Your First: Company Swag

At Initialized, we understand that as a founder, your initial experiences matter deeply, and every decision can feel like it carries significant weight. That’s why our founder impact team is launching a new blog series, ‘Your First…,’ aimed at guiding founders through key moments in areas such as marketing, PR, talent, go-to-market strategies, design, community/events, storytelling, content creation, and more.
We have already published posts to assist early stage founders with their first funding announcement, first 10 employees, first brand considerations, and first customer event.
Today, we are excited to share some of our tips for how to produce your first set of company swag.
So, you’re ready to design and produce some company swag. Perhaps you want to surprise your team with a holiday gift, have an upcoming conference where giveaways might be useful, or are looking to create a lovely welcome package for new employees. Whatever the reason, here are some steps to get you from ideation to final product.
Planning
The swag process inevitably takes longer than you think, so planning and prep are key to helping you meet deadlines. Give yourself at least three months in case you hit any bumps along the road and follow the below steps to kick off your process.
Define your audience: Is this swag for your employees? For customers/prospective customers? Event attendees? Consider who is receiving the swag and what their style may be. You may need to go classic with customers, for example, where you perhaps can be more playful and creative with employee swag.
Define your goals: Is it brand awareness/promo? Event engagement? Employee surprise and delight? Customer loyalty? Think through the outcomes of creating swag before moving to design. Do they align with your brand vibe/voice/tone?
Budget: How much is reasonable to spend? How many units do you need/want to produce? Are you designing one product or a suite of products? Do you need to hire a designer to support the project? Do you want high-quality items or are you going for quantity over quality? Consider the audience and goals to help define this.
My Tips
- We have broad strokes for different audiences, so I like to design and produce two to three different designs for each swag drop. It may all be the same Marine Layer sweatshirt, but there’s perhaps a classic look, a street look, and/or a feminine look.
- I lean toward quality over quantity. If you want people to rep your swag, spending a bit more for quality goods and brands pays off. Think about what swag you’ve kept and what you’ve thrown away. Why? No one needs another tote that’s going to fall apart mid-grocery run or a scratchy, ill-fitting t-shirt. Your brand can take a hit if you produce crap.
- When budgeting, it can be tempting to buy in bulk because typically the more you buy, the cheaper the per-item price becomes. But be wary of over-ordering as you may end up with extra swag lying around the office untouched for years.
- Sometimes you may need to reverse engineer into your budget based on the designs or brands you want to work with. That’s ok, as long as it’s not breaking the bank.
Designing
One may argue, the fun part! This is where you decide what your swag will look like and the vibe you want to present to your audience. The below steps will ensure you’re happy, visually speaking, with your final product(s).
Identify a designer: Have you already honed your visual identity? Great! Classic swag should be easy. If not, utilize an in-house designer, a freelance designer, or contemplate whether it’s time to explore your visual identity (see my blog on lean design here). Having a logo, color palette, tone/voice, and overall aesthetic is important, even in B2B. Swag vendors can help with design, but keep your expectations low. They won’t do much out-of-the-box thinking and if you don’t have solid assets to work with, it may all come out fairly bland.
Determine the “what”: What are you designing? Marine Layer hoodies, Vuori pants, Baggu totes, bucket hats, umbrellas, Airtags, or picnic blankets? Your designer will have suggestions or you may have a good understanding of what you want to produce based on audience. This is a bit chicken and egg because you can always mock up a design on any sweatshirt and then select the brand at a later date. If you have a specific, unique product in mind, select it first so the designer can design around it. This will save time and back and forth on logo placement, color palette, etc.
Design and iterate: Ask your designer to come up with several different options for you to review and provide feedback. This could be different colorways, different logo placements, different products, you name it. It’s good to visualize mockups before pulling the trigger on anything.

My Tips
- Poll your employees. What do they actually want? What have they seen at other events that they considered cool or useful? What do they anticipate customers want or, even better, can they ask a few close customers? The last thing you want to do is produce more stuff that people will simply throw away. Don’t go too wide with your advice collecting, though, or you might end up with too many differing opinions. Sometimes I’ll select 2-3 people who fit the audience (sometimes employees, sometimes founders) and Slack them product options for feedback. Other times, I’ve built a visual Typeform to gather feedback.
- Look around and witness the brands your audience is wearing/repping. Are they in your budget? Do they sell in bulk and/or offer custom options? Many times you can find more information on the footers of websites or you can simply email and ask.
- Consider swag items that tie back to your brand. Is there something unique about your value prop, branding, logo, etc. that people gravitate toward? Can you build off that to say design a bespoke desk object?
- I can’t overstate this enough. Don’t try and skimp on the “design” of the swag itself. The design is just as important as the products you select. We sometimes review 8-10 designs, give feedback on 3-4, then finalize from there. It’s a process worth spending time on.

Producing
This is where your designs and vision come to life. Production can be time-consuming at first (and dependent on product selection and availability), but once you’ve built a relationship with a swag vendor, each run gets more and more smooth. Here are some additional tips for how to work with vendors.
Outline creative brief: I’ve found communicating the designs, brands you like, cost per unit, timelines, etc. up front to be extremely helpful when working with vendors. Use this to reach out to 3-4 vendors and compare/contrast the products and pricing they provide.
Vendor outreach: Vendors do all the heavy lifting when it comes to final product selection/purchasing, producing, and shipping your swag. There are many different companies that do this and it can be overwhelming to choose. I suggest picking a vendor based on their inventory, communication, brand, and word of mouth. If you only want eco-friendly products, for example, search for vendors that source sustainable products. We’ve had great success with Canary because of their relationships with brands and speedy turn-around times. They are also patient when we experiment with new colors, layering, etc.
Create: Ask for a dry run of all designs so you can see them produced before you green light the full run. If everyone is satisfied, move forward, and wait for your swag to arrive. Consider how you’d like to distribute (more on that below). If you’re going to a conference, for example, have the swag shipped directly to your hotel or the venue so you don’t need to travel with all the items.
My Tips
- If you are distributing nationally or internationally, consider using Fourthwall, a portfolio company. We use our Fourthwall stores to ship out swag to employees, founders, and LPs. That way everyone gets to select their favorite items, preferred sizes, and best shipping address. Fourthwall is also a great platform to use if you ever consider selling your swag.
- Once you have selected the vendor that has access to the types of products/brands you want, order samples of your considerations. Seeing them, feeling them, trying them on is hugely important. Have different genders and sizes try on to ensure any unisex products aren’t extremely large and/or to determine if you should purchase items in men’s and women’s cuts.
- If anything is off or doesn’t feel right, communicate that ASAP. Vendors want you to be satisfied with the final product. I once went back and forth about a logo placement on a RAINS backpack several times, ultimately moving it 1/4 inch.

Key Takeaways
- Think through your audience, budget, and goals before diving into the creative fun of swag design.
- Don’t produce crap that people don’t want and/or that could tarnish your brand.
- Work with a designer and/or highly tasteful individuals at your company to make sure your swag exceeds the bar.
- Ultimately, make something you and your team would be proud to wear or display.
Happy swagging.