When serial entrepreneur Bill Oesterle told an Indianapolis newspaper columnist last year that he was dying, it shocked those who hadn’t already heard of his Amyotrophic Lateral Sclerosis (ALS) diagnosis. Despite that knowledge, the news of his death last week was just as startling. 

As word spread, the tributes flowed. It seemed few companies in central Indiana were without a person who had a personal encounter with the business leader, Angie’s List co-founder, community activist and family man. The New York Times and Wall Street Journal wrote of his passing. 

Oesterle was a fast-talking, energetic champion for Indiana. A runner. A person who pushed himself and others to constantly think harder and differently. Don’t just push the envelope; tear it up. Don’t just bounce back from failure, leap higher, fueled by what it had taught you. Nothing, it seemed, could slow the man down. 

Then came ALS, a terminal degenerative disease, for which there is no cure. It affects nerve cells in the brain and spinal cord and robs its victims of muscle control over time. And while it slowed the man down, he fought against it—and for Indiana—until Wednesday, May 10, 2023, shortly after midnight.  

A celebration of Bill Oesterle’s life will be held on June 1, 3-8 p.m. at the Mavris Arts & Events Center (121 S. East St.) in Indianapolis.

WATCH VIDEO: The Trailblazer Award Tribute Video honoring Bill Oesterle from the 2022 TechPoint Mira Awards.

“Bill was relentless to the very end,” said Mike Rutz, CEO of MakeMyMove, which he cofounded with Oesterle and Evan Hock.  

Rutz and Hock both worked their way up to executive positions at Angie’s List during Oesterle’s tenture as CEO. 

“He never let an opportunity go by that he thought might help the business or help Indiana. He made sure to celebrate successes, but also to talk you through a failure and to make the most out of every opportunity whether that was for work or for play,” Rutz said. “He was in the people business more than anything. Showing them what he saw in them and helping them grow to their potential. His effect on the Indiana tech community is going to be felt for generations.” 

Scott Dorsey, co-founder and CEO of ExactTarget and now managing partner at High Alpha, met Oesterle when he rented space on the second floor of a rickety building on the Angie’s List campus in 2001 to launch what would become the city’s biggest tech success story.

“Bill’s passion for Angie’s List and lifting up Indianapolis’ East Side was evident from our first interaction,” Dorsey said. “Later, we benefited immensely from the Orr Fellowship and his brave community leadership and willingness to speak up on important issues even when it wasn’t popular. Most recently, his enormous courage to face ALS with optimism and keep challenging our tech community to make a bigger impact was quite remarkable.” 

That challenge was made during the 2022 TechPoint Mira Awards gala, one of the last times that Oesterle spoke publicly as his ALS progressed. It followed a speech from Eli Lilly and Company’s CEO Dave Ricks, who had said Indiana wasn’t up to the challenge of the new economy regarding education attainment, workforce preparedness, health, life and inclusion. Ricks called on the state legislature and governor to fix the situation. 

In accepting the 2022 Trailblazer award, Oesterle said he disagreed with Ricks on one point: “I think those problems—innovation, efficiency, inclusion—get solved in this room, by you people. It happens here. David Ricks issued us a challenge. I’d like to say to him: ‘We accept.’” 

The 1,000+ TechPoint Mira Awards gala crowd that had sat in strained silence, struggling at times to understand each word, stood and cheered their agreement for several, long minutes in recognition not just for what he said, but in recognition of Oesterle’s commitment to excellence despite his own evident physical challenges. 

WATCH VIDEO: Bill Oesterle accepts the Trailblazer Award during the 2022 TechPoint Mira Awards.

The people Oesterle influenced ranged from people struggling and down on their luck to promising college students to one man who would become governor.  

“I’m not often at a loss for words, but trying to imagine a world without Bill Oesterle leaves me that way. He was a job creator, a community builder, a lifelong advocate for Indiana and a person with an enormous heart for others,” said former Purdue University President and Indiana Governor Mitch Daniels. “He always said I was the person who persuaded him to return to Indiana: If that is so, it’s the single service I’m most proud of.”   

Angie Hicks stands out among the countless people influenced by Oesterle. Together, they built Angie’s List, which would become one of the city’s fastest growing companies and prolific tech employers. 

“Bill was always there to hear me out and to encourage me to keep going. I learned from him every day but probably the most important thing was to invest in people, not things, and to do what you can to help others realize their potential.” 

Hicks said Bill’s legacy as an entrepreneur, leader and champion of Indiana will endure, but even more importantly, “we’ve lost an inspirational mentor who left an impression on so many of us in Indiana and beyond from Angie’s List to the Orr Fellowship to TMap and beyond.” 

Oesterle will be remembered as a tech giant in Indiana, but the company that launched the legacy was not a tech company at all. Angie’s List was initially a newsletter and a printed magazine. It wasn’t until about 2000 that the company launched its first website. 

“But Bill was always an early adopter of tech,” said Jackie Annan, who began as Oesterle’s executive assistant in 2009, left the company with him in 2015, before working with him at Our Health (now Marathon Health) and rejoined him in 2019 at TMap and MakeMyMove.  

“Bill was always an early adopter of tech. He was a prolific user of eBay and Amazon before they became big,” she recalled. “He had us playing with a device called Litl more than a year before a less clunky and more streamlined device called the iPad came out.” 

His knack for finding the next big thing before it was big wasn’t limited to devices and companies, though, she said.

“Bill realized the importance of content before ‘content marketing’ was even a thing,” she said, pointing to the reviews that were the bedrock of Angie’s List and its nationwide magazine. “He looked at things from a user perspective and used tech to deliver what people needed and wanted.” 

In 2011, Chelsea Linder, now a partner at gener8tor, was on an airplane heading home to Boston for winter break. A Butler University senior earning an international business degree at the time, she was mulling over a job offer from Angie’s List when she saw a guy on the plane wearing an Angie’s List-branded shirt. Taking it as a sign from the Universe, she introduced herself, telling the stranger who she was and that she was trying to decide whether to take the job and would he mind telling her a bit about what it was like to work there. 

“Well, I started Angie’s List, and I think you should take the job,” Oesterle responded and then spent a good portion of the flight learning more about Linder. The more he learned, the more he encouraged her to give the job a shot. Linder spent more than six years at Angie’s List and said he was 100 percent right in telling her then that it would give her a chance to define her career and her future. 

“He let the ladder down for so many people who followed his example to let that ladder down for other people,” she said. “So many of us in the tech community learned the importance of being a mentor to others because of Bill who both showed and influenced others to follow his lead in doing that.” 

When she joined gener8tor, Linder said job No. 1 was to build a network of community and business leaders who could mentor startups. 

“All I had to do was go to my Angie’s List Rolodex and ask them to come talk to startups,” she said, rolling off names like Shelly Towns (who began as a staff writer at Angie’s List, left as SVP of Product and is now CMO at Marathon Health), Darin Brown (formerly CTO at Angie’s List, then executive stints at High Alpha and Docket, now Zoom), Chris Campbell (SVP Product & Technology at Angie’s List now a CPO at WorkHuman) and Robin Fleming (SVP Technology at Angie’s List who went on to launch Anvil and hold executive positions at High Alpha, Evolv Tech and others.) 

“It was an easy “yes for them,” Linder said. “We all learned at Angie’s List that that’s just what you do.” 

David Kerr, managing director at Allos Ventures, met Bill at the Hudson Institute, each of them at the beginning of their careers back in the late 1980s. Anxious for excitement, they asked a woman who’d traveled internationally (as neither of them had) what her favorite trip was. Within hours of that conversation, they’d booked one-way tickets to Istanbul and spent 10 days or so traveling through Europe seeing things two Midwestern boys hadn’t envisioned, soaking up the culture and occasionally paying for that with adverse physical reactions. 

“He saw no reason to wait to execute on an idea. He was always just a doer,” said Kerr, who was the fourth investor in Bill’s idea to improve upon Unified Neighbors, a neighborhood-centric newsletter that helped neighbors find service providers. 

Unfortunately, Kerr sold his stake in the company that would become Angie’s List long before the company would expand nationally and then go public. He also spent some time at Angie’s List as general manager of e-commerce. 

Kerr said Oesterle’s legacy covers a lot of ground, but includes the Orr Fellowship and other talent development and retention efforts and the ripple effect from leading a successful company. In places like Silicon Valley, there are hundreds of companies that have launched and gone public.  

“Indianapolis has only a handful of those kinds of companies—companies like Software Artistry, Aprimo, Interactive Intelligence, ExactTarget, Baker Hill and Angie’s List—places that people passed through and took what they learned to help grow the Indiana tech community,” Kerr said. 

Long before Angie’s List went public, Oesterle was talking with potential investors headquartered on the East Coast. They offered a significant amount of funding to the young company but on the condition that Oesterle relocate to “one of the coasts” because in the investors’ opinion, there wasn’t enough talent in Indiana to give the company what it needed to advance to the next level. 

The proposition incensed Oesterle, who declined the offer. It also refueled his zeal to prove to the world that Indiana did, in fact, have the talent it needed. And not just for Angie’s List, but for the tech sector and other sectors as well. 

Kerr and others agree that Oesterle’s evangelistic approach to telling outsiders about the depth of talent in Indiana and his demonstration of that faith in turning down offers that came with too many strings had a positive effect on other tech entrepreneurs’ success in Indiana and in their ability to raise money from investors across the country. 

Ting Gootee, now President and CEO of TechPoint, was the chief investment officer at Elevate Ventures when she came to know Oesterle well. Elevate Ventures invested in TMap and its offshoot, MakeMyMove.  

She had just joined TechPoint last year when a select group began considering who should be the 2022 TechPoint Mira Awards Trailblazer. She said his influence transcended tech. 

“Bill is known to many of us as a successful tech entrepreneur and an influential community leader. He cared deeply and drove relentlessly to create economic opportunities, through building and investing in commercial and social enterprises and through supporting and empowering individuals many of whom are in tech,” she said. “We are honored to remember him as a dynamic tech leader, a Trailblazer Award recipient, and most importantly, a community icon who will have an impact on generations to come.” 

Mark Hill, chairman of Lumavate and co-founder of Baker Hill, a financial tech company acquired by Experian in 2005, worked closely with Oesterle on the RFRA front lines. Hill said he will most remember Oesterle for the passion he brought to that effort and other initiatives. 

“He had such a sense of outrage that Indiana would be a place of discrimination,” Hill said.  

One of Oesterle’s most lasting legacies, Hill said, will be his work to engage, develop and retain talent in the state, including the Orr Fellowship, which Hill helped scale. The organization has 550 alumni, many of whom have gone on to hold executive positions or started their own tech companies. 

“Bill Oesterle’s impact on Indiana, and specifically the tech community, are going to be felt long into the future,” said Orr Fellowship President Steven Emsch. “He set the model for what a leader can and should be. A lot of the characteristics we look for in Fellows were exuded by Bill. Attributes like relentless will, incredible humility, an emphasis on community and people, and, most importantly of all, courage.” 

Hill’s first Orr Fellow hire at Baker Hill was Mike Langellier, who he would later hire to lead TechPoint and who now is an operating partner at High Alpha. Still at the TechPoint helm at the 2022 Mira Awards, he said this about Oesterle:  

“Bill’s career has had many chapters, but a common thread was a vision and conviction for improving Indiana and creating opportunities for Hoosiers. He saw a big opportunity for Angie’s List and grew a market leading company here. He saw the need for transformational state political leadership and championed Mitch Daniels’ election. He saw the need and opportunity to attract and retain talent and instigated the Orr Fellowship and TMap. He saw the intent and impact of RFRA and pushed back. He’s a visionary, and he took risks—both professional and personal—that benefited our community and inspired others, including me.” 

The Oesterle effect wasn’t limited to Indianapolis, though that was his main base of operations. Circa 2017 or 2018, he noticed a reference in an economic essay about population loss in some rural Indiana counties. It alarmed him, but he was more alarmed that few others seemed concerned by it. 

His bid to address it started around 2018 when he enlisted former Angie’s List executives Ed Sherman, Hock and Rutz to help him gather data. Initially, they reached out to the Angie’s List network, giving the same pitch to hundreds of people: “Give us three names of people you know who don’t live in Indiana anymore but would have reason to come back.”

That effort began the database that would power TMap (for Talent Map) and later MakeMyMove, which is currently working with more than two dozen Indiana communities to recruit workers to relocate there. 

Seeing success, Oesterle and crew in 2022 mobilized economic development, community and municipal leaders to successfully lobby for passage of Senate Bill 361, which allows city leaders to secure funding for talent attraction and retention activities through local tax increment financing dollars. IEDC provided $1.5 million in matching funds for Indiana mayors and economic development corporations to bolster their talent recruitment and retention initiatives. The program proved so popular that IEDC added another $1 million to the matching fund element. 

“Bill was an Indianapolis institution. But his presence will be felt all over the state for years,” Hock said. “Look at the talent he imported through Angie’s List and the Orr Fellowship, the inclusive influence he brought to our politics, and remote worker recruitment programs in two dozen Hoosier communities. His legacy will prove to be remarkably durable.” 

Sherman, vice president of community engagement at MakeMyMove, said the effort was just one example of Oesterle’s ability to move beyond mere advocacy to mobilize groups of people to accomplish things. 

“One of the things Bill liked to point out was that he’d come to Indianapolis without any real pedigree but that the tech community welcomed him and allowed him to work on big things,” Sherman said. “He said that kind of welcoming environment set Indiana, and Indianapolis apart, and it was a huge part of what made him champion Indiana.” 

Sherman, himself a transplant, is a Massachusetts native who met Oesterle by working in the Angie’s List sales department. Sherman’s wife was working in Ohio in the early days of the business, so Oesterle offered to let him stay through the week at his house. They developed a deep friendship in addition to becoming business partners. 

“Bill cared about people. Plain and simple, he cared about people, and he worked to make sure they knew they were important and had a part to play in the world around them, whether it was a bar full of people or a boardroom full of corporate executives or political leaders,” Sherman said. “He often saw your potential before you did, and then it was off to the races.” 

Annan agreed.

“Bill taught me so much about trust. From the very beginning, he literally trusted me with his life, his family, his businesses,” she said. “He trusted me in a way that I had never trusted in myself. He believed I could do anything. He loved to give people more responsibility than they knew they were capable of. His super power was the empowerment of others. Every time I heard an outlandish request that seemed impossible, he proved me wrong. I just needed to trust and believe in myself as much as he believed in me.”  

Like hundreds of others who caught the entrepreneurship bug from Oesterle, Annan, her husband and a business partner recently launched their own commercial and residential real estate business. 

“Working with Bill was my own personal Master Class in entrepreneurship, kindness and believing in yourself,” she said.