Building a community of tech entrepreneurs: Looking back at 15 years of Philly Startup Leaders

For 2008, the idea was novel. A social group for harried founders to commiserate and bond? Someone trying to start a venture in Philly today would have dozens of options. A decade and a half ago, the opposite was true. Philly itself wasn’t yet a hotbed of activity. In fact, if you were working on a tech startup, you were more likely in the suburbs.

Then came the Great Recession. Throughout the 2010s, civic boosters around the country sought new economic development strategies, often trying to attract to their cities the big wave of millennials deciding where to plant roots. Philadelphia was finally doing better at retaining area college graduates, but high-growth entrepreneurship was still heavily concentrated elsewhere: Silicon Valley, New York, Boston.

Enter Philly Startup Leaders, aka PSL. Over the years it has grown into a place for local entrepreneurs to find each other. In other cities, these efforts are often attached to big public-private organizations, but PSL is a small independent nonprofit.

The work hasn’t been easy, especially as the pandemic forced a comprehensive rethinking of programming: annual revenue plunged 66%.

But PSL is still here. Last fall, it held a series of events to recognize its 15-year anniversary. These included Founder Factory, a conference offering advice to local entrepreneurs, and a screening of the 10-year-old “Developing Philly” documentary series featuring a discussion with the filmmakers. The main event was December’s shiny Glassbreakers Ball, reuniting the original six founders, recognizing them with awards onstage.

PSL has lasted through different leaders and organizational structures. But the idea of community and bringing startup founders together has remained.

So what role does the nonprofit take into its next 15 years?

The landscape has changed. For most of PSL’s history, Americans were starting fewer and fewer businesses. Ultra-low interest rates, cheap software and Silicon Valley culture fueled the exception: tiny tech startups with a chance at outsized growth. Incubating that gave PSL its first identity. Now, business starts are booming, but they look different: outside capital is harder to get, entrepreneurship is more diverse and remote teams proliferate.

PSL leadership says the organization is focused on working with local and national partners, and bringing more accessibility and equity to the startup community in Philly.

“The fact that this organization is sustainable, I think, says a lot about Philadelphia,” Tracey Welson-Rossman, one of the founders of PSL who is now CMO at Chariot Solutions and founder of Journal My Health, told Technical.ly.

“You know, gritty, authentic … not really good at promoting ourselves as a community. But I think the reason that this is still around is because of who we are as Philadelphia.”

Bringing startup action into the city

Looking back at the 2000s, tech startup activity was concentrated in the Philly suburbs. The founding of PSL played a big role in shifting the sector’s center to the city proper.

At its early-2000 peak, software star VerticalNet, based in suburban Horsham, was perhaps Philadelphia’s first tech unicorn: valued at $12 billion, on very little revenue. A year later, it laid off a quarter of its staff and was gasping for an infusion of cash from Microsoft. It never recovered.

Its collapse might be the best local example of the dot-com bubble bursting, after a decade of explosive growth in home computers and internet usage. During the 1990s boom, the region developed a respectable reputation as an IT hub — in 1985, then-President Ronald Reagan called it the “Silicon Valley of the East.” Just about everything happening was suburban, especially along Montgomery County’s Route 101. Embattled venture firm Safeguard Scientifics was once the icon, surrounded by successive waves of successes, such as Infonautics, Bluestone, CDNow, Half.com, GSI Commerce and Verticalnet.

After the dot-com bubble burst, though, Philadelphia expats returned home from Silicon Valley, and Philadelphia’s earliest tech meetup and first coworking community took root in Center City, where transit and culture contributed a shared identity. Online ticketing company Ticketleap launched as one of Philly’s first true city-based tech startups in 2003. Meanwhile, Comcast was quietly becoming a category-defining telecommunications giant, while Philly-HQ’d Ben Franklin Technology Partners had been investing in early-stage tech companies for 25 years.

Still, outside an occasional event, very little activity was happening in the city.

Blake Jennelle wanted to change that. In the fall of 2007, he was trying to launch a software startup and he started hosting happy hours for startup founders because he had a hard time finding fellow entrepreneurs.

“It was basically trying to find the, at that time, very isolated founders of technology startups that were in Philadelphia, and there was no community or ecosystem,” said Jennelle, who is now CTO at New York- and San Francisco-based 645 Ventures. “The first job at Philly Startup Leaders was just to assemble these people together and help people get to know each other.”

He organized an event in January 2008 for all the people who had been coming to the happy hours with a goal to establish a formal group with a mission.

“That was the official founding moment in my eyes,” he said. The group formally incorporated as a nonprofit in 2016, per Isabelle Kent, PSL’s current CEO.

Before PSL, the local community of startup founders was geared more towards experienced entrepreneurs, said cofounder Doug Bellenger, now CEO of Ambler’s Well-Crafted Beer. At the time he was the founder of software startup PhindMe, an early mobile startup. Comcast wasn’t quite as influential a civic and recruiting presence, and the universities weren’t contributing to the startup ecosystem the way they are now, he said.

Likewise, few true tech firms in the region had reached real scale — no Gopuff, no dbt Labs, no Phenom and a still-upstart DuckDuckGo. Part of PSL’s role was to create a community of entrepreneurs that made Philadelphia a place where founders wanted to stay and grow their companies.

PSL’s founders continued hosting monthly happy hours. They also introduced events like Founder Factory, where people gathered to learn from experts and investors and connect with each other; the Entrepreneur Expo startup showcase; and “fishbowls,” where entrepreneurs could present challenges they were facing and receive advice. (A year-old Technical.ly got its own fishbowl with the group back in 2010, and the Entrepreneur Expo became an annual anchor of Philly Tech Week.)

PSL “was like a startup of startups — it was a bunch of us trying to figure [it] out and fail fast and understand things,” Bellenger said. “But then at the same time, we were also trying to run our own business.”

‘We had to actually represent the city that we were in’

Over the years, the org has seen highs and lows in activity, said Bob Moore, now CEO and cofounder of Crossbeam, who served as president of the PSL board from 2017 to 2019.

“PSL has always gone through these cycles,” Moore said, “where great leaders come in and spend a lot of time and investment and focus on the organization and do their best to kind of level it up in various ways.”

As early as 2011, the org’s volunteer organizers had an “identity crisis.” That December, those mostly first-time founders announced their new volunteer leader: the seasoned and respected tech CEO Bob Moul, who was fresh off leading one of the largest tech exits in Philadelphia history.

Moul is credited with moving the organization into a period of growth, according to Moore. He got PSL more involved with city government, especially the mayor’s office (via later board member Luke Butler), as well as with the broader nonprofit sector. Moul and PSL influenced then-Mayor Michael Nutter’s launch of StartupPHL, the city government’s first tech and entrepreneurship strategy.

This resulted in more brand recognition and credibility. Moore began to feel like PSL’s work mattered more, knowing that city government and the mayor cared about the startup community and helped make it easier for companies to succeed.

By 2016, PSL organizers had raised enough money in sponsorships to hire paid staff, relying less on volunteer time from local entrepreneurs. Programming became more polished and visible, timed with growing post-Great Recession interest in entrepreneurship. As PSL’s access and activity reached a new peak, it encountered growing pains. By 2017, the group’s young and ambitious first staff member had been promoted to executive director — and faced stinging criticism for early diversity initiatives. After a combative panel at a local conference, she stepped down, ushering in another period of org reevaluation.

In response, Moore, by then one of the region’s best-respected tech founders, stepped in as board president, and recruited a revamped board.

“If we wanted to have that high profile, if we wanted to matter at the level that we were on the radar of being representative of the city,” Moore said, “then we had to actually represent the city that we were in.”

They recruited City Fit Girls (now Strides) cofounder Kiera Smalls as executive director, and she led PSL from 2018 to 2020. Smalls and the Moore-led board introduced new governance and org structure, hiring other support staff and revamping programing, including the city’s only general tech startup accelerator.

Moore remembers the latter half of the 2010s as being an especially active events period, featuring some of the most vibrant Entrepreneurship Expos, with hundreds of attendees and dozens of startups in attendance.

“Feeling how alive that community was in those areas of holding those events and bringing everybody together was just really, really, really great and important,” he said.

Keeping community when live events disappeared

The organization came to an inflection point in 2020.

Kiera Smalls left PSL that summer, soon after rallying the local tech community to raise $550,000 to grant to underrepresented founders, an initiative she spearheaded amid nationwide protests against systemic racism.

In March 2021, the board hired Isabelle Kent, who had a background in recruiting and marketing, as its next executive director. Kent remembers receiving a lot of support from past PSL leadership, and said she’s now focused on paying it forward to the next generation.

As she took over, the once events-heavy organization was dealing with the pandemic-forced world of going virtual. As a result, the team had to reevaluate who their audience was, what Philly entrepreneurs were expecting from PSL, and if those things had changed.

“Overwhelmingly what we were asked for the most was that people just needed community,” Kent said. “They needed to go back to a place where they were around other people that had similar perspectives, that were doing the same thing, that were going through the same challenges and have a safe space where they can have those discussions.”

And PSL provided that, offering at least some sense of community and stability to local founders during an extremely disconnected and uncertain time, according to Rudy Ellis, another startup founder who became board president in 2021.

The money wasn’t as easy to translate. PSL’s funding had traditionally relied on event sponsorships, plus charitable donations from companies and entrepreneurs that back its work. Several of those donors kept their commitments as events were sidelined by the pandemic, but other a lot of funding dried up. In 2020, the organization reported $553,000 in income, versus $630,000 the year prior, according to the nonprofit’s 990 form. That fell as low as $208,000 in 2022.

“In many ways, that’s made us much more empathetic,” current CEO Kent said, of the pandemic challenges, “and now we’ve also been able to open up the floor for much more trust-based conversations and have a certain level of transparency when we talk about these issues.”

Finding place and purpose in a now-vibrant ecosystem

Much has changed in the last 15 years. Entrepreneurship is booming, and more industries leverage software and data science than just traditional IT.

Though the pandemic disrupted much of it, far more founder-focused programming takes place in the city today than in years past — see a revival of tech meetup culture, no-longer-suburban-dominated PACT and the Philadelphia Commerce Department’s Tech Talks. Most universities, affinity chambers and other economic development groups are also investing in startup strategies. Comcast’s LIFT Labs has a robust entrepreneurial engagement strategy, and the Coded by Kids-spinout 1Philadelphia is evolving into a comprehensive inclusive innovation clearinghouse.

PSL’s challenge now is fitting into a far more vibrant ecosystem than at its origins.

The org published in September 2021 a five-year plan for itself focused on connection and equity. It’s currently working on streamlining internal processes, and plans to release an updated mission in the next year with a focus on serving entrepreneurs, according to Kent.

As CEO, Kent sees PSL becoming a “connector, convener, navigator” for the Philly startup ecosystem, and possibly expanding outside the region. The organization is looking to work with more local and national partners to deliver leadership development programming for founders, such as early-stage startup accelerator Founder Institute. PSL collaborated with FI for a crossover accelerator last fall instead of running its usual Founded in Philly accelerator, and PSL is a collaborative partner with FI’s Philly chapter.

“Now we’re moving in the direction of having a new brand vision, a new five year strategy, and continuing to act on, kind of, these two levels,” Kent told Technical.ly. “One is serving our founders first and foremost. But then part of our other mission, in our core value set, is that we continue to do so in a way that is promoting positive recognition for Philly startup ecosystem, and doing so in a way that Philadelphians can participate equitably.”

According to PSL leadership, their strategy for doing this is to return to the org’s roots: Bring back flagship events such as Founder Factory, engage former leaders as advisors, and focus on the volunteer- and community-focused aspects.

Part of this strategy includes Legacy Leaders Council, a group of PSL’s earliest supporters launched in summer 2023 to advise current leadership. Former PSL board member Gloria Bell, who now runs the Women in Tech Summit, is chairperson of the council.

“We’re getting to provide an opportunity for a lot of those people who were part of PSL in those early days,” Bell said, “to be able to reconnect and be involved again and have an opportunity to give back to the organization.”

An organization that lasts

None of the original founders of PSL are involved in the organization’s daily leadership anymore, although Bellenger and Chris Cera, PSL founder and now CEO of Arcweb Technologies, serve on the Legacy Leaders Council.

But Bellenger thinks that’s the point: They intentionally designed Philly Startup Leaders so it could continue to run without them.

They all got involved with PSL because they were all genuinely interested in making their community better, said Aaron McLean, now chief of staff and CxO at Stuzo and a founder of PSL. And they welcomed anyone to join the group because they thought everyone could bring something valuable, Welson-Rossman added.

“One of the things that I’m really proud of us for is the way that we set up succession,” cofounder Jennelle said. “It wasn’t really about us, right? It was like, how can we build an organization that belongs to the community?”

Sarah Huffman is a 2022-2024 corps member for Report for America, an initiative of The Groundtruth Project that pairs young journalists with local newsrooms. This position is supported by the Lenfest Institute for Journalism.