On today's episode, I sit down with Lil Tuffy, a San Francisco-based poster artist who’s spent more than two decades designing and hand-printing concert posters.

Tuffy's path into poster design started almost accidentally. After leaving the tech world and getting involved in the San Francisco music scene, he began making posters for shows around the city. What started as creating unsolicited posters for small venues gradually evolved into a full-time practice, eventually leading to work with legendary artists like Neil Young, Willie Nelson, and many others.

In this conversation, we talk about how the economics of concert posters actually work — from setting print runs to how revenue from poster sales is split between artists, bands, and venues. We also get into the logistics of screen printing, the timeline from design to finished poster, and how the role of concert posters has evolved from promotional material to collectible merchandise.

We also talk about his work with the Poster Institute, a nonprofit organization that supports poster artists around the world through events, exhibitions, and community building within the gig poster scene.

I've been collecting concert posters for over 15 years, and Tuffy is genuinely one of my favorite artists. I learned so much during our conversation and I hope you enjoy it as much as I did.

On today’s episode, I sit down with Sherri Franklin, founder of Muttville, a senior dog rescue based in San Francisco that has helped find homes for more than 14,000 older dogs.

Sherri didn’t start her career in animal welfare. She was a hairstylist who had previously owned several salons in San Francisco when she began volunteering at a local shelter in the 90s. After watching a dog she loved get euthanized simply because she was older and overlooked by adopters, Sherri decided she was going to build something that didn’t really exist at the time: a rescue focused entirely on senior dogs.

What started with Sherri fostering dogs in her own home and placing them with her hair clients eventually grew into a nonprofit with a full foster network, a dedicated adoption center, and a model that now rescues more than a thousand dogs every year.

In this conversation, we talk about what those earliest days actually looked like operationally, from paying vet bills out of pocket to learning how to structure a nonprofit and recruit a board.

We also get into the mechanics of running a large scale rescue today, including how foster networks function as the engine of the organization, how they think about adoption versus sanctuary care, and what it takes to consistently place senior dogs that most shelters have historically struggled to move.

This was a deeply personal conversation for me, as Muttville is truly my favorite nonprofit in the world. The rate at which they’re placing dogs is absolutely amazing, and I’m just so honored to be able to share the work they’re doing, and help get the word out in any way that I can.

I learned so much from Sherri during our conversation and I hope you enjoy this one as much as I did.

On today’s episode, I sit down with Kelly Bennett, brand strategist and host of the Emerging Brands Podcast.

Kelly has spent the last 16 years working alongside founders in the food and beverage space, helping them turn early product ideas into shelf-ready brands. Her focus is pre-launch brand strategy, which means she’s often involved before a founder has finalized a name, filed a trademark, or chosen a manufacturer. Her job is to build the underlying framework that everything else sits on top of.

In this conversation, we talk about what brand strategy actually is beyond logos and packaging, how to think about retail positioning and sales channels before you ever approach a buyer, and why clarity around target customer and use case should really come before design. We also get into pre-launch demand creation, building in public without looking too DIY, and the specific signals she watches once a product hits the market to evaluate the efficacy of the strategies she’s helping implement.

We also explore the value the media arm of her business is driving, how her podcast functions as both a network engine and a client acquisition funnel, and how she’s thinking about evolving from just advising to investing in emerging CPG brands as well.

I learned so much during my conversation with Kelly and I hope you enjoy it as much as I did.

On today’s episode, I sit down with Brian McMahon, co-founder and CEO of Pickle, a peer-to-peer rental marketplace built around the idea that the things sitting in our closets can function as income-generating assets.

Brian started his career in finance before teaching himself how to code and launching what was originally a social polling app designed to help people make purchase decisions. But after noticing that users were constantly recommending items they already owned, he and his co-founder (Julia) pivoted toward a marketplace model focused on renting, lending, and reselling personal items.

In this conversation, we talk about what that pivot looked like in practice, the scrappy early days of photographing inventory in friends’ apartments, personally completing thousands of deliveries across New York, and how an asset-light model shapes everything from supply dynamics to operational complexity.

We also break down how Pickle generated its first network effects, lessons from fundraising, and how Pickle is thinking about expanding into new categories as it works toward unlocking underutilized consumer assets at scale.

I learned so much from Brian and I hope you enjoy the conversation as much as I did.

On today’s episode, I sit down with Adam Gillman, Co-Founder of Hiya, a direct-to-consumer children’s vitamin and wellness company built around trust, transparency, and customer education as core operating principles.

We talk through how Hiya approached product development without prior experience in the health and wellness space, including how they thought about formulation tradeoffs, manufacturing partners, and palatability versus nutrition. Adam walks through why the company committed to a 100% subscription model from day one, how retention and customer feedback shaped product iteration over time, and how pricing was set to signal quality while remaining broadly accessible.

We also get into the operational realities of scaling a subscription business: managing cash flow while offering upfront discounts, navigating rising costs during COVID, financing growth while bootstrapped, and deciding when it made sense to expand the product line. Finally, Adam shares how scaling constraints and operational gaps ultimately led Hiya to pursue an acquisition, and what they looked for in a partner.

I can’t believe how much I learned in just 35 minutes with Adam, and as always, I hope you enjoy the conversation as much as I did.

On today’s episode, I sit down with Kiki Couchman and Elan Halpern, the co-founders of Sourmilk.

Sourmilk is built around a simple but differentiated premise: take something 92% of households already consume and engineer it to deliver measurable gut-health impact. We talk through how they formulated around specific probiotic strains rather than optimizing purely for flavor, what it looked like to source grass-fed dairy without prior industry experience, and how they built a co-manufacturing relationship from scratch.

We also get into their deliberately high-friction, self-distributed drop model as a way to validate demand, measure retention, and collect first-party customer data before entering retail. From there, we discuss cold-chain constraints, retailer relationships, geographic saturation before national expansion, fundraising discipline, and what it takes to build defensibility in a category dominated by large incumbents.

I learned so much from Kiki and Elan, and I hope you enjoy the conversation as much as I did.

On today's episode, I sit down with Joe Hollier, co-founder of Light, the company behind the Light Phone — a minimalist mobile device designed to be used as little as possible.

We talk about how the company emerged from an experimental Google design program, why Joe and his co-founder chose to build hardware in a software-dominated world, and what it actually takes to bring a new phone to market without relying on the traditional venture-backed smartphone playbook. We get into crowdfunding as early validation, how they managed to develop a relationship with Foxconn — one of the world’s largest manufacturers of electronics — and what that partnership required at their scale.

We also break down the unit economics: non-recurring engineering costs, bill of materials, software licensing fees for tools like directions, inventory financing, and how tariffs and component shortages have affected margins. We discuss the tradeoffs behind feature decisions — why the phone includes essentials like calling, texting, directions, and now a camera, but will never include features like social media access, email, or an internet browser — and how those boundaries shape both the product and the business model.

This was a thoughtful, detailed look at what it takes to build a hardware company with a fundamentally different incentive structure. I learned so much from Joe, and I hope you enjoy the conversation as much as I did.

In today's episode, I sit down with Sara Victorio, founder of Hotel Ceramics, a one-person handmade ceramics studio based in Portland, Oregon.

We talk about how Hotel operates as a solo manufacturing business, from product design and material inputs to kiln capacity, production methods, and quality control. Sara walks through why she shifted from wheel throwing to slip casting, how that decision changed her labor economics and output constraints, and what tradeoffs it introduced operationally.

We also get into pricing and margin considerations in handmade ceramics, including how labor, throughput, and failure rates factor into pricing decisions, and why Hotel uses a drop-based sales model rather than pre-orders. Throughout the conversation, we discuss demand management, customer expectations, repeat purchase behavior, and how distribution choices affect both cash flow and workload when the founder is also the sole producer.

This was a clear, grounded look at the mechanics of running a small, design-driven physical goods business with real production constraints. I learned so much during my conversation with Sara, and I hope you enjoy it as much as I did.

In today's episode, I sit down with Nate Mell, founder of Felt + Fat, a Philadelphia-based ceramics company producing tableware for both restaurants and direct-to-consumer customers.

We talk about how Felt + Fat began supplying custom tableware to restaurants, why ceramics made sense as a business from a unit-economics perspective, and how debt-financed equipment shaped the company’s growth and risk profile. Nate walks through the operational realities of scaling a labor-intensive manufacturing business, the shift from wholesale to direct-to-consumer, and how capital decisions around space, equipment, and staffing affected margins and cash flow. We also get into the limits of vertical integration, what rapid expansion exposed about the business model, and how a period of financial distress forced a clear-eyed reassessment of what the company actually does best — ultimately leading to a narrower, more sustainable operating scope.

This was a candid, detailed look at the mechanics of running a U.S.-based manufacturing business and I can't thank Nate enough for his transparency around some pretty sensitive topics. I learned so much during our conversation, and I hope you enjoy it as much as I did.

In today's episode, I sit down with Jared Klusner, founder of Erstwhile, a jewelry business built around highly curated vintage and vintage-inspired pieces.

We talk about Jared’s path into the jewelry world, how sourcing actually works in a niche, relationship-driven market, and why trust and expertise matter so much when you’re dealing in rare, one-of-a-kind goods.

We also get into the mechanics of building a business around non-fungible inventory — from pricing and negotiation to replacement risk, inventory management, and the realities of scaling a high-touch operation without losing credibility.

This was a fascinating look at what it really takes to build a relationship-driven business in high-end vintage goods. I learned so much from the conversation, and I hope you enjoy it as much as I did.