Brad Feld is a legend in the world of investing, entrepreneurship and mentorship. He is co-founder of the Foundry Group, Mobius Venture Capital and Techstars. Brad was an early investor in Harmonix, Zynga, MakerBot, and Fitbit and has written extensively on venture capital investing and entrepreneurship. Brad’s latest book, Give First: The Power of Mentorship, was released earlier this year.
Brad joined Robert Glazer on the Elevate Podcast to talk about his approach to giving, leadership and cultivating thriving businesses.
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Listen to the podcast here
Brad Feld On Leading Through Giving And Transforming Startups
Our quote for today is from Oprah Winfrey. “A mentor is someone who allows you to see the hope inside of yourself.” My guest, Brad Feld, is a legend in the world of investing, entrepreneurship, and mentorship. He’s the co-founder of the Foundry Group, Mobius Venture Capital, and Techstars. Brad was an early investor in Harmonix, Zynga, MakerBot, and Fitbit, and has written extensively on venture capital investing and entrepreneurship. His latest book, Give First: The Power of Mentorship, was released earlier this year.
Brad, welcome. It’s great to have you on the show.
I’m delighted to be here.
I always like to start from the beginning. What were you focused on in your early teenage years? What interested you? Did you have that entrepreneurial bug?
I didn’t have the word for it, but I definitely had the answer.
You had the lemonade stand to prove it?
Early Entrepreneurial Bug & Computer Interest
No, by the time I was a teenager, I was really into computers. This would be in the ‘90s, late or early ‘80s. I got an Apple II from my Bar Mitzvah. It was a very early Apple II. My Bar Mitzvah was in 1978. I had an Apple II.
It’s an expensive computer, probably.
It was expensive. I had a cassette recorder, no disc drive.
Computers, if I think back, were probably twice the price today in dollars back then. Even if I think about when my dad got the first one, I was like, “What are we going to do with this thing?”
There’s this constant $3,000 price point for a fully loaded whatever it is that existed in the personal computer world. I got into computers as a teenager. I played around with writing software, learn how to program initially in BASIC and then in Pascal. My uncle, Charlie, was one of a handful of people who, in that time frame, invented or created the idea of a chief information officer. His first title was data processing manager or something like that. He was really impactful on me early on because I was twelve years old, and he took me to the Frito-Lay data center in downtown Dallas.
He had stuff to do on a Saturday. He did a bunch of stuff he had to do, and he just sat me down in front of a screen and gave me this big book. It was a black book that was titled A Programming Language. The programming language was APL, which literally stood for A Programming Language. I don’t know, I lost myself for 6 or 7 hours, messing around with it. That was like this very early beginning of all this stuff that by the time I was finishing high school, I had done some entrepreneurial things. I didn’t have the word for it. I’d written a piece of software with a friend of mine.
It was probably that Brad doesn’t pay attention in school and doesn’t listen.
No. I was a good student. I was a good kid. I was part of the nerd crowd.
Sometimes the kids who got those computers were just like, “I’m going to do this,” and like, “I don’t want to do the rest of that stuff.”
I liked all the pieces, but that’s how I got started.
You went on to found your own company, which you were saying you came up with a very unique name for, right?
Founding & Selling First Company (Feld Technology)
Yeah. In college, I started a couple of companies that failed. The first successful one, I named after my dad. The company was named Feld Technologies. It was me, a guy, Dave Joke, and then my dad was an advisor to us. We gave him a little equity in it. We had ten shares of stock that we used to capitalize the company with a dollar share, ten shares.
At the end of it, we still had ten shares of stock because we never raised any money. Fortunately, each year was worth a lot more than a dollar. That was pretty powerful. I was in my late teens, early twenties. We built a business in Boston. It grew to be a couple of million dollars a year. It was very profitable. We made about half a million dollars, bottom line. We didn’t really have a clue what we were doing.
We figured it out along the way. Even then, like in the late ‘80s, early ‘90s, companies like Apple had turned into meaningful businesses, but the idea of entrepreneurship as a thing wasn’t all that. It wasn’t being called that. It wasn’t all that accessible. It was pretty hard early on, probably from ‘87 when I graduated college to maybe 1991. I didn’t really find my people. Even though I was in Boston, like, and there were plenty of other companies in Boston, but I just like, there were no linkages.
Had you been in Silicon Valley at the time? Do you think that would have been different?
No, I don’t because I had a couple of customers in the Bay Area. I was in and out of the Bay Area. I was in LA a lot. I think there was a different dynamic surrounding MIT and Stanford around entrepreneurship and company creation, but there still really wasn’t the language for it in the same way.
It wasn’t in the zeitgeist.
Yeah, there were certainly real. I think about founders in Boston in that time period who were creating amazing companies that were really important. Dan Bricklin would be an example. Mitch Kapor would be an example. Of course, there are all the mini computer companies that were still in Boston.
A lot of the software businesses from that on Route 128 would turn into next-generation software companies that became client-server software companies. Of course, Microsoft in Seattle had grown like crazy. It was a different thing. The linkages, the communication wasn’t there. There were some things. I would religiously every month go to the MIT Enterprise Forum wasn’t the MIT entrepreneurship forum.
It was the MIT Enterprise Forum. I meet people like Bill Warner, who created a company called Avid, who was one of my early heroes, and others. Again, it was like, “Here I am. I’m running my little company with my partner, and I’m running around downtown Boston. Where are the other people like me? I didn’t know where they were.”
It’s not easy to find them. Some things have changed. Some things have stayed the same. Boston has a hard time. It seems to develop a lot of talent, but it’s had a hard time keeping it here for a while.
One of the big positive shifts in Boston that made a huge impact was when all the VCs moved from Waltham to Boston. The idea that the venture community was in Waltham, and when I say they moved to Boston, was Boston and mostly Cambridge. The idea that you’re in Boston and you’re in college or slightly out of college, you don’t have a car.
Waltham’s really not a great destination.
How do you get there? It’s a miserable thing or 128 or 495. This concentration of activity that eventually there was always stuff in Kenmore Square when I was in college. Techsquare was this thing that existed, where, right in the middle of the MIT campus, there was a bunch of lists.
Since I’ve been in Kendall Square since 2000, it’s unrecognizable.
The density and concentration have helped dramatically with the network dynamics in Boston.
Kendall’s become a life sciences capital of the world. It’s amazing to watch. You eventually sold your company. You started investing. I have a lot of friends who have sold their companies, started investing for a year, and then find out they really don’t like it or they’re really not good at it. You’ve made a career out of this. What don’t entrepreneurs do well as investors?
A couple of things. It took me a while before I committed to being an investor because from ‘94 to ‘96, I made about 40 angel investments with most of the money that I made from selling that first company. At the time, doing an angel investment a month was crazy. That was not a normal thing. It’s reasonably normal for an active angel investor, but then angel investors might make 1, 2, or 3 investments a year.
Now it’s all safe. It’s just some brands.
Whether I was writing convertible notes or equity rounds or whatever, it didn’t matter. It was just the act of. I took a different approach than I think the traditional conventional wisdom would be, which was that I just wanted to get involved in a whole bunch of new companies getting started. It was at the rise of the commercial internet. There was a lot of that activity, especially in Cambridge. Next, I was youngish relative to people who had sold businesses, sold my first company at 28, and made some bucks.
By ‘94, I’d met a bunch of peers and built a bunch of networks of other founders. Not just in Boston, but also in the Bay Area, also in Seattle, because I spent a lot of time there because of Microsoft, there in New York, because I would go in and out of New York for various reasons. The company that bought mine was based in New York. I was doing all of this investing, as often the first check or one of the very first checks, angel investor, but I was also co-founding companies.
I would act as a co-founder, not an operator. I wasn’t the CEO, but I was a co-founder. I co-founded a half dozen or so companies in that time period, including two that I was co-chair of that ended up going public. A couple that I wasn’t on, but I was on the board of, that went public. I had this crossover dynamic as I was an angel investor, and I was creating companies. Suddenly, in the middle of this, I chose actively not to run a company that I had co-founded in ‘95.
On the heels of that, Amy and I decided to move from Boston to Colorado. In that shift, I accidentally, a year or so later, six months later, ended up starting to work with, for the first year, as an affiliate, which was what I was called. A group of us created a venture fund that was associated with SoftBank. SoftBank at the time wasn’t well known in the US. Masayoshi Son had just started buying some digital media companies.
In the middle of me starting in this affiliate role with them, he did this crazy investment in Yahoo that everybody thought was insane and ended up being hugely successful. That group that I was part of as a subset of the group ended up creating a venture fund that SoftBank sponsored called SoftBank Technology Ventures. The four of us owned the business, but SoftBank was our sponsor.
There was another group that was affiliated with us, people well known in entrepreneurial circles, Fred Wilson and Jerry Colonna. Fred, Jerry, and I, another guy, Rich Levendorf, we’re all working part-time for this amorphous thing that was getting created. In the midst of this amorphous thing, we were doing a bunch of investments. SoftBank, this team that we were part of was doing an investment a week in internet stuff, which again was nuts at the time, people thought was insane.
At the time, it was a crazy time, though. It was probably like today, with AI the closest I’ve seen.
You had a lot of suspension of disbelief by ‘96, or ‘97, that hadn’t happened yet. That happened in ‘98, ‘99, and 2000. In the middle of this, when I say accidentally became a VC, what happened was SoftBank effectively ran out of money. Three of the people who worked for SoftBank and I started a fund, and it took us a year to raise the fund, of which SoftBank put in a small amount of money, but again, it was our sponsor.
Transition From Founder To Investor
That was accidental. I wasn’t very deliberate about it. I didn’t think hard about my partners. I was just flowing with it. At the time, I was about to raise a seed fund of my own with one other person, which was a new thing. It would have been a new emerging thing in that time period. Separately, back to your original question, it wasn’t until the internet bubble collapsed that I really had to decide, “Am I an investor or am I like in these companies?”
By that point, I was no longer a CEO. I was still chair of a number of companies, and being chair is very different than being CEO, and can be very confusing if you’re a co-founder and chair versus the CEO. I woke up one day and I realized, “I was a good CEO. I didn’t like the job.” I was enjoying not being the one in the CEO seat and consequently in the misery of the dot-com collapse and the internet bubble breaking, and just my own storm of mess that I had to deal with. I decided, “I’m not going to be an operator anymore. I’m not going to have this illusion that I can do both of these things. I’m just going to focus now on being an investor.”
Have you had a rubric? I’m sure it’s been updated or consistent, having made hundreds and hundreds of investments. I’m always interested. Do you have a core rubric or test that you look at?
When I started, I had a very simple one. Today, I have a very simple one. There were many perturbations along the way, including a very complicated one at SoftBank, which then became Mobius, which, in hindsight, was idiotic.
With point scoring and stuff.
You got it. The start for me was that I only really cared about two things when I met somebody. I cared about the product. I was always a product person. I wrote my own software in my first company. I wrote software until 1992 in a serious way. I just cared what the product was, not the total available market. There’s a lot of the total available market, who knows?
It was much more like, “What is this thing? Do I get it? Do I care about it? Do I think it matters? Do I want to be a partners with the founders? Do I want to engage with these people? Do they want to engage with me?” Those are really my only two lenses that I was looking at. I constrained myself to areas I knew well. In that time period, I knew software really well. I constrained myself with most of my investments to software. As the internet evolved, I learned a ton. I expanded the things I had a feeling of competence around, but I stayed in areas that I felt like I had a clue about.
I know so many people won’t touch anything if the market’s not big enough, but it’s interesting.
The best markets are the ones on day one. They don’t exist. I never understood what the team did at a seed stage.
It’s not like anyone always says we will just, we just get 0.1% of this trillion-dollar market. I was like, “Other than aircraft, there aren’t a lot of trillion-dollar markets.” Maybe in NVIDIA chips, I don’t know.
You look at the long arc of stories, and the NVIDIA story is a great one. A podcast for podcast listeners. The acquired podcast episode on NVIDIA is phenomenal because Ben and David, who host that podcast, understand that NVIDIA was not an overnight success and almost failed multiple times. The market for their business, like the business today, that market opportunity wasn’t even envisioned until a handful of years ago.
Brad’s Investment Rubric
That was a long time ago. I have probably three things that are my characteristics, too, which will sound very similar. Number one is, do I have an affinity for the product? I don’t have to use the product. I don’t have to be the customer. I just have to care about it. The reason I have to care about it is that I have now invested in so many companies that I don’t care about the product. Every company I’ve invested in has had at least one near-death experience.
Many of them, that near-death experience was terminal. They died. The ones that were huge successes still had at least one near-death experience. If I didn’t care about the product, it was really hard to keep my head in what was going on. Number one, do I have an affinity for the product? Number two, were the founders put on planet Earth to work on this problem right now? Not necessarily the rest of their life.
Every company I’ve invested in has had at least one near-death experience. Many of them didn’t survive. Even the ones that became huge successes went through at least one near-death experience.
That’s a little bit tied to number one. It’s interesting, right?
Of course. I used to talk about obsession instead of passion, because I think any extrovert can fake being passionate about anything. Introverts have a harder time faking it. You get weird bias and effects. Passion is a dumb word because it’s too easy to fake. Obsession is also not the right word, because there are some really positive characteristics in obsession.
Are they going to die trying to solve this problem?
There are some negatives.
I remember seeing the founder of Waze speak, and all the stuff that he went through, and the dude just hated wasting time. He was going to solve that problem.
You look at it, you’re like, “This person is put on planet Earth.” I think one can decide that you might not be right, but you can decide that within 15 or 30 minutes. Again, you might be wrong and you might change your mind after you spend more time with somebody, but it’s pretty easy upfront to say, “You’re here for a mercenary reason around something rather than this is the thing.”
“This is a good opportunity.”
It’s a good opportunity, or you want to be a founder and you want to create a company, versus this is the thing I’m going to make happen when nothing exists. The third is do they want to be partners with me as much as I want to be partners with them. A long time ago, I got tired of chasing founders and chasing deals. In my world, it was never much of a struggle, that dynamic, because I had a lot of people who wanted to work with me.
What I realized was that when I found myself chasing something, it usually meant that either the founder didn’t value what I could bring other than just money. I was a commodity in the context of the engagement, which, by the way, is fine and is a reasonable perspective. I didn’t want to spend my life in those situations. Second, my best outcomes had been the things that nobody cared about. When I think about the things that generated enormous outcomes for me, 100X or more, nobody else would find.
Blue ocean, not red ocean.
I look back at my SoftBank and Mobius time. I have a great memory of a company that was successful. That was red in that language. It was founded in 1999. It was an online calendaring company. You have to go back in time, and you have to understand that online calendaring wasn’t a thing, that the handheld device at the time was the Palm Pilot. You had to physically take it and connect it to a thing that connected to your computer.
It’s a piece of software.
A serial port, and then you had software that was running in the background that somehow magically made what was on the PalmPilot.
I remember that software.
IntelliSync.
I used that.
All of a sudden, the web is now, applications are becoming web-based, and the idea of an online calendar becomes a thing. I don’t know, 30 online calendars get funded. I don’t know, 20, 50. Everybody starts and funds an online calendar. Microsoft bought one, cannot remember which one they bought, AOL, or one of them was called Jump. All the other ones went out of business, except for AnyDay, which is the one we funded, and that got bought by Palm. It wasn’t better.
They needed a dance partner.
I’m like, “I’m not going to fund one of 30 things. That’s not that interesting. Maybe it’s a good business for somebody, but it’s not what I want it to be.”
You focus a lot on communities in your career. In the book Startup Communities, you talk about the Boulder thesis. Could you highlight that? I’m curious about which parts have held up over the past decade and which have evolved more.
This concept emerged right after the global financial crisis. In 2010 or 2011, I started really thinking about this. I wrote this first book, Startup Communities, in 2012. The path to it has a couple of steps. When I lived in Boston in the early ‘90s, I remember that beginning of our conversation, I didn’t know where my people were.
I had this amazing four-day weekend at this event called Birthing of Giants. I went to the inaugural and the very first one. It’s a pay-to-go. I had one resource that was my resource as a founder, other than tech magazines, and that was Ink Magazine. I ran an Ink Magazine from cover to cover. There was this advertisement for this thing called the Birthing of Giants. Founders under the age of 40.
Was it not an EO thing at the time?
EO didn’t exist. In fact, and I shouldn’t say it didn’t exist, YEO, Young Entrepreneurs Organization, was one of the co-sponsors of Birthing of Giants. At the time, YEO had fewer than 100 members worldwide. I see this thing. It’s at MIT Endicott Center. Vern Harnish is the host. I don’t have any idea who Vern is. I apply my business is slightly less than a million bucks. I was worried I wasn’t going to get in, but I didn’t want to lie.
I told the truth. Nine hundred and whatever to get in. I go and I’m surrounded. There are about 60 of us. I have 59 other people who all of a sudden I’m like, “These are the people who are dealing with the same stuff I’m doing from the spectrum of I was with this one of the smallest businesses.” Up to 500 people or whatever, a $500 million business. Daymark, one of the online catalog companies, was there. Ted Leonsis, who was running a company called Red Gate Communications, ended up getting bought by AOL and becoming Steve Case’s partner in the rise of AOL.
Just an amazing collection. I had this four-day weekend. I’m like, “Got it.” I went back home. I told my partner, business partner, who was like, “Yeah, whatever.” I was glad he supported me doing it. I co-founded and joined YEO, which had 101 members. I created YEO Boston. I somehow found some other people through whatever, and we got a Boston chapter started. That expanded from there. I was already doing some things.
There was a thing, Cambridge, I forget what PDL Singers thing was called, but there was something in Cambridge that I started going to every month and dot. In Boston, I’d already had this experience of starting from nothing and building a community. We moved to Boulder. Of course, I had my community in Boston. I moved to Boulder. I knew one person who ironically was Verne Harnish. He moved away six months later.
I didn’t know anybody. Amy and I literally just moved to Boulder because that’s where we wanted to live. I started YEO Colorado, which is about to have its 30th anniversary. We’re having fun because we’re going to have our 30th anniversary. I haven’t been in touch for a while. Now of a sudden, everybody’s getting reconnected for this big anniversary we’re to have. Same thing, like all of a sudden I got my gang.
I had these experiences. I had another one in the internet bubble in Colorado. We created something called the Colorado Internet Keiretsu. There are probably hundreds of internet-related companies in Boulder and Denver where all the founders regularly get together with each other and communicate. That was fascinating to me. Internet bubble crashes, companies start to reemerge. In 2006, we started Techstars.
Techstars starts to become this convening force in Boulder that energizes what is a bunch of activity around entrepreneurship in this little tiny town. Boulder’s only a hundred thousand people, but coming out, reemerging all of a sudden, there’s a lot of linkages between people, that’s really fun and interesting. We use Techstars as a way to concentrate energy around it for 90 days in the summertime and on and on.
I start thinking about this. The global financial crisis happened. The world’s going to end. Every bank is going to be nationalized. Every business is going to have to be run by the government, whatever. We get through that. In 2011, there started to be a reemergence of entrepreneurship and innovation as a powerful force. There was an article written that said to look at these four cities as examples. The Bay Area, which, of course, is in a city. It’s a bunch of cities. Boston, New York, which is also a collection of five cities, and Boulder.
Which one of these is not like the other?
The Boulder Thesis & Startup Communities
Yeah. Boulder fits in like a one block of Manhattan is where Boulder fits. I built on that, and I then reflected and wrote this book, that named this thing called the Boulder Thesis. I needed a framework for it because every business book needs a framework, and it’s super simple. Number one, to build a vibrant, lasting startup community, it has to be led by entrepreneurs. Number two, you have to take a long-term view.
Number three, you have to be inclusive of anyone who wants to engage. Number four, you have to have activities and events to engage people in entrepreneurship. That sounds like. In 2012, it was not at all how people talked about these things. They didn’t call them startup communities. That was labeled by this book. They called them innovation clusters or entrepreneurial ecosystems.
You had to have things like, “To have one of these, you had to have a whole bunch of venture capital, or you had to have a university that was the center of all the innovation, or you had to have support from lots of successful companies in the region that were spinning off people.” Anna Saxenian’s book, Regional Advantage, which she wrote in 1994, was an inspiration for me because she talked about what happened between Route 128 and Silicon Valley, and what those dynamics were from the 1950s to the mid-90s, and what resulted in the difference in arcs of success. I put this together. It was a very anecdotal book.
I use Boulder as the example, my own story as an example, but it wasn’t research-based. It came out with it. Founders loved it. Frankly, a lot of people who were trying to do this in different parts of the world, who were in university or in government or in big companies, grabbed onto it as an idea. Six months later, Adam Grant came out with a book, Adam being an organizational psychologist at Wharton, that was deeply researched called Give and Take.
My reading of that book, I had this a-ha moment that was really powerful for me because in Startup Communities, I had one paragraph in the middle of, I don’t remember which chapter it was in. The paragraph was titled Give Before You Get. The premise was, “If you want to build a vibrant startup community that lasts over a long period of time, you have to be willing to put energy into the system, into the startup community without defining upfront what you’re going to get back.”
It’s not altruism. You expect to get something back, but you don’t know from whom, over what time period, in what form, or in what consideration. If you get all the founders doing that, and you get people around the system, the startup community doing that, you’ll get a flywheel going that becomes very powerful. I said, “I didn’t really think that hard about it. It’s how I behaved.” It’s how I behaved in Boston in the ‘90s.
It’s how I behaved when I moved to Colorado in the mid-’90s. It’s how I thought about my world and my network and how I connected with people and things. All of a sudden, Adam comes out with this book, and he demonstrates that people who lead with a non-transactional mindset over a long period of time have more success than people who don’t.
He defined success more robustly than just power and money, which appeals to me greatly, because I don’t think success is defined just as power or money. Some people clearly do, but I don’t. All of these things in this 2012, 2013, 2014, 2015 are happening in the midst of thinking about in midst of Techstars starting to grow geographically throughout the world. The firm that I’m part of now, Foundry Group, is having a lot of success investing all across the US, not just in Colorado, not just in the Bay Area, not just in Boston or New York.
I’m starting to see this language around startup communities, and the way that the energy of founders and the network and connective tissue between founders are reinforcing that. You’re seeing it in lots of places. You can talk about the huge success and power of the thing that’s called the PayPal mafia, and just the network of things that emerged from that. There are lots of those all over the place, but that one was the one that so many people point to because it was both powerful and provocative. Ten years later, when I look back from 2025, it holds up really well. I made a lot of mistakes in that first book, which I fixed in a second edition.
I was going to say, a lot of that sounded like a preview to Give First. I guess that was inspired by Adam’s work, too. I’m guessing a little bit.
Give Before You Get was this philosophical idea that I had. It’s not religion, it’s not a set of rules, it was just a philosophy. It got embedded and incorporated into the behavior of Techstars at that time. #Givebeforeyouget is a crappy hashtag. If Twitter’s only 140 characters. A guy had Techstars, Greg Cochran, who one day tweeted something with #GiveFirst. That’s where that emerged. That philosophy was not new. I didn’t invent it.
It wasn’t my creation. It was a description of a set of things that was a way I had been behaving for a long time, where I’d be willing to enter systems, non-transactional, positive sum, where both parties or all parties benefit, not necessarily equally, but benefit. Different than win-win. I think win-win is now just lame ass marketing and sales language. When somebody says, “This is going to be a win-win,” I say, “Tell me again. What are you trying to take from me to get your win?” Positive sum, I think, is powerful.
This idea that life and everything is a multi-turn game. You want to engage with people multiple times over a long period of time. All of this munging together of stuff was happening in my head and in my work. At Techstars, there were two pieces of it that were also reinforcing for me what was happening. One was the impact Techstars was having on what today I could probably label the global democratization of entrepreneurship. At the time, I didn’t have the words for.
The idea that was really important to me was that it wasn’t that if you’re serious about being a tech entrepreneur, you should just move to the Bay Area. I hated that line. I hate it when I hear that. My view was “No, you should go where you want to build your lives.” There are lots of different reasons people choose where they want to live.
Anyone anywhere in the world should be able to build a significant, scalable company if they want. That was one. The other was this idea that we were learning a lot about what was effective versus not at Techstars, which was mentorship. We learned a lot about what worked and what didn’t work.
Again, not in the context of creating a bunch of rules and saying, “You must do this, you must do that, you must do this,” but trying to separate between reflecting back on my experiences, what had been effective versus not when I was being mentored or when I was a mentor, what I did that was effective or not. Same with observing a whole bunch of others. Those things continued forward in my thought process.
Let me ask you, the book is a lot about mentorship, and you talked about the impact on you personally. I think a lot of people seek out a mentor. I saw mentors like, “Let me find someone who’s around a few turns on the road ahead because man, they’re going to be able to tell me where the potholes are and what’s going on.”
One of the recommendations in the book, which I like and agree with, and I think I’m probably not as good at, even though I encourage other people to do this while I’m coaching them, is to be socratic. Can you talk about what that means and why it’s so hard for people, but why it’s so important in mentorship to be socratic when you can be like, “Look, when you get to 30 people, hire an HR person.” It’s just obvious. That might be the right answer.
The Power Of Socratic Mentorship & Storytelling
There are a couple of pieces layered together in that. First, being Socratic doesn’t mean just asking questions with no place to go. Anybody who’s been a founder who has a board has a board member who does that. They just keep asking questions, but you have no idea where they’re going with the questions. That’s useless. One of the powerful things about being a mentor is guiding the mentee towards an answer, but not giving them the answer.
Something I learned from YEO, from a thing in YEO called Forum. You tell stories from my experience. You don’t say, “When you hit 30 people, you should hire HR.” There’s like 50% of the world when you say that, the very first thing they’re going to do is say, “I’m not going to hire an HR person because they’re just going to be obnoxious. You’re going to tell them to do something, and they’re just going to be reliving their childhood.”
They’re going to go to a concert and be caught on a Jumbotron.
That’s right. They get stoned. They’re not going to do whatever they’re supposed to do. If you say, “Look, here’s what I experienced when my company got to about that size. I had one company where we hired an HR person, and this is what happened, and here are the benefits of it. Another company where we didn’t, and by the time we got to 100 people, I realized we probably should have earlier. Let me give examples.” Number one is this idea of guiding. Number two is the idea of using your own experience.
Storytelling, not necessarily questioning.
The questioning helps you get deeper into the problem. Most problems when people present them to you are not the problem.
This is the whole presentation format for you, too.
If you’re not a critical thinker, fine. You’ll always accept the first thing you hear is the problem is the problem. Most people, I think, who are entrepreneurs aspire to be critical thinkers and are trying to figure out answers to hard problems. The first thing you come up with is probably not the answer to the problem because you haven’t understood what the root cause is.
It requires a little more vulnerability. I remember three different presentations about how someone should split equity. Eventually, over the years, the group was like, “This is the same presentation.” The person was like, “No, it’s not. This is a totally new case.” We’re like, clearly, there’s a problem with how you start ventures with other people. That is more of the problem here.
Let’s talk about that, right? It’s not what the equation was. It’s like, what’s the expectation, the style going in? You, as a mentor, use a question or questions to dig deeper into the problem. You use your experiences to guide you through the problem-solving process. You have to be comfortable that what you’re providing to the mentee is just data.
When the mentor-mentee relationship becomes a peer relationship, you win the game.
The second you start shifting into this is the answer. I like to call it the finger wag, or it’s the thing my father does, “Brad, you should.” The second you flip into that as a mentor, you lose your audience for lots of different reasons. You have to be comfortable that you go through this. By the way, you’re not the only mentor.
The mentee might have multiple mentors, and the multiple mentors might be giving conflicting data. The interesting thing about conflicting data from people’s experiences is that if you’re on the receiving end of some of that while you’re trying to solve a problem, all of a sudden, you have some richness around the problem, versus if you have an N of one, maybe it’s right, maybe it’s not, no idea.
As you start to have not N of a zillion, but as you have more, that’s useful. There will be somebody listening and saying, “Yeah, but isn’t conventional wisdom good enough?” The answer is, “From my frame of reference, isn’t pattern matching good enough?” I hate that phrase. Many people extrapolate from patterns from one positive experience, and this worked for me once, and it was very successful.
By the way, it worked in a time, I cannot tell you, I wrote a Friday Ford on this, and someone wrote to me like, “I think it was about the Dollar Shave Club.” They couldn’t recreate it. No one could make that, it just hit a mark in a time, and she said, “Do you know how many people have come to me and just make us the Dollar Shave Club ad?”
Those things all fit together. It’s interesting if you step back and say, “There’s something here.” What I’ve tried to do with the book is, in the part on mentorship is take a bunch of these simple ideas like be socratic, the guy doesn’t control. These things all came from the Techstars Mentor Manifesto that David Cullen came up with in 2010. It’s not intended to be rules that would be perfect, or if you follow these things, you’ve got to check mark.
It’s much more around the idea of here are some things to think about that can help you be more effective as a mentor. As a mentor, pick and choose, mold it to your own style, and figure out how it works in your own way of communicating. There’s a really powerful magic trick that anybody in YEO or YPO will understand. When the mentor-mentee relationship becomes a peer relationship, you win. You win the game.
In YEO or YPO, like the group that’s talking, your group that’s talking to this one guy that’s had to deal with equity three different times over the years, you’re all peers. In that moment where you’re having the forum session that you’re having, which is the label that YEO and YPO put on this particular type of engagement, he’s the mentee, and the rest of the group are the mentors, but you’re all peers.
The Power Of Peer Learning & Shared Wisdom
When you share stories, as you know, one of the best ones I ever got was someone else’s presentation. All the story sharing was like, “I’m going to run into this someday.” I’m going to remember this.
Even better, you’re in the middle of listening to someone’s story, and to go, “That’s my problem. I know what to do. I have a thing to do that I didn’t get.” You have these moments, whereas peers, especially groups of peers, you have unlocks of things that you’ve been struggling with, which, if you’re struggling by yourself, you can struggle forever. If you’re working with just your business partners or your management team, or your board, you can struggle forever.
Even if you’re dealing with one mentor, you’re still not getting the dimensions of thoughts that cause the pieces to click into place. For me, there’s a category of person I encounter all the time, I now call the male version of that Mr. Smarty Pants, and the female version of that Miss Smarty Pants. It’s a person I don’t like. Most of the people in the room that I’m in are smart. I don’t care who’s the smartest about any particular thing. They’re all smart. The goal is not to prove that you’re the smartest. My goal is to learn as much as I can from the other smart people in the room. That’s that.
A dichotomy you write in this book a lot about giving and mentorship, and time. I know you’re super giving with your time. I was glad you addressed this. You also talk about being really good at saying no in your life and in your writing, and acknowledge that there are people in these environments who are takers. How does someone think about navigating, or how do you evaluate whether someone is worth their time or mentorship, rather than if they’re in it for the wrong reasons? How do you spot takers, I guess?
I don’t think I’ve ever been particularly good at spotting them a priori. What I have allowed myself to do is I’m not just willing to take risks. I’m willing to engage with someone. When I realize I’m in a relationship that really is one way, the person is taking and you can eventually start to understand them because they’re the people who keep asking you for things and are not giving you things. It’s some weird version of just one more thing.
My guess is that everybody listening has a family member like that, where they don’t understand the boundary when they should stop asking for another thing. Whether that thing is time or money or attention or whatever. Generally, I just approach every relationship from a positive frame of reference. I try to model my behavior consistently, but I’m not perfect, so I screw up. When I find myself in a position where it’s not satisfying, I don’t cut the person off. I don’t delete them from my world.
There’s a different reason why I decide not to engage with a person at all, and that’s usually they’ve crossed some line around trust that’s really foundational for me. There are a few of them. Another comment here, I also have a lot of, everybody has broken relationships. I’m about to turn 60, you can not go through life and not have some close relationships that have failed or broken.
I try to in all of those situations, as long as the person hasn’t crossed for me, red line or whatever you want to call it, or even has, but I’m like, “I’m not going to have the same relationship with you going forward, but the dynamics of our relationship are now up to you. I’m open to continuing to have a relationship, but I totally get if you don’t want to have a relationship.”
Even in the breakups, again, not perfect at this, but I try to have this view that we’re all flawed. I’m flawed. Everybody else is flawed. Everybody makes mistakes. Everybody hurts each other. That’s just a human condition. What’s more important for me is to be internally consistent as much as I can be recognizing those flaws. Over time, just try to learn and get better from the situations that are really negative in the same way when you have a company fail that you’re an investor in or are involved in.
The business failed, but you’re not dead. The business failed, and I learn from it. There are a lot of people who are like, “The business failed, I must run away as fast as possible,” or “The business failed, it was somebody else’s fault.” It happened because of something out of my control. It doesn’t have to be business. It can be a project, it can be anything. In those situations, I don’t revel in them. I’d much rather have.
You might as well learn something.
At least allow yourself the grace to understand that that’s part of it. Think about leaders today and the leadership that we see modeled, where there are some leaders who are unable to acknowledge their mistakes. That can be successful and effective. It’s not my style. It’s not the way I want to be. Frankly, I don’t think it’s effective, but it’s up to other people to judge me.
It’s funny, like you mentioned, the family and the boundary. There’s a story that brings it all back together for me. For me, this probably violates the form confidentiality, but it’s so generic that it won’t mean anything.
Don’t say that. Don’t say the people’s names and don’t say the company.
No. You’ll see it wasn’t a business issue. It was a very common thing. Someone was dealing with a family gift thing and the expectations that it created. I can tell you the room. This is twelve years ago. I can tell you the room we’re in, and I was fascinated by everyone’s story, and over the years, I remembered those situations as those situations came up.
Actually, to bring it all full circle, because I’ve been in subsequent, ironically, well, now multiple discussions around that and forums over, because it’s a very common topic of family dynamics and generosity and whatever. Basically, most people like they’re pretty happy to do it except when the people start treating it as an entitlement and aren’t thankful, which is obvious in some ways.
It’s funny, I can remember those stories. I can remember exactly what people told me, and I carried it forward for years. It came full circle into the give-and-take thing. Even a year or two ago, there was a similar discussion. People are like, “Look, as long as people are appreciative, I’m happy to do it.” My problem is when they’re not, and they expect it. That’s just tied into everything you just said.
Totally agree. As somebody who’s tuning in, as you reflect on that dynamic of what you described, there were a couple of things happening in that forum, which is what you could get from it by just participating and observing. It’s one of the things I think that in the mentor-mentee dynamic in any environment, people miss, which is part of my own joy in so many of these things, which are the unexpected moments of insight that came from being in certain situations.
Where people were discussing certain kinds of things, often those that were not what I expected to be discussing, or what the problem was I was trying to get at, or solve, or understand. You can say, “That’s obvious. That’s how life works.” Many of us try to control and constrain our time so that we don’t have these random things going on. I remember somebody saying to me, “I don’t have three hours a month to sit around and go to a forum.”
That was literally, the guy put his hand, the learning chair, and a membership to my hand on me. I was like, “I don’t have time to go to this training thing. This forum is like, you need this more than you realize if you cannot go to this.” I’m like, “How’s my business going to run while I’m at forum training?”
It’s the dynamic of how we spend our time. Early on, in my 20s and my 30s, I was extraordinarily busy all the time and incredibly overworked in 100-plus hours a week. Even into my 40s, traveling all over the place constantly. Now trying to carve out time to think about things deliberately because I recognize the value of it, but carving time out for my time with Amy or my time for myself.
Over time, Charles can start to look at it and say, “If I actually am understanding the problem better and spending time on the problem rather than running around like crazy reacting to whatever’s going on, I probably can actually be a lot more effective with a lot less energy going into it.” That opens up time for me to explore different things that I hadn’t thought about.
You see that person perfectly for the last question, I like to ask, I always say that this is multivariant. It can be singular or repeated or professional or personal, but what’s a mistake that you’ve made that you’ve learned the most from?
Learning From Mistakes & The Discipline Of “Default No”
I have a very long list of mistakes that I would make for the third time. I’m not going to make that mistake again. I make it the fourth time. One of my chronic mistakes to this day, which I have tried hard to get through, is not being able to flip from what I call default yes mode to default no mode effectively.
I used to always be in default yes mode, and in default yes mode basically means I’d say yes to everything. Part of my job as an investor, I say no constantly. Amy would say to me every now and then, “Why in the world are you doing that? Why did you commit to doing that thing?” I said, “My no-counter got up to 50, and I just had to hit reset. It starts back at zero. I just need to say yes to something.”
Even as I’ve gotten older and I modulated my time a lot better through lots of different things, a couple of years ago, I went into what I called hibernation, which for me was just stopping, not eliminating, stopping anything that had a public profile, all social media, blogging, podcasts, public events, things like that. I didn’t make a pronouncement, “Now I’m going to stop blogging and maybe you should pay attention to me sometime.”
I just thought, and I did that for a variety of reasons. When I came out with to the point where I was ready to publish Give First, which was last December, and I knew it would come out sometime, six months later from the time you have the draft to go to the publisher, ready to time at which the book comes out. It’s a process, and that’s fine.
I’ve done it enough times. I know the process was. I talked to Amy a bunch about this. I consciously decided to come out of hibernation for a period of time. I bound it, I said to myself, and then I publicly said it pretty soon after, because I felt like I wanted to, that I was going to un-hybernate for six months, so from April to the end of October. Now, in the middle of August, when we’re talking, I wish I had bound it to three months.
I don’t know if we wouldn’t be having this conversation. It’s just know that self.
We might not be having it. For me, just the boundary dynamics of that, the underlying personal thing around that is I’m struggling. I got COVID for the first time very badly a year ago, and I’ve been struggling with what I now at least know as the syndrome of long COVID, which has everything to do with fatigue and energy levels.
It’s like anything that if anybody’s listening has an autoimmune disease, and you probably understand how miserably Western medicine has failed the entire category of autoimmune diseases. If you’re a COVID denier, you’ll be like, “He’s just a whiny little kid.” I can tell you that there’s a whole bunch of stuff going on physiologically in me that wasn’t going on.
You’re a marathon runner.
I’m a marathon runner who goes for a three-mile run and has to lie in bed for a day afterwards now because I’m so exhausted. I didn’t really get my mind around the emotional amount of energy that would go into this versus just the physical. That’s the underlying thing. That said, I’m happy doing this. I’m having a good time.
I put that in that same category. I haven’t always had a hard time modulating those things well. I’ll give you one other that’s in the same category. If I get to do it’s multivariate, get to do another one. I think I’ve gotten much better at this. I describe my only regrets now, and I talk about this in Give First.
The Mistake Of Passive Avoidance
My only business regret, I shouldn’t say that, plenty of personal regrets that have fallen in a different category. My only business regrets when I look back are not things I failed at, not things I started that didn’t work, not relationships that went off the rails somewhere or not, whatever. There are situations where I identified and knew there was a problem. I was aware that there was a problem, and I passively avoided it.
I separate passive avoidance from active avoidance. Active avoidance is there’s a problem over there and I’m not going to deal with it, or there’s a problem over there and hey team, if somebody wants to go deal with that problem, go for it, but it’s not my problem. That’s active. That’s totally cool. That’s a different thing. Passive is you know it, you see it, and you know you should do something about it.
You lie to yourself.
Like, “Maybe it’ll get better,” or “I’m too busy, or “I don’t want to deal with it right now, “or I’m too tired or whatever.” When I look at the last 40 years of what I’ve done and been involved in work, in business, all of my regrets, I can link back to moments of passively avoiding when I knew there was a problem addressing.
All of my regrets can be traced back to moments when I passively avoided addressing a problem I knew existed.
My answer would actually be very similar to that. I can relate to that. Brad, where can people learn more about you and your work?
I’m easy to find. I’m on Feld.com is my website. My email is remarkably easy to guess because my website is Felt.com, so it’s Brad@Felt.com. Feel free to send me a note. I am not particularly engaging in anything social media oriented, even though I have a at be felt on Twitter or X or whatever it’s called. I have a LinkedIn account. If you want to engage with me in a real way, send me an email. I try to respond to everything. Thanks for tuning in.
Brad, thank you for sharing your story and your journey with us.
If people end up getting the book, as I say this for all authors of all books, including Robert and his books, anyone who ever writes a book, if you read the book and you like it, leave a review. The hierarchy of places to leave a review today, of course, anything on social media is additive, but Goodreads is the top of the hierarchy, and Amazon is next, even though Amazon owns sponsor.
I know it is funny that they haven’t joined those yet.
If you don’t like the book, my request is to throw it away and not tell anybody.
Perfect. I like that. I may steal that line.
That’s all yours.
You can learn more about Brad and give first on the episode page at RobertGlazer.com. If you enjoyed our episode of the show in general, I have a small favor to ask. That is, we just take a minute and share this conversation with Brad with someone you think would appreciate or learn from it. Thanks again for your support, and until next time, keep elevating.
Important Links
- Brad Feld
- Brad Feld on LinkedIn
- Brad Feld on X
- Foundry Group
- Techstars
- Give First: The Power of Mentorship
- Startup Communities
- Regional Advantage
- Give and Take
- Brad@Felt.com
- Robert Glazer
