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I Watched a Founder Change His Mind 8 Times in 3 Months
If you’ve ever felt stuck in planning mode, this episode will probably feel familiar.
You evaluate an idea.
You start moving forward.
Then uncertainty shows up… and the strategy changes.
In this episode, Ray shares the story of a founder who pivoted through multiple strategies in just a few months—not because he lacked intelligence or effort, but because he was waiting for certainty that never comes in business.
The real trap wasn’t the ideas. It was the belief that the right move should feel 100% clear before committing.
If you’re rowing hard but feel like the business isn’t moving forward, the issue might not be effort—it might be the constant search for guarantees.
What You’ll Learn in This Episode:
- Why constantly changing strategies keeps founders stuck in planning mode
- The difference between finding something that works and committing to make it work
- Why most results in business live on the far side of a J-curve
- How uncertainty triggers the “amygdala hijack” that causes endless pivots
- Why thinking in probabilities is more effective than looking for certainty
- How a lack of clear strategy creates confusion about tactics
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This podcast is where Ray thinks through hard decisions — especially when the usual playbooks stop working.
If that approach resonates, that’s what you’ll find more of here.
New to the show? The “Start Here” playlist outlines what the podcast is about and how to approach it:
https://player.captivate.fm/collection/a7577a6f-15da-4521-b214-35e4e47f320b
Transcript
You aren't looking for the thing that works.
Speaker A:You're committing to making it work.
Speaker A:And if you don't get that distinction, as I didn't for a long time, you'll stay stuck in planning mode forever, working your ass off, making zero progress.
Speaker A:And I'm, and again, I'm saying this because I experienced it, I lived it now, by the way, if you like reading this stuff and actually applying it, that's what the newsletter is for.
Speaker A:You can hop in@raiseemail.com for free.
Speaker A:So I was working with this, this MSP business owner who was driven mad by uncertainty.
Speaker A:Is the, is the best way that I can frame it.
Speaker A:And I, because I, I really mean, just like it was driving him crazy.
Speaker A:And you know, we started with, with him, you know, wanting a sales audit.
Speaker A:You know, he's like, you know, I'm not sure what our bottlenecks are, what the constraints are.
Speaker A:I'd love for you to take a look and kind of build out a road map and figure out what the, you know, what the next six months or so looks like.
Speaker A:So cool.
Speaker A:All right, so we, we get our agreement and we're ready to go.
Speaker A:And then we last minute changes his mind.
Speaker A:I go, no, I'm not ready for that yet.
Speaker A:Okay, cool.
Speaker A:Almost immediately afterwards, like, hey, you know, I want to hire an sdr.
Speaker A:I want somebody like, local that can, they can do some canvassing, they can go down to local events.
Speaker A:They can also be making some calls.
Speaker A:So we start marching down that road, helping them with some recruiting, changes directions again.
Speaker A:Right now, Ray, that's, that's, I think that's too expensive.
Speaker A:I just don't know if it's going to work.
Speaker A:You know, I, I could do some of the events in the interim.
Speaker A:I, I'd rather hire somebody abroad.
Speaker A:We do recruiting right at MSP Sales Partners.
Speaker A:So we start sourcing talent and we're sending over really good candidates because we, we screen with sales management experience.
Speaker A:Like that's what we do.
Speaker A:It's what I've done my whole life.
Speaker A:It's what my team's done.
Speaker A:So we're sending over good candidates.
Speaker A:And he's like, yeah, you know, these are really good.
Speaker A:I just, I just need to see more, I just need to see more candidates.
Speaker A:I just, I'm just not sure, I'm not sure who to pick and say, okay, cool, so we, we get them more candidates and then he, he puts them through this, like, very, very extensive, like, process.
Speaker A:Multiple personality tests and multiple interviews, like the whole nine yards, all trying to eliminate Uncertainty.
Speaker A:And we get down to the offer stage.
Speaker A:And he's like, okay, well, I'm not sure if I like both of them.
Speaker A:So, like, should I hire one or should I hire two?
Speaker A:And we, we have that conversation.
Speaker A:Then it's like, okay, whoa.
Speaker A:You know, like, hey, like, I like both of them, but I want to negotiate on pay.
Speaker A:I want to pay a couple hundred dollars less per month.
Speaker A:Actually, you know what?
Speaker A:Like, it's offer day.
Speaker A:Like, you got to send them an offer.
Speaker A:We've had all the conversations.
Speaker A:Actually.
Speaker A:I don't actually know if this is going to work.
Speaker A:Like, I'm not ready for this.
Speaker A:I don't know if the SDR strategy is what we want to do.
Speaker A:We're thinking about growing through acquisition this year and not necessarily, you know, going to get our own clients.
Speaker A:Like, we want to, we want to buy some businesses.
Speaker A:So I'm not sure if this is aligned.
Speaker A:And this was the pattern, like, over and over.
Speaker A:Now, I'm not saying this to be critical.
Speaker A:Like, I'm saying this because I recognize this behavior very well.
Speaker A:I've lived it like, this is a past version of me.
Speaker A:And here's what I learned.
Speaker A:The source of all of this comes down to looking for certainty.
Speaker A:Instead of accepting that as business owners, as CEOs and entrepreneurs, we simply operate in uncertainty, right?
Speaker A:Like, it's, it's just, it's just what we do.
Speaker A:We don't think find certainty, we make it.
Speaker A:That is the job.
Speaker A:We, we make bets.
Speaker A:We don't, we don't think in terms of right and wrong.
Speaker A:And hey, if this is a, this is the wrong decision, it's over, right?
Speaker A:Like, we think in terms of uncertainty and probabilities.
Speaker A:I feel 70, 75% sure this is going to work out.
Speaker A:Never 100%, but like, that's the job I chose and that's why we get paid the way we do or, or don't, like, you know, unfortunately.
Speaker A:But when you refuse to accept that, when you keep looking for uncertainty, like thinking that you're just going to find it, thinking that you're going to stumble across it, like it drives you crazy because you start operating from your amygdala, right?
Speaker A:Like the, the reptile part of your brain.
Speaker A:And it's impulsive, it's like panic driven.
Speaker A:It's fight or flight.
Speaker A:And here's what happens when you combine that with, with the bias for action that that's required to be an entrepreneur.
Speaker A:You end up changing all of the time because you're taking that fight orf flight mode.
Speaker A:But you're constantly staying in motion because we have this bias for action, and you're just.
Speaker A:You're pivoting constantly.
Speaker A:We're going to go this direction.
Speaker A:No, we're going to go this direction.
Speaker A:Actually.
Speaker A:This direction.
Speaker A:I'm not sure about that direction.
Speaker A:And there's two fundamental problems with this.
Speaker A:Like, first is all of the big results in business happen down the road, and almost everything in business has an exponential curve on it.
Speaker A:You know, you think about an employee's productivity or a marketing strategy or a sales process, it's.
Speaker A:It's got this exponential curve.
Speaker A:The early part is the hard part because you're figuring things out, right?
Speaker A:But you.
Speaker A:But if you stick with it, if you learn how to do it, if you get through what Seth Goen calls the diplomatic.
Speaker A:If you get in the reps and you build the right systems, get the right people in, get the right plays done, the results come later, and they.
Speaker A:And they go strong J curve.
Speaker A:But if you're constantly changing directions, you never actually get to experience that.
Speaker A:The second problem is, and this is the sneaky part, when you're constantly pivoting, it keeps you in planning mode.
Speaker A:And planning mode is the safe space, right?
Speaker A:Because it feels safe to be building, it feels safe to be thinking, to be planning.
Speaker A:But when it comes time to execute, like, that's when the uncertainty actually kicks in, right?
Speaker A:And.
Speaker A:And that's when it starts to feel unsafe.
Speaker A:So you go, you know, maybe we need to change directions now.
Speaker A:Like, we've done all of this stuff, so take, like, this example.
Speaker A:All of the interviewing, all of the recruiting, all of the comp discussions, all of the one or two hires, all, like, everything that you can imagine.
Speaker A:Then when it gets down to, like, pulling the trigger, I don't know, I'm gonna back out.
Speaker A:And you stay in that safe space of planning, or you hit execution mode, which is hard, right?
Speaker A:Going back to the first problem, that's the hard part.
Speaker A:And then you bail before the results show up.
Speaker A:And either way, you never actually get the outcome that you want.
Speaker A:So here's what I've learned, like, for myself and dealing with this.
Speaker A:First, accept that uncertainty is simply part of our job description, right?
Speaker A:As CEOs, we operate in that 55 to 85 confidence range, right?
Speaker A:If.
Speaker A:Because if it's.
Speaker A:If it's higher than 85%, 95%, like, we're not really making, like, strong, bold decisions at that point, right?
Speaker A:Like, it's.
Speaker A:It's more of like, yeah, I feel pretty good about this.
Speaker A:Let me weigh the returns, Annie.
Speaker A:Duke actually has a really good book called Thinking in Bets.
Speaker A:You know, the, the poker player.
Speaker A:And it's a really solid way to, to think about decisions in general and, and not necessarily think, is this the right move or the wrong move?
Speaker A:It's like, is it a good bet or a bad bet?
Speaker A:Right?
Speaker A:It's, it's not.
Speaker A:Oh, my God.
Speaker A:If it's the wrong move, like, something catastrophic is going to happen here.
Speaker A:Like, it's a.
Speaker A:Into the end of the business, you know, like, you're not, you're not in fight or flight mode.
Speaker A:It's like, nah, Yeah, I feel 80% about this one.
Speaker A:That's good enough.
Speaker A:It's a smart bet because we don't, we don't have the luxury of a hundred percent.
Speaker A:And as soon as we accept that, it helps us get out of the amygdala part of our brain into the calmer, more strategic part of the brain where the bias for action isn't actually as dangerous.
Speaker A:Second thing that I've learned is that sometimes you've just got to slow the fuck down and clarify what the strategy is.
Speaker A:You know, I hear, like, a lot of entrepreneurs, like the, the old Facebook, like, move fast and break things.
Speaker A:Yeah, that's great, but not if you don't have a North Star on where you guys are going.
Speaker A:If everyone knows what the primary target is, then, yeah, moving fast and breaking things is great.
Speaker A:You're all moving in generally the same direction.
Speaker A:You're rowing in the same direction, awesome.
Speaker A:But if the strategy isn't really clear and everyone's rowing in different fucking directions and everyone's just running around in the business isn't making a lot of progress, you've got a ton of activity, a ton of effort, a lot of motion and no real progress.
Speaker A:And sometimes the answer, and this is, it's harder than it sounds, but it's.
Speaker A:The answer is you just gotta slow down, like, calm the bias for action for just a second, clarify what the strategy is.
Speaker A:Because one of my mentors, like, hammered this to me probably because, like, going through this exact same thing that I'm telling you about is, like, tactics follow strategy.
Speaker A:And if you're, if you're really unclear on what tactic you're supposed to be using, like, if you're constantly confused and there's just a lack of clarity, a ton of uncertainty, a lot of times that's a symptom that you just don't have a clear strategy underneath.
Speaker A:And then the third thing is once you commit to a plan or commit to a strategy or commit to a tactic, then fucking commit, right?
Speaker A:Like, accept that you're.
Speaker A:You're going to have to make it work.
Speaker A:Like very few things in business, or at least like anything that's worthwhile, very few of them come easy.
Speaker A:Every business strategy is hard.
Speaker A:Most tactics that are, that are, are worthwhile are hard.
Speaker A:There's things to learn, there's things to iterate.
Speaker A:And I have found very few of them that work very quickly and very well, or at least not sustainably, right?
Speaker A:Like very hacks that might, might go away overnight or something like that.
Speaker A:But like, you're not looking for the thing that works, you're committing to making it work.
Speaker A:Because, like, I promise you, if you don't have that mindset, nothing is going to work.
Speaker A:You'll constantly be changing directions.
Speaker A:You're going to invest a ton of time, ton of money, ton of effort, and, and you don't make progress if it's more like, hey, you know, we're gonna go this direction.
Speaker A:Ah, it's a little hard like that one.
Speaker A:That one feels a little unsafe.
Speaker A:I'm not quite certain on that one.
Speaker A:Okay, we're gonna go over here instead now, actually, we're gonna, we're gonna go over here.
Speaker A:Like when you commit, commit, because like, like I said, like, none of them are easy.
Speaker A:And the things that are easy usually aren't worth a candidly.
Speaker A:So I don't say this critically.
Speaker A:I, I say this passionately because I have, honest to God, I've lived it, I've experienced it, and I have gone through it so many times that these lessons are what.
Speaker A:I can see it in other people so easily almost.
Speaker A:I can almost feel like sympathy, like the.
Speaker A:Feel how that person's feeling and know that I had to go through it enough times to learn these lessons.
Speaker A:So if you find yourself really frustrated, like working really hard, if you're not making progress, I genuinely hope that this message resonates.
Speaker A:I hope.
Speaker A:Hope you hear what I'm saying, and I sincerely hope that it helps.
Speaker A:Adios.
