Kyle Racki of Proposify


Today, I’m talking with Kyle Racki, the Founder and CEO of Proposify and author of the new book, Free Trials and Tribulations: How to Build a Business While Getting Punched in the Mouth.

Continuing the trend of recurring guests, Kyle first came on the podcast 2 years ago after Proposify went through a phase of hockey stick growth. In 2015, they went from $5k MRR to $75k and then they doubled in 2016. In the years since then, their growth has continued and they are now in the ballpark of $10 million ARR and recently closed an 8-figure round of funding.

His business story is incredible, but when you learn his personal story it takes on a whole new meaning. In Trials and Tribulations, Kyle gives readers a transparent look into his personal life, from being shunned for leaving a religion he realized was a cult to dealing with divorce all while navigating the ups and downs of the entrepreneurial journey.

Rather than just rehash the book though, in our chat we dig into an area I think is particularly relevant to listeners: how Kyle went from turning down a $1.5mm termsheet one year to closing an 8-figure Series A a few years later. We also dig deeper into how those “behind the scenes” challenges have shaped Kyle and how other founders can better cope with their own struggles.

This is an interview I’d been looking forward to for a while, and I don’t think it disappoints.

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Topics covered:

  1. Brief overview of Proposify
  2. Rethinking Venture Capital
    1. Walk me through what lead you to turn down the initial $1.5mm termsheet
    2. What made you rethink things?
    3. What was the process like this time around?
    4. What has changed since closing the round?
  3. Behind-the-scenes
    1. What has been the hardest part of building Proposify for you personally?
    2. What new challenges are you preparing for as a founder?
    3. What do you do when you feel overwhelmed?
  4. Tying it together
  5. “Rapid Fire” Questions
  6. Where can listeners go to learn more?

Resources mentioned:

Where to learn more: