Grow A Small Business Podcast

Troy Trewin

Our weekly 30 minute podcast helps you, a small business owner with 5 to 30 team members, take your company to the next level. The Grow A Small Business community, weekly cast, blog and leadership email supports leaders get through the pain of growth. With insights, lessons learned, books and tools as well as habits these experienced small business owners suggest you develop, our interviews unearth tremendous value for anyone wanting to grow their business with less stress.

  1. 1d ago

    Giuseppe Grammatico | The Franchise Guide: From Leaving J.P. Morgan to Building & Selling a Business, Then Helping Entrepreneurs Choose the Right Franchise for Time Freedom & Long-Term Success. (Episode 788 - Giuseppe Grammatico)

    In this episode of the Grow A Small Business Podcast host Troy Trewin interviews Giuseppe Grammatico founder of The Franchise Guide shares how he left J P Morgan to build and successfully sell a building services business before helping aspiring entrepreneurs find the right franchise He reveals why time freedom matters more than money how consistency and leadership fuel sustainable growth and why every business owner should plan their exit from day one while creating a business that can thrive without them. Why would you wait any longer to start living the lifestyle you signed up for? Balance your health, wealth, relationships and business growth. And focus your time and energy and make the most of this year. Let's get into it by clicking here. Troy delves into our guest's startup journey, their perception of success, industry reconsideration, and the pivotal stress point during business expansion. They discuss the joys of small business growth, vital entrepreneurial habits, and strategies for team building, encompassing wins, blunders, and invaluable advice. And a snapshot of the final five Grow A Small Business Questions: What do you think is the hardest thing in growing a small business? Giuseppe Grammatico shares that the hardest part of growing a small business is taking full ownership of every decision and learning to be decisive especially when you have never owned a business before He explains that new entrepreneurs often overthink their choices and second guess themselves but success comes from making confident decisions learning from mistakes and adapting quickly as the business grows. What's your favorite business book that has helped you the most? Giuseppe Grammatico shares that the business book that has helped him the most is Traction by Gino Wickman because it provides a practical framework for building and managing every aspect of a business He also highly recommends The E-Myth Revisited by Michael E. Gerber for teaching entrepreneurs how to create systems that allow a business to grow beyond the owner. Are there any great podcasts or online learning resources you'd recommend to help grow a small business? Giuseppe Grammatico shares that podcasts have become his primary source of learning and he recommends The How of Business by Henry Lopez for practical business ownership advice Profit Comes First by Rocky Lalvani for mastering business finances and cash flow and podcasts by Dan Buettner and Mike Chang for improving health and performance because a healthy entrepreneur builds a stronger business. What tool or resource would you recommend to grow a small business? Giuseppe Grammatico shares that a powerful CRM like Go High Level is one of the best tools for growing a small business because it automates emails text messages AI phone calls social media and customer follow ups in one place He also recommends Sequence as a valuable financial tool for implementing the Profit First system and automating cash flow management. What advice would you give yourself on day one of starting out in business? Giuseppe Grammatico shares that if he could go back to day one he would remind himself that entrepreneurship is not a straight path and that challenges are part of the journey He advises new business owners to stay focused on their purpose adapt to change develop thick skin and build a business that creates freedom while enjoying the process instead of waiting for the destination.  Book a 20-minute Growth Chat with Troy Trewin to see if you qualify for our upcoming course. Don't miss out on this opportunity to take your small business to new heights! Enjoyed the podcast? Please leave a review on iTunes or your preferred platform. Your feedback helps more small business owners discover our podcast and embark on their business growth journey.     Quotable quotes from our special Grow A Small Business podcast guest: The best business decisions come from taking action not waiting for certainty - Giuseppe Grammatico Build a business that creates freedom because success means nothing without time to enjoy it - Giuseppe Grammatico Every challenge in business is an opportunity to learn adapt and grow stronger - Giuseppe Grammatico

    Giuseppe Grammatico | The Franchise Guide: From Leaving J.P. Morgan to Building & Selling a Business, Then Helping Entrepreneurs Choose the Right Franchise for Time Freedom & Long-Term Success. (Episode 788 - Giuseppe Grammatico)
  2. Jul 26

    Cheryl Contee (Attentively): From Vision Strategy to a Multi-Million Dollar SaaS Exit | Building a 12-Person Team, Becoming the First Black Female Founder Acquired by a Nasdaq-Listed Company & Advancing Ethical AI. (Episode 787 - Cheryl Contee)

    In this episode of the Grow A Small Business Podcast host Troy Trewin interviews Cheryl Contee, founder of BrightWorks AI, shares how she built a purpose-driven SaaS company serving nonprofits, scaled it to a 12-person team with multi-million-dollar revenue, and achieved a historic exit as the first Black female founder to sell a tech startup to a Nasdaq-listed company. Cheryl discusses the realities of fundraising, hiring, leadership, and planning for a successful exit while emphasizing the power of relationships and reputation. She also explains why she is now helping nonprofits adopt AI ethically through her latest venture. This conversation is packed with practical lessons on resilience, innovation, and building a business that creates lasting impact. Also check Cheryl Contee's book, AI for Nonprofits: Putting Artificial Intelligence to Work for Your Cause, and her appearance on the Built to Sell Radio podcast, where she shares how she built and successfully sold Attentive.ly, an AI-powered social listening platform acquired by Blackbaud. Why would you wait any longer to start living the lifestyle you signed up for? Balance your health, wealth, relationships and business growth. And focus your time and energy and make the most of this year. Let's get into it by clicking here. Troy delves into our guest's startup journey, their perception of success, industry reconsideration, and the pivotal stress point during business expansion. They discuss the joys of small business growth, vital entrepreneurial habits, and strategies for team building, encompassing wins, blunders, and invaluable advice. And a snapshot of the final five Grow A Small Business Questions:  What do you think is the hardest thing in growing a small business? Cheryl Contee shares that the hardest part of growing a small business is having the confidence to believe in yourself, especially when no one else believes in your vision. Cheryl Contee shares that entrepreneurs must be willing to put in 110% effort and embrace hard work every day. Cheryl Contee shares that self-belief is what keeps founders moving forward through uncertainty and setbacks. Cheryl Contee shares that lasting success comes from combining confidence with consistent dedication and perseverance. What's your favorite business book that has helped you the most? Cheryl Contee shares that her favorite business book is Who Moved My Cheese? because its lessons about adapting to change are even more relevant in today's fast-changing business world. Cheryl Contee shares that entrepreneurs must be willing to follow new opportunities instead of clinging to old ways of working. Cheryl Contee shares that embracing change with the right mindset helps business owners stay resilient and competitive. Cheryl Contee shares that continuous adaptation is essential for long-term business success. Are there any great podcasts or online learning resources you'd recommend to help grow a small business? Cheryl Contee shares that she highly recommends Apple News+ for access to trusted publications like The Wall Street Journal, Bloomberg, The Atlantic, and The Guardian, offering broad and in-depth business insights. Cheryl Contee shares that YouTube has also become one of her favorite learning platforms, especially for independent experts and international news sources. Cheryl Contee shares that exploring multiple perspectives helps business owners make better-informed decisions. Cheryl Contee shares that continuous learning from diverse, credible sources is essential for staying ahead in a rapidly changing world. What tool or resource would you recommend to grow a small business? Cheryl Contee shares that one of the best tools for growing a small business is a well-crafted pitch deck rather than a lengthy business plan. Cheryl Contee shares that a 10–15 slide pitch deck helps entrepreneurs clearly define their market, customers, competitors, business model, and growth strategy. Cheryl Contee shares that answering these core questions creates clarity and prepares business owners for investors, partners, and opportunities. Cheryl Contee shares that a strong pitch deck is a practical resource for building and scaling a successful business. What advice would you give yourself on day one of starting out in business? Cheryl Contee shares that if she could go back to day one, she would remind herself, "You've got this," and trust her ability to succeed. Cheryl Contee shares that embracing what makes you different allows you to see opportunities others may overlook. Cheryl Contee shares that being authentic and courageous opens the door to creating things that have never been done before. Cheryl Contee shares that believing in yourself from the very beginning is one of the greatest advantages an entrepreneur can have.  Book a 20-minute Growth Chat with Troy Trewin to see if you qualify for our upcoming course. Don't miss out on this opportunity to take your small business to new heights! Enjoyed the podcast? Please leave a review on iTunes or your preferred platform. Your feedback helps more small business owners discover our podcast and embark on their business growth journey.     Quotable quotes from our special Grow A Small Business podcast guest: It's okay to be different because different people see opportunities others miss - Cheryl Contee Your reputation is the most powerful marketing tool your business will ever have - Cheryl Contee Plan your exit from day one because successful businesses are built with the end in mind - Cheryl Contee

    Cheryl Contee (Attentively): From Vision Strategy to a Multi-Million Dollar SaaS Exit | Building a 12-Person Team, Becoming the First Black Female Founder Acquired by a Nasdaq-Listed Company & Advancing Ethical AI. (Episode 787 - Cheryl Contee)
  3. Jul 19

    Adiel Gorel (International Capital Group): From Hewlett-Packard Engineer to 10,000+ Homes | Building a 42-Year Real Estate Empire, Winning in Recessions & Creating Long-Term Wealth Through Smart Property Investing. (Episode 786 - Adiel Gorel)

    In this episode of the Grow A Small Business Podcast host Troy Trewin interviews Adiel Gorel, Founder of International Capital Group, shares how he went from being a Hewlett-Packard engineer to building a 42-year real estate investment business that has helped investors purchase more than 10,000 homes. He explains why long-term thinking, fixed-rate mortgages, and staying calm during market downturns create lasting wealth. Adiel also discusses scaling a business, leading through economic cycles, building the right mindset, and avoiding panic when recessions hit. His journey offers practical lessons on entrepreneurship, resilience, and financial freedom through disciplined investing. Check out Adiel Gorel's book, Remote Control Retirement Riches: How to Change Your Future with Rental Homes. In this practical guide, he shares the proven strategies that have helped investors build long-term wealth through rental properties. Whether you're a first-time investor or looking to grow your portfolio, the book offers actionable insights on creating financial freedom through smart real estate investing. Why would you wait any longer to start living the lifestyle you signed up for? Balance your health, wealth, relationships and business growth. And focus your time and energy and make the most of this year. Let's get into it by clicking here.   Troy delves into our guest's startup journey, their perception of success, industry reconsideration, and the pivotal stress point during business expansion. They discuss the joys of small business growth, vital entrepreneurial habits, and strategies for team building, encompassing wins, blunders, and invaluable advice.   And a snapshot of the final five Grow A Small Business Questions:  What do you think is the hardest thing in growing a small business? Adiel Gorel shares that the hardest part of growing a small business is living with uncertainty and accepting that the responsibility ultimately rests on the owner. Unlike a traditional job, there is no guaranteed paycheck, and every decision affects both the business and the employees who rely on it. He emphasizes that entrepreneurs must stay resilient, take ownership, and remain prepared for both opportunities and setbacks. What's your favorite business book that has helped you the most? Adiel Gorel shares that one of the business books he highly recommends is his own, Remote Control Retirement Riches, which reflects decades of real estate investing experience. He also praises Rich Dad Poor Dad by Robert Kiyosaki for its powerful lessons on wealth creation and financial mindset, noting that its principles have inspired countless aspiring investors and entrepreneurs. Are there any great podcasts or online learning resources you'd recommend to help grow a small business? Adiel Gorel shares that while he doesn't regularly follow business podcasts, he spends much of his learning time exploring health and wellness content. He believes maintaining good health gives entrepreneurs the energy, focus, and mental clarity needed to build and grow a successful business over the long term. What tool or resource would you recommend to grow a small business? Adiel Gorel shares that every business needs a balance between simplicity and effective systems. He recommends using reliable accounting software like QuickBooks to stay organized, manage finances efficiently, and gain a clear understanding of the business's financial health as it grows. What advice would you give yourself on day one of starting out in business? Adiel Gorel shares that he would remind his younger self that business moves in cycles, with both booms and downturns. He advises entrepreneurs not to become overconfident during good times or panic during recessions, emphasizing that patience, preparation, and staying the course are often the keys to long-term success.  Book a 20-minute Growth Chat with Troy Trewin to see if you qualify for our upcoming course. Don't miss out on this opportunity to take your small business to new heights! Enjoyed the podcast? Please leave a review on iTunes or your preferred platform. Your feedback helps more small business owners discover our podcast and embark on their business growth journey.   Quotable quotes from our special Grow A Small Business podcast guest: You are not a cog in the machine you are the machine - Adiel Gorel Success comes from staying focused while time and patience do the heavy lifting - Adiel Gorel The biggest mistakes in business happen when fear replaces long term thinking - Adiel Gorel

    Adiel Gorel (International Capital Group): From Hewlett-Packard Engineer to 10,000+ Homes | Building a 42-Year Real Estate Empire, Winning in Recessions & Creating Long-Term Wealth Through Smart Property Investing. (Episode 786 - Adiel Gorel)
  4. Jul 12

    Ashley Stahl (Wise Whisper Agency): From CIA & Counterterrorism to a $5M Speaking Business | 10M-View TED Talk, Building a 25-Person Team, and the Good, Grit & Gift Leadership Formula. (Episode 785 - Ashley Stahl)

    In this episode of the Grow A Small Business Podcast host Troy Trewin interviews, Ashley Stahl, founder of Wise Whisper Agency, shares her journey from working in national security and counterterrorism to building a thriving speaking and coaching business. She reveals how her TEDx talks, including one with over 10 million views and ranked among the Top 100 TED Talks, transformed her career and inspired her to help others craft powerful talks. Ashley discusses scaling Wise Whisper Agency from a small team to around 25 people and growing revenue from $700K in its first year to an expected $4–5M, while emphasizing the challenges of building a sales team, hiring with integrity, and creating a soulful company culture. The conversation is packed with insights on leadership, personal growth, resilience, and the importance of helping people share ideas that can genuinely change lives. Why would you wait any longer to start living the lifestyle you signed up for? Balance your health, wealth, relationships and business growth. And focus your time and energy and make the most of this year. Let's get into it by clicking here. Troy delves into our guest's startup journey, their perception of success, industry reconsideration, and the pivotal stress point during business expansion. They discuss the joys of small business growth, vital entrepreneurial habits, and strategies for team building, encompassing wins, blunders, and invaluable advice. And a snapshot of the final five Grow A Small Business Questions: What do you think is the hardest thing in growing a small business? Ashley Stahl shares that the hardest thing about growing a small business is managing your energy. She explains that there are days when you work incredibly hard and wonder how you'll do it all again tomorrow, but what keeps her going is her deep belief in Wise Whisper Agency, the impact it has on helping people craft powerful talks, and the mission of getting their ideas onto major stages, including TEDx. What's your favorite business book that has helped you the most? Ashley Stahl shares that it's been a while since she read a traditional business book, but if she had to name one influence, she would point to Alex Hormozi's work. She says she loves his approach because it's "all protein and no fat," meaning he gets straight to the tactical, practical advice without unnecessary fluff, and she finds that direct, actionable style especially valuable for building and growing a business. Are there any great podcasts or online learning resources you'd recommend to help grow a small business? Ashley Stahl shares that one of her favorite podcasts for professional development is Diary of a CEO. She says host Steven Bartlett does an excellent job interviewing remarkable people and exploring topics with a level of depth that many other shows don't, making it a valuable resource for entrepreneurs and anyone looking to grow a small business. What tool or resource would you recommend to grow a small business? Ashley Stahl shares that the one tool she would most strongly recommend for growing a small business is paid advertising. She believes that many entrepreneurs are held back by fear of running ads, but once you learn how to use them effectively, paid ads can become a powerful and scalable way to consistently attract leads, grow revenue, and expand your business. What advice would you give yourself on day one of starting out in business? Ashley Stahl shares that if she could go back to day one of starting out in business, she would tell herself that the journey will become much bigger than she ever imagined. She says that building a business is about far more than making money or helping people; it's ultimately a path of personal growth that teaches you how capable, resilient, and powerful you truly are.  Book a 20-minute Growth Chat with Troy Trewin to see if you qualify for our upcoming course. Don't miss out on this opportunity to take your small business to new heights! Enjoyed the podcast? Please leave a review on iTunes or your preferred platform. Your feedback helps more small business owners discover our podcast and embark on their business growth journey.     Quotable quotes from our special Grow A Small Business podcast guest: When you have a team working for you, they don't work for you; you work for them — Ashley Stahl Learn the rules so that you can break them like an artist — Ashley Stahl This is about so much more than building a business or making money; it's about learning how capable you are — Ashley Stahl

    Ashley Stahl (Wise Whisper Agency): From CIA & Counterterrorism to a $5M Speaking Business | 10M-View TED Talk, Building a 25-Person Team, and the Good, Grit & Gift Leadership Formula. (Episode 785 - Ashley Stahl)
  5. Jul 5

    Conrad Ruiz, Founder of Well Aware: From $2,500 Revenue and 3 Years of Struggle to Scaling a 50+ VA Team, Building a Fast-Growing Fractional COO Business, Reaching $600K+ Revenue, and Pursuing the $1M Milestone. (Episode 784 - Conrad Ruiz)

    In this episode of the Grow A Small Business Podcast, host Troy Trewin interviews Conrad Ruiz, founder of Well Aware, shares his journey from earning just $2,500 in his first year and struggling through three challenging years to building a thriving virtual assistant and fractional COO business. He discusses the importance of time management, customer delight, and persistence in overcoming uncertainty and growing a company. Conrad reveals how Well Aware expanded to a network of more than 50 virtual assistants while staying focused on helping business owners reclaim their time. The conversation also explores leadership, team building, accountability, and his ambitious goal of scaling the business beyond $1 million in annual revenue.  Why would you wait any longer to start living the lifestyle you signed up for? Balance your health, wealth, relationships and business growth. And focus your time and energy and make the most of this year. Let's get into it by clicking here. Troy delves into our guest's startup journey, their perception of success, industry reconsideration, and the pivotal stress point during business expansion. They discuss the joys of small business growth, vital entrepreneurial habits, and strategies for team building, encompassing wins, blunders, and invaluable advice. And a snapshot of the final five Grow A Small Business Questions: What do you think is the hardest thing in growing a small business? Conrad Ruiz shares that the hardest part of growing a small business is persisting through uncertainty when results are not guaranteed. He reflects on the challenging early years, where survival, self-doubt, and ambiguity were constant realities. Conrad emphasizes that entrepreneurs must learn to navigate discomfort daily and keep moving forward until they transition from simply surviving to building a business that can truly thrive. What's your favorite business book that has helped you the most? Conrad Ruiz shares that the business book that has helped him the most is Four Thousand Weeks: Time Management for Mortals. Although it is not a traditional business book, he believes it should be treated as one because it offers powerful lessons on time, priorities, and making the most of a limited life. The book helped shape his perspective on managing time effectively while building and growing a business. Are there any great podcasts or online learning resources you'd recommend to help grow a small business? Conrad Ruiz shares that he is not a heavy podcast listener, but recommends learning from high-quality newsletters, blogs, workshops, and industry experts. He highlights the content from Lavender AI as a great example, noting that its blog provides practical lessons on cold email outreach and copywriting. Conrad also encourages business owners to stay curious, network with knowledgeable people, and continuously learn from real-world experiences, mentors, and hands-on problem-solving. What tool or resource would you recommend to grow a small business? Conrad Ruiz recommends having an extra pair of hands to help you grow, specifically a virtual assistant. He explains that business owners often spend too much time on tasks that can be delegated, limiting their ability to focus on growth. By bringing in the right support, entrepreneurs can free up valuable time, increase productivity, and concentrate on higher-value activities that drive the business forward. What advice would you give yourself on day one of starting out in business? Conrad Ruiz shares that if he could speak to himself on day one, he would say, "You're an idiot, but it's okay—there's so much you're going to figure out." He reflects on how much learning comes through experience and mistakes. Drawing on advice from his 99-year-old father, Conrad emphasizes one simple lesson above all: take your time, trust the process, and allow yourself the space to grow as an entrepreneur.  Book a 20-minute Growth Chat with Troy Trewin to see if you qualify for our upcoming course. Don't miss out on this opportunity to take your small business to new heights! Enjoyed the podcast? Please leave a review on iTunes or your preferred platform. Your feedback helps more small business owners discover our podcast and embark on their business growth '/?journey.     Quotable quotes from our special Grow A Small Business podcast guest: Don't obsess over anything other than creating value for the well-being of others — Conrad Ruiz The hardest part of entrepreneurship is persisting through uncertainty when you don't know if it will work — Conrad Ruiz Take your time—growth comes from experience, mistakes, and the lessons you learn along the way — Conrad Ruiz

  6. Jun 28

    Founder of Big Heart Breeders | From a Family Pet to a $700K+ Business, Scaling to a Team of 10, Building a Leading Mini Golden Retriever Breeding Company, Mastering Google & SEO Marketing, and Leveraging AI for Growth. (Episode 783 - Heather Gibson)

    In this episode of the Grow A Small Business Podcast host Troy Trewin interviews Heather Gibson, founder of Big Heart Breeders, shares how a family's love for pets evolved into a thriving business generating over $700,000 annually with a team of 10. She discusses her journey from solopreneur to business owner, the challenges of hiring and delegation, and the importance of building the right team. Heather also reveals how Google marketing, SEO, and AI tools have fueled her growth. The conversation explores lessons in leadership, work-life balance, and creating a meaningful impact through pet breeding, nutrition, and education. Why would you wait any longer to start living the lifestyle you signed up for? Balance your health, wealth, relationships and business growth. And focus your time and energy and make the most of this year. Let's get into it by clicking here. Troy delves into our guest's startup journey, their perception of success, industry reconsideration, and the pivotal stress point during business expansion. They discuss the joys of small business growth, vital entrepreneurial habits, and strategies for team building, encompassing wins, blunders, and invaluable advice. And a snapshot of the final five Grow A Small Business Questions: What do you think is the hardest thing in growing a small business? Heather Gibson shares that the hardest part of growing a small business is staying consistent and having the grit to keep going when results are not immediate. She explains that while some businesses appear to achieve overnight success, most growth comes from years of steady effort and learning. Heather believes that persistence, the right mindset, and showing up every day are what ultimately create opportunities for breakthrough growth. What's your favorite business book that has helped you the most? Heather Gibson shares that the business book that has helped her the most is Who Not How by Dan Sullivan and Benjamin Hardy. She explains that the book transformed her mindset around hiring and delegation, teaching her that business success comes from finding the right people to help achieve goals rather than trying to do everything yourself. Are there any great podcasts or online learning resources you'd recommend to help grow a small business? Heather Gibson shares that she enjoys learning from a variety of podcasts and online resources that focus on business growth, mindset, and practical implementation. She specifically mentions the Grow A Small Business podcast as a valuable resource and emphasizes the importance of continuously learning from experienced entrepreneurs, coaches, and industry experts to stay ahead in a rapidly changing business environment. What tool or resource would you recommend to grow a small business? Heather Gibson recommends AI as one of the most powerful tools available to small business owners today. She highlights tools like Claude for copywriting, Gemini for image creation, and ChatGPT for a wide range of business tasks. Heather believes AI can dramatically improve productivity, provide valuable business insights, and help small businesses compete more effectively while saving both time and money. What advice would you give yourself on day one of starting out in business? Heather Gibson shares that if she could give advice to herself on day one, she would say, "Buckle in and get ready for a wild ride." She never imagined her business would grow to its current size and emphasizes that entrepreneurship comes with both difficult and rewarding seasons. Her advice is to stay resilient during the tough times, enjoy the successful moments, and always plan ahead for future challenges.  Book a 20-minute Growth Chat with Troy Trewin to see if you qualify for our upcoming course. Don't miss out on this opportunity to take your small business to new heights! Enjoyed the podcast? Please leave a review on iTunes or your preferred platform. Your feedback helps more small business owners discover our podcast and embark on their business growth journey.     Quotable quotes from our special Grow A Small Business podcast guest: My hires don't have to do things exactly the way I do—if they can do it 80% as well, that's a great hire — Heather Gibson Success isn't about the numbers; it's about the value you create and the lives you impact — Heather Gibson The biggest breakthroughs in business come from consistent effort, continuous learning, and the courage to keep going — Heather Gibson

    Founder of Big Heart Breeders | From a Family Pet to a $700K+ Business, Scaling to a Team of 10, Building a Leading Mini Golden Retriever Breeding Company, Mastering Google & SEO Marketing, and Leveraging AI for Growth. (Episode 783 - Heather Gibson)
  7. Jun 21

    Ryan Estes, Founder of KitCaster | From Losing 95% of Clients During COVID to $2M Annual Revenue in 18 Months, Building a Leading Podcast Booking Agency, Scaling to 25 Employees, Exiting Successfully, and Thriving in the AI Era. (Episode 782 - Ryan Este

    In this episode of the Grow A Small Business Podcast host Troy Trewin interviews Ryan Estes, co-founder of KitCaster, shares his remarkable journey from losing 95% of his digital agency clients during COVID to building a thriving podcast booking agency that reached a $2 million annual run rate within just 18 months. Ryan discusses how KitCaster scaled from 3 to 25 team members, the lessons learned from rapid growth, and the strategies that helped the company stand out in the podcasting industry. He also opens up about successfully exiting the business, navigating the impact of AI, and building a company designed for acquisition. This conversation is packed with valuable insights on entrepreneurship, leadership, resilience, and creating long-term business success.    Why would you wait any longer to start living the lifestyle you signed up for? Balance your health, wealth, relationships and business growth. And focus your time and energy and make the most of this year. Let's get into it by clicking here.   Troy delves into our guest's startup journey, their perception of success, industry reconsideration, and the pivotal stress point during business expansion. They discuss the joys of small business growth, vital entrepreneurial habits, and strategies for team building, encompassing wins, blunders, and invaluable advice.   And a snapshot of the final five Grow A Small Business Questions: What do you think is the hardest thing in growing a small business? Ryan Estes, a former musician and serial entrepreneur, co-founded Kit Caster in 2019 — a podcast booking agency that places startup founders and executives on top podcasts worldwide. When COVID wiped out 95% of his digital marketing agency's clients, Ryan doubled down on Kit Caster, riding the pandemic-era podcasting boom to hit a $2 million annual run rate within just 18 months of launch. The company grew from 3 to 25 employees at its peak, but has since scaled back to around 8–9 as AI-driven efficiencies reduced staffing needs. Ryan credits strategic early-stage lending and a repeatable sales process as key drivers of their rapid growth. Beyond revenue, Ryan defines success by having built a business that allowed him and his wife to be fully present for their children — and remains a strong believer that podcasting, as a medium for human connection and storytelling, will continue to thrive. What's your favorite business book that has helped you the most? Ryan Estes gave a quick and clear answer — "Traction" by Gino Wickman. This book, which focuses on the Entrepreneurial Operating System (EOS), clearly resonated with Ryan as a founder who valued building structured, scalable operations. Given Kit Caster's rapid growth and their goal of building a business to sell, the frameworks in Traction around team alignment, processes, and goal-setting would have been especially relevant. It's a fitting choice for an entrepreneur who emphasized repeatable systems as a key driver of his success. Are there any great podcasts or online learning resources you'd recommend to help grow a small business? Ryan Estes shares that his top recommendation is his own podcast — "AI for Founders" (aiforfounder.co) — where he interviews founders who are building AI companies or building with AI. With around 47,000 subscribers and growing quickly, the show covers not just business metrics and KPIs, but also the emotional side of navigating the AI era as a founder. Beyond his own podcast, he also recommends the "All In" podcast to stay updated on what top investors and billionaires are thinking. He additionally highlights the content from Alex and Leila Hormozi — early Kit Caster clients — praising their mastery of podcasting and the phenomenal growth they've achieved. What tool or resource would you recommend to grow a small business? Ryan Estes shares that his top tool recommendation to grow a small business is Quad Code. He is enthusiastic about its potential, particularly in the context of AI, and advises small business owners not to feel overwhelmed or behind when it comes to adopting AI tools. He humorously uses a baseball analogy, suggesting that the early adopters will do the hard work of figuring it out, and that within the next six months or so, it will become much more accessible for everyone to simply step in and benefit from it. What advice would you give yourself on day one of starting out in business? Ryan Estes shares that the advice he would give himself on day one of starting out in business is simple yet powerful — "You can do it." He repeats this twice with conviction, reflecting a deep belief in self-confidence and self-trust as the foundation of any entrepreneurial journey. This straightforward but heartfelt message speaks to the self-doubt that many founders face at the beginning, and suggests that believing in yourself is the most important mindset a new business owner can carry with them from day one. Book a 20-minute Growth Chat with Troy Trewin to see if you qualify for our upcoming course. Don't miss out on this opportunity to take your small business to new heights! Enjoyed the podcast? Please leave a review on iTunes or your preferred platform. Your feedback helps more small business owners discover our podcast and embark on their business growth journey.     Quotable quotes from our special Grow A Small Business podcast guest: Cash is king, but being present for your family is the greatest award you'll never receive — Ryan Estes If you're really interested in scaling and going for the gold, don't fail to act — indecision can be the most costly choice — Ryan Estes Podcasting is the exemplar of human connection — it's people talking to each other the way we have around a campfire forever — Ryan Estes

    Ryan Estes, Founder of KitCaster | From Losing 95% of Clients During COVID to $2M Annual Revenue in 18 Months, Building a Leading Podcast Booking Agency, Scaling to 25 Employees, Exiting Successfully, and Thriving in the AI Era. (Episode 782 - Ryan Este
  8. Jun 14

    How Michèle Hecken Grew Alpha Translations into a Global Leader Serving Top Law Firms, Built Systems That Ran Without Her, Anticipated the AI Revolution Early, and Achieved a $6M All-Cash Exit at 6.7x EBITDA . (Episode 781 - Michèle Hecken)

    In this episode of the Grow A Small Business Podcast host Troy Trewin interviews Michèle Hecken shares how she built Alpha Translations into a global business serving top law firms while raising two young children after moving from Germany to Canada. She explains how creating systems and empowering her team allowed her to work just 4–10 hours a week for 15 years. Michèle reveals how her company was building early large language models long before today's AI boom and why she chose to sell instead of reinventing the business. She discusses the challenges of surviving the 2008 financial crisis, rebuilding stronger, and creating a company that could run without her involvement. Listeners will learn valuable lessons on leadership, delegation, mindset, business exits, and designing a business that supports the life they truly want. The Art of Offboarding: How to Transform Your Business to Run Without You by Michèle Hecken is a practical guide for entrepreneurs aiming to move away from day-to-day operations and create a business that runs independently. It focuses on the power of intentional delegation and structured exit from daily tasks to unlock greater freedom, focus, and sustainable growth. Why would you wait any longer to start living the lifestyle you signed up for? Balance your health, wealth, relationships and business growth. And focus your time and energy and make the most of this year. Let's get into it by clicking here. Troy delves into our guest's startup journey, their perception of success, industry reconsideration, and the pivotal stress point during business expansion. They discuss the joys of small business growth, vital entrepreneurial habits, and strategies for team building, encompassing wins, blunders, and invaluable advice. And a snapshot of the final five Grow A Small Business Questions: What do you think is the hardest thing in growing a small business? According to Michèle Hecken, the hardest thing in growing a small business is cash flow. She explains that even when a business appears successful, owners constantly face decisions about where to invest money, whether new initiatives will generate returns, and how to maintain enough cash reserves to navigate uncertainty. Michèle believes that managing consistent cash flow is critical because it gives business owners the flexibility to experiment, survive challenges, and continue growing without putting the company at risk. What's your favorite business book that has helped you the most? Michèle Hecken's favorite business book is Fierce Conversations by Susan Scott. She says the book had a significant impact on how she led her business, particularly in the areas of communication, feedback, and team culture. Michèle values its practical approach to having honest conversations, addressing issues early, and giving constructive feedback effectively. The book influenced her so much that she referenced some of its concepts and tools in her own book about helping entrepreneurs build businesses that can run without them. Are there any great podcasts or online learning resources you'd recommend to help grow a small business? Michèle Hecken recommends learning from a variety of sources rather than relying on a single resource. One podcast she particularly enjoys is the The Mel Robbins Podcast, praising Mel Robbins for her practical insights on mindset and personal growth. She also highly recommends John Warrillow and his podcast Built to Sell Radio, which features valuable lessons from business owners who have successfully scaled and exited their companies. Beyond podcasts, Michèle emphasizes continuous learning through books, coaching, entrepreneurial communities, and implementing what you learn, noting that the real value comes not from consuming information but from applying it to your business. What tool or resource would you recommend to grow a small business? Michèle Hecken shares that the number one tool to grow a small business is your mindset. She believes that without the right mindset, even the best tools and strategies will fail you. She also highly recommends Fierce Conversations by Susan Scott for building honest communication and a strong team culture. Above all, she encourages every entrepreneur to trust themselves and filter every resource through the lens of what truly works for their own business. What advice would you give yourself on day one of starting out in business? Michèle Hecken shares that the advice she would give herself on day one of starting out in business is to trust yourself because you already know what the right thing is to do. She reflects that even though everyone told her she was crazy for doing things differently, her instincts always led her in the right direction. She also emphasizes giving yourself permission to be courageous and not spending too much money on consultants who may not always know your business better than you do. Book a 20-minute Growth Chat with Troy Trewin to see if you qualify for our upcoming course. Don't miss out on this opportunity to take your small business to new heights! Enjoyed the podcast? Please leave a review on iTunes or your preferred platform. Your feedback helps more small business owners discover our podcast and embark on their business growth journey.     Quotable quotes from our special Grow A Small Business podcast guest: Success means having the freedom to choose how I want to live my life, who I want in it, and having the financial means to go after my dreams — Michèle Hecken Don't wait till you exit — exit yourself from your business so it can run without you and you can enjoy your life — Michèle Hecken If you're doing all the work, it's not a business, it's a job that pays you well — Michèle Hecken

    How Michèle Hecken Grew Alpha Translations into a Global Leader Serving Top Law Firms, Built Systems That Ran Without Her, Anticipated the AI Revolution Early, and Achieved a $6M All-Cash Exit at 6.7x EBITDA . (Episode 781 - Michèle Hecken)
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Our weekly 30 minute podcast helps you, a small business owner with 5 to 30 team members, take your company to the next level. The Grow A Small Business community, weekly cast, blog and leadership email supports leaders get through the pain of growth. With insights, lessons learned, books and tools as well as habits these experienced small business owners suggest you develop, our interviews unearth tremendous value for anyone wanting to grow their business with less stress.

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