The People Who Make Boston Wicked
From Fenway to the Financial District, from food trucks to corner offices — the untold stories behind the people who make up the fabric of this city.
Episode 13 - Karen Smyers - Ironman World Champion
In 1999, Karen Smyers raced the Ironman World Championship in Kona knowing she probably had thyroid cancer. She finished second. Then she went and got the biopsy.
Karen won Kona in 1995, in only her third Ironman, and won the ITU World Championship that same year; she’s still the only woman to do both in one season. She was in the first class of the USA Triathlon Hall of Fame in 2009, and this October she went into the Ironman Hall of Fame, news Bob Babbitt sprang on her in the middle of an interview.
We talk about the storm window that cut through her hamstring the day before a flight to Monte Carlo, the truck that hit her on her bike, the poppy seed bread that got her flagged for morphine, and the 3-2-1 beer taper people still quote back to her 30 years later. She also talks about the heart condition that kept her from racing for years, and the new medication that has her planning a comeback at 65. In her words: “Look out, older women, I’m coming.”
Stay Wicked Boston!
Melissa Stern never went to design school. She wore a homemade sequin jacket to the Nantucket Wine Festival, people kept asking where she bought it, and she started a brand.
Today Mel the Clothing is sold at the Red Sox Team Store, TD Garden and team shops in Miami, Carolina and New York. Nikki Glaser has worn it on tour, and Tom Brady’s family has worn it too. One of Mel’s pieces ended up on national TV next to Taylor Swift, and Mel found out the same way everyone else did: watching from her couch.
Mel talks about how an independent designer gets into pro team stores, what happens when bigger companies copy your work, and why she won’t raise her prices even when a single piece takes 17 hours to rhinestone.
Stay Wicked Boston!
19 Oct 2026
Episode 11 - Nick "Fitzy" Stevens - Content Creator, Comedian, Boston Sports Icon
Fitzy is one of the loudest sports fans in New England, and he doesn’t technically exist. Nick Stevens built the character on stage in New York; YouTube took it from 300 views a video to 50,000, the Patriots hired him to host their rallies, and WEEI kept him on the air for seven years. Then, this spring, the radio job ended.
I wanted to know what it takes to build a business on a character, and what’s left when the job goes away. We get into his ESPN Dream Job run, riding a duck boat in the Super Bowl LIII parade, the on-air blowup with Ted Johnson he still won’t apologize for, and the night Tom Brady’s dad looked at him and said, “We’re not worthy.”
I asked for Nick. Fitzy showed up anyway.
13 Oct 2026
Episode 10 - Jayme Parker, Creator, Executive Producer & Host of "Outside the Fame" on NESN
Red Auerbach wouldn’t let her into the Celtics locker room. Shaquille O'Neal patted her on the head in front of a room full of reporters. A puck hit her in the shoulder the night she worked the Bruins PA mic. She’s still here, and she’s still not impressed with herself.
Jayme Parker has covered the Celtics, Red Sox, Bruins, and BC since the ’90s, from NESN’s Sports Desk to the sidelines, and became the first woman on the Bruins PA mic. Eight years ago she left NESN to create, produce, and host Outside the Fame, where athletes show her the parts of their lives nobody sees. This year she’s also teaching a grad class at Boston College.
I ask her about fighting her way into her first locker room, her friendship with Tim Wakefield, finding a sponsor for every single episode, and why she still does her research with a notebook and a pen.
Stay Wicked, Boston.
6 Oct 2026
Episode 9 -Anna Johannes - 2012 Paralympic Bronze Medalist
Anna Johannes won a Paralympic bronze medal for Team USA in 2012. Then she spent eight years in corporate marketing being told not to bring up her disability.
She was born without her left hand and forearm in Kyrgyzstan and adopted at two. She went on to win five golds at the 2011 Parapan American Games and a bronze at the 2012 London Paralympics. After swimming she worked in marketing at Speedo, Boston Children's Hospital, Porter Novelli and Interbrand. In 2025 she left to start On the One Hand, a disability storytelling consultancy, and she's now part of Culxtured, a media collective run by Paralympians.
The part I keep coming back to is how she sees media coverage of disabled athletes. She says it's usually about inspiration and charity, and she'd rather it be about the training and the competitiveness. In other words, cover them like athletes.
We also get into losing by hundredths of a second, why corporate inclusion work went quiet, and how a blind swimmer knows where the wall is.
Follow Anna on Instagram: @anna_f_johannes
28 Sept 2026
Episode 8 - Todd Angilly - Boston Bruins National Anthem Singer
Todd Angilly was pouring beers inside the Garden when eight Boston cops pulled him off the bar, threw a Bruins jacket over his uniform, and sent him out on the ice to sing the anthem with 15 minutes' notice.
Todd has been the Bruins' national anthem singer since 2019, following Rene Rancourt's 42-year run. Before that, he was an opera student who kept getting rejected, then a line cook at Fenway, then a probation officer. His day job is still helping people coming out of prison find work. We talk about the call-up, singing the first Red Sox game after 9/11, his dad's post-game phone calls, and why he insists it's never about him.
Stay Wicked Boston!
22 Sept 2026
Episode 7 - Doug Smith, "The Goon"
This week I sit down with Doug Smith, a guy from the South Shore who started out as a boxer, could barely skate, and still talked his way into a decade of minor league hockey as an enforcer. His job was simple and not at all easy: protect his teammates and drop the gloves when it counted.
Doug co-wrote Goon with Adam Frattasio, and that book became the 2011 cult-classic film, followed by a sequel. Since 1999 he's been a police officer in Hanson, which might be the only second career that makes more sense for him than the first.
We get into what it actually takes to fight for a living, what the movie got right and what it didn't, the physical toll nobody sees on the highlight reel, and why a guy known for his fists turns out to be one of the more thoughtful people I've had in the chair.
Doug also tells the story of donating a kidney to his co-author's brother, which says more about him than any fight ever could.
Stay Wicked Boston!
15 Sept 2026
Episode 6 - Mark Ockerbloom, Boston 25 News
If you've watched the news in this city at any point in the last 20 years, you know the face and the voice. Mark Ockerbloom anchored at Boston 25 for 22 years and signed off this past May. That's 40 years in the business. He's still not sure "retired" is the right word for it.
I hope you enjoy this episode as much as I did. Mark is a treasure to the City of Boston.
8 Sept 2026
Episode 5 - Kerry Kavanaugh, Boston 25 News
Kerry Kavanaugh anchors at Boston 25 News and leads their investigative unit. She's from Medford, went to BC, and got exactly one callback out of the 80-odd VHS resume tapes she mailed around the country — from a one-person bureau in Montana. She took it sight unseen.
We talk about the road back to Boston through Des Moines, Tampa and Atlanta, and about covering Sandy Hook and the Marathon bombing, which she says stay with you. She explains why she keeps pulling threads on stories most reporters file and forget, including a domestic violence job-protection loophole that still hasn't been closed. She also talks about going public with IVF in 2018 and a hysterectomy this past spring, and why she thinks women's health is still under-discussed. We finish on the shrinking of local news and what's lost when nobody's covering the town hall meeting.
Stay wicked, Boston.
1 Sept 2026
Episode 4 - Mark Riley Comedian, Chirping Zebras Podcast Host
What do you get when a hockey referee gets fired by the NHL after just one week and channels it into a 26-year stand-up comedy career? You get Mark Riley.
Mark is one of New England's most booked comedians, a former professional referee, screenwriter, and co-host of the podcast Chirping Zebras — hockey from a ref's perspective. In this episode we cover it all: his path from Curry College hockey to the NHL (briefly), why he thinks being American cost him the job, how a bad night at Nick's Comedy Stop — the night before his daughter was born — became a turning point, and why he believes youth sports specialization has become an epidemic.
We also get into Chirping Zebras, his unfinished book, his screenplay Penalty Box, and his rapid-fire takes on instant replay, hecklers, and showering with Zdeno Chara.
🎤 http://markrileycomedy.com (http://markrileycomedy.com) | 🏒 http://chirpingzebras.com (http://chirpingzebras.com)
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#WickedBusinessBoston #MarkRiley #ChirpingZebras #BostonComedy #HockeyReferee #StandUpComedy #BostonPodcast
25 Aug 2026
Episode 3 - Brian Daly, "Is it a Seger Bar?"
Brian Daly is why every bar in Boston is either terrified or thrilled to see him walk in.
He started out filming skateboarding videos with his friends around Boston, which somehow turned into content work for Red Bull and Puma. These days he's the Director of Social Media at Jeffrey Glassman Injury Lawyers — bringing a skate videographer's eye to personal injury marketing, which is a sentence that shouldn't make sense but does.
Then there's the other thing he's known for: walking into random Boston bars and asking bartenders one question — will you play Bob Seger? The ones who say yes without hesitation get "Certified." The series blew up, landed him in the Boston Globe, got him on air with WZLX, and even got a Seger Bar stamp of approval from the Governor of Massachusetts.
Brian's back on Wicked Business Boston — this time on camera — to talk about the actual arc: skate videos to brand work to legal marketing to accidentally becoming Boston's unofficial Bob Seger ambassador. We get into how he built an audience, what he's learned working both sides of content (his own and a law firm's), and what's next for the Seger Bar.
🎥 Watch, laugh, and if your local bar hasn't been Certified yet — you know what to do.
#WickedBusinessBoston #Boston #BobSeger #ContentCreator #IsItASegerBar
3 Aug 2026
Episode 2 - Johnny Hilbrant, "PE Guy"
My guest this week is Johnny Hilbrant — creator of "PE Guy," on social media, the private equity parody character with hundreds of thousands of followers online. We talk about how a Boston fitness instructor built a viral character from a wedding conversation he couldn't escape, and what happens once the internet actually notices you.
29 Jul 2026
Episode 1 - Becca Pizzi
Becca Pizzi, a lifelong runner, shares her incredible journey, experiences, and challenges as a marathon runner, race director, and coach. From her love for running to her dedication to the Boston Marathon and her participation in the World Marathon Challenge, Becca's story is one of passion, resilience, and inspiration. Becca Pizzi shares her experiences as a race director in Antarctica, the challenges of running in extreme conditions, her achievements in marathon running, and the impact of her family and community involvement. She also discusses her foundation, book, "Becca's Feat on Feet."
Takeaways
Passion for running drives lifelong dedication
Overcoming adversity and injury with determination Running in extreme conditions requires specialized gear for protection.
Support from family and community is crucial for endurance athletes.
Community involvement and giving back are important aspects of Becca's life.
Chapters
00:00 The Journey of a Lifelong Runner
03:01 The Boston Marathon Experience
05:08 Overcoming Injury and Adversity
09:00 Running Around the World
11:56 The World Marathon Challenge
16:59 Race Directing and Coaching
21:16 Race Director in Antarctica
21:53 Running Gear for Antarctica
22:40 Polar Bears and Safety Measures
23:12 Running the North Pole Marathon
25:02 Support from Spouse
25:59 Coaching and Family
27:20 World Records and Aging as an Athlete
30:37 Quality Over Quantity in Training
31:48 Life in Antarctica
33:12 Mount Everest and Endurance Challenges
34:13 Becca Pizzi Foundation and Book
39:16 Community Events and Scottish Influence
41:50 Daughter's Perspective
Reach and audience
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Apple Podcasts (US)
5.0 / 5
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