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Q4 2023 Founder's Update

opening ceremony factory photo

This year, I’ve spent much of my time recruiting — a role I’m not naturally drawn to, perhaps due to the slow feedback loop. However, I continue to remind myself that bringing in more all-star talent is the most impactful thing I can do, and the team proves this daily.

Our business has grown quickly over the last four years. We had five employees in early 2020. We now have 18 full-time employees. We’ve hired seven this year, a record for us! I want to share some thoughts on when we hire.

After making a hire and seeing their impact on the business in the first six to twelve months, I’ve often questioned why we hadn’t hired for the position earlier. Hindsight is always 20/20. When business is good, it’s easy to feel that I'm not hiring fast enough and it's tempting to be more proactive based on anticipated growth. Despite the temptation, I'm committed to a more reactive hiring approach because it aligns with our values of steady long-term growth instead of a boom and bust roller coaster.

Benefits of proactive hiring based on anticipated growth:
• The right people will help get you where you want to go
• Seize opportunities faster
• Less burnout from overwork (maybe)

Benefits of reactive (delayed) hiring based on actual growth:
• Better understanding of where the business is going
• Better understanding of what the business needs
• Constraints often lead to creative problem solving
• Focus the team on process improvements instead of adding full-time team members
• Less chance of over-hiring and workforce reduction

Other values and beliefs that direct this policy:
• We respect our team member's commitment to our brand with a strong commitment to them.
• Entrepreneurs tend to overreact which hampers steady long term growth
• Working efficiently:
-- More people doesn’t necessarily lead to less work.
-- Efficiency per person decreases the larger an organization gets.
-- Before throwing more people at a problem, focus on efficiency improvements. If we don’t have an optimized process, why add more people? Let’s maximize output by optimizing the process instead of adding another team member to the unoptimized process.**
-- Always ask “What am I doing that doesn’t significantly impact the business and what could I be doing instead?”
• It’s easy to build a complex business. It’s harder to build a simple business. More people adds complexity.

With reactive hiring, we’re not hiring for the present at the expense of the future. We marry our present needs with anticipated future needs of the business. We’re looking for candidates that can grow with us. Do they have experience leading people? But can they still roll up their sleeves, get into the weeds, and enjoy doing it?

For Wool&Prince, the benefits of reactive hiring outweigh the benefits of proactive hiring. We’re a bootstrapped apparel brand emphasizing thoughtful growth, not growth at all costs. If you’re running a VC backed software company, that’s another story.

** Due to our growth over the last few years, we’re in an awkward teenage phase of the business where processes and systems break down and need to be refined. For some team members, I’ve suggested a target of having 20% capacity for projects outside their normal day-to-day work. We’re nowhere near that target, hence the need to bring on some additional team members in 2024.

Restocks planned for Jan/Feb:


• Short sleeve henley
• Boxer briefs
• Button down (Blue Tattersall, Blue Oxford, Blue Micro Check, 170 Navy Twill)
• Polos (updated colors in 100%, pique and self collar)

Other Updates:


Ten Years of Wool&Prince

It’s been a ride. Thank you to all the customers who have made this a success. Thank you to everyone who has helped build the company and support the journey.

I tend to put my head down and move from project to project without overindulging in the wins or getting too caught up in the losses. However, the 10th year has been full of emotion and gratitude for me. We now have around 30 team members including part-time contractors. Our main manufacturing partner who we've been working with for eight years has opened two factories for us and employs 75 people in Korea.

Since October, I've been hit with an unusual wave of emotions on three separate occasions — during our Korea factory visit, sample sale, and new office open house. What a joy it has been to appreciate everything that we’ve built and all the amazing people involved.

Trip to Asia

In October, we visited all of our partners in Asia and attended a factory opening ceremony (photo at the top of this post). Link to Instagram story here.


woven shirt factory

Sample Sale

We rented a vacant 10,000 sq ft space in Lloyd Center over a weekend in November. People flew in for the event and others told me "your boxers changed my life". Looking forward to our next in-person shopping event!

woven shirt factory

As always, please comment below if you have any thoughts or questions.

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