Paul Davenport:
Hello and welcome to What The Tech? from Boast AI, where we talk with some of the brilliant minds behind new and exciting tech initiatives to learn what it takes to tackle technological uncertainty and eventually change the world. Today I am thrilled to welcome Kenneth Berger onto the show. With 20 plus years in the tech industry, Kenneth helps startup leaders get unstuck and make their dreams happen.
As an executive coach to dozens of top founders, Kenneth shares the tools he's developed throughout his career to help leaders articulate what they truly want and take a courageous stand for those desires. He's a former founder in his own right, having helped create businesses backed by Andreessen Horowitz and Excel, and was one of the earliest key hires over at Slack, acting as their first product manager of Slack Group from a hundred thousand to 1 million daily users.
Needless to say, he's been on the front lines of technological innovation and behind the scenes of some of the most impactful brands of the 2000s, and I'm excited to pick his brain and share his insights with our podcast community. So without further ado, welcome to the show, Kenneth.
Kenneth Berger:
Thank you for having me. Appreciate it.
Paul Davenport:
Awesome. We're so happy to have you here. So for starters, could you tell me a little bit about your background and how you got into the startup space to begin with and the work that you're doing today helping out founders?
Kenneth Berger:
Sure, of course. So I started my career working at Adobe for many years and rode the big company lifestyle, but I ended up working on some of the big M&A deals that Adobe did, and it got me a taste of startup life. And I loved it, right? Of creating something new, working with a small team, making a big impact. And so I ended up becoming a founder myself, being early at Slack and riding that rocket ship.
And I think what got me into coaching was kind of this irony that I saw the highs of the startup experience, right? Of raising money and having customers and building a team, that sort of rocket ship growth. And I had all the pain, right? Of I had conflict with my co-founder, I had conflict with the CEO O at Slack that I work for, this tech luminary.
And there was a lot of heartache there, right? And a lot of worries about what does it mean for me about my financial future, about my professional future, right? All this sort of stress. And so when I came out of Slack, I had this thought of, "Well, okay, I can be a product leader," which is kind of the track I was on at the time. But there's a lot of good product leaders out there, probably better than I was.
And for me, the thing that felt really needed in the space was how do we make this career sustainable for people? So you're not a founder for a year or two and then you cash out and burn out, but if you want to work on your company for 10 years and hopefully you do, if it's successful, right? It's going to be around for longer than that. Yeah, how do you make that work that you can do for 10 years or 20 years and not go crazy?
Paul Davenport:
I love that. That's actually super interesting and a really good take because a lot of what we talk about at Boast too, is making sure that companies have access to non-dilutive funding so that they can hold onto their company for as long as they can. Everyone thinks, I feel like Shark Tank might've ruined all of us that we have to hand over equity, that you have to hand over a stake of your company as soon as it starts doing well, and that's simply not the case.
Now, I know what you're talking about is even bigger than that, and I'd actually love to dig in a little bit. I know why I said in the intro, you help startup leaders get unstuck and make their dreams happen. Could you speak a little bit about how you arm those founders with maybe the courage they need to stay on for the long haul and to really back their company beyond that idea phase and beyond that phase where they're actually passing MVP and they have a product in market?
Kenneth Berger:
Well, of course everyone's journey is very individual, so it's a little hard to generalize. But I think part of what I often see is just kind of a lowering of the stakes overall. Because I think so often when you're a founder, you put all of your ego into the company, right? And the company's success is your success and the company's failure is your failure.
And so while that's pretty natural, right? And certainly happens commonly, it's not too hard to see how that's a terrible way to feel good day-to-day, right? Because every little up and down is making you feel like your personal stock, your personal value as a human being is literally attached to that. And so really a lot of the work that we end up doing is saying, "Hey, actually your value is fundamental. Right? Even if your company crashes and burns, you're still a good person.
You're still going to have people that love you. Your intentions are still good." And so having just at least some decoupling of sort of your ego or your sense of value from the ups and downs of the company can be incredibly transformative.
Because all of a sudden you're like, "Well, we're going to try this strategy. If it doesn't work, we'll try something else." And so you can have more of this sense of ease and freedom around it because it doesn't feel like a failure is sort of a mark on you as a person. It's like, no, we're trying things. We're making guesses. None of us know what the future is going to bring. All we can do is make our best guess.
Paul Davenport:
That's a great point. Because I know from all the founders we've talked to on their show or from the events that we've gone to too, they're passionate and they take it very personally. It's of course, personal. You're putting everything into. It's your idea, but especially when sometimes they'll find out, for instance, "All right, your idea, it's not going to find a product market fit necessarily."
Doesn't mean you have to stop dreaming, but you may need to reevaluate what your initial hypothesis is going to be from the get go. How do you do that without taking it so to heart and without making it be like, "Oh, I failed at bat the first time." Not necessarily. There might just be a few tweaks you want to make there to get it to market, which I think is something that a lot of founders don't always think out the gate.
I think it takes a little bit of work and finding a partner like you who can really break down that wall and give them that perspective. I'd love to know. So in your experience as a coach, it's probably hard to pick favorites, but what are some exciting projects that you've worked on or founders or even just personality types that you've come across in your experiences?
Kenneth Berger:
One dichotomy that I see a lot in my work is often someone either sort of isn't standing enough for what they want. And so you think of people like people pleasers, right? Who are more aligned towards kind of keeping strong relationships than to asking for what they want or standing really strongly for what they believe in. Right? And so that's sort of one side of it.
And then the other side I tend to see is people who are on the other side of the spectrum that are very good at asking very loudly all the time what they want, but usually their relationships suffer, right? Because they're being so loud and so forceful so much of the time. They may be able to ask for what they want, but people aren't telling them yes. Because the way you get people to say yes to you is usually you're building a good relationship.
And so I think often the path of growth for these founders is kind of extending their range into that sort of other half. Because if you're only working at sort of one or two intensity level or you're only working at levels eight through 10 intensity level, right? You've got a huge opportunity. Okay, great. You're great at one end of the spectrum, but what about when you need to be more gentle or more reserved, or what about when you need to be more forceful? And so I think every founder can benefit from having a greater range to work in depending on what's needed.
Paul Davenport:
Yeah. I think that's a great, great point. And again, I have met founders at both of those ranges of the spectrum and it's tough, but I think that happy medium too, that's where I think you can weather those storms a lot easier too. You can tap into your intensity levels that you really want to ramp up at certain points, but that is really cool.
Now, obviously working with someone like you is a silver bullet for founders who maybe need to kind of find that happy medium that's going to give them the personal skills, but also just the mental awareness to stay on for the long haul. But are there any other kind of relationships that you would recommend founders seek out?
We talked to a lot of accelerators and a lot of incubators on this show. Is that a path that you think every founder should embark on? I know we also said that not every journey is the same, but could you speak to what that ecosystem would look like for an early stage founder in your ideal scenario?
Kenneth Berger:
I think that having a good set of advisors, whether that's from an accelerator or from investors or partners or even just people in your network, maybe friends or former colleagues, I think that can be really powerful and especially as a pairing with a coach. Because I'm not going to come in and say, "This is how you should run your business." Right? I don't know how you should run your business.
If I give advice to clients, it's going to be more around general best practices of, "This is how you process your feelings if you're going through something hard" or "This is how you give feedback in a way that's less likely to sort of activate someone else." But those things are pretty far removed from the more tactical details of how you run a business in a given sector.
And so I think the interplay of sort of an advisor and a coach can be great because you've got the advisor saying, "Oh, this worked for me. I had this strategy. This was really effective." But often, okay, someone gives you advice, but what do you do with it? Right? What's the right choice for you? And I think that to me is where coaching comes in to say, "All right, I got a bunch of advice.
I have ideas about what I could do, but how do I decide? How do I get past the fact that I don't know what's going to work, I don't know what the results are going to be? And so how do I make a decision I feel good about anyway?" And so that's not about knowing for sure kind of what the right path is. It's about making a choice that you can feel good about whether or not you get what you want.
Paul Davenport:
It comes back to something that I feel is a lot less material advice. It's a lot more just being like, "Have your head on straight about it and be very clear about what your goals are and stick to those guns, but don't lose those interpersonal just relationships," I think. I know that you did do a lot of product work at Slack. We talked about kind of your work in a Adobe before this as well too.
You've been at the big companies. But in your experience on the product team, I'd love to know just a little bit about what kind of R&D have you personally been involved in? A lot of our listeners and a lot of the customers we work with are involved firsthand in doing a lot of research and development, building those MVPs, just getting that product together and getting something that they know will have a market fit. What does that journey look like in your experience, whether in the big corporate world or even helping founders just figure out what they're going to work on?
Kenneth Berger:
So yeah, I've worked on all sorts of things. So I worked on a lot of kind of the core feature set for Slack, working on messaging, working on notifications. Some of my favorite sort of product lessons from Slack were actually the really little details about how we set defaults. Right? And Slack does some subtle things about defaults changing depending on the size of the team, right? Because if you're a very small team, right? And you're just trying to get people involved, maybe you want really aggressive notifications.
So everyone knows, right? To come into Slack and sort of read a message if they're not regularly engaged. But of course, I think people on very engaged Slack teams have had the opposite experience where it's like, "Oh my God, too many notifications." And so that it's those sorts of nuanced things of what's going to work for a given person in a given team in a given situation that are really interesting product problems to me.
Because it's something that sounds so simple, "Oh, how do we notify someone that a message has arrived?" But the right way to do that or the way to make that a best guess depending on the situation really has a lot of sort of nuance and specificity to it. So we ended up doing a lot of research early on trying to figure out what's our best guess and what's going to be right given the situation we're in.
Paul Davenport:
Yeah, research early on. And I think to your point too, there's going to be so many different kinds of users. I'm personally probably the person on our team who drives everybody else crazy because I'm up at 5:00 AM. I'm also on the East Coast. Everyone on our team for the most part is on the West Coast. And I'm like, "This is for later, please have your notifications on silent."
But I have 15 requests that I need because I'm chugging my coffee and I want to have this done by noon. So if you talk to me during all of that, I would've been a very skew in that direction for the, "Okay, I need the notifications, because I need it now." But bringing it back to product development too, talking to as many different customers who might be applicable to the solution that you're trying to bring to market, I think is very critical.
We've unfortunately worked with some founders who didn't do all of that due diligence at the start, and their product didn't get off the ground. They've pivoted, they've started new things, but to our earlier point too, they took it very personally when it didn't work out. But I think they could have gotten around that had they really done the research, had they really talked to those individuals who could be customers because they would've been customers if they had made the tweaks that they had requested or if they got the access to that information early.
So lots of great takeaways from everything you just said there. Now looking forward, what's your take on the current state of kind of the startup scene? I know that there's a lot of thoughts about funding. That's kind of what it always comes back to here at Boast, especially with VC markets, and then coming down to the balance of equity at different phases of the startup journey. But could you maybe talk a little bit about what you think the headwinds are in the market today and maybe just some advice for founders who are looking for strategies to stay afloat if not thrive, given the current conditions?
Kenneth Berger:
Sure. Yeah. I mean, yeah, I think I'm seeing a lot of the same things other people are seeing, right? That whether it's perception or reality or some combination, unless you're a hot AI startup, it seems like we're in a doldrums right now for the tech world and for funding specifically. But I went through college and the dot-com 1.0 bust. And so I was excited to get a job and then by the time I was out, there were no jobs anymore. Right?
The bust had happened. And so I've seen a couple of these ups and downs. And so to me it comes back to this sort of idea of fundamental safety. Right? Are we freaking out saying like, "Oh my gosh, this is terrible. This is going to be life ending for my career." Or are we sort of building some trust to say, "You know what? I don't know exactly what's going to happen with the economy or when things are going to turn around or what it's going to look like, but I'm going to trust that I can handle whatever comes and that it's going to be okay."
And so that's sort of one expression of that sort of fundamental sense of safety, of am I saying, "Oh, I'm only going to be okay if I get this outcome, if things are up into the right this day," or can I just trust that actually I can handle whatever comes, even though I don't know exactly what that is? So I think that that sort of grappling with reality of like, "Yeah, I don't know what's going to happen, but I'll be able to deal with it," can actually get us to be more creative.
And I think you saw a lot of that in the sort of 2008, 2009 bust of, gosh, we don't have all this money all of a sudden, but we've got new opportunities that we can take advantage of now. And I think when you stop being entitled to things being a certain way or having a certain amount of customer demand or a certain amount of dollars coming from VCs, then you can say, "All right, these constraints are fine. I can play within those constraints," versus feeling like, "Oh no, I deserve to have things be a different way and it's not going to work unless I get that."
Paul Davenport:
I love how you put that, being able to play within those constraints. I think that is a struggle for even the strong or low intensity. It can be difficult. And I also think another thing too, to build off of what you said is we really can't see the future. The AI of it all happened very, very quickly. I started at Boast less than a year ago. AI became part of our product feature set over the course of that time, but it was everywhere about two months after I started, whereas it was still firmly a nascent technology when we were going to events right at the start.
So I mean, next year, who knows what the next thing will be. I'm sure it'll still be AI in some capacity, but we're moving quick. So I mean, be ready. Don't get too invested into the one single state of being. I think being flexible and just to your point, and like you said, safeguarding your mentality and just making sure that you're not going to get overwhelmed by any changes because we don't know what's coming necessarily.
Kenneth Berger:
Indeed.
Paul Davenport:
Yeah. And Kenneth, before we sign off, was there any other parting words you'd like to leave for our audience in terms of just maybe advice about staying mentally fit or just sticking to your guns, given any challenges that they might be up against today?
Kenneth Berger:
I do think that getting better at asking for what you want is a skill that all of us can work on. I alluded to that earlier with the folks who ask too much and the folks who ask too little. And so it's worth looking at how you can expand your range there. Because I think there's all sorts of blind spots to look for. Right? One of the ones I love to watch for is people saying, "I'm fine." Right?
Because of course in the work world, usually we say, "Oh, I'm tired," or "I'm busy," or "I'm fine." And those are the only feelings available. And so when we actually unpack and check like, "Wait, am I fine? How do I really feel?" There's a ton of information there that can actually give you an idea of like, "Oh yeah, maybe I'm not so fine." And I'm like, "So what data am I getting from these feelings about how I might prefer things to be?
What's the vision for how my life could be different or how my company could be different or how my impact could be different?" And so pulling on those threads just a little bit can actually be really useful to start to articulate, "Oh gosh, I actually really want to make some change in the world." And it doesn't mean you'll get it, right? Or that it's easy, but it all starts with having that awareness. And to me, that starts with not just saying "I'm fine," but saying, "Yeah, I prefer things to be a little bit different" and starting to really think about what exactly that different is.
Paul Davenport:
That is fantastic, Kenneth. All right. Well, I can't thank you enough for joining the show. I'd love to know where can our listeners find you if they'd like to learn more?
Kenneth Berger:
Yeah, please check out my website. It's at Kberger.com K-B-E-R-G-E-R and yeah, I work with startup founders, CEOs, VPs, to help them along their journey to make the impact they want to make and feel good day to day. So I'd love a few folks would reach out.
Paul Davenport:
That is fantastic stuff. Well, I can't thank you enough Kenneth Berger for joining us on What The Tech? It's been a great chat. I hope to talk again soon.