#25: Devil’s Advocate

We talk about dollar stores, dogs and babies, the new Helpspot release, support contracts, requiring a credit card at signup, pricing and recurring billing, info-products, SaaS being unsatisfying, digging new holes, the point of growing, all software going to zero.

• Helpspot – Ian’s helpdesk product.
• Snappy – Ian’s newest product.
• Uberdeck – Andrey’s mobile-app marketing product.
• Stripe – payment processing service.
• Star Trek Generations
• Ian’s “all software is going to $0.00” theory
• Edge of My Seat – Perch, Rachel Andrew, Drew McLellan
• Rachel Andrew on Bootstrapped.fm
• SupportOps.co – Chase Clemons
• Chase Clemons on Bootstrapped.fm
• So You Want To Be A Wall Street Programmer? – Andrey’s Book
• Ian’s newsletter
• SuccessfulSoftware.net – Andy Brice
• Andy Brice on Bootstrapped.fm

Discuss this episode with other bootstrappers in the forums.

Creators and Guests

Host

Andrey Butov

Founder of Antair

Host

Ian Landsman

Founder HelpSpot, LaraJobs, and Laracon Online.

Producer

Dave Hicking

OG podcast producer on Bootstrapped, Mostly Technical, Cheese & Weather, and Clock Radio Speakers

What is Bootstrapped?

This is the archive of Bootstrapped.fm. A seminal Bootstrapper-oriented podcast started in 2013 by Ian Landsman and Andrey Butov. The first iteration ran for 104 episodes. In 2019, Steve McLeod took over for another 139 episodes. We've set this podcast to release order so you can experience it as it was initially presented.