of dollars, team has been a challenge. So hiring people, having to let go of people who are very well-meaning, but just can't live up to the current standard of the business. No one likes doing that. Finding highly competent, qualified people who understand work ethic hasn't always been easy. I think that we also live in a time where people are just so burnt out from so many things that they just don't really want to work as hard as they've used to.

20:29Jeannette:And now, I don't know if companies, I don't know if your companies deal with this, but we have a gig economy in the United States. So where you could make 40, 50 ,000 on a job, you could, or to your point about purpose, there's a lot of people who just feel like I'm not passionately connected to my work. I'm just going to drive Uber and not work a traditional job. So when you're competing against all those things, it can be challenging as a startup to really manage and grow and scale a team. That said, where we have found a lot of incredible talent has been outside of the U.S. as well. So we have several team members in the Philippines, different parts of Africa, Trinidad, India, and Pakistan.

21:08Jeannette:And so we've been able to really build a global workforce, which is great, but then we have to make sure that we still stay connected and aligned since we all work on different time zones. So we have a day team and a night team at Speak Your Way to Cash. And we have a day manager and we have a night manager at Speak Your Way to Cash. So just making sure that all of us stay aligned. And then also as your company grows, someone who may be great when it was a smaller company may not be great as it grows larger and bigger. And so just always working with different people, relying on different people to do their part of the puzzle, probably would be the most challenging piece.

21:43Ashley Kirkwood:Yeah, so I agree, people, because you're only ever one person's 24 hours in a day. And if you don't have a good team with you, then, you know, it's going to be very difficult to scale your business 100%. And actually, for yourself how do you stay humble because you know you're in a world where you're working with businesses you're working with individuals about go go go come on sell turn this into money you've got to survive you've got to hustle you've got to close the deal right takes a lot of confidence a lot of energy to to kind of be like that and the confidence sometimes as well you know how do you stay humble through the process when you're working with people because it's quite a quite a difficult balance I think between shouting about the success and maybe this is a European versus a US perspective as well cultural differences but how do you stay humble as a leader throughout all of this?

22:33Jeannette:What's your definition of humility?

22:36Ashley Kirkwood:Well where you're grounded you know and and you're able to come across with authenticity and vulnerability and not you know shout about the success but also acknowledge that we don't always get everything right as a leader so for me you know being humble is about being able to be authentic and not that everything is positive all of the time but being really true and honest and clear on on all of those things as well so for me it's about authenticity the highs and the lows and being able to you know sort of show gratitude I suppose and acknowledge the things that we're not so good at as well and that we need help with you know it's interesting

23:18Jeannette:because I think that if you are an honest, a confident person, then you know what you're good at and you know what you're not good at. And it's way less pressure being a CEO when you're not faking it. So who I am is who I've always been. I'm not pretending to be something that I'm not. I didn't even do that, thank God, I didn't even do that as a lawyer much in corporate because I went to a firm that really allowed me to be myself regardless. One thing that I do is I am very clear about who I am outside of work. So I'm a Christian. I believe in God. I've been married to my husband since I was 23.

23:54Jeannette:He keeps me very honest. He's gonna always make sure that I'm like on my P's and Q's. And if I do something wrong, he's definitely probably the first person to tell me or the second. I also keep people around me that I can trust, not fans. So I have fans for sure. I have people who just love everything and they're just like, oh, you're so great. But at the end of the day, that wouldn't be who would be around me in my inner circle. The people that are in my inner circle know me for me, love me whether we have a great year or a bad year. And I'll tell you, the other thing is, I am honest with my clients.

24:27Jeannette:When we have a launch that works, we tell them. When we have a launch that doesn't, we tell them. Because again, to me, the money does not matter that much. Like, I would have been rich as a lawyer. So I wouldn't have become an entrepreneur to get rich. My profession, you know, the lowest paid partner at Kirkland made over a million dollars, equity. So it wasn't about the money. It was literally about wanting and being very passionate about seeing other women, particularly diverse women, thrive as experts and not be treated bad. I'm also a big student of history. So I understand that there were times when in the U.S., they typically think that the first black woman millionaire was this woman named Madam C.J.

25:06Jeannette:Walker. She had a hair care line. But she wasn't. The reason why they thought she was the first was because she was the first woman who could confidently show her wealth. It was dangerous for people who looked like me in the United States to actually share what they made, share their wealth. But Madam CJ Walker ended up helping a thousand other women to get wealth too, because she could be public about it. So for some people, it could be like, oh, well, I don't want to share this. And I don't want to share that because if I do that, people are going to look at me and they're going to think I'm arrogant.

25:34Jeannette:But if you know who you are for real, you're not doing anything for other people. You're on earth to fulfill your mission from God. And so you're going to operate with that in mind. You're going to work with that in mind, and you're going to share what you're supposed to share to fulfill your unique mission. So I think that the way you stay humble is by understanding that you don't control as much as you think, but everything you control, you better make sure that it's in your control. Anything I control, I'm going to make sure I can control it. If it's outside of my control, then it's in God's control.

26:04Jeannette:So I believe inputs on me, outputs on God. If I give my best and it doesn't work, I don't have to be embarrassed of that. Now, when something doesn't work, your initial response is shame. It's like, I should hide this. I shouldn't tell people this. I force myself to tell people because I don't want anything to make me feel shameful or make me hide. As a leader, that is so dangerous. And then I also just make sure that I don't, I'm not moved by the opinions of other people. I think that if you can, if you can navigate business, take people's opinions, you know, if they have an opinion that makes sense, then we'll implement it.

26:38Jeannette:If they don't, then we won't, but you can't be moved by the opinions of others. If you live for their applause, then you'll die at their booze. And I've experienced both. I've experienced public criticism and I've experienced people being like, oh my God, this is amazing. So I think you just have to be measured and keep real people around you that'll tell you when it's wrong. I pray, hang out with my family. I do weekly date nights. I do mommy daughter days. Like I do all the things. Like I have a plan for every area of my life where I want to see growth, whether that's spiritual, personal, relational or familial.

27:10Jeannette:And that is going to help you out. But I will say, I think that most people kind of force a false humility on women. And I'm really against that because I've seen historically how it has not been helpful or beneficial for people.

27:23Ashley Kirkwood:So I want to talk a little bit about leaning to the women in business, because I was always the only woman in the boardroom with a P &L in very large listed businesses. you know i was at footsie 100 footsie 250 businesses in the boardroom so i know very well firsthand how difficult it can be for a woman in business and it has changed it has improved i will say but there's a lot more there's a lot a long way to go and one of the um statistics is around women raising finance raising capital right whether it's some vcs private equity etc And in the UK, only 7 % of VC funding goes to women, right?

28:03Ashley Kirkwood:7%, 93 % goes to men. I don't know what the number is in the US. But for you, Ashley, have you had to be in that position where you're raising finance to grow the business? Or have you worked with female leaders, female entrepreneurs that are looking to raise capital so they can grow? And what experience have either you experienced yourself or seen your clients experience when it comes to raising finance?

28:29Jeannette:Yeah. So, no, I'm a self-funded company, meaning, you know, we generate revenue. And through the generation of that revenue, we use our excess revenue to make more money. Like we're self-funded. We've taken out loans. We've also seen in the U.S. like there's a really low percentage of our businesses that actually get even loans from banks, not even capital. So we just keep going. I think that you just have to make a decision that you're going to keep going regardless of what's going on. That said, I have clients who are in the process of raising capital right now. And one of the things that I've experienced is if they don't, in some instances, if they don't understand something or if they don't feel comfortable with the terms or if they don't know the terms, they won't go full-fledged.

29:12Jeannette:And so I have been able to help them to set realistic high capital raise goals based on the viability of their underlying product. And many of them are in the tech space. I personally believe that we also should look at, there's all ways to, we could do crowdfunding. We could have venture capital. We could do a friends and family round. A lot of our companies don't even do, they don't do any of those. And I didn't do any of those in the beginning either. And a big piece of it was if your Rolodex, if you don't believe your Rolodex has excess capital, you don't want to do that. Now, my reason for not raising wasn't even that.

29:45Jeannette:It was that I didn't under, A personal brand business typically doesn't raise venture capital because it's tied to the face of the founder. So the exit potential isn't the same as a tech company or something that's not tied to the personal brand of the founder. So in fact, we're actually working on another venture where we are going to raise capital for that venture. And for my clients that are in the middle of a raise, a lot of our conversations are around them feeling comfortable asking for money. in some instances people have come to them like hey I'd like to invest in this how can I do it because it is a company that is investable that makes sense for an investor and I wonder and I don't have any data on this I do believe it's lower than seven percent in the U.S.

30:28Jeannette:in terms of how many women are able to raise but I wonder if a part of why a lot of women don't raise is because they have the idea that it's not viable and so they don't even look into it I know at least that is a part of it. But the second part of it is just the fact that people don't like pitching. So not just women, but there's probably all kinds of businesses that have been raised because they don't like pitching. They don't like being told no. And on average, I think you're going to get at least 100 no's before you get a yes in the venture game. In what we do, pitching for corporate contracts, you may get thousands.

31:01Jeannette:It just depends. And so people don't like rejection. There's a book called Rejection Proof that's really good for anyone listening that struggles with rejection. But yeah, so I basically just told them set bigger goals, ask more and don't waste a meeting. So when you have a meeting, ask them, hey, are you interested in this? Let me tell you what I have going on. Do you or anyone you know, have any interest in doing this? Because there are ways to find accredited investors and you can direct pitch for them.

31:27Ashley Kirkwood:Yeah, absolutely. And that's a really clever way of doing it. Do you know anyone who it's almost an elegant way of asking for the deal without asking for the deal so you know it's I think it's a really top top tip and it does go full circle in terms of selling the product you're also selling you know you as a you as a founder your concept raising capital so the principles are very similar but I think you're right there's a combination of things around mindset around confidence around pitching um around um practice you know practice the more you do the more like more like better you'll get

32:01Jeannette:in rolodex if you don't know like if you don't know the people you may not be as comfortable and then there are there is still some bias of people being like is a female founder going to be able to get this done i think now we have the example of canva we have other amazing example of unicorn companies that were founded by women but there is still that pre-judgment of will she get this done because there were people who passed on great great investment opportunities who now probably are kicking themselves.

32:29Ashley Kirkwood:Yeah, there's a divine justice in some of that sometimes, isn't there? Amazing. So just coming to some final questions, Ashley, you'll have had loads of great advice over the years. Can you think of any standout advice that's really helped you personally or professionally all these years?

32:45Jeannette:Yeah, so my dad, he's also an entrepreneur and did really well in business. And it's one of my biggest supporters. And just I am a big fan of my my dad and my mom. But one thing my dad told me that stuck with me for my whole life is they cannot give you a no, they're just not the right person to give you a yes. Like don't give up when someone says no, like really helping me to understand that rejection isn't permanent.

33:08Ashley Kirkwood:Yeah, and it may be a not right now or one step closer to a yes, you can learn from the no, right? Yeah, great advice from your dad. Perfect. And then obviously, that's been an absolute key thing for the business that you've built so amazing good advice and Ashley if you could describe this year in one word what would it be and why?

33:27Jeannette:Growth we've just grown a lot this year grown the team grown the business our clients have grown astronomically they literally come in they come in one way sometimes they come in shy or like oh I really like Ashley blah blah blah and by the end of the year they're like I really like me okay like I am I am on top of the world And I love that for them. I often tell them, whoever I meet, when you first start working with me, I guarantee you in 12 months, I'm going to meet the real you. That's a lot of what we do is we allow people to be OK being themselves, being speaking up and going after what they really want and speaking their true desire, not the one that was given to them by societal norms and pressures.

34:07Ashley Kirkwood:And I love that as well, because at the end of the day, you know, it's not really what we get is who we become on the journey. I think that's so important as well because that's where the magic really is, actually. So, yeah, amazing. And we have a Brave Bold Brilliant playlist, Ashley. And what track would we be adding to our playlist from you? What's a standout song for you that you'd dance around the kitchen to or last song before you die? What would it be?

34:33Jeannette:Probably Tasha Cobb and Nicki Minaj, I'm Getting Ready.

34:38Ashley Kirkwood:Why? Any particular memories that that song evokes for you?

34:42Jeannette:oh I love that song I listen to it every like when I we do live events and they're just a lot of work and they're a lot of fun but I'm always listening to that song before my pitches before the event just getting in the zone of all the things that God is going to do and so I love that

34:55Ashley Kirkwood:song amazing we will add that to the playlist and Ashley brave bold brilliant what does that mean to you when you hear that what is it brave bold brilliant what does that mean to you

35:07Jeannette:I think it means once you are brave, a sign of bravery is boldness and a sign of you being bold. You should be bold about what you're brilliant about.

35:18Ashley Kirkwood:Yeah. Amazing. Thank you so much, Ashley. It's been a real pleasure and I'm so excited for you in the business and everything that's to come as well. So yeah, keep, keep shining your light bright.

35:28Jeannette:Definitely. And if anyone wants to find me, you can definitely join our school group. It's called Speak Your Way to Cash and we'd love

35:33Ashley Kirkwood:to have you it's a free group excellent we'll put that in the show notes ashley so everyone can find you wonderful great stuff all right then thank you so much ashley appreciate it thank you so i'd just like to say a big thank you to ashley for sharing her incredible journey from corporate law to building a multi-million dollar business that empowers others to lead speak and serve with confidence you know it's a powerful reminder to all of us isn't it that faith or authenticity and courage they're not just personal values they're actual business superpowers and for all of you listening if you're ready to step into your own boldness and scale your success i would absolutely love to support you and at brave bold brilliant we work with entrepreneurs with executives and business leaders to really accelerate growth make brave moves and achieve results that last so if you've been inspired by today's episode take action reach out to us connect with me we're here to help and start building a business and life that truly is brave bold and brilliant so until next time keep leading with courage and with confidence and just remember it is by being brave and bold that you will unlock your brilliant