Courtney Caldwell is the cofounder and CEO of ShearShare, the largest provider of on-demand salon and barbershop space rentals. With two decades of experience leading tech marketing teams, she has built a reputation as a trailblazing entrepreneur at the intersection of technology and the beauty industry.
Her award-winning leadership has transformed how independent stylists and barbers access workspace while promoting equity and inclusion across the tech landscape. As a sought-after keynote speaker, Courtney combines storytelling with actionable strategies that resonate with audiences ranging from entrepreneurs and executives to community leaders and students.
She speaks widely on entrepreneurship, leadership, future of work, digital innovation, and diversity in technology.
Courtney Caldwell is a dynamic and innovative force in the beauty-tech industry, serving as the Cofounder & CEO of ShearShare, the largest provider of on-demand salon and barbershop space rentals and the most affordable leases in the market. With a keen entrepreneurial spirit and a passion for transforming the beauty industry, Courtney has built a platform that empowers beauty professionals to maximize their potential and flexibility.
A distinguished tech founder and award-winning entrepreneur, Courtney brings two decades of experience in building successful teams in tech marketing. Her strategic acumen and innovative approach have earned her numerous accolades and a reputation as a trailblazer in her field. Through ShearShare, Courtney has harnessed the power of technology to address a critical need in the beauty industry, creating a unique solution that resonates with both salon owners and beauty professionals.
Beyond her entrepreneurial achievements, Courtney Caldwell is a sought-after keynote speaker, known for her engaging presentations and insightful perspectives on technology, entrepreneurship, and the future of work. Her ability to connect with diverse audiences and inspire change makes her a prominent figure on the global speaking circuit.
Courtney Caldwell’s journey to becoming a leading figure in the beauty-tech industry is marked by her extensive experience in tech marketing and her entrepreneurial prowess. Before founding ShearShare, Courtney spent over 20 years in various leadership roles, where she honed her skills in building and leading high-performing teams. Her background in tech marketing has equipped her with a deep understanding of digital transformation and the innovative application of technology in traditional industries.
As the CEO of ShearShare, Courtney Caldwell has overseen the company’s rapid growth and expansion, positioning it as a game-changer in the beauty industry. ShearShare’s platform addresses a significant gap in the market by providing a flexible, on-demand solution for salon and barbershop space rentals. Under her leadership, the company has attracted substantial investment, expanded its user base, and continually innovated its offerings to meet the evolving needs of beauty professionals.
As a keynote speaker, Courtney’s engaging style and deep insights make her a sought-after presenter at conferences and events worldwide. Her ability to inspire and connect with diverse audiences, coupled with her practical advice and real-world examples, ensures that her talks leave a lasting impact.
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Married cofounders Dr. Tye and Courtney Caldwell share how ShearShare grew from a salon problem to a VC-backed marketplace, plus hard-won lessons on risk, resilience, and community.
The episode opens with 43North hosts welcoming ShearShare cofounders Dr. Tye and Courtney Caldwell and inviting a quick elevator pitch. Courtney explains ShearShare as a platform that fills empty salon, spa, and barbershop chairs by the day or week, helping owners earn from unused space while giving licensed pros flexible work options. The hosts pivot to the founders’ journey and funding realities. Courtney notes being among a relatively small cohort of Black women to raise venture capital and outlines common investor biases toward married cofounders. She reframes the relationship as an advantage: deep trust, complementary strengths, and constant alignment.
Tye recounts the 2012 origin story. After expanding his salon with new suites, stations sat idle until a stylist asked to rent short-term. The experience proved demand for flexible access. As requests snowballed, the couple searched for an “Airbnb for salon chairs,” found no solution, and decided to build it. Tye introduces his book “Mentored by Failure,” outlining a five-point guide: be focused, be professional, build your best brand, be smart about money, and be consistent. The discussion turns to risk. Before traction, they drained checking and savings, then tapped a 401(k) to fund the MVP, embracing sacrifice and belief.
They describe complementary roles: Tye as visionary and industry expert; Courtney as operator with enterprise marketing process discipline. The conversation moves to Buffalo and 43North. Relocating for the accelerator, they knocked on doors with the team, signing up shops through community-first outreach and proving traction with efforts that “do not scale.” They highlight expansion to emerging cities and the universality of hair, skin, and nail services.
A recent personal challenge follows: climbing Mount Kilimanjaro with a local banking partner connection. The seven-day trek tested endurance and partnership; “pole pole” slow-and-steady progress mirrored startup life. Returning inspired, they created the “Happiness Journal” to share habits like daily priorities and gratitude. Looking ahead, they mention ringing the New York Stock Exchange closing bell and invite listeners to help by telling every stylist, barber, esthetician, or owner about ShearShare and downloading the app. The hosts close with subscription and contact reminders.
00:00 Welcome and guest intro; ShearShare elevator pitch and mission
01:15 What ShearShare solves for owners and licensed pros; how it works
02:35 Founder journey and funding realities for Black women founders; married cofounders stigma
04:30 Why marriage is a startup advantage; trust and role clarity
05:40 Origin story in 2012: idle suites, first day-rental, word-of-mouth demand
07:20 Decision to build the app; early search for comps and gap in market
08:25 “Mentored by Failure” book and five-point framework
10:10 Funding the MVP: draining accounts, tapping a 401(k); strengthening the risk muscle
12:05 Corporate-to-startup transition; complementary strengths across product, marketing, and operations
13:30 Moving to Buffalo for 43North; why relocate and what changed
15:00 Grassroots growth: door-to-door outreach with community support
16:40 Replicating the playbook in emerging cities; why beauty services are everywhere
18:05 Kilimanjaro invitation and preparation; embracing discomfort
19:20 Seven-day climb lessons; “pole pole,” optimism, and partnership under pressure
21:10 The Happiness Journal concept and daily practices
22:20 What is next for ShearShare; momentum and milestones including NYSE bell
23:30 How listeners can help: tell a stylist or owner; download the app
24:40 Final thoughts on optimism as a competitive advantage
25:30 Host wrap and subscribe details
Courtney Caldwell joins Nancy Fechnay to share ShearShare’s origin story, COVID pivots, culture lessons, and insights on mental health, fundraising, and cofounding as a married couple.
The session opens with introductions by moderator Nancy Fechnay, an independent angel investor and advisor, who highlights Courtney Caldwell’s career trajectory from global tech leadership roles to cofounding ShearShare. Fun facts follow: Courtney reveals her upbringing as a military brat and her passion for vegan baking. She recalls how a college crush led her into an entrepreneurship class, though her husband, Dr. Tye Caldwell, modeled risk-taking long before ShearShare’s creation.
Courtney introduces ShearShare as the first B2B mobile app that lets licensed stylists rent professional space by the day, giving owners new revenue streams while empowering independent workers with flexibility. She explains how the idea originated in 2012 from filling empty chairs in her husband’s salon, eventually becoming a full-time business after repeated requests.
The conversation turns to COVID-19’s impact. With salons shuttered, ShearShare pivoted to supporting its community by creating over 100 resources, helping 125+ stylists access PPP loans, and launching a virtual beauty supply store. She emphasizes team well-being through daily standups, one-on-one check-ins, and a “brain vacation credit” to encourage hobbies and stress relief.
On the future of work, she notes that stylists are reimagining their schedules, seeking three- or four-day workweeks, staying closer to home, and avoiding long-term leases. Courtney underscores ShearShare’s role in keeping small businesses alive, framing barbershops and salons as cultural cornerstones in every community.
She discusses cofounding with her husband, countering investor bias against married founders by highlighting deep trust, role clarity, and complementary strengths. She shares her “Silver Rule”: always leave people, places, and things better than you found them—a principle woven into ShearShare’s hiring, culture, and customer care.
On mental health, she outlines five pillars for founders and teams: eat well, hydrate, sleep, socialize, and move daily. She urges rejecting “martyr” founder culture in favor of sustainable wellness. She then shares ShearShare’s acceptance into the inaugural Google for Startups Black Founders Accelerator, closing a seed round with Lightspeed Venture Partners, and expanding product features.
The session ends with rapid-fire personal favorites (Bible, Your First Million podcast, and vegan Butterfinger bars), a call to download ShearShare, and encouragement for entrepreneurs to “feed what you want to live and starve what you want to die.”
00:00 Moderator intro; Courtney Caldwell bio and career highlights
04:00 Fun facts; entrepreneurship origin story via crush; husband’s influence
08:30 What ShearShare is; “Hairbnb” model explained
13:15 How the idea started with empty salon suites in 2012
17:40 COVID’s impact; pivot to business resources and PPP assistance
22:50 Launching virtual beauty supply store; remote team management and brain vacation credit
28:10 Stylists reimagining work post-COVID; demand for flexible, local, on-demand space
34:00 Building community over competition in beauty industry
38:20 Married cofounder stigma vs. advantage; trust and complementary roles
44:00 Mental health focus; five daily wellness pillars
49:00 Hardest founder challenge: not being technical cofounders; resisting “martyr” culture
52:40 The “Silver Rule”: leave people and places better than you found them
56:20 Fundraising updates; Google Black Founders Accelerator; Lightspeed investment
59:00 Quickfire favorites: book, podcast, quote, and treat
1:02:00 Final thoughts; call to download ShearShare; wrap-up by moderator
Courtney Caldwell pitches ShearShare at Google Demo Day, unveiling how the platform solves wasted salon space, empowers independent stylists, and secures global growth with L’Oréal and major accelerators.
Courtney Caldwell takes the stage at Google Demo Day, introducing herself as cofounder and CEO of ShearShare, alongside her husband Dr. Tye Caldwell. She begins with the problem: 40% of salon and barbershop space goes unused daily. Drawing on her own experience as a salon owner, she explains that stylists increasingly prefer flexible, short-term rentals instead of long leases. In response, ShearShare was created as the first B2B mobile marketplace where beauty professionals book licensed workspace by the day.
Courtney demonstrates how the platform works: users enter a city, select dates, choose workspace type and amenities, then pay seamlessly through the app—like booking a hotel room. She emphasizes that ShearShare supports all specialties—hair stylists, barbers, nail techs, estheticians, makeup artists, and massage therapists. By 2017, ShearShare had listings in 375 cities across 11 countries and secured a pilot with L’Oréal.
She highlights industry shifts: 70% of stylists are now independent contractors, building personal brands on social media while still relying on salons for their craft. ShearShare, she asserts, is positioned to do for beauty what Uber and Lyft did for transportation. Since beta launch in 2016, the platform has grown 20% month-over-month, with 68% of professionals rebooking. With salon space waste estimated at $16.9B annually, she projects $700M+ in three-year revenue potential through a 25% commission model.
Courtney introduces the founding team: Dr. Tye Caldwell, 25-year industry veteran and bestselling author; Courtney herself, with 20 years in enterprise tech marketing at Oracle; and their head of product, an engineer with multiple startup exits. Backed by Y Combinator Fellowship and 500 Startups, ShearShare is positioned to lead the beauty-tech marketplace revolution.
During Q&A, Dr. Tye expands on the L’Oréal partnership and how ShearShare will expand from space rental into broader ecosystem services like insurance, retail, and product distribution. They discuss marketplace dynamics, emphasizing data-driven city expansion and network effects. Dr. Tye also underscores stylist demand: most users are experienced female stylists who travel locally and regionally, building clientele across cities while retaining customer relationships.
The judges commend ShearShare’s traction, market clarity, and founder experience. Later in the session, ShearShare is announced as one of two winners, securing $250,000 from Steve Case’s Rise of the Rest fund.
00:00 Introduction and applause for Courtney Caldwell, ShearShare CEO
00:40 Problem: 40% of salon/barbershop space unused daily
01:10 Origin story: from salon expansion in 2012 to solving stylist demand manually
02:05 Platform explained: search, filter, amenities, book space like a hotel
03:20 Expanded services: all cosmetology specialties supported
04:00 Growth stats: 375 cities, 11 countries, L’Oréal pilot announced
05:15 Industry trends: rise of independent stylists, brand-building on Instagram/YouTube
06:00 Market opportunity: $16.9B wasted annually; ShearShare’s commission model
06:40 Founding team bios: Dr. Tye, Courtney, and head of product
07:30 Growth metrics: 20% MoM, 68% rebooking rate
08:20 Q&A: L’Oréal partnership vision; beyond space rental to ecosystem services
09:30 Q&A: Marketplace network effects and city expansion strategy
10:30 Q&A: Stylist demographics, demand for travel-friendly, flexible work
12:00 Transition to next pitch segment
Later: Winners announced; ShearShare awarded $250K from Rise of the Rest
Entrepreneurship, future of work, leadership, beauty-tech, digital marketing, and diversity in technology.
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