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Serial Entrepreneur – EP58

[00:00:00] Well, let me tell you today, today, we’re talking about winning moves. This is a topic that for me, has made a huge difference in my career. I’ve done about seven or eight companies. And back in 2006, the wheels were coming off the bus.

My company had just gone public. Our revenues were lining and we really couldn’t figure out what was going wrong, but we really didn’t have a lot of systems in place. You know, we’re running it ad hoc. We’re going day by day, a lot, a lot, like a lot of you here today and startups, um, we just go ad hoc.

We just do whatever’s next. We answer the next phone call or we, you know, we, um, you know, we make the next bet. We do the next to add. We’re always just sort of flowing down the river instead of actually stopping thinking and doing strategic planning. And we have Chris Cosper here today from rhythm systems.

And, you know, I’ll tell you this. I was [00:01:00] at a trade show last week. Uh, the breakthrough conference, the first trade show, Michelle came with me that I’ve been to since the COVID has expired or is, or at least diminishing. And I have to say it was very inspirational. And Chris came on and she talked about winning moods.

And you know, that company, I talked to you about where the wheels were coming off the bus. We brought in a CEO coach and we began to do strategic planning, two days of strategic planning, 88 days of executing. And in those two days of strategic planning, we spend a lot of time talking about winning boots.

So this, this podcast, this show on clubhouse is called the serial entrepreneur club for a reason we’re trying to decode. We’re trying to figure out what it is that serial entrepreneurs do over and over again. You know, what’s the secret formula, what’s the secret sauce. And if we can figure that out, we can increase our chances of success with our startup, but I’m telling you today, we’re going to be talking about [00:02:00] one of those secret sauces in that strategic planning and figuring out winning moose Michelle, before we introduce you, Chris, I know Chris is very new to clever, has just got on this week.

So please be nice. Um, do you have anything else to add? I know Michelle will be our moderator today for the show. So about, about the trade show last week, Michelle, I mean, it was just amazing. Uh, I’ll tell you, you know, having been in the business world, gosh, you know, 30 plus years I’ve read a lot of books.

I’ve looked at a lot of, you know, frameworks and systems. I really think the system that they teach over in rhythm systems is, you know, is heads and shoulders. It’s above the rest. And, and here’s why it’s not, you know, aspirational, of course it’s aspirational, but they actually have a real framework and it is [00:03:00] extremely detailed out step by step.

And they have the coolest software I’ve ever seen for tracking the task and the goals and the B hacks, which, uh, you know, I’m hoping that Chris can tell us a little bit about, but it’s an amazing process and what I find incredible about the team and by the way, Chris Lee. The coaches, the CEO coaches for rhythm system.

And she was also a very successful CEO herself. So, um, the advice, the framework, the tools that she’s going to discuss with us today are they’re the real deal like she’s used some and, um, she made money, you know, at a company with them. So without further ado, we want to go ahead and let Chris start talking.

But before, right before we get started there, I just want to remind everybody if you’re not, you know, a member of startup club, please do join. [00:04:00] Um, we take a lot of pride and a lot of effort to bring really cool speakers on for the benefit of our members. And also you’re in this session today, you could ping in your friends.

Because it is going to be some really solid tips, um, that I think that, you know, companies of all sizes actually could implement. And Chris, I’m going to say too, that, you know, people could also implement it in their personal life for their personal goals. So Chris, why don’t we go ahead and let you get started.

But, you know, obviously winning moves are a part of the whole framework. Like kind of like, just explain to us a little bit, like how do we, you know, come up with these winning moves and how do we filter through like what the best ones are kind of give us a high level and then a little bit of information about how we could get winning moves.

We’re we’re all dying. [00:05:00] Okay. Great. Thank you, Michelle. And hello, Colin. Good to be with both of you. I, um, I think the easiest way to describe what a winning move is, is to say that it’s a very specific strategy that you want to deploy over the next three to five years, that you believe has the potential to double your business in that timeframe.

So, as we started working with more and more companies, we found that this middle range planning of three to five, Um, companies were really good at setting their targets, running the models, thinking about infrastructure, thinking about hiring head count, things like that, but where they were really lacking was thinking about what are the specific revenue moves that we’re going to do?

What are the moves in the market that we’re going to do that are going to help us accelerate the growth at the level that we want to achieve? So think of your winning moves. First of all, is that is just very simply what are the strategies that you’re putting into play right now that you think have the.

To double your business in the next three to five [00:06:00] years now, the best way that we’ve found to identify those winning moves is to think of it in terms of your broader strategy. Think, you know, start with longterm, what is your Beehag a Beehag has a 10 year or, or more, a big, hairy audacious goals. So it’s part of your envisioned future.

It’s what you’re dreaming about for your company. So when you’re thinking 10 years in the future or beyond, and you can imagine what that looks like, set a goal that would live in the middle of that vision somewhere. And then you begin to start climbing the mountain toward the, toward the top, which is the Beehag.

Um, really all you need to know is how you’re going to get to that first base camp, which is what we think of is that three to five year plan. So if you’re thinking about winning moves in that timeframe, You don’t have to have all the winning moves. You don’t have to deploy every idea that comes to mind.

You just have to identify enough to support the growth plan [00:07:00] that you want to achieve in that timeframe. Does that make sense? Yeah. Makes complete sense. So tell us a little bit about the actual process and mechanics. Is it, you know, someone’s sitting in their room just thinking, oh my gosh, here are the best moves.

Like how do you really ideate and come up with solid moves? Yeah. So the truth is you probably have a hundred potential winning moves in your mind and in your company at any given time, everybody’s got ideas and opportunities are constantly coming. To you. So it’s really a matter of prioritizing what the right ones are for right now.

So the way that we like to do it, we think, um, you know, it’s not an individual usually. I mean, a lot of times, one idea will come from one person, then they’ll bring it to the team and then the company deploys the winning move, but the best ideas come when you get people in the room, when you get your executive team together [00:08:00] or your strategic, you know, um, team that you like to work with that you believe has a good grasp of what’s going on in the market, what your customers are looking for, what might work, uh, bring them together and do, first of all, just start with a brainstorming session.

What are all the potential ways we could increase revenue over the next three years? I mean, it could be opening new markets, it could be new products, it could be new brand promise. It could be, you know, any number of categories of things that it could be. But specifically for you, what are the ones that are on the tip of your tongue that, you know, are easy?

I put on the list and, you know, try to brainstorm 20 ways to increase revenue and then use that long-term plan that you have in place as a filter to kind of go through and see which ones seemed like the best fit for us. Uh, in addition to Beehag we also like to use this concept of the hedgehog, which is finding the intersection of these three circles with rigid dragged in diagram [00:09:00] of what are we passionate about?

What do we have the potential to be best in the world at and what will drive our economic engine? What will people pay us really well to do? If you can find those ideas that you answer positively, all three of those questions, that it would serve those and move you closer to your Beehag, then it’s a great candidate for winning move.

So that helps you narrow between. Yes, Chris, it’s a hedgehog because you can do this and it’s defensible. So you can basically poke your competitors. If you can identify the space, the zone, um, it almost sounds like an X factors or me or something unique and different that your company can do or, or how you can operate.

But can you just talk a little bit more about that? Like, you know, w why is it a hedgehog and what’s the, why is it so important to have this hedgehog idea in your business? I just feel like we’re going so fast. Sure. Oh, yeah. Sorry. [00:10:00] So, um, it’s a term that Jim Collins has coined, uh, about the hedgehog and he uses it.

There’s a fable and old fable that tells the story of the Fox and the hedgehog. And, um, there’s a bit of a competition between the two and the Fox is wily and crafty and chasing after all kinds of things. And the hedgehog just knows one or two, you know, it’s just focused on getting food that day and protecting itself.

Basically it knows what its strengths are and it knows what the core of its existence is. And so the hedgehog wins in this fable. So that’s why he uses that term. But in your business, it’s really under its understanding that core and the essence of who you are as a company and what is, what it is that’s unique about you that nobody else can replicate.

So that particular question, you know, what are we passionate. That usually is related to the purpose of your business, why you started the business in the first place. You don’t, you know, you’re not going to be hugely successful, doing things that you don’t really care [00:11:00] about. So you want to make sure that you’re working on strategies that help advance your purpose.

The question of what do we have the potential to be best in the world at that’s you. And that is unique to you and your company and your core competencies. So when you think about that, it’s not that maybe today you’re not the best in the world, but if you were to dedicate your resources and your time and your energy to this, you could be best in the world.

So understanding what the answer to that is. And then the economic engine is what is it that you’re going to do? That’s going to drive your business to be successful. That maybe is a little bit different way of thinking about it than the rest of the market. So when you combine the answers to those three questions, you get one small, tiny.

You know, piece of landscape that lives in the center of those three circles as they overlap and that’s the hedgehog. Wow. So I think it’s going to be interesting if we could play a game here just before we bring people on a game. I mean, [00:12:00] we’re talking about re doing this live is talking about startup club and you know, what’s our headshot, Michelle, and you know, what’s our winning moves.

So the next three to five years, but, but let’s get through the theory first and then get into fun. If you are in the audience, two things, one we’d love for you to share the room with your friends. If you think this is important for someone, just share it on clubhouse, you can see that at the very bottom of your app, you can click on that up arrow.

It’ll share it on clubhouse seconds. Uh, if you want to come on stage, this is all about community and talking and sharing. You might talk to us about your winning moves. Maybe you’re stuck on something, or you have a question for Chris. I mean, this is a great opportunity. To think about your business and the strategy for growth with your business.

So, Chris, you know, we’ve been through the exercise, so maybe you could tell us a little bit more about the mechanics. All right. So you said we have this group of people who [00:13:00] are all instrumental in the business, you know, all different parts of the business. It’s just not the CEO and whatever, the CFO, it’s all the functional groups and people that play a core role.

So like how do you facilitate capturing literally capturing all these ideas? And then if you could talk a little bit about how you map them and then, you know, whatever, you know, um, define it down to like 10 or three or how many. Yeah. So, uh, I mean, we, you know, we do facilitation a lot of ways. We do virtual facilitation and we do in person, uh, planning sessions with clients.

So we use different tools based on the setting that we’re in. But I mean, just old-school facilitation of brainstorming and having people share ideas, starting to capture with a list, um, letting people build on other people’s ideas and add [00:14:00] to them, just creating a really safe space for, um, letting people dream and think and be creative, uh, is the first thing.

So create that environment, find a way to capture the ideas and create a list of as many as you can come up with because the, again, a half-baked idea that’s thrown out there could be picked up by somebody else and turned into some, you know, piece of gold. So, um, just do it in a limitless way. Another, another, um, Tool that we use is de Bono’s six thinking hats where you would, you, you know, you put on the green hat and that’s the creative hat where you nobody’s allowed to say that won’t work because, um, you’re only allowed to say, okay, great.

Next idea. Okay. Great. Next idea. So it was green hat thinking, um, for this. So capture as many ideas as you can. And then what we would do is we would ask each people. So the reason I brought up the hedgehog was that that becomes a great filter for those ideas. You would be able to take each one of those [00:15:00] ideas and say, is this something we’re passionate about?

Does it line up with our purpose? Are we really the best at this? Can we make money doing it? And then that will help you narrow that list down to a manageable. Once you get it filtered through your strategic framework, which is the hedgehog. Then you want to look at it in more practical terms. What you’re looking for.

Again, if we’re looking for winning moves, we’re looking for those strategies that will help you double your revenue in the next three to five years. So you want to evaluate the ideas that are left on the board, the ones that make the short list, you want to evaluate them based on two things. One, what is the potential impact revenue impact of this idea?

Do we believe that this idea in itself could double our business? Do we believe it’s a $10 million idea, $20 million idea of $400,000 idea? What do we think the actual number is that we would assign to this? And on a scale of one to 10, we would, you know, the scale is different for every company, depending on [00:16:00] what size you are and what you’re striving to do in the next three to five years.

But on a scale of one to 10, what’s the potential impact on revenue. Then the second scale you want to use is what’s our ability to successfully execute. Is it easy or is it hard? Is it like, do we have the resources? Do we know how to do this? Do we know people who can help us do this? Have we had some success in this area already?

Is it going to help us accelerate some other ideas that we’re working on? If you have an idea that hits that all of those with a positive answer, then that’s a 10 on the ease. So you’re thinking in terms of impact and ease. And when you’re thinking about the ease, uh, line, you, you know, things that would make it difficult is if, if you don’t have the resources, you don’t know how to do it.

You’re going to have to hire a bunch of people. You’re going to have to do research and pull together, um, you know, expertise that you’ve never had before. Those would be that would score low on the ease rank. But once you have that. Um, think in terms of a quad with [00:17:00] the one scale of one to 10, going up, and one to 10 going across impact is going up, ease is going across, right.

Plot them on the chart and those items that fall in the top right-hand quadrant they’re high on impact and easy to do. And you already know that they align with your strategic vision for the company. Those are your winning moves. I think you’re trying to do something here that most startups don’t do.

You know, we, I think we like to fire, you know, aim, whatever shoot. I mean, we don’t, we always seem to get a backwards. Right. And what we’re saying here is, and when I talked about earlier, the wheels coming off the bus, you know, the reality is strategic planning can make a big difference. You can bring in, even if you’re a company of.

You can bring in, in a, in a group of people, they can help you with that. Uh, you can get involved in an incubator or a, um, uh, an innovation center. [00:18:00] Um, and a lot of those are free by the way. And you can work with a lot of people around you to help you build that strategy. So we want to identify a headshot like that.

I think we’re pretty cool with that. And we want to think about what are those three to five key winning moves. If you’re in the audience today and you want a question, this is it’s all about community or let’s. We want you on stage. Come on, raise your hand, get on stage. Don’t be shy. Chris’s new. We want to make her feel very welcome to clubhouse.

So she keeps coming on and giving us good advice. We’re very lucky today to have her on clubhouse and be spending the time she’s spending with us. So, uh, please feel free to raise your hand and no question is silly at all. Like we’re, we’re here to help, um, and get things moving forward. Uh, so let’s talk about.

Startup club. This is a club of about 850,000 people. And we have, you know, really we’re starting to get our Stryker, Michelle [00:19:00] and I add new spa, started it, uh, about a year and a half ago. And we took it over from him about six months ago, eight months ago. And now we’re, we really don’t have a strategy. And, you know, we talked about passion, the hedgehog, you know, I can tell you our passion, Michelle, and I think I can speak for you, Michelle, is that we really do love to help startups.

Um, and we do think that this particular platform of social audio chat lends itself well to building strong community, you know, and also, uh, can be very educational. We do 25 to 50 episodes a week on this, on this channel, on this club, the startup. So that’s sort of our headshot now. Now, how do we think about the winning moves for start-up club?

You know, are we talking about, do we want to set our goals first? Like, do we want to say, okay, we want to be tech. I was thinking of that before the show, you know, we really want to be 10 million members strong and I use the word strong [00:20:00] because they’re engaged right within 10 years and you really will be the global standard for education and art and startup the startup community.

So that’s where we have, let’s say that’s our Beehag right now. Um, so, and I, I know you’ve already sort of answered it, but how do we come up with these winning moves to get, you know, so we should be thinking about the next three years. Is that what you’re saying? We should be thinking about how do we get to that first base camp, right?

Yeah. So if your goal is to be at 10 million, uh, 2 million strong in 10 years, then where do you see yourself as you model that out in the next three years or even two years? You know, sometimes with. Um, the timeframe shrinks a little bit like 10 years is a long time if you’re in years of existence. So it’s okay.

Yeah. If you want to shrink that timeframe for your purposes, that’s fine. But maybe two years from now, where would you like to be? And what does that goal look like? And then based on where you are today, what’s the, what’s the Delta, what’s the gap [00:21:00] between those two and then Colin, I would say like you could do a S you could do, um, one of these sessions and engage your community in helping you brainstorm these ideas.

Like what are ways that we could get from wherever we are today to where we want to be two years from now in membership, and you will find, I’m sure there’s so many creative ideas just in the audience today, about how to help you do that. Um, so just a brainstorming session for that, how to gain more members.

And then once you have that long list start thinking about, well, which ones make the most sense for you? Um, you know, which ones do you already have connections that you could tap into or resources that you could, uh, engage to help you with this? And then think about, you know, which ones will have the biggest impact and which ones would have, so it doesn’t have to be a revenue number and your case members is equally valid as a revenue goal would be for this timeframe.

It’s just whatever is the number one target that you would use. That’s part of your vision in your case, it is membership, [00:22:00] um, or active strong members.

I think Michelle, I think active is key for us because we don’t, we’re thinking about, you know, how can we be the best, you know, community and educational environment for startups. So for us, it’s going beyond just the social audio chat. You know, one of those winning moves. Could it be setting up a VIP program that has access to, I dunno, 50 great books that are out there on how to scale your business, how to start your business and making those, you know, freely available to all our VIP members as an example.

Well, and maybe there’s a small fee for the VIP too, but we don’t want to, what we’re trying to avoid too is, you know, we don’t want to become the, you know, masterclass thousands of dollars to, you know, really hone your skills. There are some other clubs that do that. We’re trying to be sort of more of a, you know, ecosystem of generalists to help startups [00:23:00] just get off the ground to learn, you know, share their ideas, practice their pitches on clubhouse, that kind of stuff.

So is that one of the big winning moves is that potentially a winning move is to set up a VIP. I would think so. Yeah. A lot of times there are a couple of questions that we use frequently to help spark ideas. And one of them, one of those questions is, um, w do you have a diamond in your backyard? Right?

So the, the, the concept that we’re playing on is that there’s some asset that you already have, whether it’s a relationship or tangible asset, or, um, a system or process or something that you have in your company that you haven’t really recognized yet, or realize. So it’s kind of a diamond that’s hidden in your backyard, um, that you can access.

So for you, and I would think that relationships that you already have could, there could be a diamond. Yeah. In your backyard there. Um, another question that we ask is what is [00:24:00] it that customers hate about your business or your industry? What really frustrates people? They put up with it because they have to, for whatever the service or the benefit, um, that they get from your industry.

But you know that they hate it. If you can find a way to solve. That could be a winning move. One of the best examples I have ever seen is the Hyundai corporation back in 2008, right before the recession, um, people started become very, very timid about buying cars. They didn’t want to commit to, you know, a three-year or five-year financing deal because they didn’t have confidence that they would still be able to keep their jobs.

So Hyundai’s winning move at that time was a guarantee, a promise that if you lost your job during the time of your financing, that you could return the car, no problem, the questions and that just completely accelerated everything for them. So, you know, that was the fee. That was what was holding people back and they found a way to overcome that.

And that [00:25:00] was a winning move. You know, I think about, um, national car rental and they know they did just walk up to any car, take it up a lot. So you didn’t have to line up for 30 minutes, you know, after an exhausting flight, I think about Domino’s 30 minutes. You know, I mean, coming up with these winning moves, they must’ve been pretty scary.

I think about Hostopia the company that I ran that was public in the two thousands and, you know, our winning move there, the one that really killed it, and that would actually became our X factor was that we sold directly to a buyer, you know, a person within those telecoms who was afraid of losing their job.

And we came up with the idea of a hundred percent migration guarantee for websites and email. And if you know anything about it, when you say the word migration, everybody runs, nobody wants to be a part of anything to do with the migration because they’ll lose their job. And, uh, it just totally changed our organization.

We had to re-engineer our entire [00:26:00] organization around this. Cause we don’t, we didn’t just say a hundred percent migration guarantee. We actually paid fair market value for every website that was lost in a migration. And we moved over websites from birth, like 80,000 at and T Vodafone, British telecom. I mean, we were working with some of the largest companies in the world and we won almost every contract.

It was like dominoes going down and we just, it was just amazing how it happened. And I think about, um, national car rental, and I think about Domino’s pizza and how at the time, when they came up with these winning moves, the competitors would say this, oh, it’s impossible. And we actually owned a pizza restaurant when I was 17, 18 years old, or family owned one, we said, oh, it’s impossible.

We had this company called pizza pizza up in Toronto. And they were like the Domino’s. And they said, they’re going to do 30 minutes are free. And we said, oh, they’re going to go bankrupt. Everybody said that. Yeah. And you know, I think the best winning moves [00:27:00] can have that effect on a company that they not only.

Open up the market significantly for you. They drive internal processes and excellence in a way that like foolproof your business. Like, just think of all the changes, like the things that you put in place at Hostopia to make sure that you had a hundred percent migration so that you didn’t have to default to the promise, that would be painful for you.

If you had to have you had to pay out on that. Another great example is Michigan. I call it gut wrenching. It’s like, if it doesn’t really hurt your stomach, that it’s not, you’re not going far enough, right? Yes. Yeah. And you know, so that’s a great example of winning moves. Another one that we have, um, a company that we worked with, it’s a specialty pharmacy company and they had just a wonderful, uh, Network that they were working within the organizations between the pharmacists and the doctors and the patients.

And one of the biggest things that [00:28:00] patients like, the biggest problems it was problem for the patient. And the doctors was that it would take two weeks to get approval. From the time a doctor would prescribe a medicine to the insurance saying, yes, we’ll pay for it because these are very expensive specialty pharmacy, um, things that they’re working with.

And so the insurance companies were a big bottleneck in that case and they determined that they were going to take that two week timeframe down to two days. I mean, I’m sorry, two hours. Eventually they got it down to a two hour guarantee, um, that they could get the approval. And it took like they just made massive breakthroughs in what was bottle-necking that system one after the next, after the next and changed the whole industry because of that.

But because they were able to do that, every single doctor wanted to use them. So there’s where the, the ones that they would record.

But not only that it made them better, what they do. It’s amazing. Right. Because I’m sure [00:29:00] everybody was like, it’s impossible. You don’t have to get all these insurance approvals. I I’m guessing. Right. They’re like very expensive farm, you know, pharmacy kind of operations. And they just took that and dissected it right.

And made it happen. And like you said, this stuff, doesn’t, it’s not overnight. And obviously you have to make sure you can do it and that it will have a very positive economic outturn. So I think that’s a great example, but, you know, we found even in our companies, they don’t have to always be that grant as well.

In the beginning of. Especially if you’re in a new, you know, a new kind of industry or whatnot, little things too, right. Can be winning moves. We, we often times like find little winning moves that really just change, you know, the trajectory of the company. Yes. Yeah. And that, so w [00:30:00] as you do this exercise to try to brainstorm the ideas, filter them through the strategy and then prioritize them through the ranking of impact and ease.

That’ll narrow it down to a couple of ideas, but you’re probably still going to have more ideas than you do resources to execute. So it’s, it’s helpful to think, you know, if you have a couple. Um, ideas that are 10 tens right there, they have a 10 impact and a 10 on ease. Like that’s something you could do two or three of those at the same time, because of the ease factor, because you have the resources and everything you need to do that.

So those are wonderful, but more likely what’s going to happen is you might have one in that top quadrant and you might have one left top quadrant, which is going to say that it has a huge potential, but it’s going to be very difficult. So in that case, if that’s the one that you want to go with, because you believe that impact is.

Promising then you really need to eliminate the other ideas [00:31:00] for the time being. You have to measure balance your ability, your resources, to how much you’re trying to do. And so rather than going and firing a whole bunch of bullets in a whole bunch of directions on all of these winning moves, it’s, it’s picking the one or two, maybe three, depending on your resources that you want to go master right now.

And the beautiful thing about this is that you’re only thinking in a short timeframe. So 2, 3, 4 years, um, we’re going to be focused on these one or two things and we’re going to master them, but we know that we have these other ideas and the eye on the, we call it the idea of. That we’re going to pull into play as soon as we get those kind of, um, built into the core of our business.

So we’re going to execute on initiating these winning moves first. And then we know as soon as we’ve digested that we’re going to put these next ones into play. So you have this continuous funnel of ideas and opportunities for growth going forward. You got to get all the way up that 10 year mountain that you’re [00:32:00] climbing, but you plot your way up there all in one day, you’ve got to be able, you just have to get to that next base camp and then reevaluate and say, all right, what’s next?

A lot of focus, a lot of seller execution. So, you know, let’s just reset the room real quickly. Here we are on serial entrepreneur club, which is on startup club, the largest club on club house. Um, we’re getting a lot of really great tips and information. We will be writing a blog post on what Chris is saying on, on the quadrant.

If you’ve missed any of those key components, we’re going to lay it out really nicely for you. So be sure to visit and also join the email list. Um, we only send out emails when it’s meaningful, um, you know, special speakers or content that we’re putting out. And in fact, I’m [00:33:00] thinking.

You know, you’re giving us some really good tools here, Chris. Um, we could do an email to share with all the club members here. Um, the information that you’re you’re dispensing for us. So be sure to go to and sign up for the email list. So correct. I want to read something that actually stood out for me, as we were planning the session, I happened to see something that Elon Musk said, okay, what his advice was, this is a, you know, a business, you know, blog.

I follow, he was quoted as saying, stop being patient and start asking yourself, how do I accomplish my ten-year plan? That’s what you said, your tenure mountain in six months, he says in six months, right? Ilan is aggressive, right? He says, you might fail. You might fail, but you’ll be a lot further along than the person who never took those [00:34:00] steps.

So, you know, it’s easy. I think for people, executives, personal life, business, life, whatever it is to sit around and throw out lots of great ideas. It’s another thing. To really try to evaluate them and pick the top three that’s, that’s actually hard, right? Like that’s a quality problem, but it’s actually hard when you feel like there’s a lot of opportunity.

That’s where, you know, this framework you’re talking about, I think really helps, helps people out for me personally, on some of my businesses, I I’ll make them like a year, honestly, because it’s kind of like, um, get going or die on the vine and, you know, we don’t want to die on the vine. So, um, be sure to, you know, follow the blog.

You’re going to get more detailed steps, but I just saw a bunch of folks just pop up on the stage. Thank you for raising your hand. Um, we want to start with your questions, [00:35:00] so please bring up your questions, um, for Chris. Um, please keep it to the point and we will do our best to help you. So let’s start first with Kepler K.

What is your question for Chris?

Um, I guess so my question is how do we collapse timeframe from the ten-year plan? So let’s say a quarter. Yeah, that’s a great, great question. We, so our overarching methodology is really simple. It’s think plan do, and it’s strategic thinking, which is what we’re talking about right now. And then execution plan.

And then doing the work. And so that, that think piece of it is anywhere from two years to 10 years, to further out that’s the long-term strategy planning. We [00:36:00] usually recommend you do annual planning and quarterly planning. And so, you know, what your winning moves are. If you’ve done your S your strategy session, you have an idea of what you want to execute on.

You want to think in terms of the next 12 months in this year, what is it that we want to accomplish related to that winning move? Where should we be by the end of December? And then you put that into quarterly execution plans. We do, we like to do a four quarter flyover, um, which is an exercise where we think in terms of major milestones for each of the four quarters in that year.

So if we’re going to be here by the end of December 31st, then where do we need to be the quarter before that, the quarter before that? And then what does that mean? We need to do this quarter, then you build your execution plan, and that should be very detailed. It should be. You know, who is the owner for each of the initiatives?

Um, what are the priorities that each person will be focused on? We use a red, yellow, green success criteria that says by the end of this quarter, success will look like this. So [00:37:00] always begin with the end in mind and describe what success looks like. And then. We set up what we call a 13 week race. And so each quarter is made up of 13 weeks and we have a way of status in progress on each of the priorities, supporting that winning move in that quarter, every single week, you’ll be able to visually see, is it red, yellow, or green?

Are we on track? Are we off track? Are we having a big problem? And the beauty of that is that the earlier in the quarter that you start to see red and everybody sees, everybody gets red at some point, um, on some of the strategies, things never go exactly as you planned, but the earlier you had that information, the sooner you can start addressing it and making adjustments and finding breakthroughs to get it back to green by the end of the quarter.

So it’s really that we call it a rhythm of work. That is the strategic thinking, annual planning, quarterly execution planning, and then running that 13 weeks. [00:38:00] Wow. That’s that’s impressive. So it’s not just float down a river and see what is thrown at it. It really is a process. It really is a system to help startups entrepreneurs.

And let’s be, let’s be quite Frank. I was like that in 2006. When, when, you know, we just sort of went at it, we managed to go public. I don’t even know how we did that to be quite Frank. And yet, yet here we are, the wheels are coming off the bus. And then we decided to bring in a professional coach and be able to, to bring in these systems and figure out our winning moves and then figure out our goal setting and have an annual goal, quarterly goal, individual goals.

I think the individual goal setting was probably one of the most important things that we had in our organization as well. And, uh, it’s interesting that we as entrepreneurs, we’re all type a, we’re all like, we’re look, we’re all over the map, you know, we’re, we’re not, you wouldn’t think half of us would make them the success that we do.

You know, just based on our [00:39:00] personality types, but these systems work, they make a big difference and, uh, really appreciate you sharing them with us. Um, Keppra, does that sort of address your question? I mean, you go on from 10 years, like we have 10 million members on startup club, 10 years from now. So in our next three years, we want to get to 3 million.

By the end of this year, we want to get to a million. I know we’re at 850,000 now, so we’re at least beginning to say, okay, this is what we do, but what are our winning moves to achieve that? You know, what are we actually going to do? We talked about maybe a VIP membership, you know, um, we talked about a book club, you know, we talked about other things that we could do to really add a lot of value to the members, to improve engagement and also, uh, increase the membership.

But any thoughts, capital writing at any additional thoughts? Uh, not really. Cause I was early today. I was writing down the plan for how we’re going to acquire customers and things like that. So I just kind of wanted to [00:40:00] see, I do like the 13 week plan. So I’m going to be implementing that in seeing and putting in these like steps where we’re supposed to be at each, uh, each week.

So thank you so much for that. Yeah. And I think, you know, being able, um, I’m going to, you know, project a little bit, I don’t sounds like it’s like business development or sales, is that right? Uh, so we’re going to, so we want to do marketing and sales, marketing and sales. Yeah. So one thing I have found running those types of teams is if you really can break it down for them, you’ll be a lot more successful because the tendency is for people to procrastinate a and then B.

Um, you know, have a hard time breaking down how to get to that goal. So for example, if you literally can say each person, [00:41:00] let’s just talk about sales for a second needs to have a making this up. Okay. You know, 10 qualified leads, let’s just say a week and convert, you know, let’s just say 20% you could back into saying to get those 10 qualified leads.

We know that we need, you know, a hundred outreaches and if you get the whole company, right. So that’s their goal and their accounting to that Kepler every single week. And then marketing, for example, if their responsibility is to feed the 200 qualified leads, You know, you can see how the company can really start to come in alignment because then whomever is managing, you know, the process or the people, actually, all those areas, [00:42:00] their responsibility then, because they’re also buying into it.

The whole company’s buying into it. And the whole company has to be tracking to it. And in fact, what I would say to my team, and I did say to my team is if you’re working on anything else that is not here, then you need to come and talk to me right now because we have an issue, right. Because that’s, what’s going to cause you to go off, off the rails.

Now, now maybe you think you’re doing everything right. Right. And you’re not accomplishing. You know, let’s just say, I’m getting analytical here. I’m a little analytical. If you don’t do those two sales a week and you think you’re doing everything well, that’s what Chris is saying. That is critical information for you as a sales leader, because then you know it very quickly and you go, okay, something is not working and you can try to fix the [00:43:00] problem very quickly.

And for me, honestly, over 50% of this whole process, It’s like being able to have that transparency and that insight, like people cannot hide behind their desk or hide behind their couch or whatever, if they’re at home, like, you know, there’s accountability here and they’re buying into the goals and they’re help setting the goals.

There’s like, no ambiguity now, you know, of course, like Chris said, and we all know this, like in a perfect world, we would just do this and everything’s perfect. And oh my gosh, we’re like mega successful, but I think, you know, again, it’s really helps you correct. And just figure it out and just continue to just, just drill down and figure out what’s working and where there’s uncovered opportunities.

Yep. And having those places in your flight path that are going to show you when something goes off track really early. Th those early warning signs are huge [00:44:00] and being, having the mechanisms in place to bring the team together to solve those problems and make adjustments early in the quarter, as soon as, you know, you have a problem.

Yeah. One thing that I really love that I think, um, that you guys talked about at the conferences, you know, these are weekly meetings, right? Kepler, um, you know, people are pronounced Kibler. All right. My apologies. Um, yeah, it’s not a meeting where you’re like, you know, a lot of meetings like this. Like people like to sit there and go, okay, I did my 10, you know, I’m done, you know, you know, that’s great and that’s awesome.

And people should be, you know, commended for that and celebrate it. But also is creating this environment where if you’re struggling or the company’s struggling or they’re waiting for somebody that everybody’s really comfortable. About stepping up and saying it so [00:45:00] that it can be addressed.

Uh, actually it was just this week I hit a, uh, something that wasn’t supposed to happen. We have a product problem. So that was annoying. It kind of destroyed the timeframe too. So that was fun. Yeah. And you know, I’m going to guess, I don’t know your product or your system and you know, all companies suffer from this, you know, a lot of times these things are not brought out work through earlier, just because of this communication.

But if you have this framework, that’s very structured, you know, it, it, it really, it helps submit a gate. Let’s just put it that way. Yeah. Our motto is focus, alignment and accountability. I mean, that’s what we’re looking for in everything that we do. And that’s what really lends itself to, uh, increase the execution.


Yeah, I think we got Michelle’s, uh, your modernist here, but I’ll show season up next to them. You Ron. Hey Ron. Nice to see you again, by the way. Thanks for coming on state. We’re probably just pronouncing your name wrong, right? Cause we did it with Keebler shows. Is that yeah. Hello? Yeah. Yeah. Is there a question for Chris please?

Yeah. Uh, I am from India. Okay. Um, I have started his chart that, uh, can help people to perform automatic. You do a seal. Okay. But, uh, uh, I don’t know what to do next. And I have created this one.

So you, you have a product that’s out there right now. Are you having some success with it? [00:47:00] What are you having success with your current product? And you’re trying to think of what’s next. The question is what, what else should you do? Yeah, I, I, how I, how duster the product and it is working. Absolutely.

And I will get the product into market. Do you, is this a new business? Yeah, a new one. I just don’t my me and my friend created the product and it is a, the world’s first software that we have. Yeah. A lot of times we find that with a startup. Um, you like the idea that sparked the birth of your company is your winning move.

You are executing on your very first winning move just by starting the. So stay very focused on the original idea at this point in time and try to maximize whatever you think the potential is for that idea. And if you know, if you’re stuck on, you’ve got [00:48:00] a great product, you’ve got a great idea. You aren’t able to sell it just yet.

You haven’t figured out the magic of, um, you know, how to convince people to buy your product. Then probably I would recommend that you do some work on trying to understand your core customer, who is the one you’ve designed this for. Uh, what are the attributes of that person? What are their hopes? What are their fears?

What are they, uh, striving to accomplish personally? And how can you relate your product to that success, uh, to their success. And then, um, identifying your core customer and then working on the brand promise, what is the messaging? If you feel like your product is solid and there is a place for it in the market, then it’s really about addressing the customer and finding out how to convince them of what you need.

You already know. I would also add that. If you build it, they won’t come. I built a number of platforms in my time and you know, once you built it once you’ve got something there, that’s really cool. It’s neat. We need to now [00:49:00] find a way to distribute it. We need to have a distribution strategy. So one of our winning moves are in this area would be distribution.

Maybe it’s a Shopify plugin that you can get on the Shopify store. Maybe it’s, um, you know, something that, uh, can connect with MSPs managed service providers, um, or those who offer, you know, Google ad-words or, you know, so if you can find, uh, you know, you’ve got the product, you’ve got the MVP, but now what we want to do is we really want to find a way to sell it.

And, and that can be very tricky. And there’s a lot of throw a lot of spaghetti on the wall and figure that out, to see what sticks and then, you know, really invest your dollars and your time and energy in.

Yeah. Uh, but, uh, what I have done with my software is, uh, that, uh, this is a SAS software, like a software [00:50:00] as a service. And in this software, I have made it a free, uh, for a plan, like three free hour. And in that plan, everyone can come and use the app for free. And this is a customer acquisition model. And also we have a affiliation scheme, like a reference scheme where, uh, people can get a 15 to 30% age of a monthly recurring revenue for lifetime.

No, I, I love the free, the free strategy. Um, it, it, it, it can be difficult to sustain, but I would encourage you to think about distribution as in setting up or working or ideating, figuring out a winning move around, distribute. This has been great shows the rod you’ve been patient. Thank you for coming back.

And one of our favorite guests. Oh, bless you. Patient. I am not. I’m the eager beaver of the world. [00:51:00] Uh, thank you though. I have a question for Michelle. Um, I’m uh, for those that don’t know me, I’m a serial entrepreneur. I’ve had a half dozen companies that tend to grow like three-fold per year compounded 1, 3, 9, 27, that kind of growth.

They do not tend to involve struggle and barriers and setbacks and hard work. They’re all based on radical venture strategy. They all break the rules big time. And as I listened to you, Michelle, it sounded like you’re very expert. At problem-solving and getting things done, getting, you know, fulfilling a plan that exists.

And I was very curious to ask you, if you just sort of put on another hat here for him [00:52:00] for a minute, Michelle, how do you go about discovering new opportunities? Not problem-solving with old issues and barriers, but discovering big new breakthrough opportunities. What’s your approach to that? Yeah, that’s a great question.

Right. And I know you’re an expert at that, Ron. So for me, it’s. I find if I just like set by myself and think it doesn’t always go so well, very also kind of social person. I need to be out talking a lot of people, experiencing things, reading, um, it, you know, that’s just my style. That’s the way it tends to be just looking for, you know, pain points and seeing what other people are doing and listening to people.

So you, you use interpersonal collaboration with one or more [00:53:00] other people to have these big breakthrough opportunities appear. Yeah. That that’s typically how it works for me. I get crazy ideas, but you know, I, and I believe in my ideas, but I, I also really do like to talk to people in my, you know, usually first in my trusted circle to help me like.

You know, a lot of times, right? Like people get ideas and they personalize it. I try to not personalize it and really, you know, talk to people that I respect and considered to be. Forward-thinking I know one thing we do, Ron, is we set up like a strategic planning session. We do an offsite. I often do it at one of my homes, whether they’re a beach house or up north in Canada.

And, um, you know, we set up these environments for two days where they’re relaxing and you know, we come up with ideation. We sometimes, sometimes we’ll do Chris. I don’t know if you’ve done this [00:54:00] where, um, we actually say to people, we don’t want group things. So we’re going to break everybody into two people per team.

And you’re going to go for a walk, come back in 15 minutes. And each of you could come back with 10 different ideas or five different ideas of how we can make this winning move happen or whatever it is. Any thoughts about what Ron’s talking about? Yeah, I love that idea of there’s so many different ways that you can facilitate these types of sessions and break people up and create creative environments for, for creating ideas.

Um, but you know, research shows that there’s a different area of your brain that engages when you verbalize the problem, or you start to speak about what it is that you’re trying to solve for. Um, so this idea of like noodling it around in your head for long periods of time, you can only get so far with that and you may be able to solve it yourself.

But once you get in a room with other people and start speaking it out loud, it engages a different part of your brain and it engages all of the other brains too. [00:55:00] So then we say the more brains in the room, the better your chance of being able to come up with a great idea. The other thing is that. You know, I think not to think that it has to be one Eureka moment.

These ideas usually come, they may seem like an overnight success, but it’s, it’s time that you spend in, um, letting the idea evolve and coming, you know, as best version of itself. So don’t feel like you don’t always get it in one, you know, two day offsite, you may get the spark or the inspiration that really starts to crystallize over the next couple of weeks or months, or, or maybe it’s several inventions and they all come together in one big thing.

Yeah. And you know, another thing that I think can really help spark ideas is to look outside the industry you’re in, that’s one of the things that, you know, are you calling him Michelle? You’re talking about our conference. We are, um, [00:56:00] across all industries, we have people from, you know, everything that you can imagine, manufacturing service it.

Um, Bio pharmacy company. I mean, it’s everything that you can imagine. And, um, the ideas that that are shared that are working for one person can help solve a problem in a wholly different way, uh, for a different person. Yeah. I also say, look internally, like, look at your own staff. But one thing is startups as entrepreneurs, we tend to be type a, we tend to think our ideas the best, but I’m telling you this every time I’ve done a strap planning session, we bring the entire, we bring the, the S the, the executive team together.

Generally, if it’s a small business, everybody, uh, we get such phenomenal ideas from the places you would expect them to least, uh, there is. So we always get those aha moments or those strap planning sessions. So I say like, there’s no idea. That’s like, it doesn’t matter who creates the idea in your organization.

At any idea can be good. [00:57:00] And we just want all the ideas to flow and then a capture and figure out which ones are the best ones we need to adopt. And for some reason, we’ve just had a lot of success at these strap planning sessions. I’m finding that it isn’t even that what you’re saying is so true that it even applies outside of business, that maybe you’re watching a movie or reading a book or walking in nature or playing with your pet.

And that triggers some big idea. In other words, you’re utterly out of the realm where you’re, where you’re having the desire to have a professional uh pithany but it comes from somewhere else by metaphor. Very true. Yeah. I love that, Ron. I mean, I have a personal rule, you know, when I’m going, having difficult decisions, good or bad.

Or just need to really come up with something I [00:58:00] really liked to say, I need to sleep on it. I mean, there really is something to that. You’re absolutely right. Just like freeing your mind. Do you, do you wake up with big ideas that come to you in your sleep? I, I do quite oftentimes like literally wow. Me too.

Yeah. And so it’s really phenomenal, right? That the human mind can do that. I would rate it as my greatest pleasure in my greatest burden, because waking up in the middle of the night with a giant idea and, you know, going to my desk and writing it down before it’s lost is so much fun. But on the other hand, it’s keeping me up and costing me sleep and, and then it gets so excited.

I can’t get back to sleep again.

I love that. Thank you.

All right. So we’re going to keep moving on. I know we’re running a little bit late here. We have two more people on stage. I don’t know, ed, if you have a question I [00:59:00] just invited you out. There are. I told Ron he was one of her favorite. You are as well and as well, so, but I J Jesse real, is that how you pronounce your name?

And do you have a question for Chris or anyone on the panel or a thought about winning mus, Jesse reel the mute button down in the right corner. If you’re new to clubhouse, uh, Edna any, I know you came in really late and, uh, just like a pop on, on underneath there. We’ve been talking about strategic planning, winning moves, how, how you do.

You’re very successful entrepreneur. You’re very successful at startup club and everything you’ve touched seems to be success. Do you do strategic planning? Do you spend time thinking about winning. Absolutely. There’s a saying in Spanish Nika that a bustle seawater. Which means that you don’t, you don’t make a move without barefoot.

Right. You know, we’re, uh, a what aren’t you, which is like a [01:00:00] slipper and I pretty much will think things through and I will also have possible outcome scenarios and what ifs drawn out and what if this, then that, what if that, then this kind of thing. And, um, so when it does happen and things get a little sticky or things, you know, go out of hand, I already have the resources in place because I thought it through and, you know, um, every now and then I get a surprise where I was like, whoa, I didn’t see that coming.

And then you just go back and that forces you to create another, you know, another, uh, soap note, and then you just start adding to it. And before, you know, it you’ve perfected a lot of systems that will keep you from having, you know, those, those scenarios where you’re either. Without product or without, you know, the right people or licensing or permitting.

And, and so, yeah, but it takes a while. I mean, when you first start out in something, if you don’t do your due diligence and you don’t have, you [01:01:00] don’t do your homework. I mean, you’re going to hit a brick wall, really? This isn’t the worst thing. When you see a startup or any company, any business, they make the same mistake over and over again.

Like how many times do you have to make the same mistake before you realize, Hey, I should set up a process. So this doesn’t happen. Exactly. And so here’s the thing. If you’re, if you’re just banging yourself up against the wall, you’re losing time and momentum and, and what you’re doing is you’re setting the pace for the people that are coming behind you that, you know, Hey, it’s okay.

If you hit the brick wall, just keep hitting it. And eventually you’ll break through no, you know, take a step back, look at where you are and then figure out a better way. I always say that, give the, give the toughest tasks, the laziest people, because they’re going to find the easiest way to get it done.

And then they’re going to come back with a solution with a solution. And it’s the path of least resistance. Sometimes it works, sometimes it doesn’t, but you know, you’ve got, when you run into an issue or a problem or situation, a, uh, it’s extremely important that you write it down and create a, [01:02:00] uh, standard operating procedure to avoid that from happening again, and then train everybody that’s in that department.

So they know we’re making changes and that’s the thing of a business. You know, you have to constantly be changing and evolving to make things. Oh, I w I wonder if we could address another topic. There’s an awful lot of brain power here. I know, I know Ron, but we are at a time and I just wanted to see if Chris could share any final thoughts.

Um, we do have the topic then for the future. I love the idea, plant the topic, and then maybe we run a show on it, but you gotta promise me you’ll come and help me lead the show. All right, I’d be delighted. Hey, here’s the topic? What are the most devastating killers of a startup? What are the absolute lead devastating things to not do?

I love it, love it. We’re going to run a show on that and Ron, and you’re going to help us [01:03:00] moderate it. Okay. You’re on the clock for that. You’ve agreed that this is being recorded. Okay, rod, I love the topic. We’re going to do it, Chris. Any final thoughts before we close out? Uh, yeah, I just want to echo what ed was saying about, um, in talking about contingency planning and plan these, uh, in the event, when something goes wrong, you know what to do.

Um, what we really recommend is that once you’ve identified the winning moves, you want to activate, you need to test your assumptions for each one of those winning moves. You, you gave it a ranking of what you think the potential impact is somewhere between one and 10, and you base that on some assump assumptions.

So before you go full force into execution mode, take a little bit of time and test those assumptions to make sure that what you thought in your planning session as you rank, those is actually proving out to be true. Um, sometimes there’s some mild adjustments that need to be made along the way with those.

No, that’s great. And thank you [01:04:00] again, Chris. I mean, look, we have an expert in the audience here, a future clubhouse celebrity, like ed Enron, Chris Cosper, coming on like this, this. That you’ve spent the hour with us invested the hour or the time with us. And we learned so much. And even again, I always take, I always take one or two good ideas from these sessions and we really do appreciate it.

And I knew you’d be an all-star. And if, if you’re not already following Chris, please do I’m following her. I’m following, uh, Ron, I’m following Edna. I’m following Keebler on both you Daleville. We got your name, right. And Jesse real I’m following you. Even though we didn’t get to hear from you, like put too bad, but we are, we are closing the show out right now.

Next week, we are running a show on tokenizing real estate. We’re going to work on Ron’s show about what not to do, what as a startup, the absolute things you should not do as a startup. We’re going to run. We’re going to run Ron show in a, in a few weeks. I think we’re booked. So we’ll have to be sometime in June Ron [01:05:00] to get that on the docket, but I sent you a text, you know, we just need to get some information from you to help help with that.

That being said next week, we are running the show on tokenizing real estate. Uh, wow. What a concept. I mean, we’ve seen crypto crash and all this, but what we’re talking about is something a little bit different. These are hard assets. These are not alternative to read. This is a way that entrepreneurs or real estate entrepreneurs can actually raise money using tokens.

And we’re talking about doing this with the right sec regulation. So we have a lawyer attending the session, a specialist, someone who runs her own show here every Wednesday, I’ve joined her, uh, every Wednesday at seven o’clock. She runs a show on, on, uh, on, on, on the legality of raising money and we’re bringing her in and we’re bringing a 24 year old MBA.

Who’s working for a $2 billion company. Real estate company and they’re tokenizing a Miami condo in [01:06:00] Wynwood. Very cool. It’s an alternative way. It’s it’s, it’s opened my mind up in our real estate business that we run here. Um, escape club, which is a vacation rental businesses totally opened my mind up to alternative ways to raising money.

So that’s something that’s happening next Friday at two o’clock. And by the way, I knew that because I went to and I actually had to go look at the calendar, see what’s what’s going on next week. Let me see, you know, cause I want to put in a plug, you know, if you’re on the podcast or whatever, to check out that show, if you’re interested in that topic, please go there.

If you’re interested in learning about more topics and more shows, go to, by the way, if you’re interested in becoming a leader and you want to run your own show, please reach out to us as well. We have a lot of, uh, we have about 60 leaders who are on startup club and we’re we’re we’re we’re we believe that’s key to hitting our million members this year, 3 million in two years, 10 million in 10 years with our Beehag.

Thank you very much. And what a great show appreciate. Have a wonderful day. Thanks everyone. Thanks Chris. [01:07:00] Thank you. I had fun. Bye. You too. Bye-bye thanks y’all and if you haven’t already done so click on the little greenhouse up at the top, follow the club, or go to the website, and register so that you can be in the know and get the emails of all the exciting stuff that’s happening at startup club.

That’s so much better than I do. You’re really. I miss you. And you got to get you to run a show. You got to do a weekly show on getting unstuck on start-up club. I’m telling you you’re the best, uh, w I sent to a back channel and I said, yeah, let’s do a weekly show either. We can do green startups, solar in America, or just getting unstuck in your business and business strategies.

Those were, those were really successful. All right. Sounds good. Well we’ll and make that happen by.[01:08:00] 


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