Fall is here and I am feeling hopeful. Hopeful about how this year ends and what 2026 will bring. My, how long it took to get here.

Newsletter Sounds: a few tracks that carried me through September. Listen here while you read.

My word for October? Hope.

There are aspects of my journey that are still uncertain. Yet that isn’t stopping the hope that’s building. That’s all I’ll say for now :)

September was filled with the kind of momentum I’d been waiting to see.

September began with preparing for the 8th Annual SIS Summit. This year’s theme, Revenue Reimagined, drew a crowd of about 600 attendees. I talked about this partnership a bit last month, and September was where the rubber met the road; making sure the Reverse Pitch, sponsored by ADP, was excellent. It was the first of its kind at the conference, and I had the opportunity to both produce and moderate it.

Maybe you’re wondering what it took to produce a segment at a conference that size. Here are some of the things I considered:

Once that was clear, it was time to assemble the humans who would make it all happen. The SIS team selected wonderful judges and experts, and it was my turn to find founders to pitch on stage.

Where did I go? Knowing where founders are and where they take in content helped a lot. I leaned on networks I’m part of and the community I’m building on Threads. That call for founders alone got 1,800 views.

Since there were no cash prizes or credits, I focused on the caliber of people in the room. Money matters, but connection and access do too. Sales professionals from OpenAI, Pinterest, and Netflix were in attendance. I pitched founders on the value of that exposure and feedback.

And guess what? The lack of cash prizes didn’t stop interest. Founders valued the chance to tell their story and be discovered. I balanced two experiences:

I also made sure everyone, founders and judges alike, understood the logistics and expectations. When people know what’s expected, they can show up fully.

All of that prep led to a session where everyone was engaged, curious, and excited to connect.

Huge thanks to Chantel George and the SIS team for the opportunity.

This experience reminded me that I want to be on more stages in 2026 (and yes, the rest of 2025 too). So if you have suggestions for stages I should be on as a speaker, moderator, host, or segment producer, send them my way.

September also marked the start of onboarding with a founder in the fashion space (yayyy). I’m learning so much from their leadership and look forward to sharing what I can.

Part of what makes me a great content creator is that I’m still a practitioner in this space. It helps me connect past experiences to what I share here and on other platforms with the nuance that’s often missing in modern business advice.

This month also got me thinking about my current and future offerings. For example, I offer a 2-hour session that started as a product audit. After working with a few founders in this format, it’s become so much more. Two hours is plenty of time to get unstuck, whether it’s redefining a user problem, strategizing, or drafting a survey. These sessions have become a real catalyst for founders and a low-lift way to get to know my work.

For me, they’ve been a great way to test theory against reality and see what’s possible in a short burst of focused time.

Here’s to more of these sessions. Also, pricing goes up November 1, so if you know a founder who could benefit, send them my way.

Another avenue that’s opening up? Community. More on that below.

September ended with an announcement I had been sitting on for a while, the launch of my weekly LinkedIn show, Startup Baddie Live!

Every Friday at 12 PM EST on LinkedIn, because founders deserve better Fridays and better advice.

The show isn’t about theory or hustle culture. It’s about helping founders think critically about how to apply ideas to what they’re building.

Why go live? Because you have to find what works for you. I’ve always said that content is the new résumé, and I believe that. But if creating content feels dreadful, you’ll never be consistent.

That’s where I was with pre-recorded content. I’m great on video, it brings out me, but pre-recording made me stiff. I focused too much on being perfect instead of being present.

So I asked myself how I could remove the mental barrier. Going live was the answer. I did my first LinkedIn Live back in May 2025 and loved it. The third-party platform I use lets me save the audio and video, so I can repurpose the content to YouTube, Spotify, and Apple. Win.

As I write this, the lives are well underway. Below is the rest of October’s lineup. Visit [this post] to RSVP.

What does upskilling corporate workforces or larger brands in deploying community look like?

And how can I play a part?

As I mentioned earlier, I’ve been exploring how to expand on what I’ve learned about building and activating community. For a variety of reasons, that may look like bringing workshops to the corporate world.

More to come. This one’s still developing.

I’m dreaming about stages. Fun activations at SXSW and Cannes Lions. My ideal mix of client work and content. Stability. Growth.

Setting myself up for success in 2026.

This month was podcast-heavy, and both episodes I loved came from Aspire by Emma Grede.

Episode: The Aspire Playbook: How Allison Ellsworth Turned a Kitchen Experiment into a Billion Dollar Brand

What I loved: Allison talks about the early days of Poppi, which actually started under a completely different name and brand (Mother Beverage). She experimented in her kitchen to really understand what she was creating. That reminded me how valuable it is to immerse yourself in the problem and process. It’s how you catch nuances that AI or third parties can’t. I also loved hearing about their rebrand journey and what they considered along the way.

Episode: The Aspire Playbook: Mark Cuban’s Day-1 Blueprint for Startup Success and How AI is Changing Entrepreneurship Forever

What I loved: This was the first time I had heard Mark Cuban’s full story. Hearing his journey made me realize that what I, and so many other founders, experience isn’t unusual. We’ve just stopped talking about the messy middle and started glorifying outcomes. Focusing only on the end result can make the process feel unbearable. His story was a good reminder that the chaos and uncertainty are part of it.

Whether you’re looking for a thought partner, a fresh perspective, or someone to help you get unstuck, here’s how I currently support folks:

If something here speaks to you (or someone you know), I’d love to hear from you.

If you made it this far, thank you. Hit reply and let me know what landed (or what you want more of next time. I’d love to hear from you.

Grateful you’re here. Talk soon.

xx,

Ashley

Startup Baddie