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Index/Sales/Built Not Born: The Startup Go-To-Market Podcast
Built Not Born: The Startup Go-To-Market Podcast artwork

How Founders Mistake Traction for Product-Market Fit and Scale Too Soon

Built Not Born: The Startup Go-To-Market Podcast · 2026-08-06 · 32 min

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Key moments - from our scoring

Substance score

48 / 100

Five dimensions, 20 points each

Insight Density9 / 20
Originality8 / 20
Guest Caliber14 / 20
Specificity & Evidence10 / 20
Conversational Craft7 / 20

Carter Kast draws on three decades of operating experience - from launching Blue Nile in 1999 through leading Walmart.com's transformation into a $200B+ e-commerce business - to articulate why most founders scale prematurely. The core insight is that growth is seductive and easily confused with product-market fit, but sustainable scaling requires five prerequisites: absolute clarity on mission and alignment with your board and co-founders; confirmed product-market fit evidenced by true customer need, differentiation, and market size; identification of your ideal customer profile and white-space opportunity; organic, repeating customer loyalty rather than purchased growth through marketing; and unit economics that justify reinvestment (LTV-to-CAC ratios). Kast also addresses the cultural and structural challenges of scaling - moving from generalists to specialists without demoralizing early employees, maintaining mission alignment as headcount grows from dozens to hundreds, and developing financial acumen around cash flow and burn rate. His Walmart experience illustrates how even market leaders can misread strategic shifts: the company's initial hesitation to invest in e-commerce stemmed from incentive structures favoring physical store growth, a lesson in how organizational alignment failures can compound strategic blindness. Founders and VCs operating at pre-Series B through Series C stages will find the most value here.

Key takeaways

  • →You cannot scale before establishing mission clarity and alignment with your board or co-founders - misalignment on strategic direction is a primary reason companies fail during growth.
  • →True product-market fit requires evidence of customer need, differentiation the customer cares about, and market size large enough to sustain a business, not just early traction or revenue.
  • →Growth purchased through marketing without organic customer loyalty and repeat purchases is a warning sign; you must understand whether your unit economics justify scaling and whether customers are truly loyal.
  • →As you move from generalists to specialists, you must deliberately preserve culture by making behavioral norms tangible and visible, rewarding cultural icons, and removing those who don't align - the Sundown Rule (responding to every inquiry by end of day) is an example.
  • →Most founders and early-stage VCs overlook cash flow management and burn rate until it's too late; hire a strong finance leader early and deeply understand your monthly cash position to avoid forced down rounds or negotiating from weakness.

Guests

Carter Kast

Topics in this episode

Organizational changeProduct-market fit validationAlignmentKellogg School of ManagementOrganic growthmetricsUnit economics and LTV-to-CAC ratiosOrganizational scaling (generalists to specialists)Internal alignment and mission clarityBehavioral culture norms (Sundown Rule)Cash flow management and burn rateOmnichannel retailing strategyWalmart.com transformationIncentive structure misalignmentMichael Porter value chain analysis

Questions this episode answers

What are the three pieces of product-market fit that founders should validate before scaling?

True customer need and commitment, differentiation in an area the customer cares about versus competitors, and a market space large enough to sustain the business with a white-space opportunity to exploit.

How can you tell if your growth is organic or if you're buying it through marketing spend?

Examine whether growth comes from satisfied, repeating customers who return without deals, or whether you're dependent on continuous marketing spend; if it's the latter, you likely don't have product-market fit and scaling will burn cash faster than revenue grows.

What is the Sundown Rule and why does it matter for culture at scale?

The Sundown Rule requires getting back to every inquiry by the end of the business day, even if only to say 'I don't know yet' - it's a behavioral norm that makes people feel acknowledged and scales communication discipline as the organization grows beyond casual all-hands.

Why do generalists at early-stage companies struggle when specialists are hired above them?

Early employees see new senior hires who haven't done the foundational work, creating tension; the solution is reframing career growth as skill acquisition from those specialists rather than immediate promotion, with patience and mentorship from incoming senior leaders.

What unit economics threshold should justify scaling?

You should achieve LTV-to-CAC ratios of at least 3-to-1, meaning you make enough profit per unit sold to reinvest it productively into repeatable acquisition - if you don't have positive unit economics, you're counting on cash runway which becomes precarious during growth phases.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

9 / 20

The episode contains a structured scaling checklist with a few genuinely useful ideas - particularly the distinction between organic flywheel growth vs. bought growth, and the framing of incentive misalignment at Walmart. However, much of the runtime is consumed by personal backstory (Indiana farming family, swimming coach, Greek etymology of 'meek'), standard VC platitudes, and a lengthy rapid-fire section that produces little actionable insight per minute.

growth is seductive and shame on us VCs. We're always asking grow, grow, grow, grow. Right? We always are. It's seductive. But how are you getting the growth? Is the growth coming from a, uh, satisfied repeating customer not on deal, or are you buying the growth?
do the unit economics justify scaling? Are you making enough penny profit per unit sold to be able to plow it back into demand generation activities?

Originality

8 / 20

The Walmart incentive-structure analysis - C-suite stock comp tied to supercenter growth actively blocking internet investment - is a genuinely interesting first-hand observation. But the rest of the episode recycles well-worn frameworks: Michael Porter value chain, Ben Horowitz name-drop, LTV:CAC 3:1 rule, McClellan motivation theory, and standard PMF definitions.

You have to look at what's incense people. If you look at the C Suite executives, what are they incented by? Stock price. All of their compensation packages driven by stock. What drives the stock? At that point, Super Centers were doing well.
we shouldn't chase down Amazon. We need to be the best of what Walmart's good at, not chase them down their path

Guest Caliber

14 / 20

Carter Kast has genuine heavyweight operational credentials - CEO of Walmart.com during a pivotal period, early executive at Blue Nile, and senior roles at eBay - making him a real practitioner rather than a thought-leader figurehead. The score is tempered because he is now primarily in educator and advisor mode, which shifts some answers toward abstraction.

I was at Blue Nile and this was a, uh, Internet jewelry startup in 1999 and we were trying to do a D2C business in a very, very hard category in jewelry where there's a highly considered purchase.
Jim recruited me to come over to Walmart where he sat on the board and help launch Walmart.com

Specificity & Evidence

10 / 20

There are pockets of solid specificity - Blue Nile's $50M run rate, the Nasdaq crash from 5,000 to 2,000, Jim Breyer named as the Walmart board connector, sister as the 25th Amazon hire in 1995 - but the majority of the scaling advice is delivered in abstract principles without named company examples, concrete timelines, or hard data from Carter's own track record.

we had over 50 million in run rate revenue and then 01 hits and everything dries up. Funding dries up. The Nasdaq goes from 5,000 to 2,000. We could not raise a Series B.
My sister was at Amazon. She joined. She was the 25th person in 95, and she left in 2020.

Conversational Craft

7 / 20

The host is warm and well-prepared but defaults to validation and agreement throughout, rarely pressing Carter on specifics or surfacing tension. Follow-ups frequently echo the guest's point back rather than probe it, and the 'rapid fire' format collapses into extended meandering without the host steering toward harder questions.

I gotta say, um, I'm impressed because I'm not sure many people would've said it that early that they could see where the world was going.
There's that humble confidence.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker A73%
  • Speaker B27%

Most-used words

walmart22customer13love13hard13scaling12internet12market11trying10board10carter10growth10back10understand10cash10scale9team9

Episode notes

What if the biggest bottleneck to scaling your startup isn't market demand; it's internal alignment? In this episode of Built Not Born , host Sage Nye sits down with Carter Cast, former CEO of Walmart.com and Professor of Entrepreneurship at Northwestern University, to unpack a hard truth: most startups don’t fail from lack of demand, they fail from lack of alignment. Carter explains why mission clarity must precede growth and how misalignment at the top quietly fractures teams as companies scale. He breaks down what real product-market fit looks like (hint: it’s not fueled by discounts), and why sustainable unit economics are the only green light to accelerate. The conversation also dives into leadership, what separates high-performing teams from dysfunctional ones, how to navigate the shift from generalists to specialists, and why motivation mismatch often masquerades as underperformance. Above all, Carter makes a compelling case that self-awareness isn’t a soft skill; it’s the ultimate competitive advantage that defines how far a founder can go.

Full transcript

32 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: You can't scale before you have clarity of what you're trying to accomplish. Number one, do you have a clear mission and clear direction? What hill are you trying to take and is your board in alignment with you? Assuming you have a board, if it's not the board, is your co founder in alignment with you? That's what I would say. First, second, along the same lines of clarity, are you confident that you have product market fit? Is there true need? Is the customer showing you true need and commitment? Are you differentiated in some place that the customer cares about versus the competition and is the space big enough that you're competing in and have you found a white space area to exploit? So I always think of those three pieces of product market fit.

Speaker B: Hello everyone and welcome to Built Not Born, the startup Go to Market podcast by Venture Guides. I'm Sage Nye and around here we believe that great companies are built not born, one smart decision at a time. Each week we take you through real conversations with founders, investors, and go to market experts on what it really takes to land customers and scale your startup. Now let's get to work. Hello and welcome to Built Not Born. I'm Sage Nye, partner at Venture Guides. Today's guest is Carter Kast, a seasoned operator, advisor and educator who has led organizations at scale and helped build businesses from the inside. Carter previously served as the CEO of Walmart.com, where he helped drive growth of one of the world's largest e commerce platforms during a pivotal moment in digital retail. Earlier in his career, he held senior leadership roles across consumer and technology companies, and today he's an active board member, advisor and author and m working closely with founders and executives. He's also a professor of entrepreneurship at Northwestern University's Kellogg School of Management, where he brings real world leadership experience straight into the classroom. Today we'll be talking about scaling businesses, leading through change, and the lessons that Carter's learned across every seat at the table. If you're thinking about how to build a strong growth organization, how to scale your go to market efforts, or whether you should take that entrepreneurship class at Kellogg, the answer is yes. This conversation is for you. So, Carter, welcome to the show.

Speaker A: Thank you, Sage. It's good to be with you.

Speaker B: Awesome. I'd love to start giving the audience a bit more background. Can you tell us more about yourself and your own story?

Speaker A: I'll give you a couple influencing events of my life as a way because you don't want to be droning on through my resume. I think the first one is I Grew up in the flatlands of Indiana and central Indiana. My family and my dad's side are farmers. I named my first sons after my great uncle Glenn, who was a corn farmer who just was resilient and worked hard and lived to be like a hundred years old. Ate fatty foods, roofed the house when he was 90. And I think that's actually quite influential in terms of my attitude is just sort of a, uh, hard work, grinding, try not to draw too much attention to myself and just do the job. And I think that's a lot of the sort of geocultural influence of growing up in Indiana. See, the second probably big influence is I was a swimmer through college, and I had a coach named Steven Hunyadfi, who was a Hungarian. He fled during the 56 uprising of communism in Hungary and landed in Fort Wayne, Indiana, where I grew up, because he had a cousin that lived there. He was an Olympic coach for Italy and Hungary, gold medalists. And through his tutelage from age 5 to 20, I progressed in my swimming career. And he was a absolute hardass. He was as tough corporal punishment back this is in the 70s. Uh, he took me to Europe three times to compete internationally. But he was an enormous influence because he required such excellence and such commitment that I think even though I had this very love hate relationship with him, he frightened me. And yet I sought his approval. When he was dying, I flew from Toronto, where I was living, back to where he was dying and, um, visited him one final time. And the last thing he said to me in broken English, he said, carter, you are good boy. And I started crying. So I think these influences, you know, on our formative years are so important. And I think I was blessed in hindsight to have a really rigorous coach who taught me not just about hard work and dedication, but when we went to Europe, uh, he went to art galleries and he showed me a lot about cultural differences between Europe and the United States. So I think those influences mattered so much. And two of mine are kind of growing up in Indiana and seeing the hard work that my farming family, uh, how they provided for one another. And then having a, uh, sport like swimming, which really defined me, I think, as a person, the way I go

Speaker B: about things, I gotta say. So I was talking to a CEO a couple episodes ago, and he talked about this idea. When you're looking for people, especially in the early days, you need someone who has the humble confidence and also will work their butt off.

Speaker A: Can I tell you a humble confidence thing? This is so interesting.

Speaker B: Absolutely.

Speaker A: Can't believe you brought up unbelievable serendipity. I was talking to my father about a verse from Matthew and I'm not making this a religious statement, but in Matthew 5:5 I think they say, and the meek shall inherit the earth. And that's sort of a curious statement, isn't it? The meek shall inherit the earth. Well, my dad said that the Greek word for meek is prous P R A U s and prows also means controlled humility and strength. So my dad's interpretation of that is that the meek shall inherit the earth. It's the people that have controlled strength. Kind of like Aristotle's virtuous mean those people inherit the earth, those that have the humility. You know, the origin of that word is hummus of the earth. You stay close to the earth and um, you have that sort of resilience and stick to itness. So when I hear the phrase meek shall inherit the earth, I no longer think about being meek. I think about that sort of controlled strength and humility that ends up in the long run making the difference.

Speaker B: And I've got to ask now, because we've talked about your mentors and all of this point about humble confidence, which I will say, having known a couple people who know you very well, everyone says you have that in spades.

Speaker A: Thank you.

Speaker B: How did you end up@walmart.com I was

Speaker A: at Blue Nile and this was a, uh, Internet jewelry startup in 1999 and we were trying to do a D2C business in a very, very hard category in jewelry where there's a highly considered purchase. And we had done a really good job establishing the brand and we had over 50 million in run rate revenue and then 01 hits and everything dries up. Funding dries up. The Nasdaq goes from 5,000 to 2,000. We could not raise a Series B. We're running out of money. And you know Jim Breyer of Excel Partners. So Jim is on the board of Walmart. He knew of me from somebody and Jim recruited me to come over to Walmart where he sat on the board and help launch Walmart.com and I left in a moment of just feeling like Blue Nile was about ready to go under because we tried nine months to get funding. We couldn't get it. So I went to Walmart through Jim Breyer and then I was on a roller coaster for seven years, which we can talk about if you want of uh, how challenging it was at Walmart to launch E Commerce and the Internet when they were so good at something that it was hard to Want to change.

Speaker B: I actually would love to talk about that because everyone thought Walmart would get crushed by Amazon.com or by all these other online retailers. And if you look at the brand now, I mean, it's, it's stronger than ever. So can we dive into a little bit about the challenges of that?

Speaker A: Ah, yeah, this is good. You're just tearing the scab off and you're just going to start scraping it down.

Speaker B: I've got some salt on the table over here.

Speaker A: Wonderful. Yeah, let's get some lemon while we're at it. Good God. So let me first start by saying that I loved Walmart. I love the culture of humility and dedication. I love the culture of serving the customer. Every single thing they do there is an effort to strip costs out, pass the saving on to the customer, save money, live better is a, not just a mantra, um, it is a mission. So I love the place. But in 2000, when I joined, 2001, when I joined, let me say it different way. You have to look at what's incense people. If you look at the C Suite executives, what are they incented by? Stock price. All of their compensation packages driven by stock. What drives the stock? At that point, Super Centers were doing well. Add more Super Centers, stock goes up, everybody's happy, everybody's incented. So along comes a small division who's saying, whoa, whoa, whoa, whoa. We have to take some of the money that goes into super center, build out, reallocate it to the Internet. Because this Internet thing's happening and the people that are incented by the stock price that's driven by stores, same store growth or new store growth are saying, whoa, whoa, whoa. I gave this presentation Sage called my Walmart my way. And I talked about in the executive forum that the future of Walmart. And I used an archetype named Peggy. And here's how Peggy shops today at Walmart. And then I said, here's Peggy's daughter in 10 years. Here's how she's going to shop Walmart. And I showed what omnichannel retailing. These things weren't out yet. These little guys weren't out yet, but they were being talked about already about 2002, 3. And so I said, peggy's daughter is going to require a true omnichannel, um, experience. She's going to want to see how much inventory is in a store. She's going to want to be able to click and pull order online, pick it up in store. She's going to want to know what's on rollback, she's going to want to be able to tell you the store shopping pattern. She goes the golden path and she's going to want to know where everything is and what the price is. So she's going to know in advance what how much a basket of goods cost. So I laid all this out and called up uh, my Walmart my way and I said we shouldn't chase down Amazon. We need to be the best of what Walmart's good at, not chase them down their path. And what is Walmart good at? We've got thousands and thousands of supercenters with inventory sitting inside them and the whole game is turning over that inventory productively. So let's use the Internet as a vehicle and weapon for the consumer to shop however they want to shop at Walmart. You would've think when I gave this presentation, I had three heads, I'm sure it was like people were like. And I got a pat on the head basically from the CEO at the time and he said, we love having you at our company Carter, because you think differently. And I knew the minute he said that that I was not successful. I wanted him to say, how much is this going to cost? What resources do you need? Let's go. So what happened was we ended up getting into the billions of dollars and we got third behind Amazon and ebay at the time. We did a good job the team that I worked with, but we could have done so much more. Now what ended up happening, Amazon got into commodities that spooked everybody. They were now selling our core stuff and they got, I don't know what the number was, but as they started crossing 50 billion, 30 billion in sales, people realized it was not a niche business. And then there was a leadership change and Doug McMillan got into the saddle. A younger, more sort of Internet savvy CEO. And they invested in the Internet and they did exactly what we had the team and I had proposed before, which is use the store as your basis for winning. Don't try to ship eaches to home. You want to make sure that people can shop the Walmart experience and use the Internet however they want to to find and buy.

Speaker B: And it's echoing actually another story. Another guest on the podcast was the founder of Ecobee, the Smart Thermostat. And he was talking about the uh, when Google Nest came out and how do you respond to that? And the similarities that I see in sort of what he described is you really need to stop and think about what is your brand best at and then how can you enable that as opposed to trying to compete with someone else in their own, uh, territory that they just know better than you.

Speaker A: It's kind of. Michael Porter. You've got to understand your value chain and you have to understand the places in the value chain where you are truly differentiated and you have to leverage those to create new value. The problem Walmart had at that time, and I love seeing the fact that they have moved well beyond it, the problem they had at the time is their vantage point was that they were a real estate based retailer and what it should have been was they provide goods and services to anybody however they

Speaker B: want because ultimately it's the customer before everything else.

Speaker A: Right, exactly. And it just wasn't intuitive at the time because the Internet was nascent. If you took the time to look around the corner, you could see where it was going by two, by 2004, you could see what was happening. If you really thought about it, I

Speaker B: gotta say, um, I'm impressed because I'm not sure many people would've said it that early that they could see where the world was going.

Speaker A: Well, I was with a smart group of people in Silicon Valley, super smart group of about 200 of us, and we thought and talked about this all the time. We lived and breathed it and we could see that the Internet was just a massive enabler, it wasn't just a channel of distribution. So anyway, all's well that ends well. They really rallied and became an Internet juggernaut. I heard through friends that the Internet portion of the business is upwards of 200 billion now.

Speaker B: That's very exciting.

Speaker A: Yeah. So it's a big business.

Speaker B: So let's zoom out for a minute because Walmart's a brand that everyone knows, but you've had a lot of experience working with many scaling startups. Uh, are there common themes or lessons that you see that come up as companies are trying to build and find their place in the market?

Speaker A: I think Ben Horowitz called it the dark art of scaling. It's so hard to pin down. How are you successful scaling? I find like certain principles that I think are important for an entrepreneur to consider as they decide if they want to step on the gas or not. The first one is you can't scale before you have clarity of what you're trying to accomplish. Number one, do you have a clear mission and clear direction? What hill are you trying to take? And is your board in alignment with you? Assuming you have a board, if it's not the board, is your co founder in alignment with you? That's what I would say first. Second, along the same lines of clarity. Are you confident that you have product market fit? Is there true need? Is the customer showing you true need and commitment? Are you differentiated in some place that the customer cares about versus the competition? And is the space big enough that you're competing in and have you found a white space area to exploit? So I always think of those three pieces of product market fit. Third, are you super clear on who you're trying to serve? Who is the tip of the spear? Customer? Who's your ideal customer profile? If you know who the customer is, if you're confident that there is a space in the market that you can take advantage of, and if you're aligned with your co founder and with your board, then you've reached the first condition of clarity. That's number one. Number two, I'd say growth is seductive and shame on us VCs. We're always asking grow, grow, grow, grow. Right? We always are. It's seductive. But how are you getting the growth? Is the growth coming from a, uh, satisfied repeating customer not on deal, or are you buying the growth? If you're buying the growth through marketing and you don't have that flywheel of loyalty and repetition, then I don't know if it's time to scale because you're probably buying your way to grow. So you got to figure out, is our customer loyal and how can we make them more loyal? So that's the second thing I'd say the third thing is do the unit economics justify scaling? Are you making enough penny profit per unit sold to be able to plow it back into demand generation activities? If you're not, you were counting on cash Runway. And that can quickly change depending on the different things you're pursuing to grow. So unit economics and you know, everyone says LTV 3 to 1 ratio of LTV over CAC. Just think about it as when I'm selling this item, whatever it is I'm selling, am I making enough penny profit on this thing to plow it back into a repeatable way to get acquisition growth? So do the unit economics justify scaling? Fourth, internally, are you structured to scale? There's this move that you know well of, uh, that you got to go from generalists to specialists to scale. Early on it's like 30 of us running around and doing everything right. And it's fun, it's intoxicating. But over time we've got to bring in specific people in specific areas who have specific skills and you've got to do that while not ruining the culture and not deflating all the early people that worked so hard. Where do you have those gaps?

Speaker B: Yeah, can we spend a second on that? Because I do think leadership in those moments is so hard. And I know you've thought and written a lot about this, but when you have a team that's been generalists, uh, and been sort of working the 24, 7, 37, if they can somehow find those extra hours, these. Right. But you have this team, and then as you grow, maybe some people are able to adopt and be. And sort of find their niche and become specialists. Some people aren't. So how do you handle that? And how do you. It's one of the hardest questions, I imagine.

Speaker A: You know, it's interesting. My sister was at Amazon. She joined. She was the 25th person in 95, and she left in 2020. So she was there 25 years. Off and on she went and had children, and Jeff kind of reserved a spot for her, and she came back. So I asked what the hardest thing about scaling at Amazon was, and she said exactly what you just said. She said, it's the fact that you have all these hardworking people that are generalists, and they start getting people moving above them that haven't done all the work that they've had to get it where it is yet. They come in above them. And I said to Jennifer, my sister's Jennifer said, what do you do? Well, she said, I was one of those cart. I was one of those. I was the 25th. They kept bringing people in, and eventually she became very senior, but for years and years, they're bringing people in above her. And I said, what do you do? And she said, you try to find counselors and mentors that will help you. You try to go to school on the skills that those people bring that come in above you so you can learn from them. Um, and you try to have a patient perspective on your career so that one day you'll become one of those senior people that are skilled. Because my sister joined as a smart Stanford mba, but she didn't have all these skills. She developed them by working under these specialists, and eventually she became a, uh. I think she was the most senior woman at Amazon when she left.

Speaker B: Wow, that's impressive.

Speaker A: But it took. It took a lot of effort. I think it took a lot of time. And I think you've just got to be patient about your career. You got to ask, instead of like, am I going to get promoted next year? You've got to ask, am I gaining skills that are Going to make me really sought after.

Speaker B: Well, and it sounds like, as opposed to just getting frustrated by all of the people that get hired around you, what they can't do or what they haven't done, looking for the silver lining, figuring out what skills you can actually learn from them and absorbing and learning as fast as you can.

Speaker A: That's it. And then I think the last thing I'd say about scaling is you've got to understand your cash. I mean, I'll ask you this rhetorically. How many entrepreneurs really understand cash flow?

Speaker B: Yeah. Especially in the early days.

Speaker A: In the early days, it's hard, isn't it? It's hard. You've got to understand what your cash position is, what your cash flow situation is, what's your burn rate, how many months do you have? Because I have seen situations where people have a good business, but because they don't have an, uh, intricate understanding of their cash flow, they haven't hired a good director of finance or VP of finance or cfo. They end up cash strapped. And then they have to like, raise a down round or go back to the well when they're needy. And as VCs smell that, I do

Speaker B: think that's one of the hardest things for the company is when everyone's been working so hard and trying to make progress and stuff, but then you get yourself in a tough position.

Speaker A: So those are some of the biggies on scaling, I think. Overall, I always say to people, understand, as you scale, what are the areas that can break and try to have a mitigation plan for the areas that might break.

Speaker B: I'd love to spend a second. Speaking of areas that can break, when you have a small team, this idea of having a mission and having everyone aligned with it and moving forward is much easier to make sure that it's sort of disseminated across the group and everyone's focused. When you grow, that feels like something that would be very easy to break where you have, as opposed to 20 people, a couple hundred people, and not everyone knows each other and the mission gets diluted. How do you manage that? Do you have any advice for the founders that we work, work with?

Speaker A: It's a wonderful question because I think the biggest problem in scaling is internal misalignment. I think that's what hurts companies the most. The founder is no longer able to do these sort of all hands, casually. Whenever is needed, they're off on the road raising money. There's layers and layers of new people. A couple things. One is the founder has to be relentless about communicating the behavioral values that drive the culture. What are the normative behaviors that are essential in the way we will treat each other? Like, here's one weird one. Walmart had the sundown rule. You had to get back to somebody by the end of the day, even if it was. The answer is, I don't know yet.

Speaker B: Okay, I like it.

Speaker A: What are your norms of behavior that are essential to the culture? And then you've got to put those everywhere so people realize these are the five things we will not trade off. And when you see cultural icons that live up to that, reward them and make them visible up and down the organization. And when you see someone that doesn't buy into them out.

Speaker B: I like the sundown rule. We might have to implement that here.

Speaker A: I love it. It's one of my favorites of Walmart is, you know, even if you don't know, just get back to them to know they're being acknowledged. I don't know yet, but I'll get you the answer by Monday. I need to think about this and that. You know, whatever.

Speaker B: It sounds so simple, but in the age of all of this virtual connection and not actually talking or seeing people face to face, it's how we treat people, like humans. I really like that.

Speaker A: There's some good ones. I mean, they had some really, really good normative behavioral values that you've got to make the values tangible. You can't say integrity above all else. What is integrity? Integrity might mean saying the hard thing in meetings. What does it mean behaviorally?

Speaker B: Yeah, Carter, I could keep you here all day. This has been really fun, but unfortunately, I actually can't keep you here all day. So as we move forward, next section that we have is we call it our rapid fire section. Basically, it's a bunch of questions that we frequently hear from founders and leaders that we'd love to get your perspective on. So the first one is, how can you help an employee that's struggling to feel inspired get back on track?

Speaker A: It's funny you asked that one, because I wrote a book. I don't know if you asked that, because I wrote this book, but I wrote this book called the Right and Wrong Stuff, How Brilliant Careers Are Made and Unmade. And I looked at these curious cases of people that were skilled, they had the right backgrounds, and yet they weren't gaining traction in the company and they weren't performing. And I tried to understand what's going on there. When you have somebody skilled who's not delivering, they're struggling. And gosh, nine times out of 10, it's a motivation issue. I think you really, uh, really need to understand what gives that person energy and put them in the positions that give them energy. So let's take classic motivation theory by a guy named David McClellan of Harvard. Study motivation for 40 years. Key motivators. Some people are motivated by achievement. Dan Pink calls it mastery in his books. Some people are motivated by affiliation, teamwork, team play, being part of a team. Some people are motivated by power. They want to have influence and power. It's great. It's a neutral term. Fourth, some people are motivated by autonomy. They want discretion over their own work, high degree of discretion. And some people are motivated by purpose. They want to work on something that they think is meaningful to themselves or to the world. Those are five primary motivators. Achievement, affiliation, power, autonomy, and purpose. If you get somebody in a job where they just don't seem to be performing well and you can't figure out why, maybe it's not appealing to one of their core motivators. For example, let's say I'm in a job like I'm an, uh, enterprise sales manager. You're out in the road a lot, you're traveling, but it's not scratching your itch for affiliative, uh, interaction. Maybe you need to be more in a different job, like more of a PM job, where you're in the center of things and you're talking to people more and you have more sort of budding friendships, et cetera. Maybe you're in a job where you can't see the results quickly of your work because you're so achievement driven. And then you need to be moved into a position where there's a tighter scorecard. So what I dig into a lot, Sage, is trying to understand what energizes a person and put them in, give them work that aligns to their natural sources of motivation.

Speaker B: And, you know, this kind of comes back, I wonder, to our conversation about generalists and specialists. And as people are specializing, you could have a risk where they go into, let's use the example of, like, marketing. Just because someone needs to do it and, you know, they're jumping into that. But actually their motivators are better suited for a sales role or something where they're much more face to face with the customer. And so as you're scaling and learning, they'd be thinking about that as well.

Speaker A: I went into a job one time, and this headhunter that knows me really well said, don't take it, don't take it. And it was to Be the chief marketing officer of ebay. And I took it. But this headhunter that knows me, Lauren, she said, cart, you are so action Jackson. You're so twitchy that this is a consensus culture and it's going to drive you batty because that activation gene of yours is going to be twitchy. She was right, 100%. It's a great company, but it didn't match the way I'm motivated, which is by retail was perfect for me because it's like quick.

Speaker B: Makes a lot of sense. Okay, this was supposed to be rapid fire. Um, I'm not doing a good job here.

Speaker A: All right, that's my fault.

Speaker B: The next one is, as you are a leader or a CEO, uh, and you're thinking about building out your executive team members. What are the character traits that you look for? And are there any major red flags that are non negotiable?

Speaker A: Intellectual honesty.

Speaker B: Huge. I find that's harder to come by than people expect.

Speaker A: Oh, my God. People that are willing to confront and face reality and admit to their own mistakes. Being intellectually honest. If you can reduce your ego, detach from your own identity and just try to look at things as they are and problem solve. So that's 1, 2 accountability. People that have a bias for taking responsibility for outcomes, even if it's not all in their control, they take responsibility. Third, low ego drive, high ambition. Fourth, resilience and steadiness. Because this is a long game, isn't it? It's not a short game. And then lastly, I think the killer when you said the red flags is the inability to work well with others. People that their ego want. They want to be number one. They want to be. Was it Teddy Roosevelt or one of the presidents said, it's amazing what you can do if you don't care who gets the accol. It's amazing how far you go if you don't care who gets the accolades. You want people like that.

Speaker B: And especially because one of the ways that organizations can break down is when you're not sharing information. So if you have someone, even if they don't have direct reports, they need to be able to work with their peers and share information so that these organic people aren't operating without the complete picture.

Speaker A: So true.

Speaker B: All right, last question is, what metrics do you look at to measure success

Speaker A: while a business is scaling revenue and revenue quality? Do they have an acquisition flywheel that's not based on discounting that their CAC isn't too high and they have a quality, they're generating quality revenue From a combination of acquisition and retention, loyalty, revenue. So one is quality of revenue, second one is unit economics are improving so that they have enough margin to be able to build the business infrastructure. Brand talent, all that and sales and marketing. So they got to have the margin profile has to be there. And then third, I think they've got to have the cash management skills to understand their cash position and cash Runway. And that, as you hear me say over and over, that's usually an area of opportunity. People don't bring in the finance person early enough that really understands this.

Speaker B: You took the words out of my mouth. I was about to say the exact same thing. On, um, the finance part we see a lot. Fantastic. Well, Carter, thank you so much. Before we wrap up, I have a couple reflective questions for you. And I will warn you, I think this next one's probably going to be the hardest question. What's your favorite part about being a teacher now?

Speaker A: Oh, that's easy. My favorite part of being a teacher is having the ability to influence young minds. That simple. I've got this lovely job where I get these fertile 27, 29 year old minds and. And you have the ability to influence them. And the ironic thing is I end up learning more than they do.

Speaker B: There's that humble confidence.

Speaker A: The teacher's the student. You get smart people and you get a room full of them. And the teacher learns more than any of the students a wonderful job and

Speaker B: to the point of learning. What's a leadership lesson that you've learned either through some of your work with students or in your own career that you wish more founders understood as they're growing their businesses?

Speaker A: You will go as far as your self awareness allows.

Speaker B: Oh, I love that. Wow. I feel like we need to just stop here.

Speaker A: That's it. I mean, that's it. Uh, it's in life, right?

Speaker B: Yeah. I don't want to ask the next question because I feel like we just need to leave it there. Well, the last one is where can people learn more about you and the work you're doing these days?

Speaker A: You're right. We should have stopped at the other one. I'm on LinkedIn, Cartercast, and if you go type in Carter Cast and Kellogg, I have a bio page at, uh, Northwestern.

Speaker B: Perfect.

Speaker A: But I'm a. I'm an old gut geezer who's. I'm not really building my network as much anymore.

Speaker B: This has been an amazing episode. I'm still thinking about that last second to last question. Uh, thank you so much, Carter. This has been fantastic. And we really appreciate your time.

Speaker A: It was my pleasure. It was great talking to you. Really good questions too.

Speaker B: Thank you. Well if you find yourself in Boston, we would love to host you and I know our listeners are going to appreciate being able to hear all of your insights and learnings from quite an incredible career that you've uh, had.

Speaker A: Well that's nice of you to say. Thank you.

Speaker B: Build Not Born the Startup Go to Market Podcast is brought to you by Venture Guides. To find out more about Venture Guides and how our venture capital plus guiding model helps early stage startups build scalable go to market strategies and grow faster, visit ventureguides.com and then make sure to search for Built Not Born in Apple Podcasts, Spotify, YouTube podcast, podcast or anywhere else that you listen hit subscribe so you don't miss any future episodes and we look forward to building with you on behalf of the team here at Venture Guides, thanks for listening. Until next time, keep building.

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