Pretty Funny Business

EMMIE Collective
  • 5.0 (7)
  • Business
  • Updated Semiweekly

Introducing « Pretty Funny Business », the playground brand we were forced to create in order to corral our founders’ nonsensical ideas and general tomfoolery. From the founders of, by not generally endorsed by, Emmie Collective. Hosted by Lauren Aquilino and Sydney Mulligan. You can expect off-the-cuff banter on feminism, funny business, and well.. not-so-funny business. Join us out of curiosity, stay for the hot takes and dad jokes. www.prettyfunnybusiness.com

  1. 6d ago

    Is He Trash? Vol. 2: Alexander DeMoulin Defends Himself

    Alexander DeMoulin got fired from two sales jobs, moved into his mom's unfinished basement in Portland, and somehow ended up giving a conference talk called “Are You Trash?” So obviously we had to have him on for Vol. 2. Alexander is Director of Revenue Operations at Fin (formerly Intercom, now officially a Salesforce company — the acquisition was announced three weeks before we recorded this). He's also an EMMIE client, which he'll tell you he became not because of a pitch deck but because he thought Lauren and Sydney were funny, DM'd them for a replacement MQL t-shirt from the first-ever MOps-Apalooza, and ended up in a full vendor evaluation. We talk about the ongoing branded-swag challenge no vendor has fully won (Clay came closest with a leotard, though it was not the thong that was requested), the case for vibe-coding your own martech stack versus paying people who actually maintain it, and the two sales jobs Alexander got fired from before he found his way into ops — the story that eventually became the “Are You Trash?” talk that partly inspired this whole series. Also this episode: The correct pronunciation of “DeMoulin” involves a 1914 Supreme Court intellectual property case and marching band uniformsWhy “Alexander,” “Alex,” and “Alec” caused a full identity crisis at a work eventThe Slack channel names that make the MQL pipeline sound like a girl groupWhat “Stressica Jessica” and “Thirstina Aguilera” have to do with lead scoringThe actual reason nobody makes ruffle socks anymoreWhy Alexander thinks AI is going to make human-to-human skills more valuable, not less 00:00:00 — Cold open 00:00:24 — Welcome, guest intro, and an early prediction on the trash verdict 00:01:57 — The Alexander / Alex / Alec identity crisis 00:04:51 — An Ancestry.com deep-dive into the DeMoulin family and a 1914 Supreme Court case 00:07:17 — How Alexander actually became an EMMIE client 00:12:15 — The “recent outcome”: Fin's acquisition by Salesforce 00:13:32 — Turning around the Titanic: inside Intercom's culture reset 00:17:37 — The branded swag challenge, and the leotard that missed the assignment 00:20:13 — Vibe-coding your own martech stack (and why that's job security for everyone else) 00:27:37 — MQL girls, outbound girls, and lead-scoring personas with better names than yours 00:30:23 — Fired from two sales jobs, back to his mom's basement in Portland 00:35:09 — The “Are You Trash?” talk that helped inspire this series 00:38:20 — Rebuilding trust after striking out three times, and sharing that story at Clay's Sculpt Conference 00:42:46 — Where AI actually fits into the future of ops jobs 00:45:19 — Final verdict Follow Pretty Funny Business on LinkedIn Subscribe on Substack MOps-Apalooza / Marketing Ops Community Leave us a review and subscribe wherever you listen — it genuinely helps the little podcast.

  2. Jun 30

    Is He Trash? Vol. 1: James Leedom

    If a salesperson calls you three times in one minute, calls back after you answer and tell them to stop, and then calls you again — and your takeaway is that Sydney should just pick up the phone — you might be the problem. This episode, we put that energy on trial. James Leedom is back. He joined us with approximately one hour's notice, from the Adobe office in New York City, on his vacation. That's either dedication or a character flaw — we spent the episode figuring out which. The verdict is in: not holistically trash, but there's a garnish situation happening. But before we got to James, Sydney had a developing story. She posted about getting triple-called — three calls in under a minute from the same sales number — and the LinkedIn comments absolutely lost the plot. Salespeople defending the practice, commenters insisting she should just answer, one person threatening to call all of her top-of-funnel. We broke down the four categories of people who showed up in those comments, discussed what AI dialers have to do with any of this (nothing, actually), and revisited the time Sydney ended up on the LinkedIn Lunatics subreddit. Turns out Lauren was on there first. Nobody noticed. Also this episode: The free spirit man taxonomy — what it means to be unbothered by the paper, and who is quietly funding that lifestyle Sephora is girls' Bass Pro Shop. Hockey is the boy aquarium. The Venn diagram was completed. James tells a dream. He was given multiple exits. He took none of them.The British English crisis: "pants" is not trousers, and this changes everything about the proposed series title.A compostable cup lid situation that accidentally explains every perpetual Salesforce sync error you have ever suffered through Timestamps00:01:30 — Welcome back (virtually). James is on vacation at the Adobe office.00:03:00 — Sydney's background. An inventory is taken.00:06:00 — Sephora is girls' Bass Pro Shop. Hockey is the boy aquarium.00:08:00 — Is He Trash? The game is explained. The evidence is reviewed.00:13:30 — The free spirit man. What he is. Who is financing him.00:16:40 — The triple call. Sydney's LinkedIn post. The developing story.00:18:00 — The four categories of people in those comments.00:19:30 — The time a webinar provider called five times in two minutes. During infant daycare hours.00:22:00 — AI dialers, the mental health emergency page, and a commenter threatening to call top-of-funnel.00:25:30 — Thought leaders vs. loss leaders. Where PFB lands.00:27:00 — London trip preview. British English. The pants problem.00:33:40 — Dreams segment. James had one. We gave him outs.00:37:20 — B2B marketing lesson: the compostable cup lid saga and what it has to do with your Salesforce sync error.00:40:45 — Final verdict: James Leedom is not holistically trash. Trash is a garnish. A topping. LinksFollow Pretty Funny Business on LinkedIn: https://www.linkedin.com/showcase/pretty-funny-businessSubscribe on Substack: www.prettyfunnybusiness.com Leave us a review and subscribe wherever you listen — it genuinely helps the little podcast.

  3. Jun 16

    The Cartel Canceled Our Work Trip (So We Went to Medieval Times)

    The work trip was supposed to be Playa del Carmen. Then a cartel leader was murdered, the US Embassy issued a warning, someone was already flying in from Lisbon, and Lauren had 72 hours to make a call on behalf of everyone. She pivoted to Orlando. The Airbnb in Mexico couldn't refund them. They ended up at Medieval Times. The chicken was fine. The horses were a problem. This week Lauren and Sydney are back from EMMIE's third annual consultant retreat —which was supposed to be Mexico, became Orlando, and ended with the entire team eating roast chicken with their hands in front of jousting knights. Along the way: new travel crimes are added to the canon, EMMIE hired its first man (Ethan, a growth advisor who wrote "Dick" on a Miro board without understanding why), and Leslie Douglas joins the sales team after the most chaotic non-interview in company history. Also this episode:• A new travel crime category: women are not immune, and cuticles on a plane floor are unforgivable• Sydney's seatmate in first class had a 30oz cold brew, a misogynist vocabulary, and four bathroom trips — in that order• Ethan has explained accrual-based accounting to Lauren no fewer than ten times. She understands it for exactly 30 minutes each time.• Ethan said "connective tissue" in a meeting and did the hand gesture. Lauren and Sydney were not okay.• Leslie hand-programmed NFC keychains for every consultant that tap through to each person's LinkedIn profile. She has been on the team for six weeks.• The Slackies: a surprise award ceremony built from a full year of Slack messages, featuring 50 certificates including Most Sympathetic to Robots, Most Dubious Units of Measurement, and a three-way tie for Most Flirtatious with the Marketo Product Roadmap• Medieval Times: recommended once, never again, the same knight wins every time, and $90 a ticket puts you in the nosebleeds which is exactly where you want to be. Timestamps:• 00:00:01 — Intro: the work trip recap begins• 00:00:54 — Travel crimes: returning offenses and new additions• 00:01:49 — New crime: cuticles on a plane floor• 00:02:30 — Sydney's first class seatmate and the 30oz cold brew• 00:07:55 — The real travel crime: the cartel cancels Mexico• 00:11:00 — The pivot to Orlando and the stress of making thecall• 00:14:18 — Introducing Ethan: EMMIE's first hire who is a man• 00:17:07 — What Ethan has taught them, and what Lauren still doesn't fully understand• 00:21:40 — Ethan's corporate vocabulary: leakage, connective tissue, meat space• 00:24:38 — The Big Deck Energy origin story and what Ethan wrote on the Miro board• 00:28:28 — Modesty departs; Leslie Douglas joins after a fake blind date interview• 00:32:20 — The NFC keychains; the Slackies award ceremony• 00:34:37 — Medieval Times: the team, the chicken, the horses, the verdict Links:Follow Pretty Funny Business on LinkedIn: https://www.linkedin.com/showcase/pretty-funny-businessSubscribe on Substack: www.prettyfunnybusiness.comMarketing Ops community: https://marketingops.com/Leave us a review and subscribe wherever you listen — it genuinely helps the little podcast.

  4. Jun 2

    AI Is Just Digital Transformation in a Trench Coat

    Turns out the thing AI can’t do is blow dry your hair. Or hold your popcorn at a Cavs game. The robots have officially started posting job listings for humans — they’re calling us the “meatspace” — and Lauren and Sydney have opinions. This episode is their seasonal take on AI: what it actually looks like to build something useful with it (Sydney built three agents, including one that reads Fathom call transcripts and drafts sales follow-up emails without being asked), why buying a composable AI tech stack is basically cutting the cable cord and ending up with more streaming subscriptions than you started with, and why you absolutely cannot give admin access to someone just because they look like they can hold their popcorn. Also: the cloud vs. on-prem history lesson nobody asked for but everybody needed, a platform called Rental Human where AI agents are the ones posting bounties, and the argument that “return to office” should be rebranded “return to on-prem.” Also this episode: • The word “digital transformation” once meant nothing to Sydney and she just faked it until it made sense — sound familiar?• Sydney's three-agent build: what each one does, what it replaced, and the one job it definitely did not replace• Composable AI tech stacks explained via cutting the cable cord, and why you’re going to end up paying more than cable• The AI pervert problem: what to do if you have one on your team, and why you cannot fire them• A platform where AI posts bounties for humans to complete — and yes, they called us the “meatspace”• A Vegas dream involving a limo, a forehead injury, and a roommate who was “at pancake breakfast, don’t worry about me.” • What dropping popcorn all over a Cleveland Cavaliers team shop taught Lauren about admin access Timestamps 00:00:01 — Welcome to Pretty Funny Business / seasonal AI take begins00:01:00 — Cloud vs. on-prem: the origin story, and why “return to office” should be “return to on-prem”00:04:05 — Sydney’s introduction to “digital transformation” and the art of pretending to understand it00:09:02 — AI is just the new digital transformation, and what marketing ops needs to do about it00:11:55 — Lauren’s three agents: the build, the workflow, and the job it did (and didn’t) replace00:18:30 — The Rube Goldberg AI workflow problem and the marble run that’s actually a failure00:20:47 — Composable AI tech stacks: Lego pieces, cable cord cutting, and the streaming subscription trap00:28:14 — The AI pervert on your team: identify, protect, document, do not fire00:30:18 — Rental Human: the platform where AI agents are posting bounties for humans00:32:01 — “Meat space”: what the robots are calling us and why00:35:34 — Dream segment: eight days in Vegas, a limo, a forehead, and pancake breakfast00:37:45 — B2B marketing lesson: the Cavs game, the popcorn, and admin access00:41:50 — Outro / bounty hunter applications open LinksFollow Pretty Funny Business on LinkedIn https://www.linkedin.com/showcase/pretty-funny-business/ Subscribe on Substack https://www.prettyfunnybusiness.com/podcast Leave us a review and subscribe wherever you listen — it genuinely helps the little podcast.

  5. May 19

    LinkedIn Lunatics: The Bodysuit Layer Debate, Bad LinkedIn Takes, and Sydney's Most Embarrassing Moment

    Pretty Funny Business | S4E02 — "We Made LinkedIn Lunatics (One of Us Did)"LinkedIn is a gift that keeps on giving — and this week, it gave us a lot. Sydney's viral bodysuit/tights/skort/underwear order-of-operations post has officially been featured on the LinkedIn Lunatics subreddit, and we are processing this together in real time. (Lauren was present and claims total innocence. The evidence suggests otherwise.)From there, we dig into the LinkedIn Lunatics mailbag: a man who thinks holding a baby is women's peak state of relaxation, a 25-year-old being told not to take a sabbatical to Thailand, someone who looks like Bad Bunny (maybe), and the eternal question — is this post a thought leader, a loss leader, or just a LinkedIn lunatic? Also this episode: The "does this post survive the group chat?" test for all LinkedIn contentA dream about Tinder, a dream about Grindr, and a dream about vibe coding at the gymWhether lavalier microphones should ever be hand-held (a heated debate)How abdominal surgery, a migraine, and an eye patch taught us something about B2B marketingThe describe-your-job-in-three-words challenge (the blockchain data one is sending us)If you've ever looked at your LinkedIn feed and thought "why is this here" — this episode is for you. Timestamps: 00:02:18 — Thought leaders vs. loss leaders vs. LinkedIn lunatics: a taxonomy00:05:25 — Sydney's post goes viral on LinkedIn Lunatics (the grief cycle begins)00:08:35 — The bodysuit/tights/skort/underwear order of operations, explained00:11:25 — The comments section: supportive men, sales bros, and Kimmy saves the day00:16:08 — LinkedIn lunatics mailbag: women's "peak state," Thailand sabbatical, Bad Bunny00:24:59 — Lunatic mailbag continues: lavalier mics, potion polls, cat in a toga00:34:33 — Vibe coding at the gym: dream or nightmare?00:36:19 — Bodies, Pilates, and surgery (the eye patch story)00:41:38 — In conclusion: keep people on their toes, especially on LinkedInLinks: Follow Pretty Funny Business on LinkedIn: https://www.linkedin.com/showcase/pretty-funny-businessSubscribe on Substack: www.prettyfunnybusiness.comLinkedIn Lunatics subreddit: r/LinkedInLunaticsLeave us a review and subscribe wherever you listen — it genuinely helps the little podcast.

  6. May 5

    Ball Pit Dreams

    Sydney and Lauren kick off Season 4 with a full recap of MOpsapalooza — including the legend of Lady Effington, a ball pit that became more hot tub than pool party, a slide that lasted approximately five seconds before the fire marshal intervened, and some deeply anonymous corporate confessions. Plus: what a four-year-old's encounter with the mayor of New York can teach you about B2B marketing. It was all just a dream, obviously.

  7. Jan 6

    Professionalism Is Fake: Zoom Etiquette, Makeup Rules & Work-From-Home Myths

    Welcome to the final episode of Season 3 of Pretty Funny Business! Today’s topic? Professionalism.What is it? Who decides what counts? And why did we all buy day-to-night outfits in 2012 even though we were going absolutely nowhere at night?We break down:  Why “professionalism” is mostly made-up Zoom etiquette we all pretend to follow (camera on? makeup? …internet?) The remote-work dress code nobody asked for Day-to-night fashion and the lies magazines told us Makeup expectations, gender double-standards & office culture Our most unprofessional moments with clients (in a cute way)If you work from home, show up to Zoom in a hoodie, or have ever been judged for not wearing makeup — this one’s for you.📲 Connect with us:Lauren → https://www.linkedin.com/in/laurenaquilinoSydney → https://www.linkedin.com/in/sydneymulligan👗 Try Nuuly and get $30 off your first rentalNuuly – Sydney’s Invite Link: https://share.nuuly.com/sydney9937Nuuly – Lauren’s Invite Link: https://share.nuuly.com/lauren42247🛠 Tools we swear by (affiliate links – we earn a small commission):Fathom for meeting notes: https://fathom.video/?source=agencypartners&ps_partner_key=c3lkbmV5bXVsbGlnYW43MzQ&ps_xid=aKkNfXKYBvY1Hp&gsxid=aKkNfXKYBvY1Hp&gspk=c3lkbmV5bXVsbGlnYW43MzQAirtable to manage workflows: https://airtable.com/invite/r/NHkCkkSDRun your whole business like a pro with Google Workspace: https://workspace.google.com/landing/partners/referral/gws2/?utm_source=sign-up&utm_medium=affiliatereferral&utm_campaign=apps-referral-program&utm_content=9KKCZ0C📧 Want to work with us? Find out more at https://www.emmieco.com/

  8. 12/23/2025

    12 Days of Pretty Funny Holidays 🎁 Gifts & End-of-Season Confessions

    Welcome to our 3rd annual 12 Days of Pretty Funny Holidays!In today’s special holiday episode, we exchange 12 chaotic, heartfelt, and wildly unserious “gifts” inspired by the year we've just survived together. From Chick-fil-A nugget ice to golf meltdowns to protein-based baby formula to flight upgrades… this is our peak business-girlie holiday energy.We talk:  The tradition of our 12 Days gift exchange How we somehow made 16 full video podcast episodes this year Nugget ice discourse Golf, husbands, and the Real Reason men love “being outside” Our obsession with baby-formula-tier protein 2025 client wishlists And just nearly wrapping Season 3 with a whole lot of gratitude📲 Connect with us:Lauren → https://www.linkedin.com/in/laurenaquilinoSydney → https://www.linkedin.com/in/sydneymulligan👗 Try Nuuly and get $30 off your first rentalNuuly – Sydney’s Invite Link: https://share.nuuly.com/sydney9937Nuuly – Lauren’s Invite Link: https://share.nuuly.com/lauren42247🛠 Tools we swear by (affiliate links – we earn a small commission):Fathom for meeting notes: https://fathom.video/?source=agencypartners&ps_partner_key=c3lkbmV5bXVsbGlnYW43MzQ&ps_xid=aKkNfXKYBvY1Hp&gsxid=aKkNfXKYBvY1Hp&gspk=c3lkbmV5bXVsbGlnYW43MzQAirtable to manage workflows: https://airtable.com/invite/r/NHkCkkSDRun your whole business like a pro with Google Workspace: https://workspace.google.com/landing/partners/referral/gws2/?utm_source=sign-up&utm_medium=affiliatereferral&utm_campaign=apps-referral-program&utm_content=9KKCZ0C📧 Want to work with us? Find out more at https://www.emmieco.com/

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Ratings & Reviews

5
out of 5
7 Ratings

About

Introducing « Pretty Funny Business », the playground brand we were forced to create in order to corral our founders’ nonsensical ideas and general tomfoolery. From the founders of, by not generally endorsed by, Emmie Collective. Hosted by Lauren Aquilino and Sydney Mulligan. You can expect off-the-cuff banter on feminism, funny business, and well.. not-so-funny business. Join us out of curiosity, stay for the hot takes and dad jokes. www.prettyfunnybusiness.com

Information

  • Creator
    EMMIE Collective
  • Years Active
    2022 - 2026
  • Episodes
    75
  • Rating
    Explicit
  • Copyright
    © EMMIE Collective
  • Show Website
    Pretty Funny Business