
Bootstrapped Web
Brian Casel (@casjam) and Jordan Gal (@jordangal) share their raw and real behind-the-scenes of their entrepreneur journeys. From bootstrapping software startups to raising money to selling and exiting businesses, to growing teams and the emotional rollercoaster that is startup life. It's all here in Brian and Jordan's weekly(ish) updates.
Latest episodes

11 snips
Apr 5, 2024 • 1h 7min
Make it Rough
The podcast discusses idea hunting, competitors, portfolios, rough products, customer success, weekly pricing, and productized services. They also touch on earthquakes and supplements, offering a mix of business insights and personal anecdotes.

Mar 29, 2024 • 1h 6min
Creating Content & New Product Ideas
From contrasting urban environments in the Northeast and Texas to navigating content creation challenges, the hosts dive into new product ideas, AI in ecommerce, and customer success strategies. They discuss tapping into demand, launching products successfully, and even controversial THC drinks.

Mar 15, 2024 • 52min
Ideas & Tech Stacks
Topics include exploring new ideas at conferences, building in Laravel vs. Rails, training customer success, leveraging audience as employee vs. founder, and discussing travel energy.

Mar 8, 2024 • 55min
The internet is a confusing place
The podcast covers SaaS trends, pivots, personal energy, eCommerce space, bootstrapping, product idea mining, platform risk, and even elementary school talent shows. It delves into efficient product development services, challenges in e-commerce landscape, reevaluation of product-market fit, and AI adoption in business.

Feb 23, 2024 • 1h
Charging for Onboarding
Launching a consultancy, generating pipeline, SDRs outsourcing vs in-house, paid customer onboarding, and a fun segment on daddy-daughter dancing.

Feb 16, 2024 • 54min
New Directions
SaaS entrepreneur, Brian, and entrepreneur, Jordan, discuss AI, Mark Zuckerberg's criticism of Apple, drawbacks of version one products, parenting concerns with technology, internal structure and product adaptation, evolution of pricing strategy, and aligning content and service.

Feb 2, 2024 • 1h 2min
2024 Calculus
Homepage experiments, marketing costs, product-led growth, bootstrapper game, cold outreach, over-correcting, shingles, Vienna trip, new strategy on offers product, investing in customer success and retention, challenges in venture land, potential of spatial computing and importance of FOMO.

Jan 19, 2024 • 46min
Enough Time
The podcast discusses topics such as time management, hiring a customer success person, structuring the day, different calendar tools, Basecamp's new product, tracking marketing and designing websites with Framer and Statimic, product strategy consulting with SaaS companies, and children's creativity and tech tools.

Jan 12, 2024 • 35min
Pipeline Energy
The speakers discuss their ski trip to Montreal and the challenges of flight issues. They explore the importance of hiring a dedicated customer support person. They discuss closing deals and introducing a new product offering. They talk about generating a new pipeline and the challenges of estimating projects. They discuss the challenges of energy management and changing market dynamics. They also discuss improving their business and launching a new website.

6 snips
Jan 5, 2024 • 1h
Blank Canvas
Brian and Jordan discuss various topics including handling pressure and deadlines, creative strategies for promoting their business, fundraising preparation, optimal timing for fundraising, pressure on monthly goals in bootstrapped vs funded companies, and the concept of adjusting or pivoting in a startup.
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