Starting over mid-career is a strange thing. I’ve done it a few times, with mixed results.

After selling my company in 2015, I gave myself five years to explore passion projects before choosing what came next. At 35, with three kids under five, I wanted my next real move to be intentional. Those years went fast, a blur of startups, ideas, late nights, and being the mayor of Kidville, USA. But they taught me something important: I’m at my best when I’m solving problems through design and building brands, systems, and products that help real people.

So that was the plan. I’d start a design agency.

Within a week, my first client fell into my lap. A pitch turned into a 6-month engagement that ended in a big win: great results, good money, creative push, awards, and a thrilled client. I wanted more of that: more clients, more collaborators, more momentum.

And then I saw the flaw in the model I was trying to build.

Where the traditional agency model breaks.

The only way to scale an agency is to take on more clients and hand off execution to cheaper, faster labor. That’s how every service business scales, but in the creative industry, it creates a huge gap between what’s sold and what’s delivered.

Clients hire agencies for senior-level craft (the work shown in the pitch deck or portfolio), but most of the execution is handled by junior designers.

Here’s how it usually plays out:

1. The founder or salesperson leads the pitch, showing A+ curated work.

2. A senior designer runs the kickoff and sets direction.

3. Then the senior steps aside, and 90% of the work is completed by juniors at bargain internal rates. Capitalism at work!

4. Project managers focus on timelines and cost, not craft.

5. The final product rarely lives up to the promise of the pitch.

I know this pattern too well. I’ve been the client in this story more than a dozen times and can always tell the exact moment an agency shifts its attention to its next, shinier client.

Suddenly, you’re managing the people you’re paying, trying to drag your own project across the finish line.

Nobody leaves happy.
Clients feel shortchanged.
Agencies feel squeezed.
And both sides pretend this is normal.

The truth is simple: the traditional agency model is built for efficiency, not for excellence. It protects margins, not relationships. And it consistently produces work that feels disconnected from the promises made at the start.

So I walked away.

A better way: embedded design leadership.

What works, for both sides, is a model built on partnership, not production. A model where creatives operate as embedded members of the team, working in the open, with continual communication and shared ownership of outcomes.

This approach fixes the pitch-versus-delivery gap because the person doing the work is the same person shaping the strategy. There’s no handoff, no dilution, no mystery behind the curtain.

But it demands a lot:

• Embedded designers need commercial-grade skill and real emotional intelligence.

• They must adapt quickly to company dynamics and stakeholder goals.

• They have to perform under a microscope, maintaining high craft in real time.

• Agencies using this model take on fewer clients and give each more attention.

• Clients must trust the embedded talent and grant access to decision-makers.

It’s harder. It requires more vulnerability on both sides. It limits the number of engagements you can take. And yes, it can mean less cash at the end of the year.

But the work is better. The relationships are healthier. And everyone moves faster with greater clarity.

Getting pinged in Slack to make a quick update is better than navigating a multi-step SOW process. Building in the open with smart, kind people from all over the world makes you feel like part of something bigger. And the outcomes speak for themselves.

I can’t go back.

Where to go from here.

If you’re deciding whether to hire internally or bring on an agency, ask yourself which model creates true alignment for the people involved. Often, the right individual operating in the right model is what unlocks the outcome you’re after and makes you look good in the process.

I’ve been working with select teams in this embedded capacity for the past few years and have launched some pretty incredible things. If you’re exploring this approach or want to talk about what it might look like inside your organization, reach out and let’s chat.

One of the hardest disciplines in an entrepreneur’s life is reflection.

Not because we never think about the past, or don’t try to learn from it, but because most of us are futurists by instinct. We live in the “what could be” more than the “what happened.” Both perspectives add value to the world, but one of the drawbacks of always looking ahead is forgetting to pause long enough to acknowledge what was good.

This discipline doesn’t come naturally to me. It requires slowing down, some focus, and a bit of annoying journaling. But the outcomes are always worth it. When I do stop and look back, I’m overwhelmed with a sense of gratitude for the great moments, the hard ones, and all the strange in-betweens.

I’m in that headspace with Wildland. Even though the journey was littered with plenty of shitty moments, when I step back and look at the six years spent trying to launch an outdoor skincare brand, I’m massively thankful I got to experience all of it.

This post is part of a short series I’ve been writing about the closing of Wildland, what I learned, and what I’m taking with me into whatever comes next.

Grateful for the home team.

The best part of any venture is experiencing the journey with friends. Not as business partners or trusted vendors, but as close friends, just trying to support your vision of creating something out of nothing. Launching a company not only refines and tests your tenacity and endurance, but also gives your close friends a chance to show up and shine.

The Wildland launch was no different than any other venture I’ve started. My friends showed up for sunrise video and photo shoots, helped me lug product to locations, sacrificing mornings and weekends simply because they were my friends and wanted to help. No promise of an hourly rate or potential equity, just payment in beers and high-fives.

I’m massively grateful for my friends and family who were rooting for Wildland’s success with me over the past few years, and demonstrating care through words and action.

Grateful for the customers.

Wildland customers were the best part of the experience. Loyal to their core, willing to spend a little bit more money for a higher quality product, while supporting an unproven start-up. Retail stores across the country stocked our product with zero complaints, eager to give us a shot. Communications were always positive, even when the product was damaged mid-shipment or orders accidentally got mixed up in third-party logistics.

The hardest part of shutting Wildland down was having to tell customers that we were closing shop. Emails came flooding in, thanking us for the product with kind words, wishing us the best in the future. Our customers were incredible.

Grateful for the path to try.

Bringing any physical product to life is never simple. Taking something that doesn’t exist, learning to manufacture it, and then seeing it on shelves at a major retailer should be nearly impossible.

It took long hours, our own cash, and more than a hundred phone calls where I felt like the dumbest person in the room, but the path was still accessible. Living in the U.S., having the internet, and having kind people willing to answer question after question made launching Wildland possible.

I probably had no business starting a skincare brand without prior experience. But I’m grateful I got the chance anyway.

Grateful for the experience of it all.

In the end, I’m grateful for everything, the wins that made us feel unstoppable and the failures that hit hard. I learned a lot about myself, my friends, my family, business partnerships, and ultimately, how to recognize when it’s time to turn the lights off.

Not everything is meant to be forever. I’m grateful for that, too.

This little series of posts I’ve been writing over the past couple of weeks recounting the missteps of Wildland has been rather cathartic.

Although, if I’m honest, the recount has left me a bit crispy as I analyze certain aspects of the experience, I’m absolutely grateful for the insights my postmortem has provided my future self. If your curious about some of the more granular lessons from this venture, be sure to check them out, starting here.

Coming to Grips With Reality

After running the final numbers for Wildland, my outdoor-focused skincare company, I caught myself wondering if I should just keep it alive as a hobby. I loved what we built. The product worked, people loved it, and I believed it made the world a little better.

But after six years of work, investment, and hope, the math told a different story. The truth was simple, even if it took me a while to admit it: I was done.

Closing Wildland wasn’t just about money or market fit. It was about learning where I actually thrive, and where I don’t.

Wheelhouses & Whatnot: The Big Takeaway

Over the last twenty years, I’ve founded a dozen companies, launched twenty brands, and sold three. A 25% success rate isn’t bad, but what’s more important is what those ventures taught me: I’m wired for the 0→1 phase of a business, the part where a scrappy idea becomes real.

Even in my current design and consulting venture where I work with both enterprise-level clients and new startups, I notice myself gravitating towards this phase of a company or campaign.

To me, it’s the most magical season for startups. The time when creatives and builders work their collective asses off to make a dream tangible. It’s the most anti-corporate kind of work you can do. Stakeholders are as hands-on as possible, living, breathing, and sacrificing to make their idea real. Things move as fast as possible, having to make massive decision after massive decision, attempting to successfully launch a previously non-existent brand and product to the right, first customer.

It’s focused chaos, and I’m built for it.

In contrast, the post-launch slump is very real. After all the initial research is complete, the brand is created and dialed in, and the MVP is built and launched, my excitement typically drops from a 10 to about a 3.

I used to be frustrated by the slump, feeling like if I just worked harder, I would learn to love the next phase of a start-up. The “2→10” phase is when you dial in your marketing plan, sales team, analyze customer feedback, iterate, potentially pivot, etc. The childhood to puberty of a company.

But let’s be honest, no amount of hard work would have ever made me love the hellscape of junior high. Unfortunately, the same is true for the 2→10 of a company. I’m just not built for it.

The successes I’ve found were the ventures that accounted for this phase of the company. Previous wins came from having a dynamic co-founder, having deep knowledge of the market, and/or executing a marketing and sales plan that immediately found return and funded growth. I had none of these with Wildland.

My greatest personal takeaway from my experience with Wildland has been that I am built to create. That I am a generalist with a passion to build brands, design products, and launch them into markets. I love to live in the 0→1 of a company, and need to outsource the hell outta the 2→10.

Last, Smaller, Wildland-centric Takeaways

If I move past my introspective “journal entry” of a lesson, there have been some other, more practical takeaways that lead me to why I’ll never start another skincare company again in my life. Hopefully, some of these takeaways might help lead you to ask the right questions if you are considering building a similar company.

• Higher ticket items > small-ticket grind. Selling a $20 product that costs around $3.50 to produce, nets on average about $6 on a good day after all is said and done. If I were to build another DTC product, I would find one that is much higher priced, ideally finding higher and quicker profits.

• Digital > physical for flexibility and margins. Shipping, receiving, floating inventory, storage, returns, and pick fees are very real costs unique to physical products. Digital products have none of those, along with the ability to pivot quickly without massive potential losses.

• Seasonal products can starve you for 9 months. Be careful to understand the buying cycles of your product. For Wildland, we sold most of our product over a 3-4 month period, but our product still had expiration dates and needed storage for the remaining 8-9 months. Whether relying on Christmas or the weather, products with a window for sales are expensive.

• Waiting/hoping ≠ a strategy. Without a distinct plan for sales (whether retail connections or a solid DTC marketing plan), simply waiting for a deal to strike is not enough. Before building, know and vet your sales plan.

I recognize these “bigger takeaways” are a bit tactical, and not necessarily applicable to most startups. My hope is that for those that are broadly in this niche, these (along with my manufacturing and sales lessons) will help in your new journey.

Final Thoughts

At the end of the day, any start-up is a risk.

You take a swing, sometimes you hit and other times you miss. Although I ended up shutting the company down, I don’t regret Wildland. It taught me that I do my best work at the beginning, when I help ideas take shape with care and clarity. So that’s where I’ll stay.

For those entrepreneurs out there, remember to align your ventures with your personal skills, temperaments, and passions. We all have our blind spots, but knowing and accepting them will lead you to build the best team along with a well-rounded strategy necessary to take your start-up from 0→1, 2→10, and then 11→1000.

I am lucky enough now to spend most of my time helping founders and teams navigate that 0→1 phase. Sometimes it’s an enterprise company trying to connect their brand, product, and marketing in a more cohesive way. Other times it’s a startup looking for clarity and a solid launch plan. Either way, that’s the work I love most. If that sounds like you, let’s connect and see what we can build.

A great salesperson is quite literally worth their weight in gold. Without sales, even the best-designed brand can crumble. Great product doesn’t sell product. At Wildland, we learned that lesson the hard way.

For us digital product builders, good salespeople have the uncanny ability to translate simple and obvious features into real cash. It’s pure magic.

You can sometimes skate by with digital products by just paying for digital ads and marketing campaigns to handle the bulk of your selling. A/B testing, influencer buys, social media posts might be enough to sustain as you ramp up growth. This is easy to do when you are not paying monthly for product storage and have no fear of a product expiring in the next couple of years. It allows you to take the time needed to grow organically, not necessarily needing a full sales team. Sure, growth might be slower, but it is definitely possible.

Physical products are a different beast.

The second you manufacture a product, it’s a race against time. You need to validate your product that is untested in a market, all while spending money to basically stay in business. This constant threat of costs being unmet by sales forces big ad buys or other swings (like sponsoring industry events or attending conferences) simply to get your product in front of the right people.

But in theory, this is where salespeople come in. These white knights ride in to sling your product to anyone and everyone who might want it. From distributors to mom and pop retail shops to big box retailers, they are here to sell, armed with a cell phone and an industry-specific rolodex.

Right Perspective, Bad Timing

The realization of how valuable salespeople are came a little too late for me at Wildland.

When our product launched in 2019, we agonized over every aspect of the product and brand. Whether it was because my chops were in brand and product design, or because neither of us founders particularly liked or were any good at sales, I’m not exactly sure - probably a bit of both. Either way, the outcome was the same. We basically ignored traditional sales.

In my mind, though, that was ok.

I genuinely felt that if we built an incredible brand and vision alongside developing and manufacturing the best product in the category, people would find it and share it with their entire contact list. But here’s the raw truth:

Our product and packaging stood alone, beautiful on shelves against others in the space. Our wholesale brochures were agonized over, and looked sexy as hell. Our website told a story, had beautiful imagery, offered tips when engaging with poison oak and ivy, even gave advice on which trails to try when visiting California’s central coast. We had dope merch, custom hats, sticker packs, water bottles, and even custom, unscented air freshener trees that encouraged you to roll down your window to experience the mountain air.

But it turns out none of that sold product at enough scale to stay in business.

I knew that the idea of “if you build it, they will come” was a farce from when I started my first business, but I had never translated it to physical products. I assumed a good pitch and elegant brochure would open doors to any retail store or connection Wildland made. Turns out we were wrong.

Aside from a few of our friends and connections who have retail adventure and mountain bike shops on the central coast (shout out to The Mountain Air) and a random contest allowing us to pitch and eventually be sold in REI nationally, most sales were one-offs on Amazon or our website. Not nearly enough to float a company.

We needed some big accounts to make this thing work.

Retail Sales Nightmares

A year or so into business, the writing was on the wall that we needed some large retail accounts to help kickstart our exposure into the greater market. One-off sales were great, but they simply weren’t moving the needle fast enough to gain any momentum with our brand.

This reality pushed me to move far outside my comfort zone, trying every avenue I could think of to get Wildland in front of buyers for regional and national retail chains.

I got pretty good at tracking down and cold emailing category buyers from the big chains. I had created a list of about 20-30 names and emails pre-COVID, with one to two emails back with super soft interest. I’d send products and follow-up emails into the depths, never to hear from them again. Then, post-COVID, I found out that most buyers were let go or changed jobs , forcing me to start the entire process over.

The worst experience of my failed attempt at retail sales came from the three different times I specifically hired firms “with previous buyer relationships and experience” to get my product in front of large regional and national buyers for stores. With a simple monthly retainer, these companies promised buyer exposure to companies like CVS, Costco, Walgreens, Rite Aid, and Dicks Sporting Goods, to name a few.

Each time I would chat with them on the phone, guarantees would flow with stories of their firm launching brands I had never heard of, but should have. But even though my bullshit-o-meter was off the charts, the promise that for a couple of grand a month I would get infinite opportunities for success would push me to sign the contract. I just kept thinking, “all I need is one deal to pay back the investment.”

After three separate companies, guess how many times I was able to even speak with a buyer? You guessed it. Zero.

Thousands of dollars of product, combined with endless hours in preparation and check-in meetings for absolutely nothing.

After the last attempt, I was resigned to simply reacting and moving more to DTC sales as opposed to retail.

DTC: My Last Real Attempt

To close the loop on Wildland, my very last attempt was to go as all-in as I could on DTC sales. This meant bringing someone on to optimize my entire digital ecosystem (socials, website, Amazon, etc) and then run and optimize ads.

I genuinely felt that if I could prove some sort of return in advertising, I could see a path to Wildland’s success.

I found an amazing ads guy through a friend of mine and got working. We started running ads and optimizing at the beginning of 2025, and then ramped up to the height of poison oak and ivy season in April and May. This was it.

It was amazing seeing so many sales happening. I used to have 3-4 sales a week, so seeing my phone blow up with 10-20 orders a day was incredible! Sure I was spending money, but sales velocity was starting to happen and it felt validating.

It felt good until I ran all the numbers in May from April’s sales.

Numbers don’t lie. My average order was $22 through Shopify (direct through my website), and $24 with Amazon. After refining and targeting over the past three months, my CAC (customer acquisition cost) was $55 for Shopify, and $24 for Amazon.

The delta between what I needed to make to be profitable and reality was just too much. I could probably make small, incremental changes and combined with more time refining ads see a little better return, but by that point I was just done. Any light at the end of the tunnel flickered out that May.

Lessons Learned

There are definitely things I wish I knew before starting this journey. In previous digital ventures, we had a ton of marketing and advertising success when launching ventures through smart ad buys, partnerships, and referral programs.

But that success did not translate to my physical product experience. Here are the sales lessons I wish I had understood before starting Wildland.

• Yes, you need a salesperson. If you or a co-founder doesn’t have preexisting relationships or an unfair advantage to sell your product in your market, you either need to find a sales co-founder or first hire someone who does.

• DTC takes serious cash + a lever. For DTC to begin to return and begin to make enough revenue to actually pay yourself, you need two things:

  • Money. A lot of it. For ad spend to work, you have to burn a lot. If I had to do this again, I would start at around $500K for the first six months, ramping up from there before I expect a return.

  • A “lever”. You need something that ignites sales. Think previous retail relationships or The Rock.

*(These two things are not required for growth, but know that if you bypass these your growth will be really slow and tedious.)

• Influencers ≠ sales (99.99% of the time). A few might work, but you can’t expect any direct sales. When budgeting for influencer posts, file under PR rather than sales. Influencers are good for exposure versus return.

• A sexy brand isn’t enough. Most people can’t tell the difference between a Timex and a Rolex on someone’s wrist. When selling on brand, you’d better be selling in a category that is looking for status, rather than a solution.

• Small marketing spend creates small results and minimal information. The opposite is true as well. Strategic big spends create big results and big information. You get what you pay for.

• Retail buyers are risk-averse and want proof. This practically means:

  • Distributors with current shelf space are a priority.

  • Without proven retail sales, you have a very, very slim chance of getting on their shelves.

  • After you have proven successful, they will hold you.

*This is why a salesperson with connections into big box retail is the most ideal cofounder or first hire.

• Beware firms promising retail access. If you’re seriously considering this, hit me up and let’s chat.

I recognize that marketing and salespeople will probably read this article and cringe. It’s so easy to poke holes in strategy, or comment with “Well Jim, your problem was _____”.

I get it. I’m not a sales dude. I’ve come to terms with that one.

But if you take anything away from my experience, take this: sales is about relationships and traction, not optics.

You can’t bypass the hard work of connection, selling an idea or vision, or years of established trust and relationships by having a kick-ass brand and product. Most people want to care, but at the end of the day, will move to what’s the most convenient, available, and has the least barrier to entry.

A great salesperson can get your product into the hands of your people and will be the best co-founder or first hire you make.

Wildland manufactured our first round of products in 2018. I had sold my software company at the end of 2015, and wanted to try my hand at launching a physical product as opposed to a digital venture.

Looking back, I recognize now why most people in manufacturing wondered why I would switch from digital to physical, but at the time, it sounded like a ton of fun. Not only could I create a brand that sits on a store shelf, but I could also create products to help people feel better.

Here’s the truth: Physical products are brutal.

We dove headfirst into the world of poison oak and ivy. First, we studied how to remove the harmful oils (Urushiol, btw) from skin. Then we dug into the best OTC methods for relief and healing. Piece by piece, that research shaped what we believed was the ideal product suite for launch.

The next step was figuring out how the hell to manufacture our little idea.

Jargon common to people in the industry was like a brand new language to us. We took the time to learn the key terms as quickly as possible. “Formulation” is what manufacturers call their set of ingredients to produce the product. “MOQ” is the minimum order quantity, signifying the number of units you will need to purchase to get them out of bed to work on your product.

I knew I needed to be fluent in this new language to ensure we received the output we wanted.. We were able to navigate a foreign category to create new, modern, products that worked better than anything previously in the market.

Manufacturing skincare products demystified, we were ready to order and start selling.

Numbers. Numbers. Numbers.

A common MOQ for skincare products is 5000. Two products were $3.50/unit, and the other was $4.20/unit. This put us at roughly $56K for our first manufacturing run of untested products, not including freight shipping, storage, receiving, or any other miscellaneous, unseen costs.

Yikes. It was time to get selling.

In the first couple of weeks, we sold around twenty units. It was a great start, until I broke down the math. Our COGS (cost of goods sold - all the direct costs involved in producing or purchasing the products you sell) rested right around $6.50/unit. The sales came via Instagram, with a CPA (cost per acquisition) realistically around $10 (our spend was about $200-$250). We also started with a flat $5 shipping rate for all sales, to not deter people from purchasing because of the high shipping cost (imagine buying a $20 product and it costing $10+ to ship… ouch).

Looking at all those costs, for this initial campaign (on the low end) we were paying about $18 per unit to sell. Our products are priced between $16 and $24.

Depending on which products were purchased we were either losing money or maybe making a buck or two.

This puts us on track to pay back our initial $56K we personally invested for manufacturing at around the year 2175.

Now fast-forward to a year later, when, through a turn of events, I was able to get our brand into REI. This is the big time, right? Wrong.

They bought a modest amount of product, but instead of paying retail (which we never expected), or even wholesale (50% of MSRP), typical of big box retail agreements they paid less than 40% of MSRP. We also were required to pay for shipping, along with additional random fees applied to us as a vendor. In this case we were maybe making around 50¢ per unit. Awesome.

Reality Check.

I’ll be honest - numbers over the first year hit me pretty hard.

I was used to spending a few months developing digital products, then releasing a solution that would have no COGS to consider, no wholesale discounts, no shipping costs, minimal storage fees, with the manufacturing costs baked into the original creation. If I wanted “more” products, I didn’t have to sink the revenue into making new units, unless I wanted to add features.

Moving into the physical goods realm brought a massive reality check.

Before delving into what these numbers actually meant for Wildland (stay tuned for my next article), I wanted to highlight some considerations that I genuinely wish someone had shared with me before I started manufacturing products.

Things I Wish I Had Known

In no particular order, here are some things I wished someone would have shared with me before I started my manufacturing journey.

• It’s not hard to create a product - just ask the right questions. If you’re curious about what it means to manufacture something, just be a student. Ask questions, learn quickly. Chances are it’s a lot easier than you think.

• Start with the lowest MOQ. Order as if you won’t be able to sell through the initial inventory. It costs more per unit, but you’ll be happy to reorder after product validation has occurred.

• Negotiate everything. All prices are made up by someone, and some salespeople are given the freedom to lower prices, quantities, change timelines, etc. Just try it!

• Don’t overbuild SKUs. We thought we needed the whole product suite to launch, but we didn’t. Identify the one flagship product you feel the best about and start there.

• Merch is a trap. Realistically, company merch will just act as future giveaways, and you’ll never recoup the time and money invested in it.

• 3PLs: wait until Product-Market Fit. 3PLs (third-party logistics companies handling your storage, picking, and shipping) should be viewed as an expense that is saving you time once you’ve hit product-market fit, as opposed to a requirement for launch. They’re expensive, and the wrong one will break you.

• Keystone pricing realities (wholesale vs retail). “Keystoning” needs to be considered when setting your MSRP (retail price of your product). Keystoning is the concept of retail stores doubling the wholesale price to sell in their shop. Shops will buy your product at your wholesale cost (expect 50% of MSRP), while big box retailers will pay between 25-40%, paying you 60 days (and in some cases 90 days) after they’ve receive the product.

• Vet manufacturers and 3PL partners carefully. Find current and older similar companies using their services and ask direct questions about their experiences. For both manufacturers and 3PLs, changing is a lot more difficult than making the right decision from the start.

• Visualize Quantities. It’s easy to order 1000 or 5000 of an item without considering the storage footprint it will take up. Understand what it feels like to store the amount of product you are purchasing - it might force a lower initial quantity.

• Ask realistic questions about your success. What does success look like to you? How much do you expect to sell each year? What does that equate to financially? How many units do you need to sell within a certain timeframe to make it a full-time job? Understanding these metrics helps attach realities to your venture.

If you’re like me, you love solving problems. Creating an outdoor skincare brand then manufacturing products for that brand was a problem to solve, and I solved it.

In hindsight, I wish I would have taken a step back and asked more questions. I wish I would have started slower and smaller, vetting the poison oak and ivy skincare market, along with my manufacturing and 3PL partners more.

More than anything, I wish I understood the meaning of manufacturing and selling a product as an independent business more deeply. Although there was nothing astronomically bad about this first round of manufacturing, some of these initial decisions set the stage for future losses.

If you are thinking about manufacturing your first products, learn from my mistakes. Take your time, vet partners, start small. This will help you build a lasting brand and business.

I’ve founded quite a few companies in my life. Some found traction, a few even had exits. Others, like my skincare brand, Wildland, were a train wreck in slow motion.

Here’s the thing: the lessons I remember most didn’t come from the wins. They came from painful, expensive failures. And while I wouldn’t wish that experience on anyone, I also know most founders will face their own version of it.

With the recent timing of Wildland’s close, I have been processing all of the good, bad, and damn, why did we do that - and thought it could be a great opportunity to share the practical, hard-earned lessons I wish someone had handed me before I sank years (and plenty of cash) into this venture. Think of it as field notes from the trenches of building a physical product company: what worked, what didn’t, and the blind spots that nearly every founder has to fight.

Over the next few posts, I’ll unpack what I learned about:

1. Spotting blind spots early (today’s post)

2. Manufacturing and product realities no one tells you about

3. Why a sexy brand won’t save you without sales

4. My big-picture takeaways about what kinds of ventures I will (and won’t) build again.

If you’re thinking about starting a company, especially one with a physical product, I hope these stories save you some of the heartache (and cash) I went through.

So let’s start with the biggest blind spot of them all: the hidden cost of falling in love with your own idea.

If you told me at a dinner party, “I just shut down my startup. I’m a failure,” I’d stop you right there.

“You’re not a failure. You did something millions of people only dream about: you took a swing.”

But here’s the catch: when it’s your company and your mistakes, it doesn’t feel that way. I know, because I’ve recently been there.

The Wildland Story

A few years ago, I started Wildland, a skincare brand focused on poison oak and ivy. The gap seemed obvious. The market leader was Tecnu, a product literally invented in the 1960s to wash off nuclear fallout. When we dreamed up Wildland, outdoor recreation was booming, DTC brands were exploding, and I thought: Perfect. If we build a better product and a better brand, we will own this space.

That was my blind spot.

The real competitor wasn’t Tecnu, a fifty year-old brand in the space. It wasn’t some new startup in stealth mode. It was people doing nothing.

Most folks who come into contact with poison oak or ivy don’t wash the oils off at all. If they get the rash, they just raw dog it and try things like calamine lotion (which does nothing, for the record) or a homemade remedy. We were solving a problem most people didn’t even recognize as worth solving.

I’ve spent 20 years in design and brand. I love the work. I care about polish, intention, and the details most people overlook. But when you love craft as much as I do, it’s dangerously easy to assume those things will carry the day.

They don’t. Customers don’t buy polish, they buy a true solution.

At Wildland, we went all-in on building a great working, sustainable product along side a beautiful brand. We even sent merch to outdoor influencers with millions of followers. Great photos. Zero sales. Turns out people don’t impulse-buy poison oak wash.

What I Learned the Hard Way

Two years and around $120K later, the lesson was painfully clear:

If you have to convince people that a problem exists before they’ll care about your fix, you’re not in a product business. You’re in the missionary business.

That’s a much harder road.

A Better Question to Ask

If you’re building something new, take a moment to ask yourself:

• What assumptions am I making about my product and market?

• Am I mistaking my own enthusiasm for demand?

• Is my real competitor indifference?

Blind spots aren’t obvious until they’re expensive. Better to catch them now than after two years of fighting the wrong battle.

Why This Matters to Me Now

Those blind spots cost me time and money. It’s not just about making something beautiful. It’s about creating something people will actually use.

And that’s a lesson worth carrying forward.

Next up in this series: the nuts-and-bolts lessons I learned about manufacturing and product development — the kind that will save you time, money, and heartache.

If you spend any time on LinkedIn, you’ve probably seen the word “fractional” pop up in people’s bios: Fractional CMO, Fractional COO, even Fractional Head of Design. The use of the term has exploded, from around 2,000 people in 2022 to over 140,000 by the end of 2024.

But what does “fractional” actually mean?

At its simplest, a fractional is an executive-level leader who joins a company part-time or project-based, bringing strategy and direction without the overhead of a full-time salary. In the past, you might have heard words like “consultant” or “interim.” The difference now is that “fractional” signals something more embedded and accountable, not a one-off advisor, but a leader who becomes part of the team for the season they’re needed most.

The model is growing fast. Fractional executive roles have increased by 57% since 2020, especially in startups where leadership is critical but budgets are tight. More recently, mid-size and enterprise companies are adopting the approach too, with nearly a third bringing in fractional leaders to complement their existing teams.

The message is clear: the fractional leader is here to stay. And it matters.

Here’s the hard truth: most leaders reach a point where they need expertise outside their own wheelhouse. The default solution has often been to hire an agency or make a full-time hire. Both options come with baggage. Agencies optimize for their own profit, and full-time hires add long-term cost and risk.

Fractionals sit in the middle. They bring deep, time-tested expertise and work alongside you, but without the long onboarding curve, inflated promises, or commitment of a full-time exec. And if it’s not working, you can simply not renew the contract. No messy HR process required.

I Learned This the Hard Way

For me, the gap was marketing. Over the years, across all my companies, I’ve cycled through five separate agencies, each one promising results and each one quietly underdelivering. Each time we’d spend six months burning tens of thousands of dollars before sending the breakup email and swearing off agencies… until the next time.

Hiring full-time didn’t solve it either. Each time bringing in marketing directors, hoping they’d at least cover their own salaries. They didn’t.

What I needed wasn’t another agency deck or another employee trying to hang on until payroll. I needed experienced leadership that could set strategy, align the work, and see it through. That’s what fractional leadership provides.

I Believe in This Model Enough to do it Myself

As a fractional design leader, I embed with companies at different stages, sometimes helping a startup launch with systems that feel cohesive from day one, sometimes guiding a legacy brand through the messiness of finding focus again.

My clients get executive-level brand and design leadership without adding another full-time seat. More importantly, they get someone who isn’t there to chase awards or sell hype. I bring decades of experience, a craft-first approach, and a calm presence that keeps the work grounded in what actually matters: clarity, cohesion, and trust.

So, What Does “Fractional” Mean?

It’s leadership without the baggage.
It’s expertise without the overhead.

And at its best, it's a partnership that feels embedded, human, and real.

Most companies don’t start with a design founder at the helm. Tech companies are started by engineers. Healthcare, finance, and education companies are usually led by subject-matter experts. Unless you’re launching a clothing line or retail brand, design is often treated as decoration, a logo, a color palette, and maybe a brand book that quickly gets buried.

That approach works in the beginning. When you’re proving an idea, survival matters more than polish. But as companies grow, something shifts. Ten years in, what once felt fresh now feels fragmented. The startup energy has hardened into legacy, and the brand starts to show its age.

Competitors look sharper. Internal decks are a mess of old logos and clashing templates. Customers and employees start to feel the friction. The brand feels less like a signal of strength and more like a liability.

And here’s the truth: what makes or breaks a legacy brand isn’t a new color scheme or tagline. It’s design leadership.

It Matters to Customers

Customers don’t stay loyal to brands that feel careless. Post-pandemic, 75% of U.S. consumers tried new shopping behaviors, and over a third tried new brands. In other words: people are open to leaving.

When they do, the top driver is experience. One study shows 80% of customers who switch brands cite poor service. Another shows 86% walk away after just two or three bad interactions.

I saw this firsthand with payroll software. An accountant steered me from Gusto to Paychex. The experience was painful: multiple portals, endless phone calls, and a confusing tangle of inconsistent logos and outdated design. After two weeks, I canceled and went back to Gusto. The difference wasn’t just features. It was clarity, consistency, and care.

A legacy brand without design leadership shows its cracks and drifts into irrelevance. Customers notice. And they leave.

It Matters to Employees

Brand isn’t just for the outside world. Employees feel it too. Studies show they’re 2.2x more likely to stay when they’re proud of where they work, and 6x more likely to recommend it.

When the brand feels broken, employees disengage. It shows up as confusion about templates, embarrassment about sending out dated decks, or hesitation to share a campaign on LinkedIn. Over time, it becomes a culture of apology instead of pride.

If people inside the company are making excuses for how the brand looks and feels, leadership has a design problem, not just a marketing one.

It Matters to Stakeholders

Strong branding doesn’t just look good; it drives business outcomes.

B2B companies with strong branding see a 20% higher success rate.

90% of customers expect a consistent experience across channels.

Brand consistency alone can boost revenue 10–20%.

Consistency, trust, and clarity aren’t accidents. They’re the result of design leadership embedded in decision-making, not just an afterthought.

What Design Leadership Really Means

Too often, companies reduce brand work to hiring an agency for a new logo, a campaign, or a website refresh. Agencies hand over a “brand bible” that ends up collecting dust.

The data is clear:

Only 25% of organizations enforce their brand guidelines consistently.

More than half produce materials that don’t conform to their standards.

Guidelines without leadership are just documents. They don’t change culture. They don’t protect equity. And they don’t evolve with the business.

True design leadership is different. It means embedding design into the company’s goals, culture, and strategy. It means aligning how a business wants to grow with how it shows up in the world, externally, internally, everywhere.

When empathy and craftsmanship guide the brand, guidelines stop being rules and start being lived behaviors. That’s what keeps a legacy brand alive.

The Luxury of a Design Founder (and How to Get Close)

When I co-founded a software company out of a design studio, the brand was always on my mind. I scrapped what didn’t work, refined what did, and kept the brand aligned with who we were becoming. That’s the advantage of having a designer as a founder: the brand doesn’t get left behind; it’s always in the front seat.

Most companies don’t have that luxury. But they can have design leadership, someone who treats brand not as a deliverable, but as a living system that grows with the business.

Don’t Wait Until Next Year

Updating a legacy brand can feel daunting. But delaying it only makes the gap wider between who you are and how you’re perceived. Every month without design leadership is another month of erosion, of relevance, trust, and pride.

The companies that thrive are the ones that invest in design leadership early. They create the groundswell, not get buried by it.

A Quiet Invitation

If this resonates, I’d love to talk. Not about a rebrand or a quick campaign, but about what design leadership could mean for your business. Sometimes it’s embedding with your team as a fractional Head of Design. Sometimes it’s guiding a specific initiative through my studio, the Industrious.

Either way, the goal is simple: keep your brand alive, intentional, and something people are proud to stand behind.

Nice work, Cracker Barrel - you tried.

I normally don’t pay attention to public brand identity changes or missteps, since most of these major household brands have developed enough equity to withstand questionable changes to their marks.

Cracker Barrel’s current mark has been around for roughly 50 years and is a recognizable fixture for its restaurant chain. The current logo is pretty rough, with an old white dude (Uncle Herschel) on a rocking chair, leaning his arm on a barrel. Even aside from the racial jabs the name itself might evoke, having an old white guy leaning on a barrel in the logo is definitely the wrong look in 2025.

CB’s internal instincts were right - it is definitely time for a change.

But instead of enhancing and upgrading their mark to better represent their legacy brand with 50+ years of heritage, they moved to the “say nothing but feel updated” mark, now typical of large corporations.

After the release of their new, shiny, neutered mark, the internet was up in arms as usual. Most were complaining about the presumed bastardization of the heritage of Cracker Barrel itself, and that this move was a mistake, even having the CEO of Shake Shack chiming in that they need to change back because they were “erasing their heritage”.

So they did.

I remember seeing that tweet and feeling frustrated with Cracker Barrel. Making a quick, off-the-cuff decision is one thing. Spending months on a rebrand, then rolling it back the moment negative press hits, is another. Whatever respect I had for the brand wasn’t lost on the new logo, it was lost on the reversal.

Jaguar experienced the same backlash, but hasn’t backed down.

Their more recent rebrand at the end of 2024 was met with the same internet uproar when they released it (along with their “Type 00” concept car showcasing this new electric-forward, modern aesthetic).

Same story, more intense consequences.

Although this logo change/change back potentially brought more publicity than either Cracker Barrel or Jaguar have received in the past 3 decades, there are some lasting takeaways that are worth exploring when thinking through a brand, a rebrand, and company leadership.

A brand is more than a logo.

As annoyed as I might be about the internet having such strong opinions about a logo change for a car I will never drive or a mediocre breakfast chain, it’s good to call out that the emotional uproar is rooted in the perceived destruction of legacy brands that have been built on nostalgia. People weren't heated because they felt like the colors sucked, the typeface was off, or the general artistic direction, but because it felt like it was stripping off its legacy.

Heritage brands (brands with history, longevity, and cultural or emotional resonance) have a unique burden when entertaining a rebrand. There are childhood memories and experiences baked into those institutions that need to be addressed when considering a rebrand. Legacy brand updates can definitely be done (and done well), but it’s a delicate task. The rebrand needs to creatively acknowledge the past while modernizing and representing the future of the brand.

For these types of brands, change in marks and identity must be a conversation, not a monologue.

McDonald's is a great example in the same category as Cracker Barrel, of a brand that has pulled this off:

In the automotive industry, there are plenty of examples of a slow, intentional progression and rollout of updating marks:

Update for the right reasons (and stand by your choice)

CB’s new logo lasted 1 week long before leadership reverted to the previous logo.

Launching a new logo, then reverting it back after 1 week allows me to make a few assumptions:

1. They felt pressure to update to increase sales and reach a lower aged demographic.

2. They trusted an agency, presumably with very little design direction.

3. Stakeholders were never invested in the reason behind the rebrand, thus reverting the second they received negative pushback from the internet.

Design is hard, especially when stakeholders are not clear with desired outcomes or expectations.

If CB’s motivation for a rebrand was to increase sales, the only way to judge if the rebrand was successful is to examine if there was an increase in sales post-update. Seven days is not enough time to judge if this change drove sales.

This means stakeholders didn’t believe strongly enough in their purpose behind the update to withstand negativity, or, the agency went rogue with their interpretation of the brief and somehow pushed the change without Cracker Barrel’s approval. My bet is on the first, not just because I’m a biased designer.

In Jaguar’s case, motivation was a positioning decision. Jaguar was hoping to expand their market into ultra-luxury, electric vehicles. Instead of simply rolling out a model or two that fit this bill, they decided to throw all their eggs into the “luxury modern electric car company” basket. As an already polarizing brand, Jaguar’s decision to switch positioning further segmented its limited customer base, leading to a 75.1% drop in sales in Europe, with just 2,665 cars sold. Oof.

I will say, in retrospect, that I have much more respect for Jaguar’s choice to stick with their mark, rather than reverting back to previous marks like Cracker Barrel. Their entire strategy (not just rebrand but manufacturing changes, etc.) is an $18B, multi-year investment. They are moving forward even with the immediate pushback, presumably because they believe in their vision. Stay strong, Jaguar! I’ll still never own one of your cars, but I’m proud of you.

All this to say, if you believe in your reasoning, own the outcomes. Let them drive your decisions, not a moving target like the internet.

Hire design leadership

Great design leadership begins with empathy.

Empathy is the ability to understand and connect with another person’s emotions, thoughts, or perspective. Strong design leadership relies on that same skill, anticipating how people will experience a product or brand and how they’ll respond when it’s put into the world.

There is a common idea (especially with larger companies) that simply hiring an expensive, well-known design agency will solve any brand or positioning problems they might have (*cough* Cracker Barrel *cough*). The idea that if enough money is spent, these companies can just hire out for campaign and asset creation, bypassing design leadership altogether.

Unfortunately, this is the equivalent to hiring a builder to construct a house without any direction. They would probably make something semi-cool, solidly constructed, accomplishing the goal of building a house… But in reality, the home would not be your home. It wouldn’t have been built with your distinct needs and tastes in mind. It would just be another, presumably well-constructed house.

Now picture the same scenario, but with an architect involved. You’ve shared how you plan to live in the house, your tastes and preferences, even the fact that you can’t stand open kitchens because the dishes tend to pile up in your household. When the builders execute on the architect-delivered plan, you’re confident the result will be more than just a solid structure. It will reflect your point of view, ethos, your taste, and your lifestyle, meeting your needs in the way you want them met.

Design leadership is the architect of your strategy.

You’ve established your positioning and organizational goals, and you need someone who can craft the plans to accomplish those objectives while considering your company and client’s point of view, taste, and lifestyle. Great design leadership will accomplish this, creating a blueprint to success.

Outsourcing design to an agency without the proper leadership will fall flat most (if not all) of the time. Not because the agency is bad at its craft, but because no amount of money will create the clarity and direction a design leader rooted in the goals of the company will bring.

I’m not here to hate on Cracker Barrel or Jaguar. Like I wrote earlier, design is hard. Especially when you do it for publicly traded companies with immediate criticism just one click away.

Heritage brands like this have a greater responsibility to their customer to communicate the process more than a startup or smaller company. Especially in cases where motivations are financially or positionally driven. These companies have the burden to respect the company’s nostalgia and history, leading customers through the change rather than simply dropping it on them, hoping for a positive reaction.

With the right plan and design leadership, each of these examples might have earned a better reaction. Empathy in the approach often matters more than the assets themselves.

“Don’t talk about it, be about it.” - 2Pac

Don’t you love articles that start with a quote? I typically hate them, but when the line comes from one of the greatest West Coast rappers of all time, I’ll give.

This is when we stop talking about how to name your company and jump headfirst into the ‘be about it’ realm. Putting pen to paper, rubber to road, and nose to grindstone.

This article will be a bit different than the last couple in the series. It will be a walkthrough on the steps to take to find your name. It will act as a practical application of the foundations in Part 1 and Part 2, ideally leading you step-by-step through finding your brand-new, wonderful name.

Preparation

Before you start writing anything down, you will need to make sure the foundation is set, ready to discover your company name. Readiness comes when you are mentally and physically locked in, having the space to do the work.

The first step in mental preparation is to have the foundational knowledge top-of-mind, ready to explore concepts, themes, and moments related to your new venture.

Know thyself

Chances are, if you are the one charged with naming this company, you are more than likely the founder, product builder, service executor, and/or CEO. This means your opinion matters more than anyone else’s - even when it comes to your customers’ perceived tastes.

A few years ago, we were creating clothing merch for a company I started, and were at a bit of an impasse about which stylistic direction to head. While trying to decide on which designs to go with, my business partner at the time asked me, “Would you wear it?”

My quick answer was “No, but our people might.” To that, he said, “Let’s make something you want to wear. If you’d wear it, they will too.”

That was a pivotal moment for me. The reality is that designing for what you think people want is a dangerous game, and typically ends in boring and lifeless outcomes. In contrast, designing (or in this case naming) for your personal taste has the highest chance of resonating with the leaders in your audience as well as making you happy as you live daily with your brand.

Mental preparation begins with being confident of who you are and your place in your niche. You are closer to the problem you are solving than 99% of the people in your market; enough to create a company around creating a solution for God’s sake. The work of being in tune with your opinion and tastes is the most valuable preparation you can make.

Know thy people

Having a deep knowledge of the market you are entering is also key before beginning the naming process. Understanding your market’s primary demographics, age, income, education, as well as where they like to hang out (both physically and digitally) is invaluable knowledge.

In addition, spend some time identifying what other brands have weight and affinity with your demographic. These can be brands inside and outside of your given market, understanding and discovering the threads that connect your people to these companies and their values.

Know thy environment

You will need space to work.

The only way you can make creative progress is by carving out space to dwell on the problem. This might mean a weekend away at a hotel, booking a conference room for a couple of days, or maybe some headphones and white noise in your living room. You need to carve out the space to think.

I also like to encourage people to use a pen and paper.

The act of placing pen to paper tends to connect me a bit more to the ritual, but I recognize everyone is different. The most important thing is that you feel freedom to record and curate ideas with focus, without distraction, TikTok, or insecurity getting the better of you.

Ok, onto the practical steps.

I’m going to fly through these steps in this article, but know some of these will take 10 minutes while other steps might take days.

Step 1: Brain Dump

I like to set up a sheet of paper into two columns. One side is “names” and the other is “themes”. The names side is where I capture anything that _might_ work as a name, and the themes column is where I drop in any concept, words, or thoughts to further explore.

Goal: Get it all out. No filter, no curation or revising (yet). Just drop everything into one of the two columns.’

Ideal Amount: 20-30 names + themes

1. Back of mind names: Assuming you have been thinking about this company or offering for some time now, I can almost guarantee you have been thinking about your brand’s name to some extent. There have probably been some names you have already floated to friends or family that may (or may not) have been received well. Write them all down in your names column.

2. Themes and concepts: How have you been describing your new company? You have presumably been talking about how powerful or unique your idea is - what specific words have you been using in conversations? Do you find that you have go-to phrases that perfectly describe your new company? What about moments or activities that happen in your market? Write those down, along with any verbs (action words) or adjectives (descriptive words) that come to mind in your themes column.

3. Anything and everything: Let your mind wander. Move from practical to impractical, conceptual to weird. Write down everything that pops into your mind.

Step 2: Build List

This next piece is probably the toughest part of this process, where you want to turn your creative dial up to eleven. It’s where we take themes and concepts and shift them from the theme column over to the names column. Remember, during this step we are still not removing anything. We are simply evolving themes or concepts into potential names on our name list.

Goal: Shift all themes and concepts over to the name list.

Ideal Amount: 20-30 names

1. Start with Synonyms: Most of my names develop from a theme or concept moving into the name list by deep diving into synonyms for those words. Practically, I love to use Thesaurus.com. I’ll drop a word in there and continue to click and follow synonym trails until potential names emerge.

2. Follow rabbit trails: Learning to recognize when words or concepts excite you is key to finding a great name. Sometimes it’s the meaning, other times it's the shape or look of a word. Keep pushing and start noticing why you like certain words over others.

3. Alternate Spellings? Smashed together or made-up words?: I get nervous throwing alt spellings out as an option, since it takes a combination of market intelligence and finesse to pull it off. But brand history is full of these types of words that have become household names (Kleenex, for example). It’s tough to pull it off in the era of people searching for you on the www, but it definitely can be done!

Step 3: Refine

This is where our thoughts and ideas start to come into focus.

Ideally, at this point, we have anywhere from 20 to 30 words written down on the name list, presumably with our new name buried in there somewhere. Now we just need to allow it to emerge!

One key thing to remember during refinement is that once you decide to remove a name from the list, don’t look back. It’s tempting for some personalities to make a decision, only to end up overthinking then regretting it. If you get to the place where you choose to remove a name, know that it is the right call! Only move forward from there.

Goal: Clean the list to only have viable names (or names you’d be proud of) leftover.

Ideal Amount: 2-3 names

1. Immediately ditch: At this point there are names that you look at and mentally eye-roll. You probably second-guessed even jotting those names down in the first place. Cross those off your list.

2. Immediately ditch, part 2: Are there any standouts with hard spellings or concepts that will be lost in your market? See ya later, dumb names.

3. Next level throwaways: What names are there that you just aren’t into? Maybe the concept is right, but the word looks wrong or is tough to spell.

4. Vaguely familiar: Sometimes when choosing potential names, we can get a little too close to the original inspiration. Are there any names on your list that are too close to other companies in your market? How about in parallel markets? If you think they might be too close, they probably are. Ditch those bad boys.

5. Last gut check: At this point, you might have around 5-7 potential names. We need to get you down to at least 2, or maybe 3 solid names. Which of these names do you like more than the others? You probably have a couple of favorites at this point, so remove all except those. Trust me, you’ll come to the same conclusions whether or not you make this call immediately or wait a couple of weeks to stew on it.

Step 4: Choose your top 2 names

You’ve done the work, and now you’re looking at 2–3 bangers, any of which you’d be proud to carry into your future endeavor. You can trust that by moving through this naming process, you’ve gotten the best outcome you possibly could. The names are authentic to you and your market, and they feel timeless and easy to communicate.

Goal: Choose your name, maintain one for backup.

Ideal Amount: 2 names

How do you decide what the name will be?

1. Go with your gut: I’m a big believer that even though sometimes we don’t have words to explain the “why” behind a decision, sometimes our bodies just know. This is one of those cases when you have to listen to your gut. Which of the 2-3 names do you like the most?

2. Real world test: One of the most impactful real-world applications of a name is in your company’s URL choice. The URL is typically informed by your name choice. If you find yourself between 2-3 names, start brainstorming your URL/email address. Make sure a decent choice is available by using instantdomainsearch.com for quick assessments and options. Remember, it needs to be easy to spell, easy to find, and not super long. Also, ideally land on a .com if possible. Even if you somehow can get “cars.xyz”, that will be a tough one to communicate to your audience since 90% will head to cars.com first.

3. Check USPTO: If you are bouncing between names, do a broad search in USPTO.gov to check the trademark database to see if there are any potential conflicts with your names. You might find that one of the three is super close to another company in your market and cannot use that name, which can help your decision along. Or, you might find that there is nothing even close to your favorite name, giving you confidence to move forward.

4. Ask 2-3 people you trust (but only if you have to): I know in the startup world, asking for customer feedback is a key part of the process. Be careful who you ask opinions from in cases like naming, realizing they aren’t nearly as close to the process as you have been. I sometimes like to use others as a sounding board to help me recognize what I actually want. Sounds a bit weird, but I try my best to pay attention when I receive feedback, noticing what I wanted them to say, rather than what they actually said. This allows me to identify what I really wanted all along, rather than what they prefer. Either way, ask the question but don’t let their answers send you back to step

Make the call!

Now you are ready. Lean in and own it! This is the name for your new company, and you should be able to sell it to any audience.

Back-up?

Use the next closest name you didn’t choose for a backup name. Keep the back-up close to you, just in case we find out down the road that you are unable to trademark your name, or uncover out-of-the-blue naming conflicts.. Sometimes you need to fight for your name, but it’s nice to have a backup just in case.

Oh, and be sure to purchase the URL for that back-up name while you’re at it. You can always choose to not renew it if you get the TM for your name, but it’s comforting to have it in your back pocket.

Last things to remember.

Here are some practical thoughts as you think through this naming process. Especially for first-timers, we just don’t know what we don’t know! Hopefully, these give you some context and a little bit of freedom as you live with your naming decision!

1. You don’t need to use your corporation's name for your product or service: Many companies use their product name when speaking about their offerings versus their corporate name. Don’t get too hung up on the company name if you are planning on selling a keystone product. It matters, but most people will be looking for your product, not your company.

2. Trademark ASAP to make sure there are no infringements: If you’ve landed on a solid name, spend the money with a decent IP attorney to help you trademark as soon as possible. This will put you at ease that your name is unique (and yours), as well as raise any red flags of potential infringement before you get too far down the road in your market.

3. Your opinion will always matter the most: There will always be haters. As a designer, I have learned the art of listening to opinions, taking what’s helpful, then ditching what isn’t. I call it “eating the meat and spitting out the bones.” Typically, people’s opinions are rooted in some form of truth, but when it doesn’t resonate with your truth (especially in the case of naming) spit it out.

Congrats on your new name. Be confident and build something magnificent.

Now is the time. You’ve been doing the real work. And if you’re still holding out for the flawless name to reveal itself… it won’t. It’s time to decide. You know you now have to put in the work.

So, what does “putting in the work” look like when determining a name? Is it an isolation room with a whiteboard for a week? Is it walking along the beach until an epiphany hits you square in the face and the universe reveals what was always your company name? Is it simply asking ChatGPT?

The reality is that although most entrepreneurs and founders have strong opinions when it comes to their solutions, most do not consider themselves “creative”. This means that they tend to punt in situations like brand, design, and naming, making use of an LLM like ChatGPT or Grok extremely tempting when trying to uncover a name.

Here’s the truth: naming is a muscle you can develop. And just like any muscle group, the more you work it out and develop it, the better you will get.

It’s like skipping training and expecting to run a marathon - shortcuts might get you to the starting line, but not across the finish. When we default to AI as a shortcut for our creative output, outcomes are the exact opposite of “creative”: impersonal, generic, and lacking any glimmer of soul.

Why putting in the work matters.

Listen. I am the king of shortcuts. I once convinced my girlfriend in college to bypass the trail to hike directly up the side of a mountain to save time. I also learned that I could take 21 units a semester and still get a 2.7 average while doing the absolute minimal amount of homework. BA in 3 years, baby.

If the outcome of the shortcut brings the result you want, by all means, take it. Unless you simply love the process, it’d be silly not to. But if the shortcut takes you up a side of a mountain through thickets of Poison Oak, trust me, the juice isn't worth the squeeze.

Defaulting to AI for creative outcomes is a shortcut with a cost.

If you want the best possible outcome for your name, here are the reasons why I think putting in the work is required to give your new company the right name.

1. Creativity requires a point of view.

What makes great art isn’t necessarily the outcome or enjoyment of that medium by the consumer, but the expression and point of view of the creator, uniquely telling their specific story through their specific lens.

I recently heard a quote from Rick Rubin about AI art:

“The AI doesn’t have a point of view. Its point of view is what you tell it. …You can have a great script for a film, give it to five great directors, and you’ll get five completely different films.”

When choosing a name, the primary fuel must be your taste and values, framed by your point of view. Whether you consider yourself creative or not, an authentic expression of your experience is the right name for your company.

A name shaped by your lens will always be distinct.

2. Working for it makes it more meaningful

In 2008, I launched my first SaaS product. The monthly fee was low, but the buy-in cost was intentionally high. Our assumption was that if customers paid a big upfront fee, they’d be more committed, ultimately leading to a higher customer lifetime value. (CLV).

Turns out we were right.

Over our eight years of running the company before our eventual sale, we experienced exponential annual growth with very limited cancellations. Once bought in, the high initial fee forced them to commit the time needed to ultimately find the value in our solution, in turn finding longevity with our product.

Putting time and work into naming your brand (as with most things) will inevitably produce a higher level of commitment, buy-in, and pride when sharing your company with others.

In these beginning days of the AI revolution, it’s super easy to jump all-in without analyzing what is lost in the new processes. We brush past much-needed growing pains for the sake of time savings and output. Although this might benefit some crafts, if not used with the correct restraints, AI can be destructive to the creative industry.

The work of storytelling and meaning in your creative processes is always worth the work. Even if the work you put in is only known by you, your passion and POV always translates to the customer.

Use AI to refine (rather than create)

I’m not saying you should stick your head in the sand and ignore AI.

AI is most powerful when used as a tool for a specific purpose. Use an LLM to help refine your thoughts, ideas, and language to give you the best outcomes throughout this naming process. Used the right way, AI can be the key that opens a door to new memories or threads of ideas and thoughts that could reveal the foundations of your brand’s name.

Feel free to use AI, but use it to encourage your creativity rather than replace it.

Remember how easy it used to be to name things?

I remember creating my Wu Tang Name in 2004, and was so pumped when the generator gave me "Childish Gambino". It perfectly embodied my child-like nature along with my suburban white boy/gangster side.

In retrospect it seems like others might have received the same name:

Whether you're finding a name for your new rap persona, or attempting to name your shiny new start-up, naming is hard work.

For the weird ones, this is the most exciting time in a company’s life. It’s like choosing the name of your newborn (or puppy, for the sane in the bunch). You’re deciding how humanity will talk about your shiny new baby, for the long haul.

For others, it’s a moment of dread. The fear that one wrong name will doom every future mention to a chorus of giggles and a side of cringe. Imposter syndrome shows its beady little eyes, and insecurity kicks into overdrive.

After around 20 years of experience starting and naming brands and products, I’m convinced that with just a little time and elbow grease, anyone can find the right name for their company. My definition of the “right” name is one that is authentic, true to market, and timeless.

Authenticity

A good friend of mine in the early 2000s was a bassist for some pretty well-known bands. We were living in LA at the time, and I loved that each time I got to hang with him, I heard the latest “insider” information of what it was really like to play music for a living. Spoiler alert: it really, really sucks if you are not the 0.001%.

One thing I would notice every time we hung out was that his clothing choices would change depending on which band he was playing with. If he was playing in a pop band, he would dress more mainstream and trendy. Indie bands would push him deep into the bargain bin of a thrift store. But the moment that stood out the most was when he stepped out of his car wearing a full-on white fur coat and cowboy boots. He was in a rock band that had a great time on stage, giving off major 70’s Hollywood rock-n-roll vibes - thus the “screw-you PETA” fur.

I remember wearing my Urban Outfitters graphic tee at the time, looking at the wind blowing in that beautiful synthetic fur, questioning every fraction of my insufficient fashion sense. As we walked into the coffee shop, I distinctly remember saying “Bro. I LOVE the fit. How do you pull it off so confidently?”

I’ll never forget his answer: “You have to wear it like you own it.”

His answer made little applicable sense at the time, which only reinforced his rock’ n’ roll brand. After nodding my head like I understood, I walked my skinny jeans-wearing ass into the Coffee Bean to get the latest updates on the music industry.

Fast-forward to me now, in my mid-40s, with a closet full of fur coats. Just kidding. But I will say the statement of ‘wearing something like you own it’ rings more true than ever before, especially as I reflect on my career journey as a designer and brand builder.

The most important part of any brand is authenticity.

99% of humans feel like they are behind the emerging cultural curve within our given crafts. If you are lucky enough to feel like you are that 1%, chances are either 1) you don’t have an internet connection, 2) you’ve only shared your ideas with your biggest fan (mom), or 3) you’re lucky enough to be born at ground zero of your particular craft, where your market’s culture and trends are born.

I’m still not convinced that #3 even exists in this post-internet age, but I digress.

If you're part of the 99%, I've got some news for you: you've got everything you need to confidently wear that fur coat.

Authenticity is the great equalizer. It has always been.

When embodying your brand (whether in a name, marketing, product suite, customer relationships, etc), authenticity resonates more than any other factor. Each of us would rather have an honest and transparent friend over a popular one. In the same way, we want to support and cheer for brands that have remained true to who they are, trends be damned.

When choosing a name, begin with authenticity. It’s what we want from you, and it will be a brand that will continue to grow and emerge with you, easier to sell, easier to grow, and much better for the world.

True to Market

The car industry is prolific when it comes to missing the market when naming their products.

Here are a few you might or might not have missed:

• Audi “E-tron”: “Étron” in French means crap.

• Honda “Fitta” (later “Jazz”): Vulgar slang for female genitalia in Swedish and Norwegian.

• Mitsubishi “Pajero”: Common insult meaning “wanker” in Spanish

• Toyota “MR2”: When spoken in French, it sounds like “merde” which means “shit”.

Or remember Trader Joe’s internal brands like “Trader Ming’s” and “Trader José’s”? That’s a great idea if you forget the majority of TJ stores are concentrated in California, where we’re proudly known for our DEI efforts. I know these brands have been replaced in most of the stores in CA, but apparently not everywhere!

Obviously, these examples are the extremes. The tone-deaf accidents that result from not enough research, or good ideas gone really bad. So, my best advice is don’t do that, K?

But there are more obscure, harder to pin down examples that we interact with almost every day. Some of the ones we know that have worked, and naturally become giants in their space, despite their name. Brands like “Slack” promote workplace productivity (which, ironically, is an acronym for “Searchable Log of All Communication and Knowledge” - betcha didn't know that). Or even “Discord,” which provides connection and communication for gamers, despite the word meaning distress or dissonance.

As a dad of 3 daughters, I have recently run into Drunk Elephant, a luxury skincare brand sold in Sephora. Apparently Drunk Elephant falls into the “OMG Dad, you don’t know about [insert brand name]??” category with my girls. Once again, the brand’s popularity presumably rose due to the absurdity of the brand name initially, even in a crowded market like cosmetics, where name weirdness is normalized in hopes of standing out and (ideally) being remembered.

Each of these examples worked well enough to be market leaders, but I’d argue it was product and timing-driven success rather than a brand win.

The opposite is true when choosing a great name.

Some of my favorite brands embody a great understanding of their market and consumer. They create as segment insiders, rather than some PE firm that needs to find a cool, made-up name that still has a .com domain available.

The first example of this is Vacation Inc.

Vacation is a sunscreen brand launched during the pandemic in 2021 by three guys, one of whom (Marty Bell) previously created Poolsuite, a web radio station providing vibey jams for you while vacationing poolside in Miami or Palm Springs.

Vacation’s product suite is an embodiment of their target market. 20-something’s enthralled with late 80’s dreamy beach-vibe aesthetics, ironically a time period they never actually experienced. Their name and brand are exemplified in the ultimate leisure experience: sitting poolside, having cocktails, all while listening to vibey music and getting a tan. Products like Chardonnay Oil and Classic Whip Sunscreen Mousse Cream, accompanied by photography and an Instagram timeline with images that are indiscernible from photos from the late 80s.

Every aspect of their brand is saturated in the concept and values of their name, Vacation.

I give it a branding chef’s kiss.

I have a lot of the same feelings about Teenage Engineering. This Stockholm-based electronics company builds synths, speakers, and other gear for musicians and (primarily) Teenage Engineering brand enthusiasts. Their complex, unique products perfectly embody their name. The combination of Swedish craftsmanship and love for symmetry is obvious in every product, but always somehow combines a level of playfulness your 14-year-old self would have loved. Pocket synths like this and EP’s like this exemplify their brand. You don’t have to be a synth head to be a fan of Teenage Engineering.

Names that are authentic to the creator, while expressing the hopes and wants of their specific market as an insider, are gold. And honestly, very rare.

Let’s translate this to you, practically.

Next to finding a name that is authentic to you as a creator or founder, finding a name that is true to your community’s goals and values is essential.

So keep it real, and don’t be a “Pajero”.

Timeless

Remember fedoras? Around 2007-2010 blessedly gave us the resurgence of the fedora, gracing red carpets and high school reunions alike. From Justin Timberlake to Jason Mraz, the fedora was unstoppable as the headwear of the stylish.

Or how about wearing a bowtie instead of a traditional tie? Nothing says ‘quirky-formal” like a bowtie in the 2010’s. Guilty as charged with this one. (I would post a pic here if it didn’t hurt so much).

How many people launched brands and products with an “i” in front of them in the early 2000’s? Thanks for that one, Apple. Got Milk Originality?

Trends come and go. Best not to be caught with your pegged pants down.

We all have followed trends that didn’t last. Some of us even have photos floating around reminding us that bleached hair made us look more like Draco Malfoy than Adam Levine. This lesson is the same with naming brands and products.

Here are three reasons why simple and classic is always better than trendy when naming a brand.

White shirt, blue jeans, and wayfarers.

The classics never go out of style. Good, solid names will stand the test of time, and at brand launch will remarkably feel like they’ve always been there.

In contrast, trendy names might get a laugh or a knowing smile, but will very quickly feel outdated and off-trend. Stick to simple, classic names, and you’ll be happy long term as you watch your name evolve over time from being described as “easy to spell” and “straight-forward”, to “iconic”. If you still want to scratch the trend itch, just use marketing and socials to handle that mess.

The spelling problem.

If you’re doing things right, somebody will inevitably search for you on the internet. “Spykt NRGee” might have the .com domain available, but no one on God's green earth will find it.

Potential Lead: “What’s the best email address to use to reach you?”
You: "Email me at Rachel@, S (as in Sam) - P (as in pumpkin) - Y (as in yak)…”

Not only could a creative spelling bite you in the ass in most communications, but also, chaotically spelled names tend to be tougher to remember. We tend to associate words with visuals for memory, so removing any known visual representation from your name will make your company less memorable. Clearly, some successful companies have managed to pull this off (Google, obvs), but those tend to be the exception rather than the gold standard.

You may be forced to rename … eventually.

Off-the-cuff naming decisions rarely lasts.

Let’s say you made a not-so-great choice in your name and end up finding market success anyway. At some point your marketing team or sales team will inevitably bring up the idea of a “potential rebrand”. Let me let you in on a little secret: they finally had the guts to address the terrible name.

Rebranding sucks. It not only erodes any authority your name has in your market but also puts an extra level of burden on employees and customers to change the way they speak about your company. Not to mention all the internal costs, meetings, and corrections that will occur because you jumped on a trend in your haste to name your startup.

So, practically speaking, how do you find a timeless name?

Stick to the plan. Starting with authenticity, build into a deep understanding of the values of your market. When you start with empathy as a foundation, the outcome will be cool, no matter what trend is poppin’ at the time.

Now, let me be clear, this doesn’t mean you can't choose made-up names. Or that “loose” spelling concepts or words are off-limits. Companies like Microsoft, Figma, and Instagram are great examples of this: made-up words that feel like they’ve always been there and are easy to remember and simple to spell.

Even in the startup realm, I recently advised a new company named “Elora”. They’ve designed beautiful jewelry for women to wear to parties or bars, pieces that can test drinks for date-rape drugs with just a single drop. Gnarly problem to solve, but their branding is spot-on. Somehow, they managed to make up a name that feels like a jewelry company that has always been around. It’s easy to spell (exactly how it sounds) and feels soft and feminine. Great job, gals.

Let’s land the plane.

Naming your company doesn’t have to be a daunting task. It’s not a decision that should be scary to you. Remember when you began dreaming about what your new company could be? Remember how fun and exhilarating it was to actually write down your ideas, chew on them, cast away the dumb (or too crazy) ideas, and add new, better ones?

Naming your new brand should be an experience that's just as enjoyable. You might need to flex a slightly different muscle, but the more you flex it, the more of a creative beefcake you will turn into.

Just as it took work and time to find what your new venture could become, it will take work to find the right name for your company.

So let’s get to work.