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7 Questions on Leadership with Tim Bradley

Name: Tim Bradley

Title: Co-Founder, Executive Producer

Organisation: Pennant Video

Hello, I'm Tim Bradley – thrilled to be the Co-Founder & Executive Producer at Pennant Video, where we excel at creating the three most effective types of video content that propel business development for brands: Anthems, Explainers, and Endorsements. We refer to this as the Video Marketing Trifecta, and Pennant stands as a brand’s video-first marketing partner.

With nearly two decades of experience in the video production realm, my mission is to energize the impact of video in the marketing world.

Throughout my career, I've spearheaded numerous projects across various industries, focusing on empowering global sales and marketing teams with exceptional content and the tools they need to excel. I specialize in strategic planning, creative direction, motion design, video production, and optimization strategies.

Beyond work, I relish quality time with my family, enjoying outdoor adventures like snowboarding, hiking, and hitting the beach.

Thank you to the 2,000 leaders who’ve generously done the 7 Questions on Leadership!

I hope Tim's answers will encourage you in your leadership journey. Enjoy!


Jonno White

1. What have you found most challenging as a leader?

Here I am, knee-deep in the exhilarating chaos of entrepreneurship—a journey filled with triumphs, tribulations, and plenty of "whoa, didn't see that coming." Today, I want to share a bit about my adventure, particularly the trio of challenges that have become my closest companions: crafting a dream team, carving out a memorable brand presence, and mastering the delicate art of balancing the work-life seesaw.

Let's rewind a bit to the early days. The realization hit me like a ton of bricks—this isn't a solo gig; it's a team sport. As I gathered my crew, I quickly learned that it's not just about resumes and skills. It's about finding kindred spirits, the ones who not only get your vision but add their unique flavor and sense of purpose to the mix. We're not just colleagues; we're collaborators on a thrilling journey.

Communication is our secret sauce. We're all about open dialogue. Ideas bounce around like confetti, and everyone has a say. It's not just about reaching our destination; it's the laughter, camaraderie, and shared victories that make this journey unforgettable.

Now, let's talk brand. Early on, I realized Pennant’s brand isn't just a logo or a color scheme; it's a personality. What makes us tick? What makes us stand out in the crowded marketplace? We dug deep, found our quirks, and flaunted them shamelessly.

Consistency has become our anthem. Whether it's our website, social media banner, or a showcase of our motion design chops, we ensure our brand personality is front and center. Authentic connections are our currency. People want real, not robotic. Sharing our story makes us relatable, and being memorable? Well, that's just the cherry on top.

Now, the part where the rubber meets the road—juggling work and life without dropping either. The hustle is real, but so is the danger of burnout. Setting boundaries became my superpower. It's not about working harder; it's about working smarter.

Delegation has become my lifeline. I've got an A-team, and trusting them to shine is my biggest flex. And self-care? That's not negotiable. Whether it's a simple midday stretch, a coffee recharge, or a walk in the woods with my family, I've learned to recharge my creative batteries.

This entrepreneurial journey is a personal odyssey. There's no one-size-fits-all guide, and that's the beauty of it. Here's to celebrating wins (no matter how small), learning from the challenges, and reveling in the unpredictability of it all.

2. How did you become a leader? Can you please briefly tell the story?

I've built my career in brand video production, mostly on the agency side, honing my storytelling skills and understanding how video enhances business development. Agency life has been fertile ground for personal and professional growth, where I've led teams to create stellar work for global businesses. But, more importantly, I’ve got to build character and build up people.

Now, I’m getting a second chance to build a brand and business. Diving into the whole Pennant Video adventure has been like stepping into a world of independence and autonomy. I get to call the shots, make the big decisions, and basically set the vibe for how we roll with our video marketing content. It's this incredible feeling of freedom to shape things just the way we want.

And you know what's even cooler? We're doing it in a way that doesn't just value hard work but also champions a balanced life. I've made it a point to create a space where the team can give their best at work and still have the freedom to rock their personal lives. It's not just about the grind; it's about finding that sweet spot where work and life vibe together seamlessly. There are only so many hours in the day, but I’m grateful for every moment I have to make my dream a reality.

I've realized that my secret weapon is my genuine intent. I'm the kind of person who's driven by a sincere desire to do what's right, not by any sneaky motives or a thirst for power over others. Even when I don't see eye to eye with someone, I always try to find common ground.

I've noticed that this approach gives me a unique ability to communicate with a certain eloquence and sensitivity. I have a strong desire to carry empathy in all aspects of my life. People seem to really tune in, especially when I'm talking about things that truly matter to me; it's like my authenticity becomes impossible to ignore. Ever feel that way too?

3. How do you structure your work days from waking up to going to sleep?

With two young children - ages 7 and 4 - the routine is pretty straightforward. I strive to wake up well before dawn to get in a workout with my wife or at least walk on the treadmill. If I’m walking, I’m usually multitasking by reading a business book or listening to a marketing podcast. This is also when I set my goals for the day.

Once the kids are at school and I’ve had my coffee, I lock into at least 2 hours of business development activities first thing. It’s a blend of direct outreach or follow up as well as writing for my personal brand on LinkedIn and developing our next piece of marketing content for Pennant. This is the most crucial part of the day; you can’t have a business without sales, so it’s my biggest priority.

Around mid-late morning, I check in with the team on the priorities. It’s a mix of operations and client fulfillment in the mid-section of the day. The end of the workday is usually emails and more simple tasks - along with an afternoon coffee.

Evenings are controlled chaos: pick up the kids from school, make dinner, do dishes, baths, reading, and songs for the bedtime routine, and cleaning up the kitchen. Folding laundry is a bonus.

Since I’m usually on Google Meet or Webex or Zoom talking all day, my brain tends to be fried, so I wind down with a show on Apple TV or Netflix. Sometimes, after an especially intense day, my wife and I will make a mocktail and do a puzzle together. It’s a nice moment to just focus on each other.

4. What's a recent leadership lesson you've learned for the first time or been reminded of?

I've been reminded that leading isn't about sprinting to the finish line; it's more like running a marathon. The whole "it's a marathon, not a sprint" thing has hit home. I've realized that for our team and the projects we're tackling, it's not just about quick wins. It's about pacing ourselves, being patient, and staying focused on the long game. Leadership, I've learned, is about endurance and guiding everyone through the ups and downs with resilience. It's not always easy, but it's definitely a valuable lesson in the importance of sustained effort over time.

5. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

There's this book called "A Company of One" by Paul Jarvis that has really shaken up how I see leadership. It's not your typical business growth playbook. Instead, it dives into the idea that staying intentionally small, like operating as a "company of one," can be a game-changer.

Jarvis dives deep into the idea that deliberately staying small, like running a "company of one," can be a serious power move. It's not about avoiding success but about redefining what success looks like. The book hits on some major themes that have stuck with me.

First off, sustainability is front and center. It's all about building a business that can weather any storm, not just aiming for explosive growth. And autonomy – that's a big one. The book champions the idea of keeping control over your business, making decisions that vibe with your vision.

Efficiency is another gem. Small businesses can be agile and quick to adapt, something that's often lost in larger organizations. "A Company of One" also puts a spotlight on the value of quality over quantity. It challenges the whole idea that bigger is always better, suggesting that honing in on a niche audience with top-notch products or services is the real key.

But what really hit me was the concept of lifestyle design. The book pushes you to create a business that fits into your life, not the other way around. It's about finding success on your terms, not what society tells you success should look like.

In a nutshell, it's made me rethink the whole growth-for-growth's-sake mantra. It's all about leading in a way that aligns with your values, keeps life in balance, and sets you up for long-term success. Definitely worth a read if you're into that kind of business wisdom.

6. If you could only give one piece of advice to a young leader, what would you say to them?

One piece of advice I frequently share with young leaders is the inevitability of making mistakes—likely, quite a few of them. The crucial insight here is to encounter as many mistakes as possible, and to do so swiftly. Embrace the concept of failing fast, recognizing that rather than fearing failure and striving to evade it at all costs, leaders and teams should view it as an inherent aspect of the learning process. It's about spotting what clicks and what doesn't ASAP, soaking in the lessons, and tweaking your game plan. This approach not only strengthens your leadership but also cultivates a culture of adaptability and continual improvement. Embrace the fails, learn quick, and keep rocking it.

7. What is one meaningful story that comes to mind from your time as a leader, so far?

Most of my meaningful stories that come to mind have less to do with business leadership and more to do with being a “Dad-preneur.” Being a dad and running a business is like juggling two roles at once. You've got to be a time wizard, managing family and work like a pro. Flexibility is the name of the game because, let's face it, both family life and business throw curveballs. Leading the pack is crucial, setting the tone for hard work and doing things right, both at home and in the office.

Every night during dinner, we take turns as a family sharing “the best part of our day” with each other. This was actually my four-year-old son’s idea, and I love it. It’s often the best moment to help transition from work to family time and a great “grounding rod” for myself to recognize what’s important and what I’m really doing all this for in the first place.

You've got to be patient as a saint—family life and business can test your zen.

Communication is key, whether you're talking to your kids or your team. Feeling what others feel - aka empathy - goes a long way in keeping everyone happy.

What's cool is integrating work and family life; it's not about keeping them separate but finding ways to blend them together. Ultimately, the most effective Dad-Preneurs find a way to harmonize the roles of fatherhood and business ownership, recognizing the unique challenges and rewards that come with each role.

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