On today’s episode of Bootstrapped Web, Brian and Jordan are joined by Ian Landsman from HelpSpot. Ian has made product after product over the years, from UserScape to HelpSpot to LaravelJobs and Thermostatio. You can find him on Twitter or you can learn more about him on his website.

Brian, Jordan, and Ian are talking all about podcasts, business models, and privacy on the internet. They also go over the lessons they’ve all learned from previous products and projects they have been involved in.

Here are today’s conversation points:

• Ian’s potential new podcast: structure or no structure?
• Hey, Clubhouse, and other email services
• The hidden cost of privacy and complacency in a product
• Previous products, projects, and the lessons learned
• How involved Ian, after being 15 years into HelpSpot
• What does feature development look like for Ian?
• Optimizing websites as supplementary platforms
• Business models: per user, paying per clients
• Are demos worth it?
• Affiliate programs and consulting hang ups for ProcessKit
  • Third party hosting and consulting companies
• Real-time brainstorming about onboarding consultants

Ian Landsman

Clubhouse

Hey

SellerFlows

ClickFunnels

SunriseKPI

Productize

Audience Ops

ProcessKit  

Carthook 

As always, thanks for tuning in. Head here to leave a review on iTunes.