TMBA 634: The ‘Downside Protection’ of Investing in Bootstrapped Businesses

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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.”

See the full transcript below

Listen to this week’s show and learn:

  • Reasons we don’t share more DJ updates on the show (02:55)
  • Things to think about re. building a community for your business (10:15)
  • Why ‘conception’ is the most important thing to think about when creating communities (19:05)
  • The complicated experience of growing teams and team communication (26:46)

Mentioned in the episode:

Before the Exit – Our New Book
Partner With Us
The Dynamite Circle
Dynamite Jobs
Post a Remote Job
Dynamite Deals
Tropical MBA on YouTube
Dynamite Jobs – Remote Recruiting Sales Page
Rob Walling
Tiny Seed
StartUps For the Rest of Us
Start Small, Stay Small
Stack Overflow
Joel Spolsky
Jeff Atwood
Einar Vollset
Dave Rodenbaugh
Jordan Gal
Jason Calacanis
Sam Parr
Rand Fishkin
Indie Hackers
The Stair Step Approach to Bootstrapping
Empire Flippers
My First Million Podcast

Enjoyed this podcast? Check out these:

TMBA420: No Epiphany Required
TMBA554: A Healthy Equilibrium
TMBA557: Ascending the Staircase

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Dan & Ian


Full Transcript

(Transcript Forthcoming)

(Transcript Forthcoming)