For Starters

About For Starters

Let's get real. Most advice on AI, CX, and startups is just noise—hype, clichés, and fluff. For Starters cuts through it all with raw takes, real strategies, and contrarian insights you can actually use. Sometimes we’ll go deeper with guests who bring the heat. No hype, just where we're headed. chriscrosby.cx (https://chriscrosby.cx?utm_medium=podcast)

Publisher

Unfiltered Perspectives on AI, CX, and Startups

Category

business · technology

Language

en

Explicit

No

First episode

2 Jan 2025

Latest episode

1 Apr 2025

Latest episodes

16 episodes in the feed.

1. 

   1 Apr 2025

   Announcing, the Great Contact Center Rewrite

   Well, today's a big day. It's a big day for me personally. It's a big day for EndeavorCX, our company, and I believe for the contact center industry at large. I've been fortunate enough in my 30-ish year career now to have seen and played a part of multiple market transitions. Twenty years ago, we were moving from TDM to voice over IP. Ten years ago, that migration from on-premise to the cloud and CCaaS and SaaS taking over the world began. And it's no secret or surprise that the arrival of AI represents the largest opportunity for our industry to become what it can be. The problem is that the vendors that led the last market transition to the cloud are failing to lead this one. It's a different set of skills. It's a different competence. And instead, they've chosen hype over reality. They've chosen to issue press releases instead of release notes and ship product. They've chosen to change their messaging every quarter based on whatever the trend is for the day. This quarter, it’s agentic AI. They’ve chosen high per-agent-per-month pricing for bundles that are obtuse and don’t drive actual results. And they’ve also chosen to lock up your data in proprietary formats and models, making it impossible for you to stay in control of your own destiny. So today we change all that. Today I’m calling this the great contact center rewrite. It is unprecedented in the size, scope, scale, and depth of what we are doing. Today we’re not releasing a new product. We’re releasing a new architecture for the entire industry that puts you in control. It puts the data where it belongs: in the center. CCaaS is no longer the center of the universe. Your data is. Over the next 12 weeks, we’re releasing 12 products, not a singular product. We’re shipping 12 new solutions that will transform the way you think about AI, customer experience, agent performance, and operational excellence. We’ll be announcing some amazing things that you’ve never seen before—things I’ve never seen before. In my 25 years of building data teams and data products, we’re talking about knowledge bases that construct and write themselves, curate themselves, and deploy knowledge across the entire enterprise. We’re talking about the ability to have a data scientist equivalent running on open source language models that can pinpoint issues inside of healthcare plans, as an example. The constraint to realizing our potential in the industry is access to data—and two forms of data in particular. One is the contact call detail records. The other is the transcript. Whether vendors want to tell you this or not, 80% of all use cases in the contact center AI space start with a transcript. Call summary, sentiment analysis, identifying customer journeys, friction points, automating quality assurance—it all starts with the transcript. Today, those transcripts are locked up in proprietary systems. You have to pay a ton of money to get them out, or pay the hyperscalers a ton of money, or deploy a third-party solution, which also costs a lot and requires engineering effort to create an ecosystem to drive your downstream AI strategy. The first product we’re launching today is Prism. It is the first to market that is built on an open source model with a whole lot of pre-processing and post-processing know-how wrapped into it. It can connect to your contact center environment in as short as 15 minutes and start showing you insights. No code. No developing. No engineering. Nothing. It’s priced per minute, per talk hour. We’re at 90% cost reduction over most of the models and transcription engines in the market today. What that does is it sets the foundation. Now you own your transcripts. You own your call detail data. That serves as the library. It serves as your context. It serves as compliance. You now break free from having your data, your call recordings, your transcripts locked up in whatever proprietary system you’re paying a lot for every month. We’re making it cheap, fast, easy. This is the foundation. Over the next 12 weeks, as we release new functionalities and features, you’ll be set. If you already have transcripts today—awesome. Let’s bring them aboard. We can serve as your archival metadata layer now and forever. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriscrosby.cx (https://chriscrosby.cx?utm_medium=podcast&utm_campaign=CTA_1)

2. 

   7 Feb 2025

   Just Make It Easy (J-M-I-E)

   Today, my advice to startups is to tattoo the following acronym somewhere where you will see it every single day: J-M-I-E, which means Just Make It Easy. I came up with this several years ago when I was traveling relentlessly and found myself flying Southwest a lot—not because they were always the cheapest carrier, but because they Just Made It Easy. I could book last minute. I could cancel last minute. I could change a flight last minute without fees, without calling. And so I found myself a very loyal customer because of that. I started adopting that mindset into our companies—just make it easy for someone to do business with you. Just this last week, I've reached out to a number of startups that I thought could help us, particularly with emerging AI capabilities that are interesting. Only two of them actually made it easy to get on the phone, walk through a demo, walk through the product, and then actually made the buying process easy—very clear with their expectations and what they did and didn’t do. And, you know, they fumbled through the PowerPoints or whatever, which is fine. I still do that. The rest of them made it almost impossible to do business with. I had one dude from a pretty well-funded startup where the soonest appointment they had was five days out. Then he was five minutes late for the demo, so I had already bounced, and he emailed me wondering why. Just yesterday, I had a sales meeting booked, and it was declined by the founder because he made some assumptions about us as a portfolio instead of actually just taking a 15-minute call and realizing that I probably would have done two sales with him. And those are just very recent examples. The list is long with folks who, for whatever reasons, are just making it difficult and introduce unnecessary friction just to do business with them. The point here is to step back and look at all of your processes—whether it’s sales, onboarding, post-sales support—just make it easy to do business with, just make it easy to transact. And man, you're going to accelerate a lot faster than being a pain in people's ass. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriscrosby.cx (https://chriscrosby.cx?utm_medium=podcast&utm_campaign=CTA_1)

3. 

   6 Feb 2025

   The M&A Drought: Understanding the Current Market Shift

   Last week, I did a post about how I felt that AI in the contact center industry had plateaued rather than seen a bubble. We'd run out of innovation, effectively. And the result of that was a lot of companies that look alike. There was a comment made to that post, which was quite insightful—part of the reason we still see so many companies doing the same thing is because of a lack of M&A activity in the market. And I think that's quite astute because one of the most important pieces of advice I give a startup or a founder is to know the sea you're swimming in and to know it cold so that you can predict the currents before they change. Every startup at some point is going to have a liquidity event. You're either going to run out of cash and die, or you're going to go IPO—which very few companies actually achieve. Or you're going to exit through acquisition, which is the most common way to realize liquidity, aside from going defunct. But right now, very few companies are buying. Rewind five years, ten years, fifteen years, twenty years—the M&A activity, particularly in contact centers, has been quite rich. You've got NICE and Verint, both roll-ups built over two decades that started out as call recording and then diversified. Beyond that, back in the day, you had Cisco, Avaya, and Genesys, all of them quite acquisitive. At some level, Zoom was in the early days as well. Fast forward to today, and really, in this post-GPT moment, the only companies getting acquired right now are the ones adding material cash or cash flow to the acquirer. Take NICE—they’re only buying companies that will improve their quarterly earnings. Look back two years—prove me wrong. Five9 is interesting. I think they probably overpaid for Aceyus, but that was more of a tuck-in strategy that would have added some level of cash contribution to their earnings. Zoom hasn’t acquired anyone since Solvvy a few years ago, probably because their organic growth is at a level where they don’t have to make a lot of acquisitions. The FANGs—the Facebooks, Apples, Netflixes, and Googles—they’re also not buying right now. They’re either building this stuff in-house or waiting for the market to mature enough. The point of this is that no matter where you're at in the adoption or growth lifecycle, you need to be thinking about who the acquirers in your space are. How do you align with them? How do you understand what’s important to them? And then, at some level, how do you think of your company not as building products, but as the product—so that at some point, you’ll have that liquidity event or some type of acquisition. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriscrosby.cx (https://chriscrosby.cx?utm_medium=podcast&utm_campaign=CTA_1)

4. 

   31 Jan 2025

   Market Bubbles, Plateaus, and Gray Swans

   Today, let's talk about market bubbles, plateaus, and gray swans. For the last six months or so, I've been looking at AI in the context of the market, and it has felt pretty bubblicious—like we were hitting a bubble with a ton of companies jumping in. Some of them couldn’t even spell "contact center" a year ago. And some can’t spell "AI" most days. At this point, there are probably hundreds of companies doing pretty much the same thing. Most of them are either focused on voice automation and chatbots—much easier to build today than even a year ago—or they're working on some flavor of call summarization, quality assurance automation, sentiment analysis, or CSAT. They take a call transcript, evaluate it against criteria through a prompt, generate output data, and put a front end on it—suddenly, it's a product. We had already seen some of the air coming out of that, especially with the recent struggles of high-profile startups and the noise around deciphering real differentiation. Then last week, DeepSeek released its R1 model, catching the market by surprise. It wasn’t a black swan event like GPT’s original release, which was a true paradigm shift, but it reset the market in many ways by unlocking new capabilities that didn’t exist a week ago. Now, it's possible to run one of these high-performance models on commodity hardware, and cloud hosting providers are offering the full model at a fraction of previous costs. This shift opens up new possibilities for tackling complexity. I no longer think the market was in a bubble. Instead, it had plateaued—everyone reached the same level, running in circles trying to figure out the next differentiation. Some companies will recognize the opportunities that these new models and paradigms unlock, using them to create new products and categories. Others won’t, simply because these models introduce new capabilities that many don’t have the context to apply. If a model touts PhD-level benchmarks, but you don’t have the expertise or the right questions to ask, you won’t get significantly different results from R1 than you would from GPT-4 or any other model. But those who understand the potential of models that don’t just generate code but can tell you what code to generate—or that don’t just create data but bring in vertical context to analyze it and surface new trends—will create an entirely new category of solutions. We're going to see a divide: companies stuck at the plateau, having reached the limits of their competence and vision because they’ve only focused on automating what we already know how to do, and those who keep climbing, separating themselves by bringing entirely new capabilities to market. Some of this will be driven by open-source models, making it possible to buy a Mac Mini and generate high-quality data 24/7 while leveraging more powerful models for reasoning-intensive tasks. The accessibility of these capabilities is shifting rapidly, and I expect we’ll see a wave of innovation until we hit the next summit. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriscrosby.cx (https://chriscrosby.cx?utm_medium=podcast&utm_campaign=CTA_1)

5. 

   28 Jan 2025

   The Currency of Trust

   Few things can be more important to an early-stage company's success—or any company's success, really—than your ability to build trust with the market, with your customers, with your employees, the folks that you're recruiting, and partners in the industry. Exercising that leadership and integrity draws people to place their faith in you. That includes everything from: Will you be in business tomorrow? If I'm going to write you a check and build parts of my organization around you, how can I trust that you'll have the financial resources and ongoing ability to deliver? A recent example is this week when the whole DeepSeek controversy hit the internet. The open-source AI model came out from China, and there was a lot of fear and uncertainty in the market about what that meant for people. If it was deployed, would data be going overseas to China? Could it cause some type of security issue? Then there was the camp we’re in, which embraced this new technology pragmatically to ensure the success and integrity of our business and our customers. Through all of that, not a single customer reached out to us with concerns about what we might be doing with their data and this new DeepSeek model. I believe the reason for that is trust. One, contractually, we have a whole lot of safeguards in place to ensure data integrity—making sure data doesn’t leave the United States, strict access levels, HIPAA controls, and SOC 2 compliance. For us to start moving data around would be a breach of trust. It would be a breach of contract. But beyond that, our customers also know that we have the vision and pragmatism to be good stewards of their interests. That’s what building a reputation for integrity and trust in the industry comes down to—demonstrating that you are a good steward. I see us as stewards of our customers' data and their money. They invest with us every day, and we are responsible for delivering outcomes and results. As a startup, you have to demonstrate that level of maturity and leadership day in and day out—whether that’s through contractual agreements that create safeguards for clients if something goes wrong, or, more importantly, by proving every day that you’ve earned their respect. You need to show that you understand the market and these issues as well as anyone, and that you always have your customers' best interests in mind. While the world is melting down over what’s the right answer or the wrong answer, sometimes the best thing you can do is reach out to your trusted advisors, get educated, and then relay that back to your customers so you can lead them through the process. As you do that, you not only build trust and engagement, but you also build long-term relationships. That increases customer lifetime value because they know you're not going anywhere—and they know that you have their best interests in mind. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriscrosby.cx (https://chriscrosby.cx?utm_medium=podcast&utm_campaign=CTA_1)

6. 

   22 Jan 2025

   Knowledge-AI Readiness in Contact Centers

   Today, let's tackle AI readiness and “agentic” readiness, which I guess is the new buzzword in the contact center. There's a lot of, I think, misguided but well-intended advice that the very first thing you need to do is figure out knowledge management or a knowledge base. And while that is a critical component for a lot of reasons, it's not the very first thing you need to do. The first thing you need to do is ensure that the underlying technology you're acquiring—meaning your CCaaS, WFM, monolithic QA, or whatever applications or agent assistants you're implementing in your contact center—is open and extensible. I talk a lot about this: APIs and the ability to move data and knowledge back and forth between those applications. What will inevitably happen is that each of these use cases or applications in the contact center—whether it's an agent assistant, voice AI, or anything else—will have its own onboard knowledge management. Each one handles knowledge differently with memory and vector embeddings. So, you need the ability to move your knowledge in and out of these systems in an open and easily facilitated way. This means you don't need a knowledge base; you need knowledge orchestration between these applications. That starts with the ability to push out knowledge. As an example, we deployed Zoom's agent assistant. It has its own knowledge base, which is very utilitarian in nature. The only thing it does is power Agent Assist, but it has to work that way because of how it indexes all the knowledge. We have our own knowledge management platform that is open and extensible. You can create all your knowledge base articles in one place and, with just a few clicks, synchronize them directly into a Zoom knowledge base. If we didn't have this synchronization capability, you'd have to administer knowledge separately in Zoom, in your IVA, and elsewhere. By the way, we synchronize everything out and back in. The real point here is that if you're just going out to get a new knowledge management system, you're likely adding another tool in isolation. And if you're procuring and selecting your CCaaS, agent assistants, or any other system that doesn't have open APIs, you're just going to keep proliferating these applications without realizing their full value. So, coming back to how we've designed this and how we guide our clients: it's about thinking through knowledge orchestration with document management and knowledge articles. As we select partners to deploy voice AI, agent assistants, or even quality assurance, we can now perform deep quality assurance management. For example, we can embed a script directly inside a QA form or assess agent product knowledge right inside an evaluation using an LLM. The only way to achieve this is by ensuring those vendors have published API documentation and that you can access and use it. If you need help with that, let me know. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriscrosby.cx (https://chriscrosby.cx?utm_medium=podcast&utm_campaign=CTA_1)

7. 

   21 Jan 2025

   The Future of Conversational AI: Margins, Saturation, and Strategic Niches

   The following is an snippet from my conversation with John Walter (https://www.linkedin.com/in/jowalter/) on 1/15/2025 The current conversational AI vendors are doing quite well and are maintaining healthy profit margins. I've heard one mention an 80% profit margin number before. I'm just curious about your perspective on 10 to 15 years from now. When it comes to the ability of conversational AI vendors to maintain profit margins in that ballpark, I don’t think they will. I think 80% gross margins are achievable because the technology is becoming so cheap so fast. We were in conversational AI for a while, and back when we were doing it, it was much more expensive and complex. Now it's gotten to the point where there are so many open-source tools, and most of the intelligence is offloaded to the LLMs. You still have to deal with the plumbing, like voice connectivity, but even that is becoming super easy. What’s happening is a big proliferation of startups saying, “Hey, we’re another voice automation company, another conversational AI vendor, or another bot.” The market is saturated, which leads to compression of margins. In 18 to 24 months, you're going to see CCaaS vendors incorporating this technology into their platforms. I know for a fact that at least three of them are working on it. They haven’t released anything yet due to the risks of hallucinations and wanting to ensure they get it right. Pricing is also a factor since they’re used to charging per seat. Now they might need to adopt pricing models like per minute or per transaction. And, as always, price approaches marginal cost in the long run. Bezos’s famous saying, “Your margin is my opportunity,” applies here. Once something is no longer complex to do, it’s time to move on. Voice automation will likely remain big and noisy for another year, but the momentum is waning because it’s no longer difficult or complex. When I talk to contact center leaders, the gap between interest in voice AI and its adoption is striking. Everyone’s curious and eager to deploy something eventually, but they’re cautious because of hallucination risks. It’s interesting that CCaaS platforms are developing their own tools. This could align with a point where the technology advances enough to be confidently used with low hallucination risks, just as CCaaS vendors make it available natively. This ties into the earlier discussion about the delay between interest in a product and its adoption. We’re in the early stages of the technology diffusion curve, with larger brands waiting to see what happens. If you’re a startup in that waiting period, you’ll likely be cash-starved. Early wins might come from digitally native companies, but not from large banks or laggards, which take longer to adopt. There’s a market for niche, vertical applications, like a healthcare benefits bot connected to marketplace APIs with specialization that narrows hallucination risks. Good general startup advice: if you’re managing complexity on behalf of a customer, they’ll pay you. For example, integrating with systems like Epic in healthcare is a pain. Solving that is less about the voice AI and more about connecting into the infrastructure to facilitate transactions. That’s what you’re doing with ProxyLink—facilitating the transaction effectively. When I see generic voice bots, I’m not excited. It feels like a CCaaS play or a niche-focused play. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriscrosby.cx (https://chriscrosby.cx?utm_medium=podcast&utm_campaign=CTA_1)

8. 

   16 Jan 2025

   Lessons in Losing $$: Market Timing, Pivots, and Scaling GTM

   In this interview, John Walte (https://www.linkedin.com/in/jowalter/)r posed the question: “What if we make it an incentive so that if a company is willing to adopt this tool, they are also making these AI assistants more valuable? These AI assistants are becoming more useful to the consumer because they’re able to do more real-world tasks and not just write poetry.” My response dove into the complexities of market timing, lessons from past ventures, and how redefining our go-to-market strategy turned challenges into a scalable platform and successful exit. One of the hardest things—and probably not really talked about a whole lot around being a founder—is timing and gauging where the market is and where the appetite is. Then, tapping into that early traction while you build toward the bigger vision. What this sounds like to me—and I’ll tell you about Experian, which I think is super relevant here—is that the only two times I’ve really lost money in a venture were when I went direct to consumer. Your total acquisition cost or customer acquisition cost compared to customer lifetime value is typically inverted. It’s crazy expensive to acquire a customer because you’re competing for very limited wallet share. I mean, your $10 a month or $20 a month product is competing against everything else. So, the customer has to have a problem right then in order to pull out the credit card. And then you’ve got to keep them as a customer. If you look back 10 to 15 years at LifeLock, the identity monitoring company, they were pretending to be a tech company, but they were really a marketing company. They would spend $70 million a year—or per quarter—just on marketing to acquire customers. They also had a big retention problem. When we launched our second company, we went after social network monitoring for teenagers and kids—for cyberbullying, sexual predation, and reputation management. This was back in the early days of social media—around 2012, I think, when we launched. We realized that you’re asking your customers and prospects to adapt their value system in order to purchase your software. What happened was we were competing against a couple of other companies. One of them sold—I forget who they sold to—but their COO and I met one day. He said, “Man, you’ve just got to abandon this company. Walk away from it. There’s no business here.” But what we did—and I don’t call it a pivot as much as just redefining our go-to-market strategy—was I went to the identity monitoring companies and said, “Look, what we’re doing isn’t a standalone product, but it’s a great feature in your product, in your bundle.” So, what we ended up doing was becoming a platform—a back-end platform. We built out all the APIs so we had all the integrations into the social networks. We had all the algorithms to monitor for stuff. Then we went to these companies and said, “Just embed us. We’ll make it super cheap because our cost is so low.” And they all did—all of them except LifeLock, which is funny. We ended up selling that company to Experian because Experian has one of the largest consumer bases for identity theft monitoring. They’re a credit union, but they’ve got all these consumer products you’re talking about, right? So, they ended up rolling us into that. What that did was take our core product and our mission—which really stayed the same. We wanted to get kid protection, call it, at scale. DoNotPay, by the way, has raised $26 million, and I suspect a great chunk of that isn’t going into the tech—it’s going into what we’re talking about with acquisition costs. But we found that distribution, right? So, we focused on the infrastructure, the algorithms, and all of that because it is kind of a two-sided market in some aspects. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriscrosby.cx (https://chriscrosby.cx?utm_medium=podcast&utm_campaign=CTA_1)

9. 

   15 Jan 2025

   Stop Screwing-up Your Customer Onboarding

   Brex CEO and customer experience expert Chris Crosby shares the common pitfalls of botched onboarding and how to deliver a seamless customer experience that retains clients and drives business growth.

10. 

    14 Jan 2025

    Reimagining the Future of BPO: Scaling Excellence with AI and Innovation

    Chris Crosby, CX expert and BPO leader, shares how his company leverages AI and innovation to scale excellence, unlock new revenue streams, and deliver exceptional customer experiences at unparalleled price points.

11. 

    10 Jan 2025

    Evaluating the Channel: Rethinking Go-to-Market Strategy

    Good morning and welcome back to For Starters today. Let's talk about distribution, go-to-market, and the fabled channel, which, for channel, I'm defining as mostly sales agents, technology distributors—aka referral agents. First, as any company coming to market, one of the key things you absolutely have solved for is distribution—getting to market in a repeatable, scalable fashion. Whether that's knocking door to door, sending your cold emails, or finding partners that can accelerate your growth, some ways that happens is going into ISV marketplaces—pretty common with AWS or Google or the cloud providers. Also, CCaaS providers, specifically in our space, tend to have app exchanges. Some of those you can be resold on their paper, and you're going to give up, you know, 10 to 20% of a deal, or they're just simply kind of a pass, or they hand off a customer to you. Either of those is okay. Each of them requires a distinctive go-to-market investment, regardless of the partner. The other route to market, which is kind of in style these days, is going through distributors and sales agencies, where there's a bunch of these little referral companies out there that help companies select vendors—primarily in CCaaS these days. But now, with the proliferation of AI, there are some folks helping with that. The question, then, is: as a vendor, should you go to market that way? We chose to. We actually started that way, and in 2025 have ended all of our channel distribution partnerships and will no longer be working through sales agencies. And there are a lot of reasons for that. But primarily, you know, when you go to market through a sales agency—call it Avant, or AppDirect, or Intelisys—they're all great companies. They tend to work well when there are a bunch of companies that are substitutes for each other. So, CCaaS—there's a half a dozen CCaaS providers that if you're looking for that type of solution, you know, you're gonna look at NICE, or Zoom, or Talkdesk, or UJET, or whatever—Genesys. Those guys need to get the mind share, right? They're in competitive, pretty high-margins-still markets. And what happens is that sales agent, that expert advisor, whatever they want to go by, is gonna sit down, pull out a spreadsheet, ask discovery questions, and compare your solution to four or five others. Then they help that customer, you know, make a selection, and you're gonna pay 20% of your deal forever on that. Which means that every deal you're in, you're automatically going to have competitors, and your customer acquisition cost is going to be f*****g crazy because you're giving up 20% in perpetuity. So try to calculate a CAC on that and then sell that to an investor. The other thing that happens in that model is that your margins are going to be super compressed because they're not taking 20% of an EBITDA or even gross margins. They're taking 20% off the top, which means that's just 20%. As you walk down your P&L statement, that is just gone—20% commission forever. So imagine now trying to value your company on exit. My sense is that those are going to be discounted cash flows by whoever's buying you, because they're not going to want to take over and assume all of that liability—again, 20% on your book of business in perpetuity—unless they're an acquirer that's used to making those kinds of deals. You're going to be in pain, is my sense. I mean, there was one year that we wrote almost a half a million dollars in checks and commissions, and so those partners were making a heck of a lot more money than we were on the same revenue, and we were delivering it, right? The other side of that coin, too, or the thing to consider, is that every distribution channel you go through is going to require another level of investment for you. So do you want to invest in going to market where you know your competitors already are? Or do you want to invest in going to market in areas where there's still a lot of white space, where you can stand alone? Take that 20% that you would have spent handing off to some dude with a spreadsheet and invest that somewhere else. That's what we're doing. We're investing in more strategic levels of scale and different routes to market, so that we can break through that noise. Some of those will continue to be strategic app marketplaces where we have strategic alignment—places like Zoom, frankly, where you can get to scale with a “better together” narrative and attach to some velocity. Otherwise, you're just swimming in a contingency of noise, and that's not free revenue either. So it's easy to step back and say, “Well, if I do this, I don't have to hire a bunch of salespeople,” but you do, because you still have to hire people that can manage the channel for you. What you'll find—and I'm not dissing on the sales agents folks. There are some great ones out there, and I've got some friends that do this. And for clarity, we're a sales agency as well. We've got an advisory arm that helps customers, you know, select tech—primarily Zoom. You know, we're not shy to double down in the areas that we value and believe in. But we're creating mutual value in those cases, and we're very transparent with that. We're also adding additional differentiated services and applications around those services. So there's nothing against the model; it just tends to be value-extractive instead of value-creation, and it creates some lopsided revenue. You're going to end up with different folks that either are going to try to be a gatekeeper between you and your customer—which is a place I'm never a fan of—or they refer a deal in, they bounce to the next deal, and you never see them again, and you're writing a check every month. So it's a tough topic, and it's different for everyone. But I want you, before you get all excited about going to market through sales agents or different distribution channels, to really think about the opportunity cost of that. You know, what level of effort are you going to have to invest to do it right and to gain the mindshare that you need? And what's it going to cost you in the long run? And I think you'll probably come to a different set of conclusions—that maybe, if you do have something that stands out in the market, there's probably better ways for you to get your message out than to be in a competitive situation every single day. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriscrosby.cx (https://chriscrosby.cx?utm_medium=podcast&utm_campaign=CTA_1)

12. 

    9 Jan 2025

    Apprenticeship and Mentorship: Why Being in the Right Environment Matters

    Working closely with seasoned professionals has a way of sharpening our business instincts, teaching us how to handle finances, and ultimately boosting our confidence to start and lead companies. This post revisits the power of in-person mentorship, how it shaped my first venture, and why creating that sense of apprenticeship—even virtually—continues to be crucial. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriscrosby.cx (https://chriscrosby.cx?utm_medium=podcast&utm_campaign=CTA_1)

13. 

    7 Jan 2025

    Leadership in Startups: Level Setting the Myth of Founder Mode

    Leadership in startups is messy. Founders are expected to scale their vision, align teams, deliver value to customers, and pace industry transformation—all while navigating constant uncertainty. Yet leadership itself remains one of the least explored topics in startup culture. Last fall, Paul Graham’s essay on (https://paulgraham.com/foundermode.html)Founder Mode (https://paulgraham.com/foundermode.html) brought this conversation to the forefront. Inspired by Brian Chesky’s experience scaling Airbnb, it challenged the traditional wisdom of delegating to external managers as startups grow. Founders across the ecosystem latched onto it, many interpreting it as permission to centralize control and reinforce themselves as the keystone of their companies. This misinterpretation turned Founder Mode into an ego boost rather than the nuanced leadership tool it was meant to be. Founder Mode isn’t about being the hero or making yourself indispensable. It’s about identifying where your unique influence creates the most value and stepping in intentionally to reshape outcomes. Leadership is about diagnosing the system. It’s about recognizing when to activate different modalities based on the maturity of the organization and the type of challenges being faced. Founder Mode is one of those modalities—a powerful one—but only when used with precision and purpose. When Founder Mode Works Founder Mode is most effective in moments of adaptive challenge. These are the situations where no playbook exists, where the DNA of the company is at stake, and where only the founder’s perspective can realign the organization. At Airbnb, Chesky reasserted his influence to fight mediocrity and reorient the company around its long-term vision. This wasn’t about micromanagement; it was about re-establishing clarity and alignment. I’ve had my own experiences with this. Last year, when mediocrity and toxicity crept into one of my engineering teams, I fired the entire group in one day. That wasn’t about ego or control. It was about diagnosing a system that had gone off the rails, intervening decisively, and resetting the foundation for scale. Within hours, the organization was on a new trajectory, and today we’re in the strongest position we’ve ever been. Founder Mode isn’t about hovering over every decision or approving every feature. It’s about inserting yourself where your expertise and perspective are critical, driving alignment, and then stepping back. Misusing it to stay at the center of everything creates bottlenecks, undermines trust, and slows progress. The Danger of Overuse The wave of LinkedIn posts celebrating "Founder Mode" missed the point entirely. They turned it into a badge of honor, as if being the bottleneck for every decision were something to aspire to. This isn’t leadership. It’s creating dependency and feeding a hero complex. Bringing in outside managers can introduce mediocrity, but so can a founder who doesn’t know when to step back. Teams can’t operate effectively if they’re waiting for approval on every decision. Culture isn’t preserved through micromanagement; it’s built by embedding principles, aligning values, and empowering people to act within those guardrails. Leadership Through Modalities Founder Mode is just one modality of leadership. There are times when it’s essential to decentralize decision-making, allowing teams to execute without interference. There are other times when you need to observe from a distance, stepping back to identify systemic patterns and opportunities. Leadership isn’t static. It’s situational and requires constant adaptation. At InflectionCX (https://www.inflection.cx/), I’ve learned to toggle between modalities based on the needs of the business. Early on, I assumed that bringing in experienced operators would free me to focus on strategy. What I didn’t account for was how quickly drama and mediocrity would creep in when those operators didn’t align with our culture or vision. It wasn’t until I stepped back into the weeds—coaching supervisors, restructuring teams, and engaging directly with clients—that we regained momentum. Founder Mode worked because it was targeted. Once alignment was restored, I transitioned to a different modality, allowing the new team to execute while I focused on growth. Moving Beyond Founder Mode Leadership isn’t about staying in Founder Mode indefinitely. It’s about knowing when to activate it, using it to realign the organization, and then shifting focus. Effective founders don’t cling to control. They diagnose, intervene where their influence is most valuable, and build systems that scale without them. This requires humility. Leadership isn’t about flexing or making yourself the center of attention. It’s about creating conditions where your team and organization can thrive—whether you’re in the room or not. Conclusion Founder Mode is a tool, not an identity. Use it when the stakes demand your unique perspective. Step back when the system needs room to grow. And most importantly, lead with humility and adaptability. The strongest organizations aren’t built around a single person. They’re built around a culture of excellence, alignment, and trust. Founder Mode can help you get there, but only if you know when to put it down. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriscrosby.cx (https://chriscrosby.cx?utm_medium=podcast&utm_campaign=CTA_1)

14. 

    6 Jan 2025

    The Grind Isn’t Special, and Neither Are You

    Welcome back to For Starters (https://chriscrosby.cx/podcast). This week is all about tough love for my fellow entrepreneurs, and today we’re taking on hustle culture. Many of you post daily about grinding, sacrificing, and working 20-hour days to make the world a better place. Let’s be honest—that’s your ego talking. It’s really more about building your wealth and chasing status. Meanwhile, the real grind is happening elsewhere. It’s the single moms working two jobs to keep their families fed. It’s the dads working overtime after being laid off in corporate downsizing. Often, those are the same jobs your startup is trying to automate—or maybe improve—while you carry a martyr complex about your “sacrifices.” Let’s be clear: you’ve probably never held those jobs. You’re not an agent in a call center, and you’ve never driven an Uber. You went to college, came out in a position of privilege, and had the freedom to take risks. That’s not diminishing your hard work, but thousands of people who are just as capable will never have that opportunity because they’re too busy surviving. So here’s what founders need to do: strip away the ego. Stop pretending to be the chosen one. I’m not, and neither are you. Focus on creating real value by engaging with the people who live the realities you claim to care about. Talk to the single moms, the drivers, the agents—not the tech. Their challenges, insights, and realities should shape the solutions you build. That’s the work that matters. Skip the performative LinkedIn posts and show real progress. Insights, actions, and outcomes—not lattes skipped or hours worked—are what make a difference. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriscrosby.cx (https://chriscrosby.cx?utm_medium=podcast&utm_campaign=CTA_1)

15. 

    3 Jan 2025

    Unlocking Ecosystem Growth and Interconnected Systems

    Chris Crosby discusses the importance of ecosystem-wide growth and unlocking exponential potential. He highlights the limitations of traditional hub and spoke models in partnerships and ecosystems, where applications or products create new silos and require integration. Instead, he advocates for interconnected systems of complementary applications that create new value and systems. He uses the example of his company, endeavor Cx, which connects CX vendors and partners with other companies in the ecosystem to create a more integrated and valuable solution for customers. This approach, he believes, will lead to growth and success in the market. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriscrosby.cx (https://chriscrosby.cx?utm_medium=podcast&utm_campaign=CTA_1)

16. 

    2 Jan 2025

    Welcome to Day One

    Hi everyone, and welcome to Day One of For Starters: Unfiltered Perspectives on AI, CX, and Startups. This is a mostly daily podcast, starting today, where we’ll cut through the noise and jargon surrounding these topics and focus on what’s real. I’m Chris Crosby—entrepreneur, builder, and someone who’s been deep in startups and technology for over two decades. This podcast won’t be about clichés, AI apocalypses, or overhyped trends. Instead, it’s about real strategies—what works, what doesn’t, and why. For those who know me, you’ll know I don’t shy away from calling it like I see it. Whether I’m right or wrong, the goal is to bring fresh perspectives and challenge the status quo with a bit of a contrarian edge. Here’s what you can expect: * Daily takes: 3-5 minutes on tough topics. * Guest appearances: Occasionally, we’ll bring in guest hosts for deeper dives and more heat. * Portfolio highlights: I’ll introduce you to VenturesCX, the portfolio of companies I run. We’re tackling challenges at the intersection of AI, contact centers, and outsourcing, while pushing into new markets in 2025. This podcast is where we experiment, learn, and push boundaries. Bring your questions, your feedback, and your curiosity. Tomorrow, we dive in. Let’s get started. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit chriscrosby.cx (https://chriscrosby.cx?utm_medium=podcast&utm_campaign=CTA_1)

Reach and audience

Public platform figures. Ratings count people who left a rating, not total listeners.

Apple Podcasts (US)

5.0 / 5

1 ratings

Podcast Authority Score: 31 / 100

A composite of feed quality, social presence, YouTube performance and engagement. Read the methodology.

Quality

61

Social presence

0

YouTube

0

Engagement

0