About
Drew Chapin is the founder of The Discoverability Company, a discoverability partner for individuals and businesses based in Philadelphia, with nearly two decades of go-to-market experience across Microsoft, Jomboy Media, Perplexity, and venture-backed startups.
He sits on the conference steering committee, presented "Reclaiming Your Online Footprint" at the inaugural 2024 conference, moderated the 2025 "Restoration Through Community" panel, and moderated the 2026 featured panel on rebuilding a career after a justice journey.
Elsewhere on this story
- Drew Chapin's own episode of Nightmare Success Nightmare Success episode: Drew Chapin, Startup CEO to Federal Case
- Second acts, with Jeff Grant, Drew Chapin and Brent Cassity Nightmare Success episode: Jeff Grant, The Federal Expungement Process
At the White Collar Conference
Drew Chapin moderated the panel and opened with his own story as a former San Francisco startup founder. He said the step that set his course after prison was putting the conviction on his resume in plain language, and he asked the panelists about the first people who said yes to them, disclosing a record at work and advice for the newly indicted. His own advice for someone just charged was to find community and get involved in the White Collar Support Group.
“I'm a former San Francisco startup founder who took Fake It Till You Make It all the way to federal prison.”
Watch at 1:07
“The first step that really led me to where I am today, is when I decided that I would just radically own it.”
Watch at 2:48
“Find your community, talk to people who've walked that path, get involved in the White Collar Support Group.”
Watch at 31:59
Chapters
- 0:00 Panel opening and format
- 1:07 Drew on his startup failure and owning it
- 3:55 Rashmi's path from honors student to prison
- 10:33 Desmond at the railroad tracks
- 16:52 Who first said yes after the conviction
- 19:43 Desmond on humanizing language
- 24:58 Rashmi on disclosing your past at work
- 28:21 Desmond on Clean Slate and record clearing
- 30:55 Advice for someone newly indicted
- 34:59 Desmond on embracing pain and passing it on
- 38:34 How to reach the panelists
With Rashmi Airan and Desmond Meade
Drew Chapin moderated the panel, framing restoration as the journey back to family, work and self, and asked each panelist how a community builds the trust people need before they will accept help.
“What we're talking about is the journey back, back to our families, to society, to the workforce, and really back to self.”
Watch at 0:10
“Restoration and second chances really start with connection.”
Watch at 34:47
Chapters
- 0:00 Drew Chapin introduces the panel
- 3:09 Pamela Winn on going from surviving to fighting
- 6:49 Gina Pendergraph on why she always picks up the phone
- 8:33 Michael Gaines on pride and asking for help
- 11:00 Building trust in a support community
- 16:58 Pamela Winn on RestoreHER and the First Step Act
- 22:06 The Women's Care Act
- 25:58 Gina Pendergraph on staying connected to people inside
- 29:55 Hopes for the next ten years
With Pamela Winn, Michael Gaines and Gina Pendergraph
Drew Chapin explained how his search results changed after his own case and how he applied his career in digital marketing to reclaiming them himself. He shared three tips: build up profiles and a personal website you control, ask legal research sites to de-index court records, and request removal from news outlets through their proper channels.
“Social media profiles are some of your best friends as it relates to your online reputation.”
Watch at 1:44
“Since these websites exist to help as a legal research tool, they're generally amicable to removing these cases from search engines.”
Watch at 3:37
“Go through the proper channels and ask nicely. Cannot hurt to ask.”
Watch at 4:22
Shared the stage
Join us in fall 2027.
The fourth annual White Collar Conference is planned for fall 2027, virtual on Zoom and open to all.