The Exchanges

Q How do you harness all of those networks and ideas that are either sitting inside of Alexis's head or sitting as numbers on a X account into something actionable for a venture capital firm?

A Software. This is where Alexis and I have found our incredible partnership and our balance. If you distill seven, seven, six to its core ingredients, people and product, and how people and product work together is exactly the foundation for everything that we've built. We've been partners for over a decade now. This is our third rodeo. Him hiring me at Reddit to then eventually supporting my harebrained thesis of giving an HR lady a checkbook. He hired me on as an investing partner at Initialized. When we split that firm and started up seven, seven, six, we finally had an opportunity to build a firm the way we wanted to. The starting first principles were we didn't just want a platform to deploy capital. We wanted an operating system. We wanted to be able to scale the things that should be scaled appropriately with technology so that we could preserve Our energy doing those high leverage things that are people-centric. This is the creative, strategic, empathetic work that we believe adds leverage that could impact the most important part of a company's trajectory in those early days. Every decision that we make at the firm is downstream of one question, which is, how does this help founders win? A big part of that is technology. Alexis has had this idea from the dawn of time of Leveraging software to access those nodes in his network, in spreadsheets, and pull those out. He dev…

AI assessment note: “Software. ... He developed an operating system called Cerebro.”

Q What did you find was special about how Pixar worked?

A I truly fell in love with that company. I fell in love with the people that I worked with. I fell in love with the product we were producing. I fell in love with the creative process. Everyone else felt the same way. There wasn't a single person at that studio who didn't love their job as much as I did and didn't have that shared accountability, trust, and respect across the organization. It didn't matter what role you were in. The passion and drive of the people who worked at the studio was palpable. It didn't just show up in the friendships that were built and the relationships made or the high fives over a job well done in a film review. It showed up in the stories on the screen. When that passion and those stories were translated into the dark theaters across the globe, the business results were undeniable. This was the first time I saw a company intentionally design culture as infrastructure. There were consistent, frequent feedback loops, creative trust, psychological safety. All of it was not because it felt good or because it was the nice thing to do. If anyone has read anything about Steve Jobs or Ed Catmull, they don't lead from that place. It was in service of excellence. Full stop. That's where I learned that intentional cultures yield outsized returns. Time and time again. We were winning in the box office. We were winning at the award shows. More importantly, we w…

AI assessment note: “This was the first time I saw a company intentionally design culture as infrastructure.”

Q What led you to decide to leave a job that you so deeply loved around people that you love so much?

A It's something that I've become good at. Leaving. Because a lot of people don't. That's been deeply transformational for me. I left because I loved it so much. That I wanted everyone else to have the opportunity to love their job as much as I did. That didn't mean vacating a position so someone else could go and experience it in that one place. I wanted to take what I had learned and the way that company worked. I'd had so many jobs at that point in so many different industries, and this one was starkly different, so unique. What if we took some of these things, the magical ways of being really thoughtful about every step in the process, where we put people at the center of every system by design, In service of yielding outsized returns, that triple bottom line where you can have your cake and eat it too, what if we cared about people, the systems that supported them, and we translated that to business results? What I wanted to do was pack up my little backpack with all of that Pixar fairy dust and move into the world of young tech startups. What if we took all of the best of those things and applied them to a really young organization? I spent 10 years That next chapter was a decade of this HR revolution, dragging HR out of the back room into the boardroom, treating human capital as a strategic asset rather than a cost center. My first tech company was a little company called …

AI assessment note: “I left because I loved it so much. That I wanted everyone else”

Q How did that experience lead you from going from an operator to an investor?

A It was a really obvious next chapter for everybody else. It felt like a 90 degree turn, anyone looking outside in. When I knew my cup was full at Reddit, I loved everything about that job. I loved the humans I worked with. I loved what we were able to create online. There was no bit about it that made me disconnect. What I recognized was our business was developing. You gotta have some self-awareness. I know that I'm not a public company girly. I knew that after we were acquired by Disney, and we finally got incepted into that machine. God bless them, but public companies, that's not my place to shine. Reddit was preparing to IPO. That is something I had never led a company through before. I had taken the company to the place best I could to prepare for that, and I knew that it was time to pass the baton and bring in someone who knew how to do that. It was a happy parting. That was the business rationale. My cup is full. If I love it, I have to let it go and let it thrive and have that best possible chance for success. And it did. That team that came after me was stellar. How that translated to investing for me is venture felt so natural. Here's my secret, Ted. Early stage investing is fundamentally about people and systems under conditions of extreme uncertainty and distress. After a decade of operating as an HR executive and Helping companies from inception to hyper growth an…

AI assessment note: “How that translated to investing for me is venture felt so natural.”

Q With your history and beliefs that at some point in time your cup gets filled and it's time to move on, how are you thinking about your trajectory from here after five and a half years at seven, seven, six?

A I feel like I've lived 17 different companies within seven, seven, six in the last five and a half years. I don't know if it's possible for my cup to be filled here. The beauty of founding this firm with someone like Alexis, we're very different leaders. We have very different strengths. That speaks to the strength of our relationship. He has the capacity to see around corners that other people don't even know exist. He understands communities intuitively. He has a wild sense of timing. My strengths are more about reading people's systems, incentives, psychology, empathy, execution under pressure. But we don't try to be the same kind of leader or the same kind of investor. We trust each other to be excellent in very different ways. What makes him a great partner for me specifically is that he does take the things that I value very seriously. The core of that is people. He takes founders. Operators. Athletes. Anyone who comes into his orbit. He treats their work and their ambition with respect. He's willing to back conviction early and stay patient when things take time. Patience is rare in our industry. I think this cup is really big. It can hold a lot of volume. It changes every single day. The amount of shifts and changes and evolutions that we've gone through and what Alexis and I personally have gone through I know this is my life's work. It's going to take on several itera…

AI assessment note: “I don't know if it's possible for my cup to be filled here.”

Q What were some of those early patterns that you drew?

A I got good at reading people, understanding power dynamic, that it didn't always match an org chart. Didn't matter whether I was out picking green beans or if I was booking someone at the PD up in Arcata, there was a cultural framework that was established within not just each of the industries, but within each of those companies or groups of humans coming together to do something that didn't always read in sequential order. I learned how to navigate quickly. Keep your head down, make sure you make good with the right people, make sure that people know your name that you want and don't that you don't. Those things shaped my career arc once I did graduate from undergrad.

AI assessment note: “understanding power dynamic, that it didn't always match an org chart.”

Q You come into the organization, it feels broken. What do you do to get morale moving in the right direction?

A After you listen, you have to find the pattern of what drives people. Every single person at that company when I joined was there for a different reason. Therefore, no one could thread the needle on what would move them as a group. What would move them to change and want to invest in anything new was so fractured. My first strategy was to find that point of alignment. They retired. This was a group of people that didn't have a lot of turnover in that first decade, which was crazy. They all were there for a different reason, except for one, their love of the community. Each one of the employees in those early days, they were Redditors first and foremost, not meaning people that work at Reddit. They were Redditors. They lived online. They cared for their communities, and they felt an alliance, an allegiance, and an accountability to the communities that they were a part of online. What I realized quickly was I had to translate that online experience and what mattered to them online to our offline experience, to our work culture. There were several things that we did that were impactful. I had asked everyone, what do you call yourselves? At Clout, we were the Clout Laws. You have to have an identity. Every community, every group of humans wants to commit to something. Part of that is, how do you identify? None of those employees identified themselves as Reddit employees. That was …

AI assessment note: “My first strategy was to find that point of alignment.”

Q What are some of the experiences you've seen when a founder goes from effectively controlling everything in the business to needing to bring in, say, a leadership team and delegating out different tasks?

A This is one of the harder initial inflection points from a founder development and growth standpoint. Depending on how the business develops, companies will peak and valley at different times. Sometimes with those peaks and valleys, there comes an expansion and a contraction. The crazy part is that a lot of founders think that once they successfully cross the chasm the first time of, oh, that was really hard, but when I finally was able to push that decision-making and that autonomy and that accountability down through the organization, That was hard for me. I made it to the other side. They don't expect to have to do it again, and so they forget that lesson. Oftentimes, there is an expression of expansion and contraction. Sometimes that's in headcount. Physically, you actually are pushed back down into the weeds because your team had to contract. Oftentimes, it's a business need expression of expansion and contraction. Maybe you are needed on this particular thing because revenue is suffering. Something has shifted, something has changed, and what was working before is not going to work now, so you have to come back down into the weeds. How do you then gracefully reintegrate yourself into a system that you expressly have said, I should no longer be a part of this? It's not just that first time that you have to coach founders through this beautiful growth moment or milestone in…

AI assessment note: “This is one of the harder initial inflection points from a founder development”

Q product or service we think will be valuable to our community. One is Oldwell Labs, or OWL. OWL is the very best software I've seen for allocators to find and track managers, and I've seen a lot of them. Trust me, it'll be worth the look. There's a link in the show notes so you can learn more. And here are those closing questions. What is your biggest pet peeve?

A I have two. One is confusing motion for progress. The duck analogy. I hate it when people are just busy and they are operating at low frequency because they aren't able to distill the critical leverage from critical mass. You're doing too much. You're not doing it well. Knock it off. Nine times out of 10, I'm the one who has to clean it up. Sometimes I'm talking about my children when I say that. That's not just work related. The second one is I hate when people accuse me of not being thoughtful. Where they ask questions that insinuate that I have not completely, 1000%, overthought in every single Doctor Strange, 10,000 possible iterations of outcomes and trade-offs, and every single detail of every single event that has ever happened or will ever happen. Super insulting.

AI assessment note: “I have two. One is confusing motion for progress.”

Q advantage. That's why customers call it miraculous, game-changing, and an awakening. If that's not how you would describe your investment management tech, request a demo at ridgeline.ai. And now, back to the show. How do you balance this deep focus on the person, the entrepreneur, with what it is they're doing? Is it a good market to be involved with? Do you have conviction on the theme that they're pursuing?

A If someone is showing up, they've got all of the right signals or signs that we believe is destined to be a great founder, but they show up with an idea that is so wildly off the mark. From our perspective, our limited worldview, it's a do not pass go. There are plenty of people that I've met that I like. You've got the goods, but I'm not going to write a check because they were not barking up the right tree at the right time. You have to be within the Spitting distance of solving a problem that collectively makes sense to the firm. Something else that I really appreciate about how we designed seven, seven, six is that we are generalists. Back when we started this up, there were questions from LPs, sometimes even founders. Why aren't you focused? Why aren't you going to be specialists? This is where I really lean on Alexis's experience. When he was building initialized with those partners, they were generalists Because it was a less formal working group in those early days. They were still a part of YC. They were cutting checks into people that were hanging out at the same watering hole. As a result, you have such a unique variety of companies that move the needle, ranging from Coinbase to Instacart, a handful of others. It was a smaller fund that shaped and crystallized Alexis's philosophy and belief that he would always want to be a generalist investor. That is something that…

AI assessment note: “they show up with an idea that is so wildly off the mark... it's a do not pass go”

Q How have you thought about of the flood of potential things that could come in from your network, how to start distilling both the people and then the ideas or the products, the themes?

A How lucky are we, Ted, to be in this industry today, at this moment in time, with everything that's happening in the world, and everything that is about to unlock, and it is the process of unlocking. I just get so jazzed on the opportunity set that's in front of us. How do we distill it? How do we ensure that we are making the very best decisions? A part of that is that we do lead through ensuring that we have more eyes and ears on things. For example, everyone at the firm is invited to any pitch we take. In the pitch process, because we have Cerebro, we have software, every individual that attends the pitch puts their notes into the system, and because Alexis is the Reddit guy, it's anonymous. You're rating these things. We have our own system of how we break down what we're trying to distill very quickly. These pitches, in the grand scheme of things, you're not spending a ton of time with founders before you have to make this decision of, are we going to deploy capital here? Is this a partnership that we want to support for the next Decade plus. We have systems that are built in to where we're analyzing and passing judgment on both the idea. Is this the right idea at the right time? And is the why there? Also, the people. On our partnership team alone, two of the three of us have deep HR backgrounds. Chris Vanzetta is our third partner. We've developed over the last five and …

AI assessment note: “We have our own system of how we break down what we're trying to distill”

Q From all that HR experience, how do you interview people?

A Part of this is repetition. Alexis has been investing for 20 years. There is an understanding of some of his basic philosophies and principles that he's able to distill quickly to say, is this person open to coaching? How do they take feedback in the moment? How do they articulate themselves? How are they selling? A big part of being a founder is your capacity and your ability to compel people. How are they presenting this? How are they presenting themselves? All of those things matter We index pretty heavily on founder. That's not to say that we don't look at product or product market fit at all in those early conversations. You have to have the right idea or what is a thoughtful idea at the right moment. We're all builders. We're all operators. We understand that a product is going to change 16 ways to Sunday before any liquidity event. What you're betting on is a soft part of the idea on that founder. The more I can build in dialogue that isn't status quo, isn't what every other investor on earth is asking them. I recently seeded a company called StarCloud. The founder is Philip Johnson. When I met Philip, it wasn't in a traditional pitch setting. We were at a conference. Meeting founders at conferences is super rare, but Philip was one of the most interesting people I had met in a very long time. We got seated next to one another at a dinner. We introduced ourselves. I had …

AI assessment note: “The more I can build in dialogue that isn't status quo”

Q What are some of the other characteristics you found of great leaders?

A There are several, and they are different amongst them, specifically as it relates to building a high-performing organization. Something that I tell people a lot is hire when it hurts. Do not hire until you have been doing that job yourself for several months, because one, now you know how to better hire for it because you've done the job. And I'm speaking specifically about early stage when you're building something. Not only does that build that better understanding and articulation of the role that you need to fill, It also breeds sincere empathy for what that person is walking into. You can be a better leader to them, a better support them to get their job done. And then the relief that you will feel and the brain space that it opened allows for and lets in dynamic space for innovation and creativity. Hire when it hurts. It's something that I've done for the last 20 years at every company I've built. Every time I've compromised on it, failure exists. In meaningful ways. Alexis and I do that at our own firm. It's what we tell our founders to do. It breeds so many more positive things than negative. What can I do instead of airdropping in senior executive bozo number 25? My job is to help you learn how to hire really well. If I can help our founders and then subsequently their leadership teams learn how to get really good at hiring, And then really good at firing, my work is …

AI assessment note: “Something that I tell people a lot is hire when it hurts.”

Q What are some of the answers to sticky situations like that?

A This is why I'm not scared of AI creating mass unemployment in that I think that our work as humans is being reshaped. The answer to your question is it's different every single time. Details matter. Nuance matters. Context matters. The players in the game that are involved matter. All of that impacts how you might guide someone through something. In my career, in 20 plus years of supporting humans in an organizational way, my partner was just diagnosed with something terrible, which has come up multiple, multiple times. Fill in the blank. Divorce. Death. All of these things that are very human, that handbooks and HR policy doesn't cover effectively. That really matters. Having those conversations, knowing the individual as intimately as I get to know them by design, We'll change how I support them through something outside of work, but deeply impacts their capacity to show up as a great leader. In some cases, the answer is let's figure out succession. In other cases, it's how do we help bring in support right now to help you be able to focus on your most immediate and most precious need, which is the person you love. How do we keep the business on standby for a moment? At seven, seven, six, we have a program that I'm proud of called our growth and caregiving program. It's my belief that the best founders on earth care about their businesses so much. They're always willing to p…

AI assessment note: “In some cases, the answer is let's figure out succession.”