Contrary GP on Talent & Research-Driven Investing

Summary

A live, conversational interview on Grace Gong’s Venture with Grace, with Kyle as the guest walking through his path from film-major-turned-videographer to multi-stage GP at Contrary. The origin story is the through-line: Kyle over-booked himself on wedding and commercial shoots, realized he was a better salesman than videographer, and quietly spun up a creator marketplace (>$10M GMV, though he was too sheepish to call it a “startup”) before selling it — in hindsight, too early. A banker friend told him companies get sold; a venture friend told him that being “a resource for passionate creative people” is basically what VCs do. That sent him to Kickstart Seed Fund in Utah as an EIR/scout, and into a ~10-year career.

The middle of the conversation is a tour of how each firm trained a different investing muscle: TCV taught him to hunt “diamonds in the rough” — efficient, bootstrapped, under-the-radar businesses; Coatue taught “big idea arbitrage” — leaning into themes the market underprices, which is inherently counter-cyclical, anti-hype investing (the best time to buy is years before the hype cycle, not during it); Index Ventures taught relationship-driven, boots-on-the-ground conviction. He tells the self-education story of the Seinfeld calendar — a whiteboard where he “ran at” old data-room deals every single day for six months, took the work to a senior colleague who “took him to school,” and back-filled the banking/consulting training he never had (all while raising a six-month-old).

At the core is Contrary’s ethos, credited to founder Eric Tarczynski: identify exceptional people “one notch earlier than anybody else realizes they’re special,” then support them relentlessly across an entire career via a ladder of “skews” — the campus Venture Partner Program, a talent team, first checks when they found companies, Contrary Research. Kyle stresses they deliberately select people who want to build, not career-track VCs; the firm is small (≈20 full-time, only four investors), underpaid relative to AUM, deeply concentrated (≈10 checks/year), and people-centric — weighting career trajectory and, above all, reference calls.

The most quotable stretch is Kyle’s theory of conviction as a finite resource. Riffing on Warren Buffett’s punch-card (“five investments, whole career”) and inverting the “when you have a hammer everything looks like a nail” adage (a hammer is dangerous because it’s endlessly reusable — a small, concentrated fund limits the “fungibility of your hammer”), he argues the best references come not in words (which are infinite and cheap) but in finite commitments: a reference who is trying to go work for the founder, angel-investing their own capital, or becoming a customer after they left. He cites Anduril — the people who followed Palmer Luckey from VR into defense — as the model. The last third covers Contrary Research as “productizing the first layer” of diligence (40–50% of the work is outside-in, no data room needed), the prepared mind it builds, and a thesis method — two tailwinds true independent of the company, then one paragraph on how the company counter-positions into them (Albert Szent-Györgyi’s “see what everybody has seen, think what nobody has thought”). Frameworks close it out: Marc Andreessen’s onion theory of risk, Stephen Covey’s circles of concern/influence/control, and Kyle’s own note-taking stack — Roam as an “hourly active user,” a new tool called Cubby, and the conviction that writing is the funnel: “I write because I don’t know what I think until I read what I say.”

Transcript

Grace Gong: Hi Kyle, welcome to Venture with Grace.

Kyle Harrison: Yeah, thanks for having me. I’m excited.

Grace Gong: So to give the audience a little background — you started what was basically a talent marketplace when you were in school, landing a lot of business for designers and creatives. Why don’t we dive in on your entrepreneurial journey, and how that shaped you into building Contrary, since it’s kind of similar to the talent-management side too?

Kyle Harrison: Totally. So I went into college as a film major. I wanted to go to Hollywood and make movies — I was obsessed with Quentin Tarantino and Martin Scorsese and Christopher Nolan. To pay the bills, I was doing wedding videos and commercials for random restaurants, whatever I could get my hands on.

Pretty quickly I had too many clients. I couldn’t do all the shoots I’d signed up for, so I started going to friends who also shot video and saying, “Hey, I don’t have time to do this job, but I worked really hard to land it — can I take 5% and you do the rest?” And I realized two things. Number one, I was never that good a videographer. I’m very driven, I can talk about movies till the cows come home, but there are people dramatically more talented than me behind the camera. And number two, I could make quite a bit more money doing what I was good at — sales, convincing people to do videos — and then having other people shoot.

So I basically spun up a creator marketplace. I didn’t know to call it that at the time. I didn’t even know to call it a startup — I was already married, and I was too afraid to call it a “job” because I didn’t want my mother-in-law to judge me. So I always called it a “project,” even when we were doing north of $10 million of GMV. I just didn’t know to call it a startup — I’d never grown up in that world.

I ran that for about four years. Eventually it got too big for me to handle. I talked to two friends, probably in the wrong order. The first was an investment-banking friend, and I said, “I don’t know what to do with a business like this.” He said, “Oh, people usually just sell it.” So I went and sold it, got a nice chunk of change. In retrospect that was so dumb — I had so much room to run, selling it was really stupid. And as soon as I sold it, I had no idea what to do with myself.

So I talked to a second friend who was interested in venture. He asked, “What did you like most about the company you were running?” And I said, “I loved being a resource for these passionate creative people — helping them build their business, websites, marketing, accounting, bookkeeping. I just loved solving problems for those kinds of people.” And he said, “Oh, that’s kind of what venture capitalists do.” I said, “I don’t know what those words mean — I should probably figure that out.” I got introduced to some VCs in Utah where I’d been living, ended up as an EIR and scout for a seed fund there, and just learned venture. That was about ten years ago. Everywhere I’ve been since, there’ve been touch points back to that early experience — but it feels like a different lifetime now.

Grace Gong: You started as a scout at Kickstart Seed Fund, then joined TCV as a growth-stage investor, then Coatue, Index Ventures — a lot of really cool names. And you invested in top companies: Databricks, Snyk, Snowflake. What are some correlations from growth-stage investing that carry over to early stage?

Kyle Harrison: I’ve been very lucky to see dramatically different styles of investing. At TCV, at least when I was there, there was a real mentality of searching for diamonds in the rough — almost private-equity-esque, looking for under-appreciated things. I have this natural respect for people who bootstrapped or built very efficiently. One of our portfolio companies right now — I just joined the board — is several million in revenue with 11 people, and not all full-time. Very efficient, under-the-radar growth. That’s what I got trained on at TCV.

Then at Coatue, it was big-idea arbitrage — trying to identify something where the theme is so much bigger than others give it credit for that you can really lean into the trend. That translates into counter-cyclical, anti-hype investing. AI right now is the clear hype cycle, and that’s typically the worst time to invest in these companies — the best time is several years before. You’re constantly trying to find ideas that, for specific, well-researched reasons, you believe can be bigger than others appreciate, then find the founders building into that. Coatue honed that muscle.

And Index was so relationship-driven — boots on the ground, how much time we’d spent with a founder, whether we could vouch for their character and caliber. Each of those translates into what I do now. I joined Contrary to turn it into a multi-stage firm — we do pre-seed and seed, but also Series A and beyond. Throughout, I’m looking for efficient businesses tackling big, underappreciated ideas, in a way that demonstrates the caliber of the people involved.

Grace Gong: From a personal-development angle — you built a business out of nowhere, sold it, then became a growth-stage investor. What did the self-education journey look like?

Kyle Harrison: When I’d built my business, I only spent a few months in the idea/early phase — where seed investing happens — and three-plus years in the growing, scaling, hiring, business-development “meat.” So even though the seed fund in Utah — those guys are great, I still consider them the godfathers of my career — I didn’t want to do seed at that point, because I’d spent more time with companies that had meat on the bones. That’s why I jumped to TCV. I probably overcorrected; late-stage buyouts and pre-IPO stuff wasn’t where I was destined to stay, and every jump since has moved earlier in the life cycle.

I basically feel like I tricked TCV into hiring me. Most people they hired had done investment banking or consulting; I hadn’t. I convinced them that building a company is sort of like that. It was a steep learning curve — there was stuff the other investors knew that I had no exposure to. So I set up what I call a Seinfeld calendar. You know the Seinfeld bit — as a comedian your job is to write a joke every day, cross it off, and never break the chain. I had a big whiteboard next to my cubicle, and every single day I’d go back into the data rooms we’d saved from previous deals and say, “Today I’m going to pretend I’m running at this deal.” I’d look at the files, try to understand the financials, write out my diligence questions — then take it to the guy I worked with, who’s great, and he’d take me to school: the stupid mistakes I’d made, the retention I’d calculated wrong, the questions I’d missed. For about six months I pretended to run at deals while also sourcing and doing my actual job — back-filling and training myself. It was a really valuable time, and a really difficult one — I also had a six-month-old baby.

Grace Gong: That’s so inspiring — I have a one-year-old, and my energy drains immediately. Now you’re building what I’d consider your own firm. The first time I heard about Contrary was maybe three or four years ago — I was in a venture accelerator and one of my cohort-mates was a Contrary partner at their school. Can you give the backstory on how Contrary branched out to so many schools, and how you build the research effort?

Kyle Harrison: Big credit to Eric Tarczynski, who’s been building the firm for a long time. His original guiding ethos was: “I’ve worked with really smart people, and if I could create a mechanism to bet on the future careers of these sharp people, I’d probably do pretty well.” Over the last five to ten years that’s proven true. Contrary is built on identifying those people one notch earlier than anybody else realizes they’re special, and then supporting them relentlessly throughout their career.

Originally that was the Venture Partner Program — folks on campuses who scout for us and find deals. It’s win-win: they get exposure to startups and to evaluating companies, and it’s a great way for us to get to know them. Some of the smartest people in the Contrary network we met as undergrads. As that network matured, we built out skews that span someone’s whole career: a robust talent team to help them think about where to work and stay close to them; being their first check when they start a company; helping vet a co-founder, find early customers or employees. Five of the first fifty or so employees at Ramp came from the Contrary network.

Research is one of those skews. People in the network would come to us and say, “I have offers at Notion versus Stripe versus a Series A company — how should I think about this like an investor would?” At first Eric, Will and I and the rest of the investing team would just share our perspective ad hoc. But two things: it’s not scalable with several thousand people in the network, and there are only so many companies we can be really smart on. By building a research effort and open-accessing it, we invite feedback and critique, which improves the quality. Everything we do is building skews that provide value to sharp people — from the first time they look at a startup in school to when they build and sell companies. We want to be part of that whole journey.

Grace Gong: It’s super impressive you built a presence at 60-ish schools. I have younger friends who fight to be a Contrary partner. How are these partners selected, and how do you scale to that many schools at once?

Kyle Harrison: Again, a lot of credit to Eric — in the early days he was literally sleeping in his car, driving around the country, getting to know people. When you have no brand, you build it from the ground up. That’s actually how he and I met: I was in Utah, had sold my company, was at a venture fund, and he reached out because he was coming to Utah to start the Venture Partner Program at BYU and wanted help plugging into the entrepreneurial ecosystem. We kept in touch across my other firms until it felt like the right time to join.

Today we have an incredible compounding engine — the referrals are next-level. Great experiences with awesome people, and awesome people attract awesome people. It doesn’t hurt that our brand has grown. In any given year we’ll have 60 or 70 venture partners; it ebbs and flows — we’ve gone from maybe 60 schools to 40 or 45. Over six or seven years we’ve had hundreds and hundreds of venture partners, so you get a lot of reps at identifying sharp folks. One thing that’s helped versus other university programs: we specifically try not to select people who want to be VCs. There are people who’ll do a ton of banking and consulting internships and want venture as their long-term plan. We want people who want to be founders someday — because the whole benefit of the network is identifying people who are going to build things. People on the tried-and-true banking-consulting-PE-venture track rarely start companies. It’s not never, but on average, wanting to build something out of nothing is indicative of a totally different brain chemistry. Even just dreaming of building something makes you a unique person.

Grace Gong: Interesting — I’d have assumed you’d just go to each school’s entrepreneurship center or student club. If I wanted to be a Contrary partner, do I just apply? And for the “dorm-room founders” listening — does Contrary put a tiny check into each founder, and another when they start their second company? What’s the mechanism for staying in touch with that younger community across their careers?

Kyle Harrison: First — people don’t join as venture partners because they’re actively building something. It’s people who say, “Someday I want to start a business.” That’s indicative of someone we want in the network. And it’s not a heavily formalized diligence process where they write a massive investment memo — that would require a particular skill set. Largely, we want to find sharp people, and sharp people enjoy spending time with other sharp people. So it’s about tapping into that network and enabling them to identify interesting businesses.

But the most important thing we do is not the Venture Partner Program — it’s building this multi-faceted, multi-skew mechanism to support people throughout their career. The VPP is one great touch point, but there’s so much more. Even people we don’t meet as venture partners: we have a robust talent effort identifying folks out working and bringing them into the inner network. We do tech-talk events where four, five, six companies do live demos for an audience of 100-plus engineers and product people — a great way to rub shoulders with talented people. Those are so popular we often get six or seven hundred applications for 100 seats. It’s all about bringing more people into our universe and providing skews that are valuable to them.

Grace Gong: That sounds like a lot of operational work. How do you navigate your time between on-the-ground community building and actually turning it into investments? You’ve done well investing in Ramp, Anduril, Replit. How do you meet founders, maintain the relationship, and eventually invest?

Kyle Harrison: It’s important to note how we think about building Contrary as a firm. This is a bit cliché — everybody says “we operate like a startup, we’re lean” — but the partners at Contrary are probably some of the lowest-paid partners in venture. For our AUM — 200-plus million across multiple funds — we’re underpaid, because relative to assets we have about 20 people full-time. Only four of us are on the investing team. Everybody else is a sizable engineering, product and design team building tools to keep track of people and build out the network; an extensive events team putting on over 100 events a year, from small dinners to multi-hundred-person meetups; and the whole research and content effort. So it’s not just me and Eric and Will and Jason pounding the ground and keeping track of people in our inbox. We think of it as multiple departments that do specific things, and the job is making those teams work together.

For prioritization — who we’re meeting, how we build deal opportunities — a lot is based on paying attention to who in our community is building. Someone who was a VP back in the day, whom we helped land a job at a bigger company, is now starting a company — we pay very close attention. Also friends of friends: we take referrals from our network very seriously. So it’s a myriad of ways, but really it’s paying attention to the output of the engine we’ve built.

Grace Gong: Not everyone builds a Ramp on their first try. How do you think about turning the community into deal flow, and what are you looking for — top engineers, charismatic builders, second-time founders, someone with a big social following? What traits, and what does your diligence process look like?

Kyle Harrison: The first thing to note: everything we do is funnel and awareness building — it creates opportunities to engage with people and build affinity. But at some point the rubber meets the road. It’s not “build a community and hand small checks to everybody.” We do very few investments per year — across the whole team, probably about 10 checks a year. We’re very concentrated, constantly trying to build more ownership in our very best companies. So the funnel is critical, but then we stop and evaluate each opportunity on its own merits. It’s not “it came through the funnel, put your stamp on it.”

The process varies by space, background and stage — a pre-seed person with an idea and a deck is a different scorecard than a Series A or B with real business. But in general we’re very people-centric — very focused on the caliber of the person. Number one is quantifying the career and capability a founder has built: previous work, how quickly they’ve been promoted, how many people they’ve managed. And in particular we take reference calls very seriously. Because our network is so extensive, we can often go to people we trust who know the person we’re evaluating and get an honest assessment. Then, like any opportunity, you dive in and become convinced the business can be very large and return the fund.

Grace Gong: I like what you said about reference calls. Who are you going to — the direct manager, a colleague? What answers are you looking for? If it were, say, the Ramp founder, would you call their past bosses and ask, “Is this person a good engineer?”

Kyle Harrison: We talk a lot about quantifying your level of conviction. Because we make so few investments, we push on each other: “What percent of your entire net worth would you put into this company?” How much conviction do you really have — as opposed to “we needed to deploy the fund.” If you had to put your livelihood on the line, would you?

It’s so hard in the early stage — everything looks amazing. There’s the saying, “when you have a hammer, everything looks like a nail.” But that’d be different if hammers only worked once. The reason everything looks like a nail is that hammers are endlessly reusable. If you had one shot, you’d better really believe that’s the nail you want to hammer. Warren Buffett has this great line: imagine I gave you a punch card with five punches — five investments for your whole career, then you wait until you die. That’s your portfolio. Is that the level of conviction you have?

Everybody would do better to think that way. That’s one of the dangers — not necessarily a negative, there are pros and cons — of big funds. I’ve written about this on my blog. When CRV and a few firms say, “We need to shrink our fund size,” one thing they’re doing is limiting the fungibility of their hammer. With a massive fund it’s easy to say “everything looks great, this could be interesting, this could be interesting.” A smaller, more concentrated portfolio forces you to ask how much of your net worth you’d put in — because you only have one net worth.

That’s why I think about references the same way. Words are like a hammer — you can say as many as you want; they’re not finite, they don’t actually cost anything. What you really ask is: does someone’s reference come with a finite commitment on their part? The references I love are when I talk to someone who’s worked directly with a founder, and I ask, “Are you going to go work for them?” and they say, “Yeah, I’m trying,” or “I accepted my offer last week.” You only have one job at one time — that’s finite. If they say “probably not,” that’s not a great reference. Look at Anduril: a lot of people were surprised by Palmer Luckey’s jump from VR to defense — but what’s even more impressive is that people he’d built relationships with, who’d only ever done VR, were willing to make the same jump because they had so much conviction in Palmer. Where you go to work is a finite thing. Same with, “Are you planning to angel-invest in the company?” — that’s finite capital. Or someone who left a company and then made that company their biggest customer — a finite thing; you don’t have an endless number of vendors. In references we look for people giving a reference with something finite, not infinite. Words are infinite — “they’re amazing, I love them.” But would you commit your career, your capital, your political currency internally to make yourself a customer? That’s what moves the needle.

Grace Gong: That could come with a lot of bias too, though. How many people do you have to ask to get the conviction you need? And beyond conviction there’s studying the industry, the unit economics. Want to use a portfolio example?

Kyle Harrison: Sure — we have an investment in a company called Moment. We did the seed, then Andreessen Horowitz came in for the Series A. My partner Will had spent a lot of time building a deep relationship with those guys. When we were working with them, they were on an idea we were candidly not that excited about — interesting, but a few other companies were doing the same thing. We weren’t dramatically compelled by the idea, but we were dramatically compelled by the team — Dylan and Ammer were exceptional. One thought we often have: if people are sharp enough and exploring interesting-enough things, they’ll very often pivot around to find something. At pre-seed and seed, it’s much easier for a company to turn quickly. That’s exactly what they did — they pivoted to building embedded functionality for fixed-income trading, and they’ve done really well. Honestly, given their backgrounds, what they build now is much more in line with them than the original idea.

So at the very early stages you can put a lot of weight on: do we think these people are truly exceptional? As a company progresses it gets harder to turn — a Series A or B has a lot more baggage, and you can’t just say “they’ll figure it out.” The more weight behind it, the more stuck with it you are. That’s one reason Contrary was originally exclusively pre-seed and seed before I joined; now we occasionally invest later-stage, and that’s where my experience comes to bear — I’ve spent more time drilling into unit economics, go-to-market and efficiency. The scorecard changes as the business evolves, but we always put a lot of weight on the quality of the people.

Grace Gong: On the research side — you’ve published deep dives on AI and more. How do you leverage existing research and internet material into a differentiated thesis? When you write a deep dive — say the AI-native company-building piece — what are you trying to understand at the start, and how do you put it together?

Kyle Harrison: First, important to note: we very deliberately built Contrary Research as an engine independent from our diligence. Some firms’ “research” is just a more formalized due-diligence team. We’re not like that. It’s not that we don’t leverage research in diligence, but Contrary Research is built to say: we want to build good research on private companies and put it out into the world. That gives us the prepared mind a lot of folks talk about — context that lets us move very quickly when we need to get up to speed.

On forming a thesis — Michael Dempsey, a partner at Compound in New York, turned me onto a quote from Albert Szent-Györgyi: research is to see what everybody else has seen and to think what nobody has thought. So it’s less about materializing a thesis from whole cloth. You hear different people frame it differently — Chris Dixon talks about the investor trying to predict the future. Personally I’m more in line with Trae Stephens at Founders Fund, who says we’re not trying to predict the future — we’re trying to have deep conviction in people who are, to some extent, predicting the future. It’s about having them convince me. Research isn’t magic; everything is already out there and available. Look at Anduril — we’ll be publishing a lot on it over the next few quarters. Map the history of the defense industry and Silicon Valley, how tech and defense separated and came back together, concepts like mosaic warfare popularized by RAND and the DoD — all of that existed years before Anduril started. Anduril didn’t invent brand-new ideas; those ideas were already seeded in the ecosystem. There are stories from the ’90s and early 2000s of defense-industry people warning we’d fall behind because we weren’t ingesting our data and were making exquisite assets that can’t talk to each other. Research is finding those threads and saying: this is true independent of any one company.

We’ve covered over 300 companies for Contrary Research. Each memo opens with a thesis section — why does this company exist? — roughly three paragraphs. The first two identify two to three tailwinds that are true independent of the company. Even if Anduril didn’t exist, the need for highly contextualized conflict understanding would be true; so would the shift toward lower-cost, higher-volume assets — drones at a couple hundred thousand dollars versus aircraft carriers at billions. The third paragraph is how the company plays into those tailwinds — and often you find they’ve counter-positioned against the status quo. Anduril is the clearest example: diametrically opposed to the traditional defense primes. But that’s true of every massive business — they built in a counterintuitive way, not just to be contrarians kicking against the man, but because they saw the tailwinds and rode them. Our theses aren’t about coming up with something new and never heard of; they’re about seeing everything everyone else sees and understanding how it translates into things not everybody is thinking about. Which is another reason hype cycles are so dangerous — you’re thinking what everybody is thinking.

Grace Gong: I like the macro-first approach — get the big wave first, then dive into each company. When you write these deep dives, I notice you consult experts. How do you understand a really complex subject — say defense, where a regular person doesn’t know how you sell to the government? Do you chat with 20 founders, read a lot of research, subscribe to experts?

Kyle Harrison: There are a couple of very valuable frameworks.

Grace Gong: First — you’re such a student of venture that you can reference all these subjects and remember them. Is it the writing? You have a very popular blog and newsletter. How do you retain the information? Sometimes I listen to something and forget it 20 seconds later.

Kyle Harrison: 100% it’s the writing. I have a tweet pinned to my Twitter profile: I write because I don’t know what I think until I read what I say. A lot of the things I talk about, you can find in my blog — I had to understand them to write about them, and had to react to them. I’d write something and realize, “I actually don’t agree with that.” Now I know what I think, because I’ve written about it.

So, the two frameworks. One is Marc Andreessen’s onion theory of risk — every business is an onion with risks you peel off. There are high-level risks — is this a big market? — and then down and down to very specific things like co-founder working dynamics. The second is Stephen Covey’s circles of concern, influence and control. There are things I control specifically as a business or a person; things I can influence but not control; and things I’m concerned about but have no control over — like the Fed rate, which impacts me but which I can’t move. Every business has broad contextual information, then industry-specific information, then company-specific information, and you unpack each layer to get comfortable with an investment.

The way I describe Contrary Research is productizing the first layer. For any business, there’s probably 40 to 50% of the diligence I’d do that I can do outside-in, without ever talking to the company — I don’t need their data or their deck. I can understand what they do from how they articulate their product on their website, talk to customers, talk to people in the space, look at how the market is described. Our memos take contextual information that’s scattered across 20, 30, 40 sources — a snippet in TechCrunch, a company press release, a YouTube video from 2009 when they were coming out of school — and bring it into one place. First you need a general sense of the broad category. Then there’s industry-specific context — that’s where talking to a lot of companies in a space helps; you learn how they think versus others. At Index I had the pleasure of working on Wiz — credit to Shardul Shah, the great Index partner who led it. Unpacking Wiz versus Lacework, how to think about cloud security more broadly, agentless models, the pros and cons of each approach — understanding how different companies approached it, and how incumbents like Palo Alto Networks approach it today, is a layer deeper and harder to get to. And then there’s company-specific context, which you really can’t get without engaging deeply — the inner circle of the onion — the people, the product, how capable that specific product is. Those layers of concern versus influence versus control are how I think about evaluating a company.

Grace Gong: You should teach a course on how to do research — I love the breakdown from company to industry to macro level. It’s a great checklist. When you have a structure for what you want from the universe, it’s easier to hunt down the information you need. Quickly saying hi to John and Elsma. Let me jump into a one-minute fire round. First question — what does your content diet look like?

Kyle Harrison: Writing is an incredible funnel for my content diet. I’ll save a piece knowing I want to engage with it, but I won’t engage until I’m writing about it. If I’m not writing about it, I’ll never watch it. Packy McCormick wrote a piece called Business is the New Sports — I loved that tagline and knew I wanted to write something similar eventually, so I saved it for nine months and didn’t read it until it was time. My content diet is largely driven by writing — writing forces me to read and watch and listen to a lot of stuff I’d never otherwise find time for.

Grace Gong: How do you know what you want to write about? I know you’re a big note-taking nerd — what tools do you use?

Kyle Harrison: I keep a notebook by me to capture little things when I can’t get to my computer. I’m a huge Roam user — I’ve always described myself as an hourly active user. The networked, interconnected thinking is incredible, and increasingly it’s great for keeping track of past things I’ve connected together. And I’m increasingly using a new tool called Cubby, which is awesome — I can search a topic and it searches across Substack, YouTube, the podcast apps, and helps me find specific insights, then build collections of quotes and content to pull into my writing. Cubby is becoming a really important part of my note-taking and research.

Grace Gong: Who made the biggest impact on your career?

Kyle Harrison: So many people at each point. But probably the most important — maybe this is cheesy — is my dad. I was very risk-averse growing up. Doing videography was never a great financial decision, and I was always nervous I’d never be able to make money — I thought I should just stick to school. My dad was always the one who pushed me to do more things and was inspiring. That was always really important.

Grace Gong: Who would you invite to your dinner party — alive or dead?

Kyle Harrison: I was just thinking about this, because we’ve been going super deep on Anduril. I’ve become, over the last couple of months, a huge fan of Trae Stephens at Founders Fund — I’d love to spend more time with him. I don’t think I ever really appreciated how religious he is, and his willingness to talk about religion has been really impactful for me.

Grace Gong: Last question — where can we find you outside of work?

Kyle Harrison: Twitter is 100% my go-to obsession. Anybody who wants to jam with me, Twitter is the best place.

Grace Gong: Amazing. Kyle, thank you so much for coming on the show.

Kyle Harrison: Thanks — it was awesome to chat with you.

Connections

The firm & its people

• Contrary — the multi-stage firm (Contrary Capital / Contrary Research) Kyle joined to build out Series A-and-beyond investing. Core ethos: identify exceptional people “one notch earlier than anybody else realizes they’re special” and support them relentlessly across their career via a ladder of “skews.”
• Eric Tarczynski — Contrary’s founder; built the firm from the ground up (early on “sleeping in his car, driving around the country”), starting the Venture Partner Program at BYU, where he and Kyle first met.
• Grace Gong — host of Venture with Grace.

Kyle’s path & prior firms

• Kickstart Seed Fund — the Utah seed fund where Kyle started as an EIR/scout (“the godfathers of my career”).
• TCV — growth-stage training in hunting efficient, bootstrapped “diamonds in the rough.”
• Coatue — “big-idea arbitrage” — counter-cyclical, anti-hype investing; buy years before the hype cycle.
• Index Ventures — relationship-driven conviction; where Kyle worked on Wiz under Shardul Shah.
• Seinfeld calendar / Jerry Seinfeld — the “don’t break the chain” method Kyle used to self-train at TCV: “running at” old data-room deals every day for six months.

Portfolio & companies referenced

• Ramp — five of the first ~50 employees came from the Contrary network.
• Anduril — Contrary’s deep research subject; the reference-conviction model (people who followed Palmer Luckey from VR into defense); mosaic warfare as ideas already “seeded in the ecosystem.”
• Moment — Contrary seed, Andreessen Horowitz Series A; founders Dylan & Ammer pivoted from their original idea into embedded fixed-income-trading functionality. Kyle’s illustration of backing exceptional people who “pivot around to find something.”
• Replit · Databricks · Snyk · Snowflake — companies Kyle has invested in across his career.
• Wiz vs. Lacework · Palo Alto Networks — the cloud-security landscape Kyle unpacked at Index (agentless models, incumbent approaches) as an example of “industry-specific” diligence.
• Notion · Stripe — the “where should I go work?” offers network members bring to Contrary, which seeded the research effort.
• CRV — cited on shrinking fund size to “limit the fungibility of your hammer.”

People & thinkers

• Warren Buffett — the punch-card frame: five investments for a whole career, as the bar for conviction.
• Marc Andreessen — the onion theory of risk (peel high-level risks down to the specific inner core).
• Stephen Covey — circles of concern / influence / control, mapped onto broad-contextual → industry → company diligence layers.
• Trae Stephens (Founders Fund) — “we’re not predicting the future, we have conviction in people who are”; Kyle’s dinner-party pick.
• Chris Dixon — the contrasting “investor predicts the future” framing.
• Michael Dempsey (Compound) — turned Kyle onto the Albert Szent-Györgyi research quote.
• Albert Szent-Györgyi — “research is to see what everybody has seen and think what nobody has thought.”
• Packy McCormick — Business is the New Sports, the piece Kyle saved for nine months until it was time to write.
• Shardul Shah — the Index partner who led Wiz.
• Palmer Luckey — Anduril founder; the VR-to-defense jump that drew finite-commitment references.

Concepts & themes

• Talent — the whole model: betting on the future careers of sharp people via campus scouts, a talent team, and first checks.
• Venture Partner Program — Contrary’s campus scout program (peaked at ~60 schools, now ~40–45); deliberately selects would-be founders, not career-track VCs.
• Conviction as a finite resource — Kyle’s central frame: words are infinite and cheap; the references that matter come with a finite commitment (a job accepted, capital angel-invested, becoming a customer). Inverts “when you have a hammer, everything looks like a nail.”
• Prepared mind — the standing context Contrary Research builds so the team can move fast.
• Counter-positioning — great companies build counterintuitively against the status quo — not to be contrarian, but because that’s where the tailwinds point.
• Hype cycle — the worst time to invest; “you’re thinking the things that everybody is thinking, and that’s very dangerous.”
• Writing to think — “I write because I don’t know what I think until I read what I say”; writing as the funnel for reading, watching, and retention.
• Roam · Cubby — Kyle’s note-taking / research stack.