Connor Wilson on Building a Lasting Brand

Connor Wilson, co-founder of Thursday Boot Company

Founder to Founder: Connor Wilson, Co-Founder of Thursday Boot Company

Fast Iterations and Long Time Horizons: Building a Brand That Lasts

The 2010s produced a wave of direct-to-consumer brands that grew fast, raised big, and, in many cases, flamed out just as quickly. Thursday Boot Company took another approach. Connor Wilson co-founded Thursday in 2014 with Nolan Walsh, whom he met on their first day at Columbia Business School, out of a simple frustration: they couldn’t find a boot that was well-made, versatile, and honestly priced.

They launched on Kickstarter, treated their customers like royalty, and bet that the product itself would be their best marketing. Over the last decade, they’ve reinvested in that product relentlessly while growing the company deliberately and on their own terms.

Thursday Boot Company handcrafted leather boots for women

More than a decade later, Thursday has expanded well beyond boots into sneakers, jackets, and more, all while holding onto the principles that got it off the ground: product as the foundation, tight control of costs and first-party data, and a refusal to chase growth just for the sake of it.

In Dwight's latest Founder to Founder, Connor talks about fast iterations, long time horizons, and what it takes to build a brand that lasts.
Thursday Boot Company footwear

Thursday is a decade in and still founder-led. When you look back at the early days, what were you optimizing for that you think set the company up for where it is now?

The biggest thing we got right early on was treating product as the foundation of the company. If the product is great, people buy more, come back, and tell their friends. We almost thought of it as a marketing expense, something you invest in until it becomes a word-of-mouth phenomenon. That’s only mattered more as we’ve moved into new categories. If you’re always delivering great product, you have a business to build on. If you’re not, you won’t make it far.

The other was staying nimble. From day one we were deliberate about controlling our costs and our data. A big part of that was choosing not to do wholesale in any meaningful way. That gave us a level of first-party data most brands never get, and that insight goes straight back into the product. It also keeps us sharp on inventory. We’re never understocked or overstocked, so we never have to run sales to clear product. That means we can offer great pricing year-round no matter what.

These are little decisions, built on a lot of quick, tiny iterations, but they serve the longer-term purpose: great product, real value for the customer, and a solid foundation for the business.

There used to be a lot of pressure in this category to grow as fast as you possibly can. Did you take that approach at Thursday?

We have a strong belief that there’s no such thing as a shortcut. As a former track and cross-country runner, I’m good at enduring pain and putting one foot in front of the other, and my co-founder Nolan is even more so. We live by the principle that this isn’t a sprint. It’s always a marathon, just run at a really fast pace. 

When another brand raises a ton of capital at a high valuation and posts eye-popping numbers, it’s natural to feel a little envious. The math never worked for us, though. Instead of trying to join them or beat them, we ran our own race and continued to double down on what was already working. 

In hindsight, a lot of those fast-growth stories were built on foundations of sand. We’ve watched big-name brands climb high and then crater. In the end, everyone suffers from it. 

How do you think about the right pace of growth?

Our view is that if we get a little better every year and keep at it long enough, it compounds into a really great business. So far that’s proven true.

The key is growing at the rate the brand can naturally support. Juicing growth works in the short term, but it comes with a nasty hangover. The founders who do best let their brand grow organically through great product, service, and brand rather than trying to force it. 

Similar to your stance on growth, Thursday has taken a deliberate approach to capital. How do you think about the role outside investment should play in building a brand?

For a lot of founders, raising capital becomes the goal itself. It shouldn’t be. Capital is a means to an end, and the end is building a brand and product people love, sustainably and profitably.

That’s why you have to be very selective about who you bring in. There are certainly investors who will genuinely share your vision, and Thursday is an example of that. Most, though, will care mainly about returns, even if they claim otherwise. As a founder, you have to be so obsessed with your product, your customers, and your brand that you’d never hand a piece of it to someone who doesn’t share that conviction. We’ve been so selective about choosing the right teammates – colleagues and investors who understand not only our goals, but also why they matter.

In the end, there’s no such thing as free money. Any time you take money from someone, it’s an obligation. Treat every dollar like it’s your last, and spend it as if it’s your own, because it is. Treat it like free money, and lo and behold, it spends pretty fast.

What would you say to a founder in the early stages who’s feeling the pressure to grow fast and raise big?

There’s actually some real value in that pressure early on. You have to reach a certain size and scale to have a real business, and if you’re not growing quickly enough at the start, it’s usually a sign that something’s off in your product, your marketing, or your operations. 

Then, once you’re profitable and you really know your business and your customer, remind yourself that the best brands were built over decades. It’s not flashy, it’s not fast, it’s actually very slow. Be speedy up front just to make sure you’re in the race, then hold a pace you can actually control. 

That discipline matters especially for consumer brands, where inventory is a prerequisite for revenue. The faster you grow, the more capital you need. At high enough growth rates, the capital wall becomes genuinely scary. Sometimes it’s better to let some demand go unfulfilled than to chase it at any cost and give away permanent equity or take on debt you can’t handle.

Key Takeaways…

  • Grow fast enough to get in the race, but steady enough to win it. Move fast enough early on to prove product-market fit and get in the race. After that, remind yourself that the best brands are built over decades. Get a little better every year and let it compound. Juicing growth always comes with a nasty hangover.

  • Own the channel and you can price honestly. By resisting wholesale, Thursday kept its cost, inventory, and first-party customer data under its own control. That discipline means no fire-sales to clear stock. Just honest, year-round pricing customers can trust.
  • Your product is your marketing budget. The product is the foundation of the whole company. When it’s genuinely great, it drives repeat purchases and free word-of-mouth marketing. Investing in product turns into organic growth you don’t have to keep paying for.

  • There’s no such thing as free money. Capital is a means to an end, not a milestone. The temptation to match a competitor’s big raise is real, but every dollar is another obligation and no outside partner will be as obsessed with your vision as you are.

About Thursday Boot Company

Thursday was built out of our own frustration. Clunky work boots or delicate fashion boots? Cheap shoes that fall apart after a few wears, or wildly overpriced ones? There had to be a better option than these trade-offs, so we started Thursday to offer an alternative: ridiculously high quality footwear at honest prices that could handle our busy lives in New York City. Since then, we’ve expanded into dress shoes, sneakers, jackets, and more, but our commitment to offering great products at honest prices remains the same.

Thursday Boots Company Boots and Jeans
Thursday Boot Company logo
  • 100,000+ 5-star customer reviews
  • Served customers in all 50 states and over 150 countries since 2014

About Connor Wilson

Prior to founding the company, he spent six years with Thornburg Investment Management as an equity analyst and associate portfolio manager. He earned his MBA from Columbia Business School, and graduated from Harvard undergrad with an A.B. in Government, where he also ran varsity track and cross country. Connor is a CFA charterholder and avid history reader.

Connor Wilson, co-founder of Thursday Boots Company

About Dwight Funding’s Founder to Founder series

More Stories to read

See why brands like yours choose to partner with Dwight.

Stay in the Loop

Sign up for our newsletter for the most relevant insights in your industry.

The Latest Trends, Insights, and Fundraising News in Your Industry

By providing your email, you are consenting to receive communications from Dwight Funding. Visit our Privacy Policy for more info, or contact us at privacy@dwightfunding.com or 787 11th Avenue, 10th Floor, New York, NY 10019