OnlyFounders

Anne Gillaspie
  • 4.9 (62)
  • Entrepreneurship

OnlyFounders conversations reveal the explicitly honest truths humans don’t always share publicly while founding something meaningful. Host Anne Gillaspie cultivates a safe space for guests to share their truths openly and honestly with courage, humor, and human connection. You’ll get some f-bombs tossed in for fun as we unravel the millions of founder stories yet to be told. 

  1. 5d ago

    Stop Fearing AI. Start Using It to Be More Human | Anne Gillaspie | Ep07

    What if AI isn't here to replace the human part of your work—but to finally give you more time to actually be human? In this solo episode of OnlyFounders, Anne Gillaspie takes on one of the biggest fears surrounding AI: “Is AI going to replace my job?” Her answer is blunt: f**k no. Anne explores what human-centered leadership looks like in the age of AI, and why the qualities that make people valuable—thought, emotion, empathy, care, creativity, judgment, and the ability to make other people feel seen and heard—aren't things leaders should be trying to automate. Instead, Anne argues that AI should function as a support tool: handling administrative work, organizing information, speeding up repetitive tasks, and giving humans more space to focus on the work only they can do. She shares how she uses AI in her own branding business to transform a process that once took 6–8 hours of intensive brain work into roughly 1–2 hours, while keeping the human judgment and emotional meaning at the center. In this episode, Anne gets into: Why fear of AI replacing your job can actually limit how you use the technology What human-centered leadership really means in an AI-driven workplace Why AI should supplement your brain—not replace it How Anne uses AI to turn 40–60 pages of brand therapy notes into organized, usable brand insights: Why the human meaning behind a founder's story can't simply be automatedHow AI helped Anne reduce a 6–8 hour brand guidebook process to around 1–2 hoursWhy time and attention are more valuable than money for a founder and momHow AI can help leaders become better listeners by removing the need to take notes during meetingsWhy leaders should focus less on generic bonuses and more on actually making their employees' lives easierWhat “surprise and delight” can look like in leadership, culture, and customer experienceWhy founders need to stop giving away their ideas and expertise for freeAnne's philosophy on using AI for good—and for humanity Pull quotes: “AI should be a tool that helps you organize. It should help you with your tasks.” “Time is my greatest value. My attention is my greatest currency.” “I now use AI to be more human in my work.” “Being a human-centered leader requires you to actually be a human.” The conversation ultimately comes back to a simple idea: your humanity is your advantage. Use AI to eliminate the busywork, organize the noise, and create more space for empathy, connection, creativity, leadership, and the work that actually matters. Watch this episode on our YouTube channel: https://www.youtube.com/@onlyfounders.podcast  Subscribe on Spotify: https://open.spotify.com/show/2PuNBpWpZKzCnuwmFQOPI4?si=97a26df7e350478a Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/onlyfounders/id1832541527 Follow Anne Gillaspie on Instagram: https://www.instagram.com/annegillaspie/ Follow Anne Gillaspie on LinkedIn: https://www.linkedin.com/in/annegillaspie/ Visit our website: https://theannegillaspie.com/  If this conversation resonated with you, subscribe, leave a review, and share this episode with another founder who needs to hear it.

    Stop Fearing AI. Start Using It to Be More Human | Anne Gillaspie | Ep07

  2. Aug 18

    Enshittification Explains Everything Wrong With Tech Right Now | Sayre Blake | Ep06

    What happens when a classically trained illustrator and electrical engineer decides the answer to AI's biggest problems isn't more data, it's less? Sayre Blake is the CEO and technical founder of SkillSaige, a soft-skills training platform that reimagines corporate learning as an actual video game, built by someone who's directed shipped titles, built enterprise VR training, and helped brands escape "five stock illustrations from 2019" territory. Her AI-powered trainer, Sage, runs a 15-minute conversation on a fraction of the compute most chatbots burn, using less power, she says, than streaming 15 minutes of Netflix, while being explicitly designed to never remember you, bond with you, or pretend to be more than a character in a story. In this episode, we get into: Why "enshittification" isn't inevitable. It's a choice companies keep making anywayThe theater training principle Sayre used to build AI boundaries that actually holdWhy "good-ish" AI might be more dangerous than AI that's just badThe real math behind AI's power problem, and why she thinks the current data center boom won't survive contact with realityRunning a lean, remote-first company without a "corporate culture" clauseWhy she calls most public vulnerability "performative honesty," and why that's a problemSayre also gets brutally honest about the state of SaaS, the video game industry's identity crisis, and why she's not "socially digestible" enough to run for president (her words), but might be building something more useful than a campaign anyway. Pull quotes: "It's almost more dangerous than being outright bad, because it encourages you to keep trying." "We could do this with twelve people instead of twelve hundred." This is a conversation about building tech that knows its own limits, and why that restraint might be the most radical business strategy in the room. Watch this episode on our YouTube channel:  https://youtu.be/t7rvmfvYE_I Subscribe on Spotify: https://open.spotify.com/show/2PuNBpWpZKzCnuwmFQOPI4?si=97a26df7e350478a Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/onlyfounders/id1832541527 Sayre Blake: Website: https://skillsaige.com/ Sayre’s LinkedIn: https://www.linkedin.com/in/sayre-blake/ SkillSaige LinkedIn: https://www.linkedin.com/company/skillsaige   Anne Gillaspie: Instagram: https://www.instagram.com/annegillaspie/ LinkedIn: https://www.linkedin.com/in/annegillaspie/ Website: https://theannegillaspie.com/  If this conversation resonated with you, subscribe, leave a review, and share this episode with another founder who needs to hear it.

    Enshittification Explains Everything Wrong With Tech Right Now | Sayre Blake | Ep06

  3. Aug 6

    The Real Reason Most Founders Never Plan Their Exit with John Taylor | Ep05

    What happens when the guy who built a podcast marketing agency also builds the AI tool designed to make that agency obsolete? John Taylor isn't afraid of the answer. He's already got a number in mind, and the day someone hits it, he's gone. John is the CEO of Act3 Agency, a San Francisco based podcast marketing agency, and the founder of PodAgain.ai, an AI powered podcast promotion and content platform launching in weeks. Act3 already serves podcasters directly; PodAgain scales that same intelligence, including content repurposing, competitor gap analysis, cross show networking, and analytics driven episode ideation, into a self-serve SaaS built to turn static back catalogs into constantly working assets. In this episode, John and host Anne Gillaspie go far beyond the pitch: Why John calls PodAgain his own "self-destruct button," and is fine with itBuilding a company you can sell on purpose, with a life already planned on the other sideWhat 7 months a year on tour (MTV Music Awards included) teaches you about partnership and absenceMarriage, divorce, and being a "cycle breaker" after watching parents make it work for 66 yearsWhere AI should sit in a founder's workflow, as leverage for a human, not a replacement for one John's blunt take on relationships lands just as hard as his take on building: "An affair is not the problem, an affair is a symptom of a problem." And on the exit he's already building toward: "When anybody offers me this number... I will retire, and you will not see me again." This one moves fast between founder strategy and hard-won personal truth, sometimes in the same sentence. Resources and links (John Taylor) LinkedIn: https://www.linkedin.com/in/jtnorcal/ Website: https://podagain.ai/ Agency: http://act3agency.com/ Watch this episode on our YouTube channel: https://youtu.be/-b0BMvv3YRE Subscribe on Spotify: https://open.spotify.com/show/2PuNBpWpZKzCnuwmFQOPI4?si=97a26df7e350478a Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/onlyfounders/id1832541527 Follow Anne Gillaspie on Instagram: https://www.instagram.com/annegillaspie/ Follow Anne Gillaspie on LinkedIn: https://www.linkedin.com/in/annegillaspie/ Join Coffee Club: https://docs.google.com/forms/d/e/1FAIpQLSevT9HVr57sn4fFUVpsWpcO-ZMeQKgftrg19tdVXPPrM5xQIQ/viewform Visit our website: https://theannegillaspie.com/  If this conversation resonated with you, subscribe, leave a review, and share this episode with another founder who needs to hear it.

    The Real Reason Most Founders Never Plan Their Exit with John Taylor | Ep05

  4. Aug 4

    How Saying Yes Built a Business | Elissa Zylbershlag | Ep04

    She built a mentoring program before she knew it was her business. What happens when the thing people keep pulling you aside to do quietly becomes the thing you can't stop building? Elissa Zylbershlag, M.Ed., is the Founder of Work Wise Labs, helping new leaders build the confidence to lead, manage, and hold a room. She's spent 20+ years in professional development, with leadership roles at the Anti-Defamation League, the NJ State Bar Foundation, and the NJ Division on Civil Rights, and she's Certified in Applied Positive Psychology from the University of Pennsylvania. She built her own IP-rich curriculum from scratch and grew her practice from 3 paid programs in 2023 to 7 the next year, all while working full-time. Now she runs monthly public workshops and coaches leaders through the exact confidence gap she's had to close herself. In today's episode, we talked about: • Pricing yourself for the first time, and why "I don't know what to charge" isn't a character flaw, it's a rite of passage •  Why every discount should cost the client something too ("that value is the value") •  The moment she blurted out a service she hadn't built yet, and landed a six-month contract anyway • Bombing a 250-person keynote after crushing the same room two years earlier, and what that taught her about the difference between a facilitator and a speaker •  Her framework for confidence as a fundraising thermometer: insecurity first, then the skill, then the stumble, then the win Pull quotes: "We are all in the same business, and that is the business of making money." "Facilitation is guide on the side. Speaking is sage on the stage." She still doesn't have a will. But she's got a company, a client list, and a keynote she's determined to nail, Toastmasters and all. Resources and links (Elissa Zylbershlag) LinkedIn: https://www.linkedin.com/in/elissazylbershlag/ Website: www.workwiselabs.com Instagram: https://www.instagram.com/workwiselabs/ Watch this episode on our YouTube channel: https://youtu.be/20jKUdIdaQ8 Subscribe on Spotify: https://open.spotify.com/show/2PuNBpWpZKzCnuwmFQOPI4?si=97a26df7e350478a Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/onlyfounders/id1832541527 Follow Anne Gillaspie on Instagram: https://www.instagram.com/annegillaspie/ Follow Anne Gillaspie on LinkedIn: https://www.linkedin.com/in/annegillaspie/ Join Coffee Club: https://docs.google.com/forms/d/e/1FAIpQLSevT9HVr57sn4fFUVpsWpcO-ZMeQKgftrg19tdVXPPrM5xQIQ/viewform Visit our website: https://theannegillaspie.com/  If this conversation resonated with you, subscribe, leave a review, and share this episode with another founder who needs to hear it.

    How Saying Yes Built a Business | Elissa Zylbershlag | Ep04

  5. Jul 28

    The Founder Mindset Nobody Talks About | Paige Arnof-Fenn | Ep03

    "I don't believe in failure. You either learn something, or you're successful. There's no third option." That's the mindset that took Paige Arnof-Fenn from Wall Street burnout to Coca-Cola boardrooms to founding her own branding empire.  Paige Arnof-Fenn is the founder & CEO of Mavens & Moguls, a global branding and digital marketing firm based in Cambridge, MA. Her clients include Microsoft, Virgin, venture-backed startups, and nonprofit organizations. A Stanford University and Harvard Business School grad, she serves on several boards and is a popular speaker and columnist for Entrepreneur and Forbes, but long before the bylines and board seats, she cut her teeth at P&G and Coca-Cola, the two most brand-obsessed companies on the planet, before betting it all on the dot-com wave and never looking back.  In today's episode, we talked about: The two-week gut check that told her Wall Street's paycheck wasn't worth its lifestyleWhy P&G is "marketing boot camp", and why the same rigor that trained her also frustrated herDitching a corporate corner office to become the oldest person in a startup full of skateboards and piercingsRunning guerrilla market research on the beach, same-day data, same-day website changes, decades before "move fast" was a sloganThe hardest lesson of running her own company: knowing when loyalty to early hires becomes a ceiling on growthWhy she uses LinkedIn as a background-check tool, not a highlight reelSeparating self-worth from outcomes, "you either learn something or you're successful"Pull quotes: "What makes a great movie doesn't necessarily make a great career path." "I don't actually believe in the concept of failure. You either learn something or you're successful." From backing out of a Wall Street office building in the '80s to backing herself into an ampersand-branded firm that's outlasted Facebook, Paige didn't just study marketing. She became her own longest-running case study. Resources and links (Paige Arnof-Fenn) LinkedIn: https://www.linkedin.com/in/paigearnoffenn/ Website: https://mavensandmoguls.com/ Watch this episode on our YouTube channel: https://youtu.be/9DkL0LScoZ4 Subscribe on Spotify: https://open.spotify.com/show/2PuNBpWpZKzCnuwmFQOPI4?si=97a26df7e350478a Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/onlyfounders/id1832541527 Follow Anne Gillaspie on Instagram: https://www.instagram.com/annegillaspie/ Follow Anne Gillaspie on LinkedIn: https://www.linkedin.com/in/annegillaspie/ Join Coffee Club: https://docs.google.com/forms/d/e/1FAIpQLSevT9HVr57sn4fFUVpsWpcO-ZMeQKgftrg19tdVXPPrM5xQIQ/viewform Visit our website: https://theannegillaspie.com/  If this conversation resonated with you, subscribe, leave a review, and share this episode with another founder who needs to hear it.

    The Founder Mindset Nobody Talks About | Paige Arnof-Fenn | Ep03

  6. Jul 20

    “I Taught Empathy for Years Before I Used It on Myself” | Rob Volpe | Ep02

    What happens when the "soft skill" everyone tells you to hide turns out to be the thing that built your business? Rob Volpe spent nearly two decades running Ignite 360, a consumer insights and strategy firm he bootstrapped, self-funded, and grew without ever missing payroll — before exiting through acquisition. Along the way he became known as the Empathy Activist, author of the award-winning Tell Me More About That: Solving the Empathy Crisis One Conversation at a Time. His work is built on a simple, contrarian bet: empathy isn't a personality trait for the soft-hearted, it's an underused strategic tool that most leaders have talked themselves out of using. In today's episode, we talked about: • From qualitative researcher to founder, and the "old tapes" that told Rob empathy was a weakness, not a superpower • The contract that said "EMPLOYEE" in all caps, and the full body "no" that ended his path to ever working for someone else • Building Ignite 360 on relationships, not job postings, and why he hired for his own weaknesses first • The clients who wanted empathy in the work but not in the title, and what that says about the current cultural moment • His midlife crisis, the day the acquisition finally closed, and learning his business and his identity were never meant to be the same thing • Letting go of "should" on newsletters, talk titles, and recovery, and trusting his own timing instead "Don't let 'should' get in the way of good." On empathy at work: it's not a bug in the system, it's a feature we were literally born with. Rob spent his career teaching brands to notice what people actually feel underneath what they say. Turns out the hardest person to read that way was himself — and it took a contract, a cat named Domino, and one very loud "no" from the universe to get him there. Resources and links (Rob Volpe) Website: https://www.robvolpe.expert/ YouTube: https://www.youtube.com/@EmpathyActivist Book: Tell Me More About That: Solving the Empathy Crisis One Conversation at a Time: https://www.amazon.com/Tell-More-About-That-Conversation/dp/1774580896/ref=tmm_hrd_swatch_0 Newsletter: https://readingbetweenthelines.beehiiv.com/ Watch this episode on our YouTube channel: https://youtu.be/Rf7C2mbxg3s Subscribe on Spotify: https://open.spotify.com/show/2PuNBpWpZKzCnuwmFQOPI4?si=97a26df7e350478a Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/onlyfounders/id1832541527 Follow Anne Gillaspie on Instagram: https://www.instagram.com/annegillaspie/ Follow Anne Gillaspie on LinkedIn: https://www.linkedin.com/in/annegillaspie/ Join Coffee Club: https://docs.google.com/forms/d/e/1FAIpQLSevT9HVr57sn4fFUVpsWpcO-ZMeQKgftrg19tdVXPPrM5xQIQ/viewform Visit our website: https://theannegillaspie.com/

    “I Taught Empathy for Years Before I Used It on Myself” | Rob Volpe | Ep02

  7. Jul 14

    My Founder Story: Anne Gillaspie on Dying (and Being Reborn) as a Founder | Ep01

    What if the version of you that built your first business had to die for the next one to exist? Anne Gillaspie doesn't think that's a metaphor; she thinks it's happened to her three times. In this first-ever solo episode of OnlyFounders, host Anne Gillaspie steps out from behind the mic and into the story herself. She's the founder and CEO of Fix & Form, a Denver branding firm that's quietly rebuilt itself twice in 12 years, and a keynote speaker whose talks on truth-telling and burnout have started drawing crowds who want more than a business card exchange. This episode marks a reset for the show itself, a pivot from co-hosted banter to raw, unfiltered founder testimony, starting with Anne's own. In today’s episode, we talked about: • From brand manager to solo founder, and her "happy divorce" from her old identity • The three-month depression that accidentally launched her business • Why Fix & Form killed retainer marketing for one-time transformations • Miscarriage, motherhood, and rebuilding herself, more than once • Launching Anne's Coffee Club for founders who want real access "I believe that we have many rock bottoms. I believe that we have to die several times to reinvent ourselves and be reborn in this lifetime." She closes the episode with a story about a single birthday candle — and why, at 41, it was the first birthday she'd ever actually had. Watch this episode on our YouTube channel: https://youtu.be/ELCol0jHRKg Subscribe on Spotify: https://open.spotify.com/show/2PuNBpWpZKzCnuwmFQOPI4?si=97a26df7e350478a Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/onlyfounders/id1832541527 Follow Anne Gillaspie on Instagram: https://www.instagram.com/annegillaspie/ Follow Anne Gillaspie on LinkedIn: https://www.linkedin.com/in/annegillaspie/ Join Coffee Club: https://docs.google.com/forms/d/e/1FAIpQLSevT9HVr57sn4fFUVpsWpcO-ZMeQKgftrg19tdVXPPrM5xQIQ/viewform Visit our website: https://theannegillaspie.com/ If this conversation resonated with you, subscribe, leave a review, and share this episode with another founder who needs to hear it.

    My Founder Story: Anne Gillaspie on Dying (and Being Reborn) as a Founder | Ep01

  8. Mar 24

    067: Why Not Me? Orly Zeewy on Female Entrepreneurship, the Bubble Wrap Story, and Redefining Failure

    In this episode, Anne and Matt sit down with Orly Zeewy, brand strategist and author of the upcoming book Why NOT Me? The Female Guide for Entrepreneurship, to unpack the unique challenges women face when building a business. Orly shares the story of her book's title—born from the universal imposter syndrome of "Why me?"—and explains why female founders need to embrace failure as feedback rather than a reflection of their self-worth. They also explore the dangers of "ugly babies" in business, including the surprising origins of bubble wrap. The group discusses why over-coaching can paralyze your progress and the flawed pricing mentalities that hold so many female entrepreneurs back. Whether you are navigating product-market fit or learning how to stand firmly in your zone of genius, this conversation is a masterclass in pivoting with purpose and finding your community. 🚨 Stuff You’ll Want to Remember: "Perfection is the enemy of good. This is what I hear from women all the time." — Orly"Do not let coaching stall the doing." — Anne"Failure is the whole, is the backbone of entrepreneurship. Because if you don't fail, you don't grow." — Orly"Just because it comes easily to you does not mean it has no value." — Orly📡 Where to Find Us Orly Zeewy → Zeewy Brands - LinkedInAnne → Fix & Form - LinkedInMatt → ChipBot - LinkedIn

    067: Why Not Me? Orly Zeewy on Female Entrepreneurship, the Bubble Wrap Story, and Redefining Failure
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4.9
out of 5
62 Ratings

About

OnlyFounders conversations reveal the explicitly honest truths humans don’t always share publicly while founding something meaningful. Host Anne Gillaspie cultivates a safe space for guests to share their truths openly and honestly with courage, humor, and human connection. You’ll get some f-bombs tossed in for fun as we unravel the millions of founder stories yet to be told. 

Information

  • Creator
    Anne Gillaspie
  • Years Active
    2025 - 2026
  • Episodes
    74
  • Rating
    Explicit
  • Copyright
    © 2026 OnlyFounders
  • Show Website
    OnlyFounders

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