Windsor Greetings - Chapter 9: Moving Forward
Following Uncle Tom's funeral, Alex and Tyler chart a path forward—together.
Hey, Friends! We’re almost at the end. Just one chapter remains after this one. Thank you so much for reading. I can’t wait to hear what you think about how this ends.
In the meantime, please enjoy the second to last chapter in the saga of the Windsor family and their greeting card empire.
Previously On Windsor Greetings
In the wake of Uncle Tom’s death, rising tensions and power struggles within the Windsor family come to a head when Jan—armed with both moral authority and newly inherited shares—calls a decisive meeting and declares that Alex and Tyler must set aside their rivalry and work together to save the family business.
Table of Contents
Chapter 9: Moving Forward
Chapter 9: Moving Forward
Uncle Tom’s funeral was a beautiful occasion. The extended Windsor family gathered from far and wide to pay their respects. Hundreds of family friends and current and former Windsor employees attended the service, filling the church to capacity. The church had to open both balconies to accommodate the crowd—a testament to the mark Uncle Tom left on his community and family. It was a day of sorrow for the family, but also one of deep gratitude for a life well-lived.
Henry’s eulogy captured the essence of Tom’s legacy. He recounted the humble beginnings of Windsor Greetings. As young men, Tom, Henry, and Ronald had started as house painters. It was difficult work—long hours under the sun, aching bodies, and the ever-present danger of scaling ladders. Yet even in those early days, the brothers stood out. After completing each job, they sent their clients thoughtful, handmade thank-you cards. Henry described these cards as the secret touch that kept their calendar full, proof of the power of sincerity and a personal touch.
Eventually, the brothers realized they were in the wrong business. Painting houses paid the bills, but it was hard work, lacked creativity, and they’d pretty much reached the ceiling of its earning potential. With some hesitation, they sold the company and took a leap of faith. For Ronald, a new father at the time, the decision was particularly challenging—walking away from a steady income was no small thing. But Tom’s infectious optimism had a way of quieting doubts. He saw a future others couldn’t imagine, a scalable business built on the heartfelt connections their cards inspired. And so, with a shared belief in the Windsor name, the three brothers forged ahead, turning a small act of gratitude into an enduring family legacy.
As Alex listened to his father recount the story of Windsor Greetings’ earliest days, something deep inside him stirred. His mother had been right. The only way forward was together. As his gaze swept across the room, it landed on Tyler. Their eyes met, and in that moment, Alex saw the same realization reflected back at him. For all their differences, they both knew that the future of Windsor rested in unity.
Following the service, Jan and Henry hosted a luncheon at their home. Here, Tyler and Alex excused themselves to their father’s study to consider the future of Windsor Greetings. Both had spent countless hours crafting plans to safeguard their parents’ retirement, yet neither had paused to entertain the possibility that the other’s ideas might hold any value.
Through their conversation, Alex admitted to Tyler that the deal he’d procured was impressive. It would solve the money problem once and for all, but they both agreed it would come at the cost of the family’s legacy. Tyler, too, admitted that if Alex were to obtain complete control of the business, he’d likely drive efficiencies by introducing new technology and make them profitable again, but it would mean ruthless cuts to the employee base and hard decisions that would alienate him from his family.
It became clear to both Alex and Tyler that they needed a new plan—one that ensured their parents wouldn’t spend their remaining years in squalor, and one that would preserve the family legacy. Never being much of an ideas guy, that meant it was up to Alex to come up with something, and so he put his head down and thought.
After several moments of silence, Tyler spoke up, “Can you believe dad and uncle Ron and Tom just threw away their painting business, and started over?”
Alex looked up. “What do you mean?”
“They had this great business, and they just threw it away to start something new,” Tyler replied.
Alex’s eyes went wide. “That’s it!” Alex said.
“That’s what?” Tyler replied.
“That’s what we need to do, Tyler. We need to start something new as well. We need to bet on ourselves like the previous generation of Windsors did. We need to lean into our strengths and reinvent the business.”
“Doing what?” Tyler asked.
“Do you think there’s room to renegotiate the deal you struck? What if we restructured it from an all-out sale to an exclusive licensing deal?” Alex asked.
“They might go for something like that,” Tyler replied, “but it won’t solve all our money troubles. There’s no way they’ll pay anywhere near what they offered just to license our IP.”
“I figured as much, but it might be enough to set mom and dad up and give us the runway we need to pivot into something new,” Alex replied.
“True,” Tyler said, “but what new thing are you talking about?”
“Our building no longer serves us. It’s at half capacity as is, and if we’re not making paper cards anymore, we definitely don’t need most of the space,” Alex said.
“You want to sell the building?” Tyler asked.
“No,” Alex replied, "I want to turn it into a coworking space. It’ll produce steady, predictable income from various tenants and breathe new life into the Windsor name.”
“What about all of our employees?” Tyler asked.
“This isn’t going to be easy, but nearly half of them are of retirement age. We’ll have to push them there, cut our weakest employees, and move forward with only our most hardcore staff who want to join us on our next adventure.” Alex said with inspiration in his voice.
“Hard-core landlords’ assistants?” Tyler asked.
“No, Tyler.” The coworking space is only part of the plan. As part of the restructured deal, I’d like to retain digital rights to the Windsor name.”
Tyler looked confused, “We make paper greetings cards, Alex. What digital rights?”
Feeling more inspired than ever, Alex reminded Tyler what their father always loved to say: “A greeting card is a cherished keepsake, a vessel for meaning and love.” Alex continued, “There’s no reason that vessel has to be paper. The greeting card space hasn’t evolved one bit since Windsor Greetings’s founding, but the rest of the world has. We need to reimagine the greeting card for the mobile generation.”
Alex’s vision started to crystallize in Tyler’s mind, and for the first time in his life, he allowed himself to believe in his younger brother. “If you think this is the path forward, I’ll work like hell to make it happen.”
When the boys emerged from Henry’s study, they found a moment of quiet to share their new plan with their parents. Jan had clearly used her powers of persuasion on Henry to shift his viewpoint on the succession matter. He looked both boys in the eye, kissed them on the forehead, and said, “The business is yours now. We trust that you’ll figure it out.”
Stay Tuned
Want to see what happens next? Check back every Tuesday — and don’t miss my weekly creative roundup on Friday.
Until then,
-Mike