Exit-Ed: Stories From Grind to Sale

Gabriela Smith
  • 5.0 (10)
  • ENTREPRENEURSHIP

Exit-Ed: Stories from Grind to Sale Join us on Exit-Ed, the podcast where successful founders share the untold stories behind building, scaling, and selling their companies. In each dynamic episode, we go beyond the headlines to explore the challenges, strategies, and pivotal moments that shaped the journeys of entrepreneurs from each corner of the globe. From the long nights spent grinding to the high-stakes negotiations that led to rewarding exits, our guests provide practical insights, hard-won lessons, and inspiration for anyone on the path to success. Whether you're an entrepreneur preparing for a sale, an investor looking to understand founder dynamics, or a business leader seeking new growth strategies, this podcast is for you. Learn from those who've been there. Get Exit-Ed.

Episodes

  1. 12/15/2025

    Ep. 9 The Art of the Pivot: Lessons from an AI Entrepreneur (feat. Joseph Hanna)

    In this episode of Exit-Ed: Stories from Grind to Sale, Gabriela Smith interviews Joseph Hanna, a seasoned technology executive, founder, and author whose career spans from software engineering in the 1990s to building and exiting an AI-driven HR analytics company. Born and raised in Alexandria, Egypt, Joseph began his career at Oracle before moving to the U.S. in his mid-20s. After years in leadership roles with Fortune 500 and private equity–backed companies, he launched Engage in 2014, an AI predictive analytics platform focused on talent acquisition. Engage grew rapidly, raised $12 million in venture funding, and was acquired by a Carlisle-backed company in 2019—just before the pandemic. Joseph shares insights on building a company later in life and why experience, networks, and judgment can outweigh youth in today’s startup world. He discusses how the venture capital landscape has evolved to favor seasoned founders who can navigate complexity and lead with stability. Reflecting on the differences between corporate and entrepreneurial life, he explains that maturity and preparation allowed him to manage risk and scale successfully. The conversation moves into AI, innovation, and the speed of modern creation. Joseph describes how advancements in tools and automation now let founders build prototypes in weeks instead of months, shifting the bottleneck from engineering to understanding the customer. He argues that success now depends on how fast teams can adapt, gather feedback, and pivot—not just on technical skill. Gabriela and Joseph also explore how AI is reshaping every industry, including law and technology. They discuss the new baseline skill set founders need—coding literacy, product understanding, and the ability to delegate intelligently. Both agree that leaders must now combine hands-on knowledge with strategic perspective to stay competitive. Joseph, author of Pivoting, shares lessons from his journey about innovation, timing, and resilience. He challenges founders to see pivots not as signs of failure but as proof of adaptability and continuous learning. His perspective is clear: in the age of AI, speed and flexibility define entrepreneurial success more than ever.

    57 min

  2. 11/24/2025

    Ep. 8 Seasoned, Not Done: Turning Decades of Experience into a Successful Exit (feat. Tom McKeown)

    In this episode of Exit-Ed: Stories from Grind to Sale, Gabriela Smith interviews Tom McKeown, founder and former CEO of Trend Data. Tom shares how, at age 56, he left a long corporate career to build and sell a successful HR analytics company—proving it’s never too late to become an entrepreneur. Trend Data, founded in 2017, used AI-driven people analytics to help companies identify workforce trends such as turnover and recruiting success. Tom and his co-founder saw an opportunity to serve mid-market clients that lacked affordable analytics tools. The company grew steadily until the pandemic hit, forcing hard choices and stalled funding rounds. Still, Trend Data survived and caught the attention of iSolved, a national HR and payroll firm. What began as a potential partnership turned into an acquisition finalized in June 2021. Tom stayed on for two years to oversee integration and product expansion before stepping away in 2024. Reflecting on the sale, he highlights the importance of organization and discipline: keep documentation ready, align stakeholders early, and resist overreaching earn-outs. Most of all, understand that after the deal closes, the product belongs to the buyer—founders must adapt quickly. Before founding Trend Data, Tom spent decades in software, working with firms like Adobe, Citrix, and WebEx, and leading multiple HR tech exits. He credits his early inspiration to Ross Perot, whose advice to “learn an industry cold” shaped his approach to entrepreneurship. After his exit, Tom published This Is Panther Country: A Memoir of Youth, Underdog Spirit, and Basketball Glory, about his Long Island high school basketball team. He draws parallels between sports and business—pressure, teamwork, and knowing when to pivot. Today, Tom advises several startups in HR and technology and believes AI, like past innovations, will create more opportunities than it eliminates for those willing to adapt. His story is a testament to resilience, reinvention, and the value of experience in building and exiting a company.

    56 min

  3. 11/03/2025

    Ep. 7 Scaling Smart: From Rustic Wedding Chic to Empowering Female Founders (feat. Maggie Lord)

    In this episode of Exit-Ed: Stories from Grind to Sale, Gabriela Smith interviews lifelong entrepreneur Maggie Lord about her journey from childhood ventures to selling Rustic Wedding Chic to David’s Bridal. Maggie shares how her entrepreneurial spirit started early, from selling seashells as a child to turning her love of creativity into a nationally recognized digital brand. Rustic Wedding Chic began in 2008 as a small blog showcasing rustic wedding ideas and grew into a major online media company with ten million monthly Pinterest impressions, book deals, and television appearances—all bootstrapped without outside funding. Maggie explains how authenticity and quick decision-making fueled her success, as well as how she recognized when it was time to sell. Her sale to David’s Bridal in 2020 was driven by strategic alignment—the company reached brides earlier in the buying journey and fit perfectly into David’s long-term goals. After the acquisition, she joined the company as Vice President and later co-founded The Whisper Group with Carrie Kerpen to help women prepare for and execute successful business exits. She discusses common misconceptions about entrepreneurship, emphasizing that success doesn’t require large capital—just creativity, persistence, and humility. Maggie also shares her mindset shift of adding “not yet” to setbacks, turning frustration into progress. Balancing entrepreneurship and motherhood, she describes building a business from her kitchen table while raising three children, underscoring that founders can design a life and career that truly work for them. Maggie believes AI is a valuable tool but insists authenticity and human experience remain irreplaceable. Her advice for aspiring founders is direct: just start. Every step, no matter how small, moves you forward. Her story illustrates how resilience, adaptability, and personal integrity can turn simple ideas into scalable success.

    58 min

  4. 09/01/2025

    Ep. 6 - Nearshore Founder Story: No Loans, No VC—Just 15 Years of Grit (feat. Iago Rodriguez)

    In this global edition of Exit-Ed, host Gabriela Smith sits down with Iago Rodríguez, a technical founder whose quiet persistence helped grow a boutique software development company into a 300-person multinational operation—and ultimately led to a strategic exit. Originally from Spain and based in Argentina, Iago shares the winding, 15-year journey that began with four freelancers and culminated in the sale of their company to a U.S.-based firm. Iago opens up about everything from near-burnout years to their unconventional merger with another small team, which doubled their capabilities—and their risks. Together, they built a thriving cross-border outsourcing firm, driven not by flashy sales tactics but by one core value: trust. This episode is packed with real talk on client service, international growth, and the role of humility in leadership. Iago explains how trust—not just tech—is the true business model, and why founders must be willing to serve both clients and team with relentless consistency. We explore the emotional layers of selling a business you didn’t even set out to build, the mental shift required to think in terms of “EBITDA” after years of bootstrapping, and the cultural empathy needed to win U.S. clients from halfway around the world. Iago also shares powerful insights on remote leadership, including his metaphor of founders as the “sweepers” clearing the path for their team to shine. If you're a service-based founder, international operator, or just someone wondering how small teams make big exits, this episode is a case study in quiet excellence, operational resilience, and leading with heart. For more about Iago: https://www.linkedin.com/in/iagorodriguez/ If you enjoy this episode, please consider leaving a five-star rating and sharing it with a founder in your network.Connect with Exit-Ed:Tiktok: https://www.tiktok.com/@exitedstories LinkedIn: https://www.linkedin.com/company/exit-ed/

    58 min

  5. 08/11/2025

    Ep. 5 - Legal Battles and Cocktails: THIS Founder is Raising the (Can!) (feat. Tatiana Chamorro)

    In this energizing and honest episode of Exit-Ed, host Gabriela Smith speaks with Nicaraguan-born founder and Dallas-based entrepreneur Tatiana Chamorro. Tatiana opens up about her evolution from college student and young mom to serial founder, franchise builder, and now Chief Marketing Officer of an innovative cocktail startup. Her journey is packed with sharp business insight, heartfelt lessons, and deeply personal reflections. Tatiana walks us through her early entrepreneurial roots—selling unbreakable cookies with a friend as a child—and how that creative, problem-solving spirit shaped her path. She shares how she bootstrapped her education in the U.S. as an international student, hustled to build a marketing agency with recurring revenue, and joined forces on an ambitious digital franchise model that scaled fast across the U.S. But success wasn’t without conflict. Tatiana candidly details the emotional and legal complexities of exiting a business that once defined her. From co-founding a multi-million dollar operation to navigating a difficult merger and ownership dispute, she unpacks the realities many founders face but rarely discuss: burnout, misaligned values, legal battles, and the identity crisis that follows an exit. Now, she’s found renewed purpose as a partner and CMO at Toucan Cocktails, an award-winning ready-to-mix beverage brand that’s disrupting the alcohol industry with patented packaging technology. Tatiana shares how she leveraged lessons from her past to build better foundations this time—clear values, strong boundaries, integrated systems, and healthy partnerships. This episode is for anyone—especially women and immigrant founders—who’s juggling business, family, self-doubt, and ambition. Tatiana’s story proves that reinvention is not only possible, it’s powerful. Whether you’re building your first startup or bouncing back from burnout, this conversation will inspire you to own your narrative, learn from the hard moments, and dream boldly. For more about Tatiana: Instagram: https://www.instagram.com/tatianachamorro/ LinkedIn: https://www.linkedin.com/in/tatianachamorro/Fore more about Toucan Cocktails: Website: https://toucancocktails.com/  Instagram: https://www.instagram.com/toucancocktails/ If you enjoy this episode, please consider leaving a five-star rating and sharing it with a founder in your network.Connect with Exit-Ed:Tiktok: https://www.tiktok.com/@exitedstories LinkedIn: https://www.linkedin.com/company/exit-ed/

    53 min

  6. 07/21/2025

    Ep. 4 - Faith, Finance, Growth, and REAL Life (feat. Skip Johnson)

    In this deeply candid episode of Exit-Ed, host Gabriela Smith sits down with entrepreneur Skip Johnson for a raw, reflective, and highly practical conversation about what it really takes to scale a business—and then let it go. Skip, a former architect turned financial services founder, shares the winding path that led him from small-town Minnesota to co-founding a retirement planning firm that scaled from a team of two to over 70, earning accolades like the Inc. 5000 and Minnesota Fast 50. With clarity and humility, Skip walks us through the defining moments of his entrepreneurial journey: discovering a passion for client-centric systems, navigating betrayal in his early career, rebuilding with integrity, and ultimately exiting his business not to a PE giant, but to internal partners. The conversation dives into critical lessons for founders: why identifying your personal “why” matters more than loving your product, how to set client boundaries while building trust, and why entrepreneurs must consistently reassess their businesses—and themselves. Skip shares the pivotal moment a key employee left, forcing him to shift from running an advisory “practice” to building a scalable, systemized company. We also explore the emotional terrain of exiting: the identity crisis that often follows, how to handle fractured partnerships, and why selling your business is more like a personal reinvention than a financial event.  Now the founder of Tailwinds and River Bend Refuge, Skip supports other business owners as they hit the scaling wall and helps guide them toward healthy growth—personally and professionally. Whether you’re still in the trenches or thinking about the next chapter, this episode is a masterclass in perseverance, boundaries, and intentional leadership. Tune in to hear how faith, failure, systems, and therapy all played a role in building—and exiting—a business with purpose. For more about Skip:  https://www.linkedin.com/in/skipgjohnson/  Tailwinds Group: https://www.tailwinds-group.com/  Gratus Funds: https://www.gratusfunds.com/                           If you enjoy this episode, please consider leaving a five-star rating and sharing it with a founder in your network.Connect with Exit-Ed:Tiktok: https://www.tiktok.com/@exitedstories LinkedIn: https://www.linkedin.com/company/exit-ed/

    53 min

  7. 06/30/2025

    Ep. 3 - Charisma, Grit & the Grind (feat. Andy Smith)

    In this episode of Exited: Stories from Grind to Sale, host Gabriela Smith welcomes Atlanta-based entrepreneur Andy Smith to explore the candid highs and lows of building, scaling, and exiting businesses. Andy opens up about his transition from the corporate world to entrepreneurship, driven by a sense of frustration and confinement in traditional roles. In 2007, he co-founded his first company with a partner from the Netherlands, launching an innovative clean energy venture aimed at replacing their salaries—not chasing millions. Their complementary skills—Andy's strength in business development and his partner's technical prowess—fueled their early momentum. Despite early legal challenges and a high-stakes lawsuit from a former employer, their grit and creativity led to international deals and eventual scale. Andy reflects on the vital role of trust, humility, and emotional intelligence in both business and partnerships. He emphasizes that paperwork can’t replace human character, and a truly good business partner is irreplaceable. The conversation dives deep into topics like charisma, empathy, and the immigrant mindset—qualities Andy sees as foundational to successful entrepreneurship. Gabby and Andy also share personal stories about resilience, the emotional toll of lawsuits, and the importance of intentional pauses after an exit. The episode culminates in a discussion about the impact of exits—not just financially but on community and legacy. Andy shares that while his first exit brought financial transformation, it was the recognition from employees and their families that brought the most profound fulfillment. Now the founder of Blacksmith Ventures, Andy focuses on empowering other founders, especially those with deep technical expertise, to scale their ventures and prepare for exits. He shares lessons learned from both successful exits and a few hard-earned failures, stressing the importance of being "exit ready" from day one. This episode is a masterclass in building with purpose, adapting through adversity, and leveraging business as a force for personal and communal impact. For more about Andy: https://www.linkedin.com/in/andysmithlife/ If you enjoy this episode, please consider leaving a five-star rating and sharing it with a founder in your network. Connect with Exit-Ed:Tiktok: https://www.tiktok.com/@exitedstories LinkedIn: https://www.linkedin.com/company/exit-ed/

    1 hr

  8. 06/09/2025

    Ep. 2 - Disrupting ‘I Do’ (feat. Ashley Hawks)

    Episode 2:  Disrupting ‘I Do’: How This Exit-Ed Founder Revolutionized the Wedding Industry Hosted by Gabriela Smith In this episode of Exit-Ed, Gabriela Smith sits down with visionary founder Ashley Hawks to discuss her remarkable journey from helping out in her mother’s bridal shop to co-founding, scaling, and ultimately exiting Forever Bride, a company that revolutionized the wedding industry. Ashley shares how growing up surrounded by tulle and tradition gave her insight into the emotional core of bridal retail—and how she used that foundation to spot a major gap in the market. Ashley walks listeners through how she transformed a local family business background into a nationwide platform that helped wedding vendors thrive through storytelling, community, and technology. With a heavy focus on service, relationship-building, and bold experimentation, Ashley and her partners created a brand that offered something national platforms couldn’t: local connection and authenticity. She opens up about the hard lessons of entrepreneurship, including why selling well matters more than selling fast, how to recognize when partnerships are healthy, and the importance of building a business that’s ready to scale and sell from day one. Ashley also speaks candidly about the personal challenges that come with motherhood, leadership, and letting go of the “baby” she built. Now the founder of SOAR, a peer group platform for CEOs and entrepreneurs, Ashley shares how the power of mentorship, community, and emotional intelligence helped her grow not just a company, but herself. One of the most striking moments in the episode comes when Ashley reflects on her journey: “You’re putting your name and your reputation and your money and your entire livelihood out on the line, and you're creating something out of nothing and expecting it to provide for your family—that’s risky, yes. But almost every time I took a risk, it paid off in some way, shape, or form.” Gabriela and Ashley also explore what it means to build a business with purpose, how to lead without losing your sense of self, and why personal legacy matters just as much as professional success. If you’re a founder navigating early growth, wondering what an exit could look like, or simply searching for an honest conversation about the ups and downs of entrepreneurship, this episode offers inspiration, practical insight, and wisdom hard-earned from years in the trenches. Listeners can also hear Ashley’s take on common founder traps, like over-planning before selling anything, the loneliness of leadership, and how to stay grounded when the spotlight fades. For more about Ashley: https://www.linkedin.com/in/ashley-hawks-590bb753/ If you enjoy this episode, please consider leaving a five-star rating and sharing it with a founder in your network. Connect with Exit-Ed:Tiktok: https://www.tiktok.com/@exitedstories LinkedIn: https://www.linkedin.com/company/exit-ed/

    1h 9m

  9. 05/19/2025

    Ep. 1 - Not Just Unicorns

    In this debut episode of Exit-Ed, host Gabriela Smith lays the foundation for a bold new podcast that dives deep into the untold stories of everyday entrepreneurs who’ve built, scaled, and exited real businesses—without the flash and fame. Gaby, an attorney-turned-founder, shares her perspective from almost two decades of experience working with entrepreneurs from inception to exit. From multi-million-dollar acquisitions to navigating lawsuits, family tensions, and burnout, she’s seen it all. And now, she’s handing the mic to the founders behind the scenes of the global economy. This is a show about the builders who made something from nothing. Connect with Exit-Ed:Tiktok: https://www.tiktok.com/@exitedstories LinkedIn: https://www.linkedin.com/company/exit-ed/

    9 min

  10. 05/12/2025

    Exit-Ed: Behind the Curtain of Exits

    In the trailer for Exit-ed, host Gabriela Smith introduces a podcast dedicated to shining a light on the untold, real stories of entrepreneurs who have built and sold their companies—without making the national headlines. Drawing on her dual identity as a lawyer and entrepreneur, Gabriela shares her perspective on how entrepreneurial journeys are rarely linear, often underrepresented, and vastly more diverse than the high-profile unicorn exits featured in the media. The podcast will explore the gritty, authentic paths of founders—from ideation to scaling, connecting, and ultimately exiting their businesses. It promises insider conversations that dive into the heart of entrepreneurship, discussing the risks, challenges, strategies, and pivotal moments behind successful exits. The show aims to inspire and inform entrepreneurs, investors, and business leaders by going beyond the glossy headlines to reveal the real dynamics of building and selling companies. Connect with Exit-Ed:Tiktok: https://www.tiktok.com/@exitedstories LinkedIn: https://www.linkedin.com/company/exit-ed/

    3 min

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About

Exit-Ed: Stories from Grind to Sale Join us on Exit-Ed, the podcast where successful founders share the untold stories behind building, scaling, and selling their companies. In each dynamic episode, we go beyond the headlines to explore the challenges, strategies, and pivotal moments that shaped the journeys of entrepreneurs from each corner of the globe. From the long nights spent grinding to the high-stakes negotiations that led to rewarding exits, our guests provide practical insights, hard-won lessons, and inspiration for anyone on the path to success. Whether you're an entrepreneur preparing for a sale, an investor looking to understand founder dynamics, or a business leader seeking new growth strategies, this podcast is for you. Learn from those who've been there. Get Exit-Ed.

Information

  • Creator
    Gabriela Smith
  • Years Active
    2K
  • Episodes
    10
  • Rating
    Clean
  • Copyright
    © 2025 Gabriela Smith