For the first episode we have Ryan Williams. You can find him on LinkedIn at /jryanwilliams. Ryan is the Co-Founder of Churro Media and producer for a documentary “Outside the Valley” which can be found at outsidethevalley.tv and executive coach at jryan.coach. Where he coaches executives, emerging leaders and veterans transitioning into civil workforce. Before all of this he has seen the journey of 0-100 million 3 times as an advisor and operator.
In this conversation we cover how he started Churro Media and film his documentary. What 3 things come from writing out your sales process, becoming an expert, advice for sales reps, and thoughts on the upcoming year. This show has a little of everything for everyone and I hope you enjoy it.
Let us know what was your favorite quote or lesson from this episode? Please let us know in the comments!
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Show notes and Transcripts
Click show more to see full details.
Why starting Churro Media and the story behind the documentary, “Outside the Valley” [:50]
Ryan sharing how talking to Founders outside of the USA was the catalyst to Churro Media [5:50]
Observations from working internationally and effects of COVID-19 on fundraising [8:57]
How VC’s are approaching this time between early stage vs late stage bets [10:20]
Vintage of Startups that will come from COVID-19 [11:20]
Ryan’s background in advising and VP of Sales : [13:30]
Why you should write out your sells process [15:05]
What does your buyer say when you are not in the room? [16:05]
How writing your sales process allows you to create experiments as a Founder [16:56]
Advice for sales reps to stand out [17:30]
How writing out your sales process helps you identify what type of rep you should hire [18:20]
How writing out your sales process as a rep prepares you for running your book as a entrepreneur [19:25]
Why finding pattern matching matters [20:30]
What it takes to become an expert [23:55]
How it applies as a sales rep [25:00]
Examples of meta questions that Ryan coaches on [28:38]
Ryan ties meta questions with a story about a big career decision and an observation by his wife. [29:42]
How Ryan created his perfect day [31:00]
Questions to answer to optimize for the best experience [34:40]
Interview questions to ask to identify fit [35:00]
A question that reveals bias and reveals what people care about – [36:00]
Message for the listeners [37:45]
Outliers Guns and Ammo Magazine
Walter: Ryan, welcome to the show.
Ryan: Thank you.
Walter: Great to talk to you.
Ryan: As always.
Walter: As always. Well, Ryan, super excited to have you on as the first show. And we’ve known each other for close to what, five, six years now. And a lot of conversations that we have. It’s been that long. So excited to now record one of these. So with that kind of you know intro, I want to hear more on why did you end up starting Cero Media?
Ryan: The story’s actually really funny, I guess. But the easiest way to frame it is I had no idea what I was getting into when I said, I wanted to become keynote speaker. And so I just kept volunteering for opportunities to speak. And mostly this is around startups, how do I help startups. At the time, I was VP of sales at Lead Genius, an YC back Data Company. And I was just putting myself out there as let me see how I could be helpful. And, a lot of that it was doing sales talks. That led to a really interesting experience at 500 startups where they have the smaller accelerator programs around the world. And so they asked me to go to Kobe, Japan and do two talks, that kickoff keynote, and then close down the first week, and do a reflection experience and do like a closing keynote for that week. And I was giving that talk, things were going what I would consider well, as a speaker. I was feeling like I found my flow, I looked up and the translator looked like she was gonna kill me because I was talking too fast. I was cursing which was not acceptable. Or not advised. And I got to the end, and the guy who is running this accelerator pulled me aside on the way out, I thought this is it. This is the talk from the principle, hey, you’re never doing this, again. Your keynote sucked and stop cursing to a Japanese audience. And Max is his name, he pulled me aside. He said, Hey, that was great. Can you meet me in Uruguay and do the same talk in six weeks? And I was like, Holy smokes. All right. So I was like, great, happy to do it. I had to look up Uruguay on a map by the way, I had no idea where that was. I thought it was like it rounded Paraguay, whatever. I’ll look it up. And so I’m headed back to the airport to leave this trip from Kobe. And I’m realizing, oh, wow, what I’m doing is actually really valuable specifically to founders that are outside Silicon Valley. And that one talk led to now what’s been 20 events at accelerators around the world in 14 countries. I’ve met probably 2, 3000 founders. The largest talk I gave was a follow up to that Uruguay experience. I gave a talk to 750 people in Uruguay. So like the, I want to be a keynote speaker idea, that work that stuck. And along the way, I reconnected with a close friend from college Hannah Wicks. And Hannah has seven films that have gone on to be Netflix sized documentary hits. And I was telling her what I was doing. And we actually cross paths in Italy on my way to Istanbul for another startup talk. And so when we cross paths, she just said, hey, you know, there’s something really interesting here about why these companies are having you come out and speak in these, what we call ecosystems, right? These group of startups in Istanbul, these group of startups in Buenos Aires, these accelerators, these events. And that led to a development project where we went to four cities, filming about the city. And we even shot a pilot for more of a reality TV series that went nowhere. But it all led to a process of saying what we’re doing here is actually telling stories of founders from around the world. And we just finished our first feature documentary. And so Cero Media is the holding company that now has two media projects that you’ll see a little more coming out this week as the trailer for our first feature film called Outside the Valley, the early years. And it’s about early stage founders in Portugal, in Uruguay, in Mexico City where you’ll meet Andy and Maka, who are basically bringing e commerce. You know that e commerce is a space has had a 20 year head start, but it’s still fairly new in Mexico. And then we end that story in New Zealand just before the Coronavirus stops us from getting into our fifth city. And so that’s the first media property. The second is a docu series called Future. It’s also powered by Uruguay because actually in Uruguay, we made the connections of folks who want to tell more of their stories of the software that’s being developed in Uruguay and going all around the world including using for facial recognition in Africa to identify lions. Lions have unique whisker patterns. And so we’re finding all these amazing stories about technology and software and startups and founders. And we’re putting all that together in what’s best to describe is like one channel, you know. It hasn’t emerged as a channel yet, but the people who join this community are going to see stories from around the world. And that’s really what Cero Media is about. Did I answer your question?
Walter: You did.
Ryan: It felt like I gave you a long answer, but that’s what happened.
Walter: Yeah. But that’s the nice part about this, is that your poster, you know, go off and font format, so feel free to speak. It sounds like quite the adventure. And a lot of time and energy went into it. Like why are you doing this? Like, what itch is that scratching for you?
Ryan: Well, there’s a couple things, right. One is, this work. As I’ve met these founders, the work of telling their stories is an absolute love letter. The amount of grit and determination that happens for founders that are outside Silicon Valley is so impressive, because you sometimes have founders who are running a company in their second or their third language, they’re not getting advice and podcasts and the way that we consume material in our startups, or sales process or growth strategy or fundraising, you know? Think about all the challenges, right, it’s easier to raise money, when you have a similar background to the person who’s giving that money out, because there’s less object from. But if you have an accent, or you’re from somewhere else, or you look differently, or you’re a different gender than the person who’s writing the cheque, it gets harder. And there’s lots of studies that proves how hard it is to fundraise, which is one of the first basic things. Like knowing that you’re a technology company means that you’re using tech as your lever for growth and success. You know, that’s why we call it disruption, right? It’s because tech is that lever. And a lot of times to be able to use that tech to be able develop that tech, you need to raise money. Fundraising is not something that everybody around the world can just go turn on the way that if you know went to high school in Palo Alto, you probably have somebody in your social network, who’s gone the venture route, or gone the early stage and, you know, Yahoo or whatever, you know, company, depending on your generation, and they know somebody who wrote the cheque, or can write the cheque, read an angel cheque. Having angels in these communities, it’s hard too. And so for us, what we’re really excited about is just you know, the love of that founder, that person who’s going out there staking, going on the way they’re you know, they’re burning the boats, they’re going all in and to be able to kind of give that founder a voice and share that. What we’re finding is that there’s a lot of people who want to hear that story, because they’re on the fence thinking about their next thing, right? They’re thinking I’m about ready to jump in, which is funny, because that’s actually my co-founder, I met in college, doing a college project. And he went off into the startup entrepreneurial route. And, several times had invited me to join him. And I always considered it a regret for not doing that, you know, and here we are almost 20 years later, back to the well, this turned in from let’s do a short film project, just released to my audience around sales and coaching too. There’s actually a much wider audience than they want to see some stuff. You know, along the way, you get to see me, you know, fall off a scooter and, you know, meet somewhere and talk to some locals about what makes their coffee different and things like that. And that’s really the fun stuff that makes telling the stories so much fun.
Walter: Yeah, no, it’s very interesting. I think also with the COVID pandemic, and people working from home disruption from that, it’s probably going to level the field in a lot of different ways. When talking with all these international founders, what are their thoughts? And what are your observations?
Ryan: Well, fundraising is you know, they say that fundraising has not flattened off with the pandemic in the way that people thought it would back in March. People thought, Okay, this is gonna be really hard to get a cheque. The thing about the VC economics is that the money is already there. And so some early stage VCs are sitting on it, saying, hey, I’m gonna wait till startups get cheaper, you know, so my friends that do early stage, kind of pre series A cheques, cheques that are usually 100 to 200 K, less than a million dollars, those folks are kind of playing a waiting game to see who’s gonna survive this because that shows enough grit that they can then invest. The next stage up to series A and Series B, those are funds that already have money in them. The LPS have already had capital call, there’s money in those coffers. And so then it’s a question of, how do we keep our management fees alive if you’re a VC, and if you need to, then you want to keep your pipeline going, you’re taking those calls, you’re doing over zoom. And it’s easier because you know, the way you get to know the founder is a little bit different. You know, you’re able to like, you know, sense, you know, do a call, get a sense of them, be in their life, I’m sure. I mean, I’m sure you’ve seen all the zoom calls, it means that you get to see inside people’s offices and homes, things…
Ryan: And see how they manage their life, see, if they’re like, let me put you on mute. And then you hear them, you know, you can see them invisible yelling at their children to get. You can see all that stuff, you embrace that. But what I’ve also heard is that a lot of the fundraising not slowing down statement is, there’s a lot of late stage, you know, we’re going to use that money to make a bet that we already have the rest. And, I think that’s really interesting in that it still may be hard to get some of that early stuff done even though we say it’s getting easier, you can do it from all the way around the world. Zoom calls, people will know you change your background, people will know where you are. And so you can tell them that, you know, we’re running this company out of Palo Alto. Right now, you’d probably think that’s pretty silly, based on the price per square foot in Palo Alto. They’d like you to say, you know, Denver or Tulsa, you know, or somewhere else, that’s a little more cost efficient than San Francisco or the valley. So it’s interesting, it’ll be you know, I hope that what happens, you know, a lot of folks on the investment side talk about startups as vintages. You know, there’s a vintage of startups that we’re all trying to be like Groupon, they all show up at the same time, because the problems are the same.
Ryan: It’s not that everybody followed Groupon, there’s few that followed Groupon but the problems that were being solved like box and Dropbox, you know? They started a couple years apart, but they had the same origin stories where, you know, we’re in the dorm room, or we’re, you know, in our first job, and we don’t like using thumb drives or emailing stuff to ourselves, the stories are the same from about the same era. And so I’m just worried that COVID is going to show us that there’s a vintage ticket made. One of the, you know a wine producer that I absolutely love that I can barely afford, just sent out an email and said, hey, you know, our grapes, they survived the fire, but this, you know, they were too close to the heat. So we were not going to make our vintage because it’s not gonna be as good. And so why is there a vintage where some people are deciding that because of the fires in 2020, they’re not doing it? And I think there’s a lot of startups that will not survive this. And then there’s a lot of folks who are happy in their corporate jobs, they’re investing so options for companies that are doing well, there’s a lot of virtual companies that are doing well. And, then they’re going to be able to start their thing in early 2021. That’s where we’re gonna see a lot of innovative seed stage companies coming. And, they won’t necessarily launch it early 2021, that it might be to the summertime that you start to hear about their launch. But they will raise a small cheque, they’ll raise 100 200 K, or whatever they need. And that’s where interesting stuffs gonna happen.
Walter: Now, that’s going to be really interesting on what’s going to be some of the rippling effects of COVID. And thinking about also the economy, and especially within the VC world. So getting into the original reason why you started doing this is being a keynote speaker for sales, you have done three times, three companies YC Bank, zero to 100 million, when you’re now looking at all these different things, what are some things that you’re thinking about as far as go to market fit, how to grow? What are your advisement on how companies should be doing that in today’s market?
Ryan: Well, I think there’s two pockets of advice, right? There’s an advice to the founder and the startup. And, you know, thinking about it and preparing for this conversation, you know, I’ve had the fortune of seeing as a coach, I’ve seen the 50 to 150 million journey working with high growth, high potential sales leaders, the director of midmarket, head of SMB sales at companies that already have some great traction and some you know, amazing growth metrics. And I’ve also seen at the founder stage as an advisor, I was an advisor to a company called Envision back when they’re about 10 employees. They are around 2000 employees now, they work with every one of the Fortune 100. And so I’ve seen the founder trying to go and make that first sale. And then I lived it at Admiral when I was, you know, the first sales manager, I built a $22 million sales team or a $58 million sales team in 22 months, and had a chance to work with around 250 sales reps, and SDRs over the course of my four and a half, almost five years there. And so I got to see how to sell myself into that world and then what happens when the company takes off. And I’ll tell you that across the board, there are some very fundamental things that just have to exist for companies to get it right. That is, knowing what you’re doing, knowing how you sell. And so anybody listening to this who doesn’t have a written out sales process, stop right now and write out your sales process. And then take a different color pen and go right underneath it, what the buyer is doing in every one of those steps. So when you get to the third step and you know, like, let’s say your sales process, step three is doing a demo for your buyer, and that buyer is boss, let’s say, I expect there to be two or three people on the call, I’m going to demo the software, here’s what. On the third step might be internally, they’ve got to go ask their boss, Hey, can you join this call? What is that conversation look like when you’re not in the room? When your buyer is turned around and saying to somebody else, hey, it’s really important that you sit on this demo, because I need to buy this event management software for the event that we’re doing in March. Okay, what’s going on at that stage? What’s that conversation look like? I don’t really want to do this. Or great. Can you expose me to all these? I want to actually I want to hear from three vendors. Like what is that boss ask for? And then if it is, I want to hear from three vendors. Your sales process might be doing a demo, and then the next week, you’re asking for the order. Well, that’s great that you think you’re asking for the order on the next week. But there’s process might be to interview two other companies with the same questions that you gave them. As you showed your demo, they took notes. And they said, All right, and they ask all your competitors to rebuttal. What do you do about this feature? What do you do about security and the things that you think are the best points of your sales process. And so by writing your process out means two things, one, you’ve written it out so you can be intentional. Three things really two, you’ve written it out so you can think about what your buyer is doing. And three, you’ve written it out so there’s a line in the sand for your experiment. If the last five conversations you had all of them went to demo, and foreman went dark, well, either you have a 20% conversion rate from demo to the next stage, it might be negotiation, or that major drop off has shown you that your message is not working four out of five times. Which is it? I don’t know. But you’re not going to know either unless you’re documenting or writing some of this stuff down. Right. So I think that’s advice one, and that goes both ways. That’s both the founder who’s starting to sell for the first time, they’re going to use that same process to identify what sales rep they should hire. They do the same process we just talked about. And they discover that, you know, the demo is not that important. Because the demos are fairly easy. And then it’s a matter of waiting for time. And they know they’re going to win against the competitors. And it’s the story that I just made up. Well, great. Now they know that they don’t have to hire somebody who’s really adept at giving demos. If the reverse is true, they’re losing four out of five demos. They need to hire somebody who’s got more credibility, they might save up and spend more money on hiring a sales rep account executive or somebody who’s slightly more senior, who has experience doing that type of sales process. This morning, I started my day talking to a, you know, brilliant sales leader who has previous experience selling billion dollar deals. Walter, how many people do you know that can say that they sold something for over 100 million?
Walter: I would say right now…,
Ryan: Do you know anybody?
Walter: No body. Not the top of my head.
Ryan: Right? So same here, right? So this dude worked on a billion dollar deal, it was a three year deal selling something to the government. And I won’t get into specifics, but you know, he’s basically it was a piece of hardware that helps for monitoring logistics.
Ryan: You know, you need to ship some containers around, you need to monitor them, who’s got a bunch of containers moving around? Well the government has one of the biggest logistics operations, you know, the US government does.
Ryan: And so, you need to track all those containers. Let’s just, you know, keep it like that. And so anyway, but you know, okay, these are really big engagements. This is somebody who have you said, hey, how do I optimize my sales process? And what you’re selling is maybe an ad on Yelp, 300 bucks to a single decision maker one call close, you know, they’re just, it’s just a different world, right? And so if you’re somebody who doesn’t have a sales process right now, other than what’s in your CRM, if you write it yourself, and you make some of those assumptions, then you can also see what type of rep you are. I’m really comfortable at a 30 day sales cycle anything past 30 days, I usually lose. Is that because of me as a rep, is it because the product I’m selling? Well, let’s have that same data, and any sales rep who’s brought that kind of data in to me, and when I was a hiring manager, always is going to get more consideration for that job than anybody else. Because they’re showing me that they’ve got the skill of being able to do the job and the skill of being able to think about the job they’re doing. The founders usually have that because they’re constantly thinking about what they’re doing. They have these Meta conversations in their head that in some cases are just haunting. And it’s tough. It’s tough. They’ve got the hardest job in the room. But then you come down to you hear a sales rep who can do the same thing. Okay, man, you’re running your book as an entrepreneur. That’s really cool. That’s really interesting to me.
Walter: So they’re able to outline the selling journey, match it to the buyer journey and do experiments along the way. Outside of doing that, is there anything that you think that people are doing wrong today, they also should be focusing on?
Ryan: Well, finding patterns. So as humans, we always want to find patterns. You buy a white car, I bought a white Subaru when my first car it was actually the Subaru Legacy wagon. And the outback trim, I don’t know when the outback came out. It was a 97 legacy wagon, it was white, and it had just a gray paint job that made it the outback. It had gray paint, heated seats, and a weather radio. That’s what made it Outback. Since then, I think Subaru has gotten a little fancier about their Outback. So they’ve done some things in the trim. As soon as I bought that car, every other car I saw in the town I was living in was white. You drive a white car, you pattern matching, you see white cars. You go to Stanford, you see a bunch of other people who also went to Stanford, you’re an investor, you’re going to invest in people that you know, that went to Stanford, because that’s what you know, is pattern match. Now, there’s a lot of problems with that. But there’s also a lot of good that comes from being able to naturally match those patterns. And so the question that I have for a sales rep who’s trying to, you know, trying to get ahead, and you know, and founders too, but I think founders are going to do this naturally. But salespeople need to do that same pattern matching of the last five deals I want, what do they have in common? Can you tell the background that my zoom school is not going that? Well, it must be recess time or lunch because they are going nuts upstairs right now. So I hope it’s not killing your audio.
Walter: It’ll be fine.
Ryan: But, you know, they’re having fun, at least, you know, I hope they look at this is the year of their life that they got…
Walter: Online school.
Ryan: Yeah, absolutely. So let’s talk a little more about this pattern matching thing. So I want to give a quick shout out to old friend long time ago worked with this woman named Megan. And she made an effort at Admiral to sell all of the high fashion companies in London. And she was really into things like handbags, the stuff I don’t know a lot about, but she made it a point to talk to all of these independent designers who had ecommerce stores. And she had a very tight aperture tight view of this is what it means to be a fashion e commerce in the UK right now. And that was Intel we really needed. Somebody else at the same time also early on the Admiral team is a man named Ben Willy, and Ben was doing the same thing, but he was selling to a dead end market for us, but he was learning a ton about selling it into India. And so he had talked to you know, maybe 200 potential advertisers in India and gotten some of them too close. But he had developed enough of a pattern to understand the market India that he was getting called in from the CFO. And that job turned into a product management job. Now he’s a founder, he’s running a company called Recess which is a really cool breakout beverage from the last two years. It’s a CBD sparkling water type beverage. But because of this pattern matching he will be able to say okay, well, I tried the same thing 10 times, this is what I had in common. And sales reps who are looking for leadership opportunities, need to think about a way to do that where they become the expert in this market. You know, a lot of people are familiar with the advice that you know, takes 10,000 hours to be an expert. It comes from a research study that Malcolm Gladwell wrote about in the book Outliers.
Ryan: Well, I had a professor in school, Colin Campbell, who was one of my favorite professors. And he actually he gave us an assignment over break. He said, if you go home with a break, and you read every book that Edward Abbey wrote, Edward Abbey was a western US, writer, you know, probably 50s and 60s, I want to say. And if you read every one of Edward Abbey’s books, he wrote nine books, let’s say you only read eight of them. But you got an eight week break between Thanksgiving and New Year’s because we have this really long winter breaks at the college. And so if you went and read all of his books, you’d come back and you’d be the Edward Abbey expert for about 100 miles, except maybe there’s a professor who wrote his dissertation or her dissertation on Edward Abby. In which case you should probably choose another author. But his point was, it doesn’t take much to become an expert. Okay, now let’s go back to the sales rep advice. A sales rep selling hotel management software to the GM of a hotel, who hasn’t more than three weeks on the job, has looked at provisioning, guest experience software more times than any GM who works in any hotel. They’ve become the expert because they have seen this decision being made. Let’s call it eight times a week. You know, I’ve been market product that’s probably less than 10 grand, they’ve probably see this a few times a week, at least, right? Like, let’s get, let’s say eight or 10 times a week, right? So three weeks in, you’ve talked to 30 people who are at that same crux of decision on what they’re doing for guest experience software. And now you talk to a GM and you go, please, sir, can you consider the demo like you’re begging for it? Because you’re a new rep, you probably haven’t seen that first cheque yet. But truthfully, you’ve got enough of a pattern to be able to say, this is the trend. GMs on the cutting edge are doing this, GMs that are laggards that are waiting are doing this, they’re all looking at this and thinking, Okay, it’s too expensive, or it’s too desperate to that. You’re actually more of an expert as a sales rep than almost anybody else in the field. Yeah, sure. There are some people who are really true experts that built the technology wrote about it grad school, and now they’re running software companies. So yeah, you probably not going to like win a fight with a CTO, right? But if your buyer is not the CTO, or CTO is the buyer, but they’re buying something specific, you actually know a lot that you may or may not give yourself credit for. Right? So let’s go back to Megan. Right. Megan is selling into e commerce fashion brands in the UK. This is probably the year 2012. And she’s absolutely crushing it. And any one of those clients who would say to her, Hey, what is everybody else doing? She’s got a really strong opinion on what the best ecommerce fashion brands in 2012 are doing to get their handbags to the world from one specific market. She knows how they’re advertising, she knows what their other strategies are. And because she also likes that space, you can talk about what the designs are like and what makes them cool, what type of leathers are using etc. I don’t know that space you know, I don’t know anything about it. But if that’s the space that you’re passionate about, then Wow. So for anybody listening who’s on the sales rep side, as opposed to the founder side on the market, if you’re on the sales rep side, let’s go make sure you sell something in an area where you prospect by default. If you read guns and ammo magazine, you should probably go work for Sigur Glock. If you like to sit around and read, you know, Mother Jones, and you like to think about like how communities are managed and what cool opportunities are on local middle school and you’ve got on the PTA because you care so much about education, well, let’s go sell for K 12. And actually make that sales process better or I don’t know maybe, you know, companies like zoom or other people who have kind of had to pivot towards education during the pandemic, they’ve got a need for somebody who’s going to default and think about that space. You know, the guns and ammo reference is from a friend that I knew who was absolutely passionate about this space, and couldn’t figure out where to use his skill set. You know, regardless of how you feel about people who have that hobby, you know, he went and sold on behalf of a manufacturer into police departments, and is now every day is his perfect day. He absolutely loves his job, he loves the conversations he has the same way that you know, in 2012, somebody who’s selling you know, the handbag market in the UK is probably pretty thrilled about the type of fashion that’s coming out of the UK at that time. You know, it’s just a matter of finding those things, and then the pattern is going to match on its own. Just don’t forget, you’re an expert.
Walter: So what are those medic questions that a rep, a founder, even yourself, right, you went through and had as many questions? What are some of those for you?
Ryan: For me, I go back to when I talk to folks who are making a transition in their career. I asked them what they like about their day, what their best day had, what their worst day had. You know, I was recently in a coaching call with a director of sales at a big, you know, tech company that all of us know about. And we were talking through the things that make the day really good. You know, and some of his things were knowing that the meeting connects the purpose, and specifically where the purpose has to do with the team career management conversations. Okay, well, once you know that you like career management conversations, you can start to prioritize that on a grid. One of the product managers I worked with years ago, left to became a VC. They did what every young sales leader wants to have happen in a situation like that. He got his VC, wrote a cheque into a company turned around and called me and said, hey, these guys need a head of sales. You want your big break your shot? I said absolutely. So I went over I did a couple interviews. I got really excited about the company. And if you know me well, and you’ve heard my stories or listen to me on other podcasts, you know that I can’t go full hour without talking about my wife Jenny, who helped me make a lot of my career choices. So I come home from that meeting, the founder’s name is this guy named Alex. And he was building a really cool like analytics software over the gaming space. He had been a rising star engineer at EA or one of the other big game houses. And so he had built this cool analytics tool, and he had somebody go sell it. And so I came home. And I said, Jenny, this is what the job looks like. The job description, it’s a head of sales job with no sales people that work there. So my job is to go close the first 20 customers, try to get to a million dollars AR and then build the team. Now those are kind of magic numbers in software startups, right, especially at SAS. You get to a million bucks, and then you can start to build the team, because that’s really probably when the founder is going to raise series A, that use of proceeds from that four or five, maybe $10 million round is going to go into, you know, spend a million dollars on hiring a sales team. That’s not that crazy, you know, 10 people 100 k basis or whatever. And you’re off to the races with a million, 2 million dollar sales team from that race. And I lay this all out, she goes that sounds great. Except you don’t like to sell. You like to manage, you like career development, you like people. And how are you going to be able to get through this next year where you’re doing nothing but selling in a vacuum without a lot of people around with a busy CEO who can only come to some of your calls. And her point was like, you might not make it out of that kind of like that initial phase. I didn’t end up pursuing it. And I realized that it wasn’t a good fit. You know, that was the biggest reason, there are a couple of things that were quite right about that opportunity. But it changed the way that I looked at other jobs. And so I focus my effort on how to go create my perfect day at the job I had, which was, you know, the first sales manager that Ron that I built out that the number one big market team and later SDR and sales operations before we call it, I built that team up and then spun it off to the VP of ops. And I had a great time doing that for at least another maybe a year and a half after that first fork in the road, before starting to interview for VP of Sales jobs, knowing that I needed to be in a sales management. So I only looked at companies that already had at least five employees and sales, because then I could also evaluate the opportunity based on will my secret sauce, my special like, my magic skill is training. You know I started my career as an educator, I love to train, I love to talk, I love to mentor, love to coach. And because that’s my special skill, I need to find a role where there’s a team who needs that, where it’s one of my closest friends, the guy got me into sales was actually somebody who, you know, I don’t think is somebody who, yeah, he’s managed teams. But I think his skill is being able to sell anything, you know, these guys, right? You’ve got products like this, who could sell anything. I always make the number and sell anything. Well, you know, that person is going to evaluate that first time VP of sales in A series a pre-series a company a lot differently. They’re going to say, Oh, well actually, let me not go somewhere with a team, let me go somewhere where I don’t have to worry about whether or not Jimmy or Jeanine is taking time off today. Or I don’t have to worry about anything more than maybe one or two SDRs who are going to keep my pipeline full. And instead I can worry about who I’m going to close. And I’m going to go do that first million dollar deal. Or I’m going to do that first breakout enterprise deal, or I’m going to go like the friend I was telling you about who’s done billion dollar deals like, okay, somebody who’s worked on a billion dollar, multiyear deal, who understands what it takes to move out of the, you know, senior buyer is responsible for 100 million bucks to get to that person to go 10x that. Like you’re bringing all senior leaders into an operation.
Ryan: On an investment like that. And so that’s an org change project. That’s project management. Right? And I used to think like, why would you get an MBA and then go into sales? That doesn’t make sense. Sales are for people that don’t have graduate degrees? Well, sure enough, and then you start to see sales, it means a lot of different things to a lot of different people know.
Walter: And that’s, I think, what’s really interesting about sales. It’s not black or white, it’s like Shades of Grey. Well, I think it’s really interesting, if you think about this conversation is, in the beginning was as a founder, who are you going to hire and think about what they can do for your organization, like, what is it you’re selling? And then in reverse, asking yourself what are those questions and being able to ask those type of questions of what is your greatest day? Like, what does your best day of work look like, right? And you know, complementing those solutions.
Ryan: If you can answer that stuff for yourself, I think you’re going to be able to optimize for the right experience. And then if you’re interviewing somebody, how do you answer that in an interview? If you ask somebody what their perfect day is, they’re gonna say everything they read about on the job description.
Ryan: But if instead you can figure out what they liked or didn’t like about their last job. You know, I was just talking to a VC who asked me about one of my early experiences and he asked why that the company I was telling about wasn’t completely successful. And then I realized he was interviewing me, because he wanted to hear what my assessment was on the opportunity to find out if I was consistent with the way he thinks about his opportunities before he has me mentor and develop companies in his portfolio. And I realized, oh, that’s a really interesting way to say it. you know in that role, my mentor was Suresh Khanna, who is the director of sales for Google’s North America team before he took Adderall from about probably about eight or 10 million to 300 million or whatever the, you know, their published number was. I won’t speak out of school on that. But they were doing $750,000 a day, the day I left, right. So Suresh you know, really grew that team. Well, what was interesting about working for Suresh is he had this way of asking people he had been in kind of private. Well, I think you’d probably call it more like investment banking. But he does some BD stuff, and some investment banking stuff. And so he had talked to people about a lot of different types of businesses. And so he’d asked a sales rep, who maybe were at Morake for six months and say, tell me about how Morake makes money. Super open at it. Tell me about how they make money to hear what was interesting to the person that you start to get, you know, perfect day is one way to ask it. But asking how that company makes money is also going to reveal my bias of the things that are important to me. Oh, we make money by selling the shopping malls. Okay, well, then that means you’re in one segment, you know, or you understand a problem, we make money by selling to this IT problem. Or we make money because we like recurring subscriptions. Well, okay, then I know you’re interested in SAS, you’re interested in the way the SAS business model works. Which makes sense if you’re talking to somebody in Morake, great. He asked that question as somebody who sold solar panels, who was part of like a three part channel distribution chain.
Ryan: And went off the rails like this poor guy. He was like, can I get a marker and he went to the whiteboard and tried to explain it. And then he came back a week later to do it right because he’d been thinking about it all week, he ended up getting the job and he was great. I loved working with him. But it took him a while to get out of that hole. Because he was in a really complicated business, and opposed to saying, hey, look, I don’t know, but this is the thing that I do really well.
Ryan: That probably would have been a better answer for him.
Walter: Right. No, absolutely. Well, last question Ryan, what’s a message that you want to leave with people who are listening to this?
Ryan: I think it’s really easy especially right now to feel like other things, people, events control you. And I just don’t believe that’s true. And I don’t think it’s one of those booths trappy everybody can do anything they want. There’s a lot of limitations. There’s a lot of bias in this world, there’s a lot of things that are really hard to accomplish based on how the deck has been stacked against you or stacked for you. But I will say that if you approach your challenges with an openness to outcome, and knowing, hey, if I go do this experiment, this is the thing that comes out of it. Or if I go try this startup, even if it doesn’t work here, the things I’m going to learn, or in the case of the sales rep who goes out to that new job, it may not be an equity win. But you’re excited they offered you equity, but instead think about okay, what am I going to learn from this experience in a year? Right in the store, I didn’t tell you, which is what I usually tell about Jenny is that when I got to Admiral, Google just released remarketing. Probably two weeks after I got to Admiral and so I came home and said, hey, to this girl I just moved in with I can’t pay rent. And by the way, Google released the same product of this startup that I just joined. So I’m effed. Financially, I can’t do anything. Her answer was, if you’re going to learn something, you should stay there for at least six months, and I’ll pay rent. Because she knew the value of learning, we both had this experience as educators. And so she knew that that was valuable. She knew that was something that was valuable to me. And I was fired up about what I was learning about the ad tech ecosystems, right? So I was like, well, okay, that makes sense. And then, you know, of course, you know, I’m not gonna let her out of my life, or ever move out. So I stayed. You know, it’s been over 10 years now, but that experience was pretty amazing. But it also changed my calibration and my compass to be what am I gonna learn from this experience? I’m not looking at; am I going to make my number this year? And how much do I make? You know, a lot of junior salespeople they get their plan or their offer letter and that comes to the comp plan or they’ve talked to another rep there and they start trying to figure out the great sales reps do this all the time. But start to figure out, okay, here’s what if I do X, Y and Z, here’s what I’ll make. As a VP of Sales I evaluated an opportunity based on if I can show up in four x where the company is today, in the next 18 months, as a baseline worst case scenario, if I think I can get into four x in 18 months, that I know that I’m still on the trajectory. I’ve been there more than a year and a half, I’ve been able to ramp up by the first six months, I was able to actually do the job for a year, learn a lot from that, I’ll get a lot of experience, it won’t be a blemish on the resume even though a bunch of VPS of sales get fired every year for doing their jobs with companies that aren’t ready. Can I go out and do that and have you know, four x growth? More than that is great. That’s the cherry on top. Everybody thinks you’re the most amazing thing since sliced bread. But if I think I can, Okay, can I go and four x. If I can do that in a way where I know I’m going to learn the thing I wanted to learn, like how a company goes from series A to Series B, how the fundraising happens. If I can use this as an opportunity to get into rooms I wasn’t able to get into before, whether that board meetings, or whether that’s who you’re interviewing and who you’re hiring, who you’re managing, getting to a place where you’re at a team big enough you can actually hire people smarter than you, which is really hard to do if you’re a startup of two or four people but it gets a little easier once the company gets bigger people see that you’ve got some success. And the people who used to be your bosses are coming to you looking for jobs, that’s an amazing thing. There’s a lot to learn from that. And so I think that all of us are in an opportunity where that kind of learning is in reach. But we have to be open to seeking it out.
Walter: Amazing. Ryan, as always, it’s a great conversation. Thank you so much.
Ryan: Thanks for having me.