This Meeting Could've Been a Podcast

Josh wants to do owned events

Josh wanted his ChiliPalooza moment. He also wanted a Toyota Corolla people could scream in. What he got was the Jess edit — and it involved ghosts. They already knew small private dinners worked. Drive by Exit Five had proved it. What if they just did it four times? $45K for four cities. $880K in projected pipeline. Josh is still waiting for his ChiliPalooza, but this will do. Three words from Josh. Jess had the whole concept. She built the landing page herself that evening. And the T-shirt the audience voted against? She printed it anyway. Get to the good stuff: [00:00] The T-shirt vote is in. Josh is not okay [00:46] If you don't have your own user conference, are you even a real startup? [01:32] Jess pumps the brakes on the big event. One Toyota Corolla full of screaming marketers, however, is still very much under consideration [04:01] Josh also wanted a community. Badly. He still does, for the record. Jess had questions about who was going to run it. [05:42] Event vs Community: Community needs a full-time person, a moderation strategy, and a prayer. Events need a good restaurant. Easy choice [07:06] Josh says three words. Jess goes "say less." The Ghost Tour Tour is born [08:10] A tale of two strategies: build it and hope they come, or sidecar the events where they're already showing up [10:41] The Ghost Tour Tour explained. No, it's not a haunted house [12:35] The invite request gamble: it scared Jess, but paid off. Turns out nobody wants to be the one at a conference with no dinner plans [15:12] Sponsoring the event has a perk nobody talks about: you get the attendee list. Pull from one side, push from the other. [16:18] Pit stop. Marketers, you deserve nice things. Josh and Jess deliver [16:38] Jess wants to talk budget. Josh does not. $45K for four events changes his mind [17:52] The Ghost Tour Tour roadshow revealed. Four stops, four cities, and a September that's going to be a lot [18:59] Easy to think you can run an event alone. Jess hired Steph Pennell at INGÉNUE before it became a problem [20:11] Josh vs democracy: three T-shirt designs, one public vote, one very unhappy CEO [23:40] Bonus swag reveal — a cinch bag, a ghosty, and a city outfit plan idea that died on contact [24:14] Jess hands the attendee list to Sara McNamara. What comes back is either voodoo magic or a mild privacy concern. Either way, it works [25:31] Did Jess overbook? Yes. Did it work? Also yes. Spirit Airlines, take notes [27:10] Jess builds the Ghost Tour Tour landing page in an evening using Claude. Before Claude Design existed. She vibed harder [31:19] Jess and the marketing team picked unscalable outreach on purpose. Sometimes you just have to do it the hard way [32:31] The invite bell curve explained — from why people don't commit until the week of, to why a ghost that follows you home is a pretty good reason to show up [34:23] Jess on how she'll know if the Ghost Tour Tour worked. Six meetings per stop. $880K in projected pipeline. $45K invested. The math is mathing [36:32] What if it doesn't work? Jess becomes a ghost. What if it does? Josh wants a 5000 person event. Damned if you do, damned if you don't   This Meeting Could’ve Been a Podcast is a Vector [https://www.vector.co/] production. Filmed and produced by Sweet Fish [https://www.sweetfishmedia.com/]. Editing by Handy Man Edit [https://www.handymanedit.com/]. Show notes by Content 10x [https://www.content10x.com/].  Music by Peter McIsaac Music [https://www.premiumbeat.com/artist/peter-mcisaac-music].

Jess hires a demand gen marketer

Jess opens a demand gen role. The brief: run ads, talk to customers, build in public. Sixty applicants land in her inbox in 48 hours. Six months later, still searching. Josh's read on the situation? "Do you just really suck at hiring?" Most candidates checked two boxes. Nobody checked all three… until Kelly showed up and had CTV ads running within two weeks. Hear how six months of searching ended with a hire who had an ABM program live before Jess could blink. Get to the good stuff: [00:00] Jess asks for a demand gen marketer. Josh says yes. Cue a six-month odyssey [02:32] Jess had three boxes. Run ads. Talk to customers. Build in public. Box three is where most demand gen marketers ghost you [05:06] Jess calls every marketing leader she knows. Same answer every time: hardest role I've ever hired for. Josh hints she just really sucks at hiring [06:14] Demand gen means something different everywhere. ABM. Growth. "Write the blog, hit send." Jess’s preference? Someone who'd defied all the laws of checklist marketing [08:20] Sixty applicants become twenty-five interviews. Two boxes, consistently. Never three [10:12] Six months in, Jess is willing to try anything. Newsletters. Craigslist. Missed connections [11:35] It’s December, the Series A is coming, sales want pipeline… and the company helping marketers run better ads still doesn’t have a demand gen marketer [12:20] Jess has a "just hire someone" moment. Josh holds the line [12:50] Eric Linssen of Demand Collective has a name. Kelly Arndt. Jess has been waiting 84 years for this moment [14:32] Kelly has the demand gen chops and he also has a content brain. The six-month search suddenly makes a lot more sense [15:40] Jess skips “where do you see yourself in five years?” and hands Kelly the real budget and the real targets. He comes back with month one [16:33] Kelly could hold a room with a CMO. Box three — finally ticked. Jess considers drone surveillance and wire taps while she counts down to Kelly’s Day One [17:54] Kelly basically starts before he starts. Sales calls, Slack channels, marketing plans. Disclaimer from Josh: entirely voluntary. [18:48] Nobody's week two checklist says "run connected TV ads." Kelly's did. 180,000 ICP contacts. Surround sound campaign, activated [21:40] Jess's mastermind asks: when organic starts dying, how do you nurture? Her answer. Ads. Their eyes lit up [23:16] Vector ads are showing up on Disney+, Hulu, Paramount. People in their network are texting mid-show. Jess only watches shows involving ghosts. Unrelated [24:13] Josh hears ABM program, and panics. Kelly has it live mid-panic [27:49] Building a tool that pulls pain point quotes straight from sales calls and turns them into ad copy?  Kelly is living in 2049 [28:49] Time to stare deeply into the camera. Marketers, you need to hear this [29:43] Three hiring tips from Jess, starting with: you're going to kiss a lot of frogs [33:44] Josh tries to 6X the pipeline goal. Jess declines.   This Meeting Could’ve Been a Podcast is a Vector [https://www.vector.co/] production. Filmed and produced by Sweet Fish [https://www.sweetfishmedia.com/]. Editing by Handy Man Edit [https://www.handymanedit.com/]. Show notes by Content 10x [https://www.content10x.com/].  Music by Peter McIsaac Music [https://www.premiumbeat.com/artist/peter-mcisaac-music].

Josh raises a Series A (and becomes a monster)

Season three Jess is not season one Jess. Same goes for Josh. Raising $10 million will do that to a person.  Josh hits the road to raise Vector's Series A. Weeks later, he's back full of ideas. None of them related to Vector's actual business. While Josh is away, Jess and the leadership team stop waiting for permission. They figure out what to do without him. Turns out: they know what they're doing. Back on the investment front, Josh sends a telegram. Complete ye olde English prose from a plane at 3 am. Hear how Josh used the whispering game, a New York meeting slot he hadn’t booked yet, and high school lunch table vibes to get through the roadshow. Get to the good stuff: [00:00] Josh returns from the investment roadshow with three groundbreaking business ideas, all of them “great.” Sigh. [02:24] The raise isn't the win your LinkedIn feed thinks it is — why Josh resisted until he couldn't. [04:02] Jess explains how they gathered customer feedback for the raise three months after a hard pivot. Alex said I've got this... and delivered. [07:30] Jess coined the phrase Deep Ass Financial Dive (trademark pending), and yes, it is exactly what it sounds like. [09:57] Churn versus Optics: Josh admits letting optics win for the fundraising window. [11:57] Josh explains how having the biggest quarter in company history changes the room. [13:10] Fundraising sucks. Josh does not recommend… kind of. [15:22] Josh’s investor playbook: practice reps, whisper campaigns and an imaginary New York slot. [20:46] Dad is out of the house. Jess learns to stop asking for permission. [24:01] Jess starts feeling like Josh is at war. Josh sends her a telegram from the fundraising front... in ye olde English. [26:00] Josh turns Fridays into grenade drops. We need to become an agency. AI is replacing us all. Something else about AI. Goodbye. [28:30] Affirmations break. Live, laugh, lower CAC. [29:05] The $10 million question… why SignalFire and HubSpot Ventures said yes. [33:33] Jess and Josh ditch the press release for their Series A announcement. They were over the theater, so naturally…cue the 90’s sitcom-style video. [37:59] Jess pitches real ghosts (naturally). This Meeting Could’ve Been a Podcast is a Vector [https://www.vector.co/] production. Filmed and produced by Sweet Fish [https://www.sweetfishmedia.com/]. Editing by Handy Man Edit [https://www.handymanedit.com/]. Show notes by Content10x [https://www.content10x.com/]. Music by Peter McIsaac Music [https://www.premiumbeat.com/artist/peter-mcisaac-music].

Season 3 trailer

Gird your loins: Season 3 of This Meeting Could've Been a Podcast drops June 10.

Josh wants to redesign the website (for real this time)

Josh wanted to redesign the website. Jess said no. A few months later, Jess came back with the same idea. She called it an Uno reverse. Josh may have finally admitted Jess is wiser than he is.  A repositioning gave them the green light — a new narrative, new pricing, two product pages that didn't exist before. What Josh thought would be a simple redesign turned into three mood boards, a glow up that didn’t kill Ghosty, and a 37-line launch checklist. If you've ever underestimated what it actually takes to ship a new site — or had to explain why it's not just a fresh coat of paint — this one's for you.  Hear how Jess navigated a full site overhaul, got leadership buy-in by showing her work, and figured out what it really takes to launch a website that tells a story. Get to the good stuff: [00:00] "Our website is atrocious." Bold words from the guy who built it. The redesign finally gets the green light.  [01:07] Why this redesign happened now — and not when Josh suggested it. [02:03] What you keep vs. what you kill in a brand refresh. Spoiler: Ghosty lives.  [03:27] First impressions matter. How design shapes how buyers perceive your product, not just your brand.  [05:10] The “real” reason Josh approved the redesign budget: those gradients with text on them were haunting him. [06:01] Keep it, evolve it, or kill it. Three buckets to sort your brand before you redesign anything. [06:54] Inspiration audits, mood boards, and why "I just don't like it" isn't helpful feedback.  [10:20] Giving good design feedback is a skill. A little word vomit is okay.  [12:22] Three mood boards walk into a bar. One's too safe, one's too stark, one's just right. [15:09] Wireframes, design applied, and those "aha" moments that never get old.  [17:01] Why pricing and packaging research didn't just live in a spreadsheet, and how it influenced how the site was structured. [18:48] Moving from feature-based navigation to product-led storytelling.  [19:50] Getting leadership to understand a website isn't "just a website". Show your work. Every step of the way.  [21:39] Product imagery that actually tells a story — and how marketing and product crushed it.  [23:24] Positive affirmations to soothe your soul. Plus, some ASMR that nobody asked for.  [24:06] The parts of a site launch people often forget: developers, RevOps, SEO, tracking, QA. It's a lot.  [25:33] Content staffing realities and why your sitemap can be your best project management tool.  [29:12] Launch day logistics: pick a date, be flexible, and for the love of Ghosty, build a checklist.  [31:30] Josh wants last-minute typography changes. Jess ends the meeting. As she should. This Meeting Could’ve Been a Podcast is a Vector [https://www.vector.co/] production. Filmed and produced by Sweet Fish [https://www.sweetfishmedia.com/]. Editing by Handy Man Edit [https://www.handymanedit.com/]. Music by Peter McIsaac Music [https://www.premiumbeat.com/artist/peter-mcisaac-music].