Surviving The River And Building The Bridge
"If you can look at challenges as opportunities, the whole world is your oyster."
Wiley Cerilli is a serial entrepreneur and founder of companies like Seamless Web, SinglePlatform, and Good Uncle. He was previously the VP and General Manager of Constant Contact after they acquired his company SinglePlatform for $100 million. Throughout his career, Cerilli has experienced immense personal and professional growth, including overcoming the tragic loss of his father at a young age.
The interview covers Cerilli's inspirational journey, from losing his father while in high school and becoming "CEO" of his family, to the lessons he learned from successful exits at Seamless Web and SinglePlatform. He provides tactical advice for entrepreneurs on topics like fundraising, hiring, sales, product development, and maintaining work-life balance through difficult times. Cerilli stresses the importance of community and resilience when dealing with trauma and chaos. He shares vulnerable stories and actionable frameworks like "Test, Tune, Scale" that provide invaluable insights for young founders. This emotional yet practical interview exemplifies how entrepreneurs can draw strength from hardship, build empathy and vision, and manifest success through perseverance.
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Surviving The River And Building The Bridge
The Parable of the Bridge Builder
There once was an old man who, after crossing a treacherous river that nearly took his life, decided to construct a bridge for those following behind.
A passerby questioned his work, pointing out that the builder had already overcome the challenge of the river, and won't need to cross it again. The old man replied that others would be crossing this river, and they may not have the fortune that he had in making the crossing. He stated that he was building a bridge for them, using the knowledge and experience he gained on his own journey.
This parable serves as a metaphorical canvas for Wiley Cerilli’s life. The "river" symbolizes the trauma and hardships we face in our lives, and Wiley's own river was fraught with personal challenges, survival, success, and finding the resolve to build bridges for others.
Falling into the River: The Day Wiley Became the CEO of His Family
When Wiley was just 16 years old, he lost his father to cancer. He had become the “CEO of his family,” and realized that their household was facing financial ruin. Wiley was forced to grow up fast while providing for his grieving family, helping his mother through mental and physical sickness, and building a life for himself worthy of his father’s dying words. He had to decide how this torrent of trauma and hardship would shape his life.
As a teenager, Wiley faced trials and tribulations far beyond his years. Between the electricity getting shut off and not having enough money for food for his family, Wiley dropped out of school to work tirelessly to pay the bills and provide stability for his family. During this time, Wiley's mother struggled intensely with depression and suicide attempts in the wake of her husband's death. Wiley recalls this period as overwhelmingly chaotic and lonely - all while experiencing the traumatic grief of this father’s passing. He vividly describes the feeling of being plucked from his friends and stuck behind an invisible barrier - a “fishbowl” where the outside world was looking in on him, but not truly understanding what he was going through.
As each bridge builder helps those who come after them, Wiley found a mentor who helped him rebuild his life during this difficult time. The founder of Meetup, who also lost his mother at a young age, took Wiley under his wing. He instilled in Wiley the belief that he could overcome anything by focusing on his natural talents as a visionary storyteller and convener of people. Wiley soon discovered a community of individuals and entrepreneurs who had also lost parents, and he grew quickly with the support of his new family. These mentors, friends, and well-wishers taught Wiley valuable life lessons; they showed him that trauma can either define or refine us, and that the choice is ours to make in the end. For Wiley, it became a refining fire, molding him into a resilient, empathetic, and driven individual. Armed with newfound confidence, Wiley embarked on an incredible entrepreneurial journey spanning over two decades.
Taking His First Steps at Seamless
In the late 1990s, online food ordering was still a novel concept in a world where most people were comfortable ordering food online. The Seamless team was ahead of their time, providing bespoke services to Law Firms and Investment Bankers working late on the job. Wiley recounts joining this dynamic team, admitting that the process was "not very seamless" but an exciting team to work with. Cerilli and his co-founders started by manually taking orders, faxing them to restaurants, and even hand-delivering the meals themselves. However, they rapidly adapted and improved the technology, building one of the first automated online ordering systems. Seamless was pioneering online food delivery years before it became mainstream.
As Seamless grew, Cerilli faced challenges scaling the business from a small startup to a large company serving hundreds of corporate clients. He focused on identifying strong leaders and creating a culture of urgency to drive rapid expansion. Under his leadership as CEO, Seamless became the largest online food ordering service, processing millions in orders annually. After over a decade of hypergrowth, Seamless was acquired by Aramark in 2012 for around $100 million.
The acquisition was an emotional moment for Cerilli after years of stress and hard work growing the company. Cerilli stayed at Seamless for a few more years post-acquisition to maximize earnout payments. He helped grow Seamless from a scrappy startup into a hugely successful business, cementing its place as a pioneer of online food delivery and benefiting from the massive rise of the industry in subsequent years.
Crossing The River and Finding Success
After Seamless, Wiley Cerilli's next big idea was SinglePlatform - a service to help businesses manage their online presence and listings. In the early 2010s, many local restaurants, salons, and other businesses had no centralized way to update their information across review sites, search engines, and directories. Cerilli saw an opportunity to aggregate these listings and become the single platform enabling businesses to sync their menus, prices, and other data.
When Wiley first started trying to sell the Seamless online food ordering service to restaurants, he faced constant rejection and refusals from owners - “People just don’t like being sold to,” he recounted in his interview. He realized he needed to “flip” the traditional sales script to get business owners to buy into the platform. His ingenious approach was to approach the conversation as a representative of sites like TripAdvisor, saying that Seamless was looking to feature select restaurants on the platform. He would set up the sales call like an interview, asking owners about their awards, delivery zones, and capacity to handle more orders. Flipping the script made the owners eager to prove why their restaurant deserved the spotlight. They essentially started selling themselves on why Seamless should feature them. Wiley leveraged the influence of trusted brands to flip the script and get owners actively persuading him to put them on the platform. The strategy was highly effective - it exemplified Wiley's sales creativity and understanding of human psychology to rapidly grow his business.
Just two years after founding SinglePlatform, Cerilli sold the company to Constant Contact in 2011 for around $100 million. He described the moment when the wire hit as a breath of oxygen after struggling financially in the early startup days. Cerilli stayed for several years with Constant Contact and grew SinglePlatform into a leading local listings management platform. Overall, he proved his ability to repeatedly identify promising startup ideas and execute the strategy to quickly scale and extract value from the business.
In 2012, Wiley saw an opportunity to bring cult favorite restaurants to underserved college campuses nationwide. He launched Good Uncle, delivering local favorites like Sweetgreen and Joe's Pizza to students via ghost kitchens. Though still early, Wiley ended up selling Good Uncle to Aramark to provide stability for his team.
In Wiley's latest venture, House Accounts, he aims to consolidate and digitize the fragmented home services industry. After closing a $20 million Series A this year, House Accounts is already partnering with massive home service providers to improve booking and payments for millions of homeowners.
Building The Bridge For Those Who Come After
Throughout his entrepreneurial journey, Wiley has overcome numerous pitfalls and crises that threatened to pull him under. Time and time again, he managed to find the inner strength to survive and thrive.
Much of this resilience stems from Wiley's experience early in life with loss and hardship. While devastating to live through, the chaos and uncertainty forced Wiley to develop critical skills like blocking out noise, identifying opportunities, and moving forward no matter what.
Wiley also learned the importance of slowing down, putting problems in perspective, and making decisions with a steady mind. His ability to remain calm under pressure has been invaluable in high-stress environments like the startup world.
Once Wiley achieved entrepreneurial success, he looked back at the "rushing river" he barely crossed and made it his mission to build bridges for those following behind him.
This bridge has manifested in many incredible ways, the most profound being Experience Camps, a nonprofit that provides free summer camps for children who have lost a parent, sibling, or primary caregiver. After losing his dad, Wiley recognized first-hand the pain and isolation these children experience, and he has created an experience where that isolation is replaced with real empathy and love from others who understand your journey.
Experience Camps offers a fun, supportive community where kids can just be kids - rather than being defined by their loss. With 10 camps across America and thousands of campers, this organization has made a real impact in the lives of youth affected by grief and trauma. Wiley remains deeply involved as a camp counselor and Board Member.
By supporting the next generation, men and women like Wiley ensure that those confronted by the "rushing river" have a bridge to cross it safely. Though nothing can erase the pain of losing a loved one, the compassion of others can provide the nurturing foundation to not only survive, but thrive. Wiley's story offers an inspiring reminder that our greatest purpose comes from serving those following behind us. No matter how battered we may feel, we each have the power to transform our wounds into wisdom - and build bridges that guide others through the darkness.
