Weaving Strategy, Soul, and Sales in the Outdoor Industry with Darren Josey
Release Date: 04/10/2025
Your Micro-Actions Matter: Add Them to Your Everyday | 12 Weeks of Wintering Week 7
Creatives In The Wild
Welcome to Week 7 of ! We're exploring Values: the concepts that drive us forward and the principles we want to honor in our lives. Hear about my own value of autonomy and how it's shaped everything from my career choices to my daily life. But you'll also learn about something I've recently discovered: the power of honoring values in tiny, everyday moments. You'll learn: Why values serve as powerful compasses for decision making The difference between big overarching values and small, daily applications How tiny micro-actions can create a sense of fulfillment and alignment 12 Weeks of...
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What's Essential, Urgent, or Important as a Creative Business Owner? | 12 Weeks of Wintering Week 6
Creatives In The Wild
Welcome to Week 6 of ! We're exploring Essentialism: the practice of ruthless prioritization and figuring out what truly matters most. Hear about my own struggle with trying to pack too much into my calendar — both personally and in my business — and the toll it took on my energy and sense of aliveness. You'll learn: Why creatives and business owners are particularly vulnerable to non-essentialism The difference between what's essential, important, and urgent How saying no can take you further than saying yes 12 Weeks of Wintering is a practice I’m sharing while I’m on parental...
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Your Self-Identity Can Be a Tool AND a Trap | 12 Weeks of Wintering Week 5
Creatives In The Wild
Welcome to Week 5 of ! We're reflecting on Identity and the creation of our sense of self. It’s a paradox: A strong sense of identity can be incredibly powerful, but it can also become a trap. Hear my own story about how identifying as a "good snowboarder" kept me from taking risks, learning new things, and evolving in the sport I loved. You'll learn: Why we're sometimes afraid to change or evolve, because we're scared of leaving the old version of ourselves behind How rigid identities, especially ones given to us by others, can hold us back Why it's important to mourn old...
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Why It's Hard to Find Alignment as a Business Owner | 12 Weeks of Wintering Week 4
Creatives In The Wild
Welcome to Week 4 of ! This week, we're exploring Alignment: the place where your being meets your doing. Alignment is a word that gets tossed around a lot, but few of us know how to truly define it, even when we know we’re feeling out of alignment. You'll learn: Why alignment is especially challenging for business owners It’s a lifelong journey, not a one-time achievement How to give yourself grace as you continue refining what alignment means to you 12 Weeks of Wintering is a practice I’m sharing while I’m on parental leave. Each week offers a Wintering theme, with a minisode like...
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Embrace Seasonality in Outdoor Industry Work (and Life) | 12 Weeks of Wintering Week 3
Creatives In The Wild
Welcome to Week 3 of ! We're diving into the power of Seasonality: both the natural rhythms of the outdoor industry and the cyclical nature of growth itself. Hear about my past work as an events producer in the skiing and snowboarding industry, when seasonality dictated everything about my business. You'll learn: Why seasonality is a pattern, especially in the outdoor industry How to anticipate highs and lows to plan strategically (or give yourself permission to rest) The difference between linear growth and cyclical growth 12 Weeks of Wintering is a practice I’m sharing while I’m on...
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You Can't Out-Optimize Your Calendar: What's Your Capacity? | 12 Weeks of Wintering Week 2
Creatives In The Wild
Welcome to Week 2 of ! We're diving into the power of Capacity: understanding the time, energy, money, and space you actually have available to accomplish your goals (before taking action). Hear about my own reckoning with capacity when I became a mom, and the struggles I often see clients face around their capacity. You’ll learn: Why you can’t out-optimize your calendar A multi-step approach to managing your workload Why capacity and vision work best together 12 Weeks of Wintering is a practice I’m sharing while I’m on parental leave. Each week offers a Wintering theme, with a...
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Set a Clear Vision for 2026 and Beyond | 12 Weeks of Wintering Week 1
Creatives In The Wild
Welcome to Week 1 of ! We're diving into the power of Visioning: not just setting goals, but creating an expansive picture of the life and version of yourself you want to become. Hear my own story of building a "successful" freelance events business that checked all the boxes on paper, but didn't align with who I actually wanted to be. You’ll learn: Why it’s helpful to set goals that actually feed your vision Permission to be super expansive in your vision How freelancers can use visioning when times are tough 12 Weeks of Wintering is a practice I’m sharing while I’m on parental...
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Your Business, Your Way: How to Design Your Work Around Your Values
Creatives In The Wild
What does it mean to build a business that truly reflects who you are? Chereen Leong Schwarz of Smeeny Made Wild joins me to chat about how she integrates her core values into her maker business, including: How to integrate your values into every aspect of your business The role of intentionality in creative entrepreneurship Giving yourself permission to do things your way The importance of community and connection in staying inspired Why creativity and business don’t have to exist in isolation Creative business retreat meets all-women’s river trip in...
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Weaving Strategy, Soul, and Sales in the Outdoor Industry with Darren Josey
Creatives In The Wild
Darren Josey is an outdoorsman, bird watcher, spouse, father of two, and the founder of First Seed Sown. First Seed Sown is a sales and marketing agency serving fellow BIPOC-owned businesses, brands looking to improve their DEI initiatives, and municipalities with environmental justice communities who want to make the outdoors more equitable for everyone in their city. Connect with DJ or join his "Marketing on a $0 Budget" class: This is a longer episode than usual, but it's FULL of helpful perspectives for freelancers. Here are some timestamps so you can find parts to...
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Your Dreams are Allowed to Evolve as a Business Owner or Maker
Creatives In The Wild
What if the goal you set ends up being something you don't want, after all? Chereen Leong Schwarz of Smeeny Made Wild joins me to share her winding path of entrepreneurship, including: How dreams evolve and why alignment is a process, not a destination The challenge of letting go of past versions of yourself Making big career shifts and embracing uncertainty Recognizing when it’s time to realign your business with your values The power of community and support in creative entrepreneurship Retreat update: We're pushing the British Columbia Retreat to 2026! Curious...
info_outlineDarren Josey is an outdoorsman, bird watcher, spouse, father of two, and the founder of First Seed Sown.
First Seed Sown is a sales and marketing agency serving fellow BIPOC-owned businesses, brands looking to improve their DEI initiatives, and municipalities with environmental justice communities who want to make the outdoors more equitable for everyone in their city.
Connect with DJ or join his "Marketing on a $0 Budget" class: https://www.firstseedsown.com/workshops
This is a longer episode than usual, but it's FULL of helpful perspectives for freelancers. Here are some timestamps so you can find parts to listen back to a second time!:
(03:00) - What First Seed Sown is and why DJ founded this company
(04:31) - How finding your purpose and mission takes time
(05:30) - Getting his start at Vibram and the opportunities DJ created for himself
(06:30) - How Vibram maximized the start of social media, a hole in the marketplace, and a book launch to dominate the market
(07:30) - The issues leading to Vibram's downturn
(09:00) - How to apply Vibram's growth to the current market
(09:30) - Why starting your product-based brand as narrow as possible is key to success
(10:25) - The importance of listening to your market and pivoting when your users ask you to change
(13:24) - How working in retail shaped DJ's entire career and how it applies to you and the industry
(15:25) - How products move from a brand to a sales rep to the retail store and why it matters
(16:15) - The sales knowledge you can only learn from retail
(16:30) - What you need to know about wholesale vs direct to consumer business if you're a small brand
(18:23) - Why understanding the retail ecosystem is essential for creatives and service providers
(20:55) - How the product, sales, and marketing teams influence each other
(24:40) - The relationship between price and value of a product
(25:58) - What the sales team determines at a brand
(26:16) - When the product, sales, and marketing departments are at their best
(27:00) - The role of the CEO in leading a brand
(28:50) - The in-house complexities all freelancers should know about when waiting for your next contract
(31:17) - The person you're working with at a brand is overworked and under-resourced
(33:10) - Why AI isn't going to solve our overwork issues
(33:55) - Why working for himself has been key to DJ meeting his own potential
(36:32) - What two strategies you need to implement to successfully pitch your next client in the outdoor industry
(40:19) - The factor most freelancers forget to think about when it comes to pitching to brands
(42:24) - Your future clients want to hear from you and not just to be sold your services
(44:40) - Who will actually read your pitches at a brand and who won't
(45:16) - Why meeting people in person is still essential to building relationships with potential clients
(47:57) - The outdoors industry is still a handshakes and shoe leather business
(50:00) - Building in-person relationships is a muscle we all need to strengthen post-pandemic
(51:15) - The privilege of leveraging big contracts as an opportunity to create and sell additional work
(52:20) - The responsibility we have to our fellow creatives by creating more transparency and not undervaluing our work
(55:45) - Why DJ structures his pricing the way he does and how it ties into his mission
(56:20) - The importance of having different rates for different kinds of work and different results
(58:08) - DJ's move from Vibram to Topo Athletic and what he learned from handshakes and beer trades
(59:08) - Why "building a hometown brand" is your next marketing strategy
(1:01:17) - DJ's role at Polartec and the impact of mixing with the biggest brands in the outdoors industry
(1:02:13) - Your favorite brands use the same fabric but position it differently and you can too
(1:03:52) - The power of creating environmental justice communities and the impact of shifting from brand to cities partners
(1:06:46) - The powerful vision behind First Seed Sown and the impact of a wholistic approach in Malden, Massachusetts
(1:08:26) - What a wholistic approach can create for environmental justice communities
(1:09:27) - Sharing outdoor industry jobs with the next generation of leaders
(1:11:02) - DJ's commitment to supporting BIPOC-owned companies as the root of founding First Seed Sown
(1:12:10) - Why supporting diverse communities is essential to growing the outdoors industry
(1:13:40) - How DJ's approach of paying it forward is a foundational tool to cultivating business relationships
(1:15:52) - DJ's work as a core advisor of REI's Path Ahead Ventures and how programs like this create equity in business
(1:17:04) - Why having brands made by diverse founders is a smart business move and how to navigate the attacks on DEI programs
(1:18:26) - How DJ supporting up and coming BIPOC brands with the wholistic ecosystem
(1:19:07) - Why timing matters as a business owner, especially when you're thinking about bringing on support
(1:19:48) - Future things to be on the lookout for to benefit from DJ's extensive expertise
(1:21:24) - How to strengthen the industry by introducing brands to DJ's work, hiring more diverse voices on your projects, and supporting outdoor ethnic affinity groups
(1:23:29) - How DJ stays optimistic and focused by doing mission-aligned work that supports businesses increase their profit and prioritize people
Connect with Justine: https://www.justawildthought.com
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