The Builder Mindset

Roger Ehrenberg
7 min readJan 21, 2024

It’s funny to be sitting here at age 58, fully on my third or fourth career (depending upon whether you’d consider my professional angel investor-phase a “career”), and having those same feelings of “Wow, here we go again!” This is referring to the endless questioning, self-criticism, anxiety and reflection on the challenges and excitement of starting something new. I’ve pretty much internalized the fact that I’m a pathological builder and doer — if I’m not building and doing, in essence, feeling purposeful and useful on the daily, I feel like shit. There is something about taking on a big challenge, and then grinding, iterating, grinding some more, learning, failing, grinding, progressing, and ultimately winning. There is a measure of faith in jumping in to any new endeavor, be it a new job, a new school or starting a new business. While you can control the process, the outcomes are an entirely different story. This is where the self-belief part comes in, and it can be the challenging bit, especially in a very long-timeline business like very early stage venture investing (or ground-up real estate development, which I also participate in to some degree).

Building to the sky

If being a venture investor for almost two decades has taught me anything, it’s that builders writ large deserve empathy and respect. How many people have built stuff that has been relentlessly “up and to the right” from the get go? Nobody I know, including the founders of deca-billion dollar companies that my partners and I seeded. The number and nature of the bumps in the road these companies withstood are legion — maybe someday these founders will write books on their experiences. But from my seat it was completely non-obvious that these founders would ultimately disrupt their spaces as they have. They had the vision for sure. They were all builders at heart and in practice. But there is a gap between that and being successful in the marketplace, both in terms of selling products at scale and on selling other stakeholders on the virtue of their vision, most notably the best talent and great investor-partners. Without succeeding with the last two it is impossible to achieve the ultimate goal of selling a lot of products that change the industry landscape and results in a generational business. This kind of success requires three key characteristics: belief; grit; and ruthless focus on process. A great vision is table stakes. How a builder translates that vision into reality is where the magic lies. And even in the best of cases it is hard as hell.

When I started building at the earliest stages of my career, my mantra at work was “always be learning” and “always be awesome”. As a 21 year old I had no idea where I’d eventually end up, but I figured that if I was learning new things and making my bosses happy that I’d ultimately figure “it” out. What I discovered is that “it” is not solely an area of work but also the people with whom you’re working and learning from. By learning and doing a great job, it enabled me to move into other areas of interest with great people because my bosses didn’t want me to leave the company. Sure, there’s always politics, but ultimately if you make yourself valuable and follow your learning-and-being-awesome process, especially as a young person, I’ve found that one can generally McGuyver oneself into the situation you want. This is what worked for me and set the right tone during my Wall Street career. I worked, learned and made my bosses happy. I met interesting people, learned a lot about what other people did, and navigated to work with great people in new areas of interest. From the time I was an analyst in Asian Corporate Finance as a 21 year old or the head of a $6b trading business as a 36 year old, this approach to career building worked extremely well. As far as I’m concerned, I viewed this part of my career as winning. And it took 15 years to get there.

When I left Wall Street, it wasn’t to become an angel investor. As I noted in my last post, I was very purposeful in colliding with lots of interesting people to develop a view, codify a set of beliefs and to establish a process for learning a ton and becoming an awesome angel investor and partner to founders. These turned out to be five of the most stressful, nerve-wracking, exhilarating years of my life, the result of which was to leverage what I had built (networks, knowledge and track record) as an angel investor into starting a firm. As with my angel career, success was non-obvious. My partners and I invested in pretty unpopular, long shot ideas with mostly first-time founders, and it fully took six years until we were able to share the fruits of our success with our partners and ourselves. Along the way we felt stupid countless times, made lots of mistakes and overcame both naysayers and challenges both in the markets and as a partnership. But we believed in our vision and in each other. We had grit. And we spent a lot of time thinking about and investing in our process — what we were trying to accomplish, how we went about accomplishing it, and how this fit or didn’t fit with our key stakeholders — existing portfolio founders, potential new portfolio founders and our partners. By the time we hit Year 11 our first two funds had done extremely well, not just in terms of portfolio value but in terms of money actually returned to LPs. I felt very proud. And the end of the day it took many years for us to win — but win we did.

Which brings us to today. I personally feel like I’m on a similar journey once again, just with a richer set of experiences, a somewhat bigger bankroll, but with a vision, an enthusiasm and the energy to match the ambition of my previous undertakings. I’m barely two years into this new challenge but I have those same “builder butterflies” that I had when I was 21, 38 and now 58 (when I first pursued this new life in earnest). Am I really on to something? Am I doing this right? Is my timing right? Why am I so lucky to be getting the “opportunities” I’m getting? Am I late? Am I early? Is the market too hard right now or is this “the time?” Can I carve out my space in what I perceive to represent a generational opportunity? Can I truly be awesome in this field where I am a rank newbie and others have been wildly successful for the past decade? It’s like I’m working to earn my stripes yet again, just like I did as a tech VC (which still sounds weird that I was a tech VC — I didn’t really know what a venture capitalist was for most of my life) with the same degree of self-doubt and impostor syndrome. This is not to say I’m not a confident person, but when you put your belief, trust and money into your process in a whole new area, it can feel daunting to be the “outsider” until you’ve made it. I remember being at the edges of tech conferences in the mid-late 2000s, working to meet people and make meaningful connections without the status of being known or having real wins (in tech investing) under my belt. This is sort of where I see myself today: I am not an industry insider, but I am working to penetrate the concentric circles of networks, credibility and respect through hard work, deep engagement and innovative thinking and risk-taking. We’ll see if it works but I feel like a 21 year old trying to prove myself once again, to the market but more importantly to myself.

I woke up to see the Q4 Update from my friends at Equal Ventures (where I am both an LP and good friends with the founders), and a few sentences at the end of their letter struck me as being particularly applicable to how I think about things in business and in life:

Albert Einstein once said compounding is “the eighth wonder of the world…He who understands it, earns it; he who doesn’t, pays it.” Those who know [us] best know that getting to where we are today was not an easy road. Venture should NEVER be an easy business and it certainly won’t be in the years ahead, but it becomes clearer and clearer that we are starting to feel some of the wonders of compounding.

I believe this to be broadly correct. Whether it’s investing in businesses, in relationships or in yourself, there are no shortcuts, no quick hits. Extreme value is built over extended periods of time and where the benefits of compounding really begin to kick in. This is a very un-human characteristic, where it’s easy to be a near-term pleasure seeker but it’s much more difficult to delay gratification and play for long-term benefits. I constantly remind myself of this, along with the fact the the only way I know to deal with the fear and anxiety of not knowing exactly how the future will unfold is to focus one’s building by leveraging process. I’ve done it before. Can I do it again? We’ll see how robust my approach to building really is. I’m confident.



Roger Ehrenberg

partner @ebergcapital. owner @iasportsteam & @marlins. founding partner @iaventures. @thetradedeskinc @Wise. @UMich @Columbia_Biz. family man. wolverine. 〽️