Seeds of ideas.
Growth through action.
Bloom by helping others.
–ChatGPT on Doug Lebda
This is by far one of the most difficult posts I have ever had to write…
I have decided to publish a CELEBRATION of the life of Doug Lebda online for all of posterity.
PROLOGUE – THE MOMENT
For the rest of my life, I will vividly remember where I was on Monday, October 13, 2025, when I learned that Doug Lebda had passed away.
I was at lunch with my sister Tara. My phone – placed face-down on the table – started blowing up with notifications. I didn’t check it until Tara stepped away to use the restroom.
The AI-generated preview summaries showed message after message from industry friends and colleagues about “Doug.” For a confusing moment, I wondered how all these work-world folks suddenly knew about Doug Parker from Westminster, Maryland – my friend since elementary school who had passed from a heart attack just a week earlier at age 57.
Then I opened the full message threads…
It wasn’t Doug Parker they were writing about. It was Doug Lebda.
The public announcement had hit the wire – Doug had died the day before – Sunday, October 12, 2025 – in an ATV accident at his family’s new farm in Western North Carolina. He was 55 years old.
He had been alone, exploring the property, scouting where to build a house for his family’s future. The loyal Lebda family dog “Dutch” was with him. When the accident happened, Dutch stayed by his side. It was Dutch’s persistent barking that led the search and rescue team to find Doug at the accident site.
Lebda Family Dog “Dutch” at the Services
I was instantly shocked and deeply grief-stricken.
Doug Lebda was not just the founder and CEO of LendingTree. He was a visionary who transformed how millions of Americans access financial products. He was a leader who provided radical transparency when others would have stayed silent. He was a connector who brought titans together. He was a friend who would text “Really enjoy our friendship” after a perfect day. He was an entrepreneur who, just a few days before his passing, was still texting me about his next big idea.
For over 20-years, I had the privilege of knowing Doug – first as a competitor I admired from afar when I joined Jason Goldsmith to build TheLoanPage.com into a “little LendingTree,” then as a colleague, partner, advisor, and ultimately, one of my dearest friends.
This post is my attempt to capture what Doug meant to me, to our space, and to the countless lives he touched. There is SOOO much more I could add, but these are the words of loving memory I would like to remain online forever.
If you are reading this and have your own memories of Doug, I encourage you to share them by sending them to CelebratingDougLebda@abovo.co, where we will preserve the full celebration of his remarkable life online forever at https://CelebratingDougLebda.abovo.co
I will miss Doug dearly for the rest of my life.
MEMORIAL SERVICE: FOUNDERS HALL, CHARLOTTE
October 19, 2025. Founders Hall in Charlotte couldn’t hold everyone who came to honor Doug Lebda. Industry titans flew in from across the country. The first LendingTree team alumni members I encountered were both in from the West Coast – Gabriel Dalporto and Nikul Patel, NACD.DC
Gabe Dalporto and Nikul Patel
Former North Carolina Governor and LendingTree Board Member Pat McCrory delivered a eulogy.
Former North Carolina Governor and LendingTree Board Member Pat McCrory
Current and former LendingTree executives filled entire rows. Employees, partners, entrepreneurs Doug had mentored, former team members whose lives he’d changed – they all came.
Founders Hall in Charlotte – packed house
Doug’s two oldest daughters Rachel and Abby took the stage with remarkable composure. Rachel shared how her dad had become “hopelessly addicted to ChatGPT” – I thought to myself that I may have some fingerprints on that addiction. Both daughters emphasized what mattered most – they knew every moment of every day how much their father loved them and that he was always there for them. I was brought to tears, and it seemed like the rest of the Hall was as well.
Every Charlotte trip for fifteen years had been about Doug or LendingTree. This was my first without that kind of joyful expectation. Industry legends had delivered eulogies, but in a quiet moment after the service, I realized the truest eulogy was the packed room itself – hundreds of lives Doug had touched, each carrying forward a piece of his unstoppable drive to solve problems and help others bloom.
RECEPTION – QUAIL HOLLOW CLUB
American Flag at Half-mast at Quail Hollow Club in Honor of Doug Lebda
The American flag at Quail Hollow was appropriate hung at half-mast.
The reception was a joyous celebration environment. Upon entering the venue, the first group I encountered were fellow lead gen OGs, all tightly connected to Doug through the years – Phillip Baltazar, Bruce Cook, and Scott Peyree.
SPF, Philip Baltazar, Bruce Cook, and Scott Peyree at Quail Reception
I also connected with other legends in the Doug Lebda/LendingTree ecosystem including:
Tamara Kotronis
Doug’s wife Megan delivered the most touching reflection of Doug imaginable.
The seeds given out as memorial gifts came with a note on the back of the package that included the line “Doug found joy in planting seeds, not just in the ground, but into ideas. He nurtured dreams, encouraged progress, and believed that ideas are wasted without action.”
Take-home Memorial Gift Seeds
People clutched those seed packets like precious artifacts.
TIMELINE DECLARATION
I have known OF Doug since 2000 and I have known Doug personally since 2008.
In the time since then, I have come to know Doug Lebda as a visionary entrepreneur who built what we all aspired to build as Internet entrepreneurs. A Bucknell graduate who earned his MBA from the University of Virginia’s Darden School of Business (and sat on their Board), Doug started his career at PricewaterhouseCoopers as an auditor and consultant. But it was his own frustrating experience getting his first mortgage in 1996 that led him, at just 26 years old, to become the Founder of LendingTree. He had a simple yet revolutionary idea: instead of consumers going to multiple banks, banks should compete for consumers’ business online. Over the next three decades, he led LendingTree through an IPO in 2000, survived the dot-com crash in 2001, orchestrated an acquisition by IAC in 2003, navigated a spin-off in 2008, and ultimately transformed it into a multi-billion-dollar public company. Doug literally invented the online lending marketplace and transformed how millions of Americans shop for financial products.
“When Banks Compete, You Win”
Yet, from my perspective, Doug was a different kind of Internet tech CEO. He never leaned into the “visionary” label that was often applied to him by others, confessing to me often that he considered himself more of a conventional finance guy than a tech innovator. He didn’t buy into “move fast and break things” or believe the Internet would change everything. For Doug, technology was a tool – the “how” not the “what” – a philosophy he later applied to AI. His business heroes were more akin to Jack Welch, Warren Buffett, and Bob Iger than Larry Page/Sergey Brin, Steve Jobs, or Jeff Bezos. He was perpetually annoyed that Google seemed to extract 70% of the value in Lead Generation and Customer Acquisition on the Internet. And unlike many tech CEOs I’ve known, Doug deeply cared about the consumer users, always putting their needs at the center of his decisions.
Doug’s superpower was his work ethic, persistence, and grit – qualities that he told me were gleaned from his #1 hero – his dad, Bob Lebda – which perfectly embodied his athletic pursuits. He ran marathons with the same determination he brought to business, understanding that success was about endurance, not sprints. When he completed the Ironman Triathlon in Kona at age 40, it became the perfect metaphor for his career path: relentless forward motion through every challenge and at any age.
Doug Lebda Competing at Iron Man Triathlon in Kona at Age 40
As a business colleague and friend, Doug changed the trajectory of my career. In 2009, LendingTree became one of DoublePositive’s live call transfer partners, launching a relationship. Between 2012 and 2014, he tried three times to acquire DoublePositive – not for our technology or P&L, but because, as he emphatically told me that he wanted to buy “ENTREPRENEURS.” During some of my darkest business hours, Doug gave me a masterclass in strategic thinking with his legendary email advice: “If you’re not selling, you’re actually buying.” That email changed everything for me. In 2021 when I founded my 5th startup business Symphony42, AI Agents for Customer Acquisition. Doug immediately became an advisor/shareholder on the founding cap table, texting me “Of course. know your rank in my life! Can’t wait!”
August 10, 2021 Text from Doug about Being Part of Symphony42
Beyond business, Doug was a devoted family man and community leader. He was a loving husband to Megan – who stood by him through every transformation of LendingTree and who was the anchor that allowed him to take such bold risks – and a father to Rachel, Abby, and Sophia, who, as Rachel and Abby shared at his service, knew every moment of every day how much he loved them and that he was always there for them. He achieved the ultimate Pittsburgh fan’s dream by becoming a minority owner of the Steelers. He was a member of YPO’s Southern 7 Chapter, which he joined at my urging after speaking at our YPO DC/Baltimore Chapter event in 2011. He was someone who former governors eulogized, whom industry legends gathered to honor, and who, despite all his success, would drive across town to have breakfast with a friend in Ballantyne and literally get giddy showing off his new black F-150 pickup truck.
Doug Lebda with Michael Jordan and Breakfast in Ballantyne with Me
For twenty years, Doug was my BFF and colleague. For twenty-five years, he has been my inspiration.
ORIGIN STORY – PARALLEL PATHS
The story of my relationship with Doug begins long before we ever met. In 2001, while Doug was building LendingTree into a national powerhouse, I joined Jason Goldsmith to build TheLoanPage.com, which we openly described as a “little LendingTree.” We weren’t trying to hide our admiration – we were explicitly modeling ourselves after what Doug had created. TheLoanPage.com grew to become what we believed was the fourth-largest player in the mortgage lead space, behind LendingTree, LowerMyBills.com, and Nextag. We were David to Doug’s Goliath, and we studied every move LendingTree made.
Our paths nearly crossed in January 2003 when LendingTree sent two executives, Jeff Lyons and Kim Gorsuch, to Maryland for a full day to evaluate TheLoanPage.com for acquisition. It was surreal to have LendingTree – the company we’d modeled ourselves after – sitting in our conference room considering acquiring us. But the timing wasn’t right. LendingTree was long-form only at the time, not having yet acquired GetSmart for a short-form offering, and they wanted us to drive traffic to LendingTree.com instead of maintaining our own brand. We were unwilling to give up our identity, and the deal fell apart. Doug and I wouldn’t actually meet for another five years.
During this same period, Stein Kretsinger at Advertising.com noticed something interesting – LendingTree was doing nine figures in revenue but without using any of the sophisticated analytics that Advertising.com employed for traffic acquisition, right-pricing ad inventory, and other performance marketing methods. Stein left to become Entrepreneur in Residence at Battery Ventures with a mission to acquire a leading mortgage leads startup, inject the religion of analytics, and stand up a serious competitor to LendingTree. This led to Battery acquiring TheLoanPage.com with Stein as the new CEO. Even after the acquisition of TheLoanPage.com by Battery Ventures, my admiration for what Doug had built only grew.
I finally met Doug in person in 2008 at the TARGUSinfo Online Lead Quality Summit. By then, Barry Diller had acquired LendingTree for close to $1 Billion. As part of IAC, Diller named Doug the COO. But by 2008, with the mortgage crisis in full swing, LendingTree stock was dragging down the entire IAC portfolio. Diller spun LendingTree back out and asked Doug to return and turn it around, incentivizing him with a massive equity grant. Doug came back with a vision of rebranding LendingTree to TREE.com – a multi-vertical lead generation business, not just mortgages. He’d recruited my friend Keith Moore as one of his key executives, and Keith interviewed Doug onstage at the summit where Doug presented his vision.
I’ll never forget what Doug said during that interview – he was tired of hearing other startups describe themselves as “the LendingTree of XYZ.” He didn’t want to be the model anymore – he wanted to BE the LendingTree of everything. It was classic Doug – ambitious, comprehensive, and slightly annoyed that everyone was copying his homework. Immediately after the interview, Keith brought Doug over and introduced us, declaring DoublePositive and me and DoublePositive as important players in the growth and development of the lead generation space. After years of building a “little LendingTree,” I was finally shaking hands with the man himself.
BREAKTHROUGH – VEGAS 2009
The transformation from industry connection to BFF happened at the 2009 LendingTree Lender Summit in Las Vegas. DoublePositive had paid thousands to LendingTree to be the lead sponsor of the event, and we were determined to make an impression. DoublePositive co-founder Joey Liner was offered the keynote, and he absolutely killed it. Multiple attendees told me afterward that Joey looked and sounded like Steve Jobs up there on the stage, evangelizing the future of live calls in lead generation with the same intensity and vision that Jobs brought to product launches. It was a defining moment for DoublePositive, but more importantly, it was about to become a defining moment for my relationship with Doug.
Right after Joey’s keynote, LendingTree customer and industry legend Phil Balthazar took the stage. Phil had been one of LendingTree’s first customers ever and served on their Lender Advisory Board. Without any prompting from us, he began gushing about DoublePositive’s capability to turn LendingTree’s form-fill data leads into inbound calls for his mortgage origination sales team. He told the entire room how his production system would “light up” with activity, making him genuinely happy. Here was one of Doug’s original customers, publicly validating our partnership in front of Doug’s entire ecosystem. The timing couldn’t have been more perfect.
Later, at the closing happy hour, I caught up with Doug at the bar, along with my friend Dave Helmreich (with TARGUSinfo at the time). I had brought a printout of what we called the “DoublePositive Evolution Slide” all folded up in my blazer pocket – the same image we’d used to raise three rounds of venture capital. It showed the evolution from CPM (banner ads) to CPC (clicks) to CPA/CPL (leads) to CPT (call transfers), with the famous evolution of man imagery showing a progression from ape to upright human, each carrying the respective advertising delivery model. I proudly showed it to Doug, expecting him to appreciate the clever visualization of how our industry was evolving.
DoublePositive Evolution Slide
“So, you’re calling me a monkey?”
Doug took one look at the image, looked up at me, and with perfect comedic timing asked: “So, you’re calling me a monkey? Not a very compelling partner pitch in my opinion.” The delivery was so unexpected and so perfectly deadpan that I burst out laughing. It was hilarious, and it immediately broke through any remaining professional distance between us. This wasn’t a formal CEO maintaining corporate decorum – this was a real person with a wicked sense of humor who could find the absurdity in a moment.
As the happy hour continued, Doug and I fell into deeper conversation. He told me about his relationship with Jack Welch, whom he’d gotten to know through IAC and absolutely adored. He recommended I look into Jack Welch’s programs for CEOs, seeing something in me worth developing even though we’d only known each other for a year. The conversation meandered from business philosophy to personal aspirations, from industry war stories to shared frustrations about Google’s dominance in our space.
Something shifted during that conversation at the bar. We went from being Doug Lebda of LendingTree and Sean Fenlon of DoublePositive to just being Doug and Sean – two guys who happened to love the same industry, shared the same competitive drive, and could make each other laugh. By the time the happy hour ended, we weren’t just business associates anymore. We were friends. Real friends. The kind who would text each other about marathons, books, and private jets, who would share unvarnished experiences about hostile investors on Wall St. That night in Vegas, at a bar in MGM Grand, discussing everything from conversion rates to Jack Welch’s management philosophy, Doug Lebda became my BFF.
FIRST PARTNERSHIP
In January 2009, DoublePositive and LendingTree entered into a partnership that would fundamentally change both companies. We drafted a press release that began:
“DoublePositive and LendingTree have entered into a partnership that will for the first time allow residential mortgage loan originators to purchase and receive LIVE Hot Transfers of LendingTree mortgage leads.”
This was groundbreaking. LendingTree had built an empire on selling form-fill data leads – consumer data delivered in real-time to lenders who then had to chase down those consumers themselves. We were proposing something radically different – DoublePositive would take those LendingTree leads, instantly contact and qualify the consumers by phone with live domestic call center agents, and then transfer genuinely-interested and qualified borrowers directly to loan officers. It was LendingTree’s first official live call transfer partnership, marking their expansion into a delivery model that went beyond just data.
The relationship truly blossomed after a trip Joey Liner and I made to Charlotte in July 2010. We had dinner with Doug at Del Frisco’s, the kind of steak dinner where business talk gradually gives way to personal stories and shared ambitions. What struck me most was Doug’s follow-up. The very next morning – a Saturday – Doug sent an email that began:
“Was great to spend time with both of you this week. Thanks so much for dinner, but more importantly for the partnership. We definitely have this relationship on the tracks and heading in the right direction. We’ll keep ramping it up.”
CEOs of public companies don’t typically send warm Saturday morning emails after business dinners. But Doug did. When I replied, mentioning that Joey was working on a follow-up and joking that Doug had beaten us to it, I also noted that this was our fifth partnership initiative together. We weren’t just doing a deal – we were building something together. This partnership laid the groundwork for everything that would follow: the acquisition attempts, the strategic advice, the friendship that would span the next fifteen years literally until his final days.
WORLD DOMINATION VISION
By November 2010, Doug’s vision for the future of lead generation had crystallized into something approaching a manifesto. After months of working together on our live call transfer partnership, he sent an email that would become legendary within our companies. The subject line was innocuous enough: “DoublePositive, short form, and hot transfers.” But the content was pure Doug Lebda – ambitious, direct, and completely unfiltered.
“So we’re all on the same page,” he wrote to his team, copying Joey Liner, “We need to blow out Hot Transfers. We need to beat the crap out of our competition in marketing, produce leads like crazy, and if we can’t sell them directly, we’ll turn them into hot transfers and sell them that way. And, if our sales team can’t sell the hot transfers and lenders are capping out, then send them to LendingTree Loans.” Then came the line that perfectly captured Doug’s ambition and competitive fire: “Seriously, this is one of the keys to world domination in online mortgage. Go get every f-ing lead on the Internet, drive them to a call center, and transfer them to a lender.”
This wasn’t corporate-speak or carefully crafted PR language. This was Doug laying out his actual strategy in the bluntest possible terms. The email showed what made Doug different from other CEOs I’d worked with. While others talked about market share and quarterly earnings, Doug talked about world domination. While others focused on optimization, Doug wanted every single lead on the Internet. The plan was breathtakingly simple and audaciously comprehensive: capture everything, qualify everyone, and own the entire funnel from initial interest to live conversation.
Joey forwarded the email to our management team with a note that said it all: “LOL.. Sean I told you. Doug surprised me this AM. This is going to be fun!”
Even Joey, who’d pitched DoublePositive to hundreds of executives, was taken aback by Doug’s intensity and directness. This wasn’t just buy-in from a partner – this was a CEO putting our model at the center of his growth strategy. Doug had taken our live call transfer concept and weaponized it into a plan for complete market dominance.
WARTIME CONSIGLIERE
In the years 2010-2014, I found myself in the darkest period of my business career where there was increasing misalignment between Founders and investors – investors wanted liquidity, but we wanted to keep building and take DoublePositive public. The tension was becoming unbearable. During a Ravens-Steelers email thread that Joey Liner had started as a joke, I mentioned to Doug that I’d been in brutal Corp Dev meetings. What happened next changed everything.
Doug responded with what I can only describe as a masterclass in strategic thinking – a detailed, radical, and completely unvarnished playbook for navigating misalignments. The email was unlike anything I’d ever received from another CEO. “Leaving us out of it,” he began, “please feel free to use me as a friend for any advice and guidance here.” Then he proceeded to lay out exactly how to manage a process and maintain effective control when one set of stakeholders wanted a sale. His advice was breathtakingly candid. The strategic sophistication was remarkable.
“REMEMBER – if you’re not selling, you’re actually buying. Whatever this deal clears at is now the floor on where your plan starts kicking in on any new deal.” He was teaching me to think like a buyer while being a seller, to use the process itself as the negotiating scaffolding.
The impact was immediate and lasting. I went into our offsite planning session with a completely different mindset. Instead of feeling trapped, I understood my options. Doug’s advice became a mental model I’ve used ever since. Whenever I face a situation where I feel powerless, I remember Doug’s email and ask myself: “Am I thinking like a seller or a buyer? And which one do I actually want to be?” That single email fundamentally changed how I approach every negotiation for the rest of my life.
PERSONAL BONDS
Beyond the business partnership and strategic advice, Doug and I connected on a level that transcended deals and term sheets. One night at a bar in Charlotte after a steak dinner, I decided to test the waters on something more close to home… “Hey Doug,” I asked, “I’m curious, where are you on politics?” Without missing a beat, he responded with two words: “Atlas Shrugged.” It was the perfect answer for me at that moment. I started laughing and told him I’d literally bought Atlas Shrugged for my entire team the previous year – in hardback, paperback, audiobook, Kindle, and even CliffsNotes for those who wouldn’t commit to the full thousand pages. Doug later revealed himself to be more politically complex and more religiously grounded than that initial answer suggested, but in that moment, those two words created an instant philosophical connection between us.
Atlas Shrugged by Ayn Rand
Our shared interests extended to endurance sports and the mentality they require. When Doug was preparing for the Ironman Triathlon in Kona – a feat he’d accomplish at age 40 – I recommended he read “Born to Run” by Christopher McDougall. I was curious whether the book about the hidden tribe of super-athletes and the secrets of running had influenced his training. His emailed response was characteristically brief: “Before.” He’d already discovered it. Of course he had. Doug approached endurance athletics the same way he approached business – with comprehensive preparation and an almost obsessive attention to what could give him an edge. The Ironman wasn’t just a midlife crisis checkbox for Doug – it was the perfect physical manifestation of his business philosophy. Success came from preparation, persistence, and the ability to keep moving forward when everything hurt or was existential.
There were unexpected parallels in our lives that we’d discover and laugh about. At the 2012 YPO event in Baltimore, when I drove Doug to the airport after his perfect-10 rated talk, Doug noticed that we drove identical vehicles – black BMW 7-Series sedans. “I drive the exact same car,” Doug said with a grin. It was a small thing, but it felt like another sign that our paths were meant to intersect. We’d both chosen the same symbol of mobility, the same color, the same everything. Two entrepreneurs who’d started at different times, built different companies, but somehow ended up in the same place, literally driving the same car – make, model, and color.
The NFL provided an ongoing source of friendly rivalry and connection. Doug was a generational Pittsburgh Steelers fan – he had been rooting for the black and gold since he was a kid growing up in Pennsylvania. I was a lifelong Redskins fan. The rivalry wasn’t as perfect as Steelers/Ravens or Redskins/Cowboys, but it was still with historic franchises, with multiple Super Bowls between them, and just enough geographic distance to make it interesting. Doug would later achieve the ultimate fan’s dream by becoming a minority owner of the Steelers in the 2020s, something that filled him with a joy that no business success could match. I was thrilled for him. He’d literally bought a piece of his childhood dream. For years, Doug would forget I was a Washington fan and assume I supported the Ravens like Joey Liner. I’d have to remind him, and he’d laugh and apologize, then forget again the next season. It became its own running joke – Doug’s inability to remember my team allegiance despite remembering every detail of every business deal we’d ever discussed.
YPO CONNECTION
At the end of the 2011 LendingTree Lender Summit, where DoublePositive was again the lead sponsor, I pulled Doug aside during the closing happy hour with a request. Would he come to Maryland and speak to my YPO DC/Baltimore chapter? I also encouraged him to join YPO himself – the Young Presidents’ Organization that had become such an important part of my life. Doug immediately said yes to speaking, and to my delight, he joined YPO before the event. The fact that he joined at least in part due to my influence made me oddly proud, like I’d given him something back after all he’d given me.
The event took place on April 19, 2012, at the newly opened Four Seasons in Baltimore. I was the co-day chair along with my chapter mate John Shmerler , who happened to be in the same Bucknell fraternity as Doug, as was JM Schapiro , our Chapter Chair that year. The format was simple – me interviewing Doug on stage, guiding his story for our members. We titled it “Repairing the Bubble,” and Doug delivered absolutely. The event scored a perfect 10 out of 10 in the member ratings and reviews – an almost impossible achievement in a room full of successful, critical CEOs who had seen countless speakers.
Seven years later, Doug graciously returned to our chapter for the January 2019 retreat in Annapolis. Along with John Corso , I was day chair for the retreat in Annapolis, MD and had asked Doug to be our keynote speaker. This time, I’d arranged for him to be interviewed fireside-chat style by our chapter’s own Scott Ferber , who had built Advertising.com at the same time Doug was building LendingTree. I’d actually introduced Doug and Scott at YPO Disney in 2014, and reuniting them for this fireside chat felt like bringing the story full circle. The online advertising and lead generation pioneers, on stage together, in conversation.
Doug Lebda and Scott Ferber Fireside Chat 2019 YPO DC/Baltimore Chapter Retreat Keynote
But before the keynote could happen, our chapter had arranged a surprise. Marines burst into the room and herded everyone – speakers included – into an adjacent space for mandatory physical training. I watched, somewhat mortified, as Doug, the CEO of a public company and our invited guest, was suddenly doing squats and exercises with uniformed Marines barking orders. But Doug didn’t hesitate. He jumped right in, squatting and sweating along with the rest of us, his face a mixture of amusement and determination. The photo from that moment – Doug in full squat position with Marines and YPO members – captures something essential about him. He never stood on ceremony. If the group was doing something, Doug was doing it too.
Doug Lebda Participating in Surprise Squat Exercises Before his Keynote
After the PT session and his fireside chat with Scott, Doug pulled me aside with a huge grin. “You guys are crazy,” he said, still catching his breath from the Marine workout. Then he added, “You guys have a GREAT chapter.” Coming from Doug, who didn’t throw compliments around lightly, it meant everything. The photos from that day – Doug and Scott on stage, arms raised in triumph, the pure joy on Doug’s face – are among my most treasured. They capture Doug at his happiest – surrounded by entrepreneurs, sharing wisdom, fully engaged in the moment, and always game for whatever came next, even if it meant surprise military PT before his keynote speech.
Doug Lebda, SPF, Scott Ferber
THE PERFECT DAY
December 14, 2012, stands out as one of those rare days where everything aligns – business, friendship, success, and celebration all converging in a perfect twenty-four hours. It started with an almost impossible scheduling challenge. I was set to have a steak dinner with Doug in Charlotte, but I’d also just learned that the DoublePositive executive team needed to meet the new EDMC CEO in Pittsburgh the next morning at 9 AM. EDMC was our biggest customer by far, and this meeting was critical. The geography was completely untenable – there was no commercial flight pattern that would let me have dinner with Doug in Charlotte and make a 9 AM meeting in Pittsburgh. The only solution was to fly private, something I’d never done before.
So I did it. I flew on a private jet from Charlotte to Pittsburgh, then back home to BWI. Stepping onto that plane after dinner with Doug, I felt like I’d crossed some invisible threshold. This wasn’t just about the luxury of private travel – it was about refusing to choose between two important relationships, about finding a way to make the impossible possible. The EDMC meeting the next morning was a triumph. We walked out with a commitment for regular C-level meetings to deepen our strategic relationship. I immediately emailed Doug from the taxi back to the airport: “I think we killed it.”
Doug’s response perfectly captured who he was. Instead of a perfunctory “congrats,” he engaged with real interest. Then after my update, we fell into an easy exchange about future private jet options (he connected me with someone who could advise on fractional ownership), about a Darden professor who taught negotiations, and about bringing in new analysts in to cover TREE stock. This wasn’t a CEO maintaining a vendor relationship. This was a friend genuinely interested in my success.
But the day wasn’t over. That same evening – December 14, 2012 – DoublePositive declared a multi-million-dollar cash dividend to all shareholders, both preferred and common. This was extraordinarily rare for a tech startup, almost unheard of. I mentioned this to Doug in our email exchange with characteristic understatement: “Oh and our multi-million-dollar dividend just hit the wires a moment ago :-)”
Doug’s final email that night contained seven words that meant more to me than any dividend or deal: “Last night was awesome. Really enjoy our friendship.” This wasn’t business language. This wasn’t CEO speak. This was Doug Lebda, who ran a public company worth hundreds of millions of dollars, taking time on a Friday night to tell me he enjoyed our friendship. The fact that he separated this from all the business discussion – made it its own statement – showed its importance to him. December 14, 2012, was perfect not because of the private jet or the successful meeting or even the million-dollar dividend. It was perfect because it crystallized what Doug and I had built together – a friendship that transcended business, where success was shared and celebrated, where a CEO could become a true friend who’d write “Really enjoy our friendship” and mean every word.
ACQUISITION ATTEMPTS
Between 2012 and 2014, Doug tried three times to acquire DoublePositive, and the story of these attempts reveals everything about who he was as both a businessman and a friend. The first serious attempt came in 2012 when I brought the DoublePositive team to Charlotte to present to the LendingTree team, including Doug, Gabe Dalporto, Neil Salvage and Bruce Cook. We walked them through our core call transfers business, our mobile pay-per-call innovations, our success in home services where LendingTree was struggling at the time, and our profitability in EDU. LendingTree was impressed on every level. After the meeting, Doug called me privately with a level of enthusiasm I’d rarely heard from him. “I’ve never been as excited to acquire a business as I am about DoublePositive,” he said. When I asked him what exactly he thought he was buying, his answer was emphatic and immediate: “ENTREPRENEURS!”
That single word – delivered with Doug’s characteristic certainty – revealed everything about his acquisition philosophy. While other acquirers focused on EBITDA multiples, tech stacks, or customer logos, Doug saw businesses as collections of talented people. He wasn’t buying our platform or our processes. He was buying Joey Liner’s sales genius, our team’s scrappy innovation, and the entrepreneurial energy that had built something from nothing. From Zero to One. The fact that he shouted “ENTREPRENEURS” with such enthusiasm showed he understood that in the performance marketing space, essentially the people were the product.
Doug wrote with brutal honesty to the DoublePositive Board – “What we value here is a management team we know and trust, who are highly entrepreneurial and scrappy, and who we believe that with our brand we can make this worthwhile.” Then came the line that cut to the heart of everything: “We’re basically buying this company for the management team. Shareholders need to completely recognize that without a handful of people, this business isn’t frankly really a business.”
Unfortunately, we did not get home on the deal with Doug and LendingTree. DoublePositive was ultimately sold on March 23, 2015, to OSG, a strategic acquirer that nobody was excited about. Doug never got his ENTREPRENEURS. The investors got their liquidity, but at the cost of what could have been a brilliant combination. Doug and I often joked afterward about what might have been – the LendingTree stock price increased 20X+ in the years after the failed acquisition attempt – but I could tell it genuinely bothered him. Not because he missed out on a deal, but because he knew we could have built something special together, and emotional irrationality had prevented it from happening.
THE CONNECTOR
One of the most profound aspects of my relationship with Doug was our role as connectors – bringing together the titans of our industry in ways that created lasting value. The most surprising connection came in April 2012 when I discovered that Doug Lebda and Dave B. Blundin had never met. Dave was another one of my BFF heroes and the head of Cogo Labs and Link Ventures – one of the smartest investors and entrepreneurs in the world. Dave had just joined the DoublePositive board. Doug was, well… Doug Lebda. I sent an email with the subject line “Introducing Dave Blundin to Doug Lebda” that began: “Dave I copied LendingTree founder/CEO Doug Lebda here. I learned today that you two have never been introduced. The universe should be ashamed of itself – I’m going to fix that here. :-)”
In May 2014, at YPO Disney, I orchestrated another meaningful connection. Doug and Scott Ferber – who had built Advertising.com at the same time Doug was building LendingTree – were both there with their families, and I made sure they met in person. I sent them both an email afterward with the subject “Scott Ferber & Doug Lebda” that said simply: “Bucket-list checked today – I was able to introduce my two heroes in-person – the two original Internet entrepreneurs. :-)” I meant it. These were the guys who had invented our industry, who had figured out how to monetize the Internet before anyone else knew what digital advertising even was. Watching them connect, share war stories, and recognize each other as peers was like watching two hall-of-famers meet at center court.
At YPO Disney, families are hosted and led through the parks by Disney Personal Guides, who often guide celebrities in the parks. In 2014, Doug was spotted by other attendees of the parks and was a victim of mistaken identity – the people who noticed Doug and his family with the guide confused him for Dave Matthews, which was apparently common outside of Disney as well. In this picture at YPO Disney, Megan holds up a picture of Dave Matthews next to Doug to demonstrate the similarity – the likeness is striking.
Doug Lebda Mistaken for Dave Matthews at YPO Disney 2014
The most poignant introduction came in April 2015 when I introduced Doug to Seth Birnbaum, founder and CEO of EverQuote (who tragically passed away in 2020). I was visiting Seth and Dave Blundin in Cambridge when Doug’s name came up. We were both gushing about what Doug had accomplished with LendingTree. I sent Doug an email that night – “Seth is awesome – a chronic over-achiever and a serial entrepreneur – he has grown EverQuote to the place where it is ready to file to go public. Your name came up – we were both gushing over what you’ve done with TREE. I promised Seth an email intro.”
Doug was dealing with a challenging earnings report at the time but still made the connection. Seth and Doug would go on to become two of the most successful public company CEOs in our industry. The fact that I introduced them – these two legends who are both now gone – carries a weight I couldn’t have imagined at the time.
CONTINUED JOURNEY
After DoublePositive was sold to OSG in March 2015, my relationship with Doug didn’t skip a beat. If anything, freed from the complexities of potential acquisition conflicts, our friendship deepened into something more personal. That same year, Doug invited me to his home at Quail Hollow, the prestigious golf course community where he lived. Walking into Doug’s personal space, seeing him with Megan and his daughters, watching him in his element as a father and husband rather than a CEO, charmed me completely. This wasn’t a business meeting or a strategy session. This was Doug sharing his life with me, introducing me to the people who mattered most to him. The girls were bright and engaging, Megan was warm and welcoming, and Doug was more relaxed than I’d ever seen him. It was one thing to know Doug the entrepreneur, another entirely to know Doug the family man.
In 2016, we had a moment of perfect symmetry that captured our parallel journeys. Doug won the LeadsCon Executive of the Year Award, and I immediately congratulated him on the same email thread where he had congratulated me for winning Ernst & Young’s Entrepreneur of the Year back in 2011. My note was simple: “Saw the LeadsCon Executive of the Year. That’s fantastic. You’re on quite a roll. Enjoy it. :-)” Doug’s response was typically Doug – apologetic about the late reply but genuine in his appreciation.
During these years, I watched Doug navigate LendingTree’s expansion beyond lending with a mixture of admiration and empathy. The company experienced tremendous traction in verticals closest to lending – personal loans and credit cards were natural extensions that consumers understood. But the further Doug pushed from the core lending business, the more challenges emerged. DegreeTree.com, their attempt to sell education leads to for-profit schools, struggled to gain traction. Insurance proved so challenging that Doug ultimately acquired QuoteWizard in 2018 for over $300 million rather than trying to build it organically. Through it all, Doug maintained his characteristic persistence, treating each challenge as a problem to be solved rather than a failure to ruminate about.
The QuoteWizard acquisition in 2018 would prove transformative, eventually representing more than 50% of LendingTree’s total revenue. Scott Peyree, who had founded QuoteWizard after his first startup World Class Strategy was acquired, became a key figure in LendingTree’s next chapter. Doug spoke to me about Scott with the kind of respect he reserved for true entrepreneurs. He saw in Scott the same scrappy innovation and relentless execution that he valued above all else. When Doug tragically passed, Scott had already been named in the CEO succession plan – a choice that Doug had essentially telegraphed through years of praise and increasing responsibility.
SYMPHONY42 ERA – THE FINAL INNOVATION – STILL BUILDING IN 2024-2025
In 2021, when I founded Symphony42 with Dave Blundin, Doug was one of my first calls. The company vision was audacious – essentially DoublePositive Part 2, but replacing live human call centers with AI software, using multiple Conversational AI platforms in a champion/challenger methodology just like I used to do with outsourced call centers. I texted Doug asking if I could get on his schedule to tell him about it, explaining that if I could get Conversational AI to actually “sell” like Red Ventures, not just qualify or screen consumers further down the funnel like DoublePositive had done.
Symphony42 – AI Agents for Customer Acquisition
Doug’s response was instant and unequivocal: “Any day except Thursday. Tek doug will snag this and know your rank in my life! Can’t wait!” That text perfectly captured Doug’s enthusiasm for new ventures and our friendship. The phrase “know your rank in my life” wasn’t corporate politeness – it was Doug telling me exactly where I stood with him. When we met, Doug immediately joined as advisor/shareholder on the founding cap table of Symphony42. No lengthy due diligence, no complex negotiations. Doug believed in the vision and, more importantly, he believed in me.
The early years of Symphony42 were brutal. 2022 was particularly tough because we were limited to legacy NLP, STT, and TTS Conversational AI models that simply weren’t sophisticated enough for what we were trying to build. We were essentially trying to create the future with yesterday’s tools. Doug stayed supportive throughout, checking in regularly, offering introductions, never wavering even when our progress was slower than hoped. He understood the long game better than most – he’d survived the dot-com crash, the 2008 financial crisis, multiple transformations of LendingTree. He knew that breakthrough innovations required patience.
Everything changed on November 30, 2022, when OpenAI released ChatGPT. By early 2023, I had become a paid power user of every major LLM platform – ChatGPT, Claude, Gemini, and others. I was obsessed with the potential and started aggressively pushing Doug to join me in this new world. He was initially resistant, the practical operator in him skeptical of another Silicon Valley hype cycle. But I kept pushing, sending him examples, use cases, analyses of LendingTree earnings calls, showing him how these tools could transform not just Symphony42 but LendingTree itself. Eventually, Doug capitulated – at least to ChatGPT, though not to my “all of them” approach. The fact that his daughter Rachel would later mention at his services that he’d become “hopelessly addicted to ChatGPT” and that I may have some fingerprints on that remains one of my proudest contributions to Doug’s final years with us.
April 2024 marked a pivotal moment in both Symphony42’s journey and Doug’s embrace of the AI revolution. Doug invested in Symphony42 and invited me to bring Greg Yardley and Brian Ocheltree to Charlotte to meet with the entire senior LendingTree and QuoteWizard team to discuss the future of AI Agents at LendingTree.
The photo from that meeting shows Doug fully engaged, his trusted Chief of Staff Vita DeCeglio at his side, asking hard questions but with unmistakable excitement in his eyes.
Symphony42 Team Presenting to LendingTree QuoteWizard Team April 2024
Doug saw in AI what he’d seen in the Internet thirty years earlier – not a revolution in itself, but a tool that, properly applied, could transform how millions of people made financial decisions. Doug would say to me, “AI is the ‘HOW’, not the ‘WHAT’” and it has stuck with me and been incorporated into countless strategic decisions for Symphony42. That he was still innovating, still pushing, still excited about the future at 55 years old, defined everything about who Doug Lebda was as an entrepreneur and as a human being.
On September 29, 2025 – just days before his passing – Doug sent me what would be his final text message at 2:09 AM. It wasn’t about legacy or reflection or any of the things you might expect from a last communication. It was about his next big idea. “I’m def up for home pros,” he wrote. “Want to talk to you about how I’d do it. And frankly I’d fund that myself outside of tree.” Then he explained his vision: “It was the parallel idea I had when I started lendingtree. It’s basically a property manager for the masses. Don’t even need vendors to compete – we get preferred vendors and they do it our way. Homeowners can have all the data and can have their home managed for them like I do.”
This was quintessential Doug Lebda. At 55 years old, after building LendingTree into a multi-billion-dollar public company, after achieving financial success beyond most people’s wildest dreams, after becoming a minority owner of his beloved Pittsburgh Steelers, Doug was still innovating. He wasn’t content to rest on his accomplishments or coast on his success. He had identified another problem that frustrated him – the complexity of home maintenance and management – and he was already working out how to solve it for millions of Americans. The fact that he was willing to fund it himself, outside of LendingTree, showed this wasn’t about adding another revenue stream to his company. This was about the pure entrepreneurial drive to fix something that was broken.
The vision he outlined was brilliant in its simplicity, classic Doug in its ambition. Just as LendingTree had inverted the mortgage process – making banks come to consumers instead of the other way around – this new concept would invert home services. Instead of homeowners scrambling to find contractors, manage repairs, and maintain their properties, they would have a “property manager for the masses” that would handle everything for them. Doug noted it was “the parallel idea I had when I started lendingtree,” revealing that even back in 1996, he’d been thinking about this problem. Nearly thirty years later, he was ready to solve it.
My Last Text Message from Doug – still innovating
What strikes me most about this final text is the continuity it represents. Doug’s journey from that frustrated first-time homebuyer in 1996 to the seasoned CEO in 2025 was one long arc of solving consumer problems. He never stopped seeing inefficiencies that could be fixed, friction that could be removed, processes that could be democratized. The young man who had built LendingTree to simplify mortgage shopping had become the seasoned veterans who wanted to simplify home ownership itself, and he was just as excited about this new idea as he’d been about his first one three decades earlier.
I never got to have that conversation with Doug about how he’d build his property manager for the masses. Two weeks after sending that text, he was on his new farm in Western North Carolina, exploring where to build a house for his family’s future, when the ATV accident happened. But that final message stands as a perfect testament to who Doug was. He was a builder who never stopped building, a dreamer who never stopped dreaming, an entrepreneur who believed, as the seeds given out at his memorial service said, that “ideas are wasted without action.” His final communication to me wasn’t a goodbye or a summation – it was an invitation to build something new together. That was Doug Lebda – forever looking forward, forever solving problems, forever believing that the next great idea was just a conversation away.
CODA
Doug was so many things to all of us who knew and loved him. A devoted son, husband, father, colleague, and friend. But if I had to pick one word to describe him, it would be MAGNETIC INVINCIBILITY. Yet Doug’s magnetism was different from pure charisma. He benefited from what I call a “tailwind from early success” – he had created so much wealth for so many people, even before I knew him, that everyone wanted to be near him before they even met him or knew his personality. But once you met Doug, you realized the success was just the gateway. The real magnetism came from who he was as a human being – someone genuinely interested in your ideas, generous with his wisdom, quick with a joke, and always, always looking forward to what could be built next.
Doug’s true superpower was his work ethic, persistence, and grit. The marathons and Ironman Triathlon weren’t just hobbies or midlife achievements to check off – they were perfect metaphors for how he approached everything. Success wasn’t about being the smartest or the most visionary. It was about preparation, persistence, and the ability to keep moving forward when everything hurt. When Doug completed the Ironman in Kona at 40, he wasn’t trying to prove something to anyone else. He was living his philosophy – set an audacious goal, prepare relentlessly, and then simply refuse to quit until you cross the finish line. This is how he built LendingTree, how he survived the dot-com crash, how he navigated the financial crisis, and how he kept innovating until his final days.
His sense of humor was quick and disarming. The moment that captured it perfectly was when I showed him our evolution slide depicting the progression from banner ads to hot transfers using the famous evolution of man imagery. Doug looked at it, looked at me, and with perfect timing asked: “So, you’re calling me a monkey? Not a very compelling partner pitch in my opinion.” The ability to find absurdity in a serious moment, to puncture pretension with a well-timed joke, to make everyone around him feel like they were in on something fun – that was Doug’s gift. He could shift from discussing billion-dollar strategies to getting giddy about his new F-150 truck without missing a beat.
But perhaps what defined Doug most was his extraordinary generosity with wisdom and trust. When I was facing shareholder challenges, Doug didn’t just offer advice – he gave me a complete playbook for navigating the situation. When young entrepreneurs reached out, Doug made time. When friends needed guidance, Doug showed up. He shared knowledge the way he built businesses – comprehensively, practically, and without holding anything back. Doug believed that ideas were wasted without action, but he also believed that wisdom was wasted unless it was shared. In a world of founders who guard their secrets and CEOs who speak in platitudes, Doug Lebda told you exactly how the game was played and then trusted you to play it well.
EPILOGUE
The seeds given out at Doug’s memorial service came with a message that perfectly captured his philosophy: “Doug found joy in planting seeds, not just in the ground, but into ideas. He nurtured dreams, encouraged progress, and believed that ideas are wasted without action. As you plant these seeds, may they remind you to tend to your own growth and to help others bloom in ways they never imagined.” When I read those words, I immediately took a photo and uploaded it to ChatGPT – the AI tool I’d gotten Doug hopelessly addicted to – for analysis. The response distilled Doug’s entire life into three lines:
Seeds of ideas.
Growth through action.
Bloom by helping others.
Doug meant so much to so many people in so many ways that he is essentially immortal. His ideas live on in the millions of Americans who got better mortgages, found the right insurance, or improved their credit because of the marketplace he created. His mentorship lives on in the entrepreneurs he advised, funded, and believed in when no one else would. His philosophy of treating the Internet and AI as tools rather than revolutions continues to shape how pragmatic builders approach new technology. His family’s love, so beautifully expressed by Rachel and Abby at his service when they said they knew every moment of every day how much he loved them, will ripple through generations.
Standing with Doug felt like being carried by an unstoppable current toward something better. He had this way of making the impossible feel inevitable, not through mystical vision but through sheer force of will and relentless execution. When Doug decided something would happen, it happened. Not because he could see the future, but because he would work harder, persist longer, and think more strategically than anyone else. He was destiny wearing work boots, grinding out the future one day at a time.
I was the last person to leave Quail Hollow after the reception on October 19, 2025.
Last Person to Leave Quail Hollow Reception
Standing alone under the flag at half-mast, I couldn’t bring myself to walk away. Every trip ‘d made to Charlotte for fifteen years had been connected to Doug or LendingTree – always with excitement, always with anticipation of what we’d build or discuss next. This was my first Charlotte trip without that joy, and leaving felt like closing a chapter I wasn’t ready to end. The overcast sky that had greeted my arrival had given way to night, but I stood there anyway, remembering.
I thought about Dutch, Doug’s loyal dog, who had stayed by his side after the ATV accident, whose barking had led the search team to find him. I thought about Doug on that new farm, alone except for Dutch, exploring where to build a future house for his family. Even in his final moments, Doug was building, planning, creating a future. That was Doug – forever looking forward, forever solving the next problem, forever believing that the best was yet to come.
Doug, if you’re reading this from heaven, I want you to know – your guidance and experience-sharing saved my company and changed my life. Your friendship enriched my journey in ways I’m still discovering. Your belief in Symphony42 when it was just an idea, your trust when you shared your unvarnished wisdom, your joy over simple things like a new F-150 truck – these are the gifts I’ll carry forever. You showed me that success isn’t about being a visionary – it’s about caring deeply, working relentlessly, and helping others bloom in ways they never imagined.
We go on.
We persist.
We persevere.
We keep planting seeds and nurturing dreams and believing that ideas without action are wasted. Just like you taught us.
Though you set the bar impossibly high, your example lights the path forward. Every entrepreneur you mentored, every consumer you helped, every friend you advised carries a piece of your spirit forward. That’s your true immortality – not in monuments or memorials, but in the countless lives you touched who now touch others, spreading your influence like seeds on fertile ground.
Rest in peace, Doug Lebda. I will miss you so much. The universe, the Internet, and North Carolina will never be the same without you. The lead generation industry has lost its founding father. The Godfather of the space. Your friends have lost a wartime consigliere who told us the truth when we needed it most. But your family knows they were loved completely, your legacy is secure in the company you built and the people you developed, and your final vision of a “property manager for the masses” reminds us that you never stopped dreaming, never stopped building, never stopped believing that the next great idea was just a conversation away.
Doug meant so much to so many people in so many ways that he is essentially immortal.
Note on Back of Take-home Memorial Gift Package of Seeds
Seeds of ideas.
Growth through action.
Bloom by helping others.
–ChatGPT on Doug Leba
DeepDive Podcast about the Legendary Doug Lebda – Founder and CEO of LendingTreee – by NotebookLM
I generated and shared this AI-generated podcast with Doug on September 30, 2024 – he loved it and shared it with others in his circle – posted for the archives here forever:
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DeepDive Podcast about Doug Lebda](https://soundcloud.com/seanfenlon/deep-dive-podcast-about-the-legendary-doug-lebda-founder-and-ceo-of-lendingtree-by-notebooklm)
Originally published on LinkedIn. Read and comment on the original article →