100 | What 1 Year, 1 Rebrand, and 89% Down Taught Me About Leadership

Are you holding it all together while quietly falling apart?

In this raw and radically honest milestone episode, Dawn Andrews peels back the curtain and shares what it really took to hit 100 episodes—while living through the most unrelenting year of her life. We're talking an 89% business drop, a full rebrand, marathon training, eldercare chaos, and teen parenting drama. 

This is not your tidy “12 leadership tips” post. It’s a masterclass in what leadership looks like when you're building in the middle of the storm.

If you’ve ever felt like you’re barely holding it together behind the scenes while trying to lead with grace in public—this one’s for you.

Key Takeaways

• Real leadership doesn’t look perfect. It looks like showing up in fuzzy robes, uncertain, but present.
• Visibility isn’t about performance—it's about truth. You can’t teach leadership from behind the curtain.
• Delegation without clarity is just stress disguised as progress. The turning point? Simple systems and clear ownership.
• AI isn’t therapy—but it can save your sanity. When life fell apart, ChatGPT became a midnight thought partner.
• Letting go isn’t a moment. It’s a muscle. Personal and professional transformation require daily, messy, imperfect release.

Resources & Links

• AI for Founders Community
• 10 Ways AI Will Make You a Better Leader – Free Guide
  
  

Related Episodes

• Episode 68 – 10 AI Tools That Save You 60 Hours a Month
  Dive deeper into how AI isn’t just a novelty—it became my midnight coach during the year everything went sideways. This episode lays the foundation for why systems, tools, and automation matter.
• Episode 64 – She’s That Founder: A New Beginning for Us All
  When I pulled the trigger on the rebrand from My Good Woman to She’s That Founder, this episode chronicles that turning point. If you’re riding change, it’s a must‑listen.
• Episode 67 – Command the Room: Female Leadership Secrets Unlocked with Samara Bay
  The moment where visibility, voice and stepping up fully landed. Perfect complement to the mess‑and‑mission of Episode 100.

Want to increase revenue and impact? Listen to “She's That Founder” for insights on business strategy and female leadership to scale your business. Each episode offers advice on effective communication, team building, and management. Learn to master routines and systems to boost productivity and prevent burnout. Our delegation tips and business consulting will advance your executive leadership skills and presence.

Transcript

She's That Founder
100 | What 1 Year, 1 Rebrand, and 89% Down Taught Me About Leadership

Episode 100 and I almost didn't record it because I need to tell you the truth about what it took to get here. 

Not the highlight reel, not the polished lessons, not the 12 things I learned about leadership, the real story, the one where I recorded episodes, well, my life was falling apart. The one where I asked women to step into leadership while I was barely holding myself together. The one where I learned that you can't teach courage well without being courageous yourself. 

So if you're here for the tidy version, this might not be that episode, but if you're here for the truth, buckle up.

Hey, hey, hey. You're listening to She's That Founder, the show that helps ambitious women stop drowning in decisions and start owning their CEO seat with a little bit of AI magic.

I'm Dawn Andrews, and today, well, today is different. Today we're talking about what it actually takes to show up, not just in business, in life. This episode isn't structured quite like the others. No numbered lessons, no action steps. No, your move at the end. Just three real vulnerable confessions about what these 100 episodes of this podcast have taught me.

I thought I could help women lead without being fully visible myself. I didn't think I was hiding, but oh boy was I, I thought I was good at letting go. I gave away everything I possibly could. I love some free time. I really wanted to be, I wanted to delegate. I thought I was delegating, but I just didn't know how to set anyone else up truly for success. And finally, I'm exhausted. I'm recovering and I'm still here. And that might be the only lesson that matters. 

So let's go. Confession number one, I thought I could help women lead and lead well without being fully visible myself. 

So this is where it all started. Let me take you back to episode one of my Good woman, the OG podcast. 5:00 AM I couldn't sleep any longer. I was in my office wrapped in my oversized gray fuzzy robe. I think it, it's, it's actually Frank's robe. But truth be told, I actually fit into it better than he does at this point. Menopause has got me, I look like a giant seal, sitting in an ergonomic chair wearing Adidas slides and a messy bun with socks with the door open recording in my office.

I sat into the microphone. This is episode one of my new leadership podcast, and I'm terrified. It feels like I'm pretending with this big ass microphone tucked into my face Still, I'm doing it anyway because I believe we need more women in leadership. 

I told the story of buying a yellow motorcycle, a moto Guzzi named Iris, which we just recently unearthed in a really interesting location. I'll tell you about that in a moment. I talked about how I went from riding on the back of someone else's bike, staring into the back of a leather jacket, to sitting in the driver's seat with an unobstructed view of everything. 

That motorcycle was a catalyst for my confidence, and I wanted this podcast to be the same thing for other women. I shared that I dream of a world where 51% of the world's governments are led by women. C-suite positions held by women, businesses, small and large, owned and operated by women. A big vision, a beautiful mission. Inspiring, uplifting. I genuinely want to help other women, but here's what I didn't see at the time.

I was staying safe behind the scenes, behind my microphone. Not in some dramatic self-protective way. I didn't feel like I was hiding, but I was because my Good Woman was broad enough that I could help everyone without claiming anything specific for myself. I could teach visibility without being too visible. I could talk about leadership without fully stepping into it, and here's where it showed up in ways that I didn't even realize. 

I worried about being put together, about always looking perfect on camera when I was recording. So much so that sometimes I would just record without, um, without video, and even to this day to just continue to out myself. I have video for every single one of these podcasts, not one of which has been posted. Mm-hmm. I was also worried about my space being Instagram perfect. My desk tidy and designer are pretty, and I can tell you none of those are true. And there is a reason there's a green screen behind me right now. You know that quote, how you do anything is how you do everything.

Yeah, that's a quote that has been important to me in my life, but it was haunting me because if my office wasn't perfect, what did that say about me? If my life looked messy? Could I still teach leadership? If people saw the real me, not the polished version, would they still listen?

But here's what I figured out. 

What I figured out is that quote is bullshit. At least it's incomplete. Because if it were really true that how you do anything is how you do everything, then every messy desk would equal a messy business. Every imperfect morning would equal an imperfect day for that leader, and every human moment would disqualify us from being exceptional.

And that is just not leadership. That is perfectionism dressed up as wisdom and the real truth. How you show up when things are messy. That's how you do everything. When you are at your worst, when you are drained, when you feel like you got nothing left, how you show up tells you more about who you are as a leader than anything else.

But I was still staying vague. I stayed broad. I stayed safe for 63 episodes. I showed up as My Good Woman, and I had big, gorgeous, amazing conversations with incredible female leaders. I talked about advancing women building community, finding your voice, and it was good. The show was good, but it wasn't landing, not in the way I wanted it to.

It wasn't getting momentum. I was getting downloads, but not transformation. I was reaching people but not really moving them, and that was a do or die moment in these a hundred episodes. It was either get coaching or give it up. 

So I got coaching and I started working with some amazing people. And the question that we kept circling back to about My Good Woman was, who is this really for? And I'd share long-winded. Esoteric answers and they would respond. That's still pretty broad. Can you identify one specific person and Not even intentionally. I would resist. I would dodge, I would overthink, but there are so many types of women, so many types of leaders, so many leadership situations that I wanted to speak to. And finally, my coach just said, let's try this. Just describe one woman you're picturing when you write your episodes.

Still nothing. We went back and forth for weeks, different angles, different approaches, different questions, and then slowly over time. In fact, it took almost six months because there was not a lightning bolt moment. 

But through iteration, my ideal listeners started to come into focus, a female founder running a service-based business, a Million dollars in revenue, brilliant at her craft, drowning in operations, doing everything herself, and afraid to let go. I could see her because I was her. 

This was all just one big exercise and holding a mirror up to myself, and even after I got clear on who she was, I still was hesitating because committing meant letting go of My Good Woman. It meant going all in on something truly specific, and it meant claiming a lane and claiming a lane meant being seen, not visible in the abstract way I've been teaching, but actually seen for who I was, what I did, what I stood for, and it took even more conversations with my coach, with my team, with myself before I finally said it out loud.

And you know what? As I share this to you guys, this is gonna seem so ridiculously like, duh, of course. But I said, I'm focusing on AI for leaders, female founders who need to scale. That's who this is for. Yeah, it was like a wrestling match to get there, which is something I'm apparently fond of I'll tell you more about that in a minute too. 

So while I was. Working on My Good Woman and working on this rebrand. I was training for a marathon I was running towards something, but I honestly wasn't even sure what it was. Episode 64 was our relaunch. I announced that My Good Woman was becoming, she's that founder, and I was again, terrified.

Not because the name was wrong. Because it was right for who I'm trying to serve and being right meant I couldn't hide behind the broad mission anymore. And I also had to just choose and go. I was afraid of niching down. 

But what I was really afraid of was this, that if I got specific, people would see me. Really see me. And what if I wasn't enough? What if my office wasn't perfect? What if my life was messy? What if I didn't have it all together? 

But here's what these a hundred episodes taught me. You can't help women step into leadership from behind the curtain, You can't teach visibility while staying vague. And you can't help women take the driver's seat if you're still trying to make everything look perfect before you just sit the fuck down in yours. The work isn't about being polished. It's about being real, and real means messy desks, uncertain days, and offices that aren't Instagram perfect and showing up anyway.

Okay, confession two. I thought I was pretty good at letting go. Look, I will find any way to not work. I am a champion at procrastination, and part of being excellent at procrastination is knowing exactly when to do the work and what work you should be doing. So if somebody else can do it, hand it off. But let me tell you about this year because it was a perfect storm, and I mean that quite literally. Everything everywhere, all at once.

In January, there were massive wildfires in the Los Angeles area, and we were on alert to evacuate our home of 26 years, twice.

Then in February, my mom had a health scare. The kind that makes you drop everything and realize that time is not infinite.

In March, I ran the LA Marathon, something that I trained a year for. 26.2 miles and I finished it, but I was also running a business, running a household, and running on fumes.

In April, my husband turned 60, we threw him a live concert party. We even had Keanu Reeves on the premises. How about that? It was beautiful, exhausting, and one more thing to plan, coordinate, and show up for all against the background of everything that was already happening.

In May, I found an apartment for my mom, yay, and moved her out of her home. The home I grew up in, my 83-year-old mom who identifies as a hoarder. Decades of belongings, overwhelming clutter, garbage bags, full of craft supplies and treasured household memories, commercial dumpsters, a shipping container's worth of fabric, delivered to a homeless charity and bedbugs. Don't forget the bedbugs.

For those of you that are runners or have run a marathon, you know about miles 20 to 22. And for those of you that don't, I'm gonna share with you, that is when you hit the wall, that's when your body says stop. Your mind says, quit that's where you break down. And in that particular marathon, a friend of mine was there and I broke down in his arms crying as he passed me forward and told me to keep going. 

And that's where I was in May when I was moving my mom. That was mile 22 for me. 

In June, my oldest son's high school graduation, and his 18th birthday milestone moments beautiful, heavy and bittersweet. And here's what nobody tells you about that transition. That is also a WWE wrestling match emotionally for 18 years, you're the one who's always needed, who's always driving the action. The one who fixes, decides, protects, guides, and then seemingly overnight, you're supposed to become the spectator, the mentor, and the guide from the sidelines.

My son looked at me after graduation, not with anger, but with observation, and he just said, mom, I've got this. And he does. He really does, but I didn't know how to let him, because letting go isn't just about trusting him. It's about releasing my identity. It's the person who was always needed. 

Who was I? If I wasn't driving the action, what was my role if I wasn't fixing things? And that shift from driver to passenger, from Fixer to Guide has been one of the hardest things I've done this year. I had no idea how hard letting go would be, and I am still doing it, and I always will be, because letting Go is in a one-time event. It's a practice, it's a daily choice and an ongoing release. 

And then in July, my youngest son turned 16. Another bittersweet milestone moment that was so lovely and wonderful and a capper on quite the beginning of a year, and somewhere in the middle of all that scattered across every month. My business was down 89%. Let that sink in for a second.

I was hemorrhaging revenue while training for a marathon, planning a party, moving my mother, navigating adolescence with my sons, and trying to show up every Tuesday and Thursday with a new podcast episode. 

Oh, and the podcast we had rebranded it. I took a long break and we relaunched it in May because apparently I thought, you know what? This dumpster fire of 2025 needs a complete rebrand. 

Here's what nobody tells you about being a female founder. You don't get to have one crisis at a time. It's never just business or family. It's always, and. Business and family and aging parents and teenagers and personal milestones and financial stress, and showing up and holding it all together, everything everywhere, all at once and through all of it, the chaos with my mom, the complexity with my kids, the weight of it all.

I was leaning on AI like crazy. Not just for business, but for everything because I needed help and I couldn't afford to fall apart. So I'd sit in my office sometimes at 3:00 AM and type, I'm overwhelmed. I don't know how to do this. Help me think this through and ChatGPT would respond with questions, with frameworks, with clarity. When my brain was fog, Was it therapy? No, not exactly. Was it coaching kind of. Was it helpful? Absolutely. 

And here's what I learned through all of it. I thought I was good at letting go because I wanted to delegate, but wanting to delegate and actually delegating are two completely different things because here's what I used to do I'd hand off something to my team and say, can you handle this? And then I'd wonder why it didn't get done or why it got done differently than I expected, or why they kept coming back to me with questions and I'd think. See, I can't delegate. They still need me. But the truth was I wasn't setting them up to succeed.

I was handing off tasks without context, without clarity, without systems, and I didn't really think it at the time, but I was clearly expecting them to read my mind to know what I meant by handle this to intuit the standards, the process, the outcome I was picturing. And when they couldn't, I would pull it back.

Oh my God, Dawn, why? Because I felt like it was easier to do it myself than to explain it. And girl, I know this sounds familiar to you. So here's what changed. This year I stopped trying to delegate tasks and started building bulletproof systems. Not fancy ones, not complicated workflows. Just simple, clear systems that answered three questions. What does success look like? What are the steps to get there? Who owns it? That's it. 

We started with the simple system, the simplest system possible, a Google spreadsheet task, who owns it? Status, simple columns. And we moved to Airtable and we iterated and we're still iterating and we always will be iterating because the system doesn't have to be perfect, it just has to exist.

And once it existed, everybody can improve it. Everybody can optimize it, everyone can make it better, but they couldn't improve anything that still lived in my head. 

And here's the hard part. I am learning the same lesson at home with my mom, with my sons, with my family. I can't do it all. I can't fix everything. I can't be the only one holding it together. We're navigating a stage of growing up with our sons that none of us saw coming. Not that we didn't see adolescence, everybody knows that adolescence is no joke, but parenting teenagers in this world at this time in the world is humbling in ways that I can't fully put into words.

There are conversations I'm having now that I never imagined I would need to have. Boundaries. I'm learning to hold. Decisions, I'm making without truly knowing if they're the right ones. And I'm learning to be clearer about what I need, what the boundaries are, what success looks like, and I'm learning that letting go doesn't mean just handing something off and hoping for the best. It means setting people up, giving them what they need, and being clear and then trusting them. 

That's the last part. That's the hardest because I still don't always know who will pick up the ball, but I'm learning that leadership isn't about knowing everything. It's about creating clarity so other people can step up and then getting out of their way, even when business is down 89%, even when you're moving your mother and planning parties and running marathons and navigating parenting and rebranding your podcast, especially then.

Confession three. Truly, I'm exhausted. I'm recovering, and I'm 100% still here. So here's where I am at episode 100. I'm tired. Some days I don't wanna get outta bed. Some days I nap in the middle of the day. Some days I stop working at 2:00 PM and stare at the TV for hours. Some weeks I don't even leave my house, and I'm not saying any of this for sympathy.

I'm saying it because it's the truth. I'm tired of pretending I have it all together. I'm tired of performing strength. When I feel fragile, I'm tired of worrying about whether my space looks Instagram perfect when I can barely keep my head above water. 

You don't finish a marathon because you're ready, you finish. You keep moving even when every part of you wants to stop. 

This year was supposed to be different. This was supposed to be the year that things clicked and instead everything happened at once. The business, my mom's health scare, joy, loss, growth, all of it. All of it at the same time. And there have been weeks where I didn't know if I could record another episode.

There have been moments where I've questioned whether any of this even matters. There have been days where showing up felt impossible, and I did it anyway, and I'm not sure if that's strength or stubbornness or some combination of both. 

But here's what I know right now in this world, female founders are carrying too much. We're building businesses while managing family crises. We're showing up for clients while navigating stages of parenting we never imagined. We're teaching leadership while figuring out how to lead ourselves through exhaustion.

We're trying to advance women while just trying to survive the week, and the truth is we're exhausted.

So I see you if you're holding too much right now. I see you. If you are trying to lead while barely holding it together and I see you, if you are building something beautiful while your personal life feels overwhelming, you are enough. That's what a hundred episodes has taught me. The showing up is the work, not the polished version, not the Instagram Perfect office, not the 12 lessons, just showing up when you're exhausted, when your life is messy, when your business is down, when you don't wanna get outta bed, when you're not sure what to say, because your people aren't looking for perfect. They're looking for real. They're looking for someone who says, I'm still figuring it out, and I am, and I'm still building and it's hard and I'm doing it anyway.

I didn't share this 100 episode story with you because I want you to think I'm strong. I'm telling you this because strength is not the goal. The goal is showing up, ugly, showing up when your office is a disaster and your business is down and you can't remember the last time you left your house.

That's not strength. It's survival, and survival is messy and unglamorous. And it's what builds the business that you actually want to lead. You don't have to have it all together. You just have to show up, messy, tired, and uncertain. Just show up anyway, that's leadership. That's what these 100 episodes have taught me. 

So thank you for being here. Thank you for being a listener. Thank you for whatever it is that you're building. This is episode 100 of She's That Founder. It is not the one I plan to record, not the one with the tidy lessons and action steps, but this is the one where I told you the truth.

This perfect storm of a year taught me more about leadership than any course or book or framework or training ever could. It taught me that you can't separate who you are at work from who you are at home. It taught me that showing up is not about being ready.

It's about showing up anyway, and it taught me that the work of transformation, real transformation happens in the mess, the birthdays, boundaries, bed bugs, marathon, and all of it. 

So here we are from episode one, terrified in a fuzzy robe, and dreaming of helping women take the driver's seat to episode 100. Still in a fuzzy robe, but no longer terrified, even when things aren't perfect, even when my life is sometimes a shit storm. Even when I'm using chat GPT instead of a therapist. I'm too tired to leave the house or when business is down and I'm barely holding on. Because you know what keeps me up at 3:00 AM not my business being down or the chaos or exhaustion. It's knowing that somewhere right now there's a woman who's brilliant, capable, and ready to lead, but she thinks she has to have it all figured out first, and she's waiting. 

This episode, these 100 episodes are for her. Because I'm too impatient to wait for her to feel ready. I need her in leadership now.

So if you're listening to this and you're tired, I love you. If you're holding too much, I love you. If your year has been a perfect storm, ooh girl, I'm hugging you and I love you. You don't have to have it figured out. Just show up and lead. Thank you for being here. For showing up, for trusting me through this rebrand, through this mess, and through all 100 episodes.

Whether you've been here since episode one, or you just found me today, you're exactly where you're supposed to be. And I'm so glad you are building something that matters and I'm honored to be part of your journey. 

So next episode, back to our regular programming. 

But for today, let's just sit here together in the truth of what it takes to show up. 100 episodes, a perfect storm of a year, a whole lot of mess, a whole lot of growth, and I'll see you next time. 

But until then, keep leading. Keep showing up. Keep becoming, especially when you're tired, even when it's everything everywhere, all at once. You've got this lovey.