Anniepreneur Presents

Annie P. Ruggles
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  • Entrepreneurship

Anniepreneur Presents is a collection of video shows for the boldly self-employed. The freelancers, creatives, and one-person empires where the business content is completely original, occasionally unhinged, and delivered with enough humor to make it stick. Hosted by Annie P. Ruggles, the show is actually seven shows: Accentuate Your Brilliance, where nonfiction authors read their own work in accents they didn't choose. $queaky Clean Money, where financial experts dismantle the misconceptions quietly wrecking your relationship with money. Self-Care, Unmasked, where guests have genuinely candid conversations while wearing literal sheet masks. Meet Your Metrics!, where one terrifying number gets explained like you're a smart adult who just never had anyone break it down before. Over Our Heads, where strategists under 5'5" deliver five-minute masterclasses with mischief. SaaS w/ Sass, where software founders show you the tool that actually solves your problem. And The Cringe, where small business owners call in to confess their most spectacular missteps, told in their own words. Anniepreneur Presents is the strategy cabaret for the boldly self-employed. Shows, events, and more at anniepruggles.com.

Episodes

  1. 17 Jun

    $queaky Clean Money: Stop Saying 'Relationship with Money' with Audrey Godwin of Whole Soul Finance

    Audrey Godwin wants you to stop having a “relationship” with money... and start getting real about what legitimately matters. EPISODE SUMMARY: We talk about our “relationship with money” like it’s a person, but what if that’s just blocking us from the genuine healing and clarity we need? In this episode of Squeaky Clean Money, Whole Soul Finance creator Audrey Godwin challenges everything you think about money, value, and the role money actually plays in your life. Annie P. Ruggles and Audrey Godwin get deliciously vulnerable about unhealthy patterns, longing, self-worth, and the practical first steps you can take to finally clean things up...without making it a math exercise. KEY TAKEAWAYS: - Money is not a person, friend, or enemy; it's a tool or symbol we use to fill other gaps in our lives. Your “relationship” is really about your relationship with yourself [02:16] - Personifying money (thinking of it as comfort, love, validation, etc.) can allow us to remain dishonest and delusional with ourselves [07:04] - When you feel unsafe or unstable, values and priorities work can feel impossible, but it’s key for taking control of your financial life [13:05] - Being grateful for what you have and content in your present lets you set healthy goals, rather than getting trapped in longing and lack [16:13] - Stewarding money well is not about number crunching; it’s a leadership development exercise. Get honest about your actual values, priorities, and what you stand for. Only then can your financial decisions support a life you want [22:07] - If you’re in a partnership (marriage or business), don’t skip the conversation. Values, priorities, and open communication are the foundations of healthy money choices [24:20] SQUEAKY CLEAN MANTRA: "Stewarding money and wealth well is really a leadership development exercise." — Audrey Godwin [25:06] GUEST BIO: Audrey Godwin is the creator of Whole Soul Finance, a platform helping women align their money with their identity, priorities, and values. A former CPA and CFO, she’s helped hundreds of women build wealth without losing themselves, blending tough clarity with deep compassion. Her signature "position for profit" framework empowers women to make money moves in wholeness, not hustle. Find her at wholesoulfinance.com and on socials as @audreylgodwin. If this episode made you question how you treat money—and what you’re really working for—come find your next move: anniepruggles.com/will-this-sell --- Anniepreneur Presents is the strategy cabaret for the boldly self-employed. Shows, events, and more at anniepruggles.com.

  2. 21 May

    Over Our Heads: Podcast Guesting Demystified by Gini Trask (5'4")

    Gini Trask had five minutes to change how you think about lead generation. Spoiler: she didn't need them all. EPISODE SUMMARY: Podcast guesting isn't a nice-to-have. It's a lead generation system that keeps working years after you record. In this episode of Over Our Heads, strategist and speaker coach Gini Trask breaks down exactly why podcast listeners are more qualified than your social media followers — and the three mistakes that are probably costing you leads every time you appear as a guest. KEY TAKEAWAYS: • Podcast listeners average $75K+ income and a 4-year degree — more qualified than most paid ad traffic • The bathtub analogy: social posts are one faucet that stops when you stop. Podcast appearances are 100 faucets that keep flowing • Three mistakes killing your podcast leads: weak lead magnet, burying your URL, not taking listeners on the journey • Ebooks are dead. What converts from podcasts: done-for-you resources with a simple, memorable URL • One client earned a $300K deal from a podcast recorded three years prior — these appearances have a long tail GUEST BIO: Gini Trask is a speaker coach and podcast guesting strategist who helps entrepreneurs build lifetime lead flow by getting on two podcasts a week. She's grown multiple businesses from incubation to multi-millions and now teaches founders to do the same. Find her at greatleadmagnet.com. If this episode made you wonder whether your own offer would land with a room full of people rooting for you — come find out. anniepruggles.com/will-this-sell - - - Anniepreneur Presents is the strategy cabaret for the boldly self-employed. Shows, events, and more at anniepruggles.com.

  3. 21 May

    Accentuate Your Brilliance: Joy-Full AF with Dr. Erin Burgoon

    Dr. Erin Burgoon read a passage about rest and courage as a Valley Girl... or rather, a Valley They, and somehow it was the most convincing version of the argument you'll ever hear. EPISODE SUMMARY: Joy is the thing most of us got into business for and the first thing we sacrifice once we start chasing metrics. In this episode of Accentuate Your Brilliance, social psychologist and executive coach Dr. Erin Burgoon talks about why happiness and joy are not the same thing, why treating joy like a gas tank you run on empty is a terrible strategy, and why keeping that reservoir topped off every single day is what makes businesses last for decades. Then they read from page 194 of Joy-Full AF as a Valley Girl. Like, totally. THE BOOK: Joy-Full AF: The Essential Business Strategy We're Afraid to Put First by Dr. Erin Burgoon KEY TAKEAWAYS: • Joy and happiness are not the same thing. Happiness is outcome-dependent and spikes when things go well. Joy is a state of being you can practice every day regardless of outcomes. • Most entrepreneurs treat joy like a gas tank they'll fill up when they hit empty. The smarter strategy is keeping that reservoir topped off constantly so you have reserves when things get hard. • Nobody who stayed in business for 30+ years says they survived by being miserable. The ones who lasted found the joy. • Joy doesn't have to be compartmentalized. You don't have to store it up at home and spend it at work. You can find ways to be in your joy inside your business every single day. • The four ingredients of joy: curiosity, connection, creativity, and courage. VIEWER CHALLENGE: Pick one of the four C's of joy (curiosity, connection, creativity, courage). Find the tiniest thing you can do in that area today. Then see if you can make it even tinier. GUEST BIO: Dr. Erin Burgoon (Dr. Erin B) is a social psychologist, executive coach, and bestselling author of Joy-Full AF. They work with leaders at the moment when what they've built stops being able to carry them forward. They built the Integrated Leadership Operating System (ILOS) and have helped leaders survive billion-dollar cuts, double the size of their firms, and turn one-person shops into international operations. Find them at drerinb.com. If this episode made you wonder whether your own offer would land with a room full of people rooting for you, come find out. anniepruggles.com/will-this-sell - - - Anniepreneur Presents is the strategy cabaret for the boldly self-employed. Shows, events, and more at anniepruggles.com.

  4. 21 May

    Self-Care: Unmasked - The Hardest and Most Effective Form of Self-Care with Jennifer Urezzio

    Jennifer Urezzio showed up in a possibly expired sheet mask, put on her glasses over it, and then told us the hardest self-care truth most of us are avoiding. EPISODE SUMMARY: We tend to think self-care means spa days and face masks and getting our nails done. And those things are great. But according to Soul Language founder Jennifer Urezzio, the easiest and hardest form of self-care is the same thing: learning to profoundly love and accept yourself. In this inaugural episode of Self-Care, Unmasked, Jennifer and Annie talk about why we use self-criticism as a fake protection technique, why we get stuck in the rearview mirror, and what it actually looks like to give yourself a clean slate every morning. KEY TAKEAWAYS: • The most effective self-care is also the simplest: learning to profoundly love and accept yourself. We tend to skip that part and go straight to the massage table while berating ourselves internally. • Self-criticism is a protection technique that never actually works. We think if we remind ourselves how badly we messed up, we won't repeat the pattern, but it actually keeps us stuck. • We've been taught to learn through struggle and pain, so we mistake self-punishment for progress. It's not progress. It's a wheel. • All modalities (therapy, breathwork, meditation, screaming in your car) do the same thing: they remind us we're whole and complete. If whatever you're using isn't doing that, ditch it. • Sometimes you need a release. Jennifer screams. Annie screlts (scream-belts Lilith Fair anthems on the highway). Both are valid. SELF-CARE CHALLENGE: Look at yourself in the mirror every morning, look yourself in the eye, and say: "No matter what I think of myself, I still love and accept myself." GUEST BIO: Jennifer Urezzio is the founder of Soul Language, a system for consciously connecting to your soul and having words for your inner truth. She is an intuitive strategist who helps clients decode their divine operating system and move into unapologetic alignment. Find her at soullanguage.us. If this episode made you wonder whether your own offer would land with a room full of people rooting for you, come find out. anniepruggles.com/will-this-sell - - - Anniepreneur Presents is the strategy cabaret for the boldly self-employed. Shows, events, and more at anniepruggles.com.

  5. 21 May

    Meet Your Metrics: The 3 C's of Book Proposals with Debra Eckerling

    Debra Eckerling just explained the entire nonfiction book proposal process so clearly that a nine-year-old could follow it. Which is good, because Annie is apparently the height of one. EPISODE SUMMARY: Most people think you need a finished book before you can get a publishing deal. You do not. What you need is a book proposal, and in this episode of Meet Your Metrics, Debra Eckerling (the book proposal expert, literally the domain name) breaks down the three C's that make up every successful nonfiction book proposal: concept, context, and content. She also obliterates several publishing myths along the way, including the ones about needing six figures to get started and needing three years to see your book in print. BROUGHT TO YOU BY The letter C! KEY TAKEAWAYS: • Most nonfiction books are sold via book proposal, not a finished manuscript. You need a clear idea and a plan, not 90,000 completed words. • The three C's of a book proposal: Concept (what is this book, what makes it unique, why you need to write it), Context (who you are, your platform, your marketing plan, audience research, and comp titles), and Content (table of contents, detailed outline, and 2-3 sample chapters). • You don't need a massive online following. One of Deb's clients is on the board of five organizations full of her ideal readers, and that offline presence was enough to land an agent. • Comp titles are books similar enough that the same reader would buy both, but different enough that your book fills a hole. If you can't figure out your differentiator, do the comp title research first. • Deb wrote all three of her traditionally published books in under three months each, because the proposal was the roadmap. The proposal does double duty as both sales document and writing blueprint. • It does not cost $100,000 to get a book deal. It also does not require a five or six-figure advance to be worth pursuing. If you plan to outsell your advance, the advance number matters a lot less than you think. GUEST BIO: Debra Eckerling is the book proposal expert, award-winning author, and speaker. She is the creator of The DEB Method for Goal Setting Simplified and the author of Your Goal Guide (IPPY silver medal winner) and 52 Secrets for Goal Setting and Goal Getting. She hosts Goal Chat, Taste Buds with Deb, and the Book Proposal Podcast. Her next book, Active Grandparenting (co-authored with Kristen Cofield), comes out fall 2026. Find her at thebookproposalexpert.com. If this episode made you wonder whether your own offer would land with a room full of people rooting for you, come find out. anniepruggles.com/will-this-sell - - - Anniepreneur Presents is the strategy cabaret for the boldly self-employed. Shows, events, and more at anniepruggles.com.

  6. 21 May

    $queaky Clean Money: Top Line vs. Profit with Gwen Bortner

    Gwen Bortner has four decades of business wisdom and she used them to destroy the number you've been bragging about on Instagram. EPISODE SUMMARY: That top-line revenue number everyone posts about on social media? It's not lying, exactly, but it's definitely not telling you the whole truth. In this episode of Squeaky Clean Money, business advisor Gwen Bortner breaks down why income alone is a dangerously incomplete metric and walks you through the four numbers that actually tell you whether your business is healthy or slowly breaking down behind the scenes. KEY TAKEAWAYS: • Your top-line income number is the easiest number to find, which is exactly why we over-rely on it. Easy access does not equal accurate picture. • Someone whose sales dropped $10,000 but whose cost of sales dropped $20,000 is actually further ahead, not behind. The number you're panicking about might be the wrong one. • The four numbers to watch: income, cost of goods/sales, gross income (income minus cost of sales), and profit. You don't need calculus. You need to read a chart. • More income does not mean more money in your pocket. You can absolutely grow your revenue while shrinking your profit if expenses are outpacing sales. • You don't have to look at every line item every day, but you should be reviewing these four numbers monthly and looking at how they move in relation to each other. SQUEAKY CLEAN MANTRA: "Income is important, but profit is what's in your pocket." GUEST BIO: Gwen Bortner is a business advisor with four decades of experience across 47+ industries. She works with women who appear successful but are privately wondering how long they can maintain their current pace. She helps entrepreneurs find the bottlenecks others miss and build businesses that perform without consuming their lives. Find her at everydayeffectiveness.com. If this episode made you wonder whether your own offer would land with a room full of people rooting for you, come find out. anniepruggles.com/will-this-sell - - - Anniepreneur Presents is the strategy cabaret for the boldly self-employed. Shows, events, and more at anniepruggles.com.

  • 6 Episodes

About

Anniepreneur Presents is a collection of video shows for the boldly self-employed. The freelancers, creatives, and one-person empires where the business content is completely original, occasionally unhinged, and delivered with enough humor to make it stick. Hosted by Annie P. Ruggles, the show is actually seven shows: Accentuate Your Brilliance, where nonfiction authors read their own work in accents they didn't choose. $queaky Clean Money, where financial experts dismantle the misconceptions quietly wrecking your relationship with money. Self-Care, Unmasked, where guests have genuinely candid conversations while wearing literal sheet masks. Meet Your Metrics!, where one terrifying number gets explained like you're a smart adult who just never had anyone break it down before. Over Our Heads, where strategists under 5'5" deliver five-minute masterclasses with mischief. SaaS w/ Sass, where software founders show you the tool that actually solves your problem. And The Cringe, where small business owners call in to confess their most spectacular missteps, told in their own words. Anniepreneur Presents is the strategy cabaret for the boldly self-employed. Shows, events, and more at anniepruggles.com.

Information

  • Creator
    Annie P. Ruggles
  • Years Active
    2026
  • Episodes
    6
  • Rating
    Explicit
  • Copyright
    © 2026 Annie P. Ruggles
  • Show Website
    Anniepreneur Presents