‍Rachel Chalmers:

Today, I'm delighted to welcome Ian Bergman to the show. Ian is a startup advisor, investor and self-described corporate innovation agitator. He's recently a 14 year veteran of Microsoft, where he worked in partner channel strategy, hardware planning and engineering, and Azure Cloud, before finishing as Global Managing Director of Microsoft for Startups, overseeing startup acceleration, global innovation, and engagement with Microsoft startup ecosystems around the world. Before joining Microsoft, Ian co-founded the political news site Raw Story. He has an MBA from the University of Washington and a BA in politics and French from Oberlin College. Ian, it is so great to have you on the show.

Ian Bergman:

Oh, Rachel, thanks. It's so awesome to be here. Thanks for having me.

Rachel Chalmers:

Microsoft was once notorious for squishing any startup around it, a reputation it's managed to more or less entirely reverse in the last decade. Tell us more about your role with Microsoft for Startups and what that was like.

Ian Bergman:

Wow, I love that question. It feels like a loaded one, but it's a great place to start. I'll say I'm glad to hear you say this, even from your seat at the heart of Silicon Valley, that the company has managed to reverse that reputation. This is a bit of a two part question. Microsoft and how everything that it does is perceived in the world of tech startups, Silicon Valley, and global, and then the particular work of Microsoft for Startups organization. Historically, there's so much that fed into this idea of Microsoft as this villain that would, in your words, squish any startup around it. You can go back to a long period of blatant antagonism to open source, to business decisions like the integration of Internet Explorer into the Windows platform, or even to the strength of the partner channel and pricing models that made Microsoft technology very hard to displace.

For some of the root causes, a lot of this reputation was deserved, even if it does gloss over exactly how powerful of a launchpad for startups open platforms like Windows really were and really are going back decades. Fundamentally, your question operates in a pretty broad context. Microsoft's reputation has recovered for a bunch of reasons. Completely embracing open source, new leadership that's allowed latent cultural desire to do good in the world really flourish, a deliberate internal push to embrace a culture of innovation. It's hard for me to overstate how many times I heard the words “growth mindset” in my last few years of the company and reinvigorated and proactive developer relations.

Things like the launch of Microsoft Ventures now M12 and better products. Azure, for instance, just got a lot better over the last few years. One of the other things that has been happening and it's really important not to understate the importance of this, is this continual loop of engineers, executives, marketers, and Microsoft employees who learned a lot at Microsoft found some problem in the world they wanted to solve and were left to do their own thing. To found a startup, a VC fund. They were out there living the world of startups, but they kept in touch with all their buddies at Microsoft, and they said, “Hey, here's what you're really doing looks like from the outside? Can we maybe chat about this?” Such a large chunk of the Seattle venture capital and technology startup scene was catalyzed by this outflow of talent from Microsoft and a couple of other big players, and that meant that there is this startup culture that was sitting right there at home around the company.

There's a lot of context that has gone into helping the company deliberately act to recover its reputation. It is important to note that for over a decade, the company has been pretty deliberate in trying to position itself in a way that's nicer and more collaborative. Particularly the collaborative piece really has resonated in startup communities around the world. So much of building a startup is such a team effort. The other thing that drives reputation is the actual experience of working with a company. Meaning, what is it like as a startup to work with a company like Microsoft? And that's where, honestly, Microsoft was frankly lost for a number of years and that really, really damaged the company's reputation.

We didn't have a strong point of view on why a startup would want to work with us, and because of that, startups didn't know what they might get from working with us outside of some optimism that they might be acquired or because for whatever reason, something they were building took a hard dependency on the product stack. We found ourselves at Microsoft with a super transactional relationship with most of the startups that we worked with. A relationship that boiled down to, “Hey, here's some free tech. I hope you like it because at some point the bill collectors are going to show up and we'd be just chuffed if you'd go ahead and pay for it at that point.”

How do you build your reputation in the startup community with something like that? You might not hurt it, but in a world where startups, at least those with access, are just a wash and people offering to help in a million ways, you don't stand out. That was an issue not just for reputation, but for the core business. I don't think it's any secret to say that in the late 2010s, Microsoft was a very, very distant second place in terms of being a tech provider of choice to startups in any workload, cloud, compute, collaboration, productivity, you name it. That's kind of an uncomfortable place to be when you believe that you're one of the most important technology providers in the world.

Rachel Chalmers:

What you're coming second place behind is a Seattle based bookstore.

Ian Bergman:

That's right, a Seattle based bookstore or a Silicon Valley startup or a Silicon Valley former startup. We didn't have the market share we wanted. The reputation wasn't what we wanted. And frankly, and to put it mildly, the economics of the business were rough. What we did when launching Microsoft for Startups was to do exactly what any startup should do, we did customer discovery. We just went out and talked to a boatload of CEOs, CTOs, investors, advisors, anyone else we could grab off the street to try and figure out what they needed. We asked ourselves what we felt that we at Microsoft had a native right to be good at and develop some hypotheses as to why that would matter to startups. What we realized is that we could distill down the needs of most early stage startups to four things. This will be obvious to all of your listeners, but access to talent, access to capital, technology, and customers.

While we could in some cases, help with access to talent and capital, after all, Microsoft has LinkedIn, Microsoft has M12 and partner relationships with lots of investors. And while we were one of a very small number of truly global scale technology providers, the thing that we could do uniquely, we had a very unique capability in terms of our access to customers. Microsoft has a relationship with a pretty significant percentage of the businesses on the planet, and it has a pretty unbelievable and consistently underestimated distribution channel through its partner network and salesforce. We sat there thinking, well, startups need customers. Our customers are struggling to stay competitive and innovative in a changing world that was sort of the foundation.

Rachel Chalmers:

I'll never forget going to one of the big Microsoft partner conferences in Chicago, and it must have been 2014 or 2015, and there were one hundred and forty thousand people there. I've been to Google Next. I've been to the Big Apple technology conferences. I feel like I'm cool in Silicon Valley. You walk into Chicago and there's one hundred and forty thousand I.T. Directors from Midwestern dentists offices and insurance chains. I had no idea, even working for Ignition, which was one of the Microsoft veteran founded VC firms. It's really hard to see from the valley where Microsoft's strength is and it's in the SMB and the enterprise, and it's almost imperceptible to the Googles and the Sandhill roads.

Ian Bergman:

It's so true and it really is mind blowing, and it's fair to say that the secret sauce behind most of Microsoft's success over the decades has been that access to distribution, that access to customers and the business models that work for them. There's some amazing products and there have been some let's call them stinkers. But fundamentally, that's the secret to success. Building on that, what we launched with Microsoft for Startups was a very focused program to help B2B startups get access to Microsoft's customer and partner base. It came with all the usual stuff: cloud credits, tech support. But what we layered in was an entire program designed to get those startups qualified leads and deals through our channels.

I used to say that the number one KPI for my team was the dollars of revenue achieved by startups in our program through Microsoft. It had nothing to do with Microsoft revenue. I can't remember what the latest public number was, but we're talking billions of dollars of pipeline for the startups, which is meaningful. The idea is a real partnership, not a vendor relationship. When it works, it's really obvious to the startup and also to the startup’s investors and stakeholders because you're growing top line revenue. You're going beyond proving product market fit and you're actually starting to achieve scale. It takes years for this sort of effort to have a material reputational impact, but I do think it's helping. My role as Global Managing Director was basically to develop and run the team that was out in the world doing a bunch of this work, recruiting startups, helping them develop their product, helping them grow sales capacity. We had staff in something like 15 or 20 countries and operating in many more.

What's interesting, is because we were really operating at that intersection of the needs of startups and the needs of companies, trying to figure out how to fold startups into their innovation efforts, we got to experiment a lot in terms of how to help these larger companies, these mid-market firms, these enterprises, get the most out of working with startups. Because this is a playbook that is still yet to be written. We did things like set up our offices in the places that startups and corporations meet, like Mars in Canada, Station F in France, Hub Seventy One and Abu Dhabi. We ran programs like A.I. Factory in Europe, where we worked with companies like Danone to help them get to pilot successful pilots with a group of top AI startups. China team is just a wash in attempts to connect big brands with innovation there.

All of this has an intention of achieving that win-win. Helping the startups get access to customers, but really also helping these customers in every sector get the most out of their access to entrepreneurship ecosystems. The last thing we did, which is, worth talking about because it's something that  any startup also needs to be good at. We got really good at saying “no”, a lot. “No, we're just not the right fit for you”, which is very important and from a reputational perspective over the long term, does help because we're trying not to waste everyone's time.

Rachel Chalmers:

You put your finger on something that's really key to the work we've been doing here at AlchemistX, which is that enterprises really are in this bind. They have to innovate in order to survive. Sandhill is funding ten competitors to disrupt them every day, but as an enterprise, you have a set of survival strategies that have served you very, very well, and it's really hard to move away from those without actually cannibalizing your own business. So are there corporations you think are doing a particularly good job with innovation and even more interestingly, are there any corporations you want to call out for doing a bad job?

Ian Bergman:

I don't know that I'm going to get into naming too many particular examples, but there's some really interesting stuff here. We need to separate fundamental world changing Silicon Valley disruptive innovation from equally important but maybe less disruptive constant improvements that are out there. There are very, very few established mature companies that get the insight and the opportunity to do something fundamentally new. Even fewer get to do it twice. This is where I have to go to these super well-trod but important examples like Apple, with the launch of what became the iOS platform, or maybe Amazon with what became AWS. I realize I just picked two U.S. West Coast tech giants, but the interesting thing is they were both founder-led at the time. Tons of ink has been spilled on each of them figuring out how they built something new, disrupted a market that was that looked at least on the surface, to be different from their core business. And that ink has been spilled because it's so rare.

There are a lot of companies that do fundamentally a pretty good job of innovating within their own product categories. We could look at restaurants like the launch of Panera a while back or insurance or beverage brands or CPG like Procter and Gamble. With my experience being mostly in tech, I'm trying to avoid just listing off a set of tech companies. But there's a lot of companies who do a good job of managing to iterate their product to keep it relevant and fresh and call it innovation. This can work right up until there's a fundamental change or a fundamental disruption, a change in consumer behavior, some new concept.

The interesting thing to me is that most of the time that fundamental change is coming from something that looks a lot like a startup, a new company. SpaceX seems to have really nailed reusable orbital launch hardware. Stripe and Shopify have made so much of the hassle and pain of shopping disappear. Those are three companies that begin with ‘S’. Spotify, let’s add a fourth, give music to folks in a way they didn't realize they wanted. I don't think and I haven't really met very many people who would think that this trend, this, that fundamental change is driven by a new company, not with an existing one, is going to go away any time soon. And so in my mind, some of the companies to work my way back to your question of, who's doing a good job with innovation.

The ones that are doing the best job with innovation are the ones that are trying to be very, very deliberate in terms of how they stay connected to global entrepreneurial ecosystems. Sandhill, the venture community, Silicon Valley, but equally, the ecosystems around Toronto, London, Medellin. These are some examples. I've been particularly impressed in a way that surprised me, but maybe shouldn't have with some companies in the insurance sector that have been very, very deliberate at putting in place not just venture investment arms, but build studios pilot opportunities with startups. I've had a chance to work a little bit over the years with New York Life. There's some others.

Rachel Chalmers:

I’d call that State Farm as well, they saw AVs coming long before I took them seriously.

Ian Bergman:

Yeah, that's right. Some of the big financial firms, like your Chases of the world and Bank of America have pretty big investments in this space. So I'd say there's a bunch of companies that are trying and succeeding in many ways at using connections to the startup ecosystem for a combination of insight and market research and strategic access to companies down the line. You see lots of disconnects between sort of ambition and execution and all that. Maybe I'll give a personal story from my family as an example of an entire sector that can do a better job. Rachel, as you know, my family recently moved from Seattle to Vancouver, Canada.

Rachel Chalmers:

Thereby giving your native niceness its natural spiritual home.

Ian Bergman:

Exactly. That's exactly the motivating factor behind the move. One of the things that I was pretty stunned to observe in that process is what it's like to do banking in Canada. The fact that it's pretty hard to do most interactions with a bank without walking into a bank branch. It's in fact almost impossible. I don't think I had been in a bank branch before my family moved, I can't even count how many years. This is just one of those examples where it will change but there's latency between expectations of consumer behavior because the expectations of the Canadian market are no different than anywhere else in the world in terms of how they want to get access to financial services. And some of what you talked about institutional momentum on everything from regulatory and safety issues to we just haven't caught up with how we can do a good job keeping up with the pace of change. 

Rachel Chalmers:

What's funny is I had the reverse experience moving from Australia to the U.S.. Australian financial services were pretty advanced in the 90s. I didn't have a checkbook until I moved here. You could use an ATM card for all kinds of transactions, and I was like, I have to sign my name on a check, bring me my quill pen and my snuff box.

Ian Bergman:

It's crazy, right? And actually, you hit on a pretty interesting point there. For decades, we've all been aware of an increasingly globalized world and the pace of communications and ideas moving across the world. TikTok can spread an idea around the world in what feels like seven seconds. What's interesting is that innovation needs to be globally sourced because it's responding to globally sourced changes and consumer expectations, availability of new ideas, et cetera. That's happening faster and faster. It goes in every direction. It's an infinite matrix of ideas coming out of Singapore or Sydney or wherever and going somewhere else in the world. It’s actually fascinating.

Rachel Chalmers:

Submerging is sort of a core principle of all of the AlchemistX programs that we run. The capital and the methodologies might be here and in Silicon Valley but the talent and the ingenuity and the demand are global. They're distributed everywhere, so it informs a lot of our work, particularly with the regional governments.

Ian Bergman:

That's awesome to hear, and it makes total sense. I've observed something similar. You get these hubs of talent that are locked up in a large corporation, a bank or an energy company. They want to and eventually do burst out. Then you get these new innovation hubs where new ideas will spread from places that feel really unexpected. I know this is a little bit of a tangent, but I was talking to the founder of a startup just a couple of days ago from Houston, which is one of these areas that I've long thought is wildly underappreciated on its entrepreneurship potential because it has the big companies, the universities, the engineering capability. I think all of us who are in this space are well served to look globally and to look at what the connections should be between San Francisco and Houston, between London and Seattle, between Tokyo and Sydney, whatever it might be.

Rachel Chalmers:

Houston and Sydney are particularly interesting because as with a lot of the clients we're working with, the economies are primarily based on extractive industries and minerals. Even these economies, which you would think would be super conservative, are starting to acknowledge that climate change means they're going to have to transition away from fossil fuels. We're seeing a lot of energy and money behind this shift away from resource based industries to information based industries, which is fascinating. It's a really interesting time.

Ian Bergman:

So glad to hear that. It’s reassuring among some of the scary things going on in the world.

Rachel Chalmers: 

There's going to be a lot of heavy lifting to make it happen.

A question that I ask all my guests because the answers are invariably interesting. What do you think makes innovation so difficult? 

Ian Bergman:

I love it. It's a great question, and I suspect there's probably a 60 percent overlap with so many of your guests, and I'll hit on some of those. But it's the differences in the answers that are probably really fascinating. There's a bunch of stuff. One, new ideas are hard. Executing new ideas are harder. When I think about what makes innovation difficult for, let's call it, established companies, organizations that have a purpose and a business that they've been executing. I kind of break them in my head into two buckets. There's what makes it hard for product companies, some companies that build something and what makes it hard for everyone else. There's a few things that come to mind.

One of the most dangerous for product companies is the not built here mentality. The inherent belief that because we know our business and we can build everything ourselves and we don't need to seek out talent and ideas from outside the organization. This gets in the way of so many companies. I have seen this and lived this in my career at Microsoft. You see it again, in insurance and banking. Imbuing a company with a culture of innovation requires that step of acceptance that we can't do it all ourselves. And in fact, we shouldn't be able to do it all ourselves. Nobody can, and we need to recognize that. So they're not built here, mentality and the culture around it. Another common cultural blocker is a lack of a culture of risk taking. Innovation is literally learning from failure over and over and over again, and some companies have packaged that up into a machine. Let's go back to Proctor and Gamble, and the CPG development pipeline and other companies that struggle. Organizations in my mind that for one reason or another aren't able to reward the lessons of failure really struggle.

Those are pretty general blockers. One of the things that is changing in terms of what is making innovation harder these days and what is making a lot of companies that have traditionally been very good at keeping up with their consumer base is just the pace of change in the world around us. It could be unexpected systemic shocks like people working from home all of a sudden because of a global pandemic or it could just be cultural trends that are spreading more rapidly through the internet than they ever have before. It's just becoming really hard to keep up, not just with technology. We're well past the point of talking about companies having to modernize their I.T. infrastructure and software and digitization, but the pace of change in everything in the world, you just can't wrap your head around it.

It's all changing really, really quickly. If you don't have mechanisms that let you really deliberately and successfully listen and observe and learn from what's happening around the world, your hands are going to be tied in innovation because you're going to be solving a problem that might be a month old or a year old. That one's tough. This is where I just come back to seeing so much opportunity for most companies in the world to get better plugged in to what's going on in the world of entrepreneurship, because that is literally a nonstop cycle of testing ideas that everybody can learn from.

Rachel Chalmers:

This is where I've become just such a profound zealot for customer discovery because it's great for both sides of the interview. Startups conducting customer discovery are doing exactly what you did and going out and talking to customers and finding out what's on customers minds. But when a startup engages that way with a potential customer, the potential customer also gets the opportunity to see what the startup is working on and reflect on potential changes on how processes could be improved and optimized within that organization.

Ian Bergman:

To build on that, the constraint of domain expertise, that's a real blocker for so many people, they are experts in what they do, therefore they know how to do it, and it's really hard for them to see a different way. Those sorts of conversations that maybe open up a domain expert to some insight that they would never have otherwise had or in any way let a person or an organization lift themselves up out of what they assume they know. That can be a real accelerant for, I'd say, successful innovation. So yeah, I get it. That makes a ton of sense.

Rachel Chalmers:

Which is a great segue into the next question, what are some emerging best practices for corporate innovation and how can we propagate them? 

Ian Bergman:

It's the million billion trillion dollar question. I will say the thing I love about that question and actually about this whole conversation, about connecting startups to the world of corporate innovation is that I actually really don't think it's rocket science. It's hard. It takes a certain amount of willpower and one of the hardest things, a certain amount of patience and persistence to lift yourself out of perhaps sort of quarterly reward cycles. But it's not rocket science. I do think there's a couple of best practices that I've seen when I've talked to folks who feel like they have a base of success and they're getting some stuff nailed.

The first is around the team. Who do you put on your innovation team, particularly if you are expecting a good chunk of that innovation to come externally from outside the company? This is where diversity of background and perspective is so important. Diversity as a rule is always important. We know that as a general statement, teams made of diverse backgrounds will achieve better outcomes. But in the context of thinking through innovation and connecting to startups, one of the mistakes that I've seen a lot of companies make is stack their organization with a bunch of like minded folks. 

It tends to be either the banker investor types. Which again, can make a ton of sense. You might be doing it, you might be driving this aspect of innovation through the lens of corporate VC. Or it tends to be a bunch of product types who are experts, and you're going to skew your exposure to innovation if you don't have a diverse team. You can run an extraordinarily successful corporate venture program, for instance, that returns significant returns to the treasury, that gives you line of sight to strategic acquisition targets and yet miss a fundamental shift that all of your product leaders need to know about because you don't have product people on the team that are connected back to the business.

Rachel Chalmers:

That's where we call on Kodak. The canonical example.

Ian Bergman:

Wonderful example. Talk about a fundamental shift that, hindsight being 20/20, they should have been ahead of the curve. I still remember my first and only Kodak digital camera, did have one. It was fun.

Rachel Chalmers:

I did want to call out an anti-pattern to your point on diversity. I remember a startup in the valley that had a nice office, and all of the PhDs in computer science got window desks and the people who merely had a master's in computer science had to sit on the inside. My blood ran cold when they told me this.

Ian Bergman:

Not being intentionally diverse and inclusive in all aspects will hurt you because you don't know an innovation where the idea is going to come from and how you're going to connect it. 

Rachel Chalmers:

I'd say it's even deeper than that. I'd say those of us who come to the job market with a lot of socioeconomic and educational privilege, literally playing life on the easy setting. Thanks to John Scholesy for that vivid metaphor. When you encounter a black person or a LatinX person in the workplace, you know they've had to work twice as hard, three times as hard to get there. What we're really talking about are moderating conversations, creating spaces for exchange. People from underrepresented backgrounds have so many more skills in navigating those difficult areas of conversations. All of the things that we deride as soft skills, I would say are core skills. If you've got a person from an underrepresented background succeeding in the tech industry, they are oversupplied with those skills. And if you don't bring them onto your team, it's your loss.

Ian Bergman:

I can do nothing but nod and agree from lots of lived experience. That does sort of connect to the second thing that is more of an emerging best practice and a little less proven out, but one that I fundamentally believe in for corporate innovation. The missing piece for so many companies is the facilitated connection between something happening outside, say, a startup in the ecosystem and pilot and trial in their core business. How do we really seamlessly get this thing that seems like a good idea into the hands of people who can beat on it, learn from it? How do we have a robust system that's trusted within the company that results in pilots that results in trials and that importantly, it results in an ability to make a decision ahead of the typical corporate development curve in terms of, do we like this tech? What do we want to do with it? Do we want to partner with them? Do we want to buy them? That's a big missing piece for so many companies, and the companies that have nailed all the aspects internal and external of how to get this stream of adjacent innovation into their core businesses, they're the ones that we're seeing do the best job staying ahead of the curve.

Rachel Chalmers:

It really does seem like the most highly leveraged affordance. If there's one variable that you can change in all of this complexity. If it's just compressing the time between encountering a new technology and figuring out whether or not you can derive value from it, that is the one thing that can make a corporation more competitive.

Ian Bergman:

One hundred percent. We were talking about how it's not rocket science. Simplicity matters here, right down in five bullets, how you're going to do it in your company. And there's organizations that can help. There's best practices to look at, but simplicity matters and just try.

Rachel Chalmers:

My friend Peter, the rocket scientist, likes to say rocket science is not rocket science. You have fuel and you have a nozzle. Point. Go. It's the same math.

Ian Bergman:

It's so right, and it leads to this point. Don't be afraid of it. Just try it. Try and learn and innovate in how you do innovation. It's going to sound silly, but I actually do believe this. There's a realization that a lot of companies come to, it's easier to get somebody else to do the hard work of innovation for you than it is to do it yourself. Open your arms, open your doors, welcome them in a way that makes sense for everyone and go. Look, obviously every company has their core capabilities. I'm going to MBA you your core competency. For everything else, don't overthink it. Just open your doors and see what happens.

Rachel Chalmers:

It's a reason outsourced innovation has been such a massive engine in the valley, going back to Fairchild and the traitorous eight. It's because it works. You just have a ragtag band of engineers, leave and start a new company and get acquired and leave and start a new company. It's an incredibly effective way to create new structures.

Ian Bergman:

Well, that's awesome, and I can't wait to see more and more of the world realize that. Can I share a little story?

Rachel Chalmers:

Of course, that's what we're here for.

Ian Bergman:

Everybody has these seemingly innocuous conversations that they can never shake. One of mine in this world was with a small startup out of Central Europe. They were building what seemed like a very innocuous product. They were building a smart light bulb for chicken coops. This is a space I know absolutely nothing about. We got to chatting and I went into this conversation thinking, I don't even know how we're going to have a conversation here. I don't know anything about raising chickens. I know a little bit about smart technologies that are in your light bulb. But we got to talking. What this company was building was something pretty simple. It is a light bulb that anyone who raises chickens knows how to screw into the standard industrial light bulb socket in their chicken coops. And it's got a few cameras on it and an LTE modem and a little bit of edge processing capability. Its promise is quite simple: you screw this thing in, and by watching the movement of the chickens in your chicken coop, we might be able to predict the outbreak of disease earlier, faster and more effectively than the farmer can do it when they are going through.

Honestly, I have absolutely no idea if this worked the way I promised. But the interesting thing is that that product, if you look at the concentric circles of impact it could have in the world, it starts with maybe making a farmer's life a little easier, maybe saving them some time once they're reassured that they don't have to do as many manual inspections That's a nice little value proposition.

Then you think through what is the impact on logistics if you're actually getting ahead of disease, are you being more predictable in the output of eggs, for instance, from your farm, and you can do a better job of booking shipping containers in advance? Or what about pricing risk for the insurance that covers loss of crop loss of disease? It's one little example you start to follow it out. You start to see how a really cool little technology, if it works well, can impact a bunch of companies in ways they neither expect nor are looking for. It's always stuck with me because I've always thought there are very few insurance companies on the planet that are seeing something like this coming that might completely change how they have to price risk in agriculture. I find that stuff really, really fascinating. I can't even remember what it was you said that prompted me to get on to that story.

Rachel Chalmers:

My favorite one of those, though, is Craigslist. When we moved here to San Francisco, it was absolutely invaluable in finding us a house. I was at the time a journalist who had been working for newspapers. You and I were talking the other day about how my first newspapers actually used Hot Metal Type, and I watched the newspaper industry collapse because all of their classifieds revenues got eaten by Craigslist. It was such an innocuous 90s internet site. It transformed how these massive multinational media empires derive their revenue. it's fascinating.

Ian Bergman:

A seemingly unintended consequence of what it was really out there trying to do, which is make life a lot easier for a bunch of people trying to communicate classifieds.

Rachel Chalmers:

Now we completely have to rethink how we keep the population informed about important issues.

Ian Bergman:

I know and we all want to stay ahead of this stuff because getting surprised by it is not fun.

Rachel Chalmers:

It'll be fine. It'll be fine. We'll figure it out.

That's a great segue into the next question when you look back on your career to date, what are you proudest of?

Ian Bergman:

This is going to sound a little orthogonal, but I'm just personally motivated by opportunities to touch a lot of people in a small way. I've been really lucky to have had a few opportunities like that in my career. I'm going to take one out of left field, touch screens on laptops. I spent two years of my life along with many, many other people at Microsoft, around the entire world, working on this problem. One of the things that I did is run a little bit of research that basically said, this is a good idea. People will generally be happier if we do this thing that nobody is asking for.

Through the efforts of an entire ecosystem and industry, there's a lot of Windows PCs in the world that have touch screens on them. And there's a lot of people who use them even without knowing it and are happier because of it. And you can measure that because of their lack of happiness when they're forced to use one without it. I love that stuff. I love when you can do these little things and you realize that it just propagates out into the world in partnership with a bunch of people. I don't know if proudest is the right word. I'm really proud of the work we did at Microsoft for Startups. I'm really proud of building a career of being a relatively competent generalist. I think that's a good one.

Rachel Chalmers:

It's the blessing of having a liberal arts degree. We can't over specialize into anything because we're too curious.

Ian Bergman:

That's a good way to put it. We're too curious to go deep and actually learn how to do math well enough to be a specialist.

Rachel Chalmers:

I love that framing because not all of us get to be Obama and have a big global political impact. But we all have this opportunity to nudge things a little bit into directions that are more usable and more accessible and more compassionate and fairer. Framing our career accomplishments as I had the opportunity to nudge the world just a little in the right direction is a really humane one.

Ian Bergman:

Well, it is. We all have the opportunity to identify and hopefully we achieve identifying that thing that gets us up in the morning and then framing your career around it. For me, it's those downstream impacts to lots of people, lots of people motivated by different things. That's what is one of the fun things about this world that we operate in. It's hard to do, but we all have the opportunity to identify what motivates us and how it's connected to our daily work and when we can frame our career on that, you're going to have stuff you're proud of and then you're probably going to have some stuff that you're not so proud of.

Rachel Chalmers:

If you had one do over, what would you do differently?

Ian Bergman:

I have such a love-hate relationship with questions like this because who knows? If I did it differently, would it turn out any better? There are some things that maybe don't haunt me, but follow me around. It certainly took me a while in my career to figure out how important it is to fail fast on a bunch of stuff. Having a bad hire is something I've done once or twice and not failing fast, that's a lesson. That's a career lesson I give to lots and lots of people.

There are a couple of other career lessons that I've internalized, not necessarily as do overs, but if I went back, I would behave differently. One of them is just being at the table and another is absolute accountability. One of my favorite managers and now mentors from way back when, I was having a tough conversation with her a number of years ago. I was doing a lot of whining about why the outcomes of a particular decision hadn't really gone the way I thought they should and what that impacted me and blah blah blah lost in my own self there. She said, “Stop for a second. Were you sitting at the table?”

She meant this metaphorically, but also actually quite literally physically, were you sitting at the table? It was a table full of executive vice presidents, and I was sitting in a chair behind them early, mid career. She looked at me, “Why aren't you at the table?” And this lesson that we all have a right to be a participant in the conversations that we have a right to be a participant in and just go for it. I actually think about that a lot because there's a bunch that I would have done particularly not just early in my career, but my personal life and other where if I had internalized that I’m there for a reason, jump in, speak your mind, it's OK, don't be an a-hole about it.

Rachel Chalmers:

That's such a powerful moment. It's so important to give people their voice in that way to let them find the issues that they have strong and well-founded opinions on and say that is valuable. That is important. You've got to speak up.

Ian Bergman:

It's so hard for so many of us. It's still hard for me. I think about it all the time, but it doesn't mean I'm good at it. One other practical and on topic thing just occurred to me. I wish you could go back in time and actually take this core lesson that it's OK to look for ideas and innovation outside of your context back into some early career. There was a point in my career where I was running what was effectively a research team. It was effectively an innovation planning team. So much innovation inside big companies and certainly what we were doing was crystal ball gazing. We'd look at research reports, talk to some folks and trend, we try to draw a bunch of lines, see where they converge sometime in the future and use fancy sounding tools like backcasting to figure out how to go from where we are today to where we wanted to be.

That process and those tools, they absolutely have their place. They're actually very, very powerful for building product roadmaps and vision for teams and all that good stuff. But it doesn't lead to the sort of intuitive and cognitive leaps that result in real disruption or something really materially better. It tends to get you incremental improvements. So I wish that I had really thought about that 10 years ago when I was doing this kind of work, I would have researched differently. Everyone in the world during your career, you’re given lessons that would have made everything you've done before better. But that's actually one that sticks out. It's on theme because I really just have internalized this belief, look outside for a bunch of ideas as well as look inside and then put them together and see what happens.

Rachel Chalmers:

I love the entire design thinking toolkit, but if I had to throw out all but one and start again with one, it would be to the Discovery interview because you can reconstruct everything else from that one.

Ian Bergman:

That's awesome. If you have thrown everything else out, not saying it's a good idea for everyone, but if you do, you've got a bunch more time. Do your discovery and then think about whatever it means to you.

Rachel Chalmers:

In some ways, it's the cognitive equivalent of just walking away from a decision and then finding the answer in the shower the next morning. You've got to give yourself the gift of serendipity. You've got to give yourself the gift of juxtaposing apparently unrelated ideas to find that connection.

Ian Bergman:

I am totally stealing that line at some point. Giving yourself the gift of serendipity. We talk about casual collisions and serendipitous meeting of minds in group contexts, but doing it in your own head, that's awesome.

Rachel Chalmers:

How would you distill your experience into, let's say, two or three lessons for our listeners?

Ian Bergman:

The first one is actually really funny because I guess this is one where I'm following my own advice. I often tell people to just “Write it down.” If you haven't written it down, whatever it is, nobody else can interact with it, test it, internalize it, argue with it. And it doesn't matter. I actually believe that is a general lesson, but I also mention it because I've written down some of these lessons. I really do believe in the importance of knowing what you're good at and maybe what you have a right to be good at. I believe in the importance of taking the time to really think about that, and I know we've talked about that a little bit, but it's a step that people and organizations skip so often.

Without that journey of self-discovery, one, you might miss something you'd otherwise learn. Two, you don't have a starting point for the work you're going to do. It's really important to be self-critical, but to own what your strengths actually are and how they map to the needs of your customers, look where they meet product and profit.

Rachel Chalmers:

I'd say that's not just about deep domain expertise, it helps, but it's not necessary. It's about what you really care about. If you're advocating for a specific customer set and you think that they're being overlooked in product development, that's when you should speak up. When you have that lived, manifested conviction of what is the right way to do a thing. It doesn't matter how junior or senior you are, you should be able to speak up.

Ian Bergman:

Absolutely, so important. I've got this long list, but this is one that I get into arguments about all the time so I like it. I have so much lived experience that tells me that secrecy is wildly overrated. I've been through the ringer on NDAs, confidential products within a particular team. Talking about patents and every aspect of this. Microsoft has this concept called Tents that lots of companies have. Little domains of absolute secrecy. I've been through the ringer on these. I struggle to think of a single time where I have put effort, real effort into keeping something a secret and come out into the side and thought this is resulting in a better business outcome. I built an entire tool once about seven or eight years ago to help us track the distribution of secret documents that we were sharing with partners.

We put so much time and treasure into this effort, and when I look back on it, it was wasted. I by no means dismiss the importance of patents and trade secrets from any businesses. They have their place, but it's often worth us all testing ourselves. We can't talk about this because it's confidential or I'm going to put a bunch of time and money into making sure this doesn't leak out. It's often worth asking the question “Is this really worth it?” Because we spend a lot of time trying to keep secrets that everybody else looks at.

Rachel Chalmers:

In the worst case, it can actually seriously disable your business. And I can't remember if I shared with you the article in Slate recently, which was a 20-year look back at Ginger, which became the Segway. The conclusion of the article was, it would have been nice if they'd done some customer discovery with this before they did all of the secrecy and then the big launch. It's a fantastic article. It just makes me chuckle because everyone's running a secret project and when they secretly let you into the secret project, you're like, I've seen ten of these already this week. It's all about execution.

Ian Bergman:

Amazing. I totally can't wait to read that. Secrecy has its place. Be deliberate about it and thoughtful because nine times out of ten you're wasting time. 

Rachel Chalmers:

Ian, how do you avoid burnout?

Ian Bergman:

Boy, that is topical and timely. I haven't always. I've been on the edge a few times, mostly in my professional career, not my personal life, and it hit me once. It hit me hard in relatively recent memory. And it's awful. I'm normally a very optimistic and energetic person, glass half full, whatever psychological profile you want to run, it always shows me as having kind of a disturbing level of optimism around the world around me. I've gone to dark places because of what can only be described as burnout. People are affected by this differently, and they find different coping mechanisms and ways to deal. But for me, it's when I've let myself be controlled by forces around me that feel out of my control. Being accountable to too many people and trying to please a bunch of people without letting myself have the authority to make hard decisions and control my environment.

I went through a phase in my career where I had far too many direct reports, a team trying to do far too much, where I felt like I was accountable to the success of too many people around me, and I was just trying to juggle it all and no one can. And it led to real burnout. There's a few things that I try to do. I never want to get there again and to just control burnout and the balance of my life. One of them is being deliberate and what I commit to and what I let myself emotionally feel accountable for. And then making the decisions I need to make to not let myself get burned out. I have had moments in time where I have waited months because I felt like a manager had to make a call for me on some options I was presenting.

The other thing that I do, and this is what I've always done in my career and personal life too, try and make sure there's a balance. I just block time in my calendar. Sometimes it's for meetings. Sometimes it's for having a date with my wife. Sometimes it's for email, but I try to be deliberate because that's my way of knowing how I'm distributing my committed hours. If I can't fit my work or my personal life or something else and the allotted time, then something's going to go wrong eventually and something's going to break. Oh, and breaks. I am fastidious about taking breaks. I have been in teams where when I go on vacation and don't check my email, people look at me like I'm crazy. If you're not letting yourself refresh and reinvigorate in whatever way works for you, what are you doing?

Rachel Chalmers:

The calendar blocking one is so powerful. That was when I learned in my 30s, particularly if you're responsible for any kind of creative work, you have to put all of the interrupted bits into one section of the day and block out the rest of the day because you cannot write or create or code or get into any kind of flow state if you're in and out of meetings all day. That's the tactical side. The strategic side is if you don't have the autonomy to organize your calendar that way to push back on requests that violate your calendar scheme, you've got to get out of that environment and into some other environment because what is causing the burnout is the loss of autonomy, the lack of agency.

Ian Bergman:

You're so right, the conflict with the desire to have agency. You can avoid burnout by simply following someone else's script all the time that fits within a certain domain. And honestly, if that's great for you, then that's great. If it's not your job to follow someone else's script or if it's not your driver in life, like you said, that disconnect between agencies is real and there's a little bit of self-realization that you just got to do in there if you're worried about burnout. 

Rachel Chalmers:

This is where the horses have been a real advantage for the last 10 or 15 years. I've just put them on the calendar during the work week, “got to ride my horse.” And when Ravi catches me, I missed a call from him because I've been at the barn and he's like, “Oh, good for you, I'm so glad you did that.” That's what you're looking for in a boss.

Ian Bergman:

It's so good. To a lot of people, this sounds dreamy or hypothetical or idealized, but it's not. Anybody can choose to figure out what lets them recharge and make time for it. I wish I had your discipline at blocking time for the horses. For me, it's blocking time to take a hike. When I look back on this summer, I took 11 hikes. That's not what I intended to do, but even those 11 helped.

Rachel Chalmers:

Two things about that, one is that the horse has to get out, so you've got to do it. It's keeping an animal. The other thing is why hike when you could sit on a horse and have a horse hike for you? Pure laziness on my part.

Ian Bergman:

I love it and I want to disagree with you. But I actually love being on a horse. I just don't happen to own one or have the competency to do so.

Rachel Chalmers:

Ian, what is the best way for our listeners to connect with you or follow your work?

Ian Bergman:

Thanks for asking this. I am so terrible at operating in the public eye. There's not a great way because I have been so poor at maintaining a public profile, but there's a couple of things. I occasionally reluctantly shout into the void that is Twitter, mostly about what I'm yelling at the TV about my soccer team, Sounders FC or some other random topic. Anybody can follow me on LinkedIn, where I do post and comment occasionally on topics that I find interesting, particularly in the world of corporate innovation. I'm going to take your question as a prompt to do a better job of publishing on that platform. I long ago gave up on the blog, the medium post, et cetera, as something that I could move from ambition to reality. Linkedin is a tough tool in a bunch of ways, but it's a pretty decent publishing platform for stuff like this. So follow me on LinkedIn and engage with me when I'm shouting into the void on Twitter. Nobody ever does.

Rachel Chalmers:

On that note, what does the future look like for you personally?

Ian Bergman:

I am spending a lot of my time right now in various ways on that intersection of corporate innovation and startups. I like big, systemic problems that feel impossible to solve. It's one of the reasons I spent so much of my career at Microsoft, where little decisions impact millions or billions of people. For me, the big systemic problem that I would like to solve is this topic we've been talking about a bunch. It's that for whatever reason, most companies in the world are pretty piss poor at really taking advantage of the firehose of innovation coming out of global startup ecosystems. I'm spending time on that. I'm looking for opportunities to systematically change it, to build the patterns and practices that we talked about, the simple methods and playbooks that companies can follow, or maybe to make a difference for one company here or there. I don't know where that's going to go, but it is unbelievable to me how many people want to have conversations on this topic. Even people not in space. This is important to so many people in some way. That's pretty cool.

Rachel Chalmers:

As big systemic problems go, this may be one of the world's gnarliest.

Ian Bergman:

It absolutely is. Great use of the word gnarly, by the way. It's one whose time has come.

Rachel Chalmers:

It's five years from now. Everything in the industry has gone exactly the way you hoped it would. You are God emperor of technology, and all of the decisions have fallen your way. What does the world look like?

Ian Bergman:

Two years ago, I would have been talking on a talk track I'd had for a number of years about ambient compute and instant access to information and predictive knowledge because we'd have her whispering in our ears. Because I do think that's coming, it's all converging. Now, I'm humble enough to say I have absolutely no idea. I do think this is going to sound boring and staid, but I do think one of the things that will have changed because of technology is predictability and access to insight.

What I mean by that is predictability of outcomes, the ability to model outcomes to manage supply chains. Technology is enabling less of the uncertainty that we've become used to in the world. That's going to touch a million and it's super boring. But when I look at what's happening with predictive models, when I look at the infusion of repeatable, relatively easy to operate technology into areas like agriculture, like growing food, there's gonna be more predictability in the world. Our data tools are going to help us derive more insight.

Rachel Chalmers:

That's a great one and I would put it in the category of infrastructure, which is boring, but also profoundly interesting, because what that increase in predictability and repeatability is doing is it's intersecting with climate change and increasingly rapid political change and increasingly uncertain world, it's actually one of the most available ways to manage our risk going into a very scary future.

Ian Bergman:

There are scary elements to the future. The rapidity of all that stuff you just hit on. There’s a new Neil Stephenson book, relatively new, whose title, of course, I'm going to forget right now. It sets a near-future picture of where some of the forces we're seeing in terms of polarization and algorithmic control of content access. It paints a picture of where it might go. It's terrifying. I hope we don't end up in the world of Fall or Dodge in Hell. That's the name of the book. It's a wonderful, wonderful book by one of my favorite authors. If we do end up there, then I hope it's counterbalanced by predictability and infrastructure. How's that?

Rachel Chalmers:

That's an exciting note on which to end it. We have to invest in software and machine learning to avert science fiction dystopia and on that cheerful note. Ian, it's been a joy having you on the show. Thank you so much.

Ian Bergman:

Thank you. Yeah, it's been great, Rachel. I really appreciate it. I look forward to doing it again someday.

Rachel Chalmers:

Let's keep talking.