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.

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.

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.