Ep 024: Darryl Praill

Why owning everything doesn’t mean doing everything and not letting optimism replace truth with Darryl Praill

Chief Marketing Officer at VanillaSoft, Darryl Praill, joins us as we discuss his entrepreneurial journey including his breakdown after taking on the responsibilities of everyone he worked with.

A veteran Marketing Executive with over 25 years’ experience spanning startups, acquisitions and IPOs, Darryl shares how to handle competitors who are bigger than you, overcoming the fear of people judging you, and the habits that have led to his success.

In this episode we discuss:

0:56                   Quick Intro to Darryl Praill

01:15                 What you might not know about Darryl Praill

03:02                What Darryl Praill is currently focused on

04:38                Where do you start when your competitor has you outgunned?

06:16                 What happens when you hit your milestone to be number three?

07:14                 The 15 million dollars, is that something you have done or will be in pipeline to do?

09:41                 Being Honest – Play strategically, not to your vanity/insecurity

11:15                  What is the biggest fight you have lost?

15:06                What are the habits that have led to your success?

17:54                 Overcoming the fear of other people judging you

21:11                 When you got it horribly wrong, can you tell us a little about that?

Quick Juice Questions

23:36                Do you invest? And if so, what do you invest in?

24:18                What most inspires you? And when and where are you most inspired?

25:38                Which book has most inspired you and changed your thinking the most?

27:28                What’s the best piece of advice you’ve ever received and/or given?

30:23                If there’s one last bit of Executive Juice you can share for people who want to get to the top of their game, what would it be?

31:54                Time block – 10 minutes or half an hour to do social media activities rather than spending hours a day on social media?

Links Mentioned:

Books Mentioned:


  • As an executive, you need to say, “What fights can I win?”
  • Our relationship doesn’t necessarily cost money if we help each other out.
  • You have to outsmart your competitors.
  • Be honest with yourself and your key stakeholders so that everybody understands what you’re up against and what your strategy is.
  • Communication generates alignment; and once we all have alignment, everybody executes the plan.
  • You cannot change others; you can only change yourself.
  • When it comes to public space, not everyone is going to agree with you.
  • If you try to be everything to everyone, you end up being nothing to no one.
  • Learn, move on, and do it again.