““I do believe in direct feedback and specifically from a good place where you want the person to improve, it is one of the most helpful things you can do for someone.” – Dave Eisenberg

Dave Eisenberg (@Eisenberg) is Founding Partner at Zigg Capital, a venture capital firm investing in real estate and construction technology. Before founding Zigg, Dave spent twelve years as an operator at Bonobos, TellApart, Floored, and CBRE. He started his career at Bain & Company, then moved on to found Red Swan Ventures.

Chapters

  • Daily family time as an important habit
  • Favorite tools including Twitter, Superhuman, and Peloton
  • Dave’s superpowers, inspirations, and favorite books
  • On failure and success

Dave's Favorite Books

Transcript

Daniel Scrivner:

Dave, I'm really excited for this second mini interview. Thank you so much again for the time, for coming on.

Dave Eisenberg:

Sure.

Daniel Scrivner:

So, I'll dive right in. We do this interview for a bunch of reasons, but from my perspective, we've just had an incredible conversation going really deep on what you do. It's also interesting for me to explore, just my sense is, entrepreneurs and investors spend ultimately a lot of time thinking about habits, routine systems, how they can set themselves up for success. I think it's interesting window to give people.

Daniel Scrivner:

So just to start, and you can take this question anywhere, sometimes for people, this makes sense, sometimes it doesn't. But I just love your take on ... As you think about habits, routines, even just what your daily life, are there things that you do regularly that are important to you, that either help you show up as your best self, help you operate at the highest level?

Dave Eisenberg:

I'm interestingly not a creature of habit. There is one habit that I was able to identify that is a daily habit for me. It's the most important thing in my day, which is every day I start with ... We now have three kids, but my two daughters, we get up and we'll do a mix of stuff. We'll do Magna-Tiles, we'll read books. If we're not too loud, we'll play music, something like that. Then every day I try to be home like precisely at 6:00 and then we'll do dinner. We have a routine which I think starts at the beginning and end of the day. There are days like I really wish ... During COVID actually I saw a lot of, the middle of the day, stuff which was an interesting art of how to balance a full work day with being a home.

Dave Eisenberg:

But I think that my main habit is that, while my kids are young at least, just making sure that I've got a few hours in the morning and a few hours before it's too late. I think there's been a lot of work stuff that I've missed as a result of doing that, and it's a conscious trade off and there have been moments where I think I've wanted to go to certain events that just fall in there. But it's a habit that I think keeps me grounded, keeps a really good dynamic between me and my wife, and I think it's the most important daily thing that I do.

Dave Eisenberg:

I think on the weekly and monthly side, it's a little bit harder to identify stuff. I love Peloton, and when the weather is good, I love playing tennis. Those are things that I really try to find their way into my schedule, but it's not a daily thing in the way that dedicated family time is.

Daniel Scrivner:

Yeah. When you say that you're not a creature of habit, I guess my interpretation of that thinking about myself, because I would describe myself there as well too is, something big for me is just, I'm happier if there's openness in the day and I can have some serendipity and do different things. Is that where you're at? Is that where that comes from?

Dave Eisenberg:

I think it also comes from this love of variety. I think my musical taste is extremely eclectic and wide ranging, and yet I don't go super deep on any one or two artists. I think the stuff that I read similarly fiction and nonfiction and so forth. I believe that one of the reasons why I prefer investing to operating is simply every day I meet a whole bunch of new businesses that I've never heard of, and most of them I won't talk too much again, but they fill me with energy and creativity.

Dave Eisenberg:

We've got a portfolio of 30 something companies that each do something wildly different from one another. When I was a CEO of one company, like that's the one thing you're obsessed about every day. And ultimately I think I realized I prefer liking different cuisines rather than doing the same thing every day. I totally understand people who are the complete opposite, but for me, the variety is where I derive my energy from.

Daniel Scrivner:

Yeah, I'm right there with you. On the tool side, and this can be physical, this can be digital, but I think the idea is, are there things that you found, things that have significance for you, things that have really been able to help you? And on the physical side, it could also just be this cool thing that I just enjoy having, I enjoy touching and using, but is there anything on the tool side that's interesting for you that's worth sharing?

Dave Eisenberg:

I love Twitter. I always have. I find that it's a way for me to interact with people that I deeply admire and respect, who I may not know very well. On the tool side, I have really come to appreciate and respect this very premium email app that I use called Superhuman, where I have a few different email addresses. I'm overwhelmed with email and this thing helps keep me sane in terms of filtering, and keeping it all steady. On the digital side, those are probably my go-to, use them all day long. On physical side, I guess I fell in love with Peloton a few years ago and probably do it three to four times a week. I think as both a community, as a functional way to stay in shape is something that I love. Yeah, that's probably it.

Daniel Scrivner:

Moving on. Question I always love asking people is, what is their superpower? I think for you, I don't know, I could take a few guesses just depending on our conversation, but what do you think your superpower has been over time? Or where do you feel like you're just really strong, and where do you need to compliment?

Dave Eisenberg:

So I thought about this a little bit. I think in another life I could have been a very effective executive recruiter. I really enjoy hearing the personal career narrative, the things that people are looking to solve next, or if they're just looking to really deploy the skills that they've already accumulated, like what is a place where they can get placed. I think it's helpful that in venture you do a lot of recruiting. You recruit a lot of executive talent, oftentimes replacing senior management talent or board directors has become a thing now where I'm trying to build a network of underrepresented folks to place on boards.

Dave Eisenberg:

I think that's been something that I really enjoy doing and I get a lot of energy from. I love networking and it's always been something that I think I've not been afraid of and have had, just a positive experience with. I know there are plenty of people who have the opposite for, and there's a ton of things that I'm weak at. But probably a superpower would be understanding how to place people with companies, and then also how to make, perhaps some non-obvious introductions about putting people together where I think there will be a mutual exchange of ideas, where it may not be immediately evident to either one of them why I've done it. But then with a little bit of prodding, there's a spark of something there.

Daniel Scrivner:

Yeah. I love that. On the flip side, what do you struggle with, what have you struggled with and how have you worked on that over time? And just really quickly, I think it'd be interesting to touch on how you went about selecting your co-founder, your partner at Zigg Cap and how you thought about that relationship?

Dave Eisenberg:

I mean, in some sense, it goes back to that first Bain job I had, which just prized this thing that called Zero Defect, which is to say you're so meticulous that there are no errors in your financial model or in your slides or something. I remember getting berated for missing the color palette of a company, and I was just like, "This is not what I'm good at. I'm not good at all this stuff." So I think whether it's attention to detail, sometimes I think it's just organization, something that I'm not great at. My college roommate will like attest to this. I was a mess just physically in terms of leaving stuff around.

Dave Eisenberg:

My wife is a very clean person, and so to make that work, I had to become a lot better. Honestly, it just requires a lot of work for me to pick up after myself, make my bed every morning, do all this stuff that I think I've had to work at. The truth is that my digital life is similarly a little bit scattered and it requires a lot of effort to keep my email inbox from exploding and to keep my calendar structured and so forth. I don't have somebody who helps me with there.

Dave Eisenberg:

So it takes some real time of mind, but I find that it's rewarding when it's clean and when it's organized and when I've done it myself, I know where everything is, and so forth. But I do think it's a weakness that I just continually am trying to be more mindful of how to be a more organized and structured person.

Daniel Scrivner:

I would love to ask about people and figures that you admire, and I guess the specific vein is, I feel like in venture obviously you're in an industry where there is this lore of ... There's just a lot of people that you can look up to, some that are still investing, some that invested previously. Some that led really significant funds and similarly on their entrepreneur side. So I guess just focusing on entrepreneurs and investors, are there any figures there that you've drawn inspiration from, or just really admire?

Dave Eisenberg:

I think reading about the founding of Benchmark and how the original partners there really had, some really unusual points of view, for instance, there was no concept of avito, but there was the concept of antivito where one person could put a deal through. If they had such conviction, they were pounding the table. I thought that's something that I've tried to incorporate into our firm, which I believe to be an incredibly powerful idea that you never want to stop someone, even if they have the odd opinion from doing something they're incredibly passionate about.

Dave Eisenberg:

It's funny, there are so many people that I admire who are just public thinkers. So, whether that's Fred Wilson and his blog over many, many years, or whether it's Andy Ratcliffe and Joel Peterson with their classes at Stanford, or whether it's Marc Andreessen and Ben Horowitz and their writings, Paul Graham, their writing. I'm sure I don't agree with a lot of their political beliefs and otherwise, but I think just the clarity of their public thinking on technology building has just been extraordinary. Outside of entrepreneurs technology, a person I deeply admire is Winston Churchill. I just finished a book called The Splendid and the Vile, which was an extraordinary account of the early years of World War II before America came in, and how he just had this level of moral clarity that I think held the Germans at bay.

Dave Eisenberg:

And as someone whose family was deeply impacted by World War II in a negative way, I think I just have this incredible admiration for that level of heroism and also just belief and courage. Those are just qualities that I'm glad I don't have to practice in a way like that. But I think just remembering that so many other people have done such things that have enabled us to live in the world we live in today is quite helpful for me.

Daniel Scrivner:

Yeah. Absolutely. I've not heard of that book, we'll link it up in the show notes. It sounds great. I guess, similarly on that tangent, do you have favorite books? And this can be in any vein any direction, and those can be things that just have really significance for you, or I know a lot of venture capitalists, a lot of entrepreneurs will pass on books as well too. People they invest [inaudible 01:02:40]

Dave Eisenberg:

This is going to be the ultimate Homer answer, but my wife just spent the last four years writing a book, which came out on Tuesday, which I'm going to plug here, which is called Baby Unplugged. It was an extraordinary effort for our family to figure out how we want to incorporate technology into our young kids' lives. I remember the third day of our oldest daughter's life, I brought home a Smart Sock that I put on her to track her heart rate and oxygen rate. In the middle of her first night at home, the thing lost its wifi connection, started blaring an alarm in the middle of the night. We lost like 10 years of our life when that happened.

Daniel Scrivner:

And hair went all white?

Dave Eisenberg:

Yeah, totally. It started this like process that she really led in a highly self-direct way to figure out what is our household's philosophy on screen time and on educational programming? When they're watching TV, what do we want them to watch? I think she just did such an extraordinary job of researching from first principles, what is the current experts? What do they say about technology? And then where can I just trust my gut because there isn't research there? So I think she put it all into a book. She's also a very funny person. She created a very entertaining book that has a lot of information packed in. Anyone who has young kids or thinking about kids, check it out. It's called Baby Unplugged.

Daniel Scrivner:

Perfect. We will link that as well too, and I'm definitely interested in reading that. Okay. Last two questions. I'm really excited for your answers to these. Do you have a favorite failure?

Dave Eisenberg:

The failure that actually gave me the confidence to leave Bain and go to Bonobos was when I got my very first feedback session. They said, "Look, we're not telling you that you're not on track to be retained or promoted here, but your level of attention to detail is not meeting our bar. And you have these other qualities that we really like, you're nice to people, you're exuberant, you're a good communicator, but you just have to be much more careful in your Excel modeling and in your PowerPoint stuff." It was just this like, "I don't want to, I don't want to be the best at those things. It's not a natural fit for my talents or my lack thereof."

Dave Eisenberg:

So maybe I should do something else, and I don't think if they had given me a growing review, it's totally possible that I just would've stayed there for several years, I would've gone to business. I just would've had a very different life. It was like a kick in the butt for me to say, "Maybe I should go do something else."

Daniel Scrivner:

Similarly on that, and I typically wouldn't ask this question, but I have to ask this one. On that note, you seem very comfortable talking about and being really open with your shortcoming, and you talked about as well working with Andy at Bonobos and how that was a really big influence. Have you always been that way? Has that something you've learned over time? Anything you can share there?

Dave Eisenberg:

I learned all of that from Andy, to be honest, if I look back at my 21, 22 year old self, I was the person who was the opposite. I only wanted to brag and I only wanted to talk about my strengths. I think I was a little bit of a caricature of a person in that way. I remember him sitting me down and he is like, "You're not building any empathy here, you're not growing as a person. By the way, you're not as awesome as these things as you think you are." He just talked to me like that, and it was so shocking, but it was so helpful.

Dave Eisenberg:

It was one of the reasons I remained so loyal to him, I think he recrafted my sense of self, and I think took me as more of a moldable ball of clay. In that way, that learning, I think it has been something that I've tried to deliver to other people. I think it's a mixture of love plus honesty plus compassion to get it right, and I haven't always gotten it right. But I do believe in direct feedback and specifically from a good place where you want the person to improve, it is one of the most helpful things you can do for someone.

Daniel Scrivner:

Yeah. It's such a generous gift when you can do it and you can communicate that in a way that's not charged and comes from this compassionate place. It's very hard skill to develop. Last question, what is your definition of success?

Dave Eisenberg:

I think it is finding ways to live a life that are at the intersection of things that you find really interesting. So you enjoy doing the way that you're spending your hours with things that you're very talented at, or maybe even uniquely so. Then things that allow you to live the type of life that you want to lead. If you want that to be a very expensive life like living in an expensive city, in an expensive place, you have to factor that in as optimization. There's a lot of people who don't want for that. I say more power to them.

Dave Eisenberg:

The less you need, I think the happier you can be, but there's no recipe for success that is universal. I think everybody's on their own journey to find the overlap of that Venn diagram. For me, most of my career was operating in an adjacent place to where I ultimately wanted to be. So, I think having patience to figure it out is right, but also maybe not being afraid to take some risky things.

Dave Eisenberg:

For me, jumping from a traditional career path into a highly untraditional one, that was the right time in my life to take that risk. I had no meaningful liabilities at the time. It was just a time, and I was lucky that it paid off. But I think creating space in your life where you can take some risk in case you want to do something that is not a sure path, is something that might lead to success.

Daniel Scrivner:

Any advice for someone that is at that intersection right now, where they see something that's exciting, they want to take that leap, but they're may be having a hard time mustering the courage? Any advice you'd give them?

Dave Eisenberg:

Yeah. I would say, go seek out people who may have a similar life background to yourself, who did it and then landed in the place where they did ... See if there's anything that you can take away from studying the choices that they made or the way in which they did it, that will give you that extra boost of confidence. I think a lot of what I've done in my life has been from watching other people and then trying to mirror that in my own life. I think everybody can find someone for whom they're inspired by, and ultimately that might be the thing that pushes you into that decision.

Daniel Scrivner:

Thank you so much for the time. This has been one of my favorite conversations. Appreciate it, Dave.

Dave Eisenberg:

Great. Thank you. I really appreciate it.