Engineering Adult Friendships to a Billion Dollar Business

Engineering Adult Friendships to a Billion Dollar Business

What happens when a former consumer brand founder gets tired of the working capital grind, spots a broken format in adult recreational sports leagues, and decides to engineer the conditions for adults to actually make new friends? Tommy Flaim, Founder of Silly Pickles, joins In The Money to break down one of the more unexpected growth stories in the consumer space, a pickleball league that started as a side hustle managed on Microsoft Excel, hit a waitlist of over a thousand players in its first few seasons, and is now in 75 metro areas across the US, Canada, and Australia doing $6 million in run rate on just $750K raised. We cover: * Why adult recreational sports leagues have a broken format and the dynamic ladder system Tommy built to fix it * How to engineer a social outcome: skill-based matchups, repeat exposure, happy hours, and the magic of a great local host * Why 50% of Silly Pickles players have never played in another adult rec league and 30% had never even played pickleball before their first night * The bottom 90% thesis: why most competitors target washed-up athletes and why Tommy is going after everyone else * How Silly Pickles went from one Chicago bar to 75 metro areas with a decentralized hub-and-spoke model * Brand partnerships: Waterboy, an alcohol brand, an iced tea brand and why Silly Pickles is becoming one of the most interesting IRL activation platforms in consumer * What CPG brands get wrong about IRL activations and the two ingredients that make the difference between a great event and a forgettable one * The non-technical founder's guide to building software: the agency route, the tradeoffs, and why Tommy chose the most expensive option on purpose * The math to a billion: 200 metro areas, 10 sports, $500K per metro area per sport * Pickleball as the wedge and what comes next as they layer on volleyball and additional sports * Lessons from his consumer apparel brand: what he'd do differently and why he's now a little jaded about inventory-based businesses * The holy trinity for consumer founders: brand, community, differentiated product, and catching a wave before incumbents catch up * Why TikTok is still the most important platform for consumer businesses and what to do if you're not good at it yet If you're building a consumer brand, thinking about IRL community as a channel, or trying to understand what catching a category wave actually looks like from the inside this episode is packed with hard-won lessons from a founder who's done it twice.

We Thought It Could Be a Modest $10M Business. We Were Very Wrong.

What does it look like to send 25 to 30 cold emails to a founder you've never met because you believe in a product so much you're willing to bet your career on it? Kieran Mathew, CEO of Equip Foods, joins In The Money to break down one of the more unconventional origin stories in better-for-you supplements, an operator who joined an existing business, took over day-to-day functions from the founder, and helped scale it from low seven figures to well into eight on a growth model that barely touched Meta spend. Equip makes animal-based protein products built around one standard: real food ingredients, nothing the brand wouldn't stand behind completely. No fillers. No shortcuts. A product built for a customer who reads labels and doesn't forgive compromises. We cover: * Why Kieran sent 25-30 emails to founder Anthony Gustin before getting a response and what he said to finally get one * What it actually looks like to join a business as an operator-partner rather than a founder * How to take over day-to-day operations from a founder without breaking what's already working * The affiliate flywheel: how Equip built a roster of thousands of partners who became genuine evangelists for the brand * How affiliate seeding trained the algorithm before a dollar of Meta spend and what that did to ROAS when they finally turned it on * Why beef protein is having its moment and how whey margin compression is accelerating the category shift * The animal-based consumer: who they are, what they believe, and why they're more loyal than almost any other supplement customer * What Equip would do differently in paid if they were starting the channel from scratch today * Org structure evolution: why the team design that worked at $3M doesn't work at $15M and what needs to change * How Equip thinks about SKU expansion without losing the brand clarity that made them * Retention, subscription, and what actually drives LTV in the supplement category If you're building in supplements, better-for-you CPG, or thinking about how to join an existing business as an operator rather than start from scratch, this episode is one of the most useful conversations I've had on the pod this year.

The LinkedIn Message They Almost Ignored For Target Nationwide

What happens when a high-protein, clean-ingredient frozen pizza brand spends two years grinding through cold chain nightmares, supply chain restarts, and a fundraising carousel, and then lands at number one in the frozen pizza category at Target? Michael Rolland, Co-Founder of Yough!, joins In The Money to tell one of the more honest origin stories in better-for-you frozen food, a brand built around a simple thesis that you shouldn't have to choose between eating pizza and feeling good afterward, and the long road it took to get that product in front of the right retailers at the right moment. 700 calories. 46 grams of protein. No junk ingredients. An anytime meal that people are eating pre-workout, post-workout, and at 2am after a night out, without the guilt. We cover: * Why DTC was the wrong model for frozen and what Yough! learned the expensive way * The supply chain issues that forced a full relaunch and why it ultimately made the product better * How Yough! built into boutique specialty retail first before going mass * The LinkedIn message they almost ignored and how it turned into a meeting at Target HQ * What it actually looks like when a national retailer offers you a launch before you've pitched them * Going from specialty to Target and Sprouts on organic momentum alone, no broker, no traditional pitch * What number one in frozen pizza at Target actually means for a brand at this stage * The fundraising reality for better-for-you frozen: what investors want to see and when the timing is right * Protein in frozen as the next major category wave and why the timing is right now * What Michael would do differently in the first 12-24 months if he started over * What's next for Yough! heading into the back half of 2026 If you're building in frozen, better-for-you, or any category where the product has to earn its place on a cold shelf, this episode is a candid look at what the grind before the breakthrough actually costs.

No Formula. No Co-Man. No Branding. Nationwide Whole Foods in Three Months.

What does it look like to sell a brand to Kraft Heinz for a reported $200 million, and then build the second one with three kids under seven and no social media on your phone? Morgan Zanotti, Founder and CEO of Waay, joins In The Money to break down what changed and what stayed the same the second time around. Waay is a fizzy, clear sparkling protein water, 10 grams of protein, 45 calories, zero sugar, built for women who are tired of choking down chalky shakes to hit their protein goals. Before Waay, Morgan co-founded Primal Kitchen alongside Mark Sisson, bootstrapped it to $50M in revenue profitably, and led the company through its $200 million acquisition by Kraft Heinz in 2019. We cover: * Why Morgan built Waay after watching the protein trend get sold entirely to men * The Primal Kitchen playbook: bootstrapping to $50M before the exit * What she learned inside Kraft Heinz about scale, GLP-1s, and category timing * Why she pitched Whole Foods with a silver can, no final formula, no co-manufacturer, and no branding, and how they said yes nationwide anyway * 18 months of formulation: getting real protein, zero sucralose, and a taste that doesn't announce itself * Building the entire brand identity in three months and launching by October * Why she went Whole Foods first instead of Target, and how that sequencing shaped everything that followed * The clear protein category: how it's exploding globally and why the US is just catching up * Building lean the second time: a small remote team built through referrals, no agency * Raising capital on traction versus raising on hopes and dreams * What she'd do exactly the same the second time, and what she's doing completely differently * Balancing three kids under seven with building a fast-scaling consumer brand If you're building a consumer brand, thinking about a second act after an exit, or trying to figure out how to build with intention instead of urgency, this episode is one of the most grounded founder conversations I've put out this year.

The Repeat Founder Who Learned to Focus On One Product that Actually Matters

What does it look like to build a premium hydration brand in one of the most crowded categories in consumer health, and win by doing almost everything differently? Joe Welstead, Co-Founder of Oshun, joins In The Money to break down how a repeat founder took every assumption about the electrolyte category and threw them out. No sachets. No citrus. No agency. No VC. Just a pump dispenser, an unflavored formula, and a brand positioning that owes more to skincare than sports nutrition. Joe built Motion Nutrition before this. He came out of that experience with one lesson above all others: launch one product, nail it completely, and resist every temptation to expand before you've earned the right to. At Oshun, he's done exactly that, and it's working. We cover: * Why Joe looked at LMNT, Liquid IV, Nuun, Hydrant, and Prime and saw an opportunity hiding in plain sight * The pump dispenser decision: why form factor is a marketing strategy, not just a packaging choice * Why Oshun has no flavor, and how that single decision sidesteps flavor fatigue and the endless SKU trap * The "clear skin, clear mind" moment: how a single conversation with a friend reframed the entire brand positioning overnight * Beauty adjacent, not supplement adjacent: why escaping the supplement category unlocks everything * Three months of real-world conversations before running a single ad, and why that made the first Meta campaigns perform from day one * How Joe learned to run Meta himself without an agency, and why he thinks the learning curve is overstated * The seeding to Meta funnel: how Oshun uses creator seeding to train the algorithm before spending a dollar on paid * Two co-founders, one product, 75-90% of scope focused entirely on growth * Why Oshun launched a magnesium sleep product, and the surprisingly simple customer reason that accelerated the timeline * Building in public without sharing revenue: why Joe talks about subscriber count and compound metrics but never top line * Profitable and growing while turning down institutional investors, what that optionality actually feels like * Skio's cancel flow as the single biggest retention unlock of 2026 * Why a skip or delay beats a discount every time for subscription churn * What Joe would do differently in the first 12 months of the next brand If you're building a consumer brand in health, wellness, or any crowded category where the default playbook isn't working — this episode is one of the clearest arguments I've heard for why doing less, better, wins.