Lessons from Corporate Innovators

Matt Fleckenstein Sr Director, Azure Innovation at Microsoft

Play episode

I’m excited to start another season of Agile Giants with my friend Matt Fleckenstein. Matt has been a VC, traditional entrepreneur and corporate entrepreneur inside Microsoft and Salesforce.

Matt & I talk about his observations generally across those experiences as well as his current role where he really leads innovation across an interesting portfolio of Microsoft Products including IoT, mixed reality and quantum computing.

(Full Disclosure: One of those traditional startups Matt & I co-founded together with two other founders.)

Show Links:


I also hope you’ll consider subscribing to Agile Giants if you haven’t already on:

  • iTunes (also if you feel like the podcast deserves 5-stars, would love a rating on iTunes)
  • Spotify
  • Google Play
  • Or use RSS in your favorite podcasting software

Full Transcript

Sean Ammirati (00:08): Welcome to Agile Giants, lessons from corporate innovators. I’m Sean Ammirati, your host, Co-Founder and Director of the Carnegie Mellon Corporate Startup Lab, and Partner at the early stage venture capital fund, Birchmere Ventures.

Sean Ammirati (00:22): Each week, I’m going to talk to guests who are experts at creating startups inside large corporations. I believe fundamentally a startup within a company is the same as one inside the proverbial garage, a group of entrepreneurs trying to make the world a better place using new ideas and inventions. However, I also believe some of the techniques and processes are just inherently different. This podcast is going to explore those similarities and differences.

Sean Ammirati (00:56): Welcome back to a second season of Agile Giants. We took a little break after the end of the first season, looked through the analytics, and really got a sense what was working, what wasn’t working. I’m incredibly excited about the guests we have lined up for the second season. That starts today with Matt Fleckenstein. Matt and I have known each other for a long time. For full disclosure, and I mentioned this in the episode, Matt and I actually cofounded a business together with two other individuals.

Sean Ammirati (01:24): Ultimately, we sold that business to LinkedIn, but over the years after that experience, Matt went on to do other traditional startups and actually three corporate startups, two inside Microsoft and one inside of Salesforce as well. You can see now Matt almost has a portfolio of corporate startups he’s running inside Microsoft, and is really taking a venture approach to running those.

Sean Ammirati (01:49): I think it’s interesting to hear him talk about how he approaches this and the lessons learned wearing both of those hats. So, you’re in for a treat today. I hope you enjoy this first episode. I’m looking forward to kicking off Season Two of Agile Giants with you all.

Sean Ammirati (02:09): All right. So Matt, thank you so much for joining me. Matt, start by talking a little bit about your background, because you’ve worn lots of hats, right? You were a venture capitalist, you were an entrepreneur in a traditional sense a couple of times over, and a corporate entrepreneur at least three times. Maybe just walk people through your career trajectory here.

Matt Fleckenstein (02:28): Yeah. The short story is I basically came out of undergraduate school with an English degree and had no idea what I was going to do with it. I stumbled into a technical writing position at a market research firm, and the very first product I got to work on was Purell Hand Sanitizer and launching their concept testing Purell Hand Sanitizer.

Matt Fleckenstein (02:48): It was a fascinating experience because I remember the target demographic was middle aged woman. I remember doing focus groups and every woman to a T who was the target audience said, “I would ever buy that stuff because all you do is smush to the germs,” and that was a good wake up call for me to realize, “Hey, truly innovative breakthrough products need to be looked at a little bit differently.”

Matt Fleckenstein (03:10): I was fortunate enough from there to get recruited to an early stage venture fund in Pittsburgh, and I got to work with a lot of startups coming out of universities, which just got me to kind of see that same movie over and over again. As you mentioned, I eventually went and did a couple of startups on my own, or not on my own, with a group of folks. One of which, of course, was with you.

Matt Fleckenstein (03:31): From there, stumbled into this entrepreneurial stuff within Microsoft back when Microsoft was trying to transition from Office as perpetual software into Office 365, and got kind of put into this incubation group that was designed to build productivity apps in the browser to compete with the Office group. Eventually, it spun into core Office and became what’s now Office 365. Then, went to Salesforce and did a couple of entrepreneurial ventures there.

Matt Fleckenstein (04:01): First, helping to create their marketing cloud and then their IoT Cloud. Then now, find myself back at Microsoft in the Azure Group managing a portfolio of entrepreneurial ventures, IoT, mixed reality, and quantum computing, for example, to name a few.

Sean Ammirati (04:18): Awesome. I want to get to that portfolio in a minute, but first, I mean going back to the Purell point all the way to today, you’ve been part of a lot of product launches, and recently you’ve launched a bunch of new products inside Microsoft. I want to get to how those launches are similar and different, but maybe first just for context, talk a little bit about the products you recently launched inside Microsoft.

Matt Fleckenstein (04:39): Yeah, probably the most notable is I mentioned that I am responsible for our mixed reality business, and the most notable is actually almost a year ago to the date, we announced HoloLens 2, mixed reality, head mounted display device that since we started in November, started shipping out to enterprises, and it’s had a pretty dramatic impact. We’re actually, quite frankly, struggling to keep up with demand at this point in time. We simply can’t manufacture the devices fast enough. So that’s an example, I think of a launch that goes kind of how you want it to go, right?

Sean Ammirati (05:13): Sure.

Matt Fleckenstein (05:13): Where you get it out there, and it’s wildly adopted. So, I think there’s a lot of interest and a lot of traction in that space, and that just happens to be one of those things where the product market fit and the timing is just really coming together nicely.

Sean Ammirati (05:29): Great. So if you were to contrast, I mean the startup that we did, we did a product launch together, you’ve been part of venture back startup launches, you’ve been part of corporate back startup launches, and product launches. How would you kind of compare and contrast launching in both those experiences?

Matt Fleckenstein (05:45): Yeah, I think they’re similar in terms of kind of the fundamentals are the same. Not surprisingly, the scale at which you kind of operate and launch is quite different. Right?

Sean Ammirati (05:57): Sure.

Matt Fleckenstein (05:57): I remember back doing a startup together, right, and kind of getting into one of those tech shows where you had 30 seconds or 60 seconds to get on the stage and make your pitch, and that was kind of your launch.

Sean Ammirati (06:10): Yep.

Matt Fleckenstein (06:11): Comparing and contrast that to last year in Barcelona at Mobile World Congress, launching HoloLens 2 where we personally sent invites out and flew a couple hundred press members from all over the world into Barcelona. Right? We kept them captive for an hour while we kind of had the stage and can kind of pontificate about whatever we wanted. Right?

Matt Fleckenstein (06:31): So, I think the scale and the level at which you operate is very different. But at the end of the day, the success or failure of them is actually fundamentally the same. Back even in the days of Purell and the whole way through my career, I didn’t realize it but it really, quite simply, it comes down to language now that we have in our vocabulary around product market fit, and it really seems to be that simple.

Sean Ammirati (06:55): I mean, so obviously as someone who’s has spent more time as a traditional entrepreneur and just kind of been studying corporate entrepreneurship, there’s a little bit of a jealousy of being able to fly 200 press to sit in a room, but do you worry about premature scaling, given the resources you can put against those kinds of launches?

Matt Fleckenstein (07:16): Elaborate on that a little bit more, Sean. When you say premature scaling, meaning?

Sean Ammirati (07:19): So to your point on product market fit, right? Typically, what I would say is if you scale before you have product market fit, you’ll often end up what the guys at Berkeley called premature scaling from the startup genome research.

Matt Fleckenstein (07:30): Yep.

Sean Ammirati (07:30): So I think of that as a risk in traditional startups, but it feels like even a bigger risk in a corporate environment when you can put that type of resource behind a product launch.

Matt Fleckenstein (07:41): I think it’s definitely the case, right? I think it’s, in fact actually a good example is, I’ll just come back to the product we were just talking about, right?

Sean Ammirati (07:48): Yeah.

Matt Fleckenstein (07:49): I think about last year or a year ago, launching HoloLens 2 and how it’s gotten great traction in the marketplace, but if you go back to the first version of HoloLens that launched in 2015 or ’16, that one, while reached some level of success, nowhere near the same level of success. I think that’s a pretty good example of kind of premature scaling.

Matt Fleckenstein (08:09): I think there are a couple of things. I think one of them was the target audience was probably not the right target audience. It was a fairly robust computer on your head, which also means it’s a fairly large device. I think the original target, although there’s predates when I came back to Microsoft, was really focused on consumers. I think since coming back, we’ve really pivoted and I focused us on more of the enterprise customers.

Matt Fleckenstein (08:33): But I also think in general, just the market for mixed reality has evolved, and I think it’s much more ready today than it was back in 2015. A good indication of that is something like Google Glass launching today, would be to great fanfare certainly when it launched when it did a little bit of a tougher road then. So, timing certainly matters a ton as well. So yeah, I think it is actually really easy because we do have resources that you can kind of pump into it to get that wrong and overlook some of those fundamentals.

Sean Ammirati (09:02): Yeah, I think that “why now” question is so essential. We created this tool at CMU called the Corporate Startup Canvas, and it’s one of the boxes on that canvas, and it’s interesting to watch corporate entrepreneurs sort of struggle with the why not a couple of years ago, why not a couple of years in the future, but it is essential. Your sort of Google Glass, HoloLens example I think is a great mixed reality example of that.

Sean Ammirati (09:25): Let’s step and talk about this portfolio, right? Because, you’re kind of an interesting person relative to people we’ve had on here, which is not only are you doing one product, you’re actually doing a portfolio of these projects for Microsoft. So, how do you kind of prioritize and split resources across those different projects?

Matt Fleckenstein (09:44): Yeah, it’s a great question. I think it’s actually one of the areas where I actually probably spend a lot of my time. I think it’s really all about trying to create a framework and trying to get everyone on board to understand how those decisions are made and how and when resources need and should be applied at the most basic level. I’m a big fan of Geoffrey Moore and I’m a big fan of kind of looking at the portfolio with his kind of Horizons, a lens on it.

Matt Fleckenstein (10:13): Now, that’s a little unfair because nothing that I’m touching or working on is Horizon 1 where it’s driving material revenue either today or in the next 12 months, but I do have a portfolio of things that are really spanned across kind of Horizon 2 and Horizon 3. Rather than just look at them as flat Horizons, I think we’ve had to come up with some sense of, “Look, where are we if it’s a Horizon 2 venture? Where are we on that kind of curve? Are we early Horizon 2 or kind of late Horizon 2, almost going to Horizon 1?”

Matt Fleckenstein (10:45): So, I look at something like IoT, for example, and still probably two to three years away from material revenue at Microsoft, not because it’s not generating a lot of revenue, but to be material 10% or so of your revenue in a place like Azure, it’s got to be fairly substantial and sizable.

Sean Ammirati (11:01): Sure.

Matt Fleckenstein (11:02): So, there’s one that’s, I would say, a little bit later stage and probably now, I don’t know, a year or so from kind of becoming material for us. I mean, something like mixed reality is a little bit further back. Last year, I would’ve said it was early Horizon 2, now it’s actually kind of jumped ahead and probably in that kind of mid Horizon 2 timeframe.

Matt Fleckenstein (11:24): So I think kind of coming up with that framework and getting everyone to understand where the different ventures are is really important. Then, I think it’s about kind of trying to understand, “Hey, when do you apply resources to start to scale these?” Right? This goes back to your premature scaling question. I think it’s really easy in early Horizon 2 or late Horizon 3 to come in and start applying a bunch of resources.

Sean Ammirati (11:46): Yes.

Matt Fleckenstein (11:48): Then, it doesn’t end well, right? It doesn’t work well. To me, the whole thing is all about just constant momentum and just keep moving forward and growth. If you scale too early, as you know, you just have major setbacks and then you have to go through a whole reset, and that just kind of stalls all that progress in momentum.

Matt Fleckenstein (12:04): So, the whole key to all of these things is just that constant kind of motion, that constant kind of moving forward, and that constant momentum that just picks up steam as you go through those Horizon curves.

Sean Ammirati (12:17): Yep. So, you’ve got the categorization of these using the Horizon 2, Horizon 3. I’m curious because you also were a venture capitalist, right? So, you have a background making traunched investments, if you will, right?

Matt Fleckenstein (12:33): Yep.

Sean Ammirati (12:33): Now in a VC context, that’s very easy. It’s like, “Well, this is a seed stage company. This is a series A, this is a whatever.” Do you think about trying to apply similar valuation and stage investments against the portfolio projects you’re doing?

Matt Fleckenstein (12:49): It’s not just think about it, I think I do it all the time. I haven’t necessarily used that as a public framework within Microsoft, right, in a way to kind of formally get us aligned.

Sean Ammirati (12:58): Sure.

Matt Fleckenstein (12:59): I think ultimately that’s, in some ways, the goal because I think ultimately, that’s a good taxonomy and a good way to think about it. I just don’t feel like I have enough data points yet to make sure that I’m mapping what happens in the private sector, right, to with what’s happening in the corporate sector, but that’s certainly something that I think I aspire to and certainly look at.

Matt Fleckenstein (13:19): All the time, I’m thinking about, “What, where is this company relative to these Horizons?” Mapping it back to, “This was a startup on its own, where would it be?” What resources would you be applying? Because, I just think there’s so many more data points out there in their private sector and in the venture capital world to kind of learn from and kind of model after, and many of those are much more public than things that are happening within corporations. So, I certainly tried to do that, and my goal is to ultimately get to that type of framework.

Sean Ammirati (13:47): Yeah, that’s awesome. I’ll send you something afterwards. We’ve been playing with some models inside CMU on this as well.

Matt Fleckenstein (13:53): Yeah, that’s something I’d love to kind of see it, right? I don’t have to feel like I have to invent stuff. I’d love to use stuff. So, that’s great.

Sean Ammirati (14:00): Yeah, yeah. I mean to me, the interesting thing is, and I think because most people don’t have your background that end up in these roles, they apply traditional kind of corporate finance metrics to these projects, and so they try to back into an IRR or an NPV or something like that.

Sean Ammirati (14:17): The problem is that, fundamentally, that has some first principle math assumptions that are just incorrect from a valuation perspective. I actually think cause many companies to systematically under invest in these projects, but I think you sort of backed into the venture economics, right, because you were a VC. That’s much more second nature to you than it would be many folks.

Matt Fleckenstein (14:40): I think it’s true. I think what ended up happening, actually, you hit an interesting point. I think they under-invest. I actually think what happens is they overinvest too early, and then that almost makes them shy and they back off when they under-invest when it’s time to start investing. Right?

Sean Ammirati (14:54): That’s right.

Matt Fleckenstein (14:55): They’re like, “We’ve done that once and the math didn’t work out then, the math certainly doesn’t work out now. Why would I do this again?” Right? It becomes a spreadsheet exercise versus a spreadsheet as an input into many different things that need to be looked at.

Sean Ammirati (15:08): That’s right. That’s right, because what you see the problem is the launching your next mixed reality product is nothing like making a decision on the next retail store that Microsoft may want to open up in some marquee location, right, plus or minus two standard deviations on a price per square foot adjusted thing.

Sean Ammirati (15:31): The retail store in Manhattan and the retail store in San Francisco, right, they have a pretty narrow band of outcomes relative to mixed reality. So, the math you used to explore one capital expenditure is just so different than the math you use to explore another. The problem is when you have unknown problem, unknown solution in these innovation things, you want to think about it more like buying learning options and valuing it more like a Black–Scholes option theory than cap backs of a large capital expenditure.

Matt Fleckenstein (16:04): I totally agree, right. Now, I will say it gets hard, right? When you find yourself and you’re in one of these things that’s kind of starting to take off and you aren’t pumping resources into it, right? You’re spending a billion dollars a year on some of these things and they’re not yet generating revenue, that takes a certain level of fortitude, right, to kind of continue to plow through that?

Matt Fleckenstein (16:24): So, I do think it’s really important that you change the way that internally you look at how you measure progress. Because if you simply measure it off of revenue in those early days, it’s going to be tough, right? You’re not going to see kind of the revenue return in the first couple of years relative to the investment.

Matt Fleckenstein (16:43): Again, I think that’s something the venture community knows very well and has gotten very comfortable with and kind of it’s why I think that a different venture capitalists and firms come in at different stages because they excel at and are covered with different levels of risk. In the corporate world, it tends to be like one level of risk and there’s no deviation, I think that’s sometimes the challenge, right?

Sean Ammirati (17:06): Yeah. I mean, we could talk about this for a long time, but I think there’s another element that you’re sort of touching on that’s right adjacent to this as well, which is one difference is when I think about, we just had a company go out and raise 40 million dollars, right? They talked to 30 firms about that raise.

Matt Fleckenstein (17:24): Yeah.

Sean Ammirati (17:24): Not all 30 said “yes”, I won’t go through the breakdown, but not all 30 said yes. If you want to raise a billion dollars to invest in one of your projects, right, you kind of have a one person that you’ve one pitch. Right.

Matt Fleckenstein (17:39): Yeah. Yes. There’s a woman named Amy Hood, our CFO, right?

Sean Ammirati (17:41): That’s right.

Matt Fleckenstein (17:41): Yeah. It’s going to come down to her.

Sean Ammirati (17:45): So, I think this is underappreciated. The weight of a “no” is very, very different, right? Think about that CEO out raising, right? If someone says, “Hey Keith, this is just a crazy idea.” He’s like, “Thanks very much. I’m going to go next door and talk to the next firm,” right? You can’t tell your CFO like, “Hey, appreciate your feedback. I’m going to go talk to the next Microsoft CFO and see what he or she says about this.”

Sean Ammirati (18:08): It’s very, very different, which actually leads to a question I’m curious about. So you talked about the fortitude, but any other things you’ve learned around getting funding within your roles at Salesforce or Microsoft?

Matt Fleckenstein (18:21): Yeah, I mean, this goes back to the kind of frameworks as well, right? I happen to be a fairly big fan of a gentleman from Wildcat Ventures, right, who I think you know who those guys are, right?

Sean Ammirati (18:35): Yeah, I do.

Matt Fleckenstein (18:35): Named Mark. I use that a fair amount just because I think it’s a very tangible thing that’s translated fairly well to product development and market development stuff, regardless of whether you’re in an early stage company or a corporate venture. It’s just a framework, but I think the key is to show the discipline to not go ask for the money before you’re really ready for it and before the market is ready for it.

Matt Fleckenstein (18:58): It’s fascinating. We were talking about kind of diversity of portfolio, and I’ve got mixed reality, and then I’ve got quantum computing, right? I’ll tell you about mixed realities now, and I’m looking at quantum computing and saying, “Man, I’ll be thrilled if that thing hits in the next five to 10 years,” right?

Sean Ammirati (19:14): Sure.

Matt Fleckenstein (19:14): Yet, the people who are involved in the quantum computing venture, super smart people, great people, they’re really passionate obviously about what they do. So, they don’t understand why, “Hey, why are you pumping so many resources into mixed reality, and why aren’t we getting kind of our equal share of that?” Right?

Sean Ammirati (19:33): Yep.

Matt Fleckenstein (19:34): So, the ability to kind of discipline yourself and not push for an ask earlier than you’re ready for it is essential. To me, it all comes down to setting out objective criteria and getting aligned on them to say, “Hey, what milestones do we have to reach before we go make that ask?”

Matt Fleckenstein (19:52): Even in the mixed reality business, I’m facing it right now. We’ve got such demand, we’re considering kind of bringing up additional manufacturing lines. Well, there’s big capital investments associated with that.

Sean Ammirati (20:01): Yep.

Matt Fleckenstein (20:02): We’ve been working with Amy and the CFO and kind of a number of folks to get aligned on, “Look, these are the criteria that we need to see before we come and officially make that ask, but know that if we actually meet those criteria, we’re going to come knocking on the door.”

Sean Ammirati (20:17): Yep, 100%. So, let’s come back though to step up a level and let’s talk a little bit about the differences from your perspective, having worn both hats, kind of corporate entrepreneur in a couple of different settings in a traditional entrepreneur in a couple of different settings. What do you think are the biggest differences between those two different types of entrepreneurship?

Matt Fleckenstein (20:39): I think one of the biggest differences is it’s almost the antithesis at some level of what you were talking about in terms of kind of, “Hey, if you’re in a corporate venture, you’re really pitching to one firm,” right?

Sean Ammirati (20:52): Right.

Matt Fleckenstein (20:52): Or, one interval in the firm, right? That makes it tough, right, if that person’s not on board. The upside of being in a corporate venture though is if you’re smart, there’s less time pressure, right? It’s not so much living day-to-day kind of hand to mouth and kind of making sure that, hey, you’re always kind of in that mode of raising that next round of investment and not sure where it’s going to come from.

Matt Fleckenstein (21:18): I just think that there’s a little bit more patience, and I don’t know that it’s intentional, I think it’s just you’re in this situation where once the company decides to invest in something, you’re in this situation where everyone is primarily focused on their day job, which is to focus on optimizing the revenue that’s hitting and we’re driving today.

Sean Ammirati (21:38): Yep.

Matt Fleckenstein (21:39): So, I think that fact that you don’t have those same people necessarily spending that much time looking at how your internal startup ventures going, give you some freedom and some patients to say, “Hey, we don’t have to rush this thing. Let’s play this for the long game.”

Sean Ammirati (21:55): Right.

Matt Fleckenstein (21:56): I think that playing it for the long game is something that’s really hard to do if you’re an entrepreneur. If you’re a venture capitalists, right, in a big firm, you can do that, but you as the entrepreneur can’t. In this particular case, I feel like you’ve got much more an ability to play it for the long haul, and I think some of the things you do if you know that are just different. I think that’s one of the biggest aspects.

Matt Fleckenstein (22:16): One of the things I like a lot about being in the corporate venture side of it, or the corporate entrepreneurial side of it is that you can basically go after big ideas, because you’ve got a long time to let them bake and kind of bring them to market.

Sean Ammirati (22:30): Right. So, I think something that you’ve done well there that not everybody that I talk to has done is you have these sort of big, in a venture capacity we would call them investment theses, but like you have these sort of big vision that you’re putting these projects under. So, you almost end up with your own portfolio theory of the projects you’re working against. Right?

Sean Ammirati (22:55): But to this time thing, what’s the cadence of checking in with the different senior managers stakeholders on these projects?

Matt Fleckenstein (23:06): Yeah. So for example, my manager is the person who basically runs the business and the marketing side of Azure, right? That’s who I report into, CVP named Julia White. Then, her manager basically runs kind of the business and kind of the marketing side of Azure Dynamics 365, and kind of Microsoft 365, which includes O 365. So really, basically all of our kind of cloud investments.

Matt Fleckenstein (23:33): I would say that I checked in with, I’ve got two formal reviews a year with my manager. I mean, obviously I meet with her all the time, right, on day-to-day business, but in terms of kind of formal, “Hey, go look at the state of the business and how things are going,” twice a year.

Matt Fleckenstein (23:49): Not surprisingly, because I think Sean, you know Microsoft at its heart is a very engineering driven company. They do their kind of product planning cycles on that twice a year cycle as well. Right?

Sean Ammirati (24:02): Sure.

Matt Fleckenstein (24:02): So, you kind of tend to take a look at the business and use that as kind of fodder into kind of an input into the product planning for kind of the next six months cycle or something like.

Sean Ammirati (24:16): So, this may be a bad analogy, but because you’ve worn best both hats, I’ll test this with you. So, is it right to think about this whereas like maybe, and going back to your startup days, traditional startup days, you might’ve done monthly or quarterly board meetings. You’re almost on a twice a year board meeting. Is that the right analogy, would you say?

Matt Fleckenstein (24:36): Yeah, I would say I’m on a twice a year board meeting in that regard. With that said, myself, for example the head of engineering who runs mixed reality or the head of engineering who runs quantum computing, we do do monthly business reviews.

Sean Ammirati (24:50): Yes.

Matt Fleckenstein (24:50): So, we treat them as if they’re a board meeting, right? Just with a smaller set of stakeholders.

Sean Ammirati (24:54): Sure.

Matt Fleckenstein (24:54): So, it’s interesting, right? It’s almost as if it’s you within the company and it doesn’t include the investors, right?

Sean Ammirati (25:00): Yeah, yeah. The management team meetings, if you will.

Matt Fleckenstein (25:03): So, that way…

Sean Ammirati (25:04): Like, monthly management team, off-sites or whatever. Yeah.

Matt Fleckenstein (25:06): Correct. We try to kind of be every bit as objective and disciplined as you would be if you were in a board meeting, right?

Sean Ammirati (25:11): Yeah.

Matt Fleckenstein (25:12): But again, it’s just a different audience. So as a result, sometimes, in good ways and bad ways, a different level of conversation as well, right?

Sean Ammirati (25:20): Yeah, 100%. Well, I could do this for hours, but you do have large projects you’re running. So, let’s just end with one more question here. So, go back and think about the student coming out of school with an English degree, I think it’s a pretty remarkable career that you’ve had, what advice would you have for students coming out of school today?

Matt Fleckenstein (25:44): Yeah, I think it speaks to, it doesn’t really matter, I think as much kind of what you studied, right? I think actually that in today’s world, having kind of diversity of kind of educational backgrounds is helpful. I will say, I have struggled my whole life with, “Am I kind of more of a right brained or left brained person?” I think I’ve got equal parts of both.

Sean Ammirati (26:05): Yep.

Matt Fleckenstein (26:05): As a result of that, coupled with the fact that I’ve just always had this learning mindset, right? I just love to learn, and it doesn’t matter what the subject is. It’s one of the things I loved about early stage venture firms was you had to learn new spaces and new technology all the time.

Matt Fleckenstein (26:22): I’m doing it now. Quantum computing, right? It’s not like I’ve got a background in quantum physics or anything, right, but learning kind of that space in that technology. So to me, it’s all about if you’ve got the mindset, that kind of growth mindset where you always want to be learning and always want to be kind of pushing and you’ve got a willingness to develop both your right and left side of your brain, then the only other thing you really need is just some grit and hard work ethic. It seems like those opportunities kind of tend to find you. Right?

Sean Ammirati (26:53): I think that’s true. I mean as someone who’s watched your career, because I mean cause we did start a company together and I’ve sort of watched what you’ve done, I also think you’re pretty fearless on taking big swings, which is helpful, mixed with that grit.

Matt Fleckenstein (27:07): Yeah, I think it is. I kind of view that as an element of grit, right? Which means great. It’s basically if you take a big swing, you swing for the fences, you’re going to miss most of the time. Right? So to me, the grit and the perseverance is getting back up and taking that same swing all over again, right, keep swinging until you’re hitting, right?

Matt Fleckenstein (27:26): So, I think you’re right. I think it’s one of those things where, and I learned this even way back when we did a startup together and I’ve learned it the whole way through, which is doing a smart startup, right, or doing something entrepreneurial and focusing it on, “Hey, it doesn’t have to be huge. I just want to get a nice win out of it.” The reality is, it’s just as hard as kind of swings through the fences.

Sean Ammirati (27:50): 100%.

Matt Fleckenstein (27:51): It’s the same amount of effort. You’ve got to do the same things. Right? So if you’re going to put all of that into it, why not swing for the fences? It’s me, I’ve just learned over time. At least personally, it’s not worth putting in all of that energy and all of that effort and everything it takes to swing to try to hit a single or a double.

Sean Ammirati (28:08): Yeah, there’s a great Reid Hoffman quote that I can’t quite put my finger on, but it’s something to that exact effect. It’s just as hard to hit a double as it is to a home run, so you might as well swing hard, and I think that’s exactly right.

Matt Fleckenstein (28:22): Yeah.

Sean Ammirati (28:22): I think that’s exactly right. Hey Matt, I really appreciate you doing this. It’s fun to catch up. It’s fun to kind of take a trip through having known you for a long time and sort of see this lens into your career, and it’s awesome to see all the great things you’re doing at Microsoft. So, appreciate your time today.

Matt Fleckenstein (28:38): Yeah. Thanks, Sean. Look, I greatly appreciate it too. Love your podcast. I think it’s the type of stuff, there’s not great information out there about corporate ventures and entrepreneurial stuff, and so love what you’re doing, and love Agile Giants. I look forward to hearing the upcoming season.

Sean Ammirati (29:03): I hope you enjoyed this episode of Agile Giants. If so, consider sharing it with a friend. If you think it’s worth five stars, which I hope you do, please go to iTunes and rate it so that others can find this content as well.

Join the discussion

More from this show


Episode 24