Things to Know When You Create Content | David Ledgerwood

Things to Know When You Create Content

with David Ledgerwood


About today’s guest:

My guest today is David Ledgerwood, an expert in sales. He has helped hundreds of companies grow from hundreds of 1000s of dollars in revenue to millions in revenue and 10s of millions of revenue. We talk about a lot in this conversation. A few things to listen for; one is the discernment between being too narrow and too niched in versus being too broad. I enjoyed our conversation around this. A second one was around how things don’t necessarily need to scale at the start of an organization. Yes, we’ve all read the lean startup. We all know about the importance of scalability. But that doesn’t always mean you need to start there. We talk about how sales can inform marketing, and I loved David’s thoughts on specific tactics on how to do that.

As always, May I Have Your Attention is brought to you by, which turns your podcast into three months of social media content, you can find out more at

Time Stamps:

  • David’s background [0:41]

  • When to stay myopically focused on one type of customer [5:51]

  • Focus on service businesses [9:23]

  • How a sales should be informing marketing [14:38]

  • Trends that stand out [19:16]

  • Companies publicly displaying pricing vs. being opaque [23:38]

  • David’s tips for startup founders [26:03]

Selected resources:


Justin Nassiri  00:03

Well, all right. Joining me today in Nashville, Tennessee, my guest is David ledge, also known as ledge. Welcome to me, I have your attention. It’s good to be here. Thanks for Justin. So want to give listeners a quick background lead is the co founder and managing partner at ad one zero, where their team provides lead to close sales execution for tech enabled b2b services, companies ready to leap from six to seven digits of revenue. He’s a 13 time founder with over $40 million of software and service sales in the last decade. He’s been a sales leader since 2007, and has taken multiple companies from bootstrapped to millions in revenue. So let’s maybe to kick things off. How would you explain to someone if you ran into them on the street? What you do at ad one, zero?


David Ledgerwood  00:57

Yeah, I was just listening to you say that. It’s a mouthful, right? And, you know, and I, it’s interesting, right? The conventional wisdom about your elevator pitch should be like fewer words and sort of make it really easy. And all those things. And I always did that. And then I realized that niching to an extreme level is, is critically important. And you know, we try to explain what we do in a simple way. But less important than being simple is appealing exactly to the person that that we want to deal with, right. And so we are looking for founders of b2b services, companies, typically I say, tech enabled, because that is sort of, you know, you run your business on SAS, you’re familiar with remote work even before COVID, you know, sort of all that stuff. And what we do is we look for founders who have these, you know, b2b services, companies, maybe that’s marketing or some kind of niche service, professional service, things like that. And I have found in my, my journey that those people can bootstrap and take their companies kind of to like that half million kind of mark, where they reach this point where they say, Do I want to grow up and run sales for this company? Or do I want to grow up and run the company and be a CEO? And there’s no right or wrong answer there. There’s very successful CEOs who are on the sell side, and they know I gotta hire an operator. On the other side, if you want to be an operator, then you know, you got to hire someone to take over and grow and run sales, the available options to do that, but it’d be well let me hire sort of young and hungry SDR, you know, straight out of college, and we’ll throw them on the phone, or I’ll hire a lead gen service, or I’ll do this or do that and or VP of sales. Let’s spend lots of money on that. And I found that neither none of those were really a perfect answer for that, that type of company at that, that point, you ought to do a lot of those things when you’re up in the middle millions type of range Sue, who was going to help from that, that six digit to seven digit, you know, how do I take a company that I got off the ground, got to about a half million, I’m feeling good. But the next step next is a totally different business. And so those are the people we work with, if you are a founder, and you don’t want to sit in that seat anymore, I’m done with sales, I never set out to do sales, I want to do the thing, I want to run a company, I want to grow my staff, it’s probably not affordable for you right there to hire a sales leader unless they’re, you know, a partner kind of in your company and working for for equity. And that’s, that’s a difficult thing to bring people onto. There’s a lot of trust involved in partnerships. So we slide right in there. And that’s what we do. And we’re going to come in and we will be your white label closers as a service, your whole sales and revenue, you know, department division, call it what you want, revenue operations, everything from the point at which you get a lead into that business, they want to do a call with somebody, we will take and do those calls. And it look just like you, it’ll be part of your company. We run it all the way through the deal pipeline, all the follow ups, all the paperwork, all the things that you need to do to turn that into a customer and then hand it off to your your customer success and ops. And that’s the revenue function. And that’s, that’s, you know, sort of what we build and we’re really good at at scaling businesses that way.


Justin Nassiri  04:24

So a couple questions come out of this for me, one of them is, I like what you were saying about how, you know, it seems like as an entrepreneur, you’ve seen the power of niching down on on a really narrow thing to focus on. How have you, you know, as you’ve grown your company, as you’ve grown multiple companies, how have you known when to stay myopically focused on one type of customer versus like, you know, as you’re building a company, there’s other opportunities and so there’s always the temperature, that temptation to widen the aperture or to chase more or to do more. Just kind of curious have you built that discernment of when to stay myopically focused versus when to broaden and trying to expand more?


David Ledgerwood  05:09

Yeah, you know, look for founders, right, we all have sort of the squirrel, you know, sort of, you know, hypothetical add or whatever. And we love being new. I love big new ideas. I mean, I’d rather go do something new, every day. So I mean, how did I grow that muscle by doing it poorly, you know, lots of times, right? Eventually, you learn that you need to do this. There’s always gonna be that next thing, and I think one of my guests on our podcast, you know, told me this that the way I think I asked the same question, and that it really comes down to having a mission, your vision of the company and a set of values that will help you say, is this or is this not directly driving to myself, in my clients toward that vision. So for us, you know, we said, well, we weren’t sure about mission driven, but we kind of had this this passion, we’re gonna say that, like, we don’t have a vision statement, but here’s the passion of the company. And our passion, that we would get behind and measure everything by was any founder that works with us will never have to worry about cash flow again, you know, so if we can build a system like that, because I’ve been that founder, where I had to call, you know, friends, family and fools for a loan for next Friday’s payroll. And that was painful. And I didn’t like that very much. And so I said, you know, if, if we can direct everything we do, to that passion and measure the opportunities, so when something walks in the door, a shiny new opportunity exists, can I say, by doing this thing, at least in this business, by doing this thing, can I make sure that the founder, whoever I’m talking to never has to worry about cash flow again, so he has like a tight binding around the, the fences of or the the boundaries of that passion, and some stuff is really compelling, you know, you would chase projects and think about different types of things. And, and it just doesn’t fit. Likewise, it should tell you who not to do business with, maybe if they are your client, we’ve had honestly, we fire people, but we, you know, released some clients who we said, you know, we’re not achieving the thing, because, you know, in some cases, you won’t listen to us. In other cases, you have not provided the volume necessary to do this. You know, it’s, it’s unethical for us to take your money anymore. And so, you know, it sort of cuts both ways, on that you do the best thing that you can to, you know, make sure that you’re delivering, at least in our case, an extreme level of value to the clients that that stick around. And I think in previous businesses, maybe I did not focus, and I just chased the revenue. And I try to advise people not to do that, you know, don’t just chase the next shiny revenue thing, you know, let’s try to really grow and scale the thing that you have. If you find another opportunity, put it in the idea notebook and, you know, kind of doodle on it, and build this current business in a way that it can run itself. So you have the time, space, capital and energy to go. And you know, do the other thing, but but do it as a separate business.


Justin Nassiri  08:19

I like that I really like instead of values, having that passion statement that filters what you focus on. And I also really liked that thought of freeing up your own time, so you can chase the shiny object, but not at the detriment of the company and have the company you know, off roading with you. Another thing I wanted to dovetail off of is you talked about how you focus on service businesses. And I remember when you and I first spoke months ago, it’s something I appreciate the said about how everyone is so tech crazed, and you think that people are overlooking these service businesses? What Why is that? Why are these businesses so appealing to you?


David Ledgerwood  09:00

But you know, it might be like, sell and do what you like to do, right? You know, for me, I’m not sure that I’m making uniformly brilliant business decisions that would apply to everyone. It’s a space that I know I grew up in. I do think that there’s really nothing wrong with a business, we might look at a service business and say, you know, hey, 30 to 50% gross margin, when done well scales up really nicely in a bunch of that money falls to the bottom line. Is that the same as a 90% gross margin at mega billion scale for you know, a SaaS company. No, but we’re also not seeking and we can’t we can bootstrap a service business can be bootstrapped. I see people get really good at doing a service business, and then say, but we’ve got to productize you know, we have to turn this into a tech business, we have to turn this into MRR. And you’re right, I just don’t think that very many times those founders are amazing at doing the 180 degree turn, and turning it into a product company. So it’s just a very different thing. So you know, keep doing what you’re you’re good at, and don’t miss those opportunities to put a lot of money down. On the bottom line, we ultimately like you have to have a profitable enterprise. So we are, at least, you know, sort of in the US tech scene, and just obsessed with this idea that we’ve got to develop hands off self serve SAS tools that will MIT money. And that’s great, but you only hear about the good ones, you know, how many of them die on the vine, because, you know, a technical founder read too much TechCrunch. And thought that, you know, it will if I, if I build it, they will come You know, so all businesses difficult. I just think that at the end of the day, there will always be many founders, for you know, human businesses, there’s always humans behind all the businesses, and all of those businesses need to consume services, you know, one way or another, whether or not they sell technology. So that seems like a pretty ripe place to be. It’s sort of like selling haircuts, you know, you You’re pretty good unless you your clients all look like me.


Justin Nassiri  11:29

Well, I also one thing I appreciate about in your answer is the role of personal preference in niching. down and you know, you started by saying it’s, it’s a part of business that you like, and that you know, and I feel like sometimes I can get in debt. Apologies to our listeners, I’ve got major construction spontaneously happening outside my window downtown. Isn’t that always the way? Yeah, my lawn guy only comes when? Yeah, yeah, the dog only Yeah, it’s um, but it’s just kind of nice and refreshing to say, look, you know, there’s so much opportunity in the business world, you can have your personal preference play a role in what you go after, because that’s one of the beauties all sub niching down as you can really go after something that appeals to you and makes business. Yeah,


David Ledgerwood  12:11

I don’t know. For us. It’s just like, we can make people millions of dollars. That’s just cool. Yeah, cool. Go take your money and spend it, you know, do whatever you want, and start a sass company. That’s great. Maybe someday I will, you know, I haven’t happened upon the greatest, you know, idea that would that would scale. But I also think that if you’re honest with yourself about Lean Startup, and the way that we’re extensively all taught to do it, and don’t actually do it, is that you, you really need to manually test and and sort of battle out a real model before you try to specify and scale the hell out of a technology. Well, how do you do that you provide a service, you do it manually, it’s ugly and slow. It doesn’t scale. And tiny little pieces will expose themselves that you go that that’s the thing that I could turn into a SaaS product, but but not the whole thing. I just, you know, yeah, I just want people to be Be careful and not go bonkers trying to chase insane money. And when you can still make like millions of dollars, you don’t have to be the next unicorn. Unless that’s what gets you going. And you know, God bless. I hope you have lots of money.


Justin Nassiri  13:30

Yeah, no, I am. So in line with what you’re saying. And it’s like, there’s so many great businesses that don’t have to. It’s, it’s, I like what you’re saying, because you do have to start in a way that’s not scalable. Although scalability is the goal, you have to start with things that are inherently not scalable, and you have to prove them out. And I’m just thinking in my own path, when I raised money, I didn’t have to I had the money to build crazy shit that no one wanted. It was such a mistake.


David Ledgerwood  14:00

Yeah. Like, why is money free like that? Right? Like, you know, every day of the week, you read the search phrase, like, you know, such and such raises 50 million to take on the blah, blah, blah, to do something or another and you kind of go like, Where? Why? Yep. Why are there 300 people doing that? In a building? Something that’s real.


Justin Nassiri  14:23

Now, I agree. What about when we talked previously, you had shared with me I thought about how sales should be informing marketing. And I’m just kind of curious if you could expand on that for our audience.


David Ledgerwood  14:35

Yes, yeah. This I I’m really passionate about this thing. So I think you know, the trope like you’re your marketer, you’ve been around the sales thing it’s just like sales and marketing don’t get along. I mean, how many companies have you been to a sales is going up with marketing and sales people a marketing and marketing people hate sales, and there’s just this fundamental conflict and yet, let’s say we’re gonna stick with I know, like, people maybe don’t like the funnel anymore. And now we’re going flywheel or, you know, whatever. But any case, you got top of the funnel, which is largely a marketing activity, you got bottom of the funnel, it’s largely a sales activity right there in the middle is that place that we imagine this demarcation where, you know, the lead gets tossed over, and they go Good luck. And you and then you know, that’s where it’s a marketing qualified lead and sell says, This is garbage. It’s not a sales qualified lead. And if this is if there’s a fence, you know, and like, well, just not our problem anymore, we got some leads, you know, peace out. And on the other side, you know, the marketing folks going like, how come you salespeople don’t use any of this, like material, we spent 200 years making, you know, and they’re like, this is expensive, and we have to make branding. And we have to make, you know, messaging and this is important stuff. All of them were right. I started looking at that and say, you know, wait, again, if we’re going to, you know, sort of worship at the church of lean startup, right? At what, what are you supposed to do there, you’re supposed to do customer discovery. Now, most people, you know, sort of do a business, and they don’t actually do the customer discovery and interview, dozens and dozens and dozens of potential customers come up with, you know, actual real data. So let’s say we step into a business, it’s, you know, we already didn’t do that, well, what’s the best way to do customer discovery essentially, is a sales call, because it’s a one to one call with a person that potentially may or may not be interested in some version of the thing that that you do, or the way you described it, at least got them on the phone. So now we can ask a whole bunch of questions during that sales process, and every salesperson, at least in the service sector. And I think in general, it wants to do that discovery based selling, tell me your stories, hopes, dreams, what do you wish this would do for you? What’s the difference between now and then, so I can, you know, sell me sell the thing we do? Well, all that information just gets lost, you know, nobody does anything with it. So you have all those effectively customer discovery interviews. And I started looking at that and saying, you know, that’s all the data you could ever need. Except it’s a huge pain in the ass to extract it. I think this is why nobody does this really, there are you know, sort of intelligence platforms, you know, Gong and different things like that. It’ll consume your calls and give you you know, coaching information and different things of that nature for your sales reps. But we looked at the calls and said, Look, we record every call here, if you go through that, and unfortunately, it’s human, there’s no like, you know, real AI that can do this yet. And you write down literally every time every sentence from the prospect that ended with a question mark, you do that for 2030 4050 calls, you have every question that could ever possibly be asked. And you condense that into a data set. I call those content prompts. And I say here, marketing, sales and formed right now, these are the things that people want to know when you please create content, and marketing and messaging that addresses these things. Because if you do that, by the time somebody gets to the bottom of the funnel, they will in fact, have been answered to almost every possible objection, through one interaction engagement or another, that’s a lot better person to get on the phone, they will self select out if they just simply don’t agree with you. And by the time they get to a call, we don’t have to spend a half an hour trying to convince them that they’re in the right place. They’ve already satiated that need to feel secure in their purchase decision. Now, we’re just working out details and having a good conversation. So if you do that on a repeated basis, that’s the manner that you can work together. I don’t disagree that there ought to be centralized marketing materials, I just question what those materials are about. And I think that’s where sales enablement materials came from, because salespeople are being like this marketing. Doesn’t that like, that’s great that you have an 18 page white paper about why people should do this? But it doesn’t answer anything that I need them to know. Like at this, you know, sort of point level, on a one to one basis, well, here are the content prompts, produce a bunch of stuff that answers these questions in 10 different ways. And we will drive up the close ratio, because people will feel understood when they pass through the funnel. So that’s the theory and that works. It’s not a thing you can just plug into though, you know, that’s it’s just tremendous amount of work. So that’s, that’s one step that we do every time we enter a client.


Justin Nassiri  19:30

That’s so great. I read this book forever ago called they ask you and they asked you listen, or they ask you answer and it was similar. It’s kind of like anytime you have a question that needs to drive your marketing content. And it leads me to another question I wanted to ask, which is, you know, you’ve helped so many businesses take, you know, make it to the next level. And I’m curious, you know, obviously, you know, there’s a whole business you’ve built around this but kind of common mistakes You see founders making when it comes to sales, and it seems like one of them that you’ve just articulated is keeping track of these questions and letting that drive marketing. But I’m wondering, is there any other trends that you see stand out that you’re like, Why do people make these mistakes?


David Ledgerwood  20:17

Yeah, there’s a really interesting thing. One of the reasons I love at least again, in services businesses does not apply to your SaaS business, there’s other metrics. But in a services business, b2b, you’re going to find right around that 500,000 revenue point, on average, could flex up and down, you’re going to find that the things you were doing to get there are no longer going to help you scale and grow revenue. And the reason is, up till that point, you were able to do this thing. And I know, everybody who’s being honest, that runs a sales or services business, or has bought from one has seen this abject Ly, we customize every proposal, every engagement is different. We don’t do a cookie cutter approach, blah, blah, blah, on and on and on. That’s great. And that will only get you to a certain point as a business provider. So as a service provider, right? At that point, you need to then analyze all the things that you have been doing that you do on a regular basis, you got to figure out that 80%. Like, we do pretty much the same thing, even though we call it a custom proposal. That’s cool. Those 80% things ought to be divided out into some kind of package scenario. I love the three package vibe, you see this and this, this is straight out of like SAS playbook, right, you got your good, better, best recommended right there in the middle, everybody’s seen a pricing page that looks like that, make your service into that thing. And then you got another 10% of stuff that you can go. Awesome. Sometimes people want this stuff, it’s a little bit more money, it doesn’t fit exactly into a package. But let’s make that an add on. So now we have a menu that has, here’s the most of the stuff, here’s all your main courses, here’s how we deliver it. You can also buy side item if you want to, right? pretty normal disposition there, well just add this and take off the pickles, no problem. Okay, we can do that. So there’s your next 10%. The final 10% Is that weird stuff that people walk in the door and they say I want you to do this thing. I want all that other stuff. But I also want you to do this weird thing that you have never done before. And that’s great. That’s optionality for your business, you can bring that back. And you can say, do we want to develop this really weird thing? That is not in the other 90%. But we can charge a lot of money for it. Okay? And the answer is, does it fit into that passion statement, you know, if we can plausibly say this is a place, we might want to advance our business, charge that customer for a lot of money, you know, three times four, or five, six times as much as they should be, because they actually want it and build it out in a way that you can then say, I now have either a new add on, or I have a new component that I’m going to go back and upsell to all my other customers and increase my package capability. So by actually doing the same thing over and over again, there are myriad benefits to the business because now I can say, let’s say you’re the customer success team, right? You’re the operations delivery team to the finance team. Sales can call down the you know, hallway or zoom call or slack. And they can say I just sold package B with add on to everybody business wide now knows how much to charge for that. Exactly what to deliver exactly what formula to and recipe to run. There’s none of this back and forth of what you mean by this. And hey, you wrote that scope of work differently. And what about this? And what about that and all that Oh, hey, that got lost in the handoff call. That’s why you don’t do that anymore, because you can’t scale it. So that huge problem happens when people just do this. I write a custom proposal for everybody. It Peters out. That’s why your revenue has stagnated. You can’t do that anymore. You win.


Justin Nassiri  24:16

I love this thought of of almost like productizing the pricing. Do you have strong feelings? Having worked with so many companies about publicly displaying pricing versus being opaque and making them come to you for it?


David Ledgerwood  24:31

It depends on the business. Yeah. If you’re in a space with a boatload of competitors, and you’re trying to position as a more premium offering for that, and a lot of services business really are much more boutique like that, if you’re going to try to make a little more profitable. I tend not to put the pricing out there. Although if you were to go to our website, you can clearly see you know, our pricing so i think it’s it’s really the question of How many businesses ostensibly do the same thing as you, because if you’re just going to give that away, you’re kind of like the gas stations, you know, sort of across the street from each other, like, you can’t have a big Delta, because you didn’t get a chance to sell them before they kind of priced you out. However, if your niche enough, you do a thing, you get a lot of referrals, you know, I mean, we’re okay putting our pricing out there, because it’s just what it costs. And we know we make people millions of dollars. So if you don’t want to pay that, that’s okay. You can call the random lead setting SDR, something, something, something as a service, you know, whatever other thing you want, there’s a million different alternatives to what we do that not necessarily direct competitors. So the answer is, it depends. But most times, we don’t put it out there because we’re trying to premium position, the client. So


Justin Nassiri  26:02

I love it. Just to two last questions. First one is just where can people find you? Where can they find out more? How can they get in touch with you?


David Ledgerwood  26:11

I am David ledge ledgerwood. on LinkedIn, that is the place I post tons and tons of videos and content. I co host, a podcast called leaders of b2b and we would welcome you to listen to that. And our website is ad one and add numeral one, z r We’re coming for you whoever has that calm. I want to let you know right now, but they so far, they have not answered my emails.


Justin Nassiri  26:49

Last question, I always like to keep open ended, which is you’ve given so much value here, we’ve covered a lot of ground. What have we not covered that you want people to know about sales about marketing or entrepreneurship?


David Ledgerwood  27:04

Yeah, I’ll go to the startup founders. You know, I think if you’re bootstrapping, and you’re you’re not certain of a technical idea, like it’s a really good place to just think about a service pull it out of your things that you can do, you know, qualities you can provide somebody while you you figure it out. I was a side hustler, you know, Sir, how did my day job and you know, did started by startups, you know, kind of at my corporate desk, and you know, did that that whole thing, I think, I think you know, sort of buffer your cash flow as a, as a, you know, startup founder, just to give yourself as many reps and as much runway as you can, because you’re invariably wrong. The problem is, you don’t know what’s wrong you are and you know, it costs a lot of money to be wrong. And particularly I see people a lot of times, you know, kind of bet the farm but the family on, you know, a half baked thing, like just, you know, you’re good at a thing or you think there’s an idea and we’re gonna, you know, bargains her house and invest all this money in it. And I just, I would like people to not get wrapped up in the hustle hustle insanity. Remember that for every amazing story you hear. There’s like 1000 stories that are not amazing and the reason that quote, nobody is doing this, it could be that you’re brilliant. Maybe he could also be that everybody who tried that is out of business and broke now and you can’t even find a website about it. You know, so just be careful with the lies that you can convince yourself of being a particularly if you’re a you know, a sales type like me because I can spin the narrative in any way that makes my brain happy enough to make me go do that thing. And to that I say surround yourself with people who have excellent discernment of different types so I can smell how to make money from stuff I don’t have the you know, sort of focused ability to you know, check myself when I get excited so I got a business partner who is very grounded and very operationally based. So I know that we won’t get in trouble when I go have a bunch of conversations on podcast because stuff will get filtered you know when it comes in the door so I guess those would be my my biggest tips that I wish you could make up experience. You know, it just I’m not sure that that you can so you know, earn your earn your loss of hair and your your gray beard like me.


Justin Nassiri  29:38

I love both of those points. I think that one of the reasons I like to see entrepreneurs bootstrapping is they have to be so judicious with every dollar and I really like what you’re saying is like you don’t really know where it’s going to fail and like making sure you’ve got dry powder because things I always just say that you know, always takes 10 times longer and 10 times more money than you ever thought it would and I see Entrepreneurs throwing money, you know, at the optimal straight line path to success not realizing the zigzag that’s gonna get them there and they run out of money before they can do it. And I also really appreciate hearing about you and your co founder and how you balance each other. I definitely relate to you have kind of the very easy to get excited and it’s great that you found that person to anchor you and to kind of minimize the oscillation so that the team is not getting whiplash as as sometimes my team does, they get fired up. So David, thank you so much for for your time today. And at the show notes for this episode, we’ll have links to everything we discussed, as well as where to find ledge on LinkedIn where to find leaders of b2b and also add one zero CO thanks so much ledge. Thank you.

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