How They Scaled It

Right Left Agency
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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. Build the Foundation, Then Scale w. Eric Fortenberry

    JAN 8

    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 scale 00:01:26 – Meet Eric Fortenberry, CEO of JobTread 00:02:15 – How a one-year consulting gig turned into a tech company 00:03:29 – The broken systems Eric walked into 00:04:50 – Why no existing software fit—and why he built his own 00:05:45 – How JobTread drove a 43% profit increase in one year 00:07:10 – The difference between markup and margin 00:08:46 – Fixing incentives with bid requests and work orders 00:10:59 – Transitioning from hourly to fixed cost jobs 00:13:24 – When Eric knew JobTread could be a platform 00:15:42 – Getting buy-in from resistant team members 00:18:12 – How JobTread supports implementation 00:21:32 – Who JobTread is built for 00:24:30 – Why estimating is the key to long-term stickiness 00:30:57 – The dashboards and KPIs contractors care about 00:34:42 – Managing product feedback from 50,000+ users 00:39:47 – How JobTread built a winning team culture 00:44:52 – The future of construction tech 00:50:50 – Eric’s biggest lesson: Radical transparency wins

    53 min
  2. Scaling a Mission-Driven Skincare Brand w. Cheree Ashley

    12/11/2025

    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 option 00:00:34 — From recovery to skincare: how Osier was born 00:03:03 — Why Cheree thrives in chaos—and how she makes it work 00:04:48 — Lessons from trial-and-error in her first business 00:06:44 — Building resilience through consistency and patience 00:07:34 — The story behind the name “Osier” and its symbolism 00:09:08 — Recovery, self-care, and skincare: how they connect 00:10:52 — Getting vulnerable in the beauty industry 00:12:06 — Osier’s giveback mission: funding treatment programs 00:15:31 — The surprising timeline of product development 00:16:27 — Stepping into the world of DTC and social media 00:17:42 — Formulating products with Korean manufacturers 00:20:47 — What’s worked for early traction: Amazon, TikTok Shop & pop-ups 00:22:09 — The dream: scholarship recovery care through product sales 00:24:36 — How Cheree leads teams with service and humility 00:26:56 — Building structure through boundaries and good habits 00:30:17 — Discipline = freedom: the power of routine 00:32:18 — What’s next for Osier over the next 3–5 years 00:33:08 — Advice Cheree would give her younger founder self 00:34:48 — Letting go of control and trusting the process

    36 min
  3. Build Credibility, Grow Your Business w. Rochelle Jacobs

    10/30/2025

    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 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

    39 min
  4. Sell Top-Down, Scale Faster w. Andre Wouansi

    10/16/2025

    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 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

    52 min
  5. Stop Selling Features, Start Selling Outcomes w. Pedro Arellano

    10/02/2025

    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 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

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

    09/18/2025

    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 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

    36 min
  7. Building Trust Then Building the Brand w. Scott Kveton

    09/04/2025

    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 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

    45 min
  8. Empowering Women by Scaling Community w. Dani Pickens

    08/21/2025

    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 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

    50 min
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About

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.

Information

  • Creator
    Right Left Agency
  • Years Active
    2024 - 2026
  • Episodes
    28
  • Rating
    Clean
  • Copyright
    © Right Left Agency
  • Show Website
    How They Scaled It