Leading Innovation at Microsoft as a Cross-Functional Team Leader

Taylor Black, a cross-functional team leader at Microsoft and a seasoned entrepreneur discusses his role as a principal program manager for Microsoft's incubation studio and how it operates as a center of excellence for incubation within the company. Taylor also covers the challenges and differences between being an entrepreneur inside and outside a large company like Microsoft, highlighting the importance of agency and stress levels in both roles.

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📌TALKING POINTS

03:01 Transition to Microsoft 

05:31 Balancing Scalability and Startup Mentality

13:40 Rewards and Recognition for Internal Innovators

23:41 Decentralized Decision-Making Model

32:12 Entrepreneurship Inside and Outside the Enterprise

37:00 Agency and Stress Levels

41:41 Finding Happiness and Passion in Work

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Tom Finn (00:01.166)

Welcome in my friends. Welcome to the podcast. Today we are sitting down with my man, Taylor Black. Taylor, welcome to the show.

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Taylor Black (00:08.264)

Thomas, great to be here, thank you for having me.

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Tom Finn (00:11.342)

Taylor, it is great to have you, and let me take a moment to introduce you to this fine gentleman. He is a cross-functional team leader at a little company called Microsoft, and he is a seasoned entrepreneur passionate about driving innovation and growth. With 17 years experience, he transforms technical startups into scalable successes, partnering with industry giants like T-Mobile and Disney. His expertise illuminates innovation's path in the modern business era, I cannot wait to sit down with you and have this chit chat. For those of you that don't know, Taylor is a principal program manager for Microsoft's incubation studio. So let's start there. What does that mean? And what do you do?

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Taylor Black (00:57.68)

Yeah, certainly. So Incubation Studio is kind of a center of excellence for everything incubation at Microsoft. We sit in the Chief Technology Officer's organization, Kevin Scott's org, and we incubate. Now, incubate inside the enterprise is similar to what a venture studio might do outside the enterprise. So we take ideas from all across Microsoft. We work with the people who came up with those ideas to validate them often coming to a prototype and bouncing it off some customers. If there's a there there, we'll take that prototype, wrap a little bit of a business plan or a pitch deck around it, pitch it to my teams, internal stakeholders, and they'll fund it in dollars and headcount. We'll run it like a startup inside the enterprise through a pipeline that I've helped build and craft, along with a number of my team members so that it can move fast, so that it can really take those customer signals and learn from them and build and iterate and make mistakes and often die, but sometimes be a really great business success for Microsoft as well.

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Tom Finn (02:08.75)

So you consider yourself an intrapreneur.

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Taylor Black (02:11.164)

I do, yeah, it's a kind of, it's doing that Venture Studio thing inside the enterprise. So as a result, it's not exactly like a Venture Studio because it's not outside of Microsoft, it's within the corporate ecosystem. But there's a lot of similarities and that tolerance level between something the startup and moving fast inside the enterprise versus the big scale motions that enterprises must have, that's kind of my sweet spot where I like operating so that so that the entrepreneurs and the entrepreneurs who want to move quickly can do so easily inside the pipeline that we've built.

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Tom Finn (02:45.886)

I don't think I've ever thought about being intrapreneurial at a big giant like Microsoft. So how did you fall into this or how did you position yourself? Like what's going on here that you were able to carve out this really unique role?

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Taylor Black (03:01.584)

Yeah, certainly. So I was, this is the first big company that I've been a part of. The only companies I've been at before Microsoft in a FTE role were up to about 800 people. So I've been primarily a startup founder myself, B2B SaaS, where my people at, and also at external venture studios like the Invention Science Fund and others within the Seattle Venture Studio ecosystem.

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What really intrigued me about this role, opening up at Microsoft, is that there's so much that the internal corporate world can learn from the venture world in terms of running experiments, in terms of failing fast, in terms of being open to things that don't work and learning from them quickly, that I was interested in supporting entrepreneurs inside the corporation in the same way that I've been supporting them outside of the corporation. I really think that founders and those who have a bold idea and have all of that blood, sweat, and tears and energy to see that idea come to fruition need all the support we can give them. And that's where I've found myself in my career is not only externally kind of providing that support and building ventures and helping them understand how, you know, taking the things that aren't unique to the thing that… individual is building, like corporate setup, finance, HR, all of those operational sides of things, and letting them focus on the customer problem and finding that product market fit just allows them to accelerate and thrive in the things that they are particularly good at. And I saw that same opportunity inside the corporation. And so when the office of the CTO here at Microsoft kind of reached out to me saying, hey, we're building this internal help us build it, help us shape what this looks like so that entrepreneurs inside our company can thrive in a similar way and bring their innovation ideas to fruition. Would you like to do that? Yes, you know, there's a lot of difference inside the company though, right? A lot of politics, a lot of trying to do things that won't scale inside a organization that is intended to do everything at scale. So there's been some really interesting and great tensions in building that out but ones that I found super interesting and fun to work in.

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Tom Finn (05:31.874)

Well, we're going to get into a couple of examples in just a second, but I want to talk about this word that you just said, which is scale. So one of the things about a startup is you typically do things that do not scale when you start because you can't build it to scale right out of the gate. And then you just said, Microsoft is built to scale. So that is a juxtaposition, a fork in the road, if you will, that is actually very difficult to manage. So help us understand how you walk around Microsoft saying, don't worry, this unscalable thing, I'll figure out how to scale it later.

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Taylor Black (06:04.7)

Yeah, yeah, no, it's my favorite conversation. And you have to have that conversation in a variety of different subject matter areas too. I have to tell my finance people one thing. I have to tell my HR people another thing. I have to tell my legal people another thing. I think the core concept really to understand here is that there's no point in scaling anything until you've reached product market fit. And the only way you reach product market fit is by running lots and lots of experiments.

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And so what I've worked with our internal stakeholders on is building out a safe space for all of those experiments to happen while also putting a layer of metric accountability or idea validation mechanisms in place that allow us to report out in an analogous way to our external stakeholders what's happening inside this safe space so that they can have a good sense of what success might look like a year or two down the road. So pre-product market fit, we're running a bunch of experiments in does this technology actually work in the way that we think it will work? So reducing all of the technical risks there. We're working with very early stage customers, generally one or two, since almost all of our ideas are B2B, we're inside of Microsoft after all. And three, is there a business model that kind of supports this technology and its application to our customer needs. All three of those don't have anything to say about revenue. But outside the bubble, everybody is concerned about revenue, because again, we scale. That's what the enterprise is fantastic at. That's what we should be taking advantage of as a innovation mechanism inside of Microsoft. But there's analogues to what revenue could be. We can show, hey, this product is working in this way to solve this customer problem, and the customers are happy about it and value the problem that this thing solves at roughly this range of pricing, or this range of value proposition, monetary value. That utilizing, surfacing some hypotheses about how big our target customer audience is what our cost of goods sold is, how we think about the value prop for the entire chain, and the way in which it can also potentially provide incremental value to other parts of Microsoft allows us to tell a story much like a startup would to a venture capitalist saying, hey, you know what, I only have 10,000 customers right now. They're only paying me this much. But here's how I think we can get to these growth trajectories that you're anticipating and how I'm going to make a return for your fund.

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It's a very similar sort of story that we tell inside of Microsoft, except pattern to all of the things that are unique about Microsoft, the way in which they think about revenue, the way in which they think about their partner and sales organizations and motions and how we would fit into those. And so yeah, it's, it's that, it's that keeping of two worlds in mind. One, knowing that our, our startup, our incubation is going to graduate into the ecosystem of scale. Once we have a pretty good sense of product market fit and two, being able to provide that bubble, that safe space, that where they can iterate and grow in, knowing at the same time that we're giving them the skills necessary to survive once they're outside of the bubble.

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Tom Finn (09:37.654)

What a wonderful model and a nice blend. Help us with a couple of examples. Maybe one that has come out of the incubation area and has blossomed into a beautiful butterfly, or second, maybe one that just got killed pretty quickly because there was no product market fit and wasn't going to scale. And we said, no, thank you. And we moved on.

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Taylor Black (09:52.232)

Yeah. Yeah, no, certainly. I can give good examples of both. And our incubator is only about three years old. And so in some ways, we're still seeing our successes blossom. Venture scale successes generally take five to seven years before you have it all the way proved out. But yeah, let me see. Which one should I use? I'll use one that we call AI for game testing.

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It's an incubation that we partnered with our gaming org on, unsurprisingly. And a major part of any game development is testing that game. What we've done for this incubation, and it was a very tiny team inside gaming that brought it to us and said, hey, we think we have something here. Gaming itself was concerned that there hadn't been de-risked enough. They didn't necessarily want it on their P&L, their profit and loss sheet, because it had that amount of risk on it. And so it was definitely the appropriate kind of thing for a CTO's office to take on, because it's kind of further out and strategic, which is where those kinds of projects often get landed inappropriately. So AI for game testing provides autonomous agents that test the game, the gameplay as a user in all the ways that a user would test out a game. Except they're able to do it, unsurprisingly, at massive scale and much faster iteration than sets of users would be able to do because they're all automated agents from an AI standpoint. Note too, though, that because they can be generative, they're able to come up with gameplays or come up with things that… a random user might be able to do in much the same sort of way by being probabilistic rather than deterministic in the vein of generative AI. This one has seen a lot of great success as we went through our motions starting very early on where it wasn't clear that the technology would be able to produce the kinds of results that the folks were hoping for in the gaming side of things.

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Definitely initially early on, we weren't hitting the metrics that would have been useful for gaming, you know, particularly in false positives. This particular incubation had a lot of false positives to begin with. And it's hard to defend, you know, pursuing an incubation path when you have those kinds of metrics. But again, we had it wrapped in this little safe space bubble. We hadn't shown that it wouldn't work yet. It's just that it needed more time, needed more iteration.

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And potentially it needed a couple of different customers so that we were able to test out different modalities and not just a single game and that particular way of gameplay. And so through that iteration and through, I mean, the massive efforts of the incubation team driving this innovation, they've been able to make a lot of great strides and are showing a lot of value to this particular or where they anticipate landing. And we also anticipate them graduating from our program by the end of this fiscal year with every indication that they'll be providing that you know billion dollars with the value that our program strives for internally As they go through their motions, so that's one great example there

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Tom Finn (13:40.258)

So before we move on, Taylor, let me ask you this question. So the people that brought that to you all internally, do they get anything? Do they get a bonus, a promotion, a hearty handshake, and a new coffee mug with Microsoft on it? Like, what do they get?

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Taylor Black (14:00.816)

Yeah, generally, so there's kind of three ways in which folks find value in bringing ideas here. One, the ideas that they bring are Microsoft unique, where should they take their idea anywhere else or attempt to do it on the outside, they wouldn't see what they hope to achieve out of the fruition of their idea. Two, because they're Microsoft FTEs, and our incubator only works with Microsoft FTEs, you're able to pursue a startup-like endeavor and see a lot of personal impact and agency in driving a particular idea forward, while also being able to have the comfort and safety of being a full-time Microsoft FTE. Three, primarily actually due to United States employment laws, it's very difficult to reward or compensate people working on innovation projects substantially differently from those working on non-innovation projects. 

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And so while it remains something I hope to figure out from an innovation structure standpoint, we don't pump them any differently than we would on just a regular Microsoft project because of the ways in which stock is already figured out and stock plans already determined across the company. It's kind of a harder nut to crack along those lines. That said, you know, the success of these innovation projects often even more than the intrinsic pieces that the people enjoy working on the idea and are able to kind of thrive in this particular environment. We do tend to see particularly successful incubation projects. Folks are able to show- showcase their own value quite a lot quite a bit more readily and easily which always trends towards kind of faster promotion times. Not something we can guarantee by any means but that tends to be the trend inside our innovation programs.

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Tom Finn (16:11.33)

So let me break out my corporate language decoder ring, Taylor, for those of you listening, what Taylor actually said was, there is no additional compensation for anybody that brings an idea within Microsoft, which is totally fine. Then what he said is, however, the person that brings the idea that actually gets scaled within Microsoft, clearly, has a path towards some level of promotion within the organization, because everybody knows that you brought the billion dollar idea. So that means you may, if you play your cards right, have some role in that new business unit as it gets rolled out across the organization, because let's be honest, you were the guy, gal, person who came up with it. That is what he said in a really nice way. Yeah, did I nail it?

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Taylor Black (17:03.656)

Well done, Tom. Well done. You nailed it. I mean, you're better than Chat GPT.

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Tom Finn (17:16.05)

Take Taylor's comments and boil them down into plain language that he's not allowed to say because he is still a Microsoft employee, but I certainly am. Well done. Okay, cool. So that's one, that AI gaming testing sounds really awesome, super unique. And yes, a wonderful way to use AI for good and scale. And that sounds awesome. Can't wait to hear about it when it gets pushed down to the marketplace. So that's maybe a future success story, but I'm sure you have killed a handful of these pretty quickly. What are some that just kind of pop up that went, yeah, it wasn't a great idea, we killed that.

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Taylor Black (17:50.546)

Yeah. Yeah, you know, so I find that the ratio of ideas to long from our top of our funnel ideas to prototypes to incubations to successful launches is about 2000 ideas turned into 100 prototypes turn into five incubations turn into one successful launch. There's a very high degree of attrition throughout this process and intentionally so because we're running massive parallel experiments. Uh, let me see, there's two. Two, actually, one's a failure, one that we killed intentionally because it wasn't a good, actually because the technology wasn't there. And another one is one we killed in a very interesting way because it wasn't a platform company. At Microsoft, we are a platform company, that's what we do. So the one we killed because the technology wasn't quite there is one we call Fashion for Creators.

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Fashion for Creators is a platform that allowed creators to come to design garments in a three-dimensional space and then have those garments produced by actual garment manufacturers. But not just any garment manufacturers. It was a consortium of micro manufacturers which produced pieces of these different garments that you could create and would stitch them all in the end, stitch them all together kind of utilizing a huge network of a lot of different micro creators that would come together in producing the finished garment. There's a variety of reasons why this would be a really good thing from reducing landfill waste, reducing overbuilding, overproducing a lot of garments for certain markets, and it also kind of pushed the creator tools all the way to the very, to folks almost like you and I who could put together our own garments and have it created in a professional way. What we discovered there is that the garment industry isn't sufficiently digital or sufficiently collaborative yet in that particular vein to make this business model feasible. It can definitely be done in kind of a startup smaller practice way, you know, maybe kind of a tops maybe 10 million, a RR sort of business, which by no means is anything to that's something to be proud of if you've built a business like that. But it didn't make sense for Microsoft to pursue, particularly since we'd only be having a slice of that particular value chain. So we killed that one. Maybe actually only a few months after it became an incubation because the learnings were very clear. The second one that we killed, we had an incubation that was focused in the synthetic data space. And the particular synthetic data that they were working with, synthetic data is utilized to train various kinds of models. So for example, if you had a company that was working in healthcare data.

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As all of us know, healthcare data is super sensitive, it's difficult to work with. But if you're able to invent or come up with all of the data yourself, where it doesn't represent actual people, but it represents statistically significant portions of actual people, then you can utilize that data in a variety of simple ways, easy ways, because there's no real people that data is actually attached to. Just one example of the importance of synthetic data. But what we discovered, at least in the trajectory of this particular incubation was going, is that there wasn't a platform play that Microsoft could get out of this synthetic data incubation. So what we did instead is one of our customers ended up being very interested in taking some of this technology forward. And so we more or less gave away or sold all of the incubation stuff that they had come up with and a couple of the team members opted to go with this project to one of our partners. And one of our partners is pursuing it in its own sort of vertical play. One that utilizes Microsoft's technology stack, but one that the partner will be able to see a lot of value out of and Microsoft sees some value out of any partner relationship, of course. But was better focused on the way in which this partners business model operated and they're able to take that forward very successfully, where it wouldn't have worked for ours really at all and we wouldn't have been able to see that sort of value. And I think those kinds of relationships are super important for innovation programs inside of corporates because in the end, like the corporation is very focused on something that they are very good at. And I mean, you could be a $3 trillion company like Microsoft and still that scopes you to a much more narrow set of things that Microsoft should be doing successfully than the rest of the world. And if you have those exit points for ideas that don't make sense inside the enterprise but there's still something there, it provides so much value for innovation pipelines knowing that the idea is still going to thrive in a place where it should thrive rather than it being kind of a… a dead end, even if that dead end is a platform play for Microsoft.

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Tom Finn (23:41.55)

It's a really nice off-ramp to take an idea that maybe won't scale in Microsoft and give it right to a partner that can take a look at it, maybe spend a little more time on it over a couple of years, invest a little bit of capital, but know that, oh, this might be a $50 million idea. That's never going to fly at Microsoft. That's a bug on a windshield in terms of overall revenue. So it's never going to produce any scale.

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Taylor Black (24:00.326)

Exactly.

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Tom Finn (24:08.494)

That's a wonderful, wonderful off-ramp. I'm really, really glad you guys are looking at it that way because it's nice to take those good ideas and hand them off to somebody else who can manage them.

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Taylor Black (24:15.472)

Yeah, yeah, certainly. And yeah, it really helps all in the ecosystem. So yeah, yeah.

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Tom Finn (24:23.33)

So when you think about the internal work that you're doing versus the companies that Microsoft purchases, do you have an idea of what percentage Microsoft purchases versus incubates? And I would imagine right now it's tilted towards purchase because you've only been doing this three years, but is there a current state and then kind of what we'd like to see over the next decade where we're building our own, I would imagine.

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Taylor Black (24:50.032)

Yeah, yeah, so Tom, this is a complicated question and I'm gonna break it out into a couple of different pieces. And actually I think Microsoft is really, really good at this in the concept of placing parallel bets. So when I bring an incubation to my team of internal stakeholders, being in the CTO's office, I have to explain to my internal stakeholders why they should be spending money on - on solving this particular kind of problem as an incubation inside of Microsoft, as opposed to an investment from our corporate venture capital arm, M12, into a startup that's doing something adjacent or similar outside of Microsoft, or to our business development group who would be in charge of analyzing any mergers and acquisitions that we should be making in order to fill the same space. To further complexify things, we are one of maybe 15 or 20 incubators and accelerators inside of Microsoft. While we definitely are the ones sitting in the executive suite, there's a bunch of other incubators and accelerators doing really rich and fascinating work all across the company. At varying levels, some of them are more product or future-focused. Some of them are even further moonshot out technology focuses. But the important thing to realize here is that from Kevin Scott's view where he's sitting, Microsoft has a bunch of problems it could be solving. What's the best way in which he can allocate capital in order to solve those particular problems? Is it this incubation? Is it startup XYZ that M12 should be on the cap table of? Is it startup ZYXW that we should acquire in order to gain that business capability?

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Should this be done by a different incubator inside of Microsoft, or is more aligned to what that incubator is good at, or perhaps the organ within which it sits? All of those are viable possibilities. And in some business cases, it makes a lot of sense for Kevin to say, all of the above, please. Where we'll invest in an outside company through M12 that's kind of similar to something we might be doing inside of Incubation Studio.

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It's kind of similar to an acquisition that another business unit is making. Because Microsoft is in the very great place of being able to light all those fuses, wait to see which one finds the best product market slash scale trajectory, and then choose that. Killing the other ones. Now that's, that's impossible for, you know, businesses that, you know, you and I may have started because we only only made it to $100 million in revenue or something like that. But at the Microsoft scale, that's actually a really valid and powerful way of running parallel bets in order to find things that work out really well. What's fascinating to me about that approach is that it takes that startup mentality and moves it into somewhere in the mid-range of your growth scale rather than the startup sort of mentality pre-product market fit.

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Once you get to a certain amount of scale that Microsoft has achieved, you're able to think about multiple bets even in the growth stage, taking that experimentation mentality, pre-product market fit that all of us are used to in the startup world, and applying it much later on, where it's much more capital intensive, because that's still the best way for you to determine whether you should be moving forward with it or not.

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Tom Finn (28:34.018)

So who takes the ideas and determines if the new idea, whether that's an investment, whether that's a purchase, or whether that's an incubation, fits with the existing product line and product suite across the brand? Is there a final source of truth?

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Taylor Black (28:55.02)

I would say no. There's a collaboration between business units that happens. So for example, M12 has their own book of business and they present that to our executives and we're not necessarily in that meeting. My incubator provides our incubations and why we think they should be invested in. And we except we do provide how this is going to land in another product group inside of Microsoft because the CTO's office doesn't build We don't build products in the end. We De-risk things for product groups in order to the product group to build it themselves And and we paint a story of how this does help Microsoft's overall, you know market share in a particular area or why this brand new business line that we're posing as an incubation is an important business line for Microsoft to have, either because it knits together some product groups or it fills a major missing spot in kind of our overall strategic offerings. But as far as like a complete coordination across all of those things so that, you know, Kevin can lean back and on his surface and use his finger to allocate dollars towards a cohesive view of everything, that doesn't exist. And I think there's important reasons for that. Because the rationale between each of them, between each of the different groups and kind of their strategic objective and strategic perspective, differs enough that it changes the kind of paradigm as you move things in between it. And so knowing that you have different sets of capital allocated in these different areas and that each of them is optimized towards a certain kind of innovation allows you to better pattern match where you should be taking the kinds of bets that you're anticipating taking, if that makes sense. It is.

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Tom Finn (31:02.902)

Yeah, it's a decentralized decision-making model, which allows business units to structure and innovate faster than if you had one source of truth saying no, because they don't fully understand the scope.

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Taylor Black (31:10.268)

Exactly, exactly, exactly. Yeah, it's like that old adage we've always heard, you know, you always try to hire people smarter than yourself. It's in a similar vein there. You know, it's not a Dray-Conian kind of tops down decision-making. I know I've allocated this money into certain kinds of buckets where this kind of strategic investing is going on.

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Tom Finn (31:42.062)

Yeah, beautifully said. So when you think about all of this and you think about being inside Microsoft versus the companies being maybe outside, the startups being outside, I'm one of them, right? I started a company seven years ago in the SaaS B2B space, which you're very familiar with. Which one is easier, harder, more challenging, less challenging? What are the differences between being this amazing entrepreneur in Microsoft the challenges you face versus the things you've seen outside?

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Taylor Black (32:16.516)

Yeah, this is a great question and one that I love because I'm always trying to get the best of both worlds. Being a so I was a startup founder to a number of years ago sold in 2014 In the BDB SAS space. I had another startup before that kind of in the prop property space, which is a lot of fun, too But that's it's being a founder outside of the enterprise is existential If you don't make it you don't know have food on your table ostensibly, you know, the stakes are a lot higher in that sense. Not always, but you know, generally, if you're pursuing the founding role, you know, there's people who aren't gonna get a paycheck if you don't figure it out from your startup's perspective. That's both exhilarating and terrifying, but what it really does showcase is that you have a massive amount of agency when you're outside of the corporation.

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It's you, my friend. You're the one who's making the sale or you're the one who hired the person to make the sale. It's your technological expertise that got the product to where it needs to be. It's you keeping tabs on your churn funnel and all of your funding is coming directly from your customers or directly from investors who you've told you can get customers in order to make their balance tables, sheets work out in the end. And it's awesome. And it's important. And in fact, that's one of the biggest generators of value for the entire ecosystem economy. If you put all of us founders together, we have a bigger market cap than the Microsoft does. So how does it differ inside the enterprise? Well, inside the enterprise, you get a paycheck and it's really not tied to your incubation success. In fact, if you try to tie it to your incubation success, HR has a lot of problems with you. And so there's that interesting paradigm shift there.

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It works more slowly because you're tied to enterprise motions, even if you've been able to carve out a little safe bubble like we have in the incubation studio, where you can move dramatically faster than the enterprise, it's still not as fast as you would be moving outside as a solo, as an entrepreneur. So it's safer. But also there's a whole lot more bureaucracy and red tape because you're going out and you're talking to people who… are all oriented towards those enterprise scale motions. And you're saying, hey, I have something that's really cool and really risky and I can't, I don't know if it's gonna have any revenue yet. And yes, I know all of your metrics and all of your compensation are based on hitting revenue targets or things that are very concrete. But here's why you should have this one that doesn't make sense in that paradigm. It's kind of an uphill battle. You have a lot to, your whole, your whole way of going about selling your incubation, your whole way of going about iterating your incubation, differs a lot. Now, you know, there's a lot of overlap, but that's kind of the truth of the both ecosystems. 

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As a founder who's been outside and had the blood, sweat, and tears there, and as somebody who's worked in venture studios, both inside small organizations and large organizations now, I myself personally very much see the entrepreneur as having a great time, spending time in both ecosystems. You know, my own personal reasons for being inside of Microsoft right now is like there's a bunch of fun problems to solve that are very entrepreneurially focused and politically focused too, which ends up being a piece of being an entrepreneur as well, because all politics is sales in the end. But it also kind of fits my lifestyle right now. I have three kids. I've been the startup entrepreneur working the 120 hours a week, and that's not what I wanted to do at this point in time. And so it's cyclical in some ways. I'm thoroughly enjoying working inside the enterprise now. In five years, when the kids are a little bit more settled, I fully intend to be on the outside again, doing the founder journey and pursuing that with more… autonomy at agency and less cushion than I am currently. So it's a back and forth sort of thing, I think.

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Tom Finn (36:55.906)

So let's talk about the stress levels in the two roles as we compare sort of the good and the bad and the gift and the curse of both sides of that equation. How do you feel the stress levels are? You're in a unique position, Taylor. You have, you've been the guy, you've been the entrepreneur, you've sold the company, now you're in the big company with W2 income. Is there a stress level difference for you that you've seen personally?

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Taylor Black (37:23.632)

Yeah, yeah there is and I would explain the stress level purely in terms of agency. And by agency I mean your ability to affect the situation. When you're outside the enterprise it's you, you have a whole lot of agency. If you fail it's you, if you don't fail it's you and if you feel like you're failing maybe you can do another 10 hours of sales calls and make it happen. Inside the enterprise you have a whole lot less agency and that but also you have a bigger safety net right or not even a safety net you have you have that cushion because of the W2 and so are you the type of person who really needs that agency in order to feel like in order to have a low-stress level because you have something that you're able to do about it or inside the enterprise where your agency's cut by maybe 50%. You have a lot you can do within your scope, within your role. But there are layers of management. There are inter-org politics. There are shifting ways in which the enterprise will want to allocate capital that you yourself don't have a lot of control over. Is that something you're comfortable with? Does that stress you out more than having agency on the outside?

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I know people who can answer both ways. I know people who have brought companies inside the, I have sold to Microsoft and I've worked with them closely and they can't wait to get out again. And because, and in many ways they're stressed, primarily because they're bored in a weird way. It's not because they don't have a calendar full of meetings and things to do inside the enterprise, but they're not working on the things that's like feel the agency that they want to be working on. So that brings them a lot of stress. And once they leave, they're much happier people. So it's a balance I think there. I think that you can be stressed about money on the outside or you can be stressed about not having a lot of control over your own situation on the inside.

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Tom Finn (39:41.87)

I think that's beautifully said. I've been in both roles in big corporate environments where I felt stress due to not being able to get anything done, not being able to make an impact, listening to customers and then not being able to fix it for them and feeling very caught in the middle, quite frankly, just caught in the middle and that created some anxiety and some stress and I felt out of control in certain ways that… Being in a big company did not fit me at that point in time in my life. Now, as you get older, like you said, Taylor, you have some kids, right? All of a sudden you're able to see things through a different lens versus taking the high agency, high-risk approach that an entrepreneur might take in their external, outside the big company environment.

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Taylor Black (40:34.8)

Yeah, I think part of the reason for that is that, you know, all of my high agency, high-risk endeavor right now is my kids. You know, those, I really want to make sure that these little startups make it all the way through to a product market fit and, you know, scale after that. Um, and I, and I want to spend, you know, my full tank of energy on that. Uh, uh, and it's not to say that I'm not.

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Tom Finn (40:58.867)

Imagine being Taylor's kids. Hey, I just want to make sure my little startups make it to product market fit. Oh my goodness. Yeah, yeah.

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Taylor Black (41:05.922)

One of them is pretty close, the other two, there's a lot of experimentation still going on. Some technical problems, yeah. Customers aren't happy, yeah.

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Tom Finn (41:16.502)

Parents aren't happy, schools aren't happy, friends aren't happy, we're trying to figure this thing out. Oh man, I love it. Well, I love the work that you're doing at Microsoft, Taylor. I'm super grateful to have a chat with a person that has been in both roles and seen both sides of this coin and can really articulate it in a really meaningful way, because there are those that feel stress.

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Inside a company there are those founders and early stage employees that feel overwhelming stress. The grass my friends is not always greener. You just have to find what fits for you. Y-O-U-U. Point the thumb not the finger. Hold yourself accountable to figure out what you love and what you want to do and then execute the plan. That's how we find our happiness and our love for life and our passion for work.

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Taylor Black (42:07.356)

100%.

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Tom Finn (42:09.226)

My man, thanks for being on the show. Where can people track you down and find you? I know you're coming to us from a cellar today.

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Taylor Black (42:10.836)

Of course. It's true. I'm hard to find here, but easy to find on LinkedIn.

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Tom Finn (42:21.642)

Easy to find, Taylor Black, Taylor like Taylor Swift, black like a color, easy to find on LinkedIn as well. Thank you my friends, we'll put all that in the show notes, Taylor, appreciate you being on the show and the great work you're doing with your cohort at Microsoft.

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Taylor Black (42:37.945)

Awesome. Thank you, Tom. Great to be here.

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Tom Finn (42:40.162)

Thanks bud.