Ep. #14, Goosebumps with Walter Roth of Simple Lens

Rachel Chalmers: Today I'm so happy to have Walter Roth on the show. Walter coaches individuals and organizations on how to achieve repeatable sales through the first principles of sales and self-mastery. He's experienced at setting up new sales teams in markets ranging from government and new media sales, to IT services and mobile health.

He's also experienced in fundraising and company formation. He left college a semester short of graduating to raise VC for a startup he headed and later served as entrepreneur in residence at Allegis Capital Venture Fund.

Walter has worked in all kinds of roles within the industry, including executive management, board management, business development, sales, recruiting, product development, and marketing. He's a mentor for the Founder Institute, Gateway Incubator and Alchemist Accelerator.

Walter, thanks so much for coming on the show. It's great to have you.

Walter Roth: Thanks for the invite. I always love talking to you.

Rachel: You are an incredibly gifted teacher of founder sales, and your guidance has been transformative for me. As for many of your other students. What becomes of the all important founder sale in the age of generative AI?

Walter: I think it becomes more important.

Rachel: Oh, I'm so happy to hear you say that. Say more about that.

Walter: In the age of AI, I think we all become founders.

I think that we all have to find what is our place in a world where AI can do what we do and oftentimes better? And you know, for big companies that have product market fit, they're big, they're established, known market, known ICP, known pain, use cases, business cases, right? All of that is in question with AI. So, you know, you might be head of a big company and all of a sudden you're going to find yourself in founder sales.

Rachel: Mhm.

Walter: And so I think in the age of AI, we're all in founder sales. And it's very different than doing one's job or selling something that's known. When you're in founder sales, you're selling into the unknown. It could be a new product, a new use case, a new way to market.

You often have a new team, and it's new skill sets. So I think founder-led sales is going to be the most important thing for both founders of your traditional startups as well as salespeople at traditional companies, as well as anyone that's running a large established company as CEO.

Rachel: That's a really cool perspective. What we're all trying to do is establish a business of which we are, you know, the core IP and asset, and we're selling it to anyone who will listen.

Walter: Absolutely. And when you're in a startup and you're doing founder-led sales, oftentimes the prospect would never buy from you unless there was no other way, unless their back wasn't up against the wall, right? Because we all know buying from founders and startups can be a very risky proposition.

And so the biggest trait in founder led sales is to be able to lend one's nervous system to buyers who have to transform. They have some problem, that doing nothing isn't acceptable. Doing it with like a big established company where it's proven, low risk, isn't acceptable, and doing it now is a requirement. They can't wait. And so founder-led sales is going to be more about helping the market make sense of who they are, where they are, why they exist.

You know, it's the biggest platform change, not just in our lives, but pretty much in any human lives that existed up until now, and founder-led sales, the quality of the founder's nervous system to be able to hold the change that's going on right now and to get a champion at the buyer organization, to get the conviction, to choose you, and to choose a path to transformation, and to collaborate and work together.

The founder's nervous system, their DNA, their first principles approach, their fast feedback loops, that's what's going to make the difference. And so buyers are going to be kind of betting on founders because the whole world's changing.

When you first started dealing in enterprise sales, it could be nine months to infinity until proven otherwise. The whole world's going to change so much that you're kind of betting on the founder and the founding culture of a team, once you're beyond founder-led sales, that's going to be relevant at the start of the buying journey, as well as at the close of the buyer's journey.

And then as you're implementing and getting the value from what you bought. So founder-led sales and the qualities of founders in the buying process is going to be even more important than it already is today.

Rachel: I love that answer because it's a wonderful distillation of the insight that you gave me. When you and I were working together at Alchemist X. I was like any founder trying to do sales, very anxious and very scared that I would fail.

And you, by focusing on that nervous system reaction, gave me a way to use that to empathize with the people who did indeed eventually become my clients there instead of portraying that physical response in me as weakness, you let me see it as strength.

And I think that's fascinating in this context of what do humans have that machines don't have? We have our flaws, we have our fears, we have our embodiment.

Walter: Yeah, and AI depends on us to give it information.

And one of the biggest problems in founder-led sales is that founders go into a sales situation and they might feel uncomfortable, they might be triggered, they might feel like the prospect has all the power. You have this power dynamic. It starts to get fight or flight to come up. That causes one to kind of narrow in what information they're bringing in, right? They're not as flexible, they don't see all the options on the table, and they're not able to collaborate with the prospect.

And oftentimes, the buyer has been burned by salespeople. So their initial stance is, I'm going to keep you at a distance. I'm not going to tell you anything. I want a price and a demo. But we all know that's not going to serve them.

What they need to do is open up and share their problems and have, you know, a salesperson or a founder to be straightforward and open and honest to see like, can I end this person's suffering?

And when the prospect is still closed, and they're kind of keeping you at an arm's distance, i t's the role of the founder to somehow not get pulled away in fight or flight, but to have the understanding that as much as it's painful and suffering to sell, it's just as painful and as much suffering to buy.

Rachel: Yeah.

Walter: Right? The seller has to sell and they got to hit that number. The buyer has to buy and then get to transformation, has to justify it. They put their reputation, their job on the line.

And so oftentimes what happens is salespeople do not understand this like mutual alignment with buyers and the mutual triggers that are happening, and they stop short in getting the information that they need to know how to sell to them.

First of all, should they be selling to them? Should they be prioritizing them? You know, is there going to be successful close and a successful customer, which in startups, you got to create a flywheel, right? You sell it to the wrong person that could cost you.

Rachel: Yep.

Walter: Way more than any revenue that you get. And they need to get the information to know if it's a good fit to prioritize them, and how to then drive the deal to close while maintaining a high price as well as accelerating the sales cycle.

And what happens is, if you're using AI and you're not asking the hard questions and you're not finding a way to communicate both with your words and your way of being, that you are mutually aligned and that it's safe for them to open up, you're not going to get the information you need.

So you might have a fancy AI model, AI workflow, a bunch of SaaS products, but garbage in, garbage out. So that's where I think AI by itself is really good, but it's not good enough.

It really takes the founder to find a way to open up the prospect, the buyer, to give you quality information so that you can really leverage AI to the fullest, to both increase the chance that you're going to close the account, as well as that you can collaborate with the buyer to get mutual success, which then feeds the founder-led sales flywheel.

Rachel: Let's bring it even closer to home. You and I, I as an investor, you as a coach, live or die on being able to help other people become successful. What happens to us in the age of generative AI? What happens to our coaching practice?

Walter: It's such a great question. I remember on Facebook, all my smartest geekiest friends were commenting like, I don't think the world knows what breakthroughs have been happening in AI.

And I actually, for like a week or two, just heard those. And I'm like, whatever. And then I got into ChatGPT, and I was floored.

Rachel: Mhm.

Walter: And I both had the sheer, oh my gosh, this is going to replace me. And then I was like, oh, how do I, you know, have 10 years of revenue in the next year from it? And it was both concerning and thrilling and it continues to be.

Rachel: Mhm, yeah.

Walter: And I spent six months where every waking moment that I wasn't working with clients was playing with AI, learning the language.

Rachel: Yeah.

Walter: Learning it in different worlds, you know, working with a client and then trying to do it but with AI, because then I could test, you know, you had like the high end, high touch outcome and then what's the one with AI? And seeing how I had to change my mind, how I was thinking, to really learn how to collaborate with AI.

And there's a lot that it can do that makes what I do, potentially a commodity. But I believe since everyone isn't as into AI, and you know, when you look at it like first time managers suck always.

Rachel: Yes.

Walter: Using AI, you become a manager.

Rachel: Yeah.

Walter: And there's going to be some, a good amount of time that people are just going to suck at it. So I think being a coach and using AI, you're going to get, you know, you're going to accelerate how much impact you have, how much money you can make, but also it's like being a manager, you know, first you manage one person or a team, and every time there's a challenge and people are going to need help with that.

So I think, you know, a sales coach, you know, might go from teaching people how to sell, and then in my case, also teaching them how to not be in fight or flight while selling.

Rachel: Yep.

Walter: And then how to increasingly use AI to sell. And then at some point how to use, and this is happening very fast, how to use AI to coach the rest of the people at your organization.

And so coaching, you know, one person and going through all this discovery and kind of figuring out the model, you might charge 10 times more for that, but then help implement AI to then scale that across the entire organization and at each growth stage.

So I think if you really focus on value, and if there's anything that I teach my founders in founder sales coaching is you don't even talk about price really. You talk about value.

So I think as a coach, there's still years to leverage AI and what you do and then help your clients leverage AI to need you less in the ways that they needed you before, but then there's new ways they need you and then you just charge a lot more. And I honestly believe that you're going to need to work a lot less and the time that you're working is going to be a lot more creative as a coach.

And, you know, already, I go walking every morning for an hour. I use ChatGPT audio, you know, my, I have a hurt thumb because I have, you have to press down the button and I hope they figure that out to where you can like press once and release.

I kind of now use otter.ai because you can do that. And then I export it to ChatGPT mobile. But I spend an hour just talking back and forth to it. And I can review calls, I can ask the call transcript questions, I can come up with, you know, I help companies take their sales deck and make it a collaboration deck, which is great for founder lead sales.

Increasingly I'm doing that with AI, so like I could literally be hiking in the morning and take a few calls, transcripts and come out of it with a fully customized, using my template collaboration deck. And that used to take me a day or a couple of days. Now it's one day or it's one hour.

And then you can do like, instead of one big rep, you could do, or a few reps, you could do 30 reps a week. And so the value of it that it's going to create is far more. So it's just, I think for coaches, it's just keeping tied to the value that one creates unlinking from time, and, you know, realizing that people, oftentimes, there's some people that are never going to be good at managing, some people are going to be great at it with the right training.

And it's like, how do you help bridge that? How do you help people be good at managing AI and what they do? And they're going to replace some of the things that you do for them, and that's okay. You just keep going up the stack.

Rachel: One of the reasons I loved learning sales with you is that you never shied away from how painful it is with all of the exposure to rejection. Can AI suffer enough to get good at sales in that way?

Walter: You know, I went for a run earlier today, and I read your questions and this was one of them, and I was trying to come up with a good answer. And it was like suffering from a founder, giving it crap data and being like, "AI, how do I sell to this person?"

And the AI is going to be like, I've said this a million times, you need to get the answer to the three why's. Why buy anything, why buy us, why buy now with a champion and a sponsor? And you haven't got any of that. You gave them information, you know?

So I think if AI has patience and if AI has pride in its work, I think it's going to be quite suffering until founders when they're selling, really learn that it's not about giving information in meetings, but it's about getting it.

Rachel: More seriously, how might we smooth the handoff from automated systems to authentic human communications? You know, that there's tons of these AI tools now out prospecting on LinkedIn, you've probably seen as many as I do, and some of them are convincing for one or two turns of conversation and then obviously a machine.

How can we make it easier on both parties, the buyer and the seller, when the machine hands you off to a real customer service rep?

Walter: Yeah, it's really fascinating. When I started using AI, you know, you'd first have an idea and then you would have to refine it and then come up with the next idea. And after you do that a bunch, you have the great idea of like, wait a minute, how about I ask it what's the next best idea given my initial idea?

How about I ask it, given my purpose, my goal, what should be the next step? And it's like you start to ask the AI to do a lot more, and then it's almost like you're in flow and just amazed.

So I think using AI to do automated outreach is basic. I think it might work if it's a numbers game for you. I think it might work if you have a really good understanding of your ICP and a really good value proposition.

Where I see the AI going is, you know, when I work with people, I have what I call a in no risk session where if they're qualified, come from a good reference, maybe we talk for 30 minutes to see if it's a good fit.

I will do a session with them so they can experience my work and what I do. In the perfect case, they don't know pricing yet, so that when they hear pricing, and usually people get a little bit upset, you know, if they don't get upset, you're not pricing right. Right? And then you can just point to the value that'd be in the no risk session.

Rachel: Mhm.

Walter: And you know, in that session we take, you know, my templates and my principles and we apply it specifically to them as a person, their nervous system as well as their company, their market.

And I think with AI, a lot of that can be done before I even meet with them, that a lot of the value that they can get can be experienced before they actually have time with me. And it might even convince them to spend time with me. It might even convince them to reply to me.

So where some people think AI, you know, for volume, I'm thinking AI where you can actually add great value before you even talk. And so from the get go, you're collaborating and then it's, you don't even use a AI bot for communication.

It gets replied-- I'm being a little bit cryptic because I am working on something that takes what I do in the first week and delivers 90% of that before any connection. And that they could take that value and get value from it. And that's what's going to get them to want to work with me.

I'm working with a product manager right now in Brazil to kind of get the first version going. But that's just another way of saying, I think the handoff to AI is how do you make the buyer journey a lot more human? How do you make it a lot more collaborative?

And there's going to be a lot less spray and pray. There's going to be a lot less kind of fooling like, hey, I thought you were a human and it's going to be like, wow, you see me.

Rachel: Mm.

Walter: You know, the buyer's going to be like, wow, you see me and wow, you came just at the right time and I was actually, you know, thinking I needed to do this thing. And then they use and experience it and they're like, wow.

And then that's the first experience they have of you, your brand, your company. That's where I think the more human collaboration with AI in the sales top of funnels is going to look like.

Rachel: I love that. I love how you always come back to the idea of collaboration because the way you structure these interactions, it's not a zero sum game. You're looking for the win-win outcome where both parties walk away from the table with value. It was so empowering for me to enter into that paradigm.

Walter: Thank you, thank you. And you know, here's something that's maybe a little weird, maybe I shouldn't be saying this on a public podcast, but really quickly when, you know, you had asked a question about, you know, what about AI replacing us?

When I coach people, and I've been through, when I was 33, I almost got married and I went to therapy and I realized we weren't right for each other, that I was completely in my head my whole life and I didn't feel my body. I wasn't connected to my gut mostly, usually. And that started a decade or two of therapy, coaching, all kinds of things, you know, healing psychedelics.

And I've developed over time the ability when I'm talking to a founder, to actually feel in my body when they're experiencing a blockage where there's like a self-limiting belief that's getting in the way of them to apply first principles, right?

You know, like you get information, you don't give it, you know, until you got it. You control time in a way that efficiently is going to get to a shared, you know, mutual success. When they're not operating like that and I can get a sense for when there is a self limiting belief that's preventing that and it's like a gag system in my body.

Like, hold on a second, let's slow down. And it's like giving it space and giving it presence to allow them to start to go from their head into their body and have them experience the body being able to stay open and that kind of pressure and that kind of uncertainty and under those conditions where those self-limiting beliefs kind of come up and it allows them to see themselves more clearly. And the moment they do, I usually get this rush of not chickenpox... goosebumps!

Rachel: Goosebumps, not chickenpox.

Walter: Not chickenpox, I'm on a podcast, right? So I'm a little bit, you know, fight or flight and I get this.

And so I use my body to kind of judge, should I move on? Or, you know, in every session there's like one situation that's going to identify that the biggest self limiting belief that's below the surface, that everyone always lies to me at least three times about it.

But because I feel it in my body, I could actually slow down and give it presence and my nervous system gets very resourced. It allows them to go from closed to kind of open to opening and they can see it and they have a chance to then see it, to see that the self-limiting belief doesn't serve them. That it was probably something from childhood, that the truth is different.

And when they align with that new truth, they're able to then do the things. And so can AI feel? Does it have a body, you know? And I'm sure using like some words and some patterns of things, it might be at some point, but when I'm coaching someone, it's just like, oh, I want to gag. Hold on, let's go right here.

And it's like the gold mine of where the energy is leaking from the founder, you know, where they're like, I hate sales. And it's like, no, they don't hate sales. They hate feeling the way they feel when they're in certain contexts and that self-limiting belief starts to bump up and they start to like prime information, they close, and they're no longer connected to all their resources.

Rachel: Mm.

Walter: So the reason why I'm saying all this is because you asked about AI and if it was going to replace us. I think things like that are going to become much more important in coaching. And I think people having presence and staying open is going to become much more important in their jobs.

You know, before AI, there's a lot of constraints. With AI, there's going to be so much abundance. There's going to be so many different things that people are going to buy and people who are so-- Like I love therapy, I love healing, I love transformation. Like, I love the fact that I can kind of feel the gag and then the release and hold space for people. And that I actually like it, that I love it.

Rachel: Hmm.

Walter: And I think people are going to start to tune more and more and they're no longer going to have to do the drudgery, but they're going to find what kind of finely tuned instrument are they and do they want to be? And then how they can use AI to do less of the other things.

And so that's my example of it. And I think everyone has something like that.

Rachel: That's such a gorgeous framing. And when you think of the amount of energy and the amount of resources we pour into one of these large language models just to get it to write at the level of a college sophomore, it really illustrates in very quantitative terms how much we process in our brain and in our gut and in our nervous system where exquisitely powerful information processes in our bodies, much more so than the LLMs are.

And I love your vision for letting people unlock that and letting people be present with it and learn to let their energy flow.

Walter: Thank you. You totally got it. The mind, the body, the heart, the gut. That's what's been constrained in the past and the constraints are being released and it's like, you know in a startup it's like you could spend a whole quarter, all nighters getting something done, building something, and if it's the wrong thing, it was all wasted.

You're further back because you've lost time, you've lost money, right? And when you have the space to be fully connected, you start to say no more to things that aren't aligned with you, your company, and the market, and the world.

And you have this space and time and focus to say yes. And so I think people who are fully aligned with what they're selling, the problems that they're solving, the transformation that they're aiming to provide, those are the people that are going to be the best sellers.

Rachel: Yeah.

Walter: And even if an LLM's like here's the right thing, it's like being in the room with someone and feeling them and it's like, okay, we're going to go together down this path of transformation. That's what people are going to be buying.

Rachel: Yeah.

Walter: And that's why when I teach people founder-led sales, the first thing I do is I teach them that they already know like 90 to 99% of what they need to know in sales. Like the skillsets, right? The experiences of being compassionate.

You know, founders want to end suffering. They want to change the world. Curious, founders are always curious, learning stuff and collaborative, right? Founders are collaborative. That they already have these skills, but what they lack is knowing that these skills and experiences map to what it takes to sell.

Rachel: Since we're talking about trauma, what connections might there be between the loss and grief we all suffered during the pandemic and this sudden urge on the part of a large part of society to just replace human jobs with artificial intelligence?

Walter: I think with Covid and being away from everyone, it's far easier to be in fight or flight. Especially when people made decisions about working remote and then now they got to come in. Distrust. Both managers, distrusting their team, are they working?

If I don't micromanage, you know, people who are being managed, you know, like, hey, I want the space. I'm a professional. You don't trust me. I think there is a lot of like closeness and I think it's easy to objectify people that you don't see face-to-face.

You might see them in Zoom, but the mind kind of just, it's not the same thing as feeling someone in presence. So if people are losing their jobs now because of AI, I think that's a part of it.

What I think is going to happen is as people get over the initial fear, those that get over the initial fear, they're going to be able to go further faster. So I think it might slow down growing teams, but I think if the team is full of great people, the team's going to do far more. And so I don't think there's going to be a lot of job losses, but we'll see.

Rachel: Yeah. Other than directly playing with GPT-4 and running all of these amazing experiments, what is your favorite source for learning about AI?

Walter: So I watch everything I can on YouTube and there's like the news, like Matt Wolfe has a good podcast, listening to the leaders of the companies. My latest favorite is the CEO of Perplexity. You know, he's new to the spotlight I think. And so he gives a lot more information and a lot more personal opinions than most.

And I think he's got the best first principles that I've heard. The way he's looking at what he's doing, what other people are doing and why, really helps me get a sense for what are the true problems being solved now? What are hard problems that aren't going to be solved?

And so I love watching podcasts with him each day. The last couple days I've been watching whatever I can find. Also, I can't stress enough, it's like some people will use ChatGPT and other things to find out how to do things they couldn't do before. And I do that.

But what I love to do is try to use it to do the things I know how to do so I can see where it's good and where it's not.

Rachel: Mhm, yep.

Walter: That's the best thing. And then how can I use it to then have world babies, right? So I'm like, okay, founder-led sells. Okay, now how do I connect that with product management? What are the two frameworks from each of them? And then I do that.

And so those are my favorite ways to learn at the moment.

Rachel: I love that. I call it The Economist test. The Economist always sounds so authoritative and you just believe everything it says until you read an article about a domain that you're a deep expert in, and then you're like, wait, no, I can see why you would think that. But that's an oversimplification.

That's where you really learn what it is they're doing and where their level of abstraction is. The same is true with these new tools. Until you test it in something that you're really good at, you can't see what their limitations are.

Walter: Exactly. My other favorite thing to do is whenever I meet people or I'm talking to people I love, I ask them, are you using ChatGPT? And some of them are like, no, this doesn't really fit my thing. I'm like, all right, download it right now. And I'll sit there and I'll pretend like I'm them. And I'm like, okay, what is a use case?

You know, I did this latest with my chiropractor and it took two seconds for him to be like, oh my gosh. And boom, he was now, you know, AI native, applying it to being a chiropractor, you know like.

Rachel: What was the use case?

Walter: So after every session it's like, okay, so what should I do? How do I heal faster? How do I strengthen this? And he shows me and I'm like, you know, I take a picture of the moves or I do the video and you know, I try to write it down and my compliance is not as good, right?

Only when I'm in super pain and I have done this, I have watched the videos and such, but with this, he can both record the session and then at the end say, okay, what you should do is, you know, this, many of this move a week and do this. And then boom, you got a table and you have what they should do, how many, a description, and then links to, you know, places.

And right now the initial version is just, you know, random stuff on the internet that has the same name of the move. But he could do a custom GPT and have it linked to a library of his moves.

Rachel: And he could integrate that with motion and have it just drop into his client's calendars. So that Monday, Wednesday, Friday he's doing these exercises.

Walter: Exactly right? It's endless. And so, and then once he got that, he then was like, wow, this is amazing. He then started making songs for his wife.

Rachel: Oh wow.

Walter: And then I was like, hey, did you know suno.com? You can actually make real songs out of it. And I made one for him and I sent it to him. And then all of a sudden for the next three days, I kept on getting to all these songs about all his friends.

And so the best way to learn about it is to teach other people in different worlds and kind of think through their world and then create it, you know, to satisfy my needs. I'm like, okay, based on our session today, speak out loud what the plan is.

And I did it and I said, I sent it to ChatGPT and I said, make a plan for me that does it. And it did it. And so it's just like playing around in different worlds and then watching other people what they then go and do once they've learned this.

That has helped me a lot understand, you know, how long is it going to take for people to adopt it? You know, how well are they going to adopt it? And what kind of learning experience do they need to then run with it? And then to teach me new use cases.

Rachel: That is a great answer. Now I've got goosebumps.

Walter: Thank you.

Rachel: Walter, if everything goes exactly how you'd like it to for the next five years, what does our future look like?

Walter:

Our future looks like people being more connected and open in terms of their mind, their body, their heart, and their gut. They're more aligned with what they're working on and the constraints that they had are gone. And so they can work wherever, whenever, probably an hour a day if they love what they do. And there's going to be a lot more space in our lives to be with the people we love.

Rachel: That sounds absolutely beautiful. If you had a colony ship to the stars, what would you name it?

Walter: Starship Unknown.

Rachel: Oh, that's lovely.

Walter: Yeah, I can never under describe both the challenges and the thrills of exploring the unknown.

You know, I'm a founder, I work with founders. At the edge of the known and the unknown is where all the riches are, both in terms of new markets and innovation, but also knowing ourselves and getting to know ourselves and growing that edge.

So that's what I'm naming the starship after is just the unknown.

Rachel: Walter Roth, I love talking to you. This has been so wonderful. Thank you for coming on the show.

Walter: Thank you so much. It's always a pleasure.