Weaving Strategy, Soul, and Sales in the Outdoor Industry with Darren Josey
Release Date: 04/10/2025
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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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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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...
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Fear is inevitable, but you can work with it in your business, not against it. Chereen Leong Schwarz of Smeeny Made Wild joins me to talk about fear and discomfort as a business owner, including: Differentiating between fear and discomfort How outdoor adventures can help us build resilience in business Reframing fear as a muscle that can be strengthened Making bold choices in your creative career How to approach change and uncertainty with confidence Retreat update: We're pushing the British Columbia Retreat to 2026! Curious about future retreats? Get on the interest...
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You're invited— I'm teaming up with Chereen to build an incredible this August 2025 in Squamish, BC! Chereen Leong Schwarz (she/her) is the founder and chief-everything-officer behind Smeeny Made Wild. Chereen taught herself to knit with a pair of thrifted knitting needles and YouTube videos, and what started as a hobby quickly became a passion. Today, Smeeny Made Wild is more than a brand; it’s a community of adventurous creatives, artists, and small business owners who are rewilding life and business by slowing down and reconnecting with nature, creativity, and what truly...
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Are you experiencing a slow season in your freelance work? It can be scary, but remember, whether you're new or established in business, it's normal to face highs and lows in demand for work. Business is cyclical— especially in the outdoor industry. And you CAN create new business opportunities for yourself— that's a skill we can all learn. Let's talk about the best uses of your time during slow seasons of work, including: Rest intentionally. Get outside. Deepen your creative skillset. Work ON (not in) your business. Audit your business. ...
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Creatives often feel tension between honoring what a brand wants and respecting the authentic story of a person or community. How can you do both? Sabrina Claros is a photographer, videographer, and creative director based in LA, creating stories at the intersection of adventure, environmentalism, and outdoor equity. Her work aims to create change and inspire more people to connect with the outdoors and feel called to protect our natural resources, while reducing barriers to who has access in outdoor spaces. Sabrina has worked with brands such as Teva, Tough Cutie, Bedrock...
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2025 did not start out the way I wanted it to. Many of my clients are also getting that "What's the point?" feeling with the state of the world. Here's the twist: Actually answering the question of "What's the point?" thoughtfully is giving me hope. We can control how we're showing up for our community. We have agency around the impact that we're able to make. We can invest in our values to shape a brighter future. Here are four small but mighty actions I'm taking this month: Getting more intentional about social media usage Narrowing my focus to certain causes...
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What can freelancers learn from those founding product-based businesses? Katie Doherty is the co-founder of Founded Outdoors, a company dedicated to providing resources, programming, and community for emerging outdoor brands. She is passionate about driving inclusive change through entrepreneurship and combines her experience in the tech start-up world and her love of the outdoors by supporting founders from idea to launch. With her co-founder Enhao Li, she has created a thriving community of outdoor industry founders and has supported more than 65 founders through their...
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Sometime around years 2 or 3 of freelancing, you can find yourself facing new challenges, often resulting from all the things you did well when you first launched your business. You hustled, you said YES to everything and everyone, and you made sh*t happen. But now, you probably have plenty of work and clients, but you're not doing the work or living the life you expected to. Learn the first steps I recommend for getting unstuck when you: Find yourself working too much Keep saying yes to the wrong clients Don't feel safe in your business Run into friction in your systems Have trouble honoring...
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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