SFN222: Overcoming the Trials and Tribulations of Entrepreneurship (and Life)


If you are trying to start a business, you’ve probably been through some trials and tribulations along the way… and today we’re talking to someone who triumphed over their year of hell and came out stronger on the other side.

Kyle Racki is the CEO of Proposify, a seven-figure software business with $250k MRR after only three years. We discuss the start of his entrepreneurial journey, some of the challenges he had to overcome, and how he is growing Proposify.


In This Interview I Ask:

  • 1:30 - How is Proposify doing? Can we talk revenue numbers?
  • 2:50 - How did Kyle get started in business in the first place?
  • 6:10 - What was horrible about Kyle’s agency?
  • 9:15 - Was there any point where Kyle hit a breaking point?
  • 12:40 - When did things start to go south?
  • 22:35 - How did Kyle deal with all of the emotional challenges?
  • 26:15 - Why did Kyle leave the Jehovah's Witnesses?
  • 33:20 - What was the next turning point for Kye, where Proposify started getting growth?


Year(s) of Hell

Kyle struggled through years of running a digital agency he didn’t enjoy, that agency’s debt, the arduous process of selling the agency, a family death, leaving his religion, and losing connection with other family members.

There were a lot of times he wanted to quit, but two things kept him going.

  1. Kyle had a partner to support to him: Kevin Springer, a former colleague and Proposify’s COO.
  2. Fear of failure, and not leaving a legacy, drove him to keep trying even when things were tough.


“There Should be a Basecamp for Proposals”

While running an agency and just getting by, Kyle had a thought that eventually grew into Proposify: “There should be a basecamp for proposals.” He wireframed the product back then, but it was almost ten years later that they actually started building the product.

Proposify didn’t take off immediately. They raised $270k in funding, but they had a product problem: trial users weren’t converting into paid users.

They hired another developed, focused on customer development, and identified the biggest pain points in their product. Creating simple templates, and a revamped onboarding process, changed everything. Proposify went from flatlined for 17 months to doubling the MRR in one month.