Aggressively Human: Online Business in the Age of AI, Algorithms & Automations

In this riffy, delightfully unstructured episode, Jessica and Meg ditch the outlines, frameworks, and “polished” content in favor of a real-life check-in, some AI trivia, and a sneak peek at Jessica’s summer program, Relationship Rhythms.We talk about how building relationships is about more than just dropping into people’s inboxes—and how Relationship Rhythms is designed to bring playfulness (and prizes!) back into the process. Jessica shares why she’s finally running an asynchronous offer and how Relationship Rhythms is different from her usual programs, plus what happens when you go from dreaming to launching.We also get real about our own partnership: the messy business of joint ventures, what happens when your business is in a different gear than your friend’s, and how to talk about money and collaboration in a way that feels human.And because she couldn’t resist, Meg quizzes Jessica on AI trivia—highlighting the joys, the contradictions, and the occasional panic about what AI knows, what it doesn’t, and how we’re using (and refusing) it in our own businesses.If you’ve ever felt like your business friendships are an ever-evolving dance—or wondered how to balance AI curiosity with human connections—listen in. 🍊PS. If you made it to the end of this episode, drop our Easter Egg word on Substack as a comment to let us know you’re here for the rambles, not just the frameworks.* Jessica’s summer program, Relationship Rhythms, and how it’s ushering in a more experimental vibe.* How Relationship Rhythms uses gamified accountability (yes, with prizes) to make relationship building fun* Why Jessica and Meg decided not to monetize the Substack—yet—and the honest convo about splitting podcast revenue* The challenges of co-hosting a podcast when your businesses are in different seasons (and speeds)* The messy beauty of relationship building: why some outreach grows instantly while others marinate for months* Meg’s AI trivia quiz: from radiologists to Reddit, from ChatGPT’s energy usage to recipes with random ground beef* Why learning how to learn will still be a critical skill, no matter about AI’s capabilitiesBloom’s TaxonomyJoin Relationship RhythmsSign up for the waitlist or join the program (opens June 9).Connect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg CaseboltJessica Lackey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com

Have you ever sat through a slide deck that felt like death-by-bullet-point? Or tried to sound like a LinkedIn thought leader only to bore yourself?Have you ever struggled to consider yourself “interesting” when you haven’t gone to space or climbed a mountain?Most importantly, how can you tell a story that AI cannot replace?Story coach and speaker whisperer Mike Ganino joins us to talk about how to actually connect with other humans through storytelling, public speaking, and intentional presence. We talk about what’s missing when AI writes your copy, how to make your keynote more than just a case study, and why the most aggressively human thing you can do is show up—with your voice, your weirdness, and your body and breath. We talk about what job AI can’t do, why “tell your story” is often the worst advice, and how the most impactful stories usually come from Tuesdays, not TED Talks.* How to pull stories from your actual life (even if they happened on a random Tuesday)* What ChatGPT can and can’t do—and why public speaking is still a human-only activity* Breaking free from the drip of consumption and embracing the interiority within us and around us.* How to find your “inner interesting”, and how to transform extraordinary tales into relatable, personable stories.* Why “tell your story” is terrible advice—and what to do instead* How book marketing breaks your nervous system and what our favorite GIFs reveal about usAbout our Guest:Mike GaninoMake A Scene: Storytelling, Stage Presence, and The Art of Being Unforgettable in Every SpotlightConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg CaseboltJessica Lackey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com

“And a lot of people say, oh gosh, you know, friendship is so hard because everybody's so busy. I'm so busy, our schedules don't align. Therefore, “friendship is hard”. And I'm like, are you sure about that?Or is it actually that scheduling with busy calendars is hard. Prioritization is hard. Saying no to things so that you can say yes to the things you actually want to say yes to is hard. Those things are hard. But those things aren't friendship and those things are a part of every other part of life as well.” - KatFriendship doesn’t happen by accident in adulthood. And despite what the internet says, it’s not just about “finding your people.” You have to actually do something—and that can feel impossibly hard when your calendar is full and your energy’s shot.In this episode, Jessica and Meg talk with Kat Vellos—UX designer turned friendship expert—about how adult friendships form, why they fizzle, and what gets in the way. We talk about courage (yes, it still matters), frequency, and how friendship isn’t a productivity project—it’s a relationship. We also touch on the uncomfortable truth: as AI creeps further into our inboxes and interactions, it’s easier than ever to think we’re connected—without actually having any real closeness at all.If you’ve ever said, “I want more friends, but…”—this one’s for you.* Why building adult friendship isn’t harder—it just requires different skills* The four foundations of real friendship: compatibility, proximity, frequency, and commitment* What’s actually hard about making friends (spoiler: it’s courage, not conversation)* The social cost of optimizing everything—including how we spend time with people* Why “being too busy” is often a boundary issue in disguise* How Jessica tries to find local friends who want to talk about cold outreach (and the real dilemma of niche interests + neighborhood proximity)* The difference between a friendship activity and a productivity checklist* How to start small, go first, and create connection without waiting for an inviteAbout our GuestKat Vellos is the go-to source for guidance about cultivating meaningful friendships and community. She’s author of the book, We Should Get Together: The Secret to Cultivating Better Friendships. Kat’s writing is read in over 100 countries, and she’s been interviewed by The New York Times, NPR, and many more.What if friendship is easier than you think?The Togetherness ThingMake yourself a Friendship Joy TrainHow to find real friendships online via the algorithmProduct: BFF Builder BundleCourse: Unbusy CampCourse: Platonic Action LabConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg CaseboltJessica Lackey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com

“If you want a sales pipeline, you are responsible for creating it. What we've been told and what we see online is the kind of constant content creation that is designed to bring you clients…so that you can essentially do a lot of marketing to avoid ever having the sales conversation.But the quickest way to make a sale though is to get to that sales conversation as soon as you can and to make sure that it's as qualified as possible."Most of us have been on the receiving end of a terrible cold pitch. Maybe it was a LinkedIn DM pretending to be friendly. Maybe it was an email that made you feel like a number. No surprise—cold outreach has earned its bad reputation.But the truth is: cold outreach isn’t inherently bad. It’s just rarely done well.In this episode of Aggressively Human, we’re joined by sales strategist Jessica Lorimer, who got her start in the kind of sales that makes people sweat: actual phone calls, to actual humans, in actual corporate offices. We talk about what it looks like to sell in a way that’s clear, kind, and effective—without relying on funnels, fake rapport, or endless social media content. She breaks down what still works, what definitely doesn’t, and how to sell in a way that’s honest, respectful, and doesn’t make you feel like a spammer.This episode is part strategy, part sales therapy, and part reminder that you’re allowed to enjoy sales.* Jessica’s origin story: how she sold her way into a boardroom (without a formal invite)* How “being good at sales” actually made Jess feel in the early days of running an online business, and why she shifted from B2C to B2B sales* Why Jess and Meg have both gotten rid of their funnels* The five-step B2B sales framework Jess uses with her corporate clients (and why it works for soloists too)* Why “I sent 10 emails and no one replied” isn’t a valid reason to give up* What you actually need in a cold message (spoiler: not a fake compliment or a pitch)* Why it’s not about “convincing” someone to buy—it’s about showing them it’s worth a conversation* And why selling isn’t about tricking anyone—it’s about being clear, useful, and brave enough to go firstAbout our GuestJess Lorimer | LinkedInSelling to Corporate Podcast - a bi-weekly favorite of Jessica Lackey’s!From Cold to Closed - open through May 18!Connect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg CaseboltJessica Lackey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com

In this episode, we’re talking about play. Hear us riff on the power of play and personality in our lives and businesses. We explore our different expressions of play as children and how it impacts our businesses today (hint: Meg was a dancer and playwright and Jessica loved to tinker with her Erector sets and handwoven crafts. Totally on brand for both of us). We talk we both experiment in our businesses (once we have the foundations in place), including our plans for the summer. We look at play as a regenerative act: one that requires energy and action, but that gives it back to us.And most importantly, you get:* To hear Jessica’s play theme music (at 55:00)* To let us know if you want a Center Stage watch along (because as a millennial creative woman I’m shocked Meg hasn’t seen this seminal film of my 20s!)* To see Jessica literally dancing on a hillside in Switzerland in 2007, because the hills were alive with the sound of music. (only on Substack, so come hang with us there)In today’s episode* Why play isn’t about escape—it’s about energy, iteration, and identity* How we infuse our personal styles into our personal brands* All of the things Meg has learned from the Museum of Play* What our personal play styles reveal about how we lead, build, and rest* Why we don’t play enough in our businesses* Jessica and Meg’s various types of play (and even what we consider play)* Center Stage and what it gets right about discipline, talent, and letting go* How we’re experimenting in public: podcast shifts, newsletter redesigns, and more* Why constraint is the secret to playful business designConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg CaseboltJessica Lackey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com

Automation. Funnels. AI-generated content. Scale at all costs. New leads.You’ve been sold a load of garbage about what it takes to grow a business today. And in this episode of Aggressively Human, we’re getting back to the truth about sales.Max Traylor—agency churn physician and LinkedIn truth-teller—joins us to break down why so much of what passes for “sales strategy” today was never actually working. (It just didn’t matter when money was cheap.)We talk about how most of us have never learned (or needed to learn) real sales skills, why AI and automation are actually doing you a favor by making real humans stand out, and why your best sales strategy is still a damn phone call.We also dive into what real client expansion looks like, how to expand your existing relationships (hint: the word you’ll stop using is “done”), and how agency owners and soloists can rebuild around human relationships instead of implementing software and tools that take us farther away from connections in search of "scale".* The sales myths we’ve been sold by venture-backed tech startups* The difference between "participating in a buying process" and actually selling* The missed opportunity of existing clients and why client expansion is the sales strategy no one talks about* How to start expanding your engagement from day one* Why quarterly business reviews aren’t admin—they're about getting invited to the adult table* How bad automation is making it easier for real humans to stand out* Why we need to become indispensable partners—and how do we do that* The sales "crisis" that was never new—it just used to be easier to hide bad sales processes when the market was hot* Max’s philosophy on LinkedIn: do it for yourself, not for the likes—and why IP creation > audience chasingAbout our GuestMax Traylor: LinkedIn, Website1,000 Routes with Nick Bennett Podcast AppearanceResources MentionedBecoming an Indispensable Partner featuring Steve Lishansky (Beers with Max podcast)Connect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg CaseboltJessica Lackey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com

Dive into the debate on curation vs. creation, where recycled content often pretends to be fresh thought leadership. Discover how intentional curation can elevate your business strategy and enhance your expertise. The hosts highlight the importance of human curiosity in navigating algorithm-driven content and the transformative power of discontent for personal growth. They also share insights on cultivating reliable connections in the business world, emphasizing that quality curation, fueled by community engagement, can lead to greater success.

In the age of AI-generated content, content repurposing, and ideas being “created” with a screenshot of your site, the question of ownership is more urgent than ever:How do you protect what you’ve created when so much of what you’re creating lives online?In this episode of Aggressively Human, we’re joined by Erin Austin, founder of Think Beyond IP, to dig into what intellectual property really is, what you can protect, and how to turn your expertise into an asset—not just a deliverable.If you’ve been asking, “How do I protect my ideas?”—this is the episode for you.* What counts as intellectual property under U.S. law (and what doesn’t)* The difference between copyright, trademark, patent, and trade secret* “But what if someone steals my stuff?”* The moment a copyright becomes enforceable (and how to register it)* What happens when you use AI to write, create, or ideate (and what that means for copyright)* Why most service providers accidentally give away their IP in contracts, and how to fix it* When and how to cite your sources ethically (even when it’s not legally required)* How IP turns your expertise into leverage, whether you're licensing, scaling, or stepping out of the roomAbout our GuestErin Austin, LinkedInThink Beyond IP AI WorkshopWant to be the first to know when the next Masterclass cohort opens? Join the Priority Access List to receive early notifications and secure your spot before public enrollment opens. The paid masterclass is a three-session live training designed for experts with corporate clients who want to harness AI confidently—without legal headaches. Space is limited to ensure a premium, high-value, small-group experience so you get in depth, practical tools and expert legal guidance.Other ResourcesThe Rookie SongConnect with UsListen on SpotifyListen on Apple PodcastsConnect with Meg and JessicaMeg CaseboltJessica Lackey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com

In a world driven by relentless growth, the hosts explore the radical idea of 'sufficiency' over abundance. They present a framework for the 'Zone of Enoughness', emphasizing the importance of aligning business success with personal fulfillment. The discussion covers trade-offs of money, time, and creative autonomy, pushing back against societal pressures. Listeners are invited to reflect on what truly matters in their lives and businesses, advocating for a balance that honors emotional connections and sustainable growth.

Should we stay or should we go?Leaving social media has been an increasingly popular choice in the past few years. But is leaving always the most impactful choice?In this episode, we sit down with Illana Burk, business coach and advocate for human-first business, to talk about the messy middle of visibility, values, and doing business inside systems you didn’t build.Illana shares why she’s choosing to stay on social media; not because she’s ignoring the harm, but because of how social media is an important place our voices can be heard.We unpack the compromises and contradictions that come with trying to do business ethically in a digital world—where every platform is flawed, no choice is pure, and the desire to get it “right” can quietly become a trap. Illana offers a grounded, generous perspective on what it means to market with integrity and show up with care.* Why “just leaving” social media isn’t always the impactful move (and who wins if we do)* The difference between marketing, community, connection, and consumption—and how social media serves each differently* Why nuance, dialogue, and moral compromise are necessary parts of human business* Why being ethical in business doesn't mean doing it perfectly, and what that actually looks like in practice* Why presence—not performance—might be the best use of platforms in 2025* The value of showing up in systems you don’t fully endorse, and how to do so with intentionAbout our GuestIllana BurkIllana Has ThoughtsBread and ButterThe Good Business Podcasthttps://illanaburk.substack.com/p/i-dont-really-love-social-media-butResources MentionedRe-imagining Online Business | Brooke Monaghan & Tristan KatzThe Digital Watercooler is Gone | Amanda NatividadLizzy GoddardConnect with UsJoin us on SubstackMeg CaseboltJessica Lackey This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit aggressivelyhuman.substack.com