the deep dig

where we dig DEEP underneath the nonlinear path that got us to where we are now in our businesses.

Welcome to THE DEEP DIG, a podcast digging deep into the WHY behind what people DO. With entrepreneurship, we often hear about the end result, and the accomplishments, but I’m more interested in the stories underneath those milestones and successes. I'm Bridget Baker, of bridget baker branding, your emcee. Come with me as we uncover why people do what they do, and why they are uniquely qualified to support you in that. I’m a brand and website designer who's almost incapable of small talk, and loathes the saying "it's not that deep." If you nerd out on having a business, evolving a business, and keeping at it when business feels tough, this podcast is for you. Let’s. Get. DEEP. thedeepdig.substack.com

Episodes

  1. 6d ago

    What is an SOP anyway? with Jacki Hayes

    My guest today is Jacki Hayes (she/her) is a systems strategist and project manager for website designers in the messy middle - overwhelmed by running the business and less time for focused creative work. She was also the host of the podcast Here’s What I Learned, which ran from March 2021 until April 2026. This wide-ranging conversation about running a sustainable, spacious business — one that actually feels good to show up for, and using your strengths — and getting your systems set up so you can do your creative work. Jackie shares how she helps clients move from frantic, reactive days to ones with real breathing room. A key insight: she asks clients about their favorite day rather than their ideal day — because “ideal” invites judgment and “shoulds,” while “favorite” grounds you in something real and achievable. The conversation covers: SOPs (Standard Operating Procedures) — what they are, why every business owner needs them even if you’re solo, and how the humble peanut butter sandwich is the perfect metaphor for why unclear instructions fail. Time tracking — why brain-dumping everything you do for two weeks every quarter is one of the most eye-opening exercises you can do, and how it reveals where you’re spending energy that isn’t moving the needle. Hiring smart — why a VA isn’t always the right first hire for service providers, and how bringing on an assistant in your actual craft (design, social media, etc.) can free up far more of your time. Tools & systems — Jackie’s “tool agnostic” philosophy, why you should always try a tool for 90 days before buying the annual plan, and the hidden cost of switching tools. Emergency SOPs — what happens to your business if you’re suddenly out for a week, a month, or permanently, and how to create a simple contingency document before you need one. AI in your workflow — how Jackie uses Claude to turn Loom walkthroughs into drafted SOPs, and why using AI as an editor rather than a writer is often a far better use of your time. Find Jackie: WEBSITE: jackihayes.co THREADS: @jackihayes_obm EMAILS: jackihayes.co/subscribe Listen to Bridget’s episodes on Jackie’s podcast, Here’s What I Learned (100+ episodes in the archive). This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thedeepdig.substack.com

    What is an SOP anyway? with Jacki Hayes
  2. Aug 2

    This one's got owning a knitting magazine, decorating cakes, and therapy in book form with my guest: Kate Gilbert

    The Deep Dig Podcast Episode: This one's got owning a knitting magazine, decorating cakes, and therapy in book form with my guest: Kate Gilbert Kate Gilbert is a business coach, certified GHL expert, and the author of Social Media Group Therapy, a book for small business owners who know they need to post but just don't want to. She's been called a "hand-holder/butt-kicker" by her clients, which is honestly a pretty accurate description of her supportive but no BS style. Kate’s road to coaching started back in 2008, when she founded and ran her own online knitting magazine for a decade — work that ended up changing how the whole industry paid designers. A decade later, after burnout, single motherhood, and a cancer diagnosis, she stepped away, took a university job, and then the pandemic happened. Suddenly everyone she knew needed help figuring out how to run a business online. She started taking calls. It became the best part of her week. Someone finally asked why she wasn’t charging for it, and — boom. Business. We also get into: being the person you needed — Kate coaches the way she wishes someone had coached her, back when she was running the magazine solo. you can’t read the label from inside the jar — why even the people who give the best advice still need someone else in their corner. dressing for yourself, not for a gaze — a black jumpsuit, a redrafted pattern, and a mini meditation on what your closet says about who you’ve been and who you’re becoming. her book, Social Media Group Therapy — out now on Amazon, and it’s not another content calendar. It’s the anxiety, the comparison spiral, the avoidance — the actual emotional mess underneath “just show up online.” Includes her manifesto process, which she uses with every coaching client to find their real brand voice. Kate’s reframe, and honestly the whole point of this episode: if you’re not showing up, you’re not protecting anyone. You’re just keeping the people who need you from knowing you exist. find kate: kategilbert.com IG @kategil Book: Social Media Group Therapy: From Anxiety to Action: a no-BS social media reset for real results on socials This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thedeepdig.substack.com

    This one's got owning a knitting magazine, decorating cakes, and therapy in book form with my guest: Kate Gilbert
  3. Jul 27

    The Deep Dig Podcast: The One Where Brian Perry Compares Ai to Sex

    pisode Summary Bridget welcomes Brian Perry — authentic communication coach, singer-songwriter, and one of her favorite newsletter writers anywhere — for a conversation that goes deep fast and stays there. Brian describes himself as being in a reinvent stage, though he’s quick to note that reinvention has basically been his whole career. The people Brian works with are grown-ups who’ve gotten very good at adulting — checking all the responsibility boxes, being a different person in every room they walk into — and who arrive at a point where they urgently need to finally write the book, give the talk, open the business, or have the big conversation. What they discover is that somewhere along the way, sounding like themselves has become the scariest thing they could do. Brian’s job is to help them find their way back. The conversation covers: Tuning the radio — Brian describes his coaching like dialing an old analog radio. You’re listening through the static, past all the stations that are clearly wrong, for the signal that’s unmistakably yours. The work happens in the space between the I don’t knows and the I absolutely knows. The once-in-a-lifetime story — Brian’s central belief is that every person has a story only they can tell, and when they live it out loud, they lift everyone around them. He acknowledges this doesn’t land with everyone he says it to — partly because people genuinely believe they’re boring, and partly because uniqueness has been said so many times it’s lost its charge. But the reason it’s true hasn’t changed. Pain as knowledge — Brian weaves together Epictetus (we’re not disturbed by things, but by the view we take of them) and a Jerry Seinfeld conversation with Trevor Noah about pain being knowledge rushing in to fill a gap. The stub-your-toe example: now you know there’s a table there. For Brian, this reframe changed everything — not just intellectually, but as a way of actually moving through uncertainty as a creative entrepreneur who has never once had a 9-to-5. Bell’s Palsy and the return — Brian shares publicly for one of the first times that he had Bell’s Palsy — a virus that attacks the facial nerve and creates temporary paralysis on one side of the face — not once, but three times, switching sides. At a moment when he had just decided to get back up, start speaking again, start making music again, his voice changed in ways he couldn’t reverse. He pulled back. He got quiet. And then, during the pandemic, he found a songwriting community called Thinking Outside the Blocks (Allie Moss and Bess Rogers), which helped him fall in love with the music he could make now, and slowly, trust his voice again. The Indigo Girls and not being done — watching Emily Salyers of the Indigo Girls announce that the voice she was known for was gone — and that they were going to find a way to keep going anyway — was the moment Brian looked at his guitar and decided he was done playing dead. The Martian — the conversation lands on the scene where Matt Damon, stranded on Mars and out of options, wraps himself in a blanket and says: I’m not dying here. And then the montage begins. Brian’s point: in movies the hard part takes two and a half minutes. In life it takes two and a half years. But the moment of deciding you’re not done — that something else gets to show itself in the dark — that’s the pivot. AI as a quickie — Brian offers what might be the most memorable AI analogy on this podcast so far. He’s a fan of sex. He’s not a fan of only quickies. AI is the quickie: useful, even great in the right context, but not a substitute for the messy, slow, vulnerable, collaborative, human process of actually figuring out what you have to say. When you let AI write for you, people aren’t responding to you — they’re responding to something that doesn’t know the text. What Brian is building — YouTube and Substack, developed more intentionally going forward, focused on authentic voice, navigating uncertainty, and permission to just be making it up as you go. Find Brian: yesbrianperry.com | on Instagram, on Substack, and on YouTube References The Indigo Girls Stoicism Epictetus The Martian This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thedeepdig.substack.com

    The Deep Dig Podcast: The One Where Brian Perry Compares Ai to Sex
  4. Jun 26

    The Deep Dig Podcast: The One Where Tracy Stanger Breaks Down the Most You Way to Do Business

    The Deep Dig Podcast Episode: The One Where Tracy Stanger Talks Doing Business Your Way Guest: Tracy Stanger (she/her) Host: Bridget Baker (@bridgetbakerbranding) Find Tracy: Instagram @tracy.stanger | tracystanger.com Episode Overview Tracy Stanger — business coach, questioner, and future author — joins Bridget for a wide-ranging conversation about rejecting the "right way" to run a business, building your offers and marketing around your actual personality, and why the most radical business move might be simply doing things your way. What We Cover The Current Mood Tracy opens by admitting she's pissed off — and that anger is fuel. She's been deep-diving into off-grid living (voltage, amperage, food storage), questioning every system in business, religion, and government, and channeling all of it into her upcoming book, The Most You Business Book. The Business Guru Cycle The conversation digs into a frustrating pattern: big-name coaches selling you "the secret to business" — then years later telling you everything they taught you is now dead, and selling you the new secret. Sound familiar? Bridget and Tracy compare it to fashion trends: everything cycles. Knowing that frees you from chasing it. Personality Typologies as a Tool (Not a Box) Tracy uses frameworks like Gretchen Rubin's Four Tendencies, DISC, Clifton Strengths, and the Enneagram in her work — but not as rigid labels. She's a Questioner (Four Tendencies) and an Enneagram 1, and she's clear that these tools shift over time based on stress, life circumstances, and growth. The point is to use them to find your way, not to lock yourself in. The Work Tracy Does Her offer, The Space You Want, includes: Most You Biz Space — her entry-level community, built around the Sort, Purge, and Organize course The Junk Drawer — a small cohort format for working through it together 1:1 Coaching via Voxer — async, on your schedule, because she's never wanted to do 10 Zoom calls a day (or any, really) The Voxer model wasn't just a workaround — it was a deliberate choice made when she had a one-year-old and couldn't reliably be anywhere at a specific time. And it turns out her clients love it for the same reason: when you're in the middle of a crisis, you don't want to wait until Thursday's call. Why "Sort, Purge, and Organize"? Think of it like a home organizer coming to your kitchen. You pull everything out, look at what's actually in there, and figure out what you've been hiding in the garage that you wish you had space for. In business terms: what are you actually doing, what do you actually want, and what revenue do you actually need to support the life you want — not the life a coach told you to want. The 10K/Month Trap Both Bridget and Tracy push back on the default metric of "make 10K a month" (or 7 figures, or now apparently 8 figures). Tracy's work helps people figure out their number — which might be $3K, might be $15K — and then reverse-engineer an offer and a marketing approach that actually fits. One client realized she only needs to sell 7 of her premium offers per year. That's her scaling strategy, and it energizes her. What AI Can't Do Tracy is openly not into AI. The conversation gets into why: AI can handle the checklist-style coaching that's already too formulaic to be valuable. What it can't do is hear the change in a client's voice when they're in their luteal phase, or notice that the panic spiral at 11pm is cyclical, not a sign to burn the business down. On Writing the Book Tracy has always known she'd write a book. The motivation: she got pissed off that the business book she needed didn't exist. The Most You Business Book is meant to be the antidote to generic business advice — a guide to building offers, marketing, and daily work around who you actually are, not who the gurus say you should be. Living Like You're Already Retired Tracy's been saying since college that she wants to live like she's retired — not waiting until 65 to enjoy her days. The conversation unpacks what that actually means: not quitting work, but building work that fits your life, not the other way around. Quotes to Remember "F**k you to the way business is done — building your offers, your marketing and sales, and literally what you do each day, around you." — Tracy "Or just don't do that shit to begin with. We don't have to pay someone else to do it if it's a thing that doesn't need doing." — Tracy, on the VA-and-AI trend "When you do the thing that is you, it calls in the right people." — Tracy "Life is too short." — Tracy's friend, at 29 Resources & References Mentioned Gretchen Rubin's Four Tendencies framework (Upholder, Questioner, Obliger, Rebel) DISC personality profiles Clifton Strengths (StrengthsFinder) Enneagram The 4-Hour Work Week by Tim Ferriss (and why Tracy has feelings about it) The Devil Wears Prada (the cerulean sweater scene, specifically) Tracy's Sort, Purge, and Organize course inside of the Space You Want Tracy's upcoming Dream Days exercise This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thedeepdig.substack.com

    The Deep Dig Podcast: The One Where Tracy Stanger Breaks Down the Most You Way to Do Business
  5. Jun 16

    The first episode of .. the deep DIG podcast

    Episode 1: The Business That Found Katy Miller Welcome to the very first episode of The Deep Dig! And what a full-circle way to kick things off — my guest Katy Miller of The Miller Social is the person who had me on her podcast years ago, so it only felt right to return the favor. Katy Miller is a learning experience designer who helps entrepreneurs turn their expertise into digital offers like courses, trainings, or product suites. She's the founder of The Miller Social and host of Katy Calls BS podcast. Katy is known for combining strategy, structure and her no BS approach. She's a single mom to two boys, can't start the day without coffee, and loves Taylor Swift. Her top values are: Empowerment, Honesty, Innovation, Practicality, Motherhood or Parenthood, Respect, Education In this conversation we get into all of it: burnout, boundaries, the winding road that led Katy from "I'm going to be a classroom teacher" to "wait, I forgot I have a master's degree," and why building a digital product might be the best business preparedness move you're not making. What we dig into: How Katy went from social media manager → strategy → course designer (and how burning out became the turning point) Why she almost forgot she had a master's in instructional design — and what finally made her lean all the way in The biggest misconception about courses: you can't just build it and wait for money to appear Why the content isn't the problem — it's how your audience needs to receive it The course platform conversation: you don't actually need one (yes, really), and if you do invest, what to look for Why Katy considers digital products a "safety net" — and why you should build yours before you need it Her personal anti-burnout stack: mental health runs, house projects as digital detox, and firm boundaries around access and weekends Connect with Katy: Website: themillersocial.com Instagram: @themillersocial Podcast: @katiecallsbs My episode on Katy Miller's podcast aired January 22, 2024 on the Real Background of Branding. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit thedeepdig.substack.com

    The first episode of .. the deep DIG podcast

About

Welcome to THE DEEP DIG, a podcast digging deep into the WHY behind what people DO. With entrepreneurship, we often hear about the end result, and the accomplishments, but I’m more interested in the stories underneath those milestones and successes. I'm Bridget Baker, of bridget baker branding, your emcee. Come with me as we uncover why people do what they do, and why they are uniquely qualified to support you in that. I’m a brand and website designer who's almost incapable of small talk, and loathes the saying "it's not that deep." If you nerd out on having a business, evolving a business, and keeping at it when business feels tough, this podcast is for you. Let’s. Get. DEEP. thedeepdig.substack.com