On this installment of the Raw and Real Entrepreneurship Podcast, Susan Sly delves deeper into her conversation with David Ledgerwood, co-founder of Add1Zero, in part two of their interview.
Topics covered in the interview
Entrepreneurship, mindset, and resilience
Building a sustainable revenue
David Ledgerwood’s Bio
Ledge’s career sales have topped $34M, with an average deal size in excess of $150,000. He’s sold B2B software and services for more than a decade from each of the founder, partner, and employee seats.
Pro Studio | Comfortable Behind the Mic and Cam
Ledge hosted Gun.io’s The Frontier Podcast where he interview professionals across the software engineering spectrum for more than 150 episodes that are still generating ROI for the firm.
Diverse Experience | Great Stories | Lasting Lessons
Prior to starting Add1Zero, Ledge led Sales and Services for Gun.io, during which time he sold and managed more than 100,000 hours of development and 10x revenues to a mid-7-figure run rate.
Ledge’s 20-year business career began in professional services at PwC where he carved out a weird niche as a Bash developer and checked the Fortune 500 box with UPS, JPMorganChase, and Aetna. If you’ve received a package or deposited a check, there’s a pretty decent chance some piece of code he wrote was somehow involved.
He moved to a major publishing company right about when Web 2.0 started to eat newspapers and periodicals for lunch, giving him a front row seat to disruption and honing his taste for entrepreneurial pursuits while learning how Sales and Operations must gel for customer success.
In 2007 he walked out of his stable job and moved from New Jersey to Nashville to start a company, which he grew to a $500K runrate before crashing and burning in the Great Recession. Without taking a day off, he joined an EdTech firm and ran efforts to drive $2M to $20M growth. Then he took a COO role while side hustling to coach, mentor, and build his network of founders and execs.
I’ve got 5 kiddos and an interstate marriage. I hop between Nashville and Dallas.
Follow David Ledgerwood
Susan Sly 00:00
Well, hey there, I hope you're having an amazing, amazing day. I am excited about part two of my interview with David Ledgerwood. So in part one, David and I spoke about the economy, we spoke about how it's a little bit more difficult given all of the things that are happening in the world right now and interest rates and where people are at with an inundation of information to generate quality sales leads, but doesn't mean it's impossible. And David,, in this episode is going to talk about how to essentially make it rain when it feels like things are flatlined, and being your own momentum, and he also shares how he has been able to not get rid of anxiety, because a lot of entrepreneurs do deal with anxiety, but how to live compatibly with it, which is really interesting. And before we get into today's episode, I want you to check out AIM7. AIM7 is available in the App Store. It's an absolutely incredible piece of technology that I use myself that integrates with your Garmin, which is what I wear, your Apple Watch. And what it does is it customizes your workout, It customizes your rest, and it helps you navigate entrepreneurial stress. you can get a free trial, if you go to aim7.com and put in the code rawandrealaim7 and full disclosure, I am an investor in aim seven. So with that, let's go ahead and get started with this episode, part two, of my interview with David Ledgerwood.
Susan Sly 01:49
This is Raw and Real Entrepreneurship, the show that brings the no nonsense truth of what is required to start, grow and scale your business. I am your host, Susan Sly.
Susan Sly 02:03
I love how transparent you are. From mindset perspective, you said not to have your emotional hooks in the business. And essentially don't let the business define you. Right? How do you not do that? How do you not take it personally? And how do you say okay, this one failed and now I have the guts to go and do another one, and another one, and another one, and just keep on, like it's um, you know, like any of the gray boxing matches, right? Ali goes down and then he gets up or Foreman goes down and he gets up and he gets up again. And he's all bloody and stuff. How do you how do you do that?
David Ledgerwood 02:45
I don't know. You know, it's like I leave. In some senses, I left myself no other option. But to pivot around me, let's talk about itself. Sort of like I am an entrepreneur, like this is my path, I build things. And some of those things are not going to work. And then they just like, it's not, when you realize what's left after like, things burned down whether you like it or not, you realize the relationships are what matters, like, am I raising good kids? And am I being a good person? Do I just feel good about the work that I deliver? And in my business, like I finally was able to just design a thing or it's like, I make founders millionaires. Like, that's just cool. I just like, I like that. And then we take a little piece off to say, you know, but that's, that's just fun. Like, I'm exhausted. I work hard, you know, but it's not ever been about this, like hustle and exit and, you know, craziness for me because you get so tied up in that and it will just eat you alive. You know, so I've always been this sort of contrarian of not being in that zone, I guess, you know, like, just sort of protect what's important, like, you're, you're getting older, your health matters, you're, you know, work out, like, don't eat crap, like, as says from the guy who drinks like four Celsius every day, you know, so like I have, I have mine too, but buy Celsius stock if you're gonna drink four Celsius every day. You know, so collective mindfulness is probably really important. Like and this is also like, you know, it's like you say raw, transparent, whatever, like I was a freaking mess until I was like, 40, you know, and like, do a lot of therapy like, you know, just like, admit that you don't know things like, the more you go on you realize like, your wisdom is just an accumulation of all this- not to do that you can innately now you've done it wrong so many times, you can just avoid that, and, and recognize it. And I'd also say to people, get over yourself. Like, I wish that I had listened to the people who had done it before me when they sat down and like, this doesn't matter. Like now I, I suspect that like I said, it's like maybe the rite of passage that you just like value the wrong things at the beginning, and you think you're smarter and like, your arrogance carries you, but you're not, and you're gonna get delt a handful of crap, you know, for for your arrogance. If you can actually be humble and listen, when you're in your early 30s, then maybe you won't lose several million dollars trying. But I don't know, it doesn't seem like that usually goes that direction.
Susan Sly 05:52
To your point too, David, I had Dave Asprey on the show, and, and Dave was talking about the team, right, you know, and, and people can have whatever view they want of Dave Asprey. But as an entrepreneur, I mean, seriously, dude built Bulletproof, that whole brand. I mean, it's just amazing. And he was talking about a team, you know, a therapist, a coach, you know, mentors, those things. And I think that the road to being an entrepreneur can be extremely lonely and left to our own devices, whether it's alcohol, or drugs, or whatever the device is, I know, for myself on the journey and multiple businesses, including one that failed in 2000, I did take it personally, I still take business very personally. But I realized for me at this stage of the game, that I have to have a team. And if I don't have a team and I'm trying to do everything by myself, then I'm not also bringing in the best ideas that can bring things forward. Right. So I love, I love that you said that. So let me ask you this, your business now, right? And not you have consulting, you have your podcast, and then you have Add1zero. And Add1zero is doing well. Like this is the culmination of I failed, I succeeded, I learned a lot, I grew a lot. So tell, you know, tell the listeners, what is this business and how is this a manifestation of David's decades of experience?
David Ledgerwood 07:34
Yeah, yeah, please, we all learn from what not to do, right. So I had, I had this concept in my head, one of my adventures was, you know, coming to an end where I, I had, when I looked at my experiences, and I was like, you know, what I have done well, is coming to companies that are in the b2b services realm. And they might be an agency or professional services, you know, MSP, you know, something like that. And several times in a row, I came into a business that was doing, you know, 300 grand, or 500 grand, and this is like, which sounds kind of cool when you're starting from zero, and then you realize it's not really a lot of money, you can't do a lot with that. But I took those and I made them into, you know, $5 million companies. Like that was my thing and my zone of expertise. So I said, you know, what problems did I face along that way when I did that, and so maybe you have agency owners or, you know, consultancy owners, or something like that, here, listening. And what I think those businesses were often failing to do was, was build any kind of sustainable, you know, kind of revenue engine behind them. The view, would you build a thing, because you had people that were friends, and they paid you and ultimately, you ran out of that, and you never built a direct sales channel at all, you know, this is like, unless they were your friend, and eventually you ran out of friends. They weren't gonna buy anything. And so you had this false leap to that, you know, sort of like, hey, I can pay myself, you know, 150 grand, and like, I'm doing really well, but like, we ran out, and then what would you, what would you do there and I came to realize, like, it's sitting in the seat of the guy who did it all and built it by myself and how to run every piece of sales. That in fact, what you actually needed was a robust operating sales, what we now call sales ops and I don't know, people, either I wasn't reading it, or people weren't talking about that. And then somebody probably was talking about it, and I was just oblivious. But I realized that that's what was necessary that there was no way. Why could you get a fractional CMO or CEO, or CFO, like there was all these things, but you couldn't get a fractional, like revenue operation that didn't just give you advice, like you can buy endless sales coaching, and live sales consulting, they will give you all kinds of, that somebody else is supposed to do. And like, well, that's not awesome, because what I like is like, I want to bring people real money. And why can't you do this? Why doesn't this exist? And so we built it. And I now know why it doesn't exist, because it's hard. And it didn't scale the way that I exactly thought. But it did work. It worked about three times slower than I expected it to work. And now you know that the flywheel took longer, but it does work. And we're able to come in and just go like, we will take over your entire revenue function for you. If, and part of it is like understand your ICP, right? Like super, super, super niche weird ICP is if you are a founder of a b2b services firm, and you just don't want to be in that sales seat like at that, at that point, exactly that point where you're doing enough to sustain that half million dollar revenue type of mark, you need to choose like your fork in the road, you are there going to be on sales calls all day long, and executing the sales function, or you're not, and you're going to be an operator and you're going to scale an operation. If you want to be that second one, you now are in the unfortunate position that the last thing, and the hardest thing to outsource and let somebody else do is that sales and revenue function. So let's provide that. And I now can tell people that you know, actually, the first thing that you should get rid of is that because we can do it for you. But that wasn't the option. And I think if you read any of the education around like what we tell agency owners and consultancies and things like that, the last thing you can ever let go of is sales. You have to do it yourself. You're the founder. That's functionally not true. And if you don't want to be that founder, there exists now a solution for that. It's still hard. We just like sticking our head against the grindstone.
Susan Sly 12:30
Well, and to your point, right, and it's, I get how many emails a day, do you need a fractional CFO, do you need like, do you need this? And I 'm like, would you just go to our website, and you can see, you know, our team of talent, but yeah, right, exactly. But you never ever see that David, and especially there are a lot of, a lot of times in the agency world too, there are a lot of creatives, and they're really good Creatives. And they create and they create, they create, but they don't sell because it's like, there's this fear, like Don't call my baby ugly, right? Like I spent three days building this beautiful logo, but don't call my baby ugly, right? So it's like, it's like, yes, I want to sell but no, I don't want to.
David Ledgerwood 13:17
I will call your baby ugly for you. Yeah, I most definitely will. You can still love your baby. But like, we cannot sell your baby the way that it is swaddled, let's put it that way. So you know, we're gonna fix all this stuff. And yeah, you're right, like brilliant creators, like practitioners, like, Who amongst those people went into business so they could sit on zoom all day, trying to get other people more stuff to do, and then pay those other people and not pay themselves. And I saw I did it. I saw it. Like, this is wrong like this isn't why those people went into business. And it's, they hate their own thing. Like you talk to people like just They're freaking brilliant, like accountants who can build out a technology stack and automate every single number in your business and dread, absolutely dread, like what's your worst day? The day where anybody put a lead in my website because I have to talk to them. Now that's my best day. Like Bring me more of those and also I'll probably triple your price. And it's just not the way, I don't know like, that's my craft right lik,e I fabricate money out of conversations you know, that's what I do. And I like it that way. And I'm very careful to say like, do not misunderstand that this is about like, most have lunch on sales calls. It has nothing to do with that. It's the operational infrastructure and other humans that make it possible for me to sit on this zoom and talk all day. And it's good but it's still like, we sell we close, like actual closing of deals that have ink dryness, not ink anymore, we don't get to do ink but like that's a thrill Right? Like let's go, let's go book $15 billion plus logos for you next year, all you need to do is make those people show up for a call, be brilliant freakin marketers. And get out of the way because you don't know any of these other things. And we are like that level of aggressive. You can take the New Jersey out of the, would you say take the boy out in New Jersey, but not the jersey out of the boy. So I live in the south now. I could still drop loads off if I need to but ultimately, like, raised at the jungle, right? Go kill stuff. Like that's, that's what I like. And, and also I'll say like we tried to scale and let's hire a bunch of reps and let's stamp out copies of our model. We did it to ourselves. And we're like, this sucks. Like, this isn't like I just became a sales manager. I don't want to be a sales manager. I actually just want to go kill things. And you know, sort of like, know who you are. I'm a glorified sales rep with a really good operations team. But that's what makes money.
Susan Sly 16:18
Yeah, no question. And to your point, that there's a difference. You know, and obviously, you know, I come from a sales background, right? You don't build teams that do 2 billion in sales in three different verticals without knowing how to sell. I know for myself, if someone on my team brings me into a sales call, I'm so detached from it. Like for me, it's like kind of doing a dance like, you know, it's just like, okay, yes. If they say this. Yeah, yeah. And it's the detachment because they see people holding on to the sales so hard. And they just want it and they want it and they want it and it freaks the other person out on the other end, that desperation,
David Ledgerwood 17:04
nothing will sell worse than thirstiness. Oh, my gosh, and founders are the most thirsty and I get it like, you want that deal so bad, but you just killed yourself. And I think yeah, maybe as the third party, were able to even bring that other level, you know, detachment where it's just like, I fundamentally believe there will always be one more call if we do marketing right. And some of them break my heart, you know, like, come into the end of q4, I'm ready, like we're gonna pitch some monster deals. And we're gonna lose, like, and well, Merry Christmas, you just lost a $500,000 bid. But it's not the right bid for the company. And no, I'm not lowering my price. And my margin is 10%. Like, that's stupid, you know, and don't chase it. Don't be thirsty, like being thirsty and showing the desperation that you want that deal, it's just like, repellent. It's gross. Like, I don't even want to see that. Don't join my calls. Because you are hurting all of us, you know? And sometimes you have to have the tough conversation. We call it calm confidence. You know, I've been, I've had a call the swagger, I'll come in and make a deal. Like I'm, you know, maybe Okay, fine. But I don't know that that's it. I think it's, you know, just the fundamental belief that there will always be a next one. And there's going to be dry periods like the summer sucks, like, it's just sucks my energy out like, these calls are terrible. These leads are terrible. Like, nobody will return anything like, it's like the my, you know, my Harry Potter power gets sucked away, because I can't get on a call and slam some deals. But that happens. And then you close three in a row, like in September, October. And it's the discipline of knowing that there's just going to be more and I guess that's what is that abundance mindset, you know, you should or like, I don't know if I can manifest deals, that'd be cool. But
Susan Sly 19:12
it's the law of sowing and reaping. Right? There are seasons and the summer. I noticed too. And before David and I started doing the show, Dave was like, Where are you today? Because you're traveling. I've been I have the day we're recording this. Raw and Real Entrepreneurship. I am so tired. I have been on the road, eight weeks straight. And it was like my central nervous system was so wound up. I just got back from Toronto where I was a finalist for one of the top women entrepreneurs in AI. I was speaking at that conference, seeing my aging 83 year old father who, he's probably listening to the show. He needs to get into some, Yeah, his name is Joe. He needs to probably go into an assisted living facility, doesn't want to go, dealing with that. And David I am tired, Oh, yesterday morning, we had our daughter's cross country meet, which was great. She qualified for the state championship. So happy about that. But I am tired today. And it's like my central nervous system was like wound, wound, wound. And now it's like I'm coming down crashing. I get to be home one more week. And then I go again to Boston and Atlanta. And to your point, I'm on the plane, and I said to the flight attendant, at United, I'm like, This is crazy. She said, we have, and their stock isn't reflecting it right now. She's like, this is our busy, we just came out of our busiest quarter. And it's like you said, there's this pent up demand for, I have invitations to speak at so many conferences. I'm like, no, no, no, like pent up demand for conferences, pent up demand for travel, people are distracted. They have an inundation of information, all the things that are going on a world. And so in sales, we have to work harder. And this is the last question I want to ask you. But in my opinion, we're working harder to get the quality lead right now. But that's okay. I'm not afraid of the hard work if I have to work harder to get the quality lead 30% harder then so be it? What, as we close, and keep in mind, you know, right now, I can't even think, like Germany is like our number four country, I don't even know like, it changes every month, our team shows me. So if people listening all over the world, there are small business owners that have an at home business, there are people, friends of mine who listen who work for companies that they're thinking of starting business, then we have people who have larger businesses, in your, given everything in your decades of experience, in the economy we're in right now and everything that's going on, what is your best tip for sales right now, given all of it?
David Ledgerwood 22:05
Like, I think people forget, like, you know people. Tell them what you do, like telling is selling. And I mean, the old model of that used to be like tell your hairdresser, tell your you know, whoever right, but like, how many people do you talk to on a regular basis, even professionally, that actually have no freaking idea what you do or provide? And I just think like, go talk and activity bears results, right? Like so. It's so easy to just be like, just sit back and let my you know, hands off. You know, ads are my you know, my marketing like, Oh, why don't I have leads, like, freakin talk to your existing customers. Upsells like, cross sells like, do you know anybody? Like, I've, just this summer I undertook like, Well, if the phone isn't ringing, that actually is not a thing anymore. I just was like, say Rolodex but no calls are getting booked. Well, there's 60 clients who pay us every month. I'm gonna book calls with them and just talk to them about what we do for them. Well, it turns out that most of them have more things to do. They didn't even know that Fermax does that. But I'm actually just like, I'm booking a call and just going like, I need to, I just want to learn, I want to check in with you. Like, is everything going the way that you need it to go? Is there anything else that we can be- done for you? You know, other clients are asking us for whether or not this is true. Other clients are asking us to add this service like it keeps coming up on my calls. Is that a real thing? Does that happen to you too like, customer discovery isn't just for like before you launch your idea. And I think we lose that connective tissue when we get down on our ourselves. But it's also like, it's exciting. Now, you don't always get an opportunity to be on podcast, but how I honed my pitch was I paid a podcasting agency, book me on like 30 shows, and I'm gonna have to explain to real humans, what the hell I do in this thing that like, nobody else does this. So how do I refine talking about what I do? I refine it by talking to real humans and being grilled by podcast. So it's about like, you know, does that even make sense? How do you actually do that? And now rolls off my tongue. Right? But like, what is that? It's just activity. It's just conversations like that's, that's where it all comes from. And I think we just forget that you know, we just get in our own little lonely shell and wait for you know, the Google bots to book us meetings. And that's just, it's not how it works. It's now how you get a job. It's not how you find work to do.
Susan Sly 25:08
Yeah, it's that, what I'm hearing is for you, that silence is not golden. And if there's silence, then there's action that you need to take in order to create and make it rain. And what the average person does, this is why the 10% of the people hold 90% of the world's wealth, is because what the average person does, and I know that emails about that statement, it's true, go check it out, is the average person waits for the hand up. And then there are those of us who make it rain and take action, and it doesn't matter if you're tired, it doesn't matter what else is going on that, you know, if there's no leads coming in, that you've got to be the momentum, and you've got to create the leads, you've got to go out there and have the conversations and I base it personally on how many conversations have you had, and it's not a good day for me personally, if I haven't, you know, told the story of at least one of my companies at least three times that day. So
David Ledgerwood 26:15
it's very reasonable. Yeah, absolutely. And it's, it's like, why do you expect something to happen if you don't have inputs, and it also, like, I don't want to, like, I'm not a hustle culture, you know, person, like, if I'm tired, like, I know, I'm gonna perform like, sh- on this call anyway, you know, so like, just tag me out, like, I cannot look at a screen for another minute. But when I'm on, I gotta be on, and I gotta get up at four in the morning, because this proposal is due before I drop my kids to school, then that's what's going to happen. And I know, I'm gonna pay like, I'm, I'm just getting older now. Like, I can't roll like that anymore. You know. So like, I'm going to need a nap at like 4pm. But I'm going to do it because it must happen. And I like being in charge of my own destiny. I like having a full calendar, I have realized in managing chronic anxiety, that I must have a structured schedule, even on the weekends. Like it's weird, right? Like, I'm not a relaxer, and I feel worse, when it isn't like, what are you doing this hour. And it might just be like, block two hours to rake leaves outside, block two, block an hour to do laundry. But the fact that it happened on my calendar prevents me from spiraling into this weird spot of paralysis. I don't-
Susan Sly 27:43
I love that you embrace that, because I'm exactly the same way. Like I thrive, the structure. And even today, feeling like I'm feeling, I'm like, Okay, I do this, this and this, and then I'm gonna schedule a tap out, and then I'm going to tap back in. And I know that about myself. And in that transparency, David too, a lot of people who are entrepreneurs. I've hundreds of interviews, have issues with anxiety, have issues around managing emotions. And the thing is, when we're in action, we don't have time to be in our head, there's that saying, Be in your head, you're dead, right? Like, and that and I love that you share that. And I hope that people listening are going, Wait a minute, maybe, maybe just maybe if I'm struggling, that maybe there's a structure issue, obviously, you know, get help, talk to a professional and have the discipline to create some structure for yourself.
David Ledgerwood 28:45
Well, in my case, it was like, you know, pay the professional and weird actually do what he said, you know, like, it's not just enough to talk about things right. You know, and I think that that was important for, and I actually find it was like, You know what, why am I paralyzed on a weekend when there's nothing to do? Like, why am I standing in my kitchen doing nothing and just like Doom scrolling the news or like this is so stupid and just the act of disciplining myself to log that time on the calendar somehow aligned. I can't explain it I don't know what my neuroscience is and I can just say that it worked and so follow the damn plan and hire somebody else to do it if you can't. Like, it requires two entire humans to manage my calendar and my email during the week and then maybe I just collapse because I don't have that structure on the weekends and I don't know your background. I think you you are some kind of athlete, right, like in is triathlons? And I came from several decades of distance running, where I had, like, you know, essentially a drill sergeant at all points telling me what to do, and nothing else mattered. And then I think the loss of that structure, I didn't know what to do. And so like, alright, well just construct that from my business life and for my personal life, you know, also, but no one teaches you that. So, you know, keep on keepin on, it's going to be okay. And anxiety is also just an emotion that you can be self aware of, yif you know how to fix it. So
Susan Sly 30:39
I love the wisdom and that piece about that some days there are going to be easier than others, right. Was the same mama told me there'll be days like this, like, we know that that's going to happen as an entrepreneur in sales, building a business, whatever it is, what is that one thing you're going to do to move yourself forward. And for people who are listening, and maybe they have an agency, they're looking to grow that business, definitely go to David's website, it's add1zeros, tit's the number one, zero, and go on LinkedIn. David is on LinkedIn and follow him, connect with him there. And if you've, if anything has resonated for you, we'd love a shout out, a share. And I love five star reviews. I read all of your iTunes reviews, you can review on Spotify, wherever you're listening to the show. Just do you. And if, if there's a question that came up from today's episode, go to Susansly.com, submit the question, and we'll get over to David's team. So David, thank you so much for being here.
David Ledgerwood 31:47
Susan, thank you, you're a gem. And this is a lot of fun. I'm so honored to be invited.
Susan Sly 31:52
Thank you. All right, everyone. Well, this has been another episode Raw and Real Entrepreneurship and I will see you in the next episode.
Susan Sly 32:05
Hey, this this Susan, and thanks so much for listening to this episode on Raw and Real Entrepreneurship. If this episode or any episode has been helpful to you, you've gotten at least one solid tip from myself or my guests, I would love it if you would leave a five star review where ever you listen to podcast. After you leave your review, go ahead and email reviews at Susansly.com. Let us know where you left a review. And if I read your review on air, you could get a $50 amazon gift card and we would so appreciate it because reviews do help boost the show and get this message all over the world. If you're interested in any of the resources we discussed on the show, go to Susansly.com That's where all the show notes live. And with that, go out there, rock your day, God bless and I will see you in the next episode.
Susan Sly 32:58
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