We caught up with the brilliant and insightful Antoinette “Ajay” Kyle a few weeks ago and have shared our conversation below.

Antoinette “Ajay”, thanks for joining us, excited to have you contributing your stories and insights. So, let’s imagine that you were advising someone who wanted to start something similar to you and they asked you what you would do differently in the startup-process knowing what you know now. How would you respond?

Four years ago, I would’ve said I had no idea what I was doing nor where I was headed. Now, I know nothing happens by chance. My presence is intentional, my purpose undeniable. Every door I’ve walked through and every table I’ve sat at has taught me something—good, bad, or indifferent. The journey itself has been just as valuable as the goals I’ve crushed along the way.

I needed every pitfall and misstep because they aren’t just setbacks—they’re stepping stones. Each challenge has sharpened my instincts, refined my strategy, and given me the resilience required to operate at this level. Without the lessons from failure, I wouldn’t have the wisdom to navigate success. The obstacles weren’t detours; they were the necessary training ground for the heights I’m reaching now.

If I were starting over today, knowing everything I know now, I’d do three things differently— always bet on myself, protect my time, and invest in the right people and tools from day one.

1. Move with Strategy, Not Just Hustle
When I first started out, I was fueled by passion and hustle, but I didn’t always have a clear long-term strategy. Now, I understand that clarity and alignment are everything. I’d immediately define my niche, create a brand blueprint, and be intentional about my messaging, ensuring every move aligns with my core mission.

2. Protect My Time & Energy
Early on, I said yes to too many things—clients who weren’t the right fit, projects that drained me, and meetings that led nowhere. If I could do it over, I’d set clear boundaries from the start, charging my worth, choosing collaborations wisely, and focusing on high-impact work instead of trying to be everywhere at once. Exclusivity fuels demand.

3. Build a Stronger Infrastructure from Day One
Instead of figuring things out as I go, I’d immediately invest in systems, automation, and the right team. I now know that success isn’t about doing everything myself—it’s about delegation and leveraging the best tools to streamline processes. I’d also bring in legal and financial experts earlier to ensure the foundation is solid. I’d make a strong effort to network with people in positions I’d like to be in.

The Biggest Lesson? Confidence Over Perfection
I wasted too much time second-guessing instead of just doing. If I were starting over, I’d trust my instincts more, take bigger risks, and know that done is better than perfect. At the end of the day, the real key to success isn’t just knowing the game—it’s having the confidence to play it boldly.

Great, appreciate you sharing that with us. Before we ask you to share more of your insights, can you take a moment to introduce yourself and how you got to where you are today to our readers.

Miss Money Shot Media isn’t just a media company—it’s a movement. It’s proof that vision, grit, and purpose can create something bigger than a brand; they can build a legacy. What started as a side hustle, capturing moments through my lens, evolved into a full-scale digital powerhouse.

I didn’t just transition from photographer to CEO—I shattered ceilings, redefined the blueprint, and reclaimed the right to tell our stories on our own terms. Too often, Black women are told to wait for a seat at the table, to work twice as hard for half the recognition. I refused. I stopped waiting for doors to open and built my own.

Every frame I shoot, every campaign I design, and every strategy I craft is intentional — creating space for people and organizations that deserved to be seen, heard, and valued. Miss Money Shot Media isn’t just about content; it’s about culture. It’s about leveraging media as a tool for empowerment, for elevation, and for change.

My journey started in the heart of Five Points, where I spent eight years at Free Speech TV (FSTV), climbing from intern to National Broadcast Journalist, Producer, and ultimately, Digital Director. At FSTV, I soaked up knowledge from some of the sharpest minds in media — Amy Goodman, Thom Hartmann, Jasiri X, Davey D, Steve Katz, and Professor Richard D. Wolff — absorbing every lesson in storytelling, strategy, and impact.

A few blocks away was Brother Jeff’s Cultural Center, a hub of Black excellence and activism. Jeff “Brother Jeff” Fard saw something in me early on, giving me my first big breaks, my first backstage passes to history in the making. From tagging along on interviews with Sonia Sanchez to connecting with “Freeway” Rick Ross, those moments shaped how I see the power of media—how it can preserve culture, shift narratives, and change lives. To this day, Brother Jeff remains a trusted mentor and friend.

What started as a passion project—shooting photos and videos for local organizations—has become a full-service Digital Marketing & Media Boutique that helps brands do more than just show up. We make sure they stand out.

With a growing client roster of over 45 local, national, and international organizations, Miss Money Shot Media is built to amplify voices, elevate brands, and disrupt the status quo. We don’t just create content—we craft strategy, tell stories, and shape digital legacies.

Success, for me, has never been about fitting into someone else’s mold. It’s been about breaking it, rebuilding it, and making sure the next generation has a blueprint that reflects possibility without limitation.

Have you ever had to pivot?

My biggest pivot came when I realized that being a photographer wasn’t enough—I had to become a strategist, a storyteller, and a brand architect if I wanted to create real impact. I wanted to do more than survive, I wanted to thrive. I ended up finding the perfect intersection between purpose, passion and profit in the work I was doing.

When I started Miss Money Shot Media, it was all about portraits. I was capturing headshots, event photos, and brand imagery for local businesses and organizations. After a while, I noticed a pattern—clients didn’t just need great photos; they needed a strategy for how to use them. They needed digital assets that told a compelling story, connected with their audience, and ultimately moved their business forward.

The turning point came when a client asked me to help them “do more” with their digital presence. They had incredible initiatives, but their message was getting lost online. That’s when it clicked—I wasn’t just a photographer; I was a problem solver. I had spent years in media, working in digital strategy, production, and journalism. It was time to bring all those skills together.

So, I pivoted—from just taking pictures to offering full-scale digital marketing and brand strategy services. I built a team, expanded our capabilities, and shifted from selling images to delivering impactful campaigns, brand storytelling, and strategic content that elevated businesses and organizations. That shift, with the addition of a fleet of Photo Booths took Miss Money Shot Media from a side hustle to a full-service powerhouse.

That pivot wasn’t just a business decision—it was a mindset shift. I stopped thinking small. I stopped limiting myself to what I thought I was supposed to be doing and leaned into what I was truly capable of. And that’s the lesson: Sometimes, the pivot isn’t about changing direction—it’s about stepping into the fullest version of your purpose.

Thanks to my Day Ones, Hasira ‘H-Soul’ Ashemu and Mike Tipton, I started dedicating just as much time to strengthening my mindset as I did to building my business. The internal work transformed everything—the way I moved, the way I led, and ultimately, the way my business grew. What started as self-work became an undeniable outward reflection of my purpose and vision.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

One of the biggest lessons I had to unlearn was that success follows a linear path—that if I just worked hard, checked the right boxes, and followed the so-called “rules,” everything would fall into place. That’s a lie. Real success, especially as a Black woman in business, requires thinking beyond the blueprint, breaking rules that weren’t made for you, and building something completely new. I had to relinquish any thoughts of imposter syndrome, become comfortable with being the “only one” in the room and never forget to lift others as I climb. The truth is, there’s far more room at the top than there is at the bottom—it’s just up to us to make sure more of us get there.

When I first launched Miss Money Shot Media, I thought my job was simple: take great photos, deliver them to clients, and keep it moving. Over time, I realized that if I only saw myself as a photographer, I was limiting my own potential. The industry didn’t need another person snapping pictures—it needed someone who understood the power of visual storytelling, digital strategy, and brand positioning. I had to stop thinking inside the constraints of what I was “supposed” to be doing and start seeing the bigger picture—how I could disrupt the media and marketing space in a way that no one else was.

At some point I came to the realization that I’m not just in the business of capturing moments, I’m in the business of amplifying moments, making my clients feel seen, heard, and felt in a way that resonates with their audience. That realization forced me to unlearn small thinking and step fully into my role as a visionary.

I stopped asking, “How do I fit into this industry?” and started asking, “How do I change it?” How do I make it fit me? That’s when everything shifted. I expanded from photography to a full-service media and digital marketing firm, working with local, national, and international clients to tell stories that matter. I started hiring a team, developing long-term strategies, and leaning into what set me apart instead of trying to fit into a mold that was never meant for me. I leaned in and chased my weird.

Thinking outside the box isn’t enough—you have to be willing to step completely off the grid, out of your comfort zone and create something the world hasn’t seen before.

Contact Info:

• Website: https://www.MissMoneyShot.com
• Instagram: @missmoneyshot
• Facebook: @missmoneyshot
• Linkedin: https://www.linkedin.com/company/miss-money-shot/