Rob Walling

Josh Pigford on June 11, 2018


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This week I talk with Rob Walling, Founder of Drip! In this episode we talk about growing up in the country, learning programming, getting in to entrepreneurship as a kid, buying existing businesses and improving them, the origin of Drip and its acquisition by LeadPages and more!

Show Notes:

  • 1:43– Childhood and technology
  • 3:15– First computer! Self-taught basic coding
  • 5:30– School and influences
  • 8:32– Early entrepreneurship
  • 12:30– Double major in college- Electrical Engineering and Computer Engineering
  • 14:10– Personal preferences and structured programming
  • 16:42– Coding and the potential of the upcoming Web
  • 20:08– Transitioning from consulting to contract work
  • 23:35– New ideas and projects
  • 25:55– Stumbled upon .NETinvoice and wanted to buy it
  • 28:30– “Groundbreaking” improvements to .NETinvoice
  • 32:15– Having four to six different sites at once
  • 35:55– 2009 and 2010= Very busy!
  • 38:40– HitTail is acquired
  • 38:55– Paying yourself and saving money
  • 40:44– Taking risks
  • 42:24– Transition from HitTail to Drip
  • 47:16– Competition
  • 50:02– The Drip team in 2015
  • 51:36– Biggest struggle as a company
  • 52:56– Conversations with Leadpages
  • 55:00– Should we raise a small round of funding?
  • 56:30– Acquisition
  • 59:01– How the team dealt with the acquisition process
  • 1:02:23– Leaving Drip and future plans

How to reach Rob: Twitter • Website

Josh Pigford

Josh is most famous as the founder of Baremetrics. However, long before Baremetrics and until today, Josh has been a maker, builder, and entrepreneur. His career set off in 2003 building a pair of link directories, ReallyDumbStuff and ReallyFunArcade. Before he sold those for profits, he had already started his next set of projects. As a design major, he began consulting on web design projects. That company eventually morphed into Sabotage Media, which has been the shell company for many of his projects since. Some of his biggest projects before Baremetrics were TrackThePack, Deck Foundry, PopSurvey, and Temper. The pain points he experienced as PopSurvey and Temper took off were the reason he created Baremetrics. Currently, he's dedicated to Maybe, the OS for your personal finances.