The Bootstrapped Marketing Almanack, Part 5: Content Creation and Working with Creatives

Entries #101 through #125 of the Bootstrapped Marketing Almanack. This section focuses primarily on content creation, videography, and working with creatives.

What follows below is a running list of tips, tricks, and thoughts from my time (so far) building ANCORE’s business, brand and marketing from the ground up. This is the fifth installment and covers the content creation and working with creative talent. Each new installment will be published periodically. You can read Part 1 here, Part 2 here, Part 3 here, and Part 4 here.

Bootstrapped Marketing Almanack #101

Before hiring a videographer, hire yourself. Shoot content on your phone. If you have access to a camera, use it. If not, rent one. You can't know what you're looking for in a videographer until you've been in their shoes. Plus, the experience will build empathy and give you a better eye for quality content.

Bootstrapped Marketing Almanack #102

Always shoot more b-roll than you think you need. Nothing kills a content piece faster than running out of supporting footage. Those extra shots of products, hands working, or ambiance will save you in the editing room. Plus, you can always repurpose them for different projects later.

Bootstrapped Marketing Almanack #103

Natural light is your best friend when starting out. Find a window, face your subject toward it, and watch how the lighting instantly elevates your content. No fancy equipment required.

Bootstrapped Marketing Almanack #104

Sound matters more than picture quality. Viewers will forgive slightly blurry footage, but they'll click away from bad audio instantly. Invest in a decent microphone (there are plenty that work with a smartphone) before you even think about upgrading to a camera.

Bootstrapped Marketing Almanack #105

The best camera is the one in your pocket. Your iPhone is more than capable of shooting great content. Don't overthink it or wait until you can afford fancy gear. Just start shooting.

Bootstrapped Marketing Almanack #106

Learning basic composition (rule of thirds, leading lines, framing) will instantly make your iPhone footage look significantly better and more professional. These fundamentals are free to learn and will serve you better than any expensive camera.

Bootstrapped Marketing Almanack #107

Never start a shoot without a plan. Create shot lists, gather reference images, or build mood boards whatever works for you. But have something concrete to show and share. "I'll know it when I see it" wastes everyone's time and burns through your budget.

Bootstrapped Marketing Almanack #108

Don't overcomplicate your shot list. Focus on getting solid A-roll (your main footage or interview) and B-roll (supporting footage) first. You don't need fancy drone shots or complicated transitions when you're starting out. Master the basics, then level up.

Bootstrapped Marketing Almanack #109

Always have more SD cards and hard drives than you think you need. Memory cards fill up fast, and running out of storage mid-shoot is a rookie mistake you can't afford to make. Pack extras of everything.

Bootstrapped Marketing Almanack #110

Back up your footage in at least three places: local hard drive, external drive, and cloud storage. No excuses. Lost footage means lost time, lost money, and lost trust. You can recover from bad footage, but you can't recover from no footage.

Bootstrapped Marketing Almanack #111

Charge all your gear the night before a shoot. No exceptions. If you're charging batteries the morning of, you're already behind. Dead batteries will kill a shoot, the vibe, and your momentum.

Bootstrapped Marketing Almanack #112

Always have backup batteries and keep them charged. One battery isn't enough, two batteries aren't enough. The second you think you have enough batteries, buy one more. You'll thank yourself later.

Bootstrapped Marketing Almanack #113

Organize your equipment, even if it's just dollar store bins on a shelf. Separate phone gear from camera gear. Keep batteries with chargers. Sort cables by type. The more organized your gear, the faster you can work and the less likely you are to forget something crucial.

Bootstrapped Marketing Almanack #114

When working with videographers, aim for partnership, not dictatorship. Give them a clear vision of what you want, then let them work their magic. The best creative work happens when there's trust on both sides. And don’t forget to offer to buy coffee, lunch, dinner, or any meals that might happen while shooting. They are helping you so you need to help them.

Bootstrapped Marketing Almanack #115

Create a brief for your videographer that outlines your goals, vision, and must-have shots. Then step back and let them add their creative expertise. You hired them for a reason, so let them show you why.

Bootstrapped Marketing Almanack #116

The best clients get the best work. Be organized, respectful of their time, and clear with feedback. When videographers love working with you, they'll go the extra mile to make your content shine.

Bootstrapped Marketing Almanack #117

Always ask your creative partners: "How can I be the best client for you?" It's a simple question that no one asks, but it sets clear expectations and creates a roadmap for success. The best relationships start with understanding what each side needs and all it takes is just asking the question to get there.

Bootstrapped Marketing Almanack #118

As a shoot manager, your job is simple: keep everyone happy. Don't hover over the camera or micromanage. Instead, focus on making sure your talent is comfortable, your videographer is supported, and the overall vibe stays positive. A relaxed set produces the best content.

Bootstrapped Marketing Almanack #119

When filming someone, emphasize that you're just having a conversation. No one's looking for perfection — we're looking for authenticity. Let them know it's okay to stumble, restart, or take a breath. The best content comes from relaxed conversations, not stressed performances.

Bootstrapped Marketing Almanack #120

Something will go wrong during your shoot. Accept this truth now. Equipment will break, weather will turn, audio will fail — it's inevitable. Don't let it derail you. Take a breath, assess what you can still accomplish, and keep moving forward. The show must go on.

Bootstrapped Marketing Almanack #121

Always buy lunch for your shoot team. It's not just about food — it's about taking care of your people and maintaining positive energy throughout the day. A well-fed crew is a happy crew, and happy crews create better content. Don't think twice about this expense; it's an investment in your shoot's success.

Bootstrapped Marketing Almanack #122

Always review a videographer's past work before hiring them. Don't be afraid to ask for examples and references. You need to see if their style matches your vision and, more importantly, verify they can actually deliver quality work. A great portfolio means they can do the job. No portfolio usually means no hire.

Bootstrapped Marketing Almanack #123

Think in planes when shooting: tight, medium, and wide. Get detail shots that show what the eye can't normally see. Capture medium shots for context. Add wide shots to set the scene. Master these three perspectives and you'll have all the footage you need.

Bootstrapped Marketing Almanack #124

Zoom with your feet, not with your camera. The zoom function on your camera is your enemy. Want to get closer? Walk up to your subject. Want a wider shot? Take a few steps back. Your footage will look cleaner and more professional.

Bootstrapped Marketing Almanack #125

Always mind your backgrounds and surroundings. A clean, distraction-free environment lets viewers focus on your subject. But a messy background, random people walking through shots, or cluttered spaces will ruin even the best content. When you get it right, no one notices. When you get it wrong, everyone does.