How Much of Your Decision Is Driven by the Psychological Profile of the Founder?

Tiny Seed co-founder Rob Walling joins Dan to share insights about why bootstrapped businesses, particularly Software as a Service (SaaS), are becoming increasingly desirable to investors, partly due to the ‘downside protection’ they offer. They also discuss the pros and cons of serving ‘two sided marketplaces’ and why Rob has recently updated his ‘Stair Step Approach’ to entrepreneurship:

“One thing that has changed is that there are a lot more opportunities to do ‘step one’ businesses that are recurring revenue from the start, like Shopify add ons .. If there's already a marketplace in place, it takes a huge amount of complexity off your plate .. it allows you to build the business and then learn the other stuff as you go.”