Plan Like A Boss | Planning, Productivity, and Strategy for Entrepreneurs

Tonya
  • 5.0 (5)
  • Entrepreneurship

Plan Like a Boss is your go-to podcast for mastering planning, productivity, and strategy as a solo or small business entrepreneur. Each week, you'll get practical tips and real-life insights to help you set smart goals, manage your time, and grow a business that actually fits your life.

  1. 5d ago

    Why Your Business Still Feels Like a Full-Time Job with Kenneth Kollasch

    Your business can’t keep running on instinct, caffeine, and chaos forever and if you’re feeling that strain right now, this conversation is for you. We sit down with Kenneth Kollasch, a certified business coach, third-generation entrepreneur, former franchise operator, and pastor, to talk about what it actually takes to grow a small business without surrendering your sanity. We start with the surprising leadership lessons that show up long before you ever hire your first employee: the dinner table mindset of an entrepreneur family, the pressure and possibility that come with it, and how high-level soccer builds humility that most owners don’t learn until much later. Kenneth shares the moment his grandfather asked one simple question that changed everything, turning a near-pro soccer path into a values-driven choice about family, presence, and long-term purpose. Then we get practical. Kenneth explains why doubling revenue doesn’t have to mean doubling your hours, and why “more volume” is usually the wrong answer when you’re already overwhelmed. We dig into the Small Business Flight Plan approach: diagnosing what’s real (not just what you feel), identifying win points to double down on, and fixing the pain points that quietly wreck marketing, sales, retention, and cash flow. If you’re a solopreneur, running a mom-and-pop shop, or building a small team, you’ll leave with a clearer framework for business systems, sustainable growth, and burnout prevention. If you got value from this, subscribe, share it with a business owner friend, and leave a review so more people can build companies that support their lives instead of consuming them. Learn more about Kenneth: https://kennethcoaches.com/free Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

  2. Aug 27

    How Solopreneurs Can Save Hours Every Week With a Mac

    Your Mac can either be a fancy typewriter or a serious business advantage, and the difference is usually a handful of habits you set up once. We sit down with Damian Schres, the explainer-in-chief at EasyTech and host of the Mac Preneur Podcast, to talk about the practical side of running a lean solopreneur business on Apple gear without chasing every shiny new tool. We start with Damian’s story: a Fortune 500 engineer who took a slow, careful path into entrepreneurship. Instead of quitting overnight, he spent years running mini-experiments, building confidence, and reducing risk before going full-time. If you’re risk-averse, juggling family priorities, or just tired of “go all in” advice, this conversation offers a more realistic roadmap that still leads to freedom and control. Then we get into the fun part: Mac productivity, automation, and AI for entrepreneurs. Damian shares why macOS longevity and security can be a win for small business owners, plus the specific workflows that save time daily, like iCloud-synced Text Replacement for instant emails and repeat replies. We also explore templates for Gmail and client docs, and Damian’s AI setup using API-driven tools like Writers Brew, alongside Mac utilities like PopClip, Apple Shortcuts, and Hazel, including an automation that renames screenshots based on the text inside them. The takeaway is simple: build systems that remove friction, and you buy back hours every week. If you found something you want to try, subscribe, share this with a fellow Mac-using business owner, and leave a review so more solopreneurs can find the show. Contact Damien: https://macpreneur.com/tips Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

  3. Aug 20

    Stop Doing $10 Tasks: How to Reclaim Your Time and Grow Your Business

    In this episode of Plan Like a Boss, Tonya Lawson sits down with business coach and entrepreneur Louis Swart to talk about delegation, productivity, and what it really takes to build a business that doesn’t depend on you for everything. Louis shares the hard lesson he learned after discovering that his first business had little value because he was the bottleneck. That experience changed the way he approached business—and eventually helped him build a company he could step away from and sell successfully. You’ll hear Louis break down his simple “2K rule” for calculating what your time is worth, why spending your day on low-value tasks can quietly sabotage your income goals, and how a single post-it note can change the way you decide what deserves your attention. Tonya and Louis also dig into productive procrastination, the fear of letting go, the importance of focusing on one needle-moving task each day, and how AI can become just another form of shiny-object syndrome when it isn’t tied to a clear business goal. In this episode, you’ll learn: • How to identify which tasks are truly worth your time • Why delegation is essential for building a scalable business • How to stop treating “busy” as a badge of honor • A simple way to calculate the hourly value of your work • How to recognize productive procrastination • Why focusing on one important task can move your business forward faster • How to avoid getting distracted by every new AI tool • One simple exercise you can implement immediately Ready to get clear on what you should delegate? Visit: https://clarify.ironbrij.com.au/ If you’re a solopreneur, coach, or small business owner who feels like everything depends on you, this conversation will help you rethink how you spend your time—and what you need to let go of to grow. Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

  4. Aug 13

    How A Third-Generation Photographer Built A Gig-Economy Team

    In this episode of Plan Like a Boss, Tonya Lawson sits down with Lesle Lane, CEO of Studio 13, to talk about what it really takes to scale a creative business without burning out. Lesle is a third-generation photographer who stepped into her family business at a young age and quickly found herself navigating major industry disruption, including the transition from film to digital photography. She shares the story behind investing $200,000 in her first digital camera, modernizing a generational business, and eventually moving from an exhausting solopreneur model to a more flexible team of independent contractors. You’ll hear how Lesle built systems and standard operating procedures, delegated administrative work, and created more space to think strategically about the future of her company. She also explains why 1099 contractors helped her business scale more efficiently, how asking for feedback strengthened her sales process, and why relationships and warm introductions can be more powerful than cold outreach. Lesle also shares lessons from her years as a competitive ice skater, including discipline, resilience, handling rejection, and learning to seek constructive criticism instead of avoiding it. In this episode, you’ll learn: • How to scale a creative business without doing everything yourself • Why systems and delegation can reduce burnout • How independent contractors can create more flexibility • Why feedback is essential for improving your sales process • How mentors and allies outside your industry can help you make better decisions • Why relationships matter more than transactions • How stepping away from technology can create space for better strategic thinking Lesle’s challenge for small business owners is simple: take 30 minutes without technological input. Go for a walk, meditate, practice yoga, or simply give yourself quiet space to think. When you create room for original thought, you create room to lead your business instead of only reacting to it. Connect with Lesle Lane and Studio 13: https://www.studio13online.com/contact/ Subscribe to Plan Like a Boss wherever you listen to podcasts, and share this episode with a fellow entrepreneur who needs more space, better systems, and a smarter way to grow. Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

  5. Aug 6

    Human-First Marketing in the Age of AI with Jocelynn Flowers

    How do you grow your business with digital marketing and AI without losing the human connection behind your brand? In this episode of Plan Like a Boss, Tonya Lawson sits down with Jocelynn Flowers, founder and CEO of J. Flowers Marketing, to talk about human-first marketing, sustainable productivity, and creating content without burning yourself out. Jocelynn shares how she helps coaches, authors, and service-based business owners simplify their marketing, strengthen their messaging, and build systems that support both their business goals and their lifestyle. She explains how entrepreneurs can use AI and automation intentionally while keeping their own voice, personality, and relationships at the center of their brand. You’ll also hear practical strategies for managing your time and social media as a solopreneur, including Jocelynn’s color-coded calendar system, the importance of firm work boundaries, and why you do not need to post every day to build a strong online presence. In this episode, you’ll learn: • How to use AI without losing your authentic voice • Why human-first marketing creates stronger connections • How to choose one social media platform and stay consistent • Which engagement metrics matter most • How to create sustainable boundaries around your work • Why capturing ideas is often more important than creating on demand • How one idea can become multiple pieces of content • Why showing up before you feel ready can move your business forward Jocelynn’s biggest reminder is simple: you may not have a content creation problem—you may have a content capture problem. Write down your ideas when they come, return to them during your content-planning time, and turn each one into multiple ways to serve your audience. Get 30 days of social media prompts: https://jflowersdigital.com/30-day-social-media-prompts-299556 Connect with Jocelynn Flowers: Website: https://jflowersdigital.com Social Media: @JFlowersMarketing Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

  6. Jul 30

    How to Turn Social Media Followers into Paying Customers (Without Chasing Virality)

    Posting consistently but still not seeing meaningful business growth from social media? The problem may not be how often you post. It may be what your content is designed to accomplish. In this episode of Plan Like a Boss, Tonya Lawson sits down with Jamie Coleman, digital marketing strategist and founder of By Jamie Social, to discuss how entrepreneurs and creators can move beyond surface-level metrics and build a social media strategy rooted in clarity, connection, and conversion. Jamie explains why authentic storytelling is outperforming constant selling, how to create content that remains valuable long after it is published, and why viral views do not always translate into loyal followers, leads, or customers. In this episode, you’ll learn:  • Why posting more is not always the answer  • How authentic storytelling builds trust  • The difference between attention and sustainable growth  • The three content categories every entrepreneur needs  • How to create evergreen social media content  • Why your hook, on-screen text, caption, and hashtags should align  • How to use hashtags for content categorization and search  • How to stay top of mind without constantly selling  • How to choose the right platform for your target audience  • What makes LinkedIn content different from TikTok and Instagram Whether you’re a solopreneur, creator, coach, or small-business owner, this conversation will help you create intentional content that supports your long-term business goals—not just your next viral moment. Connect with Jamie Coleman:  https://stan.store/byjamiesocial Chapters 0:00 - Why Social Media Isn’t Converting 2:39 - Authentic Storytelling Drives Growth 5:36 - Best Content Formats Today 9:35 - Authenticity Beats Performance 13:32 - Build Evergreen Content Assets 18:54 - Turn Followers Into Customers 21:57 - Three Essential Content Buckets 24:32 - Best Platform for Your Business 27:01 - LinkedIn Marketing for B2B Subscribe to Plan Like a Boss so you never miss an episode filled with actionable strategies for planning, marketing, and growing your business. Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

  7. Jul 23

    The Secret Sign That Shows You're Operating Beyond Your Business Capacity

    Somewhere along the way, online business turned into business all the time. How to find Gwen: https://peekadvisory.com/ In this episode, Gwen Taniguchi and Tonya Lawson explore how the shift to constant availability—especially during and after COVID—changed the way entrepreneurs work, communicate, and set boundaries. What once promised more freedom can quickly become an always-on cycle of notifications, expectations, and pressure. They unpack how resentment builds quietly when business begins taking over every part of life, why burnout is often a symptom of deeper boundary problems, and what it takes to create a business that supports your life instead of consuming it. In this episode, you’ll hear: • Why online business can become “business all the time” • How post-COVID work culture changed expectations around availability • The subtle ways resentment develops • Why constant access is not the same as sustainable growth • How to begin creating healthier rhythms and boundaries This conversation is for entrepreneurs, creators, and business owners who want to grow without sacrificing their energy, relationships, or well-being. The goal is not simply to build a successful business. It is to build one you can sustainably live with. Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

  8. Jul 16

    From Teacher to FinTech Founder: Sarah Potter Jeanneault’s Entrepreneurial Journey

    What does it really look like to use AI in your business without losing the human connection that makes your brand special? In this episode of Plan Like a Boss, Tonya Lawson sits down with Sarah Potter Jeanneault, a growth strategist, published author, FinTech founder, and entrepreneur with two successful exits. Sarah shares her journey from classroom teacher to business owner, corporate executive, and leader in the emerging human-plus-AI workplace. Together, they explore why the future of work is not human versus AI, but human plus AI. Sarah explains how entrepreneurs can use AI to support productivity, content creation, planning, and operations while still protecting their voice, judgment, customer relationships, and authenticity. The conversation also covers the realities of leaving a secure career, navigating the identity shift into entrepreneurship, documenting business systems, and building a company that can operate without everything depending on the founder. In this episode, you’ll learn:  • How to use AI without losing your authentic voice  • Why human connection remains a major competitive advantage  • Where solopreneurs can use AI most effectively  • How to explore entrepreneurship without making an impulsive leap  • Why documented systems make a business easier to grow, delegate, or sell  • What entrepreneurs can learn from teachers about leadership and communication Learn more about ProcedureFlow:  https://procedureflow.com/ Listen to The Why to The Way Podcast:  https://www.whytotheway.com/ Whether you are considering a career change, building a business, or trying to use AI more responsibly, this conversation will help you take your next step with greater clarity and confidence. Let's Connect: ✨ Apply for Search To Sales: https://tonyalawson.com/search ✍️ Sign up for my newsletter: https://api.leadconnectorhq.com/widget/form/WZgVVwhJm3moIYAP6V5i 📸 Follow me on Insta and TikTok @dr.tonyalawson 🔗 LinkedIn: https://www.linkedin.com/in/tonya-lawson-64779739/

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Plan Like a Boss is your go-to podcast for mastering planning, productivity, and strategy as a solo or small business entrepreneur. Each week, you'll get practical tips and real-life insights to help you set smart goals, manage your time, and grow a business that actually fits your life.

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