In this episode, we talk with Laura Lopuch, who helps online service providers start conversations with high-quality leads through cold outreach. She built the WARM framework and the Warm Client Method, and her whole argument is that the leads you want are already out there leaving public signals about the problems they have—you just have to do the research before you hit send.

We talk about what qualifying someone actually looks like from the outside, how to name a prospect’s blind spot without insulting them, why “are you interested?” is a better ask than “book a call,” and where the follow-ups fit. We discuss the reality of dealing with inbox overwhelm, how to stand out from the volume of terrible cold outreach, and why outreach isn’t just for prospecting.

* What a cold email actually is—and why the transactional “buy my stuff” version is a myth

* Gap signals: reading the public evidence that someone has the problem you solve

* How to infer budget, team size, and urgency before you ever send an email

* Naming a blind spot without negging—using outside research instead of “your brand is bad”

* Consent-based outreach and why “are you interested?” is the right-sized ask

* Micro-yeses in the email vs. escalating-commitment persuasion tactics (they’re not the same thing)

* Fast burn vs. slow burn: sales emails, podcast pitches, collaborations, workshops, JVs, sponsorships

* Whether this works for B2C and coaching, not just B2B services

* Laura’s actual numbers—reply rate, conversion rate, and why the wins live in the follow-ups

* Why the low bar in everyone’s inbox is good news for anyone willing to sound like a person

“A lot of people get confused when I say relevant, and they're like, 'Yeah, first name, company.' And it's not actually that. That's personalization. That's icing on the cake. The relevancy is the deeper method of tapping into what is this person's existing goal? What are they working towards? Are they working to sell their agency in five years? If so, they need a controllable source of getting new clients in the door, one that doesn't depend on algorithms.” - Laura Lopuch

About our Guest

Laura Lopuch

The WARM Client Method

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Meg Casebolt

Jessica Lackey

In this episode, we walk through our own fall programs: Meg’s Signal, a year-long mentorship focused on AI discoverability, and the seventh round of Jessica’s Define Your Foundations cohort. We’re not pitching them so much as taking them apart — what’s in each phase, what order things go in, what we changed after watching people get stuck, and what we’ve learned about how long it actually takes for work to sink in.

We talk about why Meg teaches live twice a year instead of going evergreen, why Jessica spread the “intellectual horsepower” decisions across six months instead of front-loading them, how the BEACON framework maps to positioning work, and where our two programs hand off to each other. We also get honest about who each program isn’t for.

* Why the length of a program should be dictated by what’s actually in it

Signal Details:

* Meg’s Signal: four three-month cycles, and why it’s a mentorship, not a membership

* Why “learn it twice” beats “learn it once” — and what happens between the training cycles

* Why Meg won’t make the program evergreen (spoiler: the material changes every six months)

* The BEACON framework: brand entity, expertise, authority, content infrastructure, omni-channel presence, narrative

Define Your Foundations Details:

* Jessica’s four phases in Define Your Foundations — and why phase one is setting down the shoulds

* “Business model Tetris”: how your client, offer, and price point change what marketing you actually need

* Why front-loading every big decision makes people feel behind

* Co-working and laser coaching vs. office hours — designing for people who don’t ask questions in groups

* The three things that separate cohort members who get results from those who don’t

Which Program Might Be Right for You:

* Where positioning work ends and discoverability work begins (and which one to do first)

* Who each program is not for

“There’s another business coach who does a six-week accelerator, and she goes through her six core systems, because she has six systems similarly. And I’m like, ‘that is like pouring a flood of water onto concrete.’ It’s so fast. Her whole thing is fast, and my philosophy is that if you try to learn six full business systems in six weeks, you’re not gonna retain any of it.

So my point of view is not just about what the systems are, but how it informs the offer itself and the client I’m serving. And if they want speed, awesome. My narrative has to connect to what I’m selling and why.” - Jessica

Resources

Signal — Meg’s year-long mentorship program

Define Your Foundations — Jessica’s six-month cohort

The Deeper Foundations Membership

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Meg Casebolt

Jessica Lackey

Failure is one of the only universal experiences in business, and it’s also the one we’re least willing to say out loud. Most of the time when failure does get talked about publicly, it’s been sanded down into a tidy redemption arc or it’s behind a paywall. Jess Manuszak decided to throw a party instead.

In this episode, we talk with Jess Manuszak, owner of the Denver copywriting studio Verve and Vigour and founder of The Failure Ball, a biannual black-tie event where people get on stage in gowns and crowns and tell the truth about how they failed. The Ball started in 2020 with a goal of 30 attendees, sold out at 78, and last year filled a Victorian mansion with 200 people. All profits go to To Write Love On Her Arms, because the connection between shame and suicide is exactly why the event exists. The next one is September 19, 2026 in Denver.

We talk about the difference between the failures we actually caused and the ones the online business world decided to call failures, why the format has to be in-person (and glamorous, and not under fluorescent lights), and how to know when your story belongs on a stage versus in your therapist’s office.

* Why shame festers when failure gets left in the dark

* The rule that a failure has to be one you actually caused

* Getting a job isn’t a business failure — but the industry treats it like one

* Why the format is a ball, not a summit, a conference, or a podcast

* The failure behind the failure: what speaker coaching actually uncovers

* “You don’t have to turn your trauma into content” — and how to know when you want to

* Knowing why you’re sharing: to feel less alone, to be witnessed, or to get input

* Where the line sits between authenticity as a human and your brand’s story

* Holding space for clients versus asking clients to hold space for you

* Why at least one Failure Ball speaker every year is actively failing, with no gold bow on it

“We know the psychology behind shame. We know that the antidotes to shame are community, non-judgment, sharing, and self-kindness. That’s really what we’re here for — drag your dark secrets into the light. You feel like they’re so dirty. Bring them into this room and you’ll see how squeaky clean they actually are, because I guarantee someone in this room relates. It’s the failure behind the failure. Everybody wants to be loved. If you’ve had a launch that failed, maybe everyone hasn’t lost a million dollars at launch, but everybody wants to try to have financial stability in their life. It’s those underlying threads that connect everyone and help heal that trauma — versus, for $27 in four installments, we will heal your shame for you.” — Jess Manuszak

Resources Referenced

The Failure Ball

Mike Ganino’s episode

Nicole Lewis-Keeber’s episode

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Meg Casebolt

Jessica Lackey

It’s that there’s no distinct perspective behind it.

In this episode, we talk about the chicken-and-egg problem underneath developing a reputation and referrals: you need a point of view to get in the room, but you need to be in rooms with actual humans to sharpen a point of view. We get into why AI-workshopped positioning defaults to the average of what everyone else is already saying, what it actually takes to be referable, and how long it really takes for an angle to become something people seek you out to talk about.

We’re honest about the awkwardness of testing out your language with other humans and provide a “call me when” framework to help you sharpen your positioning for your network and for AI.

* The chicken-and-egg problem: needing a POV to get in the room, and needing the room to build a POV

* What it actually takes to be referable: category, persona, approach/angle

* The “Call Me When” exercise, and why specific scenarios are often clearer than results-based messaging

* Semantic vs. somatic: reading the face of the person you just pitched

* The “take your name off of your website” test

* Why “I could do that” is a trap, and how naming what you don’t do tightens your referrals

* The three-year timeline of turning a topic into inbound requests

* Being known for a feeling, not just a framework

* The linguistic throat-clearing AI adds, and how to cut 20–30% of it

“The perspective has to come first. The uniqueness, the differentiator has to come first. Because people are busy, inboxes are crowded, DMs are full of garbage, and if your pitch sounds like everyone else’s pitch, or if your website sounds like everyone else’s website, or if your email sounds like everyone else’s email, then I don’t care how many times you workshop it — I could take your name off of it and put someone else’s name on it, then I’m not gonna hire you. I’m not gonna bring you into my membership. I’m not gonna bring you on the podcast. You might be the nicest human alive, but if I don’t hear something different in your messaging, then I don’t know how to amplify your message.” - Meg

Resources Referenced

Angie Stegall - Coach

Sharon Wagner - Branding

Hillary Weiss Presswood - Campaigns

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Meg Casebolt

Jessica Lackey

Jessica is a cartoonist and author turned business coach for professional creatives, helping them finish the self-generated work that has no deadline and get paid well enough to actually have time for it. In this episode, she walks us through the very unglamorous process of taking 10-plus years of courses, newsletters, and frameworks, most of it locked behind paywalls or buried in podcast audio, and making it cohesive and legible for both people and AI. She and Meg get honest about why podcasting is great for ideas and terrible for discoverability, what it actually takes to update a Wikipedia page, and why The Guardian counts as proof but a marketing podcast doesn’t.

We talk about the difference between productivity and capacity, why “decide” and “reflect” are the phases everyone skips, and what it means to pay yourself first with your time instead of your leftover minutes. We get into cyclical burnout, idea debt, and the genuinely hard work of deciding what you’re not going to do—and being at peace with it.

* Why “multi-hyphenate” isn’t a bug of entrepreneurial life

* Cyclical burnout: what happens to someone who always has new ideas

* How Jessica consolidated a career-long body of work into something legible using a bottom-up, feedback-driven process (and Claude)

* Capacity as a lens—not just your time, but your neurological and emotional bandwidth—and why it fluctuates by the day and the season

* Grow work vs. build work, and the tension between expanding your audience and cementing a legacy

* What it actually takes to be legible online—AI discoverability, entity confusion, and why Jessica still shows up as a cartoonist first

* The Creative Engine’s four phases—collect, decide, act, reflect—and why decide and reflect get skipped even though they’re the shortest

* The “flexible container”: building a finishing structure with edges that can still absorb a sick kid or a health flare-up

"I actually hate the word productivity and try to not talk about myself as a productivity coach, because—I still have to use it a lot 'cause it's the word people know. But productivity literally means: how do you have the same amount of capacity and jam more stuff into it? How do you get more stuff out of whatever you have available? And of course you can look at it different ways, but that's literally what it means in the economic sphere. Which is just a point of view that doesn't work for humans, and especially creatives and people who have big ideas and are trying to do the self-generated stuff." —Jessica Abel

About our Guest

Jessica Abel

Out on the Wire

In the Weights

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Jessica Lackey

In this episode, we catch up on what our month off actually looked like — Jessica’s West Coast “book tour” meeting Deeper Foundations members across four cities, and Meg’s glaucoma surgery and a quieter, more foundational summer of business work.

We talk about travel, illness, eye surgery, membership relaunches, and the discomfort of resting without immediately filling the space with something new — plus why a genuine pause turned out to be exactly what both the business and the podcast needed.

* Why Jessica took her book on an unofficial “tour” through Seattle, Portland, San Francisco, and LA

* The public transit challenge: one rideshare in twelve days across four major cities

* Meg’s glaucoma surgery, what a week without screen time actually looks like, and why she scheduled it for the slow season

* What it actually looks like to let go of “big, hairy, ferocious projects” for a season without the business falling apart

* Relaunching the Deeper Foundations membership without ever having done a formal launch sequence before

* The “collective pause”: a shared sense that clients, colleagues, and the industry at large all pulled back at the same time this summer

* Why reflection is the step that gets skipped in a weekly podcast cadence — and why that’s a problem worth solving

* The World Cup as a rare moment of monoculture in an increasingly fractured media landscape

* What “resting but not regenerating” feels like when travel and motion replace actual stillness

“I think sometimes when you’re in a production content creation process, you don’t have a chance for reflection. When it comes to podcasting, because of the weekly cadence, you’re always gathering ideas, lining up guests, and thinking about what you want to talk about. Then we have to get together, we have to record, we have to produce, we have to create the show notes — we have to do all these different things. And that fourth step, reflect, is the easiest one to miss, because the cadence has been determined, and we lose sight of what it is we’re trying to do here.” -Meg

Resources

Leaving the Casino

Just for the Summer by Abby Jimenez

Succubus Blues series by Richelle Mead

School of Moxie with Mary Williams

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Meg Casebolt

Jessica Lackey

In this episode, we get into what’s behind our summer sabbatical: the planning required to step away (turns out you have to prep in advance), why listenership naturally dips in the summer, and why we decided against reposting old episodes under a “best of” label. Meg talks about her seasonal rhythm—short summers in a cold climate, kids’ camp schedules, less desire to sit at a microphone—and Jessica walks through a stretch of heavy travel, a meaningful family transition, and finally having the room to take a real beat.

We talk about the difference between maintaining and growing, why a body of work keeps earning for you even when you slow down, and the case for “mental composting” as actual business strategy. We also get into relationship marketing that doesn’t look like marketing, and why taking time off doesn’t mean you’re bad at your business. Plus a live tarot pull that may or may not predict another book.

* Why we’re taking all of July off—and why it’s a sabbatical, not just a slowdown

* The prep it actually takes to step away (hint: start two to three months out)

* How summer listenership shifts when everyone’s out living their lives

* Meg’s seasonal rhythm: cold-climate summers, camp schedules, and working less on purpose

* Jessica’s summer of travel, a family transition, and finally taking a beat after years of building

* Why a “body of work” keeps working for you when you stop pushing

* Mental composting and the case for creative downtime (see: Lin-Manuel Miranda in an airport)

* Maintaining vs. growing—and why you don’t always have to be in growth mode

"Taking time off doesn't mean you're bad at your business. But it does mean that if we're going to take time, we need to prepare for that two to three months in advance. Otherwise it's that vacation-y feeling where you cram.

I don't have a whole bunch of curriculum that I'm creating. I'm not writing and launching the book. I'm at a place where I can take a beat, so I'm gonna take it. Past Jessica did a good job, present Jessica is gonna take advantage of that, and future Jessica already knows what she's doing in August and September. There's more launches coming. They're just not happening in July." -Jessica

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Jessica Lackey

In this episode, we talk with Nikki McKnight—Meg’s romance-podcast co-host, operations expert, and newly minted Certified Customer Experience Professional—about why she niched her business down into customer experience and launched a new business podcast called Would Recommend. Nikki walks us through how she went from “I can do everything” operations work to building a practice around a single belief: that for founder-led businesses, customer experience is the best marketing and retention strategy there is.

We dig into the difference between customer experience and customer journey, why emotions are what actually drive referrals, and how matching your brand promise to your real experience builds (or breaks) trust. There are frameworks—Nikki cannot help herself, and neither can we—but mostly it’s a conversation about the gap between what we say we deliver and what it actually feels like to be on the receiving end of it.

* Why Nikki niched down in belief rather than service or audience—and why that’s easier to sell and refer

* The customer experience pyramid: satisfaction → ease → enjoyment—and why advocacy only lives at the top

* Customer experience vs. customer journey: “the journey is a lane, the experience is the whole highway system”

* Why emotions create memories, memories create perception, and perception is the only thing that drives behavior

* Brand promise as an operational standard (not a mission statement)—and why you can control your promise and experience but never your customer’s perception

* The Mr. Rogers writing rule that changed how Nikki thinks about every email, sales page, and support reply

* Category expectations: how to spot what customers already assume about you—and deliberately disrupt it

* Giving your customers the language to refer you (because “you just need Nikki, go” doesn’t convert)

* When great delivery meets AI-generated marketing—and why a mismatch quietly destroys trust

* Principles vs. methodology, and why lead magnets built on tactics expire the moment the platform changes

* CX train wrecks (yes, QuickBooks and Canva, we’re looking at you) and reporting “from the scar, not the wound”

“Your whole job is to create memories. Because if you can elicit an emotion in someone, emotions are what create memory. When someone creates a memory, then they have a perception of something, and it’s perception that drives behavioral change. You can’t just jump straight to a behavioral change.

And customer experience is not just what starts when someone pays you. It’s not the customer journey. The journey is a lane. The experience is the whole highway system.” - Nikki McKnight

About our Guest

Would Recommend (Nikki's new podcast)

Unreasonable Hospitality by Will Guidara

CCXP – Certified Customer Experience Professional designation

Acceleration Strategy Inc. (12-week customer experience program, Toronto)

Fixable with Frances Frei and Anne Morriss (the Southwest episode)

Derek Thompson's podcast: the NBA / Adam Silver episode

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Jessica Lackey

In this episode, Meg breaks down entity-focused search and discoverability: the shift from optimizing the domain versus optimizing the entity and the person. She explains what an entity actually is (think of it as a star in a constellation, or a suspect on a murder board with red strings connecting everything back to you), and why so many of us have fragmented, disconnected, or missing entity signals without realizing it. This is the same material that opens her Signal mentorship, compressed into one conversation.

We talk about why your full name needs to be on your website, what schema markup does and why it’s suddenly mattering again, and the difference between work you control (your own pages and copy) and the third-party validation you can’t fully control but absolutely need. This is the first step of the slow, compounding, multi-month play—and why the work pays off even if the AI citations take their sweet time to show up.

* Why “it’s not just Google anymore” changes everything about how you get found

* What an entity actually is—person, book, program, company—and how they connect like a constellation

* The three most common problems: missing entities, disconnected entities, and entity fragmentation

* Why Meg’s own podcast and business weren’t connected in the AI knowledge map (and how she fixed it)

* The copywriting habit that’s quietly hurting you: all client-facing language, no expertise or “who I am”

* Schema markup explained in plain English—and the “Same As” code that ties your whole body of work together

* How to narrate a pivot so AI (and humans) know you’re the same person who changed

* Why you can build a perfect entity and still not get recognized without external validation

* The referral guide idea: a “call me when” doc for both the humans and the machines

* How long this really takes—and why Perplexity shows changes before ChatGPT ever will

“We get to signal that we would like things to be entities, but we do not get to decide which are the entities that are recognized. So, Jessica Lackey already exists in the knowledge map. We know that because if you go to ChatGPT or Claude or Google and say, ‘Who is Jessica Lackey?’ there’s an answer there.

But unless you are super clear about this is what I want you to do, AI can pull from anywhere. So if you wanna be more in control of how you’re represented and the language that it’s using about you, then you need to be clearer about how you want to be defined.” -Meg

Resources

Signal Mentorship

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Meg Casebolt

Jessica Lackey

In this episode, we’re joined by returning guest Bev Feldman, email marketing strategist for credentialed professionals at Your Personal Tech Fairy. Bev recently repositioned her business to focus on credentialed service providers — and she’s having her best revenue months ever doing it. We talk with her about has changed in her business marketing, including the shift from “marketing” to “marketing AND sales,” replacing her freebie with a gated Services Guide, and the quarterly check-in email that’s converting her smaller, plateaued list better than it ever did when it was growing.

We talk about why most credentialed pros either email too rarely (out of spam fear) or too often (copying content-creator cadences), why “top-of-mind selling” works better than launch selling for service providers, and the difference between a newsletter (selling ideas) and email marketing (selling products and services) — and why that distinction matters when everyone is being herded onto Substack. We also get into welcome sequences, the Expert’s Paradox, the Gmail open-rate drop, and what happens to a sales call when a Services Guide does the qualifying for you.

* Why the online business email playbook doesn’t translate when your audience is consumers, not other online business owners

* The two extremes Bev sees credentialed pros make — emailing too rarely vs. copying daily content-creator cadences

* Reframing email as a sales tool, not just a marketing tool (with full credit to Kendall Cherry)

* “Top-of-mind for triggering events” — what selling actually looks like for therapists, financial advisors, and other service providers

* The Expert’s Paradox: why experts default to DIY tutorial content and why AI just commoditized that

* Replacing the freebie with a Services Guide that pre-qualifies leads before they ever book a call

* Why Bev’s list has plateaued — and why that’s a feature, not a bug

* Different welcome sequences for different entry points (Services Guide subscribers vs. newsletter subscribers)

* The quarterly “I have openings — want to work together?” check-in email

* Newsletter vs. email marketing: why Substack and Beehiiv are the wrong tool if you’re trying to sell services

* Why unsubscribes are good news, and the recent Gmail change that dropped open rates across the board

"Email marketing is not just a marketing tool, it is very much a sales tool. But you can do that in a way that's not just, 'Let me hammer you over the head with my offers,' but invite people into that sales process with you when the time is right for them. Think about how you are doing that person a disservice by not showing up. They came to you because they're looking for support or help with a very specific problem, and you could be the person to solve that problem for them. If someone has given you permission to show up in their inbox, you are not spamming them. You are doing exactly what you said you would do." -Bev

About our Guest

Bev Feldman

Kendall Cherry for the Services Guide inspiration

Heart Centered Email Marketing (Previous Episode)

Bev’s Services Guide

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Jessica Lackey

In this episode, we talk about the tension between wanting to be found and being afraid of being stolen from — and why the answer isn’t to publish less. We get into what AI models actually train on, what it means to claim your semantic territory, and why naming your frameworks matters more than ever in an era of linguistic convergence.

We talk about real examples of being ripped off, the myth-busting around AI policies, and why information itself is a leaky moat: what’s worth protecting, what’s worth releasing, and why your discernment — not your information — is what people are actually paying for.

* The first time Jessica was beat-for-beat plagiarized — and why she made the stolen idea a cornerstone of her book anyway

* Why you can’t copyright a concept (only the specific words)

* The myth that AI trains on your private workshops and client conversations

* What an AI policy actually does — and doesn’t — protect

* Claiming your semantic territory vs. resetting your authority every time you post a Reel

* Why naming things (Sacred Sales Hour, Building Blocks, the Beacon Framework) creates findable entities tied back to you

* Linguistic convergence: why everyone in your industry sounds similar, and what to do about it

* Information is a leaky moat — what people are actually buying when they hire you

* Why gatekeeping “the secret” behind an hour-long presentation burns goodwill

* The difference between compounding authority and constantly starting from zero

“I think there’s this tension between I want to be found, in order to be found I must be public, but I want to be credited. And more importantly, I don’t want to be stolen from. And when I say I don’t want to be stolen from, what I mean is I don’t want someone to put their name on my stuff and sell it as their own. But I do want to be found. I do want to be cited. I think I’ve just decided that I can’t do anything about [people taking it] now. The more I put it out there in the world, the more likely it is that someone’s gonna stumble across something I wrote, but I want them to know it came from me. That’s why you need unique terminology, unique nomenclature — that’s hard to replicate, hard to rip off.” — Jessica

Resources

Jessica’s What Business Model are you Running?

Nathan Barry’s The Ladders of Wealth

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Jessica Lackey

In this episode, Jessica walks Meg through the full arc: how the membership started as a 10-lesson video library for 20 superfans, grew to 150+ members with 2-3 weekly events, and what happened when she asked them what they needed now that the membership had grown. She shares the five member profiles she identified, the eight themes Claude surfaced from survey responses, and the new five foundations framework that now anchors the entire onboarding experience.

We talk about what it looks like to redesign something that isn’t broken but has gotten too unwieldy to navigate — and what it cost (including her back) to rebuild it in two weeks. Get a real look at what happens when you’ve been cobbling together gaps with your own presence for two years and then evolve the infrastructure to match.

* Why a membership built for 20 superfans doesn’t automatically work for 150 people who don’t already know your work

* Why the new design wouldn’t work on a smaller scale, and why community needs to evolve

* The five member profiles: Students, Coworkers, Community members, All-ins, and Drop-ins — and why welcoming all five changes how the experience is designed

* What members said about Sacred Sales Hour that Meg immediately called a sales page testimonial

* The eight themes surfaced from 40 survey responses and 10 intervies, and which ones were already suspected vs. actually surprising

* Why “content volume and navigation” is the top friction point — and how Jessica’s new Five Foundations framework addresses it

* Dunbar’s number, capping the membership at ~200, and why some things just shouldn’t scale

* Hiring from within the community — and why that matters when your methodology is the product

* How the Relationship Rhythms course complements and deepens the Membership’s foundations.

“This is copy from Claude, which I enjoy: Most business advice assumes you already know what kind of business you’re running and hands you the route — this content strategy, this sales script, this pricing model. Deeper Foundations starts earlier. The five foundations — business design, marketing, sales, operations, authority building, and planning — aren’t topics to pick from a library. They’re the terrain every sustainable business has to navigate, and this membership covers all five in sequence at the depth you’re at. It’s not proprietary secrets. It’s that Jessica organized the real fundamentals into a coherent system, and then shows up to help you apply it to whatever business you’re actually running and whatever level you’re at in each foundation.” -Jessica

Resources Mentioned

Deeper Foundations Membership

Relationship Rhythms Program (with live Q&A)

Josh Spector’s Clients from Content Membership (the original Membership Inspo!)

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Meg Casebolt

Jessica Lackey

In this episode, we’re joined by Joe Casabona of the Streamlined Solopreneur. Joe has a master’s in software engineering and spent 20+ years as a developer before pivoting to help solopreneurs build systems that let them actually take time off. He’s been deep in the vibe coding world—building iOS apps, beta reader tools, and more—and has strong opinions about what’s worth your time and what isn’t.

We get into what vibe coding actually is, which tools people are using, and how code goes from running in a sandbox to something real people can access. This isn’t a “vibe coding is the future” episode. It’s an honest look at the tradeoffs—security, cost, opportunity cost, and the sneaky way tinkering can start to parade as productivity.

* What vibe coding actually is, and which tools solopreneurs are talking about most (Lovable, Claude Code, Cursor, Codex, Replit)

* How code goes from a thing running on your computer to something actual humans can access and use

* The types of projects that are good candidates for vibe coding—and the ones you should probably leave alone

* What happens when vibe coding gets you to 80% but can’t get you the rest of the way

* Security risks that are easy to miss: exposed API keys, plain text credentials, and more

* HIPAA, PCI compliance, and other reasons to think carefully before vibe coding certain apps—no matter how cool they sound

* The “procrastination parades as productivity” trap, and how to tell if your tinkering is actually serving your business

* Why token costs matter more than most people are factoring in right now

* Joe’s lawnmower test: when just paying for the tool is the smarter move

* The 10-point framework Joe uses before starting any vibe coded project

"When you vibe code something and something goes wrong, it is a very helpless feeling if the AI can't fix it, because now you are taking something that you didn't write that you may not be familiar with. With my iOS app, it was like, 'There's something wrong with P list.' And I'm like, 'What is P list? Like, I don't know what that is. Can you just fix it?' And it's like, no. At some point you will hit this plateau where you can't take the app any further or something is broken. And you either just have to shrug or actually hire a developer to fix it." — Joe

About our Guest

Joe Casabona Website | LinkedIn

Joe's 10-point checklist for coding with AI

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Jessica Lackey

In this episode, Jessica shares her own journey from existential AI FOMO in January (OpenClaw! ClaudeCode! Opus! Oh my!) to a more grounded relationship with which tools actually serve her business. Meg brings her framework on early adopter cycles, the system stress that follows loud hype, and why the people yelling the loudest about a technology are usually trying to prove something—to themselves or to you.

We talk about what friction is actually telling you, the work AI is currently best poised to eliminate, and how to stay informed enough to make good decisions without getting sucked into the daily noise.

* Jessica’s emotional arc from existential AI FOMO in January 2026 to a calmer, more grounded approach—and what actually changed

* Why early adopters yelling about a technology often signals the window of advantage is already closing

* The “friction as signal” reframe: how slowing down through manual processes reveals whether you should be doing something at all

* What AI will realistically eliminate—repetitive, clerical, execution tasks—versus what stays irreplaceable (strategy, point of view, and looking someone in the eye)

* The “glue jobs” problem: roles that hold organizations together without driving revenue directly, and the risk of automating them away before you understand what they do

* How to tell the difference between adopting a tool because you genuinely need it versus keeping up

* Why understanding how a system breaks is more valuable than just using it to generate output—and how building things yourself teaches you that

* How to stay aware enough to make smart decisions without falling into constant FOMO-checking as a business strategy

"The friction slows me down enough to be like, 'This was a poor choice, Jessica. Strategically, I'm asking, am I dragging my feet because it's taking a long time? Or am I dragging my feet because this is not the right move? If you don't drag your feet, you never ask those questions. And I was partway through building out Five Foundations as a suite of courses and I stopped and said, wait—is this actually what I want to do? And the answer was no. The friction gave me the time to figure that out." -Jessica

Resources

TBM 417: Before You Fire All Your Glue People Because of AI

Matt Schumer “Something Big is Happening” Wikipedia page

Citrini’s 2028 Global Intelligence Crisis

The Panel with Justin Jackson and Brian Casel

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Meg Casebolt

Jessica Lackey

Instead of setting up a traditional partnership or agency, Anna and Janel of Strange Birds did something different — they spent a year building out the governance structure of a worker-owned cooperative.

Anna has been running Strange Birds, an idea specialist consultancy for over six years; Janel joined two and a half years ago after leaving Meta — and instead of just adding a second name to the partnership agreement, they restructured the whole business as a worker-owned co-op.

We dig into what a cooperative actually is and why it’s meaningfully different from a standard partnership, what the business case actually looks like (the survival stats are genuinely wild), and how going through the process forced them to have all the money, roles, and “what if someone stops pulling their weight” conversations that most business partners quietly avoid.

* What a worker-owned cooperative actually is — and how it’s legally different from a regular partnership or LLC

* Why 90%+ of co-ops outlast the 10-year mark while most traditional businesses fail within five

* The personal case for co-ops: why the creative services agency model is broken and what a democratic ownership structure actually fixes

* Equal pay, dependents, and the specific messy money conversation they had to have before finalizing their bylaws

* Why the cooperative legal structure took them a year to formalize — and why that’s a feature, not a bug

* How defining clear roles replaced the “we should all be interchangeable” model and made both partners more confident and effective

* What “humans first” looks like in practice when a kidney infection takes someone out for a month

* The structural safety nets they built into their bylaws for future members

* How practicing difficult internal conversations has made them better communicators with clients

* Keeping a 20-year friendship intact when you’re also co-running a business together — and the early warning sign when things start to feel tense

A cooperative model helps make sure we're all not just quote unquote horizontal — which, for people who have worked in horizontal business models, be real: was it actually horizontal? It was not. There was always a boss. Always a boss. There's always someone saying no. This is actually democratic. We all own it. We're all invested in it, and we all get paid equally regardless of if one person's services are bringing in more money — because a rising tide lifts truly all ships in a cooperative."

About our Guests

Strange Birds

Mentioned Resources

Lauren Edwards Flying the Coop episode

Incorruptible by Eric Ries

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Meg Casebolt

Jessica Lackey