Flying the Coop

#17 Jessica Lackey: You can't move faster than the speed of your own growth

"If they teach you how to build a business, you stop buying their stuff. That's not what they want." — Jessica Lackey A lot of business advice is a slot machine dressed up as a strategy. Jessica Lackey's book Leaving the Casino lays it out cold: the entrepreneurial industrial complex isn't, in fact, designed to help you build a sustainable business. It's designed to keep you spending money on the PROMISE of one. She and Anna get into: * Why and how the casino targets the most vulnerable entrepreneurs, MLM-style * The zone of enoughness: how to define your minimum and maximum across money, time, schedule flexibility, and creative autonomy * Why "just raise your prices" might be the most misplaced advice in the industry, and what to actually do instead * The difference between slowing down your activity and slowing down your expectations * Why if your marketing isn't working, it's probably your market, not your mindset --  Flying the Coop is brought to you by Strange Birds, a worker-owned co-op. When the opportunity is clear and the doing feels impossible, we get inside your hardest project, find what needs to happen, and follow it all the way through. Find us at ⁠http://strangebirds.land

#16 Nilou Khonsari: Collectivism isn't radical, we just forgot how to do it

"Collective care feels like an exhale — like finally being able to breathe at work." – Nilou Khonsari Most organizations that say they value collective care don't actually build for it. They write values statements, flatten a few org chart lines, and hope the culture follows. (spoiler: it doesn't.) Nilou Khonsari spent ten years co-building Pangaea Legal Services, a nationally recognized immigrant justice nonprofit, into a model of what collective governance actually looks like in practice. Through her book The Future Is Collective, she helps organizations build structures that truly reflect their values. Anna and I did a full winter book club around this one. (We ate it up. I read every word of the appendices.) This conversation gets into hardcore collective scaffolding: * The difference between advice process, modified consensus, and consent-based decision making * What Nilou learned from almost paying her co-founder $1,000 less than herself * How equal pay worked beautifully at Pangaea for years, until it didn't * How to redesign a nonprofit board so the people closest to the work are the ones driving it * Boundaries as a collective practice, not a personal one And woven throughout: Strange Birds' own messy, ongoing, in-progress attempt to enact a lot of this fun stuff ourselves. --  Flying the Coop is brought to you by Strange Birds, a worker-owned co-op. When the opportunity is clear and the doing feels impossible, we get inside your hardest project, find what needs to happen, and follow it all the way through. Find us at ⁠http://strangebirds.land [%E2%81%A0http%3A/strangebirds.land]

# 15 Meg Rye is redesigning recruitment from the inside

"If you want to take the time to really understand every human being you're working with — that takes more time. And time is money. And that's inherently anti-capitalistic." — Meg Rye Hiring is a power system. Most people on both sides of it (candidates and companies alike) have just accepted that as a fact of life. Meg Rye hasn't. Meg is the founder of Good Maven, a design recruitment and career coaching business built on a pretty radical premise: that recruiters can function as guardians rather than brokers. That the job isn't to scoot humans through a pipeline as efficiently as possible; it's to understand what each person actually needs, and make connections that honor that. In this conversation, we get into the mechanics of what that looks like in practice: how Good Maven approaches underrepresented talent, why diverse pipelines don't happen by accident, and what it actually takes to redesign hiring around care rather than conversion. We also go deep on the structural side — B Corp certification, Employee Ownership Trusts, EMI shares — because Meg is building the values into the bones of the business itself, not just the pitch deck. (Janel will be the first to admit this part of the conversation made her head spin a little. Anna loved every second of it.) We explore: * Why "there just aren't enough qualified candidates" is a load of hooey... and what actually widens the funnel * What consent-based recruiting looks like in practice, from the first conversation to the final offer * How to balance meaning and mortgage in a job market that's genuinely tough right now * The structural scaffolding Meg is building at Good Maven: B Corp, EOTs, and why she's thinking about exit strategy before she's anywhere near exit * Why the next generation of recruiters needs real mentorship, not just AI shortcuts --  Flying the Coop is brought to you by Strange Birds, a worker-owned co-op. When the opportunity is clear and the doing feels impossible, we get inside your hardest project, find what needs to happen, and follow it all the way through. Find us at ⁠http://strangebirds.land [%E2%81%A0http%3A/strangebirds.land]

# 14 Tarzan Kay has the antidote to hustle culture (and it’s not simply "slowing down")

“We’ve been sold such a narrow idea of what a business can be — like you either coach or sell a course. But there are so many ways to build something rich and beautiful, something that’s actually yours. A business can give you so much more than just money — it can give you community, relationships, growth, and experiences.” - Tarzan Kay What would work look like if designed it around real humans, real relationships, and real choice? In this episode of Flying the Coop, we’re joined by Tarzan Kay, a leader in consent-based business design and marketing. Tarzan shares how her thinking has evolved from traditional online marketing into a much deeper exploration of power, persuasion, autonomy, and responsibility. This episode was extra special to me as I've been following Tarzan for the last decade, watching her evolve from self-dubbed "email marketing diva" into something much more expansive and inspiring (who still tells a mean story or three 'round the fire). What a total honor to have her on the show to explore: * How classic business models limit creativity and possibility * Why urgency and persuasion shut down critical thinking * What consent looks like on a practical level in marketing, leadership, and community spaces * Why businesses hold real power, and how to wield it responsibly This convo smashes to smithereens the prefab version of success we’ve all been handed, replacing it with hope: expansive, relational, creative, and alive. --  Flying the Coop is brought to you by Strange Birds, a messaging co-op that gives a flying duck. From websites to onboarding flows, launches to long-term strategy: if you want your brand, offers, and experience to tell the same story, we can help. Find us at ⁠http://strangebirds.land [%E2%81%A0http%3A/strangebirds.land]

#13 Sara Otto: Supply chains that center the people within them

“Supply chains are made of people, not just products or paperwork.” – Sara Otto Supply chains touch almost everything we buy — clothes, home goods, gifts, art — yet most of us never really see how they work, or who they rely on. In this episode of Flying the Coop, we’re joined by Sara Otto, Chief Supply Chain Officer at Nest, a nonprofit working globally to make artisan supply chains more equitable, transparent, and sustainable, especially for home-based and small-workshop makers who are often invisible to traditional oversight. Sara shares how Nest operates at the intersection of ethics, compliance, logistics, and real-world commerce, translating “we want to do business better” into systems that actually protect workers’ rights and dignity. Drawing on years of experience living and working alongside artisan communities, she offers a look at what real-deal ethical sourcing looks like. Together, we explore: * How "social compliance" rests on relationships * How Nest bridges the gap between global brands and small-scale artisans * How transparency begins with simply knowing who is in a supply chain * What equity looks like beyond paternalism or "white savior" models This conversation is a grounded, compassionate look at how complex global systems can be redesigned to respect humanity at every level. --  Flying the Coop is brought to you by Strange Birds, a messaging co-op that gives a flying duck. From websites to onboarding flows, launches to long-term strategy: if you want your brand, offers, and experience to tell the same story, we can help. Find us at ⁠http://strangebirds.land [%E2%81%A0http%3A/strangebirds.land]