TMBA566: Why Do SaaS Businesses Fail?

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Today’s episode is all about software startups, and there are very few people more capable or qualified to talk about them than today’s guest.

Simon Payne first joined us on this podcast back in 2016 to talk about his role as the technical co-founder of Leadpages.

Since leaving Leadpages in 2016, Simon has gone on to found multiple software companies, including a video tool called Convert Player, and a ticketing tool that we regularly use in our own business called EventsFrame.

But, as you will hear on today’s podcast, the results of these endeavors have ultimately been a mixed bag.

Simon joins us this week to share the details of his entrepreneurial journey over the last few years, to discuss how the relationships between developers and marketers can make or break a software business, and to explain why he’s recently decided to help us build our own software platform at Dynamite Jobs.

See the full transcript below



Listen to this week’s show and learn:

  • What kinds of software businesses Simon started after he left LeadPages. (4:13)
  • The common denominators in both of Simon’s failed startups. (16:57)
  • How the tug of war between developers and marketers can actually help software startups. (20:26)
  • Why Simon decided to start working with us on Dynamite Jobs. (25:20)
  • Some insights into our own failed SaaS venture. (33:17)


Mentioned in the episode:

Before the Exit – Our New Book
TMBA Masterminds
Partner With Us
The Dynamite Circle
Dynamite Jobs
Dynamite Deals
Tropical MBA on YouTube
Simon Payne
Convert Player
Clay Collins
Seth Godin
Angel Podcast
Naval Ravikant

Enjoyed this podcast? Check out these:

TMBA349: The Technical Origin Story of Leadpages
TMBA360: Clay Collins and The Unraveling Marketing Stack
TMBA554: A Healthy Equilibrium


This week’s sponsor:

Today’s podcast is sponsored by Smash Digital.

Smash Digital is a growth agency filled to the brim with unicorn images and SEO memes.

A team of SEOs who actually know how to use SEO instead of just selling SEO to people who don’t know SEO.

An agency with so much link juice, you’ll need a mop and a bucket to clean it all up.

A group with actual skin in the game, ranking their own portfolio of profitable businesses, and offering the exact same services to clients.

If you want to have Smash Digital in your back pocket, check them out over at and a big thanks to Smash Digital for sponsoring the show.

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Have comments about the show?

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Thanks for listening to our show! We’ll be back next Thursday morning 8AM EST.


Dan & Ian





Full Transcript

(Transcript Forthcoming)

(Transcript Forthcoming)