Ashley Rector is a former attorney turned entrepreneur, the founder of Quimby Digital and the visionary behind Wimbly Social, a forthcoming AI-powered SaaS platform built to revolutionize organic social media strategy.
Ashley launched Quimby Digital to help purpose-driven brands scale their impact through smarter social storytelling. Under her leadership, Quimby has become known for delivering high-performing content and strategy across platforms like Reddit, Instagram, and TikTok—especially for clients in the health, wellness, parenting, and climate spaces.
With over a decade of experience spanning law, publishing, and marketing, Ashley brings a uniquely strategic and human-centered approach to tech innovation. Her newest venture, Wimbly Social, aims to replace the guesswork of social media with a platform that blends AI-powered ideation, scheduling, and analytics.
Ashley is also a mother of two, an advocate for mental health, and a believer in building businesses that are both profitable and people-first.
What is your typical day, and how do you make it productive?
I’m up by 6:30 thanks to two tiny alarm clocks—my kids. Mornings are for them and for me: breakfast, school drop-off, and a quick workout if I can swing it. My workday starts around 9:30, and I dive straight into strategy or sales. I frontload my day with the deep work that actually moves the business forward—writing proposals, mapping strategy for clients, or pushing Wimbly Social’s product roadmap.
I block time religiously and protect my calendar like it’s Fort Knox. No unnecessary meetings, and every to-do lives inside ClickUp. My team knows I’m obsessive about priorities—if it’s not revenue-generating or client-facing, it’s likely getting delegated or deleted.
Afternoons are for calls, team check-ins, and the inevitable fire drills. Evenings are for dinner with my family, a glass of wine if it’s that kind of day, and sometimes a little laptop catch-up once the house is quiet again. I don’t aim for balance; I aim for rhythm. Some days are chaos, some are magic—but the goal is always progress.
How do you bring ideas to life?
If I can’t shake an idea for a month—or in the case of Wimbly Social, two years—I know it’s one I have to bring to life. I don’t chase every spark. I let ideas simmer. If they’re still haunting me after the initial excitement fades, they’re worth pursuing.
Once I know it’s real, I build a rough framework: What problem is this solving? Who is it for? Can it make money without burning me out? From there, I move fast—mapping it in ClickUp, talking it out with my team, breaking it into action steps. I’m not precious about perfection. I’d rather build and iterate than daydream forever.
Some of my best ideas started as scribbles in my Notes app that refused to leave me alone.
What’s one trend that excites you?
Brands finally waking up to Reddit. For years, it’s been treated like the weird cousin of social media—too unpredictable, too raw. But now, smart brands are realizing that Reddit isn’t just a community platform—it’s an influence engine.
People trust Reddit threads more than polished ads. It’s where purchase decisions actually happen, where SEO is being shaped in real time, and where AI models like ChatGPT are pulling their insights.
I’m especially excited because we’ve been ahead of the curve at Quimby. We’ve been building Reddit strategies for clients while most agencies were still asking, “Wait… can we even be on Reddit?” The brands that learn to show up there with honesty and value—not just marketing fluff—are going to win the long game.
What is one habit that helps you be productive?
If something can be done in under two minutes, I just do it. I don’t add it to a to-do list, I don’t “circle back”—I just knock it out. It keeps the little things from piling up and mentally cluttering my day.
That one habit has saved me from drowning in digital sticky notes and pretending I’ll remember later. Spoiler: I won’t. Fast execution on small tasks keeps the runway clear for the big stuff that actually moves the business forward.
What advice would you give your younger self?
Stop trying to make everyone comfortable. That includes clients, colleagues, and your own inner critic. Discomfort is where the good stuff lives—growth, clarity, momentum.
Also: You don’t need more credentials. You need more reps. You already know enough to start.
Oh, and rest isn’t earned. It’s required. Burnout doesn’t make you a badass—it just makes everything harder.
Tell us something you believe almost nobody agrees with you.
Organic social is more powerful than paid advertising.
Most marketers look at me like I’ve grown a second head when I say that. But here’s the deal: paid can buy you reach, sure—but organic builds belief. It’s where trust is earned, stories are told, and brand affinity is actually built.
Paid is rented space. Organic is owned influence. And when done right, organic content outperforms ads in ways performance marketers can’t always quantify—but your customers feel it.
If your organic presence is an afterthought, your paid strategy is running on fumes.
What is the one thing you repeatedly do and recommend everyone else do?
Prioritize your mental health—ruthlessly and without apology.
Nothing can prepare you for what happens when you lose it. Trust me, I know. When your brain isn’t functioning, nothing else matters. Not your goals, not your calendar, not your ambition.
I build mental health into the foundation of how I run my life and my business. That means boundaries, rest, therapy, and choosing peace over people-pleasing. It’s not soft. It’s survival—and the smartest strategy I’ve got.
When you feel overwhelmed or unfocused, what do you do?
I step away from the screen, put my feet in the grass, and play with my kids.
It sounds simple, but it resets everything. They pull me out of my head and back into the present. No Slack pings, no to-do lists—just sidewalk chalk, giggles, and the reminder that none of this is that deep.
Nature and noise from tiny humans—way more effective than any productivity hack.
What is one strategy that has helped you grow your business or advance in your career?
I networked my ass off and gave advice with zero gatekeeping.
Every client, collaborator, and opportunity came from showing up, sharing what I know, and not hoarding information like it’s a trade secret. I didn’t wait to be the biggest voice in the room—I just made sure mine was helpful.
When you lead with value, people remember. When you follow up, they trust you. And when you do both consistently, doors open that no cold pitch ever could.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
For a while, I took my eye off the financials. I was focused on growth, team culture, client wins—all the shiny things. But revenue without margin is a trap, and I learned that the hard way.
The turning point was realizing I didn’t need to be the CFO—I just needed to build a team that had financial rigor baked in. I brought on people who think in spreadsheets and question every expense. Game changer.
The lesson? Vision is great. But cash flow is oxygen. Watch it—or you’ll find yourself sprinting with no air.
What is one business idea you’re willing to give away to our readers?
If you’re savvy with words and understand how ChatGPT works, build a prompt library. Seriously.
Most people have no idea how to ask AI the right questions—and they’re desperate for shortcuts that save time and actually get results. Package up smart prompts by niche (real estate, marketing, HR, whatever), put it behind a paywall, and charge a low monthly fee.
It’s low overhead, high demand, and easy to scale if you keep it updated. You don’t need to code anything fancy—just deliver value consistently.
What is one piece of software that helps you be productive? How do you use it?
ClickUp—religiously.
Our entire team lives in it. Client deadlines, internal to-dos, creative workflows, launch plans—if it’s not in ClickUp, it doesn’t exist.
It keeps us moving fast without dropping balls. I use it to assign tasks, set priorities, track progress, and make sure everyone knows what’s next. It’s basically our second brain—and way more organized than my first one.
What is the best $100 you recently spent?
I’m a sucker for a good meal, so hands down—a dinner out with my husband at a tiny, no-frills Italian spot. No kids, no laptops, just pasta, and conversation that didn’t involve a calendar.
Do you have a favorite book or podcast from which you’ve received much value?
Big Magic by Elizabeth Gilbert has been a north star for me—especially when I’m stuck creatively or second-guessing myself. It reframed fear as something you bring along for the ride, not something that gets to drive.
On the podcast side, Manifestation Babe’s Sovereign Money series really hit. It pushed me to rethink my relationship with money—not just in business, but in how I value my time, energy, and ideas.
Both reminded me that intuition is a business tool, and creativity and money don’t have to be at odds.
What’s a movie or series you recently enjoyed and why?
I finally jumped on the Fourth Wing series and tore through all three books in two weeks. Total escape, zero regrets.
It had everything I love—high stakes, sharp banter, strong female lead, dragons (obviously), and just enough spice to keep it interesting. It was the exact mental break I needed from spreadsheets and Slack notifications. 10/10 would recommend for anyone who wants to disappear into another world for a bit.
Key learnings:
- Build fast, refine later—if an idea sticks with you, it’s worth pursuing, even if it starts messy.
- Protect your mental health like your business depends on it—because it does.
- Organic content isn’t dead; it’s just underleveraged. Trust is built, not bought.
- Surround yourself with people who challenge your blind spots, especially when it comes to money.
- Lead with value, share what you know, and don’t gatekeep—opportunities follow generosity.