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Roy Osing
Former President and CMO who scaled a startup data company to $1B in annual revenue; author, entrepreneur, and business advisor with 40+ years of leadership experience.
4
APPEARANCES
4
PODCASTS
012
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SEP 7
Aug 24, 2026
🚀 Busting Killer Roadblocks: The Operational Leaps for Unstoppable Scaling
9:15

Ian TaitHOST
So what single piece of advice, and I know that's difficult, Roy, what single piece of advice can you give a business leader wanting to step out and do things differently?
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9:25Roy OsingGUEST
And just before I, I get into that, Ian, I just wanna hit on a couple of, um, of, of points around actually not just overcoming the challenges, but actually getting people to accept the moves that we're trying to make because there's two things that were really, really important here.
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9:46Roy OsingGUEST
There's nothing more effective, okay, than getting people to accept change than when they see the results of that change in front of their very eyes.
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10:01Roy OsingGUEST
So, uh, m- I personally, um, focused on making sure that that revenue line was going the right way, and not just talking about the need for change, but showing that it worked.
BE DIFFERENT or Be Forgotten: Roy Osing on Audacious Leadership and Taking a Startup to $1 Billion in Sales
6:32

Henry ChiweteluHOST
What were some of the most important decisions that made that growth possible?
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6:37Roy OsingGUEST
Yeah, and this is really going to be simple stuff, and people are going to scratch their head and say, what? Did that stuff really work? But let me just give you – there wasn't one thing, okay, Henry? There never is.
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6:57Roy OsingGUEST
all working relentlessly towards a single endgame, where learning through execution is actually the modus operandi.
10 MINS LATER
Be Different or Be Dead with Roy Osing
24:26

Ryan DrumhellerHOST
But also be fast about admitting when it's looking like it's not going to work and pivot again and learn from it.
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24:34Roy OsingGUEST
Well, it's pretty obvious, but one of the problems that people have is that they operate without context.
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24:42Roy OsingGUEST
And I want to talk to you that a little bit, because without context, you can't execute.
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24:49Roy OsingGUEST
Or if you do, you're executing without some sort of picture of the end game you're looking for.
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24:57Roy OsingGUEST
And so my kind of mantra around this is you need to be context led and execution driven.
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25:04Roy OsingGUEST
And what I mean by that is the context piece should only occupy about 20% of your time.
6 MINS LATER
How to Scale From a Business Startup to $1B Without a 5-Year Plan
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5:13Kavon KayeHOST
Yeah.
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5:13Roy OsingGUEST
Being different is about being special in a way other people care about, okay? So going back to this challenge, um, we had to look for literally in every nook and cranny of this business, we had to look for opportunities to be different, and it started with the planning process.
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5:33Roy OsingGUEST
I mean, I'm gonna either make this thing or it's gonna break me, one or the other.
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5:36Roy OsingGUEST
What am I gonna do? I don't have a strategy." And so I looked around, uh, at traditional, um, uh, planning models, and none of them were helpful.
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5:44Roy OsingGUEST
Okay? It took too long, they were too complicated, and they were way too expensive.
29 MINS LATER
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34:55Kavon KayeHOST
Yeah.