Few entrepreneurial journeys weave through America's most iconic brands, rural family businesses, and groundbreaking startups like Corey Smith's path. As a recent guest on Startups with Stu, Smith shared his remarkable transition from Pillsbury's brand manager (where he created Funfetti cake mix, still their #1 seller decades later) to strategically rebuilding Heinz Ketchup's market share through NASCAR partnerships, before walking away from his six-figure Boston career to save his father's struggling pharmacy in rural Idaho. Alongside his wife Cindy, who left Los Angeles behind for Idaho Falls, the Smiths built a thriving healthcare business while Corey eventually became a pivotal angel investor in Southeast Idaho's emerging startup ecosystem.

What makes Smith's perspective so valuable is his unique position at the intersection of corporate America, family business ownership, and angel investing. In this conversation with Stuart Draper, whose education technology company Stukent grew from a $25,000 check from Smith into a platform serving over a million students, we discover what happens when unwavering belief meets entrepreneurial drive. From the hidden tensions of family business transitions to what Smith describes as the brutal reality that, based on his venture capital experience, 87% of investments fail, Smith's journey showcases both the triumphs and scars of building businesses that matter in places where conventional wisdom says it can't be done.

Lesson 1: Corporate Innovation Requires Strategic Positioning

After completing his MBA at BYU, Corey Smith began his career in brand management at Pillsbury, where his innovation played a vital role in the company's product line. His most successful project involved creating Funfetti cake mix, which remains Pillsbury's top-selling cake mix to this day. Despite this major achievement, Smith received minimal financial recognition—just $2,500 in company stock that was quickly sold when the company changed hands. This early lesson in corporate innovation showed him how challenging it could be to monetize entrepreneurial thinking within large organizations.

Smith's career trajectory took him from Pillsbury to H.J. Heinz in Pittsburgh, where he tackled the company's market share challenges in the southeastern United States. Heinz Ketchup dominated markets nationwide with over 50% share everywhere except the Southeast, where competitors Del Monte and Hunts held strong positions. The breakthrough came when Smith championed a sales manager's persistent recommendation to invest in NASCAR sponsorship, which local leadership had initially dismissed. With a $15-20 million investment in NASCAR teams and merchandise, Heinz saw its Southeast market share climb above 50% within just three years, demonstrating that sometimes the most effective solutions come from listening to people on the ground rather than applying conventional corporate strategies.

Lesson 2: Family Comes Before Career Advancement

After his success at Heinz, Smith moved to Ocean Spray, managing their single-serve beverage lines and working closely with Pepsi on joint ventures. His corporate career was flourishing when personal circumstances intervened—his father experienced serious health problems, including a heart attack and prostate cancer. The family tried to sell his father's small pharmacy in Ammon, Idaho, but found no buyers. With his father's health declining and his parents' desire to serve a church mission before it was too late, Smith made the difficult decision to leave his successful career and return to Idaho.

This transition required not just professional sacrifice, but asking his California-raised wife Cindy to relocate from Boston to rural Idaho—a change she approached with remarkable faith and support despite the dramatic lifestyle shift. The salary reduction from a six-figure corporate income to running a small-town pharmacy represented a financial challenge that required significant lifestyle adjustments for the entire family. Rather than pursuing the conventional path of corporate advancement, Smith chose to honor his father's legacy and support his parents' dreams, even at significant personal cost, ultimately opening unexpected doors to business ownership and community impact that shaped the rest of his career.

Lesson 3: Document Everything in Family Business Transitions

Taking over a family business brings unique challenges that extend beyond typical entrepreneurship. When Smith returned to Idaho, he insisted on properly valuing the pharmacy business at twice what his father had offered a previous potential buyer. This decision came from a desire to prevent future family conflicts, recognizing that even in close families, business transitions can create friction. Smith emphasized the importance of documenting everything with proper accounting and legal guidance to create a clear paper trail for all transactions and equity distributions.

As the business evolved, Smith brought in his brother and brother-in-law, gifting them 10% and another percentage of equity, respectively. This created a true family business but later led to disagreements during the eventual exit. Some family members questioned why they received smaller percentages despite working similar hours, highlighting the difference between management responsibilities and ownership risk. These tensions required Smith to explain the distinction between operating a business and assuming the financial risks of ownership. Despite these challenges, the family business provided meaningful opportunities across generations, creating powerful learning experiences and family connections that wouldn't have existed otherwise.

Lesson 4: Be Stingy With Equity, Especially Early On

One of the most valuable lessons Smith shared came from his observation of entrepreneurs giving away too much equity in their early stages. He noted that debt often feels scary to new business owners, making equity seem like an easier alternative since it doesn't require immediate repayment. However, this decision can lead to significant regret once the business succeeds, as founders realize how much of their future earnings they've surrendered. Smith advised entrepreneurs to be "stingy" with equity—a term he embraces despite its negative connotations in other contexts.

The reason is simple: what seems like a small percentage in the early struggling days becomes enormously valuable once the business achieves success. When coaching Stuart Draper on Stukent's formation, Smith specifically encouraged him to carefully protect his equity position even while seeking necessary investment capital. Smith observed that many equity disputes arise when team members who contribute labor but not capital expect equal ownership with those who assumed financial risk. By clearly establishing these expectations early and documenting all equity arrangements professionally, entrepreneurs can avoid painful conflicts while still attracting the talent and resources they need to grow.

Lesson 5: Character Matters More Than Business Models

Smith's transition into angel investing came naturally from his desire to support entrepreneurship in Southeast Idaho. Along with a group of friends, he formed the Idaho Expansion Group, making three investments with the understanding that venture investing typically sees success in only about 13% of cases. That 13% needs to provide returns substantial enough to cover losses from the other 87%. Of their three investments, one was a complete loss when the founder simply gave up, stating the business was "too hard" despite having taken investor capital. Another returned just 27 cents on the dollar when the founder sold at a low valuation to secure personal employment with the acquiring company. Only one—Stukent, founded by Stuart Draper—provided the investors with a solid return.

These experiences highlighted for Smith the paramount importance of founder character and integrity. Smith observed that many entrepreneurs make commitments they later abandon without consequence, making trustworthiness an increasingly rare commodity in the startup world. His investment in Stukent began with monthly breakfast meetings at Perkins restaurant, where he helped Draper refine his business plan for creating digital marketing education materials. After a year and a half of these advisory sessions, Smith sent Draper a $25,000 check with a note suggesting he quit everything else and go all-in on his vision. This investment wasn't just about the business model, but about Draper's passion and integrity—qualities that proved far more valuable than financial projections.

Lesson 6: Building Relationships That Last Beyond Business

After 42 years of marriage, Corey and Cindy Smith shared insights into what makes both personal and business relationships endure. Their partnership demonstrates several key principles that apply equally to entrepreneurial ventures:

1. Complementary contributions - Each partner brings different strengths and takes responsibility for different aspects of the shared journey

2. Freedom to pursue dreams - Supporting each other's aspirations even when they require personal sacrifice

3. Complete trust - Building a foundation of reliability and integrity that withstands challenges

4. Shared purpose - Finding meaning in working toward common goals rather than individual achievements

5. Deep enjoyment of connection - Genuinely preferring each other's company and collaboration

A significant moment in their relationship came when they served a three-year church mission together. After decades of separate daily routines with limited time together, they suddenly found themselves working as companions around the clock. This experience revealed how connection enhanced their lives in ways they hadn't fully appreciated during their busy years of career building and child-rearing. When they returned to normal life and began drifting back into separate routines, they realized their most fulfilling time had been when they were fully connected to a shared purpose. Smith observed that the entrepreneurs who succeed long-term tend to build genuine connections with their partners, employees, and customers, viewing business not merely as transactions but as relationships.

Lesson 7: Love What You Do More Than What You Make

The entrepreneurial journey isn't primarily about business models, funding strategies, or market opportunities—though these matter tremendously. What Corey Smith's path from corporate America to family business to angel investing reveals is that the entrepreneur's most valuable asset is authentic passion for their work. As Smith put it, "If you love what you do, you never work a day of your life." This philosophy guided his decision to continue working in the healthcare field even after selling his ownership stake to the third-largest long-term care company in the world.

Too many entrepreneurs chase money as their primary motivation, following an "abundance mentality" that prioritizes financial returns above all else. Smith observed that this approach rarely produces lasting satisfaction or even the desired financial outcome. In contrast, entrepreneurs who genuinely love their work tend to create value consistently, regardless of market conditions or temporary setbacks. Smith's current role in long-term care pharmacy illustrates this principle perfectly. Despite having sold the majority stake in his business and having the financial freedom to retire, he continues working because he genuinely loves the industry and serving his customers. He described the healthcare field as "a horrible industry" and "a horrible business" where they're "not making very much money at all"—yet followed immediately with "and I love what I do."

Build on What Truly Matters

The seven lessons from Corey Smith's journey offer a roadmap for entrepreneurs navigating their own path from corporate careers to business ownership or investing. His experiences demonstrate that while strategies and opportunities matter, the foundation of lasting success lies in authentic passion, meaningful relationships, and unwavering integrity. These qualities can't be faked or manufactured—they emerge from living in alignment with genuine values.

For aspiring entrepreneurs in Southeast Idaho or anywhere else, Smith's journey offers a powerful reminder to build businesses on a foundation of genuine passion, strong relationships, and unwavering integrity. The business landscape continues evolving—with remote work bringing new talent to previously overlooked regions and creating fresh opportunities for innovation outside traditional hubs. But amid these changes, trustworthiness remains the rarest and most valuable commodity in business.

Are you ready to follow Corey Smith's example? Start by examining your motivations and relationships. Ask yourself whether you're pursuing your business for the right reasons and surrounding yourself with people of genuine integrity. The answers to these questions may ultimately prove more valuable than any business plan or funding strategy in determining your entrepreneurial legacy.

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