From Courtroom To Coaching

We trace Sally Holder’s path from law to leadership to coaching, and we examine why true success blends income with lifestyle. We share a practical playbook for women founders who want speed, clarity, and freedom without burning out.

• early pull toward entrepreneurship and first wins
• law career highlights and lack of fulfillment
• pivot to COO roles across multiple companies
• coaching origin and focus on women founders
• why women need a different growth playbook
• aligning revenue goals with lifestyle goals
• systems that create speed and sustainability
• the value of help, mentorship and coaching
• simple planning over trial-and-error
• mindset shifts from black-and-white to gray

Chapters

• 0:00 Welcome And Guest Introduction
• 3:38 Early Signs Of An Entrepreneur
• 5:28 Law Career And Unmet Fulfillment
• 8:11 Jumping To COO And Operations
• 11:50 Becoming A Coach For Women Founders
• 15:45 Why Women Need A Different Playbook
• 18:22 Corporate Versus Entrepreneur Mindsets
• 18:49 Note: All timestamps within 1150 seconds

Transcript

SPEAKER_00: 0:00

Welcome to Weekly Wise Women Entrepreneurs Podcast, sponsored by barefitmarker.com, where we have been putting entrepreneurs online since 2012. My name is Constance Andrew. I am the executive producer and host of your show. And with me tonight, I'm very excited to have Sally Holder. Sally is the founder and CEO of the brand. I'm very interested to see what that's going to be all about. Sally, a green Greenville, South Carolina native, and founder. Realize and ultimately achieve her true potential. Sally's expertise does not something like mentoring business owners. Her unique background qualifies her as one of the most distinctive creative business coaches in the field. Creator degree business coaching community for female entrepreneurs. Sally graduated from Canberra Gill University in human and organizational development. During her 10-year law career, she served as the chief operating officer for six different companies. Dynamic, engaging, and passion are in many ways to describe Sally as a leader. She has the uncanny ability to uncover the real things holding business owners back. Even when they may not be aware of them themselves. She can pinpoint hurdles specific to each client and provide practical training and realistic steps to overcome them. Her unmatched holistic coaching style has fostered a resilient and engaged community of like-minded entrepreneurs to help empower each other. Throughout her career, Sally has received received various achievements and happily. In 2016, Sally was awarded the Jumpstart Award for helping the highest number of people successfully launch their business during the fiscal year. And in 2021, she was named one of USA Business Reports Women of Influence. Also in 2021, QSA Today named Sally's book, Hitting Rock Middle. One of the top-rated books that will change your life and business. In her free time, you can find Sally spending time with her two children. Edward 14, Catherine 11, and twin sister. Very interesting. Stacey, Hamden Clothing in Charleston, South Carolina. And spoiling her beloved chocolate land chewy Aussie Doodle sugar. Again, thank you so much for being here with us tonight.

SPEAKER_01: 3:06

Oh thank you for having me, Constance. I'm excited to be here and delighted to share what I know.

SPEAKER_00: 3:14

I have a feeling you know a lot. As an entrepreneur, CEO, and author, where would you like to start? Would you like to start with as a serial entrepreneur? So tell us a little bit about truthfully. Just tell us about who you are. Kind of walk us on your journey.

SPEAKER_01: 3:40

Sure. Well, I always say I had a passion for entrepreneurship. I should have known that I was meant to be an entrepreneur when I was doing a limited stand religiously at the end of our driveway every weekend, obsessed with perfecting, right? The recipe and getting more customers and what drove traffic and all of those lovely things. But unfortunately, that was not my path. I started out, like you mentioned, as an attorney. I thought that was what the idea of success was, right? It was me in a suit and hearing a briefcase and going to the office. So that's what I created, and I practiced labor and employment litigation, as you said, and had the pleasure of working with some amazing clients, but I never felt that sense of fulfillment. You know, I always say to clients, I really learned the hard way that there are two things that must always be present for us to achieve fulfillment, which in my mind truly is the epitome of success. And that is that it has to come with the achievement of your lifestyle goals as well as your financial goals. And obviously, lifestyle goals have has to include a lot for many female entrepreneurs, or many women just in general, that that comes with a lot more freedom and flexibility than I was ever able to achieve while I was practicing law. And so I wanted more control over my career and my life once I had kids. And you know, unfortunately, that's just not um something that really is achievable or wasn't at the time in my law practice. So I had an opportunity to go run a corporate impact firm. So when I was offered that chance to be their COO, I jumped at it. I thought this was my way out of law, and no matter what, I'm just gonna take it so I can figure out the world from there. And it was a great experience of you know, on-the-job training of how to run a company. The owner of the firm actually then had a commercial real estate company as well. So once I, you know, proved myself in his law firm, I was able to take over as the COO of his real estate company. So, you know, again, some great on-the-job training and learning all about drafting leases and you know, managing reconciling accounts, managing your QuickBook accounts, all of those lovely things. And so I found myself in that kind of serial COO role, switching from industry to industry. So I did six different companies in about seven years. And then I had lovely friends, kind of acquaintance of mine come and say, Hey, we can't afford to bring you on full-time, but we would love for you to coach us. And I said, uh, that's not something I've ever really thought about. So it really fell naturally into this coaching role. I started coaching them on, you know, some different aspects of their business, reviewing their financials, talking about revenue growth, and just really said, Oh my gosh, this is it. This is what I've been meant, you know, been practicing all these years to do is to work with female entrepreneurs. And now that's what I get to do day in, day out. And it's such a joy. I really focus entirely on a female entrepreneur. You know, I'm really passionate about the fact that we've been given the playbook that men have had for many years and told just to adopt what they've been doing. And I think that we as women have, you know, uh, we're different, right? And we need a different playbook. So I've been um steadily working to create that methodology, and and now that's what I teach inside my coaching program at the Broom. So that was a little bit of a long version of where I've come from and where I am today.

SPEAKER_00: 7:57

I actually want to ask you something, Sally, because you've been an attorney and working in law firms. I worked in a top tier law firm myself in New York City litigation support. And it was pretty common in the peers that you're talking about like we talked about different companies. I know it was pretty common in our tech world. Like I know that I would make a company for like 2020, right? But I wanted to ask you what you felt or what you feel is the biggest difference that you see between like working with miners and working with entrepreneurs.

SPEAKER_01: 8:44

Oh gosh. You know, I've never been asked that question in all the podcast interviews, so good for you. Um I would definitely say the biggest difference is you know, uh, I think entrepreneurs are visionaries at the end of the day, and attorneys operate in a very black and white world. And I have always believed that the world has a lot more gray than the legal world really will allow you to be able to do that.

SPEAKER_00: 9:29

Um right now, yeah. Right. Now one of the radio. I don't want to do anything. Um, I think you could have three.

SPEAKER_01: 11:54

Uh one another. Um I don't care for each other. Um I would like to have three years and really have only good money actually representing the room and I can't have that. I am gonna take a little bit of a beyond it is the word and have to be run by that number. If we're not shooting for seven years, we're not gonna invest and at least you can't do it. Freedom and flexibility that you're gonna do.

unknown: 14:29

You know, kind of and that's not what I want. I want to try not to work along the back. You have to do that. You have to put out the world.

SPEAKER_01: 14:40

And now it's a real company and colonize that on where it was. And like, you know, you have real quite critical because I know why. You know, it's all about the gas and that's good. Um, we're gonna keep it high with close back. You would never tell you. So, you know, like I said, you know, you know, you wouldn't think about it. Um, we could go for another mile. Well, you're looking for the next hundred miles. Um, and the product you just took to terrifying.

SPEAKER_00: 16:09

Oh kind of happen to go in an out and remind a little bit using the same skills tools and helps me get to a certain point.

SPEAKER_01: 16:24

I keep doing a single thing. You know, in looking at the eye or what it is that women were doing are they recognized really teller people that they're like three personality. And a totally thought about what my dreams are and who I am as an individual, and that's what I would do within that revenue accelerator program. I do much better on my clients that think of me as the test and so I think you know I'm gonna plant my flags when I'm done and eventually get there. Maybe so about myself, but and I'm I'm very shot in the dark about my super hard.

SPEAKER_00: 17:07

Or you can leave here. And I'm preparing you. But then you can jump. Well, I really do like faster, more economical, or gas-saving vehicles and go much faster to the destination because I know the route. A lot of times they don't even have business plans.

SPEAKER_01: 17:29

That is what I encourage more female entrepreneurs to do, but even for very high cooking. And um I mean other people have been there and they know exactly the tools have skilled that to accelerate and growth. You know, they there is no regularly learning. And they've grappled with that concept. Let's keep an idea. But when I no one's coming with a crown to anoint you and be like, you did amazing because you did it all by yourself, right? And women really are hesitant to get help and support, right? It's just like hiring, you know, a nanny or hiring someone to clean your home. Oftentimes women don't want the help because we're afraid it will have a bad reflection ultimately on us. And you can see that showing up in so many other arenas. Well, it's naive to think it wouldn't show up as well in our business mindset, too. Because it does. And that's why I say too all the time we have to have a someone, a coach, right, that says, hey, we get it. There are different hurdles, there are different trap doors that you're gonna fall into that then don't. And it's because society has told you, hey, don't get help, right? Be the superwoman, and you can only get your reward if you can.