At Uniting the Prairies 2025, Vendasta CEO Brendan King sat down with legendary venture capitalist and Techstars co-founder Brad Feld for a fireside chat that delivered real-world insight and strategic perspective.

From building effective boards and resilient companies to shaping startup communities and navigating the future of AI, this conversation dives deep into what it takes to grow something that lasts. Brad shares lessons from decades in venture capital—what works, what fails, and why giving first still matters.

Whether you’re building a company, serving on a board, or simply looking to lead with more impact, this is a conversation worth tuning into. Watch the full video or explore the full transcript below.

Full Conversation: Brad Feld & Brendan King 

Transcript: Startup Scale, Boards, Community, & AI

How Brad Feld and Brendan King First Connected

Brendan King: Well, I feel wholly inadequate up here with Brad on the line. Hey, Brad. How are you doing? You got a haircut.

So, you know, I've got some questions here. First of all, I want to thank the entire UP organizers and the committee, and Jonathan, it's been fantastic, you did such a good job. And it makes me proud to be part of the tech community in Saskatoon, and the Prairies, I should say, I shouldn't say Saskatoon.

So the first thing we're gonna do, Brad, is we're gonna talk about, how did we meet and how did we come together? And, you know, I'll kick it off in that, you know, obviously, I knew who you were long before you knew who I was. I'm a big sort of software as a service fanatic, and so I knew a lot about the Foundry Group and about Brad.

In 2021, we did fundraising. We raised some money, a hundred and nineteen million dollars, and we bought a company called MatchCraft, and we were starting to look for other companies, and one of the tools that we used was called Yesware.

I was talking to some other founders here. It's a sales enablement tool like Salesloft or Outreach. And we used that tool, and we thought this would be a great product to make, to accelerate our CRM and our platform. And so Eric Clark, who was working with us at the time, had reached out to Yesware, I think it was May. And, by July, I think we came to a to a deal, and by October, we had closed the deal.

And I know that working with Brad was unlike working with any other person I've negotiated with because, you know, he really is a fair person. You don't have to, you're not trying to swindle anyone when you're working with Brad. So, Brad, maybe I'd like to hear from you. How do you think about how we met? I'm a little nervous to ask you that.

Brad Feld: I think you described, you described the path pretty well. I was on the board of Yesware. We'd invested in them when they were just an idea. The two founders, Cashman and Matthew, and the company was the first to have this idea.

It's kind of a for sales enablement. It was a category, and the idea that they had was to essentially integrate some sales functionality into Gmail as Gmail was starting to become more popular. They built a business that got to a certain size, about a million dollars a month ARR, and then stalled.

And, you know, in that, I was also indirectly an investor in both Salesloft and Outreach because both of those companies had gone through Techstars. And, they came through Techstars later than Yesware, but I watched sort of each of them grow and really become very dominant in the enterprise, which was an area that Yesware never really found its footing. But it had a bunch of SMB customers, and it had a good customer base and a good business. It was just having a very difficult time figuring out how to expand that business.

And, you know, as we started to look for a potential partner and acquirer, we worked hard to get the company break even, so that it could live forever. But at that stage, it really didn't have the resources to accelerate growth again.

As we're looking for companies, I'd never heard of Vendasta. We ran into Vendasta, indirectly through however the connections were made. I got to meet Eric. I got to meet Brendan. I remember the first conversation I had with Brendan, which was really sort of in a time where there was interest in the business, but there wasn't clarity about whether or not there was a deal to be done.

I came out of that meeting feeling really interested, and just trying to get something done because I like Brendan. I was totally comfortable as a Yesware investor in taking stock in another company that was much larger, and they had the potential to really be a meaningful business versus just cash out of a company that was, you know, sort of nice but stalled.

And I really could see in that first conversation with Brendan how clear he had figured out how to address and attack the SMB market, which is something that so many venture-backed companies struggle with, especially in the MarTech universe, and that got me excited.

You know, the negotiation moved reasonably quickly, and, I appreciate the way you describe me. I would describe you the same. Like, you know, it's kind of a no bs thing. We talked about the issues. You know, Brendan had a board and investor group he had to deal with. And in the negotiation, he was dealing with the CEO of Yesware and essentially me, who was the principal negotiator on our side because we were the largest shareholder. And I think at that stage, I think the other board members sort of deferred to Matthew and me to try to get something done.

What Makes a Great Board of Directors

Brendan King: That's awesome. One of the things that, you alluded to the board, and I don't know if I've told you this, but I think it's probably the best thing that ever happened to me was to get someone like Brad Feld on the board.

Brad has these mental models. He'll listen carefully, but when he talks, you ought to listen because he has a way of describing the situation and understanding it. But then getting down and, like, something that I have struggled with sometimes, but to the things that really matter and putting it into a mental model. And so, you know, Brad, you've written a lot of books on boards, and I remember as you came on, you didn't make waves right away, but you you you found a way to sort of shape the board.

And you know, as a tech company or any kind of company that has a board, what do you want a board for? You want them to help you. You wanna get advice so that you don't make mistakes that other people have made already. You know, the one way to go fast is to just find out and fail and try again. A better way is to learn from somebody who's done it before. And so, Brad, maybe you could talk about that mental model that you use about how a board, I think it would be really valuable to everybody if you could if you could share that.

Brad Feld: Sure. So I've been on a zillion boards. I think the first board I ever joined was in 1994, shortly after I'd sold my first company to a public company.

And, I would say that if you think about a bell curve or a normal curve, you know, where one end is, you know, a slope that sort of goes up and then kind of big hump in the middle and then down at the other end, You have a small number of extraordinary boards. You have a small number of abysmal boards, and most boards are in the middle. They're mediocre.

One of the challenges, I think, in the world of startups is there's a lot of confusion amongst board members and amongst the leadership team and especially the CEO who's almost always on the board as to what the actual role of the board is in the context of the growth and development of the company.

And it's a board which is a thing, and then there's individual board members who are people. And I think one of the mistakes that gets made very early on is to anthropomorphize the board, to talk about the board as though it was a unified thing, because it’s not, it’s just a collection of people.

And each of those people has their own experiences, or each person has their own experiences and their own frame of reference, and frankly, their own pressure from whatever organization they're part of, or their own experiences and their own perspective based on whatever their experiences have been.

So, when I think about a board that's a highly effective, really capable board, it's a collection of people whose goal is, this is for a private company, their goal is as long as they support the CEO, their job is to help her be successful. That's it.

And, of course, there's some governance dynamics that a board is responsible for, in terms of governance dynamics around all shareholders, which interestingly a lot of venture backed board members get very confused about because they also think that they have a responsibility for their own fund and their own investment in the company, which is true. But in the context of being a board member, the best way they can be effective for their fund almost always is helping the company be successful.

So, Jeff Lawson, who is the founder of a company called Twilio that I imagine many of you know, told me something that I thought was a wonderful way to encapsulate all that. He said, look, Brad. I get to have two teams. I have a leadership team, and I select each person on the leadership team, and I can fire them, and my job is to really get that team working great. And if that team's working great, we will be a successful business.

But I have, like, this bonus team, which is my board. And the difference is that the board can fire me, but it's still a team. And it's my job to help get that team working really effectively. And if I need help, you know, in his case, he had a lead director at Twilio. I have a lead director, sometimes it's a chair, chairperson, but somebody I can rely on to help me work with the rest of the board members to get everybody functioning as a team.

Mediocre boards don't invest the energy in building that team and working collaboratively through conflict. It doesn't mean everybody has to agree with each other. In fact, you want people to disagree. You wanna have good, healthy discussions and disagreements. But the same way a functioning management team works, you wanna make a decision, then you wanna get everybody behind it, and you don't want people second-guessing each other, and you wanna give the CEO the support to go get it done.

Brendan King: Hundred percent. And, that's, something that, you know, you're a busy guy, and I think we were lucky when, I think you had said I wasn't gonna go on any more boards, and so we were super excited and happy to get you on our board. And I just didn't realize how much it could help. You know, whenever we need something, the Foundry Group, which is Brad's, firm, always has people that can help, and he's one of the board members who inspires other board members to realize how much they can actually help and pick up and do things. So I appreciate that, Brad.

Brad Feld’s Career Journey: From Startups to Venture Capital

Brendan King: When you think about how you got started, so this is, to your whole career, I don't mean to put you on the spot, but can you think back to some key moments that led to where you are today? Maybe, you know, you're out there, so I didn't creep on you, but you know, you've got SoftBank, you had the 2021 bad year, and some other things. What are some of the key moments along the way that really helped make you who you are today?

Brad Feld: Hey. You said 2021. That wasn't such a bad year.

Brendan King: No, that was 2001, sorry.

Brad Feld: Yeah, I'm old. Well, I'll pull out a moment from kind of each phase of my journey, and I'll just give quick anecdotes.

I started my first company in 1987. And about six months after we started the company, we were losing money. We had no money, and we'd raised no money, but we were losing money.

And my partner and I looked at each other and said, we're out of business if we don't actually start making some money every month. And we weren't losing enough money where we couldn't kinda, like, make it through the next month, but it was really painful. We had a couple of employees who weren't really doing much relative to what we were trying to accomplish. They weren't generating money. So we fired everybody, and we looked at each other and said, from this moment on, every month we have to make money.

That was very formidable for me to not have any money, to not have an investor, to not have any resources, and to be running a business and realize that every month, I had to bring in more money than went out the door. So that was very early. I was probably twenty or twenty one years old when that was, when that was happening.

I sold that company in 1993 to a public company, and that experience was hard. It was really hard to decide to sell the company. On Monday, Wednesday, and Friday, I wanted to sell the company. On Tuesday, Thursday, and Saturday, I didn't wanna sell the company. And on Sunday, I rested, and I did that for about six months. 

And at some point, my business partner said to me, come on, Brad. Just make a decision. You know what? I'll give you a dollar. If you give me a dollar, I'll give you all my shares if you'll just make a decision. So I pulled a dollar out of my pocket and offered it to me and didn't take it. But, it was very hard to decide, which was a useful experience for me also because when I look back on it, I am so glad I made that decision.

We had a good business. We were making plenty of money every year, but I was bored with the trajectory I was on. And the guys that bought my company, it was a public company, I became the CTO of it. I got involved in doing deals. I didn't know anything about buying or selling a company or making investments. And this is in 1994, at the very beginning of the rise of the commercial Internet.

And so I took almost all the money that I made from that deal, and I invested in forty companies over three years as an angel investor. And, I was also involved in about fifteen acquisitions as the tech guy on the DLT. My job was to show up at the company we were buying. And when I left, the founders, who every one of them thought they had something really special and magical that they should get paid an outrageous amount of money for, the goal was for them to say to each other, you know what? We can't bullshit these guys about what we got. We gotta play it straight. Because that guy figured out what was going on.

So, I kinda learned through that process from two guys, Len Fassler and Jerry Pock, how to do deals, and I ended up doing a number of companies with Len. He passed a few years ago, but it was an incredibly close, personal experience with him. And from that, I really learned what I would describe as the way I've approached treating people in business, which is that I actually don't really have the need to win.

I like to be successful, but I don't have to win, and I separate the two concepts. I view everything I do as a collaboration, even if it's a real negotiation on two sides of the table. I look at everything as a multi-term game, and what I mean by that is I'm gonna be dealing with the same person that I'm an adversary for again and again in the future, and I want to have credibility, reputation, and relationship as long as they do. And I've definitely had plenty of experience with the people who don't share that frame of reference, and so you don't have relationships with them going forward.

But I really learned from Len the power of investing the emotional energy and building those relationships, even when you're in an adversarial situation, or even when you're in negotiation. That was very powerful.

I had a lot of success in the rise of the Internet. I started a couple of companies, including one that went public, and its peak market cap was worth over three billion dollars, which today actually isn't that much, but then was an enormous amount of money for a tech company. And, when the Internet bubble burst, two years later, that company went bankrupt.

And I learned a lot in that experience, both on the ride up and the ride down, about fundamentally building a durable business. That company's name was Interliant. The business was an ASP and web hosting business back when that was a thing, but you kinda pre-cloud computing. But the fundamental economics of the business didn't work.

We were great at one thing. We were great at losing five million dollars a month. We were great at it. And when the market turned and capital wasn't freely available, and if people remember the Internet bubble, like, part of the thing that fueled the growth of the Internet bubble was just this enormous amount of capital that was available as long as you had a heartbeat.

On the other side of that, when the capital wasn't available, we couldn't get from five million dollars a month losing money to being profitable. We just couldn't. And, eventually, before we went bankrupt after selling a bunch of pieces of business and changing and firing people and layoffs, we eventually actually did get to a place where we were profitable, but we had debt on the business that we couldn't service because one of our financings was a large debt financing, a hundred and fifty million dollar debt financing. And we just couldn't make the debt payment, so we really had, we didn't own the business anymore. Debt holders did.

It happened to a lot of telecom-related companies during that period of time and a lot of Internet companies, so we were one of many. But it was really, really significant because I spent many years working hard, very hard on that business to basically have it fail.

I went through the bankruptcy, and I thought I was done. And then I got sued for fraud for a hundred and fifty million dollars personally, which was way more money than I had. And, it's kind of interesting to get sued for such an extraordinary amount of money for fraud when in at least in the US, then, I don't know if it'll be true forever in the US given all the changing political tides. But then it was legal to fail. Like, we just failed. The business was bad. We didn't do anything illegal.

But having to navigate through three years of that after failing got me to a place where the ability to deal with hard stuff in your face, it's just kind of, like, part of it. And I think that was another foundational thing. I'll tell one more story, and then I'll finish. But, like, being comfortable with really hard stuff that's really disappointing, that's not working, and just dealing with it directly and doing it in a way that's as you know, it's graceful., it's it's not positive, but it's forward-looking.

And instead of avoiding dealing with reality, just dealing with reality, instead of being avoidant, and I use passively avoidant or avoiding things, just either deciding you're gonna do something and work on it, or deciding you're not. And if you're gonna work on it, then just go after it.

Why Place Matters: Topophilia and Building in Smaller Communities

Brad Feld: I'll end on a positive note. Our positive story was really transformative to me. My wife and I moved to Boulder, Colorado in 1995 from Boston. She's from Alaska, and I'm from Texas. And we both went to school in Boston. Northeast was good for us, but it was not home. We randomly moved to Boulder, Colorado because Amy told me one day that she was moving to Boulder, and if I wanted to, I could come with her. And we happened to be married, so, I said, sure. Okay.

So that's how we ended up in Boulder. It was pretty random. Fell in love with the place. And, one of our senators in Colorado, John Hickenlooper, who was governor for eight years, long-time friend, introduced me to a word that I think all of, many of you all probably understand, which is a word called topophilia.

And I can't see the audience, but raise your hand if you've ever heard that word before. Brendan, tell me if anybody raises their hands.

Brendan King: Yeah. I'll tell you. Nope. No hands.

Brad Feld: No hands. Alright. I'm teaching a new word tonight. You didn't realize it was a vocabulary session. And by the way, there's no tariff on this learning.

The word topophilia means love of place. I was in love with Colorado. I fell in love with Boulder. I imagine many of you love the plains. You love your place. I have my little tag on. I pretend like I'm actually there with you. United the Prairies. I expect many people in this room have topophilia. Now raise your hand if you have topophilia. Any hands go up?

Brendan King: Oh, yeah.

Brad Feld: Oh, yeah. Okay. Got a new word. But this was the experience for me. In 2010, the global financial crisis was still going on. Right? Remember in 2007, 2008, the world was gonna end. In 2009, the world was really gonna end. Money wasn't gonna actually be money anymore. You know, it was one of the waves of the crypto people saying, see, I told you money isn't worth anything.

And then, you know, things kind of eventually started to stabilize, but it was still a really, really rough financial time for everything. By 2010, it was starting to be less bleak, and this sort of notion of innovation and entrepreneurship as a way forward was starting to be discussed.

And there was an article, in, one of the sort of intellectual, political magazines that talked about entrepreneurship and innovation as important, and it listed four places in the United States that were leaders to look at.

Silicon Valley, which, of course, is not a city. It's a bunch of cities. New York, also five cities, Boston, which does actually happen to be a city, and Boulder. I remember reading that article and thinking to myself, one of these things is not like the other. Boulder's a hundred thousand people.

I thought, you know, why is Boulder in this article? And what that did was it allowed me to sort of reconfigure my thinking where I started to say, look. Any city with at least, and I said for many years, fifty thousand people, can have a vibrant startup community. That phrase didn't exist at the time, and by the time I came out with the book, Startup Communities in 2012, I really had sort of settled into this notion that it was critically important to society to get entrepreneurship happening everywhere in the world.

That the idea that creating companies, not just tech companies, but companies of any sort, that the energy of innovation and entrepreneurship was a critical part of any city's long-term health and development. Not the only thing, but it was just a component. And, you know, from then over the last fifteen years, obviously, I've done many things that have amplified that, but but there's some critical moments for me.

Maybe another critical moment was when I first talked to Brendan and ended up on the Vendasta board.

Brendan King: I hope so. You know, I'm thinking about Boulder being a smaller community. I love Boulder, by the way. It's awesome. The Prairies are kinda like that. So you know, I remember when I first went into tech, I had a computer company, which I sold in ninety nine and went to a company called Point two, which was building software. And at the time in Saskatoon, you know, which was three hundred thousand people, software was something that got built somewhere else, San Francisco.

The Birth of Techstars and the Power of Inclusive Communities

Brendan King: And, you know, you've written this book, and we're gonna talk about your new book too, but you've written this book, on communities, and, I imagine that happened when you were founding Techstars. I'd like to understand what the advantages are of smaller communities. I think I can name a few myself, but I'd like to hear your point of view on, what are the advantages of smaller ecosystems and, you know, what do we need to do or what are we missing or, you know, what do you know about it? And why did you start Techstars in Boulder?

Brad Feld: Well, I'll answer the question in reverse order a little bit. We started Techstars in 2006. The way Techstars came together was David Cohen, who's the CEO of Techstars, had this idea. I didn't know David. He didn't know me. He had a longtime business partner, a guy named David Brown. They had sold their company to another company. Cohen had left. Brown was still at that other company.

And, Cohen had come up with this idea. He had started Angel Invest, making some Angel investments. He's very unsatisfied. He's like, I don't wanna do one Angel investment at a time. I wanna do ten. And I don't wanna, like, you know, put some money in and then never hear from the founders again. I wanna, like, be involved with them every day and help them get their thing going. And he had this idea.

The idea of an accelerator didn't really exist. I think, YC had run one program, and so there was a little bit of, like, noise around what that kind of an idea was that they had had, but there was nothing else. There's no, like, accelerator construct.

I was at the time, doing a thing I called random days. I did this for about a decade, where I'd meet with anybody who wanted to meet with me for fifteen minutes. So I'd gotten to the point where I was well-known enough that I literally couldn't do coffee meetings. I didn't want to. I couldn't go out to lunch or dinner. It's just too much, with all of the inbound that I had for people that wanted to get together with me. But I wanted to be accessible more than just on the other end of email.

So once a month, I do fifteen minute meetings. I usually did about fifteen of them. Sometimes maybe I do twenty of them in a day. And, I put an online calendar up, and it was first come, first served. People just signed up for spots.

And you'd sit down with me, and I had a timer running, and I'd say, alright. The next fifteen minutes belongs to you. Let's go. And, eventually, I figured out that my goal was to learn one thing out of each meeting and try to help the people with one thing and one connection from each meeting so that I didn't feel like I spent a day doing something that, you know, had no value.

But I did that for a long time. I don't know. I had several hundred meetings like that. David was one of them. Took him three months to get on my calendar. He sat down. He slid like a a brochure, a color printed out thing. This is before everybody had a color printer in their bedroom. You know, they probably went to the copy local copy shop to get printed out. That sort of described what Techstars is.

And, he was very nervous, and, he started talking. And I don't do a good job if you're I'm trying to read and listen at the same time. I can do one or the other, but I have trouble with both. So I said to him, let me read this. You put some energy into it. Just give me a second to read it. I read it, and I was super interesting.

I said, look. What do you want? He said, look. I'm putting some he described. I'm putting some money into this. My partner, David Brown, is. We wanna raise a little bit more money. How much? He told me. I, I said, I'll tell you what. I'll do fifty thousand. He was doing eighty thousand. David Brown was doing fifty thousand.

I said, look. I'll do fifty thousand, and hang on one second. And I walked out of the room, and I called a guy named Jared Polis, who's now governor of Colorado, but he was a close friend who was successful entrepreneur. And I said to Jared, hey, Jared. I'm gonna put fifty thousand dollars into this new thing called Techstars. Are you interested? And he says, yeah. I'm in. What is it?

And I told him really quickly, and he says, great. And I went back in the room. I said, alright. Jared's gonna put fifty thousand dollars in. And David said, who's Jared? And that's how we got started. And, you know, I'll tie it to Give First in a sec because it's such a good example of that kind of a story. Like, there wasn't months of diligence and things like that. It was like, this is an interesting idea. I like this person. I have a good first impression. And I said to him, look. My the only check I wanna do is to make sure you're not a crook or a flake. And I can do that with a half dozen emails. So that's how it started.

That was really what it was, was we just sort of looked at each other and said, let's for the summer, let's fund ten companies as angel investors with this money that we just put together. Again, it was, two hundred and thirty thousand dollars. Let's give them each twenty thousand bucks, so I'll have ten thousand dollars to run the program. Sorry, Thirty thousand dollars to run the program. Not to pay David or anything like that, but to buy, like, you know, Mexican food for lunch and, you know, maybe have an event here or there. And we rented some really awful space in the basement of a building, that we called the bunker.

And what I then did was I rallied about fifty friends, many who were in Boulder, some in the Bay Area, some in New York, to be mentors. And at the time, the word mentor didn't really exist. And so what we did was, we basically just said to people, look. Just we don't know. Just come spend some time with these companies. We don't know what it's gonna turn into.

So that's 2006. By 2010, Techstars had expanded to a number of other cities. We were in Boston, and we were in New York. We felt like we'd sort of figured out how to run this mentor driven accelerator, and I was starting to get my mind around this idea that the not just the concept of an accelerator, but this concept of a start-up community could really make a difference. That led to 2012.

Now to the second part of the question, when I wrote the book. Second part of the question, how can a smaller city, you know, a couple hundred thousand people really engage? What are the what are the key things?

I'll go back to what was said at the beginning. The principles, the boulder thesis, which really are the four bullet points associated with the idea of how to build a successful startup community is one, the leaders have to be founders. They have to be entrepreneurs.

Two, you have to take a long term view, and I like to say at least twenty years.

Three, you have to be inclusive of anyone who wants to engage no matter what their experience level, no matter where they're from, no matter what they've done, no matter, you know, obviously, what they look like, you know, what their backgrounds are. Just anybody who wants to engage should be welcome and part of it. And you have to do stuff all the time. Like, events like this are super helpful, but you gotta do stuff all the time. And I remember in Boulder, at the point at which there were so many events each week that I couldn't go to them all, when there were multiple things happening on the same night, I knew that we had crossed over into another category.

You know, if you think about a place like the Bay Area, anybody that spent any amount of time in Silicon Valley, and any given night, there's ten, fifteen, twenty things to do if you're a founder looking for founder stuff to do. And I'm not saying that you have to have ten, twenty things to do, but you have to have two or three. Like, that sort of thing, that momentum, that energy has to be continual.

Next, there are always going to be power dynamics in a smaller community that are easier to understand and see than in a big community. In a big community, you can hide. Right? You can have lots of factions, or you can have you know, in New York, you can have the Brooklyn people are different than the Midtown people, that are different than the Queen's people, that are different than the Long Island people. And, like, the real magic is when they all get together, the Brooklyn people go to Long Island, that's when real magic happens. But you kinda hide in your own little part of this big place.

In a smaller town, it's hard to do. You can't really hide. And so what has to happen is the people who have more power have to be more gracious. They have to be more inclusive. They have to be more willing to give and put energy into the system. They have to be inputs, not extraction.

And it's not that it's philanthropy. It's not that it's charity. You do expect to get something back, and this is now the definition of Give First. You're willing to put energy into a system without knowing what you're gonna get back. Again, it's not charity.

You do expect to get something back, but you don't know when, from whom, in what consideration, in what magnitude, and over what time frame.

And when I look at my experience from when we moved to Boulder in 1995 to today, it's kinda crazy to me that it's been thirty years, which just helps me realize that I'm getting old. The amount that I've gotten back from that behavior is a hundred times what I put into it. Thousand times. And some of it's financial, and some of it's reputational, and some of it's just raw, pure satisfaction, and some of it's emotional. Some of it can't even be measured, and some of it's watching other people have their success that indirectly came from something that I did or helped do at some other point in time, even without them saying thank you for whatever.

So I think in a smaller town and, you know, half a million people or less, the key thing is to not hide. And when you're in a position of power to actually try to support others rather than exert your power and control, then, of course there's times when you're in a powerful position where you will do that. But if you can put a lot of your you know, where you will exert your power. But if you're in a position where you can support others, elevate others, put energy into things without defining transactionally what's gonna happen, how you're gonna benefit.

And then I'll use today as an example. It would it would have been relatively easy for me to continue to try to dominate the Boulder startup community, to be the king of Boulder. And in fact, there is a period of time where anybody that did anything in Boulder and they interacted with somebody outside Boulder, people would always say, do you know Brad Feld? Is Brad gonna invest in your company? Is Brad involved in your company?

That's not helpful to the startup community because I can't I'm not gonna do everything, and I can't be involved in everything. So, like, figuring out narratives around that so it doesn't look like I'm the control point. Fortunately, there were multiple leaders, so I wasn't the only one.

But then as time passed, as I got older, I really focused on elevating the next generation of leaders, and I'll give today a current example of that. Next week is Boulder startup week, which has been going on since 2008, I think. It's the oldest startup week in the world. It's completely volunteer-driven.

I was very involved for the first handful of years, and for many years, I would come to a couple of events. And for the last couple of years, I haven't meaningful way. Maybe I'd done an event here or there, but I've kinda just stepped back to let it have its space.

And, we're going back to Boulder on Friday. We spend the winters now in Tucson. And I'm gonna give a couple of events, including the kickoff breakfast. And it's fascinating to see the next generation of leaders leading that kind of a thing and, you know, sort of embracing the old guy coming into the room as their supporter because a lot of the people who are the leaders today are people I've been helping and supporting in the background rather than in the foreground. So hopefully, that's some tangible stuff for y'all.

Last comment on this. There will always be negative activity in a startup community. There will always be disappointments. There will always be bad actors. There will always be problems. I have kind of a mental model of I give everybody one second chance when they do something that screws me over.

But after that, I don't bother. But I don't try to torture them. I just give them one second chance. And if, I decide to move on from a relationship, I just don't engage anymore versus I try to burn them to the ground or burn their house down or exclude them from everything.

So, like, thinking about the cultural norms that y'all have in your community so that most of the activity is aimed at positive. And when something negative happens, it's something that doesn't create poison across the system. It's just a short-term blip that you move on from.

Introducing “Give First” and the Mentor Manifesto

Brendan King: Yeah. That's awesome, Brad. You know, maybe that could lead into I just wanna give you a little, props on your, you have a new book, it's called Give First, the Power of Mentorship.

I think, inspired by what you just said, you know, we have these, tech events at the Vendasta called Ideas on Tap, and I think we'll buy a bunch of copies of your book and maybe get you to sign them and give them away next time at the, the event to get some folks to come. But maybe just, if you wanna give a pitch for your book right now, do you, do you wanna talk, maybe you've already done that in what you just talked about, but anything you wanna add?

Brad Feld: Well, I'll just add a couple of things. But first, thank you. Like, my goal with writing books, you know, is, the comment about venture deals earlier was, was really nice. Like, I've written this is my ninth book. I love to write. It's the way I work out my ideas. It's why I blogged for so long. You know, I'm a reader and a writer, and that helps me think.

For this book, I put a lot of energy into trying to consolidate my own personal experiences, into my own personal philosophy, in a very consumable way. And so the book really has, four parts to it.

The first is a section on Give First, talking about Give First and the origin and defining it and talking about, like, what it means.

The second part is about the Techstars mentor manifesto and how to be an effective mentor. Techstars mentor manifesto, if you don't know, it has eighteen points. We've learned an enormous amount about how to be mentors and how to be effective mentors for startups through the experience at Techstars.

And, I have a section on each of the eighteen points. And in each of those, I broke it into three categories. I write an essay at the beginning. And when I say essay, I don't mean like a boring as shit essay, but a fun, punchy description of the thing.

I then use a story, and many of the stories are autobiographical. So there's a lot of memoir and a lot of my own story in it, but not entirely. I've got others, and I also have some things that are just playful to try to challenge the reader at the time or change the pace. And they end sort of tying it all together for that particular item in the mentor manifesto. So there's this big chunky thing. If you're interested in being a mentor or you're a founder who has mentors, like, this is a way to be effective in that context.

And then I have a section about the challenges of Give First because these are some real downsides to it and how I've learned to modulate how I interact with people so that I don't burn out.

And for those of you that know me, I've been very public about a couple of mental health episodes where I got very depressed. I've written about it in public. I'm not shy about talking about the stress, of being a founder and a leader and the challenges that we have, especially dealing with lots of complicated stuff in our lives that might or might not have anything to do with the work we do.

There is definitely a toll that this philosophy has on one, when you make yourself really accessible, especially as you become more successful.

And then the last section, is a section on something I call entrepreneurial tzedakah. And I like to coin phrases, and I hope when this dust settles on this book, this phrase makes it into the lexicon.

There's a philosopher from the tenth century, Maimonides. And Maimonides is famous for this notion of tzedakah. For those of you that like Neil Tzedakah, it's not his songs. And, tzedakah is a Hebrew word that loosely means, giving or charity. Doesn't really mean that, but that's kind of a loose translation.

He has eight levels of sudaka. And the first level, when I read it, I said that's angel investing. I actually was sitting with Amy, and I said it out loud. And I said the first level of tzedakah is angel investing, and she basically said some version of what the hell is tzedakah.

And what it said was the highest level of giving is to give to somebody in advance of their need, without defining what you're gonna get back. And I've been talking about angel investing for a long time as for-profit philanthropy.

And what I meant by that was that if the company fails, you get a tax deduction for the failure, but you still helped somebody learn and grow and develop, and you potentially helped a bunch of people in a bunch of different ways.

If it's successful, you make a multiple of your money, sometimes ten times, a hundred times, a thousand times your money. Like, that's such a good thing. So I I kind of, in the end of the book, try to tie it together with the philosophy of way of being.

It's a short book. It's only a hundred and fifty pages, which really with if you take the filler out, it's about a hundred, hundred and ten, hundred and twenty pages. I think the world has too many two hundred and twenty five page books. So I tried to make it easily consumable. I put a lot of myself in it. If you've read any of my stuff, you know that my writing is pretty casual.

I like to think I'm a reasonably good writer now after everything I've done. And I really tried to link it to anyone who's a founder, anyone who's an investor, anyone who's involved in startups and startup communities, anyone who's a leader.

And it's not prescriptive. It's not do this, do that. It's if you get a couple of good ideas from it, then it was a successful experience.

Brendan King: Yeah. You did such a good job of selling it. I won't be able to give any away because everyone's gonna go buy it.

Brad Feld: Look. You can give them away. No. No. People, please buy them. You know, I'm a good book salesman. Please buy my book, and then Brendan will give you one with me signing it when you come to one of his events. And then you can give away the one that you have that's not signed, you can give it away to somebody else.

Brad’s Take on AI, Tech Cycles, and Building Useful Products

Brendan King: That's fantastic. Hey, you know, that's great. So you can understand why we're so fortunate to have Brad on our board with the mental models and the clarity that he brings in any discussion he has. What I did wanna close-up with something about, you know, turns out, I'm actually, I think Brad's eight months older than me. So not a lot older. But we both saw, like, the dot-com crash and, you know, the housing crisis in 2008, our financial crisis.

And then we, you know, we went through, COVID and the zero interest rates and all these things. And I I you know, grow at all costs. Brad, what are you seeing now? And I I can't get out of here without saying, hey. How important is AI? Because if anyone who knows me knows I'm totally obsessed.

How have these last five years shaped your outlook? And what are you seeing that you could share with the folks here that they should think about, and how they might take advantage of what's happening to us right now?

Brad Feld: Sure. I got interested in computers when I was about thirteen. I got an Apple two computer for my bar mitzvah. And so, you know, that would have been 1978. Right? You know, very early. Apple didn't even have, I don't think they had two floppy disk drives for the computer yet, I think he only could get one. It was forty eight forty eight k of memory. They didn't have the integer card yet for the people in the crowd that's really old.

So I've been fascinated with computers and technology since then. My uncle, who I talk about in Give First, Charlie Feld, was, essentially the inventor of the handheld, a handheld device. He worked at Frito Lay as the head of data processing, which is what you would call a CEO back in that time frame period. And they came out with a handheld device that allowed the truck drivers, to basically be route salesmen and route inventory people for their Frito Lay potato chips. And that was really the first meaningfully used handheld device computing device of any sort.

So, as I've watched these long arc of, technology and technology innovation through my lifetime, It's very easy for me to believe that it's going to continue to be a an extraordinary change to the fabric and the way that we live as a species on this planet. So there's no slowing down or changing or inhibiting, innovation.

It's also a truth that the tech industry lurches from wave to wave of new thing. And for anybody that's aware of the Gartner hype cycle or understands the dynamics of capital flows and hype cycles, you have these experiences that are not necessarily bubbles. That's a finance term, but where the hype of something gets far ahead of the economic utility of something.

And then it comes back down some, and then eventually over time, the curve continues to grow and value continues to create.

And there's enough history now to see some of the companies that have really been good at the marketing side of those curves, independent of how successful they've been on the individual technology pieces of those curves, where the ultimate endpoint is that the technology pieces of those curves become real.

Microsoft would be kind of the canonical example of that, and all you have to really do to think about an example that's not AI here is to go back to cloud computing.

If you think about the evolution of cloud computing, cloud computing is really no different than what used to be called mainframe computing, which then evolved into desktop computing, which then got connected via the Internet, another wave, where then people went from having client server computing where you had servers that you controlled on your premises to services in a, servers in a data center somewhere. That was the company I created, InterAlliant, web hosting, application service providers.

The company that sort of then started the next wave of that was this little tiny thing called Salesforce that coined this phrase software as a service. And then, eventually, Microsoft coined the term cloud. And by the time Microsoft really coined the word cloud, AWS was already a really big thing.

And today, of course, cloud is the thing to label what Google, Amazon, Apple, Microsoft, and many others get a huge amount of their revenue from in terms of that activity. So that's just an example. Like, put that against any wave you want in technology.

And we're in the middle of a new one of those, which, of course, is AI. And there are a lot of amazingly fascinating things that are happening with AI. It is still very unclear which things are going to have the real long-term impact versus which things aren't.

There have been ten zillion companies funded, where many of them are all doing the same thing where you know that nine out of ten, or ninety nine out of a hundred of those are gonna fail.

I'm actually really psyched about what Brendan and Vendasta are doing with AI and the way that Brendan's embraced it because he did something right from the beginning, and I think it was because of obsession about the technology, obsession about the product, and a recognition of the constraints that you have as a big pretty big company now with lots of other stuff you've gotta do versus a raw startup with, you know, some money and no constraints, is that you had to look at it from a customer perspective.

I remember the first time you showed me what, you know, effectively was the equivalent of an AI employee in your existing chat functionality, where, you know, I could not just interact with it, but I could also call the eight hundred number and interact with that using voice.

And you weren't creating the next layer down of the technology. You were building an application layer on top of the underlying infrastructure that was AI that did something that was really productive for your customers.

And I think we're in the phase now in, you know, middle of 2025 where we're starting to see those things stick. And so we're past the novelty of interacting with, a chatbot. We recognize, you know, we recognize the depth of being able to interact with whether it's Gemini or ChatGPT or Claude.

I've started programming again as a hobby. I used to write software. I stopped writing software professionally in 1992. For those of you that are interested in a video game, if you remember the Asteroids video game, I wrote a video game called Dynastroids. Dynastroids dot com. It's got a leaderboard. Feel free to try to top the leaderboard. Of course, the guy at the leaderboard found a security problem in the software, so he was able to hack it. So he had, unlimited immunity, so that the ship never blew up.

But it's been fascinating to use Cursor. And, you know, I I didn't know how to write code in JavaScript, and I had never deployed something, you know, on Vercel. And, I could have spent a lot of time on that learning curve, and it was just awesome to be able to go up the learning curve with the assistance of this technology. So those applications are starting to be real, and we also have a pretty good understanding now of the limitations of LLMs.

And you know, we're sort of at this moment where I think over the next twelve months, you're gonna have this bifurcate I think you'll have a bifurcation between three things, real efficacy of companies like Vendasta building integrating AI technology into their products in a way that really makes their products special and magical and take advantage of this new technology layer.

You're gonna see the mega funded infrastructure players either hit a wall or be able to navigate new parts to the innovation cycle so they're not all doing the same thing. And I'll give you an example. I see that we're times up. I see the thumbs up means times up, Brad. Here's an example of something in the stupid category that AI can do for you today.

And if anybody uses Microsoft Copilot, I encourage you to go do this. Come up with ten bullet points, put it into Copilot, and say, make me a PowerPoint presentation from these ten bullet points. And then take the PowerPoint presentation and tell Copilot, make me ten bullet points from this PowerPoint presentation.

And just think about how useless the activity is that just happened. And there's a lot of that going on in the world of what people are doing with AI. I just use that as an absurd example, but I could give you hundreds of them if somebody wasn't showing me off stage. So I think the big mega funded companies are gonna have to sort out what is useful and what's not.

Then there's a third layer, which is that there's gonna be a ton of things that got funded and had hype that are just gonna go away because they turned out not to be that useful for anyone. I don't think any of that's discouraging. I think that's the natural part of the wave of the cycle that we're in.

And as a founder, if if I had to give advice to the founders in the audience, I'd say focus on doing the same thing that since the beginning of time founders have focused on in the context of the software industry, which is think about things from the perspective of your potential user and build things that are useful for that user.

And make sure you understand what you're doing for that user. Get stuff out early and iterate rapidly on it. Make a lot of mistakes as you're learning what's actually useful.

If you're an investor in the crowd, my advice is good luck.

Brendan King: Well, thank you, Brad, so much for your time. I think we're about ten minutes over, but. Oh, we're gonna take a couple of questions. That's fine. And, you know, I never I didn't see anyone not paying attention, so I think you've, as always, have everyone in rapt attention. So let's get a couple questions from the audience.

Grayson's got the mic. Here we go.

Audience Q&A: Supporting Innovators and Startup Ecosystems

Guest: Hi. Thank you for that. Can you hear me okay?

Brendan King: Yeah. We can hear you great.

Guest: Thank you. All great insights. I'm curious on your perspective. You know, we hear stories of the next innovation is being ideated right now, but we don't know about it. So we're talking about AI, but there's probably something coming up next that we're going to see be the next hype thing in about ten years.

How can startup communities support those people? Because they might be, you know, as ideators or creatives, kind of in their own world and not aware of communities like this that could help foster and accelerate that idea coming to life?

Brad Feld: Fun question. And I would tell you, it's not the next thing's gonna next hype cycle is gonna start in ten years. The next hype cycle is gonna start in twelve months. I mean, it is amazing to me how compressed and accelerated all this stuff is and how they overlap. So it's not this linear thing, but it's this thing where stuff is constantly changing.

And if you think about tech, for example, just as a broad industry, AI is this thing that dominates, but it's the amount of energy going into the category, for example, called defense tech is absurd. The amount of energy going into space is crazy, and these are things that five years ago nobody even talked about.

And so I think the opportunity is just in whatever dimension of innovation you want. I live in Boulder where there's a lot of life sciences stuff. The intersection of biology and technology, especially with, all of the action over the last ten or fifteen years with genomic sequencing and software intersecting with the actual biological sciences and now applying large learning models to that kind of innovation and what that could mean in terms of drug discovery and drug creation or fundamental understanding of human disease states. Like, there's so many dimensions of this, and my advice for a startup community comes back to this notion of being inclusive.

Like, know what's going on at your local university. Don't let it be a parallel universe. Don't let the university try to co-opt innovation and entrepreneurship and keep it separate from what's going on in the community.

Don't let technology transfer be a barrier between professors, graduate students, students, people in the community that have expertise in the area, people that don't have expertise in the industry or in the area but are just interested. Like, just get all that stuff touching together, and it's an advantage. This is an advantage in a three hundred thousand person town that doesn't exist in a multimillion person town. Because, again, you can kinda get to know all the pieces. You can cover all the landscape, but you have to go to it rather than hoping it comes to you. And I think if there's a message, it's that. It's go to it. Go to the things.

Go to things that are different than what your normal places are. Go in groups if you don't like to be alone or in a new thing. But engage, crossover, don't kinda wait. That's the magic.

Brendan King: Awesome. Do we have another question? Must be one. You answered all them.

Brad Feld: Do I get props for wearing your shirt?

Brendan King: Oh, I can't see you. Everybody's looking straight past me. It's a little weird, but, yeah, you get props.

Alright. Well, thank you so much for your time. You know what? In real life, Brad is Oh, there is a question back here. I'm just gonna tell you how much how fun Brad is in real life. You could talk to him forever. One last question.

Guest: Hey, Brad. Thanks for taking the time. I've, read your book so many times. It's become a personal bible. I am very curious on your perspective as someone that moves moved to Colorado, to Boulder. What keeps the best founders there and to keep building from Boulder?

Brad Feld: So I'll I'll come back to topophilia. If you fall in love with the place you're at, you won't wanna leave. And when you have success, you will want to reinvest energy into that place.

And one of the things that's fascinating to me about 2025 versus going back to when I lived in Boston in the 1990s, I even traveled a lot then. I mean, I had a bunch of clients in California, so I was constantly on red eyes going across the country.

When I was investing, and I lived in Boston, I invested across the country because I had a network in Seattle. My first company was a big Microsoft partner. I had lots of, you know, Northern and Southern California. Los Angeles, I had a big network. Texas, I grew up there, so I knew a lot of people in Dallas and Austin. A couple of other random places for different reasons, Kansas City happened to be one of them. And so I traveled all the time.

And as I developed, you know, first at Mobius SoftBank and Mobius and the investing work I did there and then at Foundry and then with Techstars, continued to travel all the time. And until COVID, I traveled probably seventy-five percent of the time.

And, today, after COVID, I decided I was no longer gonna travel for work. So this is not a special moment where I'm doing this remotely. I do a lot of this remotely, which twenty years ago you couldn't have done. Like, it wouldn't have been a thing.

So I think the biggest dynamic that causes people to stay where they are today, I mean, people left before a place for opportunity because they didn't feel like they could get it where they were.

Now time and space is different because of remote, because of this technology, because of how organizations are built. It doesn't mean you don't have to get on a plane and go someplace. It doesn't mean that you don't have to go somewhere to build a business, but it means that you can choose where you wanna live and then build your life around that. That was kind of a truism for Amy and I when we finally decided Boulder was it.

And I think for a startup community, the key thing is, again, if you're inclusive of everybody and when you become successful, you stay part of it. You stay humble.

You don't try to control what's going on.

The community wants you to stay. They want you to be part of it. They want you to help. Like, there's this positive feedback loop that really builds up.

The thing that causes, I think, people to leave, especially after they've been successful, more often is that for some reason, something happened where they lost the topophilia. They lost the love of the place they were at and lots of different reasons for different people, and some of them could have nothing to do with business and startup community. It could be personal life or where you are. I think if you hang on to that and you continue to, as a community, nurture that love each other of the place you're at, it'll build over time.

Last comment. It's not a bad thing when people leave to go somewhere else because that just means that they connected your network to another geography. And so when somebody leaves Saskatoon and goes to the Bay Area, well, now you got a secret agent from Saskatoon in the Bay Area. That's not a bad thing as long as you keep connected to your secret agent in the Bay Area that's sending back messages about what's happening. And when you go out to the Bay Area, you visit them, and when they come back home to visit, you embrace them again.

And that's actually been another powerful thing about not just Boulder, but Colorado generally, because Denver is a pretty big city that's very close to Boulder. It's about forty-five minutes away. And there's been a lot of movement in and out of Colorado over the last twenty years. More into Colorado than out, but those networks are strong.

And so just keep trying to view your inclusiveness of people even when they've left your town. They're still part of your startup community.

Brendan King: Yep. Saskatchewan has secret agents everywhere, and sometimes they come back. So well, thanks, Brad. That was fantastic. You're always generous with your time. It's so much appreciated. I'm glad that the folks here got to experience what I get to experience, multiple times a year. So thank you very much. We really appreciate it. Thanks.

Brad Feld: Alright. Have a good rest tonight, everybody. Thanks. And, Brendan, I'll talk to you soon.

Final Takeaways

Brad Feld’s wisdom is hard-earned and generously shared—from boardrooms to Boulder. His commitment to building strong communities, mentoring with purpose, and approaching business as a long-term, collaborative game left the audience at Uniting the Prairies energized and inspired.

If you’re a founder, investor, or builder of any kind, his insights are a powerful reminder of what matters most: people, purpose, and perseverance.

Curious to learn more from Brad Feld? Check out his books here.

Curious to learn more about Vendasta? Let’s talk, request a demo here.