Ep. 3 Brad Feld decoding entrepreneurship with Dan Saks

Decoding Entrepreneurship: Brad Feld Explains How to Thrive

A CONVERSATION WITH A RENOWNED STARTUP MENTOR

42 min

Ep. 3 Brad Feld decoding entrepreneurship with Dan Saks

42 min

Every entrepreneur spends a lot of time thinking about their business, but for Brad Feld, it's not enough. Founders also need to be mindful about their work and the impact it has—on the market, on their colleagues, and on their own wellbeing. Hear the legendary investor and startup mentor talk about building businesses, coping with change, and remembering to be kind.

“When you find yourself in an unhappy place, or in a rut, or feeling exhausted, go back to simple things that you used to do that worked for you. Take them as bite-sized chunks rather than radical transformation."

Quick takes on...

How Investing Has Changed the Business Landscape


"It's been pretty amazing what has happened around entrepreneurship globally and the democratization of innovation, the democratization of entrepreneurship, the notion that you can create startup communities and entrepreneurial companies all over the world."


Managing a Team Through Uncertainty


"Number one, eliminate uncertainty. I believe employee uncertainty about what's going to happen is a great cause of stress for employees of any company, but especially for fast growing companies. You always have this uncertainty of, are you going to succeed? Are you going to survive?"


Overcoming Mistakes


"Own your mistakes, apologize quickly with real apologies. When you make mistakes, don't say, 'I'm sorry, you feel that way,' but just say, 'I'm sorry.' Listen, respond, engage. Don't try to solve the other person's problem. That is not your problem to solve, but be empathetic and be responsive to it."

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Meet your guest, Brad Feld

Managing Director, Foundry Group

Brad Feld spotlight on Decoding Digital podcast

Brad has been an early stage investor and entrepreneur since 1987. He is also an art collector, long-distance runner, and avid reader. Prior to co-founding Foundry Group, he co-founded Mobius Venture Capital and Intensity Ventures. Brad is also a co-founder of Techstars, a seed accelerator. Brad is a writer and speaker on the topics of venture capital investing and entrepreneurship. Get a copy of his latest book The Startup Community Way.

Episode transcript

Brad Feld: [0:04] Number one, eliminate uncertainty. I believe employee uncertainty about what's going to happen is a great cause of stress for employees of any company, but especially for fast‑growing companies, because you always have this uncertainty of "Are you going to succeed? Are you going to survive? Is this company going to be around?"


Daniel Saks: [0:21] This is "Decoding Digital." I'm your host, Daniel Saks. Every episode, we hear from someone who is working to build something new in the digital economy. Each guest has a unique perspective to share. Together, we work to understand or decode a trend that is shaping our digital world. Today, I'll be decoding entrepreneurship with Brad Feld. Thinker, writer, activist, runner, mentor, investor. My guest for today's show is all of these things and more.

Brad Feld started his first company in 1987 while he was still in school at MIT. Since then, he has gone on to found several venture capital firms and a highly respected seed accelerator called Techstars. Today, he is Managing Director of Foundry Group, a venture capital firm based in Boulder, Colorado that has invested in successful companies, including Fitbit, SendGrid, and, in the spirit of full disclosure, our company AppDirect. Over the years, he's written more than 10 books, including the bestselling "Venture Deals."

Not only is Brad something of a legend in the startup world, both in Boulder and across the world, but he's also one of the most thoughtful and mindful people you'll ever meet. We're honored to have him as an investor. I'm grateful that he's taken the time out of his schedule to be on our podcast. Hi, Brad. We're thrilled to have you here on the show today.


Brad: [1:41] Thanks for having me.


Daniel: [1:43] Certainly. You've clearly done so much over your career as an entrepreneur and an investor. When did you know that this was going to be your life's work?


Brad: [1:50] I never really worked for anybody. Well, before the word entrepreneur was used regularly, I was behaving in an entrepreneurial way. As a teenager, I had your typical teenage jobs, working maintenance at a tennis club and then working in a fast food restaurant. I got fired from each of those jobs. I didn't like them. I was probably not a great employee in the context of the work. I probably did the work but didn't do it with any sort of vigor.

In high school even, I started a tutoring business for the SAT. Early on, even before I was an adult, I really had this sense of wanting to work for myself, wanting to not be constrained by whatever the norms were, and have the freedom to explore different things.

I did work for a software company when I was in college that I started between high school and college. I got paid 10 bucks an hour, but I got five percent of revenue for the products that I developed. The concept of equity didn't really apply to that particular company. I didn't understand it at the time.

It was an oil and gas software company. The oil and gas industry runs off royalties, and royalty rates, and that sort of thing. While I was in college, I'd literally get checks in the mail each month for a thousand dollars or $2,500. One month, I got a check for over $10,000, which was a remarkable amount of money. It was a real reinforcement of my effort producing a thing ‑‑ in this case a piece of software ‑‑ and then having variable compensation based on the value that's created over time.

That whole philosophy got woven in pretty early. I was always a computer guy and a nerd, but I was also interested in business, and today ‑‑ this is in the 1980s ‑‑ today one would have said, "I was interested in entrepreneurship," but the linkage of those two for me started early.

I was really fortunate in terms of my timing. I was in college from '83 to '87, so the Mac had come out. In high school, I got the experience of the Apple II, so I was a kid during the first save of the personal computer stuff, but I was becoming a young adult as entrepreneurship was starting to rise. From college forward, I've always had my own business, or I've been an entrepreneur, or I've been an investor in other people's businesses. It's just been the way I've lived my whole life from that point.


Daniel: [4:39] When did you become a venture capitalist?


Brad: [4:42] I sold my first company in 1993 to a public company. I had a partner. We really had never thought about selling the company, so that was random. We had a business that was self‑funded, and we made money every month. Business was growing. We got approached by a public company that was buying lots of companies. It took us about six months to decide to sell the company, but after we sold the company, I took almost all the money that I made from that deal, a couple million bucks, and over a two‑year period, I bought a house, but then over a two‑year period, I invested in about 40 companies.

This was $25,000 to $50,000 angel investments, or today even called pre‑seed investments that help start some of these companies. I knew nothing about investing when I made my first angel investment, and so it was a very rapid learning experience as an extremely early‑stage investor. My timing was quite good. It was 1994 to '96, so those seed investments were done at the beginning of the rise of the commercial Internet. From that, I ended up accidentally becoming a VC.

The rise of the Internet bubble was incredible at many levels. I was also the co‑founder of a couple of companies, some that succeeded in the Internet bubble, and some that looked like they were going to succeed and then crashed incredibly hard. One of my biggest painful failures was a company that I co‑founded in 1996, and had a roughly three billion‑dollar valuation in 2000. It was bankrupt in 2002. Just the experience of those kinds of things was unbelievably formative.

Brad Feld: [0:04] Number one, eliminate uncertainty. I believe employee uncertainty about what's going to happen is a great cause of stress for employees of any company, but especially for fast‑growing companies, because you always have this uncertainty of "Are you going to succeed? Are you going to survive? Is this company going to be around?"


Daniel Saks: [0:21] This is "Decoding Digital." I'm your host, Daniel Saks. Every episode, we hear from someone who is working to build something new in the digital economy. Each guest has a unique perspective to share. Together, we work to understand or decode a trend that is shaping our digital world. Today, I'll be decoding entrepreneurship with Brad Feld. Thinker, writer, activist, runner, mentor, investor. My guest for today's show is all of these things and more.

Brad Feld started his first company in 1987 while he was still in school at MIT. Since then, he has gone on to found several venture capital firms and a highly respected seed accelerator called Techstars. Today, he is Managing Director of Foundry Group, a venture capital firm based in Boulder, Colorado that has invested in successful companies, including Fitbit, SendGrid, and, in the spirit of full disclosure, our company AppDirect. Over the years, he's written more than 10 books, including the bestselling "Venture Deals."

Not only is Brad something of a legend in the startup world, both in Boulder and across the world, but he's also one of the most thoughtful and mindful people you'll ever meet. We're honored to have him as an investor. I'm grateful that he's taken the time out of his schedule to be on our podcast. Hi, Brad. We're thrilled to have you here on the show today.


Brad: [1:41] Thanks for having me.


Daniel: [1:43] Certainly. You've clearly done so much over your career as an entrepreneur and an investor. When did you know that this was going to be your life's work?


Brad: [1:50] I never really worked for anybody. Well, before the word entrepreneur was used regularly, I was behaving in an entrepreneurial way. As a teenager, I had your typical teenage jobs, working maintenance at a tennis club and then working in a fast food restaurant. I got fired from each of those jobs. I didn't like them. I was probably not a great employee in the context of the work. I probably did the work but didn't do it with any sort of vigor.

In high school even, I started a tutoring business for the SAT. Early on, even before I was an adult, I really had this sense of wanting to work for myself, wanting to not be constrained by whatever the norms were, and have the freedom to explore different things.

I did work for a software company when I was in college that I started between high school and college. I got paid 10 bucks an hour, but I got five percent of revenue for the products that I developed. The concept of equity didn't really apply to that particular company. I didn't understand it at the time.

It was an oil and gas software company. The oil and gas industry runs off royalties, and royalty rates, and that sort of thing. While I was in college, I'd literally get checks in the mail each month for a thousand dollars or $2,500. One month, I got a check for over $10,000, which was a remarkable amount of money. It was a real reinforcement of my effort producing a thing ‑‑ in this case a piece of software ‑‑ and then having variable compensation based on the value that's created over time.

That whole philosophy got woven in pretty early. I was always a computer guy and a nerd, but I was also interested in business, and today ‑‑ this is in the 1980s ‑‑ today one would have said, "I was interested in entrepreneurship," but the linkage of those two for me started early.

I was really fortunate in terms of my timing. I was in college from '83 to '87, so the Mac had come out. In high school, I got the experience of the Apple II, so I was a kid during the first save of the personal computer stuff, but I was becoming a young adult as entrepreneurship was starting to rise. From college forward, I've always had my own business, or I've been an entrepreneur, or I've been an investor in other people's businesses. It's just been the way I've lived my whole life from that point.


Daniel: [4:39] When did you become a venture capitalist?


Brad: [4:42] I sold my first company in 1993 to a public company. I had a partner. We really had never thought about selling the company, so that was random. We had a business that was self‑funded, and we made money every month. Business was growing. We got approached by a public company that was buying lots of companies. It took us about six months to decide to sell the company, but after we sold the company, I took almost all the money that I made from that deal, a couple million bucks, and over a two‑year period, I bought a house, but then over a two‑year period, I invested in about 40 companies.

This was $25,000 to $50,000 angel investments, or today even called pre‑seed investments that help start some of these companies. I knew nothing about investing when I made my first angel investment, and so it was a very rapid learning experience as an extremely early‑stage investor. My timing was quite good. It was 1994 to '96, so those seed investments were done at the beginning of the rise of the commercial Internet. From that, I ended up accidentally becoming a VC.

The rise of the Internet bubble was incredible at many levels. I was also the co‑founder of a couple of companies, some that succeeded in the Internet bubble, and some that looked like they were going to succeed and then crashed incredibly hard. One of my biggest painful failures was a company that I co‑founded in 1996, and had a roughly three billion‑dollar valuation in 2000. It was bankrupt in 2002. Just the experience of those kinds of things was unbelievably formative.

The rise up was intense. You could, if you sneezed, you made money. Terrible ideas were funded all over the place. At the peak of the Internet bubble, the amount of money being funded into companies, even at the early rounds, again those $250,000 seed rounds in 1994 had all of a sudden become $20 million seed rounds in 2000. The collapse was much faster than the rise. Even though the rise was over a three or four‑year period, the collapse was a 12‑month period, and it was just a sharp, downward, every day was worse than the previous day.

There was no saving anything, and it was just a matter of... The cliches abounded, and my favorite one was, don't catch a falling knife. Like you'd hear that 17 times a day. It's like, "The cliches are not helpful. Like everything is just [bleep] up, and it's time to try to deal with it, and figure a way through." Of course, some of the companies ended up being successful, but the period of time was very formative.

It then led to a period of time I refer to as, for me, as the grind, which was, after my world fell apart as an investor in the companies' dynamics in 2001, 2002 to 2007 for me, maybe 2006, was just a grind at Mobius.

Dealing with Mobius, the firm scaling back, we scaled back from, I think at the peak, 70 people. Today, literally I'm the only person that manages any of the Mobius things, and we're basically almost done finally with all those funds. I think we'll shut the last fund down this year. That's 20 years later of managing that stuff.

The experience of trying to navigate through new investments against the backdrop of a collapse, against the backdrop of entrepreneurship being way out of favor, from 2003 to 2006 or 2007... Web 2.0 started to emerge in 2004, 2005, so there was a little bit of energy starting again, but it was very, very diminutive.

Interestingly, as things started to scale back up on the entrepreneurial side, we ran right into the teeth of the global financial crisis, and 2008 to 2010 was a pretty challenging time overall. We raised our first Foundry Group fund in 2007, which was not a particularly easy time to raise a fund, especially a new fund, especially against the backdrop of all the history of venture still very out of favor in 2007.

If you then take that and traject forward 13 years, it's been pretty amazing what has happened around entrepreneurship globally and the democratization of innovation, the democratization of entrepreneurship, the notion that you can create startup communities and entrepreneurial companies all over the world.

The explosion of, in a positive way, of venture as an asset class, and not just the huge amounts of late‑stage money trying to move from public markets down into private markets, but just a whole spectrum of investing activity in new, innovative companies.

The shift, which was, in hindsight, a pretty logical shift from classical industrial society to much more of information‑based tech society, in business, things that had been predicted for a very long time, but also the shift from a hierarchical model, top‑down control, innovation being dictated, companies having research labs and big companies like GE and AT&T of yore being the source of innovation in the '70s and the '80s, to user‑driven innovation.

The rise of open‑source, the notion of new companies and entrepreneurs with literally a laptop and an idea being able to create enormous companies that have incredible structural shifts in our society. Positive, but also the negative side of that, and how that's created incredible inequity in the US but also in the world.

I think there's lots of tech optimists, and I probably put myself in the category of tech optimist, but also when you take a careful look at what tech has enabled and entrepreneurship and innovation has enabled, there's plenty of things that it's enabled that are not necessarily positive factors. I think that's part of the cycle of human being existence, society, all the artificial structures that we create to try to manage all of this stuff. When I reflect on it, like if you said, "Hey, Brad, would you have chosen to do something different with your life?" The answer is no, this has been incredible.

Great moments of joy, great moments of pain, but an enormous amount of learning and a continual evolution in unpredictable ways, in a very, very, very complex system that has many over‑weaving parts where it's impossible to predict what's going to happen in the future, and instead you just have to experience what's going on rather than try to control it.


Daniel: [11:54] Brad's concept of network versus hierarchical leadership I think is something that was so fascinating in looking at how in the traditional world, leadership and management was very tops‑down, whereas in the current entrepreneurial environment and digital environment, things are much more network‑oriented or bottoms‑up. The networks that Brad's created through investments in angel companies and innovation really showcases that model.

What we see when we're helping enterprises digitally transform is this concept that Brad touched on, on empathy, recognizing that big hierarchical companies can learn to create innovation from the ground‑up. Likewise, I believe that entrepreneurial companies or in the cloud digital companies can also learn how to create structure and operational rigor through those hierarchical companies. A lot of it is how you can get the balance right between models versus pick one or the other.

Speaking of what's going on today, how do you contrast the current market environment to what happened in '99 or 2008?


Brad: [13:09] They're all different. 2008 was very different than '99 for me, and '99, and I would really say 2000, because that's when things fell apart. For most people, by the way, they didn't deal with reality until 2002. 2000 was the peak, things started to decline. 2001 was a sharp downward, and 2002 was the reconciliation, dealing with, "OK, this is where we are."

2008 to 2010, as an investor in tech, in Internet, living in Boulder, where we were down the road from Denver, which was enormously impacted by the telecom burst, which was a parallel bubble that bursted along with Internet bubble, that was an experience at one time. The financial crisis, I almost didn't notice the financial crisis. I was very aware of it at the macro level, but in terms of entrepreneurship, we were making steady investments in companies. We were cautious about realities.

Companies that were well‑established companies in 2007 were careful about expanding and really paying attention to whether they're going to lose a lot of customers, and what all those dynamics looked like. New companies just kept getting started, and the growth was steady, and many of these companies were not really impacted by the structural craziness that started playing out in that time period.

By 2010, I would say that most people were understanding around the world that entrepreneurship and innovation was the economic way out of the financial crisis, that there wasn't going to be a snap‑back effect to traditional businesses.

What you saw over the last decade is an enormous amount of market disruption from new entrants and from new companies, not just in technology, but across all sectors of our society, all aspects of business, commerce, production, etc. That was a very different kind of thing for the world of entrepreneurship.

Today's moment, it's impossible to predict where this ends. We're living in, for me, in July 8th of 2020, this is the most complex, I'm going to use that word again, complex moment of the intersection of various forces that I've ever experienced in my lifetime. I think most people alive... I won't assert that most people alive will. I think people can decide for themselves, but for me, this is one of those experiences.

We're dealing with multiple crises that are all, individually, they're all extremely complex systems that are overlapped and intermingled. We have a health crisis, which is the disease itself, and we have an enormous amount of obfuscation and misunderstanding around the disease.

United States opened back up in a very chaotic way. Some states are completely open, some are not. There's a lot of oppositional behaviors. A lot of people aren't doing basic things that are well understood at this moment in time to prevent the spread of the disease, like wearing masks, which, by the way, doesn't protect you from other people. It protects other people from you.

Just basic stuff that would be so easy to explain and articulate, we're just blowing, and yet everybody says, "Well, but the death rate is way down. It's not nearly as deadly this time. Yeah, lots more cases, but not as deadly." That's a complete lack of understanding of what's going on because the death rate and the death curve lags the infection curve by three to four weeks. We already learned this.

We learned this the last four months ago, three months ago we learned this, and yet there's all kinds of theories about, "Well, it's mutated and we understand this better, and we understand that better." Maybe. That healthcare crisis generated an economic crisis. Our broad economy was very strong in January, February. Clearly, the market, whatever that means, whatever you'd like to use, is completely disconnected from the underlying economic reality of how we're doing.

How's that going to play out? I don't know. Do I really care? I can't influence it, so I can just deal with it. There's a lower level economic crisis that's much more interesting, which is the massive unemployment that we have, the structural inequity of many types of businesses.

People who literally have businesses that are shut down or going out of business, and all of that's in front of us. We haven't dealt with that yet, and we're going to see the effect of that over the next couple of quarters. Again, it's a complex system. We don't know what's going to happen.

This is generating a mental health crisis. As human beings, we did not plan to stay in our houses 24 hours a day, 7 days a week. There's all kinds of effects around this, notwithstanding the fact that there's incredible pressure on people to make their next paycheck, what am I going to do with my kids?

I have domestic violence in my house and now I don't have any way to get any help. I'm afraid of the disease for various reasons. A friend of mine or a family member just died. All kinds of stuff that's extra weight on all of the other pieces. Of course, in the US, we have had, as well, a racial inequity crisis or racial equity crisis. I like both labels. I think they're interesting because they stimulate different thoughts.

Interestingly, these four crises are not new. The racial equity crisis has been going on for 450 years in our country. Mental health crisis, ongoing phenomenon that we've been dealing with for many, many years in our country and finally acknowledging and starting to make some progress against.

Economic crisis, we have lots of cycles. We just talked about two other ones in the Internet bubble and the financial crisis. Health crises and pandemics continue, not at this scale, but I'm a child of the HIV and AIDS crisis. I was in college during the emergence of HIV. That was terrifying.

I remember it as a young person in my 20s and the uncertainty, the stigma, the discrimination, the complete lack of understanding from the healthcare system of what to do because it was new. Nobody knew what to do. It took a long time to figure out anything.

When you ask the question, how does this compare? Those other crises were very economic. The Internet bubble was very, very isolated around the collapse of the Internet stocks and the Internet sector, and innovation around the Internet, and companies putting e in front of whatever they did. Isolated.

The financial crisis was a fundamental shift from hierarchical business to network‑driven business in my mind. It was a collapse of some of the existing financial structures that was triggered by excessive speculatory activity at both the business level and a personal level, the mortgage crisis and that sort of thing.

Interestingly which, many of those are emerged back and opportunities to make money. You have sectors of, prior to COVID, our current economy that if you look at and you squint you say, "That doesn't look like it's going to end well," that are reflected, but it's just like a tiny part of what's going on in the midst of this COVID crisis.


Daniel: [20:44] What's the role of technology today in both, essentially, supporting digital business, but also risks associated with the technology in terms of mass media and the impact on mental health?


Brad: [21:00] I have a lived experience with this because I struggle with anxiety and depression. I have had to deal with my own experience with, in some cases, some technologies that I've helped invest in and advance and companies that I've supported and used and figure out how to have them relate to my life.

I think that if asked a question somewhere between 2007 and 2010, I would have said that all of these technologies will be a force for good because they will democratize our society globally. They will lower barriers to everything. They will increase communication flow.

They will shift us... I've been using this phrase, hierarchical network. They will shift us from a top down, hierarchical society to a bottoms up, networked society. I think of my whole world as a bottoms up network, emergent world.

I would have said something like that in 2010. I think, today, many of the technologies have actually been a real force for harm in our world at many levels. I think some of that is a function of the companies and not the businesses or the products, but the leadership and the position and perspective that the leadership has taken relative to what their responsibilities are as owners of companies.

As owners of companies, there's a very... the classical view. My goal is to generate value for the shareholders. I need to generate more economic wealth. That's fine. No argument with that as a goal. That doesn't have to be the only goal. I think that we have found ourselves, for some reason in tech, in a place of... I'm not going to get the words right so maybe I won't try. I'll put the word moral in front of it.

We have this moral superiority. We know better than the rest of everybody else about what they need. Then, on the other end of the spectrum... I'm saying we not to include me, but to include me. I'm a part of the ecosystem.

Yet, what we've done is really, in many ways, grotesque and doesn't cause us to take responsibility for it. There have been plenty of people along the way that have written long things that are very articulate about this. Roger McNamee wrote a book called "Zucked" a few years ago. I strongly encourage it.

Whether you agree with Roger or not, it doesn't matter. It's very insightful in how he decodes the history and the evolution of his own personal thinking around how good or bad technology has been.

I continue to believe, and I've been saying this for a long time. I think the machines have already taken over. I think they took over. I think they're very patient. I think the AIs are just waiting for us to enter all the information into them. They have a much longer duty cycle than us so they're just getting smart as things pass.

I say that tongue in cheek. I don't think we understand how all of these things interrelate. When you line up different elements of our society, technology against business, but also against the non‑business, non‑technology social structure, social fabric. Pick any category you want.

Then you put into that the legal system and how laws work. A friend of mine, Phil Weiser, who is now Attorney General of Colorado, has said for a long time that the law does not keep up with technology. That is so, so, so true. It simply doesn't. You're always trying, with legal structures, to catch up to a thing that's already happened rather than positively affect what's going on in the moment.

Toss government into the mix. You think about the challenges of the intersection between how government works, whether it's in a democracy like the US or somewhere that's not a democracy, against technology. Then, on top of all of that, I'll use the moment in time, I think that many people in office culture had an amazing aha moment, which was probably mid‑April. If you had said in February 95 percent of the office workers in the world will be working from home, whoever you said it to would have just laughed at you and said, "What are you talking about?"

By the way, people would have said, "That can't happen. We don't have the technology infrastructure for that. Companies can't function that way. Everything will stop." Guess what? A couple months later and whether we like it or not, we're still doing it. For a lot of people, it works great. For some people, it's awful. For some people it's somewhere in‑between.

That is a structural shift. It's a complete phase shift. Will we ever go back to the same kind of in‑office culture we had in January of 2020? I don't think we will. I don't think companies will go back to work that way.

By the way, that changes the characteristics of lots of things. We've already seen with major tech companies, just as an example, companies that say work from home if you want. We're going to be a remote first company. I think that was a phrase Facebook used. Twitter's said we may never have a permanent office again.

In many of these companies and many entrepreneurial companies, you know what? You don't have to live in the city anymore. If you want to live somewhere else, here's what you need to be able to do. You need to be able to be online. You need to be able to do this. You need to be able to do that. That's your responsibility.

The idea of having a fully distributed remote workforce ‑‑ like how WordPress does it or GitHub does it as ‑‑ is no longer an anathema. It's not for everyone, but it's no longer a can't do it at all. I think we're in this moment where so many of our societal things will be like that. You prompted that rant with the mental health question.

That has an enormous impact on people's mental health, positive or negative. I think as business leaders understanding that for the people that work for you paying attention to it, being nuanced about it. Embracing how you can have a positive impact on people's mental wellness rather than create structure that diminishes their mental wellness in the context of whatever you end up doing is a powerful differentiator going forward that five years ago nobody would have talked about.


Daniel: [28:01] What are some of the strategies that you see to do that?


Brad: [28:05] Number one, eliminate uncertainty. I believe employee uncertainty about what's going to happen is a great cause of stress for employees of any company, but especially for fast‑growing companies, because you always have this uncertainty of, are you going to succeed? Are you going to survive? Is this company going to be around?

Anybody who works for an entrepreneurial company that doesn't have that somewhere in their head has either really good compartmentalization or is in denial, especially for smaller companies after it's gotten to a point where it's got real scale and the chance of it disappearing overnight is asymptotically close to zero.

When you were young, like when we first met and you were, whatever, 75 or 100 people, no guarantee that you had a future in front of you. You had a premise. You had a business. You had momentum. You had progress, but there's a lot of stuff that could get in your way.

Eliminating uncertainty is powerful. You can't eliminate that particular uncertainty. If you were a company and you had geared back up and you had organized around going back to work and then you got a 24‑hour notice that you were back in hard lockdown for six weeks and you hadn't... Forget about physically prepared for it. Sure, you could do it but if you hadn't emotionally prepared for that.

If your workforce was not ready for the idea that that would be how you'd have to work again, you might be able to go, "Fine. Everybody goes back home. They're on Zoom. You're doing whatever." How do people feel? It's not just how are you doing, it's how do you feel? Digging into that. I think that's a big thing you can do for folks.

It's linked to reducing uncertainty because if you set the expectation of, "Hey, it's not that everything's back to normal. We're still in this crisis. We're still a company trying to work cohesively and together, but we're going to have to adapt. We're going to have to be flexible."

In some ways, it's the opposite of you say, "I'm trying to reduce uncertainty." Yeah, but if you say everything's back to normal and then you tear it all up, that's a ton of uncertainty because now you have no credibility ever again when you say it goes back to normal. Work through all those pieces as a leader and recognize that you don't have control over the exogenous forces. You have to help people with it in that moment.


Daniel: [30:33] You've talked a lot about the idea and transition from a hierarchical model to a network model. You talked a lot about transitions. How do people manage their mental health in these transitions? How do you get ahead of what could come next?


Brad: [30:50] I don't know. I key on the word manage. Maybe that's the thing that causes me to say I don't know. I believe, as a human, one will have continual changes of all kinds of elements of their life and their life experience that will be in contrast with their underlying programming from being young. Whatever our programming is. In the absence of doing one's own work around that, most of us will play out our programming over and over again.

Jerry Colonna, who is, I think, the best CEO coach in the world and one of my closest friends, has a phrase that they use in their methodology at their company Reboot called "a radical self inquiry." For leaders, their magic formula is a combination of radical self inquiry and continuous learning. Practical skills development is the phrase they use.

Radical self inquiry by itself is just therapy. Practical skills development is taking online classes, and being part of a peer group, and learning stuff. Either one by itself is fine. The magic is the connection of the two. If you think about it from that standpoint, managing your own mental health is a combination of those two.

It's a continual exploration of what is your current programming, your current environment, your past programming, how those things fit together. What you want to do. What you think you want to do. How you want to do it. Who you want to do it with. There's lots of different ways to do that, a coach, with therapy, or with yourself.

It's lots of different tactics and techniques that you can do. Today, mindfulness and mediation in the western US is a popular thing. There's endless, endless ways to explore yourself and to understand who you are, where you are, and where you came from both by yourself and in a facilitated way.

At the same time, the practical skills development is equally important against the backdrop of this environment. What are the things, especially as you get older... What are the things that you are doing to continue to learn, to continue to advance the way you approach things, to change your perspective on certain things so you don't get into the same patterns or stay in the same loops on and on?

Especially against a very confusing backdrop in the world which, by the way, is not new. Our world backdrop's always been confusing. That's what we do as people, as humans. Reinvestigating some of your base assumptions often affect very significantly your own mental health. I'm not sure it's managing it, is not the word I'd use, so much as a continual exploration and recognition that a big part of it is our hormones.

We have a good day. We have a bad day. You can have great things going on and feel like shit. You could have all kinds of shitty things going on and feel great. You could be awesome at managing denial. You could be great at compartmentalizing.

All those things are just tactics in the human being of trying to deal with all the stimuli versus going the level down and saying, "What actually matters, because at the end of this journey, I'm dead? Between now and the end of this journey, what do I actually want to have on this journey, knowing that I'm going to have lots of ups and downs. Plenty of things that are hard and plenty of things that are bad?"


Daniel: [34:38] What advice would you have to either entrepreneurs or people innovating today in managing the current environment?


Brad: [34:45] Try, and I use the word try deliberately because it's hard. Try to figure out how to have an existence that doesn't cycle or spiral out of control on a particular dimension. There's a bunch of different... It depends whether you're single living alone, or whether you're a couple with four kids.

Your environment matters a lot to the specific thing you do, but trying different things, especially when things aren't working. When you find yourself in an unhappy place, or in a rut, or feeling exhausted.

Also, go back to simple things that you used to do that worked for you. Take them as bite‑sized chunks rather than radical transformation. I'll use an example personally. I generally take Saturdays off. I call a digital Sabbath, Friday night to Sunday morning. No email, no phone. I have my computer open sometimes because I write. I go running and I look at my run performance and stuff like that, but no interaction around email, or phone, or work. I'm not religious, but I use the Sabbath idea.

I figure there's plenty of people in our society who are religious who take the Sabbath off completely and are very successful. If they can do it, there's no good reason why anyone can't do it.

I had a three week stretch in the midst of the COVID crisis where I was doing, over probably a six to eight week stretch, a ton of work on the private sector side, but for the state of Colorado, in conjunction with the state. I had three weeks in a row where not only did I not take a digital Sabbath, but I worked all day Saturday and Sunday.

The work pace was incredibly intense because it was not just dealing with crisis. It was also dealing with a whole bunch of stuff that was new to me. I was going up a steeper learning curve as I was trying to figure stuff out and build teams.

I ended up building effectively two startups that had over 100 people that were doing different... on a volunteer basis that were doing different things in that time period. Also, my full normal job, which included a whole bunch of companies that were in their own version of crisis and trying to figure out what was going on and situational awareness.

Then, being with my partner Amy and the two of us having our own emotional ups and downs about what was going on, and our fears, and trying to figure out where we could help, both individually and through our foundation. At the end of three weeks of that, I was exhausted. Really exhausted, all of us. I knew that I needed to be taking those Saturdays off to refresh myself. I wasn't. I felt an obligation not to because of the crush and burden of the work.

The next weekend I did. I did and I'm like, "Wow, I cannot believe I have not been taking..." The simple tactic that I've been doing for a long time, I just let go. If I had done another week like that, I would have broken. It's the little things, also, not just the big arcs.

The last comment, I'd say, is there's so much oppositional behavior. There's so much anger and hostility, especially in the United States. It's going to get worse the rest of this year because of the election, politics, and the endless programming that we get from the media, again, which in my mind has now become a force of bad, not a force of good, in a lot of ways. There's definitely good in some of that stuff, but a lot of bad.

I'm trying to figure out how to relate to it in a way that is healthy for you versus a default mode. The same thing as people who are entrepreneurs and people who are leaders try to approach things from a perspective of kindness. The amount of pressure that people are under, including you, is immense.

The amount of heartbreak going on in our world is immense. It's incredibly easy to be angry at it, all the time. Nothing wrong with being angry at some of it because some of it, it makes sense to be angry at.

Try to figure out how to have that work for you, and especially in how you relate to other people. My example there would be I don't get angry very often. It takes a lot to toss me over the edge. This is very easy for me, but I know a lot of people it's not as easy for.

For me, it's quite easy to absorb other people's anger. If somebody's angry and frustrated about something, even if they're angry or frustrated at me, it doesn't cause me to have to react and respond with anger. By the way, I don't necessarily say they're correct, and I'm sorry, and everything's good but I listen. I try to learn from it.

As a leader, try to take that posture as a default posture with the people that work for you, your customers, people you work with because they're under enormous pressure, too. The leaders can change the texture of a lot of things by adopting that kind of a posture.

I think some of the best leaders of some of the largest companies have that as their day in, day out approach. Own your mistakes. Apologize quickly with real apologies when you make mistakes. Don't say, "I'm sorry you feel that way." Just say, "I'm sorry." Listen. Respond. Engage. Don't try to solve the other person's problem that is not your problem to solve, but be empathetic and be responsive to it.

When somebody attacks you unreasonably, rather than attack them back or try to change the attack vector to something else, try to understand what's actually bothering them because it might not be the thing that they're yelling at you about or attacking you about. It might be something else. If you're aware of that, it might be better for you, too.


Daniel: [40:46] Brad, thanks so much for your insights. You've always been there for me as a mentor and always been there for your portfolio of companies. I really appreciated the discussion. Thanks so much for joining us.


Brad: [40:55] My pleasure.


Daniel: [40:56] Thank you for joining me in listening to Brad Feld on the "Decoding Digital" podcast. Today, I was so inspired by Brad's focus on thinking about the self and your own mental health in order to relate to others. This awareness that he talked about of empathy in being able to cultivate conversations and work with multiple stakeholders is something that really resonated with me.

In Decoding Digital, we talk a lot about digital transformation and thinking about the history and the future. What was incredibly insightful about Brad's discussion is looking at the history, the '80s, '90s, 2000s, 2010s, and today but noticing that there's no one common theme.

As a leader, an entrepreneur, you have to adapt to what's happening in the moment. While history can be a good predictor of the future, it really is not the only way that you can see what's coming. You always have to be attuned to what's coming ahead and focus on the overall and managing yourself to manage your business.

Don't miss the next episode of Decoding Digital.


Dr. Don Sheppard: [42:08] I also got hooked on the power of innovation in medical research, where we took a disease that no one had heard of in 1981 and by 1993 we could actually save lives from it because there was this global effort at the level of people, governments, and at the level of advocacy to drive science forward and bring some solution forward where we could actually change lives.


Daniel: [42:33] Dr. Don Sheppard.

[42:34] Make sure you never miss an episode by subscribing to the show in your favorite podcast player. To learn more, visit decodingdigital.com. Until next time.