Startup.Club
243 episodes listed below
Entrepreneur lessons from the live room.
Start. Scale. Exit. Repeat. is a live Startup Club business conversation built around entrepreneur problems that feel immediate, not theoretical. Episodes move from AI use and Kickstarter launches to self-doubt, trade shows, failure, and the personal habits that keep entrepreneurs moving.
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Start. Scale. Exit. Repeat. is a live, community-driven business show for entrepreneurs who prefer candid entrepreneur talk over packaged theory. It moves quickly. Recent conversations cover AI, fear, failure, resilience, Kickstarter campaigns, trade shows, repeat startup patterns, and the personal systems that help entrepreneurs keep going. The show has a practical bias. A topic may begin with a theme song, a room-filling pause, a technical hiccup, or a casual aside, but it usually lands on an entrepreneur lesson. AI comes up again and again. Speakers discuss using ChatGPT as a coach, applying AI to weight loss and planning, turning it into a business helper, and wrestling with whether AI-made music or apps still feel original. The show is interested in tools, but it is skeptical of magical thinking. One repeated point is that AI can accelerate work, yet the entrepreneur still has to supply judgment, story, taste, and persistence. The emotional material is just as central. Episodes address fear, self-doubt, rumination, stress, disappointment, and the practical ways entrepreneurs can calm down enough to think clearly. That can mean breath work, writing by hand, or simply admitting that setbacks are part of the job. The live format gives the show a rough, energetic texture. Speakers interrupt, agree, challenge, circle back, and pull examples from real launches and entrepreneur life. The Kickstarter episode is especially hands-on, treating a campaign as something unfolding in real time rather than as a neat case study. The result is part business workshop, part entrepreneur support room, and part running argument about what it takes to keep building.
Made for: For founders, entrepreneurs, and entrepreneurial professionals who want practical talk about growth, resilience, AI, launches, and business development. It especially suits listeners who like candid discussion more than polished business theater.
What sets it apart: The show’s edge is its live-room messiness: problems are worked through in public, with real examples from campaigns, conferences, AI experiments, and entrepreneur setbacks. It treats the entrepreneur’s mindset as seriously as the business model.
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.
Based on 5 episodes we listened to · September 2026
It makes entrepreneurial judgment practical by pairing community experience with recurring questions about AI, execution, and founder psychology.
Start. Scale. Exit. Repeat.: Serial Entrepreneur: Secrets Revealed! turns founder problems into live, communal working sessions. Colin and co-host Michelle Van Tilburg frame a practical question, then invite the room to complicate it with experience.
A Kickstarter launch is underway; you get the mistakes before they become a victory lap.
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Short reviews from the PlayNext desk, based on the episodes we processed.
Practical life-hack advice with a useful AI example.
This conversation keeps its focus on practical life hacks rather than business theory alone. It treats the entrepreneur mindset as something that can shape everyday routines as well as work, and the clearest example is the use of ChatGPT as a weight-loss coach by photographing…
A practical reset for entrepreneurs stuck in fear and self-doubt.
This episode centers on the fear and self-doubt that can keep aspiring entrepreneurs from moving ahead. Start, Scale, Exit, Repeat keeps the discussion steady, with Dr.
A messy AI money debate that keeps circling originality.
The episode frames a sharp AI-money question around one clear premise: can AI help someone build real wealth, or does it mostly serve up polished advice with little substance?
A live Kickstarter launch becomes a practical lesson in story, human connection, and campaign execution.
The episode frames a live Kickstarter launch as a grounded look at what a strong campaign asks for. It keeps circling back to story, suggesting that people respond first to human experience and that an entrepreneur has to present that experience with clarity.
A grounded look at how AI costs and task fit shape which tools are worth paying for.
The episode treats AI adoption as a practical cost-and-fit question: which tools justify paying for, and which tasks do not. It keeps coming back to the divide between people who can carry multiple subscriptions and people who have to choose with care, using the early internet…
Rob Walling on bootstrapped SaaS growth, plateaus, and exits — with founders who lived them.
Abbey Ashley's playbook for turning your job skills into a virtual assistant business.
SaaS operators on scaling, pricing and AI, metrics included.
Alex Blumberg interviews guests like Megan Phelps-Roper and Shane McAnally about failure and reinvention.
Colin argues that choosing a scalable idea can make running a company easier than operating a small business, citing his wife's school and its 110-student ceiling.
On Start.
Michael Gilmore describes Australia's budget announcing a 30% capital gains tax and a 10% tax on unrealized 401k gains, including a friend whose $50,000 stake is now valued at $60 million.
Life hacks run the room.
The show opens by asking whether AI can help make a million dollars.
Fear is the central theme.
This episode introduces a live Clubhouse show about entrepreneurship, featuring a motivational theme song that highlights the challenges and resilience of startup founders.
This episode discusses the reality of entrepreneurial failure and strategies for managing disappointment and bouncing back.
They open on a live Kickstarter launch.
Hosts discuss patterns behind repeat startup wins and whether there is a formula for building wealth through serial entrepreneurship.
This episode provides tips on how to succeed at trade shows and conferences for entrepreneurs.
Serial entrepreneurs discuss facing startup fears and share tips for success in 2026.
This episode discusses the seven values of highly effective founders, aiming to decode the habits that lead to entrepreneurial success.
The episode discusses 26 best startup ideas to launch in 2026, targeting aspiring entrepreneurs.
Host discusses eight principles for winning at the startup game with guest Eric Mulca, founder of Artist Shaving.
Start.
The host discusses purpose-driven growth with guest Cesar Quintero, focusing on systems for scaling businesses and avoiding founder pitfalls.
This episode discusses franchising as a gateway to entrepreneurship, covering the franchise market and how to succeed as a franchisee.
This episode discusses how entrepreneurs can leverage AI and data to launch and scale successful startups.
This episode discusses starting a business without investors, busting myths about venture capital, staffing, risks, and leadership in entrepreneurship.
Serial entrepreneurs discuss favorite books and movies that have impacted their entrepreneurial journey.
A live podcast discussing whether startups should consider venture capital, featuring a venture capitalist guest.
A live Clubhouse show exploring the secrets of serial entrepreneurs, featuring an interview with Dr.
Serial entrepreneurs discuss facing startup fears, including fear of failure and success, and share strategies to overcome them.
A live Clubhouse show featuring serial entrepreneurs sharing tips on starting, scaling, and exiting businesses, with a focus on a new newsletter offering growth hacks and AI tips.
A live Clubhouse show discussing top business trends for 2025 with audience participation and expert insights.
This episode explores the distinct mindsets required for starting versus scaling a business, drawing from the book 'Start, Scale, Exit, Repeat' and featuring insights from a CEO guest.
This episode explores how startup founders can implement AI to scale their businesses, featuring insights from guest Jose Marino on ed tech and entrepreneurial strategies.
The hosts celebrate their book's success and awards while introducing a discussion on balancing boss and coach leadership styles in entrepreneurship.
This episode discusses a time-to-sell index designed to help entrepreneurs decide when to sell their startups based on empirical data.
This episode features a live debate on the differences between founder mode and manager mode in business leadership, based on a Wall Street Journal article and the host's personal experience as a founder and investor.
The host discusses the Ultimate Startup Checklist from a guide, covering essential steps for launching a business.
Serial entrepreneurs discuss how to come up with the next million-dollar business idea, sharing tips and personal experiences.
Host discusses recent successes and introduces an interview with Eric Malka, founder of The Art of Shaving, about scaling a business from nothing to a Fortune 25 sale.