How They Scaled It

PODCAST · business

How They Scaled It

Welcome to How They Scaled It, where scaling is done with both sides of the brain. Join host Courtney Wasserburger as she sits down with growth stage businesses; speaking with founders and industry leaders from eCommerce and SAAS sectors. We showcase their journeys, unpacking the pivotal moments, marketing strategies, and key decisions that shaped their success. If you’re a business owner, marketing leader, or entrepreneur eager to learn the ins and outs of scaling and thriving in the digital space, this podcast is your corner of the internet dedicated to helping you learn from the best.

  1. 29

    Build the Foundation, Then Scale w. Eric Fortenberry

    In this episode of How They Scaled It, I sit down with Eric Fortenberry, Founder and CEO of JobTread, as he shares how he built one of the fastest-growing platforms in construction tech. Starting with a chaotic, paper-based construction business, Eric stepped in to streamline operations, increase profitability, and create a scalable system now used by contractors nationwide. He unpacks the systems, mindset, and customer-first approach that fueled JobTread’s explosive growth.00:00:00 – Why most construction businesses can’t scale00:01:26 – Meet Eric Fortenberry, CEO of JobTread00:02:15 – How a one-year consulting gig turned into a tech company00:03:29 – The broken systems Eric walked into00:04:50 – Why no existing software fit—and why he built his own00:05:45 – How JobTread drove a 43% profit increase in one year00:07:10 – The difference between markup and margin00:08:46 – Fixing incentives with bid requests and work orders00:10:59 – Transitioning from hourly to fixed cost jobs00:13:24 – When Eric knew JobTread could be a platform00:15:42 – Getting buy-in from resistant team members00:18:12 – How JobTread supports implementation00:21:32 – Who JobTread is built for00:24:30 – Why estimating is the key to long-term stickiness00:30:57 – The dashboards and KPIs contractors care about00:34:42 – Managing product feedback from 50,000+ users00:39:47 – How JobTread built a winning team culture00:44:52 – The future of construction tech00:50:50 – Eric’s biggest lesson: Radical transparency wins

  2. 28

    Scaling a Mission-Driven Skincare Brand w. Cheree Ashley

    In this episode of How They Scaled It, I sit down with Cheree Ashley, Founder and CEO of Osier. Cheree went from opening treatment centers at the age of 24 to launching Osier, a skincare brand rooted in healing. In this episode, she shares how Osier was born from her personal recovery journey, why clean, affordable products are a form of self-care, and how she’s balancing growth, mission, and motherhood while scaling a purpose-driven DTC brand.00:00:13 — Cheree’s no-backup plan: why failure wasn’t an option00:00:34 — From recovery to skincare: how Osier was born00:03:03 — Why Cheree thrives in chaos—and how she makes it work00:04:48 — Lessons from trial-and-error in her first business00:06:44 — Building resilience through consistency and patience00:07:34 — The story behind the name “Osier” and its symbolism00:09:08 — Recovery, self-care, and skincare: how they connect00:10:52 — Getting vulnerable in the beauty industry00:12:06 — Osier’s giveback mission: funding treatment programs00:15:31 — The surprising timeline of product development00:16:27 — Stepping into the world of DTC and social media00:17:42 — Formulating products with Korean manufacturers00:20:47 — What’s worked for early traction: Amazon, TikTok Shop & pop-ups00:22:09 — The dream: scholarship recovery care through product sales00:24:36 — How Cheree leads teams with service and humility00:26:56 — Building structure through boundaries and good habits00:30:17 — Discipline = freedom: the power of routine00:32:18 — What’s next for Osier over the next 3–5 years00:33:08 — Advice Cheree would give her younger founder self00:34:48 — Letting go of control and trusting the process

  3. 27

    Build Credibility, Grow Your Business w. Rochelle Jacobs

    In this episode of How They Scaled It, I sit down with Rochelle Jacobs, Co-Founder of Naturally Serious and a Wall Street veteran who returned to her roots in skincare. Rochelle shares how she blended clinical efficacy with clean ingredients to build a brand that's redefining modern beauty. She talks about the power of partnerships, the lessons she learned launching just before the pandemic, and how learning to let go transformed her approach to growth. From bootstrapping a manufacturing facility to making clean beauty truly accessible, Rochelle’s story is a masterclass in purpose-driven leadership and quiet disruption.00:00:13 – The importance of the right retail partners00:00:36 – Meet Rochelle Jacobs00:01:47 – Beauty roots: Her family’s skincare legacy00:03:19 – Why finance came first and how she was pulled into skincare00:04:18 – Launching a manufacturing facility with zero experience00:05:47 – The hands-on MBA of building a beauty brand from scratch00:07:20 – Learning by doing00:08:27 – From spas to Sephora00:10:36 – Product philosophy: Simplicity, transparency, and great naming00:11:15 – Why fewer SKUs was a deliberate strategy00:12:19 – Defining “clean”00:14:25 – Clean meets clinical: Overcoming skepticism00:16:21 – How the brand encourages organic discovery and accessibility00:17:47 – Their patented antioxidant blend & anti-pollution edge00:22:11 – Partnering with hospitals00:25:13 – Creating healing products during breast cancer treatment00:26:40 – Leadership lessons: Letting go, trusting your team00:29:30 – Why word-of-mouth hiring still works00:30:12 – The myth of work-life balance00:32:29 – Biggest challenge: scaling in a TikTok-driven world00:34:45 – Trends, distractions, and your phone00:35:55 – Staying curious and humble as a founder00:36:51 – Advice to past self00:38:41 – Where to find Naturally Serious online

  4. 26

    Sell Top-Down, Scale Faster w. Andre Wouansi

    In this episode of How They Scaled It, I sit down with Andre Wouansi, Founder of Accurate Legal Billing. He shares how he went from auditing law firm invoices to building an AI-powered platform that’s saved firms over $225M in lost revenue. Hear how he overcame industry resistance, built a product without writing code, and why mindset is his most powerful leadership tool.00:00:13 – The mindset that drives Andre as an entrepreneur00:00:52 – Introducing Accurate Legal Billing (ALB)00:01:32 – From bill auditing to legal tech founder00:03:32 – Becoming part of the solution00:05:41 – Building a product without being a developer00:07:32 – Facing doubt and early industry resistance00:09:06 – Turning every “no” into a “yes”00:12:13 – How ALB evolved over the last 10 years00:14:40 – Going from unknown to industry standard00:17:00 – Landing ALB’s first enterprise clients00:20:18 – Turning opportunity into case studies00:24:32 – Why going straight to the top worked00:26:00 – How COVID shifted law firm tech adoption00:29:31 – Building tools for the next generation of lawyers00:33:06 – Quantifying impact: $225M saved00:35:01 – Leadership lessons and changing team mindset00:43:55 – Why purpose matters more than profit00:46:45 – The next five years for ALB

  5. 25

    Stop Selling Features, Start Selling Outcomes w. Pedro Arellano

    In this episode of How They Scaled It, I sit down with Pedro Arellano, Co-Founder and CEO of Wallabi. He shares how his 25-year journey through the data and analytics world led him to build a new kind of business intelligence platform. Listen now to learn how AI, accessibility, and empathy intersect to drive better business outcomes, and why simply having more dashboards doesn’t equate to impact.00:00:13 — Pedro introduces himself and credits his team00:00:51 — Courtney introduces Wallabi and Pedro’s background00:01:55 — From WarGames to coding on a Commodore 6400:02:45 — Discovering a passion for data in college00:03:35 — Early BI landscape: IT-controlled and exclusive00:04:45 — Two big disruptions: self-serve tools and generative AI00:06:47 — Why LLMs are the next wave in BI00:08:11 — The persistent issue of accessibility in analytics00:09:41 — Grounding product in real user problems00:11:08 — How to find valuable problems worth solving00:13:11 — The gradual “aha” that led to launching Wallabi00:15:33 — Moving from data access to contextual intelligence00:18:29 — Helping users act on insights, not just see them00:20:11 — What makes Wallabi exciting: solving existential business questions00:22:15 — The first customers: direct sales and digital marketing00:24:18 — Translating geek speak to real user pain00:26:58 — Balancing vision with user feedback00:28:56 — Avoiding the “order taker” trap00:30:01 — Thinking through fundraising and growth pace00:32:05 — Staying grounded as a founder00:36:37 — Human-first culture in a tech-first space00:38:11 — Pedro’s advice to new founders00:41:48 — Where to find Wallabi

  6. 24

    Retail Isn’t Luck, It’s Strategy w. Elina Wang

    In this episode of How They Scaled It, I sit down with Elina Wang, Co-Founder and CEO of ESW Beauty, as she shares the inspiring journey behind her wellness-driven skincare brand.From a $25,000 bank loan and DIY packaging to launching in major retailers like Kohl’s, Target, and Whole Foods, Elina reveals the hard-won lessons of retail partnerships, building a values-driven brand, and creating standout experiences through grassroots marketing and creative events.00:00:12 – Meet Elina Wang, founder of ESW Beauty00:01:16 – How her wellness journey inspired the first product00:03:14 – Taking a $25K leap and launching while in college00:04:47 – Formulating custom products with a biochem background00:05:41 – How a bold pitch at Cosmoprof landed Kohl’s00:07:38 – The art (and obsession) of packaging design00:09:32 – Differentiating in a crowded skincare market00:10:45 – Her co-founder story: from dating to dream team00:13:53 – Scaling from 2 people to a team of 15+00:16:11 – Landing Target and Walgreens after years of follow-up00:20:20 – Keeping brand vision aligned as you grow00:22:42 – Why every product launch is a huge team effort00:23:01 – Elina’s favorite unconventional marketing moment00:24:37 – Building connection through events and community00:27:18 – Elina’s personal rituals for staying grounded00:29:16 – Building a great team through thoughtful hiring00:30:59 – What’s next for ESW Beauty00:31:40 – Elina’s advice: Have a funding plan & be agile

  7. 23

    Building Trust Then Building the Brand w. Scott Kveton

    In this episode of How They Scaled It, I sit down with Scott Kveton, Co-Founder and CEO of CaseMark, who has a track record of building companies that define categories. Scott shares how intuition, scrappiness, and relentless customer focus shaped his journey, and why AI is set to transform legal tech in the same way the iPhone reshaped mobile.00:00:13 – Scott on brand-building struggles and leaning on experts00:00:52 – Courtney introduces Scott’s career journey00:01:39 – The three T’s: team, tech, timing00:03:06 – Learning to trust your gut as an entrepreneur00:04:28 – Investor skepticism and TAM projections00:07:08 – Urban Airship’s scrappy early launch00:09:26 – Lessons from Twilio’s Jeff Lawson00:12:18 – Why legal tech? The problem CaseMark solves00:14:39 – Starting small with “easy buttons”00:16:47 – Why AI will increase litigation00:20:59 – Simplifying the product for attorneys00:23:32 – Scaling medical chronology automation00:26:34 – CaseMark’s subject matter advantage (Scott’s wife as advisor)00:29:18 – The future of AI collapsing tools in legal00:30:04 – Scott’s evolving leadership style00:34:46 – Branding lessons00:38:59 – Advice for legal tech founders00:42:12 – What Scott wishes he knew at CaseMark’s start00:44:19 – Where to find CaseMark and connect with Scott

  8. 22

    Empowering Women by Scaling Community w. Dani Pickens

    In this episode of How They Scaled It, I sit down with Dani Pickens, Founder & Chief Enablement Officer of The Executive Evolution (TEE). Dani shares how a non-compete lawsuit, career pivots, and personal grit led her to build a growing women’s network for tech and channel professionals.With over 120 members across the US, TEE is redefining mentorship and support. No dues, no gatekeeping, just real talk and real community.00:00:13 – Meet Dani Pickens and The Executive Evolution00:01:33 – From Istanbul to door-to-door telecom sales00:03:27 – What selling DSL taught Dani about grit00:05:45 – Becoming Channel Chief before 4000:07:26 – The non-compete lawsuit that changed everything00:09:49 – Founding TEE out of personal pain00:12:26 – The idea behind "The Human Channel"00:15:56 – Building skills, sharing them freely00:17:09 – What makes TEE different from other networks00:20:32 – How TEE built a board from its first retreat00:25:04 – Organic growth and member referrals00:28:05 – Relaunching the mentorship program00:31:22 – Cross-generational mentoring in action00:33:33 – Annual Hope Kit fundraiser and impact00:39:26 – Balancing leadership, TEE, and family00:45:25 – Launching the Leadership Exchange program00:47:55 – Dani’s advice to herself on Day 1: stay the course

  9. 21

    Turning Expertise Into a Scalable Brand w. Claire Bing

    In this episode of How They Scaled It, I sit down with Claire Bing, Founder and CEO of Confiance Cosmetic Group. Confiance is a beauty and personal care consulting company specializing in regulatory and supply chain solutions for domestic and international sales.Claire didn’t set out to be a regulatory expert, but today she’s behind the compliance success of over 200 clients. From her start in a donut factory to scaling Confiance into an international consultancy, Claire shares how science, systems, and empathy became her formula for growth. She also opens up about evolving as a leader, using tech to scale smarter, and why clean beauty is about more than buzzwords.00:00:13 – Why Claire didn’t like the leader she used to be00:00:51 – Introduction to Confiance Cosmetic Group00:01:46 – How a microbiologist ended up in beauty00:03:34 – The pumpkin spice donut that launched her career00:04:47 – From Ohio to NYC: landing at Tarte Cosmetics00:05:49 – Becoming an accidental regulatory expert00:07:48 – Why she started her consultancy00:10:15 – The legal evolution of “clean beauty”00:14:49 – Arsenic is natural—so what does clean really mean?00:17:00 – Ingredients vs. process: where safety truly lies00:20:28 – Accidental business launch via LinkedIn00:23:01 – Building a mother-friendly, remote-first team00:31:54 – How tech and Notion keep everything running00:34:48 – Using Claude AI and PLM software to scale smarter00:37:35 – Why kindness is a business strategy00:40:41 – Claire’s leadership transformation00:48:04 – Redefining success and legacy00:50:39 – Claire’s vision for the future of Confiance00:54:23 – The one piece of advice she’d give her younger self

  10. 20

    Niche, Value, Then Scale w. Rick Clark

    In this episode of How They Scaled It, I sit down with Rick Clark, VP of Strategic Partnerships at CloudNine and Co-Founder of The Masters Conference.Rick has been on the frontlines of legal technology for over two decades. He has co-founded and developed several successful ventures including The Masters Conference, Wave Software, and ESI Analyst that have provided cutting-edge solutions and insights for complex data challenges.From converting texts into court-ready evidence to crafting conferences that matter, Rick dives into the lessons and challenges of scaling in a niche, slow-to-change industry—and how strong partnerships made it all possible.00:00:13 — How the pandemic changed digital evidence forever00:00:36 — Meet Rick Clark: founder, innovator, connector00:01:12 — Early days of discovery: from paper to digital00:02:07 — Why 2006 was a turning point for eDiscovery00:03:15 — Launching Wave Software at the perfect moment00:04:16 — Starting The Masters Conference over coffee00:05:55 — Differentiating in a sea of legal tech giants00:07:16 — Creating ESG Analyst for chat and mobile data00:09:11 — Pandemic-proof product-market fit00:10:20 — From emails to WhatsApp: the new digital trail00:12:42 — Scaling smart: how ESI Analyst stood out00:14:28 — Cross-channel threading and human behavior00:15:24 — Strategic differentiation in a crowded market00:16:12 — When acquisition becomes the smartest path00:19:51 — How The Masters Conference scaled to 15+ cities00:21:34 — Why local relevance drives lasting impact00:24:01 — AI adoption in legal: faster than ever before00:26:45 — How lawyers are (finally) catching up00:27:27 — Rick’s partnership strategy and why it works00:30:04 — Build your network, protect your reputation00:32:37 — Lessons Rick wishes he knew earlier00:35:42 — What’s next: education, thought leadership, and mentorship

  11. 19

    Scaling Smart: Quality Over Quantity w. Brittany Lo

    In this episode of How They Scaled It, I sit down with Brittany Lo, Founder and CEO of two separate beauty companies: Beia and Beautini. In this episode, she shares how building a wedding beauty concierge gave her the insight to launch Beia, a premium body care brand solving real, often unspoken problems.From launching during a pandemic to landing major retail partners and rebranding for scale, Brittany walks us through her intentional journey of building not just buzz, but businesses that last.00:00:13 – Why solving real problems matters in beauty00:00:50 – Brittany’s start with Beautini and the early insight that sparked Beia00:02:06 – The awkward (but real) questions that led to a product idea00:03:32 – Standing out in a saturated market with meaningful impact00:04:58 – Developing the first Beia product during a pandemic00:06:07 – How Brittany found her first manufacturer through relationships00:07:31 – Why she hired a chemist to keep full formula control00:09:27 – Seeding the launch through her network and the power of buy-in00:10:53 – The moment she knew she had a real customer, not just support00:13:03 – Using trade shows to break into retail early00:15:29 – Why Beia pivoted from intimacy branding to lifestyle skincare00:18:36 – How product quality won over retail buyers at Neiman Marcus00:20:43 – Building for premium customers with intentional pricing00:26:53 – Balancing profitability with brand integrity00:30:21 – The real metric she uses to measure success00:36:59 – Why Amazon became a breakout channel for Beia00:39:03 – Leadership, hiring slow, and protecting company culture00:44:26 – The advice she’d give her past self as a founder

  12. 18

    Identifying Your Brand’s “Why” w. Chelsey Hayes

    In this episode of How They Scaled It, I sit down with Chelsey Hayes, co-founder and CEO of Brown Babee. She shares how her decade-long fertility journey led to the creation of a purpose-driven skincare brand for infants and children with sensitive skin.From overcoming cancer and endometriosis to trusting her instincts and betting on herself, Chelsey opens up about building with intention, leading with story, and finding strength in community. This episode is a must-listen for early-stage founders who want to launch mindfully and scale with heart.00:00:13 – Chelsey introduces her 10-year path to motherhood00:00:48 – Courtney introduces Brown Babee and the episode00:01:27 – When Chelsey first knew she wanted to start a business00:03:05 – From federal government contracting to founder00:04:05 – Her daughter’s eczema diagnosis and early decisions00:06:12 – Learning to formulate through YouTube00:07:21 – Discovering her deeper “why”00:08:29 – Learning to listen to intuition and filter the noise00:10:00 – How surviving ovarian cancer shaped her mindset00:12:44 – Early hurdles: funding and timing00:14:17 – Betting on herself: the $90k turning point00:19:18 – A co-founder leaves—and the lesson in that loss00:21:54 – Balancing purpose with profitability00:24:02 – Strategic partnerships and quality-first mindset00:27:00 – Pushing back on the “move fast” mantra00:28:48 – Why she stayed true to the name Brown Babee00:33:08 – Accelerator programs and mentorship00:36:02 – Building community as a pre-launch brand00:40:03 – Her advice to her past self: “You are worthy”00:41:56 – Where to follow Brown Babee online

  13. 17

    Scaling Community Not Just Revenue w. Natalie Cantave

    In this episode of How They Scaled It, I sit down with Natalie Cantave, the co-founder of MKTG WMN—a thriving community designed to uplift women and nonbinary professionals in marketing. She shares how a chance conference meetup with her now co-founder sparked a movement, and how they’ve grown it into a mission-led, member-supported platform with real industry impact.Along the way, Natalie opens up about scaling without selling out, navigating imposter syndrome, and choosing intentionality over hype. From launching a paid model rooted in inclusivity to hosting IRL events with partners like Wistia, her story is a masterclass in building community with heart and a no-BS mindset.00:00:13 – Why values and no-BS culture were foundational00:01:21 – How Natalie and Gabrielle met and bonded over shared challenges00:03:14 – The catalyst moment during COVID00:04:39 – Early career lessons and salary transparency00:06:01 – Launching MKTG WMN and overcoming imposter syndrome00:07:10 – Going from events to mentorship and in-person meetups00:08:32 – When and why they transitioned to a paid model00:10:22 – How the community responded to monetization00:11:36 – Creating a support system across all marketing verticals00:14:11 – Highlights from co-working events and CEO conversations00:15:24 – What didn’t work (and how they pivoted)00:17:13 – Black Marketers Meetup and meaningful impact00:19:54 – Natalie’s past experience with partnerships00:21:29 – How they landed Wistia and Goldcast as sponsors00:25:04 – Why authenticity is central to their growth strategy00:28:31 – Scaling slowly and resisting profit-over-values temptation00:30:16 – Building mentorship programs during high-need times00:33:26 – Advice for founders building community00:36:40 – How newsletters and storytelling keep the brand human00:39:12 – What the future holds: team-building, more events, and 10-year vision

  14. 16

    DTC Lessons from a Tween Skincare Breakout w. Corina Pfeffer

    In this episode of How They Scaled It, I sit down with Corina Pfeffer, co-founder and COO of Pipa Skin Care, to unpack how a Venezuelan trio of moms turned a gap in the skincare market into a viral, best-selling DTC brand for tweens. With almost no paid ads, zero outside funding, and hands-on everything from fulfillment to customer service, Pipa is proving that thoughtful branding, organic growth, and a deep understanding of your customer can beat big budgets. Corina shares the scrappy strategies, operational lessons, and brand-building mindset that have powered their rapid rise—and what’s next as they scale.00:00:13 – Why customer experience is a core value at Pipa00:00:40 – Meet Corina Pfeffer and the founding story behind Pipa Skincare00:01:41 – How three childhood friends built a brand from a parenting problem00:02:52 – The moment they realized there was a real market gap00:04:27 – How each co-founder’s strengths shaped their success00:05:43 – The surprisingly sentimental story behind the name “Pipa”00:07:03 – Corina’s career path: from math to entrepreneurship00:09:18 – Lessons from a failed startup that shaped Pipa’s strategy00:10:59 – Why they insist on doing everything themselves—at first00:13:29 – How a focus on delight drives their customer experience00:15:31 – Their biggest challenge: explosive, unpredictable growth00:18:24 – Why they ran out of stock during their first holiday season00:19:12 – How they grew entirely through organic influencer buzz00:21:30 – The role of PR and how British Vogue found them00:23:17 – Pivotal moments that made them realize Pipa was taking off00:25:32 – New products, sunscreen success, and what’s coming next00:27:59 – Preparing for retail and what’s driving that shift00:28:59 – Selling out on Amazon—even without optimization00:30:23 – How living with their target customer (tweens!) helps00:32:44 – Navigating international demand (and expensive shipping)00:35:10 – Why they’re staying scrappy and bootstrapped00:37:55 – The surprising power of email marketing for DTC00:40:12 – Advice for career-changers and lifelong learners00:44:15 – What Corina would tell herself when starting out

  15. 15

    How Knowing Your Numbers Drives Growth w. Kunle Campell

    In this episode of How They Scaled It, I sit down with Kunle Campbell, co-founder of Octillion Capital Partners and host of the 2X eCommerce podcast. Kunle shares how a curiosity-fueled SEO career led him to the operator seat—where he now acquires and grows wellness-first brands through a private equity-style model rooted in purpose, not just profit.Along the way, Kunle breaks down how Octillion finds hero products, why subscriptions fuel their growth engine, and what it really takes to scale without compromising your values. From rebranding mushroom coffee to building founder-led stories that resonate, this episode is packed with sharp insights on sustainable, principle-driven growth in the DTC space.00:00:13 Kunle’s philosophy: growth vs. profitability00:01:37 How a lecture ignited Kunle’s e-commerce path00:04:01 Surviving the 2008 crash and building an SEO agency00:06:00 Discovering the limits of traffic without conversion00:07:21 Building the 2X eCommerce podcast and agency00:09:38 From consultant to operator: Why Kunle founded Octillion00:11:39 Meeting his business partner via Google00:14:17 The importance of financial literacy as an operator00:17:29 Using subscriptions to drive growth while preserving LTV00:23:04 Scaling brands vs. scaling products00:26:10 How they found a new hero product when the original went out of stock00:31:33 The cost of educating the market00:34:56 Why Octillion only invests in wellness-first brands00:40:34 Predictions for e-commerce, AI agents, and TikTok Shop00:50:11 The power of high-volume content production

  16. 14

    How to Grow in Retail Without Selling Out w. Cat Lepetit

    In this episode of How They Scaled It, I sit down with Cat Lepetit, the visionary founder of Sun Drunk, a beach lifestyle brand rooted in joy, sustainability, and good vibes. She shares how a day at the sandbar sparked a movement and how she built a community-driven business—one pop-up at a time. Along the way, Cat opens up about letting go of corporate playbooks, embracing slow growth, and redefining what success looks like on her own terms. From hand-selecting eco-conscious materials to building a fiercely loyal customer base face-to-face, her story is a lesson in intuitive, purpose-driven entrepreneurship.00:01 Meet Cat Lepetit and the birth of Sun Drunk01:21 The spark: a sandbar moment that inspired it all03:19 The missing market for moms at the beach05:12 Leaving corporate beauty to start fresh08:51 Launching Sun Drunk on French Revolution Day10:22 The reality of brand awareness in a noisy world11:48 Grassroots pop-ups as brand incubators14:42 Health-conscious events and finding product-market fit16:02 Staying sustainable without compromise19:25 More than towels: building a lifestyle and a vibe21:02 The challenge of branding something intangible24:03 Measuring success as a self-funded founder25:30 Creating superfans through live shopping27:21 Rejecting hollow innovation for timeless quality29:43 Going back to tradition over trends32:26 Dreaming bigger: stores, beach bars, and full experiences34:37 Advice to her past self: follow the joy, and trust your gut

  17. 13

    How Good Product Can Change Consumer Behavior w. Chaz Dean

    In this episode of How They Scaled It, I sit down with Chaz Dean, the visionary founder behind WEN Hair & Body Care. From starting out as a photographer to launching a billion-dollar beauty brand, Chaz shares how he pioneered the cleansing conditioner category, defied industry norms, and stayed true to his values—long before clean beauty was trending.He opens up about scrappy beginnings, getting burned early in business, developing a cult product in secret, and how a moment with Oprah changed everything. Whether you're a founder, beauty lover, or just into big brand stories with heart, this episode is a masterclass in trusting your gut and scaling with authenticity.00:13 Introduction to How They Scaled It00:36 From Photographer to Hairstylist03:37 Early Hustle and Building Confidence06:47 Why He Ditched Shampoo for Good10:48 Creating His First Product (and Getting Underpaid)15:04 Buying His First Salon and Changing the Game17:55 The No-Lather Revolution Begins21:58 Educating Clients and Perfecting the Formula27:17 Naming WEN and Launching the Brand33:52 Getting on QVC and Reaching the Masses36:29 Celebrity Fans, Oprah’s Endorsement, and the Tipping Point41:34 Trust, Confidence, and the Big Break44:27 Staying Authentic in a Flash-in-the-Pan Industry50:45 What Makes WEN Endure52:18 Final Thoughts and TakeawaysConnect with Courtney:LinkedIn: https://www.linkedin.com/in/courtney-wasserburger-14543519/Website: https://rightleftagency.com/Connect with Chaz Dean: Website: https://chazdean.com/Instagram: https://www.instagram.com/chazdean/

  18. 12

    Glitter, Grit, and Going Viral w. Fazit

    In this episode of How They Scaled It, I sit down with Aliett Buttelman and Nina LaBruna, the dynamic co-founders behind Fazit Beauty, the viral skincare and cosmetics brand redefining beauty with innovative patches (including their glitter freckle patches that Taylor Swift herself wore!).They share how they bootstrapped their brand with just $13K, leveraged TikTok to explode their sales, and navigated the challenges of building a business without investors. If you're a founder, marketer, or just obsessed with beauty and branding, this episode is packed with scrappy marketing tactics, co-founder wisdom, and lessons in scaling without selling out.00:13 Introduction to How They Scaled It00:33 Meet the Founders of Fazit Beauty01:20 The Journey to Launching Fazit07:33 The Challenges of Being a Young Entrepreneur15:10 The Power of Social Media Marketing19:20 Developing Innovative Products23:58 The Taylor Swift Viral Moment26:54 The Moment Everything Changed29:02 The Power of Authenticity29:41 Strategic Celebrity Endorsements36:41 Navigating Inventory Challenges41:14 Lessons from Past Experiences46:28 Future Plans and Advice50:55 Conclusion and Final ThoughtsFollow Courtney and Fazit:Connect with Courtney: LinkedIn: https://www.linkedin.com/in/courtney-wasserburger-14543519/Website: https://rightleftagency.com/about/Connect with Fazit: Website: https://fazitbeauty.com/

  19. 11

    Scaling a Luxury Brand w. Lita Cunningham

    In this episode of How They Scaled It, Isit down with Lita Cunningham, founder and CEO of Lalais, a luxury skincare brand redefining solutions for misunderstood skin.From her corporate HR career to creating an award-winning skincare brand, Lita shares how a personal frustration with available skincare options led her to take a leap into entrepreneurship. In just 13 months, Lalais has landed in Neiman Marcus, made it onto Oprah’s Favorite Things, and won multiple industry awards.00:00 Introduction and Personal Story00:22 Welcome to How They Scaled It00:42 Meet Lita Cunningham01:06 From Corporate HR to Entrepreneur04:26 Developing the Perfect Skincare Formula09:17 Challenges and Triumphs in Product Development15:22 Retail Success and Oprah's Favorite Things21:34 Creating a Luxury Customer Experience26:46 Overcoming Entrepreneurial Challenges32:38 Future Plans and Advice for Founders42:27 Conclusion and Final ThoughtsFollow Courtney and Lita:Connect with Courtney: LinkedIn: https://www.linkedin.com/in/courtney-wasserburger-14543519/Website: https://rightleftagency.com/about/Connect with Lita: LinkedIn: https://www.linkedin.com/in/lita-cunningham-21074813/Instagram:@glamlitanycFollow Lalais:Website:lalais.comInstagram: @lalaisskincare

  20. 10

    Breaking Into an Untapped Market w. Lekha Vyas

    How do you build a skincare brand that breaks stigma and empowers men to look and feel their best? In this episode, I chat with Lekha Vyas, the founder and CEO of Elvy Lab, a groundbreaking men's skincare brand she launched in 2022. Lekha's journey from working with beauty giants like L'Oréal, Estée Lauder, and Chanel to becoming a trailblazing entrepreneur is inspiring. Today, Lekha is well on her way to scaling Elvy Lab into a legacy brand with lasting impact in the cosmetic hygiene market. 00:37 Introducing Laika Vyas and Elvy Lab01:09 Laika's Journey in the Beauty Industry05:11 Identifying the Gap in Men's Skincare07:53 Challenges and Strategies in Men's Grooming20:07 Transitioning from Big Brands to Startups21:04 Recognizing Burnout and Embracing Slow Days21:25 The Rewards and Challenges of Being a Founder22:17 The Importance of Growth and Small Wins24:15 Advice for Aspiring Founders35:09 The Reality of Retail and Advertising Costs36:52 Final Reflections and AdviceFollow Courtney and Lekha:Connect with Courtney: LinkedIn: https://www.linkedin.com/in/courtney-wasserburger-14543519/Website: https://rightleftagency.com/about/gmaConnect with Lekha: LinkedIn: https://www.linkedin.com/in/lekhavyas/Website: https://elvylab.com/Lekha’s Instagram: https://www.instagram.com/lekahontas/?hl=enElvy Lab’s Instagram: https://www.instagram.com/elvy_lab/?hl=en

  21. 9

    Scaling DTC Brands w. Jessie Healy

    In this episode, I sit down with Jessie Healy, a celebrated marketer and the founder of Ecomm Rockets Coaching Group, a platform that helps DTC brands scale profitably by focusing on foundational business strategies. As the former owner of Webtopia, Jessie scaled her agency to 20 employees, worked with global clients, and eventually sold the business to focus on coaching and consulting. 00:00 Introduction to How They Scaled It 00:52 Jessie Healy's Journey to Webtopia 04:07 Challenges and Strategies in Growing an Agency 09:57 Transition to Coaching and Consulting 11:56 Balancing Business and Personal Life 20:13 Creating Profitable Ad Campaigns 24:14 The Essence of a Great Ad 26:07 The Importance of Intention in Advertising 27:08 Balancing In-House and Outsourced Content Creation 28:35 Navigating Profitability and Pricing Strategies 32:56 Scaling Your Business: Systems and Processes 40:58 Leveraging AI for Early-Stage Businesses 42:52 Advice for Aspiring Entrepreneurs Follow Courtney and Jessie: Connect with Courtney:  LinkedIn: https://www.linkedin.com/in/courtney-wasserburger-14543519/ Website: https://rightleftagency.com/about/ Connect with Sarah:  LinkedIn: https://www.linkedin.com/in/ecommercecoach/ Website: https://www.jessiehealy.com/

  22. 8

    The Psychology of Scaling w. Sarah Levinger

    Customer behavior, identity, and emotions have the biggest impact on the success or failure of your marketing efforts. Still, so many businesses are unable to account for consumer psychology. This week on How They Scaled It, I had the absolute pleasure of chatting with Sarah Levinger, a Forbes-featured consumer behavior analyst, creative strategist, and performance creative consultant. Sarah is an expert at bridging the gap between psychology and marketing, helping D2C brands like Hexclad, True Classic, Fabletics, and others boost their paid advertising ROI by creating deep emotional connections with their customers. Now, she’s at the head of Tether Insights, where she helps other businesses apply behavioral science to produce faster and more meaningful results.   00:00 Introduction  00:38 Meet Sarah Levinger: Consumer Behavior Expert 03:37 The Power of Emotional Connections in Marketing 13:10 The Role of Surveys and Reviews 17:32 Understanding Generational Differences 22:19 Balancing Psychology and Authenticity in Branding 26:46 The Evolution of Trust in Brands 29:34 The Importance of Humanizing Your Brand 32:48 Future Consumer Expectations 35:34 Behavioral Analysis in Marketing 48:25 Advice for Aspiring Entrepreneurs 50:55 Conclusion and Final Thoughts Follow Courtney and Sarah: Connect with Courtney:  LinkedIn: https://www.linkedin.com/in/courtney-wasserburger-14543519/ Website: https://rightleftagency.com/about/ Connect with Sarah:  Tether Insights: https://www.tetherinsights.io/ LinkedIn: https://www.linkedin.com/in/sarahlevinger

  23. 7

    Scaling Niche Markets w. Chris Doyle

    Welcome back to How They Scaled It, the podcast where scaling businesses meets innovation, strategy, and a little bit of grit. Today, I sit down with Chris Doyle, the President and CEO of Billd —a financial solutions company that empowers subcontractors across the U.S. Chris shared his journey from identifying inefficiencies in the construction industry to launching Billd as a game-changing solution for financial growth. If you’re curious about what it takes to innovate in a niche market like construction finance—and to do it profitably—this episode is for you. 00:00 Introduction 00:28 Meet Chris Doyle 01:02 Founding Billd: The Vision and Challenges 06:25 Customer Relationships and Financial Health 08:54 Innovative Financial Solutions and Market Education 18:12 Data-Driven Decision Making and Industry Disruption 21:41 Effective Marketing Strategies for Growth 27:40 Adapting Leadership Styles in a Growing Company 33:23 Handling Economic Fluctuations and Growth Challenges 37:33 Focusing on Core Strengths and Future Plans 40:28 Decision-Making and Conviction as a CEO 45:47 Advice for Aspiring Founders 47:44 The Story Behind the Company Name 50:48 Conclusion and Final Thoughts Follow Courtney and Chris: Connect with Courtney:  LinkedIn: https://www.linkedin.com/in/courtney-wasserburger-14543519/ Website: https://rightleftagency.com/ Connect with Chris:  LinkedIn: https://www.linkedin.com/in/christopherldoyle/ Website: https://billd.com/

  24. 6

    Building A Brand With Heart w. Betsy Neptune

    On this episode of How They Scaled It, we take a unique turn and explore scaling in the nonprofit world with Betsy Neptune, the Executive Director of BUILD Boston. BUILD empowers high school students from under-resourced communities to become CEOs of their own lives through entrepreneurship. Betsy shares how BUILD equips Gen Alpha with essential entrepreneurial skills like collaboration, problem-solving, and grit. We uncover BUILD’s unique approach of integrating its programs into schools, scaling through partnerships with teachers, and the crucial role of volunteer business coaches. Betsy also discusses the challenges of scaling a nonprofit sustainably in today’s economic climate and how BUILD’s impact prepares students not only for business but for life. 00:00 Introduction to How They Scaled It 00:41 Meet Betsy Neptune: Empowering Youth Through Entrepreneurship 01:51 The Origin and Evolution of BUILD 03:37 BUILD's Unique Approach to Teaching Entrepreneurship 07:25 Year One: Business Ideation and Design Thinking 11:14 Year Two: Making the Business a Reality 21:43 The Role of Business Team Coaches 26:18 Future Leaders: BUILD's Impact on Students' Careers 30:02 Challenges in Business and Workforce 31:03 Corporate Partnerships and Shared Value 31:59 Scaling BUILD: Strategies and Challenges 47:04 BUILD's National Expansion and Future Plans 51:11 Advice for Aspiring Professionals 53:32 How to Get Involved with BUILD Learn more about Courtney, Right Left Agency, and BUILD:  Courtney Wasserburger: LinkedIn | Right Left Agency Betsy Neptune: BUILD.org/Boston

  25. 5

    The Power of Email Marketing w. Alex Persson

    This week on How They Scaled It, I had the pleasure of sitting down with Alex Persson, the CEO of Privy. Alex is one of those leaders who just gets it—how to build brands that thrive by focusing on what matters most: their customers. We dive deep into: Retention marketing: Why it’s the key to scaling, and how Privy is helping brands succeed. Balancing automation and authenticity: A smarter way to use email and SMS. Lessons from acquisitions: How Alex identifies winners and scales them. Trends shaping e-commerce: The future of tools like AI in marketing. If you’ve ever wondered how to build real connections with your customers or want strategies to maximize your email and SMS impact, this episode is for you. Tune in now for all the insights and actionable tips! 00:28 Meet Alex Persson: Scaling E-commerce with Privy 01:10 Customer-Centric Culture at Privy 03:04 Driving Innovation Through Customer Feedback 05:49 Measuring Success in SaaS 08:25 Challenges and Strategies in SaaS Growth 10:55 Acquisitions: Lessons and Strategies 17:31 Future Trends in E-commerce Tools 21:12 The Power of Niche Marketing 22:44 Authenticity in Email Marketing 24:39 Understanding Your Audience 27:31 The Role of Automation 30:51 Common Mistakes in Email Marketing 35:33 Future Plans for Privy 38:23 Long-Term Success Tips 39:43 Conclusion and Final Thoughts Connect with Courtney: LinkedIn: https://www.linkedin.com/in/courtney-wasserburger-14543519/  Right Left Agency: https://rightleftagency.com/about/  Connect with Alex:  LinkedIn: https://www.linkedin.com/in/perssonalex/  Privy: https://www.privy.com/ 

  26. 4

    Scaling Influencer Marketing w. Jake Hay

    Ever wondered what sets successful influencer marketing apart from just another viral post? In this episode, I sit down with Jake Hay, partner at PopShorts, a top influencer marketing agency, to unpack the real journey behind building a lasting brand through authentic influence. From the inception of PopShorts to the complexities of financing and scaling, Jake shares invaluable insights on blending strategy with creativity in a fast-paced industry. Learn about the pivotal moments, key strategies, and challenges they faced working with top-tier brands like Disney and Netflix. This conversation reveals the tactics brands need to know to make influencer marketing work and the behind-the-scenes decisions that keep businesses thriving. 00:24 Meet Jake: Partner at PopShorts 01:07 Early Challenges in Influencer Marketing 02:25 Financial Hurdles and Scaling Strategies 04:22 Educating Clients and Building Case Studies 06:45 Adapting to Industry Changes and Trends 08:59 The Role of AI and AR/VR in Marketing 14:07 Micro vs. Macro Influencers 17:58 Paid Media and Omni-Channel Strategies 23:06 Campaign Metrics and Guarantees 23:46 Influencer Content vs. Branded Content 25:04 Identifying Real Influence 25:44 Brand Safety and Influencer Costs 26:31 Diversity in Campaigns 27:17 Digital Footprint and Content Strategy 28:45 The PopShorts Journey 32:49 Challenges of Scaling a Project-Based Business 35:04 Leadership and Internship Program 38:38 Future of Influencer Marketing and PopShorts 40:30 Final Thoughts and Advice Learn more about Courtney and Right Left Agency: https://rightleftagency.com/ Follow Courtney and Jake: Connect with Courtney:  LinkedIn: https://www.linkedin.com/in/courtney-wasserburger-14543519/ Right Left Agency: https://www.linkedin.com/company/right-left-agency/ Connect with Jake & PopShorts:  LinkedIn: https://www.linkedin.com /in/imnotjustkiddin/ PopShorts: https://popshorts.com/

  27. 3

    Franchise Marketing Secrets w. Alex Pujji

    Welcome to How They Scaled It! I’m Courtney, and today, we’re going deep into the world of franchise marketing with someone who’s truly mastered the game. Meet Alex Pujji – founder of Right Left Agency and former head of growth of the franchise Pinspiration. Alex has been on an incredible journey, turning Pinspiration from a small two-location startup into a thriving franchise with over 45 locations! She’s here to break down what it takes to market and grow a franchise, sharing the strategies, grit, and key moves that made it all happen. 00:25 Meet Alex Pujji: Founder of Right Left Agency 00:53 Starting Right Left Agency: The Early Days 02:54 Choosing the Right Marketing Niche 04:29 Scaling with the Right Team 05:29 First Big Success: Pink Dust Cosmetics 07:58 Venturing into Franchising with Pinspiration 11:51 Challenges and Strategies in Franchise Marketing 23:13 The Future of Franchise Marketing 24:30 Personal Reflections and Advice 33:34 Conclusion and Farewell Follow Courtney and Alex: Connect with Courtney:  LinkedIn: https://www.linkedin.com/in/courtney-wasserburger-14543519/ Right Left Agency: https://www.linkedin.com/company/right-left-agency/ Connect with Alex:  LinkedIn: https://www.linkedin.com/in/alexpujji/

  28. 2

    Trailer: How They Scaled It

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ABOUT THIS SHOW

Welcome to How They Scaled It, where scaling is done with both sides of the brain. Join host Courtney Wasserburger as she sits down with growth stage businesses; speaking with founders and industry leaders from eCommerce and SAAS sectors. We showcase their journeys, unpacking the pivotal moments, marketing strategies, and key decisions that shaped their success. If you’re a business owner, marketing leader, or entrepreneur eager to learn the ins and outs of scaling and thriving in the digital space, this podcast is your corner of the internet dedicated to helping you learn from the best.

HOSTED BY

Right Left Agency

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