The Book Lisp with Jon Ryan & Sarah Colonna

Episode: "Side Hustle and Comedy Bustle"

Date: January 5, 2026
Hosts: Jon Ryan & Sarah Colonna

Overview

In this episode, Jon and Sarah kick off the new year with a hilarious, candid conversation about their early side hustles and the struggles of making it in entertainment. Using their January book pick, Summer Island by Kristin Hannah, as a jumping-off point—about a struggling comedian and her estranged, radio-host mother—the hosts swap stories about hustling to make ends meet, performing comedy under humiliating circumstances, and the hustle every performer faces coming up in Los Angeles. The episode is both a journey through their personal histories and a peek behind-the-scenes at the realities of chasing creative dreams, full of comic mishaps, nostalgia, and doses of tough love.

Key Discussion Points & Insights

1. Book Club Updates & Housekeeping

[00:08–02:43]

• The Book Lisp's book for January: Summer Island by Kristin Hannah.
• Patreon provides short story discussion ("The Body" by Daniel Hurst this month), with bonus episodes and a vibrant Facebook group for listeners.
• Sarah plugs her upcoming tour dates; listeners encouraged to check her site for full details.

2. Introduction to This Month’s Book

[04:16–05:14]

• Jon picked Summer Island blind—hasn’t read it yet but is reading slowly to keep details fresh.
• The novel centers on an estranged mother-daughter pair: the mother, a popular Seattle radio host; the daughter, a struggling comedian in LA.

3. Early Side Hustles – The Reality of Starting Out

[05:15–14:40]

Jon’s Side Hustles:

• As a Canadian unable to work legally in the U.S., Jon relied on unusual jobs:
  • Selling fake designer jeans:
    • “I used to buy a bunch of fake sevens. Like knockoff sevens. And then I'd sell them on ebay and on Craigslist in Portland. And I would definitely advertise them as they were real, they were authentic.” (Jon, 07:47)
    • Only caught once, quickly refunded the buyer.
  • Breaking up and reselling toolkits:
    • Bought bulk tool sets from a Sears outlet, split them up, and resold at a profit to pay rent in college.
    • “Our whole pantry wasn't full of food. It was just full of tools.” (Jon, 10:29)
  • Flipping Baby Phat clothing:
    • Bought in bulk, sold trendy capris at a markup.
  • ‘Nordstrom Last Chance’ resale mission:
    • Hunted returned designer goods at the infamous Phoenix clearance store, waking early to line up with other bargain hunters.
    • “It's Hunger Games up in that.” (Jon, 13:48)

Sarah’s Side Hustles:

• Mystery calling for hotels:
  • Secret-shopped luxury hotel phone etiquette while sweating in her un-airconditioned LA apartment.
• Camel cigarettes promo girl:
  • “We went to set bars and handed out Camel cigarettes… we would give you a free pack of cigarettes.” (Sarah, 16:45)
  • Now completely illegal and frowned upon, but then a means to an end.
• Bar gigs and dive bar performances:
  • Saw the darkest sides of the Valley's nightlife, handing out promo items for cash.

4. “The LA Hustle” – Breaking into Stand-up & Show Biz

[22:27–41:06]

The Struggle:

• Both empathize with Summer Island’s protagonist’s grind in LA.
• Sarah faced humiliating, demoralizing early days performing:
  • Laugh Factory Open Mic:
    • "You had to line up all day… If you had to pee, had to get something to eat, you lost your place in line. And they only allowed a certain amount of people standing in line to get on stage." (Sarah, 24:11)
    • Accused of stealing jokes just for taking notes.
    • Reflects on the blend of protection and paranoia in comedy venues.
  • Random “Gigs”:
    • E.g., booked at a Starbucks, told “there’s an amp in the back… do your thing.” Customers baffled and leaving as Sarah and Chelsea Handler did standup to utter indifference.
    • “I think I've got us secured a spot at the Jamba Juice next week.” (Chelsea to Sarah, 31:09)
• The gap between humble beginnings and later success:
  • “You went from two people at Starbucks to 18,000 at Bridgestone arena in Nashville.” (Jon, 32:00)

Comedy Club Culture:

• Stand-up in LA is notoriously tough—a surprisingly hostile place for newcomers.
  • Traditional clubs (Improv, Comedy Store, Laugh Factory) offered little stage time.
• Importance of building your own opportunities (stand-up, improv) just to get seen.
  • “I always wanted to do stand up… oh, this is a way for you to kind of build your own thing and not be just another person in the audition room.” (Sarah, 35:25)
• Reality of representation in Hollywood:
  • Signed with big agency after a hot showcase but dropped when “I didn’t take off when they thought I should.” (Sarah, 34:25)

Navigating LA’s Competitive Scene:

• Jon marvels: “Actors, comedians, whatever. They booked a one way flight out here… This city eats you up.” (Jon, 34:47)
• Sarah: “I realized… stand up was a way for me to try to set myself. It helped a lot for commercials, for sure. It obviously got me Chelsea lately.” (Sarah, 35:25)

5. Stand-Up, Chelsea Lately, and The Evolution of the Scene

[39:44–41:55]

• Sarah attributes her enduring career (and opportunities like Chelsea Lately) to grueling years hustling in LA.

• Discussing Chelsea Lately’s legacy for supporting comics:

  • Jon: “Every night it was a celebration of comedians and they had a place to plug their stuff… We don’t have that anymore at all.” (40:10)
  • Sarah: “She doesn’t get enough credit for what she did for comedians...” (40:36)
  • “It’s been off the air for a decade and still people come up daily and talk about how much they miss that show…” (Jon, 40:54)

• Reflection on other comic showcases (Comics Unleashed) and how their “cheesy setups” nevertheless gave comics a spotlight.

6. Memorable Quotes & Moments

• “You're not even in the center yet. Your eyes are watering, but you haven't eaten it all yet. Keep chopping, girl.” – Jon on surprise layers of marriage and sharing stories (14:41)
• “And then I just never forget. I got home that night and Chelsea wrote me, and she said, I think I've got us secured a spot at the Jamba Juice next week.” – Sarah [30:54]
• On LA dreams:
  • “I am the lead play in every freaking play in my high school in Clinton, Iowa... You move up to LA, you realize that you're like 1 millionth for the fricking Sprint commercial.” – Jon [34:52]
• On showbiz heartbreak:
  • “I got signed with a big agency... and they dropped me pretty quickly. Because I didn't take off when they thought I should.” – Sarah [34:25]

7. Final Notes & Sign-off

[42:08–42:50]

• Sarah and Jon express gratitude for the Book Lisp community in its second year.
• Tease next episode’s topic: life as a radio host.
• “Our podcast can almost walk, eat solid foods!” (Jon, 42:37)

Timestamps for Notable Segments

• Jon’s counterfeit jeans side hustle: 07:47–08:59
• The Nordstrom 'Last Chance' legend: 11:44–13:48
• Sarah’s Camel cigarettes promo gig: 16:45–18:05
• The humiliating Starbucks “gig” with Chelsea Handler: 29:53–31:09
• The struggle at the Laugh Factory open mic: 24:11–26:22
• The evolution from open mic pain to Mohegan Sun: 31:58–32:16, 32:44
• Discussion of Chelsea Lately’s impact: 40:10–40:54

Conclusion

“Side Hustle and Comedy Bustle” is a candid, laugh-out-loud episode that traces the scrappy roots shared by anyone pursuing a creative dream. Jon’s bootleg-Seven jeans empire and Sarah’s cigarette-promoting days offer a resonant parallel to the main character in this month’s Summer Island: the relentless hustle, the mortifying gigs, and, eventually, the payoffs. If you’ve ever wondered about the grind behind the punchlines, or just love to hear two married friends riff about their pathway from side hustle to the spotlight, this episode is unmissable.

For more, join the Book Lisp Spinners on Facebook, and be sure to catch Sarah on her 2026 tour.