Start. Scale. Exit. Repeat.: Serial Entrepreneur: Secrets Revealed!

Startup.Club
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In each episode, we explore the things that make serial entrepreneurs tick. With a variety of guests and a "live" audience you'll learn the hacks, tips, and techniques that entrepreneurs use to start, scale, and exit their businesses, and then repeat the process. Recorded LIVE on Clubhouse's Largest Club Startup.club.

  1. 4d ago

    EP239: How to Use AI as a Personal Assistant for Your Business

    Put Your AI Assistant to Work   The inbox keeps filling up, the follow-ups keep coming, and running a business leaves little time to catch every detail. How much of that work can an AI personal assistant handle? This discussion brings together insights from two Startup Club conversations featuring Colin C. Campbell, Michael Gilmour, Michele Van Tilborg, and entrepreneurs from the community. They share examples of daily briefings, email tracking, document preparation, and subscription reviews, along with different views on how much freedom an AI assistant should have. Learn why useful context matters, how founders are refining their workflows, and where human review still plays an essential role. Find more entrepreneurial insights at https://startup.club.

  2. 5d ago

    EP238: AI Hacks for Entrepreneurs: Get Time Back and Stay Focused

    A forgotten invoice. A commitment buried in a chat. A week full of priorities that never made it onto the calendar. In this episode of The Complete Entrepreneur, hosts Michael Gilmour and Colin C. Campbell, and members of the Startup Club community share practical ways they use AI to manage business responsibilities and everyday life. Michael explains his morning briefing and weekly planning routine. Ryan describes a custom local AI system that flags unbilled hours and sends reminders about unfinished work. Joe shares how his team turns discovery calls into organized client reports, and Colin discusses using dedicated AI projects and conversational voice tools. The conversation also explores how much information to connect, where human review matters, and why small, useful applications can be a good place to begin. In this episode: • Organizing daily priorities and weekly plans • Tracking commitments and outstanding work • Keeping client context accessible to a team • Using AI for everyday questions and product comparisons • Balancing convenience with control over business information Find more episodes and founder resources at https://startup.club/.

  3. Oct 28

    EP 237: AI for Startups: Can Small Businesses Beat Big Tech?

    Who benefits most from AI: startups or big corporations? Colin C. Campbell and Michele Van Tilborg open that question to the Startup Club community in a candid discussion about money, data, expertise, and execution. Colin makes the case for entrepreneurs' ability to move quickly and accomplish more with smaller teams, while Michele and community members examine the advantages established companies retain. The conversation covers practical opportunities in AI implementation, improving existing businesses, and helping small companies solve operational problems. It also explores the importance of human oversight, the risk of relying on tools without sufficient understanding, and building competitive advantages through customer relationships, brand, and distribution. Listen for different perspectives on where AI creates opportunities—and how founders can put those opportunities to work. Find more episodes and resources at https://startup.club/

  4. Oct 28

    EP 236: How to Choose a Scalable Business Idea in an AI World

    Before you commit to a business idea, consider what it will take to grow it. Will serving more customers require another location, additional employees, more inventory—or a better way to reach the market? In this episode of Start. Scale. Exit. Repeat., Colin C. Campbell and Michele Van Tilborg explore how to choose a scalable business idea and identify the constraints that could hold it back. Drawing on their experience across e-commerce, domain names, education, and office space, they discuss the trade-offs between growth potential, capital requirements, and competition. They also tackle customer acquisition, building awareness on a limited budget, and using AI alongside experienced professionals to improve execution. A community member's question about finding customers for a new translation app brings those challenges into focus. Listen for practical guidance on evaluating your idea, preparing your operations for growth, and building a business that fits your goals. Find more episodes and resources at https://startup.club/

  5. Sep 25

    EP235: Build What You Love In An AI World

    When You Build Around Something You Actually Care About, AI Can Help You Turn That Passion Into A Real Business Faster Than Ever In this episode of Start, Scale, Exit, Repeat, Colin C. Campbell, Michele Van Tilborg, and members of the Startup Club community explore how entrepreneurs can turn hobbies, interests, expertise, and personal passions into businesses in the AI era. From pet products and residential cruising to domain names, content creation, professional services, software, and customer support, the conversation looks at how AI is removing many of the traditional barriers that once made starting a business expensive or technically difficult. Instead of replacing the entrepreneur, AI can act as a thought partner that helps research, write, design, analyze, automate, and accelerate execution. More importantly, the group discusses why the real advantage still comes from the human behind the technology. When everyone has access to similar AI tools, differentiation comes from understanding real problems, bringing authentic expertise, creating something customers value, and staying involved enough to recognize when the technology gets it wrong. Why building around something you genuinely enjoy can help you stay committed through difficult periods How AI is lowering the cost and complexity of turning an idea into a business Why access to AI alone is no longer a competitive advantage How subject-matter expertise becomes more valuable when paired with AI Why founders should treat AI as a thought partner rather than an automatic decision-maker How AI can remove language, writing, technical, and operational barriers Why authentic human insight still matters in content, products, and customer relationships How entrepreneurs can use AI to amplify real experiences instead of replacing them Why human oversight remains essential when using AI for important business work How AI can help creators move from passive interests to products, services, and companies

  6. Sep 25

    EP234: Learn How To Learn: The Essential Skill For The AI Age

    In A World Where Technology Changes Constantly, The Entrepreneurs Who Keep Learning Will Have The Advantage In this episode of The Complete Entrepreneur, Colin C. Campbell and Michael Gilmour explore why developing a learning mindset has become increasingly important for founders, leaders, and employees navigating the rapid growth of AI. From books and podcasts to hands-on experimentation with AI, they discuss the different ways entrepreneurs can continuously expand their skills, challenge their assumptions, and adapt as their businesses grow. Michael shares why he deliberately dedicates time every day to learning, while Colin examines how AI is making it possible to acquire new capabilities without spending years mastering the traditional mechanics behind them. More importantly, they argue that learning is not simply about collecting information. It requires curiosity, discipline, experimentation, and the willingness to admit when you do not know something. As AI removes many technical barriers, the ability to ask better questions, solve problems, manage projects, communicate effectively, and continually adapt may become even more valuable. Why an entrepreneur's business can only grow as far as the entrepreneur is willing to grow How to build a disciplined habit of continuous learning Why asking for help can be a sign of strength rather than weakness How AI is dramatically reducing the time required to acquire new capabilities Why hands-on experimentation can be one of the fastest ways to understand emerging technology How founders can create a culture of learning throughout their organizations Why curiosity and adaptability matter when industries are changing rapidly How AI can remove technical barriers without replacing human creativity and judgment Why problem-solving, project management, and communication remain critical skills How entrepreneurs can use AI as a learning tool to expand what they are capable of building

  7. Sep 25

    EP233: How To Catch The Next Tech Wave Before Everyone Else

    The Biggest Opportunities Often Appear Before A New Technology Reaches The Mainstream In this episode of Start, Scale, Exit, Repeat, Colin C. Campbell, Michele Van Tilborg, and members of the Startup Club community explore how entrepreneurs can recognize emerging technology waves and position themselves before the rest of the market catches up. From dial-up internet and broadband to cloud computing, new domain extensions, social media, AI, and AI agents, Colin shares lessons from businesses built around major technological and regulatory shifts. The conversation examines why startups can often move faster than established companies and how founders can use that advantage to experiment, adapt, and enter emerging markets early. More importantly, they break down practical ways to spot the next wave, including surrounding yourself with new technology, watching where conversations are accelerating, noticing when technology changes your own behavior, and looking for second-order opportunities created by a larger transformation. How technology and regulatory changes can create entirely new markets Why large companies often move more slowly than startups during major shifts How the technology adoption curve and the "chasm" can help founders evaluate emerging opportunities Why founders should actively experiment with new technology instead of simply reading about it How increased conversation and market noise can signal an emerging trend Why changes in your own behavior can reveal technologies with broader potential How second-order opportunities can become larger than the original innovation Why AI agents represent another major opportunity emerging from the broader AI wave How professionals and service providers can adapt their expertise instead of competing directly against AI Why execution becomes even more important as technology makes launching a business easier

  8. Sep 25

    EP232: Decision Fatigue: How Entrepreneurs Can Reduce Stress And Regain Control

    When Every Decision Lands On The Founder, The Business Eventually Hits The Limits Of The Founder In this episode of The Complete Entrepreneur, Colin C. Campbell and Michael Gilmour explore the decision fatigue, financial pressure, workload, and constant uncertainty that can make entrepreneurship overwhelming. From employees escalating minor decisions to founders struggling with cash flow, fundraising, difficult partnerships, and the pressure to keep up with AI, they share personal stories about situations that consumed their time and attention. The conversation examines how entrepreneurs can push decisions closer to the people with the knowledge to make them, create room for controlled mistakes, and stop spending their days fighting fires. More importantly, they discuss how the right people, funding, systems, and leadership structure can reduce unnecessary stress while allowing founders to focus on strategy and growth. The goal is not to eliminate pressure from entrepreneurship, but to build a company where every problem no longer depends on you personally. Why founders become overwhelmed when every decision is pushed back to them How assigning responsibilities instead of tasks can reduce decision fatigue Why employees need permission to make decisions and learn from non-fatal mistakes How financial pressure can distort judgment and consume a founder's attention Why startups need enough runway to reach clearly defined stage gates How bootstrapping and customer-funded growth can reduce dependence on outside capital Why raising money can become a major distraction from actually building the business How difficult business partnerships can drain energy that should be spent on growth Why systems, strategic planning, and strong leaders can reduce the founder's workload How entrepreneurs can move from constantly firefighting to working on the business instead of inside it

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In each episode, we explore the things that make serial entrepreneurs tick. With a variety of guests and a "live" audience you'll learn the hacks, tips, and techniques that entrepreneurs use to start, scale, and exit their businesses, and then repeat the process. Recorded LIVE on Clubhouse's Largest Club Startup.club.

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