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 partners

00:00:36 – Meet Rochelle Jacobs

00:01:47 – Beauty roots: Her family’s skincare legacy

00:03:19 – Why finance came first and how she was pulled into skincare

00:04:18 – Launching a manufacturing facility with zero experience

00:05:47 – The hands-on MBA of building a beauty brand from scratch

00:07:20 – Learning by doing

00:08:27 – From spas to Sephora

00:10:36 – Product philosophy: Simplicity, transparency, and great naming

00:11:15 – Why fewer SKUs was a deliberate strategy

00:12:19 – Defining “clean”

00:14:25 – Clean meets clinical: Overcoming skepticism

00:16:21 – How the brand encourages organic discovery and accessibility

00:17:47 – Their patented antioxidant blend & anti-pollution edge

00:22:11 – Partnering with hospitals

00:25:13 – Creating healing products during breast cancer treatment

00:26:40 – Leadership lessons: Letting go, trusting your team

00:29:30 – Why word-of-mouth hiring still works

00:30:12 – The myth of work-life balance

00:32:29 – Biggest challenge: scaling in a TikTok-driven world

00:34:45 – Trends, distractions, and your phone

00:35:55 – Staying curious and humble as a founder

00:36:51 – Advice to past self

00:38:41 – Where to find Naturally Serious online

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 entrepreneur

00:00:52 – Introducing Accurate Legal Billing (ALB)

00:01:32 – From bill auditing to legal tech founder

00:03:32 – Becoming part of the solution

00:05:41 – Building a product without being a developer

00:07:32 – Facing doubt and early industry resistance

00:09:06 – Turning every “no” into a “yes”

00:12:13 – How ALB evolved over the last 10 years

00:14:40 – Going from unknown to industry standard

00:17:00 – Landing ALB’s first enterprise clients

00:20:18 – Turning opportunity into case studies

00:24:32 – Why going straight to the top worked

00:26:00 – How COVID shifted law firm tech adoption

00:29:31 – Building tools for the next generation of lawyers

00:33:06 – Quantifying impact: $225M saved

00:35:01 – Leadership lessons and changing team mindset

00:43:55 – Why purpose matters more than profit

00:46:45 – The next five years for ALB

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 team

00:00:51 — Courtney introduces Wallabi and Pedro’s background

00:01:55 — From WarGames to coding on a Commodore 64

00:02:45 — Discovering a passion for data in college

00:03:35 — Early BI landscape: IT-controlled and exclusive

00:04:45 — Two big disruptions: self-serve tools and generative AI

00:06:47 — Why LLMs are the next wave in BI

00:08:11 — The persistent issue of accessibility in analytics

00:09:41 — Grounding product in real user problems

00:11:08 — How to find valuable problems worth solving

00:13:11 — The gradual “aha” that led to launching Wallabi

00:15:33 — Moving from data access to contextual intelligence

00:18:29 — Helping users act on insights, not just see them

00:20:11 — What makes Wallabi exciting: solving existential business questions

00:22:15 — The first customers: direct sales and digital marketing

00:24:18 — Translating geek speak to real user pain

00:26:58 — Balancing vision with user feedback

00:28:56 — Avoiding the “order taker” trap

00:30:01 — Thinking through fundraising and growth pace

00:32:05 — Staying grounded as a founder

00:36:37 — Human-first culture in a tech-first space

00:38:11 — Pedro’s advice to new founders

00:41:48 — Where to find Wallabi

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 Beauty

00:01:16 – How her wellness journey inspired the first product

00:03:14 – Taking a $25K leap and launching while in college

00:04:47 – Formulating custom products with a biochem background

00:05:41 – How a bold pitch at Cosmoprof landed Kohl’s

00:07:38 – The art (and obsession) of packaging design

00:09:32 – Differentiating in a crowded skincare market

00:10:45 – Her co-founder story: from dating to dream team

00:13:53 – Scaling from 2 people to a team of 15+

00:16:11 – Landing Target and Walgreens after years of follow-up

00:20:20 – Keeping brand vision aligned as you grow

00:22:42 – Why every product launch is a huge team effort

00:23:01 – Elina’s favorite unconventional marketing moment

00:24:37 – Building connection through events and community

00:27:18 – Elina’s personal rituals for staying grounded

00:29:16 – Building a great team through thoughtful hiring

00:30:59 – What’s next for ESW Beauty

00:31:40 – Elina’s advice: Have a funding plan & be agile

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 experts

00:00:52 – Courtney introduces Scott’s career journey

00:01:39 – The three T’s: team, tech, timing

00:03:06 – Learning to trust your gut as an entrepreneur

00:04:28 – Investor skepticism and TAM projections

00:07:08 – Urban Airship’s scrappy early launch

00:09:26 – Lessons from Twilio’s Jeff Lawson

00:12:18 – Why legal tech? The problem CaseMark solves

00:14:39 – Starting small with “easy buttons”

00:16:47 – Why AI will increase litigation

00:20:59 – Simplifying the product for attorneys

00:23:32 – Scaling medical chronology automation

00:26:34 – CaseMark’s subject matter advantage (Scott’s wife as advisor)

00:29:18 – The future of AI collapsing tools in legal

00:30:04 – Scott’s evolving leadership style

00:34:46 – Branding lessons

00:38:59 – Advice for legal tech founders

00:42:12 – What Scott wishes he knew at CaseMark’s start

00:44:19 – Where to find CaseMark and connect with Scott

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 Evolution

00:01:33 – From Istanbul to door-to-door telecom sales

00:03:27 – What selling DSL taught Dani about grit

00:05:45 – Becoming Channel Chief before 40

00:07:26 – The non-compete lawsuit that changed everything

00:09:49 – Founding TEE out of personal pain

00:12:26 – The idea behind "The Human Channel"

00:15:56 – Building skills, sharing them freely

00:17:09 – What makes TEE different from other networks

00:20:32 – How TEE built a board from its first retreat

00:25:04 – Organic growth and member referrals

00:28:05 – Relaunching the mentorship program

00:31:22 – Cross-generational mentoring in action

00:33:33 – Annual Hope Kit fundraiser and impact

00:39:26 – Balancing leadership, TEE, and family

00:45:25 – Launching the Leadership Exchange program

00:47:55 – Dani’s advice to herself on Day 1: stay the course

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 be

00:00:51 – Introduction to Confiance Cosmetic Group

00:01:46 – How a microbiologist ended up in beauty

00:03:34 – The pumpkin spice donut that launched her career

00:04:47 – From Ohio to NYC: landing at Tarte Cosmetics

00:05:49 – Becoming an accidental regulatory expert

00:07:48 – Why she started her consultancy

00:10:15 – 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 lies

00:20:28 – Accidental business launch via LinkedIn

00:23:01 – Building a mother-friendly, remote-first team

00:31:54 – How tech and Notion keep everything running

00:34:48 – Using Claude AI and PLM software to scale smarter

00:37:35 – Why kindness is a business strategy

00:40:41 – Claire’s leadership transformation

00:48:04 – Redefining success and legacy

00:50:39 – Claire’s vision for the future of Confiance

00:54:23 – The one piece of advice she’d give her younger self

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 forever

00:00:36 — Meet Rick Clark: founder, innovator, connector

00:01:12 — Early days of discovery: from paper to digital

00:02:07 — Why 2006 was a turning point for eDiscovery

00:03:15 — Launching Wave Software at the perfect moment

00:04:16 — Starting The Masters Conference over coffee

00:05:55 — Differentiating in a sea of legal tech giants

00:07:16 — Creating ESG Analyst for chat and mobile data

00:09:11 — Pandemic-proof product-market fit

00:10:20 — From emails to WhatsApp: the new digital trail

00:12:42 — Scaling smart: how ESI Analyst stood out

00:14:28 — Cross-channel threading and human behavior

00:15:24 — Strategic differentiation in a crowded market

00:16:12 — When acquisition becomes the smartest path

00:19:51 — How The Masters Conference scaled to 15+ cities

00:21:34 — Why local relevance drives lasting impact

00:24:01 — AI adoption in legal: faster than ever before

00:26:45 — How lawyers are (finally) catching up

00:27:27 — Rick’s partnership strategy and why it works

00:30:04 — Build your network, protect your reputation

00:32:37 — Lessons Rick wishes he knew earlier

00:35:42 — What’s next: education, thought leadership, and mentorship

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 beauty

00:00:50 – Brittany’s start with Beautini and the early insight that sparked Beia

00:02:06 – The awkward (but real) questions that led to a product idea

00:03:32 – Standing out in a saturated market with meaningful impact

00:04:58 – Developing the first Beia product during a pandemic

00:06:07 – How Brittany found her first manufacturer through relationships

00:07:31 – Why she hired a chemist to keep full formula control

00:09:27 – Seeding the launch through her network and the power of buy-in

00:10:53 – The moment she knew she had a real customer, not just support

00:13:03 – Using trade shows to break into retail early

00:15:29 – Why Beia pivoted from intimacy branding to lifestyle skincare

00:18:36 – How product quality won over retail buyers at Neiman Marcus

00:20:43 – Building for premium customers with intentional pricing

00:26:53 – Balancing profitability with brand integrity

00:30:21 – The real metric she uses to measure success

00:36:59 – Why Amazon became a breakout channel for Beia

00:39:03 – Leadership, hiring slow, and protecting company culture

00:44:26 – The advice she’d give her past self as a founder

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 motherhood

00:00:48 – Courtney introduces Brown Babee and the episode

00:01:27 – When Chelsey first knew she wanted to start a business

00:03:05 – From federal government contracting to founder

00:04:05 – Her daughter’s eczema diagnosis and early decisions

00:06:12 – Learning to formulate through YouTube

00:07:21 – Discovering her deeper “why”

00:08:29 – Learning to listen to intuition and filter the noise

00:10:00 – How surviving ovarian cancer shaped her mindset

00:12:44 – Early hurdles: funding and timing

00:14:17 – Betting on herself: the $90k turning point

00:19:18 – A co-founder leaves—and the lesson in that loss

00:21:54 – Balancing purpose with profitability

00:24:02 – Strategic partnerships and quality-first mindset

00:27:00 – Pushing back on the “move fast” mantra

00:28:48 – Why she stayed true to the name Brown Babee

00:33:08 – Accelerator programs and mentorship

00:36:02 – Building community as a pre-launch brand

00:40:03 – Her advice to her past self: “You are worthy”

00:41:56 – Where to follow Brown Babee online