South Georgia, the internet, and startup-land (and also I launched an early-stage venture fund)
What VC has to do with my dog, my grandpa, and a national monument
TL:DR
Small-town Southern kid discovers the internet, leaves her hometown for engineering school, finds her way into startups, gets some exits, and launches an early-stage venture fund investing in technical founders building technical products. Vermilion invests $250k in pre-seed stage technical founders and $500k in seed stage technical founders building developer, data, infrastructure, security, and anything that helps developers create better products. I love working with early-stage founders while they create something they believe in.
It’s my dream job. I have some amazing investors in Screendoor, Sapphire, GREE, February Capital, and many others who believed in my vision for Vermilion Cliffs Ventures. Thank you Fortune for the interview here.
Introducing Vermilion Cliffs Ventures
Yes. Yet another VC fund launch.
But hear me out. I believe the venture landscape is changing, and with that, the founder landscape is also changing. Yes, an ivy league founder with a strong FAANG background is likely to have a better chance at VC funding or a nice partner role but I’m proof that the country kid that went to (and almost failed out of multiple times) a state school can make it in Silicon Valley. It’s all about grit and that can be found in people from all walks of life. We all deserve to be here, no matter your background.
You could assume most founders and VCs like to build cool products - and make money along the way (who doesn't?). This community, especially the people I work with everyday care deeply about what they are working on. While the origin stories of VCs might often feel "typical", in an effort to show a non-traditional route into startup-land and venture capital, here's my story. Buckle up.
My beginnings
Everyone has a story. My story starts–like many American rags-to-riches tales–in a small farm town in South Georgia. I always felt like I didn’t belong in Hazlehurst, Georgia and thought there was something more out there. But I could never imagine where life would take me.
I’ve never liked the “Oh, she grew up poor and got out” narrative. It does a disservice to my parents, their hard work, and my hometown when describing my childhood. But I suppose it is true. Statistically, yes, the county I grew up in, somehow still named Jeff Davis County, Georgia, was and is one of the poorest counties in the nation. But poor is relative. Relative to people I grew up with, I had more than some and less than others. For Jeff Davis, we were middle class. For the U.S., we were well below the poverty line. Everyone was.
Unless you’re a handful of people in the world, you’re either less well off or more well off than someone else. Poor is relative.
Through no fault of her own, my mom found herself single with a 3-year-old at 24 living in government housing and cutting her teeth as a newly minted southern beautician. She went to hair school while I was a toddler balancing child care and night school. At 4’11” and with big, blonde hair that truly screamed, “the higher the hair the closer to God,” Mom was and has always been a force of nature. Talk about grit and hard work. The woman would stand on her feet all day rolling perms and dealing with the public (the horror) then go help my step-dad pick corn or pull weeds at the farm afterwards. She worked every day from morning to night. She still does. Her yard and gardens are beautiful and belong in Better Homes and Gardens.
I’m her only child and her entire world. No matter my age, my mother acts like I’m still the 5-year-old she was terrified to let out of her sight. To her dismay, it just made me fiercely independent and strong-willed. (She’s since started collecting chihuahuas and forcing her love on them; they’ve also all rebelled.)
When I was five, my mom met and married the man that raised me. We moved into his house. It didn’t have wheels or paper-thin walls with neighbors stomping around upstairs. I had my own bedroom with a queen-sized bed with blue floral sheets that matched the comforter, wallpaper, curtains, and throw pillows. We had a four-wheeler and a fishin’ boat. It was heaven. Poor is relative.
I’ve never known a different father, and for that, I am so lucky. My stepdad worked alongside his two brothers in THE town general store that was started by his father when he retired from the Air Force. For 50 years, my stepdad, two uncles, and grandpa worked from 5 AM to 8 PM, seven days a week, running a store that catered to fishermen, hunters, townspeople, and old men gossiping for hours about where the game wardens were hiding and who killed the biggest deer that day. I learned so much about life. When I get asked, “What’s it like to be a woman in tech?,” I think about growing up amongst a bunch of men gossiping about their farms, deer, and wives and it’s pretty much exactly the same. Listening in on the men-folk yapping is where I feel pretty comfortable.
My entire childhood revolved around running between Mom’s hair salon and “The Store” as it was known by everyone. We lived next door to The Store and to my stepdad’s mom and dad, my grandparents. It was heaven. My grandma would make me and my little cousin incredible southern food, my grandpa would sneak us candy from the store and tell us not to tell our parents, the man that ran the deli counter for 50 years would make me a hot dog, he was basically the fourth brother and my unofficial uncle. I was raised in a community of loving, hard-working, intelligent, and hilarious people. Poor is relative.
Schoolwork was easy for me. The social part was a little less easy. I always hid in the library, playing on the computer. Or I stayed up all night to read books, so I could use the computer in the back of my classroom to take a quiz about the book I’d just read. I was obsessed with the computer. (I’m still obsessed with the computer.) I’d breeze through the reading quiz and play whatever pre-installed MSDOS game was available. I vividly remember our principal rolling the first Macintosh Classic into our lunchroom on one of those plastic carts that all elementary schools seem to have. It was the only one in the school. Obsessed.
I’d search the interconnected library system in Georgia called GALILEO for new books to access while trying to figure out how to use whatever version of the terminal I could get into, “hacking” into parts of the computer that weren’t allowed. I’m sure somewhere between my friends being librarians and trying to read 10 books a day so I got more computer time, it’s no surprise I forged a lifelong affinity for computers and technology. I’m just lucky that it’s now become more than a hobby.
My life in the library was juxtaposed with riding four-wheelers, fishin’, and wearing camouflage to go huntin’ with my stepdad. (For the record, I do eat meat, but I’ve never killed an animal; my stepdad would always put me in a tree stand nearby, and I’d simply read Goosebumps.) Everything he killed, we ate. I’ve watched him skin more deer than I can remember and I still prefer deer meat in my spaghetti to ground beef. Rich folks call it “venison.”
I believe that we are, at our core, who we were when we were kids. For me that was a shy computer nerd that deeply loved the outdoors. I’m still that person.
At 13, my mom scrounged up the money to buy my first PC and we had a 56k dialup installed at my house. AT. MY. HOUSE. I had my very own computer in my room. If you tried calling our house from that moment forward, you’d be greeted by a busy signal.
I’ve been told you can look back at a handful of moments in your life that really matter. This moment mattered. I spent every second that I wasn’t asleep or at school on my computer. I learned to build very bad websites which I still love doing as you can tell by the design of Vermilion.fund. I started to learn more about the world outside of Hazlehurst. I made online friends that were more like me. I learned about colleges. I probably talked to some weird old people in chat rooms posing as teenagers. If we’re currently in the Wild West of AI, the 90s were the Wild West of the internet. It was magic.
At 15, I decided I wanted to go to college early. I took all the required junior- and senior-level classes instead of electives, and, at 16, was allowed to go full-time to the community college 30 minutes away. I drove back and forth three days a week and still kept straight A’s. Community colleges are incredible places. People of all ages and backgrounds are proud to be learning new things, and happy to be there bettering themselves. For me, it was the perfect stepping stone from my small, country town to new people and a larger, still-very-country town.
At 17, I got into Georgia Tech. I wasn’t the biggest nerd in the room anymore. I was one of the cool kids and one of like seven women. In retrospect, I should have majored in Computer Science, but had decided I wanted to be a doctor and went with Biomedical Engineering. The only courses I enjoyed were the CS courses. I am not a doctor. Such is life.
I didn’t realize just how different my childhood was from the people around me until I got to Georgia Tech. My accent was very thick. I didn’t have money for dresses to wear to the events I was invited to, and my family wasn’t college-educated. I didn’t really know how to study. I’d never lived away from my mom. I’d never had alcohol. Jeff Davis was a dry county and my parents didn’t drink. Occasionally we’d drive 7 minutes across the river to Lumber City to get Wild Turkey for my grandma’s hot toddies when someone got the flu. I still remember the bottle hidden in the back of one of her kitchen cabinets waiting for one of her boys to get sick. Hot toddies are amazing.
But I made it work. I failed out a few times because I was homesick. Often, I really just wanted to go home, but I came back. I worked full-time as an intern at Georgia Pacific in IT, while taking a full course load. I was making more money hourly than my parents, living off of student loans while having free tuition from a Hope Scholarship and Pell Grant (the poor kids’ one). I was living large. I got a really good dog from the humane society that I couldn’t afford.
And then I graduated. And I had to figure out the world all over again.
I visited NYC for the first time and, like with computers, immediately fell in love. I decided to move to the city to try and find a job and continue to live off what money I had saved. It didn’t last very long, but NY was enchanting, and I appreciate looking back that I wasn’t afraid to take that big leap. NY was and still is the only place I feel at home–but at the time, no one was hiring biomedical engineers with bad GPAs and a southern accent.
Startup-land
One of my very close friends in college and still to this day applied and got into Y Combinator (twice). He was a super-nerd who kept making little companies and had a popular blog in college. He’s wildly successful, one of the best humans I know, and deserves everything that he has earned in life. He’s an incredible founder. When I describe the types of founders I like to invest in, I think of him.
And like those handful of moments that matter, he convinced me to come to San Francisco and start applying for entry-level jobs at the startups I’d been obsessively keeping up with on Hacker News and TechCrunch.
San Francisco and Silicon Valley felt untouchable. It seemed like some faraway universe that wasn’t really real; it was, and still is, the center of the technological universe that my entire life revolved around. Giant mythical campuses and secret buses taking people to their jobs with FREE FOOD. This was my Disneyworld. Startup-land.
I applied to so many jobs. I applied for roles that weren’t a fit in the hopes that they’d have other open roles that could be an option. (Always do this.) One founder sent a very rude reply saying that I wasn’t qualified; it almost made me pack my suitcase and go back to NY.
I still cringe when I read that email. Be nice in your rejection emails, please. People are trying their best. (I’m sorry if I’ve ever been mean to you in an email.)
Twilio
My first in-person interview was at Twilio. Everyone was quirky, nerdy, and from so many unique backgrounds, just like me.
I was hired the same day. I cried. My first title was Customer Advocate which was a nebulous role within GTM that meant “People are trying to talk to us, so they can pay us money. Figure it out.” My role and title shifted 6-7 times in my two years there, because I’d solve a problem, build a repeatable process, get bored, and solve another problem. It was perfect.
The team was just under 20 people and working in person in a giant loft space at 1st and Folsom. I hid in the corner. Early Twilio was magical. I made some of my closest, lifelong friends during my time there.
Jeff Lawson was and is an amazing CEO and leader. I didn’t realize how lucky I was that the first founder I learned from was one of the very best. He set a high standard for being a customer-obsessed and product-focused team. We were shipping at an incredible pace, listening to our customers across every channel. And we were making money.
I learned Marketing, Sales, DevRel, Customer Support, Operations, Branding, Product Marketing, and under the tutelage of an incredible CMO, Enterprise Marketing. I loved building for developers. I loved standing in booths at events for hours, answering questions about Twilio. I loved staying up all night with the Head of Design re-writing every word of copy on the homepage. I was addicted to “tech”--not the thing, but the way people were building new things. I’d found my people and my professional purpose.
Twilio changed my life and I will forever be grateful to the four people on the interview loop that took a chance on me. I thought I’d work there forever, continuing to morph into whatever new role needed tackling the next day. But life had other plans.
Parse
I met the founders of Parse at a tech drink-up. They realized my background fit with what they were looking for in a Head of Marketing and started pitching me immediately. If you’re a founder, always try to hire the person that says they are unhireable. It could take a week, or it could take a year, but you’d be pretty surprised how many hires are long games. I remember joking that they couldn’t afford me, but in reality, I thought I wasn't ready to leave Twilio.
The next week, I went to the tiny Parse office and presented a 30-60-90 day plan in their single conference room. I spent most of the previous night working on it, and had limited context to go on, but they made me an offer. I still have the slide deck and look back at it sometimes just to remember how green I was. But my superpower was that I was fearless and willing to try anything without any preconceived notions. In early-stage startups, hire the green-but-eager lead.
Parse, like Twilio, was magical. Our CEO, Ilya Sukhar, is one of the smartest and most thoughtful product minds I’ve worked alongside. All of our founders were some of the smartest people I’ve ever encountered. And we had this power team of women in engineering helping to scale a product that was growing faster than we could keep up. We had this wildly talented engineering team out of Google building product and helping scale. And our designer was this incredible French kid, who could make the most beautiful designs for anything we needed at the drop of a hat. Like I said. Magical.
I realized at Parse that my engineers were the key to marketing. Every single engineer at Parse would create content, give talks, build tutorials, and help me scale GTM since I was just a team of one. They’d all rally around every single launch, event, and marketing effort, and understood that everything at a product-focused company is GTM.
We were acquired by Facebook just 10 months after I joined. That’s a different blog post that’s already been written by other teammates. Yet it was another life-altering moment. I paid off my student loans and credit cards. Debt collectors stopped calling. I had some wiggle room in my bank account for the first time in my life.
The Facebook team was very good to us–but the acquisition strategically didn’t make sense for the Facebook product vision and it started to become clear very quickly. But I got my first exit (Twilio wouldn’t go public for a few more years), we traveled the world preaching the gospel of Parse, and I got to see behind the walls of the big FAANG campuses with the free food. I still talk to all of my colleagues (friends) from Parse often.
Eventually, the team started to leave for Google, moved into other teams, or went on to start their own companies. I got transferred out of engineering and into marketing and gave notice soon thereafter. I miss working on the Parse team and if I could do any of my startup journeys over with the same people, with the same outcome, it would be Parse.
What’s interesting about Parse is that it is the smallest exit of my four exits, but it is also the product that developers geek out over most when they find out about my time there. Developers really loved Parse, and I’m proud of the work we all did to make the product excellent and the community so strong.
What’s next? Google? Okay.
After Parse, I didn’t really know what to do next. Some people have their entire lives planned out. I am not one of those people. Google kept calling and they had hired most of my teammates from Parse but I didn’t want to work on Firebase. Great, great product and team, but I was tired of Mobile Backend as a Service. MBaaS, what an acronym.
Google offered me Head of Developer Marketing for Google Maps, and after a few months off, I decided to take it. My one-and-only project was to celebrate the 10-year anniversary of the Google Maps APIs. I bought an old Greyhound bus, painted it green with Google Maps branding, and drove it from Google I/O to Disneyworld with 15 stops along the way. The photos are hysterical. There was a vegan taxidermied raccoon and pink flamingos. It was fun to spend Google money on a brand campaign with made-up metrics as a little vacation from the high intensity of early stage startups.
The stakes were low and it was an easy and fun job. But I really missed the excitement of a startup, the people that work on early stage teams, and the pace of shipping. Also, reporting to someone that I was working harder and smarter than was tough. I’d always worked for brilliant people, not boring white men that failed up.
I texted Ilya and asked if there were any interesting startups he’d seen lately. “You should talk to Sid at GitLab. I just angel invested and they just finished up YC.”
GitLab
Sid Sibrandij is the only CEO I’ve ever met that told me the very first day I met him when he would IPO, how he would do it, that he would build completely remotely, and everything we did would be public. Despite this ludicrous level of conviction, he was not wrong. GitLab is public to maintain control of the product vision, he kept the company fully remote, and it’s one of the marquee brand names in early investors’ portfolios. Fund returner for many; life-changing for me.
I believed in Sid’s way of building. Sid is the perfect example of a CEO with a plan, the unyielding will to succeed, and the ability to build outside of the socially acceptable norms that were popular at that time in Silicon Valley. Fund the founders like Sid!
He hired me as CMO. The following week, I met the entire team in person in Amsterdam for the quarterly team summit. I was the first GTM hire and started building out our early strategy and hiring the team from day 1. We were moving fast and it was working. The community was buzzing and teams were starting to pay us money.
Building out in the open was incredible. Every comment, roadmap, product development - all public. This was my first experience working directly on an open source product (“open core,” if we’re being pedantic) and I loved it. I still love it.
If you’ve never gone through the GitLab Handbook, I highly recommend it. If you're a founder or operator. Or anyone. I still get comments almost daily about the early days of the handbook, how they’d read our marketing strategy, and plans and mirror it at their own companies. I was leveling up my own skills, and pushing growth forward at GitLab at the same time. We were all working our asses off.
I loved the marketing team we hired. We were from all over the world and excellent at our crafts. It was such a gift to work with people from so many different countries and backgrounds all pushing towards a common goal.
GitLab was the first brand I worked on that was chasing a competitor that was winning the market. GitHub has always been, and will always be, one of the most beloved developer brands of our time. At GitLab, we saw an opening to win the enterprise and on-prem markets. And we did. Then we went after the cloud market. Lesson for founders: find your entry point, attack it, then move outwards.
I’d been working side by side with Sid my entire time at GitLab. I was in every board meeting, in every strategy conversation, and he trusted me to help him lead the company. We were growing fast and it was time to raise our Series B.
At Twilio, our investors were around in the early days, at our events. I’d had friendly conversations, but I’d never spent real time with any of them. They are all fantastic and have been helpful in my career along the way, but I was too junior at that time.
At Parse, we were so early, and we were acquired before we really ramped up, so I never spent time with our investors or had exposure to board meetings.
GitLab was very different. I was in the room. I had a seat at the table. Life-changing moment.
I asked Sid if I could join the fundraising meetings, help build the deck, and help us raise the round. I’d never been exposed to venture before, and it was a whole new world. Did he need his feisty CMO in the fundraising meetings? Probably not. Did he let me level up and learn how to fundraise? Absolutely. Lesson: Always ask to be involved in something even if it's out of your comfort zone but you want to level up. Most good leaders will recognize the moment to let you grow, and if possible, support you in that journey.
We pitched every VC in Silicon Valley. We were like a circus act going up and down Sand Hill Road and South Park in San Francisco. Most didn’t believe we could build remotely. Most didn’t believe there was enough market outside of GitHub. And frankly, a lot had already put money into a competitor. But they would still take the meeting.
I loved it. No one really understood technical products and it was obvious. Few were operators. Of all the meetings, I think only one had a female investment partner in the room for the pitch. At the time, it was weird. I got mistaken for Sid’s admin more than once. Another time, an old, stodgy VC wouldn’t stop staring at me even when I wasn’t talking. I could tell they’d not interacted with many women. It was a different time. But was it? So few women founders pitch me, even now. That’s a different blog post.
We raised the round. GitLab was growing like crazy. The stakes were high, but we were hitting targets. And I burned out.
I look back at this moment and wish I’d just taken a month off but instead, I resigned. No story is perfect and every journey has points you wish were different. This is one of those times.
Detour into advisory work
Did I have a plan? No. But all the investors that were deploying capital into technical products had started sending me companies in their portfolio to advise, likely secretly hoping I’d jump ship from GitLab and join their portfolio company.
My network was growing and all of a sudden I had deal-flow without realizing what that meant.. For non-VC people, deal flow is the founders and startups that you have access to for investment, advisory, or awareness. It will make or break your investment career.
I worked with so many great founders working on technical products and I loved it. I started taking stock and in some cases cash to help them build out their GTM strategy. At this point, I still hadn’t experienced a large exit, so I couldn’t afford to angel invest; I didn’t even realize it was accessible to me. That’s also another blog post, but I think more people should, if they can afford it, angel invest in a small portfolio of companies to keep their operating chops strong and get outside of the bubble of their own company. It also builds your network, can generate decent returns if your portfolio is broad enough, and can level up your career. But again, a different blog post. (I think I’m up to 7-8 blog posts to write so at least there’s a content strategy for the next few quarters.)
I thought this was what I’d do for a long time. Advise companies, take stock and cash, and be happy driving my own workload for a while. Plans don’t really work out sometimes.
After six months of advising a handful of companies, a recruiter I had worked with put me in touch with the last remaining GitHub founder still at the company. I wasn’t sure of the context, but after a late Thursday evening multi-hour call, I was more than intrigued.
GitHub
GitHub is, and will continue to be, one of the preeminent developer brands of our generation. If you’re a model, getting the cover of Vogue is probably your ultimate dream. If you’re a nerd that loves leading GTM teams, GitHub was, at the time, my ultimate career goal.
I flew to San Francisco a few days later, interviewed with 10+ people in the most awkward interview setup of all time, and started the next day as a consultant to help re-build a dysfunctional marketing organization. Everyone on the existing GTM team was talented, but had been hired by 3-4 marketing leaders that had since left–and each had different styles and strategies. The team had been re-organized, hired above, subject to strategy shifts, and pushed around for years. It wasn’t working. There was no marketing lead. The marketing leadership meetings had 10-12 people in them, and everyone was just trying to “add value” and do their best. People from that team are still some of my closest friends and many of them are leading teams of their own at category-defining companies. A lot of them are advising my portfolio companies to this day or working full-time at others.
After a week of trying to make sense of the complex history of the team, I accepted a full-time role leading all of GTM for GitHub. I’d always built teams from scratch at the earliest stages of a company. GitHub was very different. There were almost 100 people within the GTM umbrella, and again, all extremely talented, but not all the right fit or in the right roles. This job was not to build, but instead to re-build, which meant firing, restructuring, and re-hiring.
The GitHub board was like a dream team of venture capitalists and I had board exposure and spent time with them often. The world’s best investors from Sequoia, A16z, and Thrive were closely guiding us as we rebuilt and grew the company. It was very high stakes and the CEO-founder had publicly announced he was leaving the company. Our executive team of six world-class leaders, myself included, worked incredibly hard to get everyone in the company rowing in the same direction with goals and targets, an aggressive product roadmap, and a cohesive strategy. It was not easy but I learned so much and pushed myself harder than I’ve ever done before.
I left a week before we announced our Microsoft acquisition as I’d done the job I was hired to do and wasn’t built for big company bureaucracy or another acquisition. I learned a ton, made even more mistakes, and it was one of the hardest phases of my career. I would still do it all over again in a second.
Another shocker: I didn’t have a plan for what was next and I really, really needed some time off. Days later, my dog that I’d gotten years before in college died. Brutal. Lola, you were a really good dog and I love you. Life lesson, get the dog, but it will destroy you when they pass. (I can’t write a blog post on that because I’d cry too much and probably ruin my computer from water damage.)
The Land of Venture Capital
Operating is really fun. I liked working on great teams and building toward a common goal. I loved those early customer calls and seeing developers get excited when they figured out how to fix a bug or got a new feature to work for the first time.
I loved the variety of all the companies that were being sent my way from various investors, and when the VC world heard I had left GitHub and the acquisition news hit, everyone started reaching out. They wanted me to work with their portfolio–and I didn’t realize it at the time, but most were shadow-interviewing me for investment roles. I now realize that everything is an interview in the land of VC (and probably also life).
I wrote my first angel check once I got the GitHub exit. I think the realization that I could angel invest was as simple as their lead investor emailing me and saying “Hey, do you want to angel invest in this company I’m about to back?” Fellow VCs, be more clear in your intentions to people who are new to angel investing and advising. Some of us didn’t grow up in this world and don’t realize that being on a company’s cap table is an option. I invested in Radar, a company based here in NYC, and while I am sure I was very confused during the angel investment legal process, it was a great investment and I’ve learned a lot since then.
If going to college, the big city, Silicon Valley, and startups were out of reach to a country kid from the South, Venture Capital felt like I was trying to get to another planet on a paper airplane.
Funds were starting to realize that operators make good investors and even better partners for founders. Some of the greatest investors come from a finance background, but I tell all of the founders I work with, build a set of investors with different value-adds for your cap table. In technical startups, it was very hard to find an investor with GTM experience at technical companies. It set me apart.
I’d worked with OpenView on advising some of their portfolio companies after meeting them during the GitLab fundraise. I started working with them in a more official capacity as a Venture Partner and we figured out what that meant as we went along. I learned how to manage deal flow, evaluate founders, understand business metrics that could deliver a fund-returning company, manage a portfolio, and win a deal. And I was good at it. I was junior in some ways, but senior in others, and the OpenView team let me be me and gave me a lot of runway to figure out my way in venture.
I worked on three category-defining deals. I took charge of the Buildkite investment, joined the board, and admired the team’s passion and customer obsession. I also collaborated on investments in Axonius, now a multi-billion dollar security company, and Balena, a leading IoT platform. While OpenView focused on Series B, I was drawn to much earlier startups.
I missed the 2-10 people stage with an idea or an MVP of a product. I was an early-stage operator and investor. It made sense. In my entire career, I’d been happiest when the team was small, the product was just getting traction, and our customers were early adopters. It felt like beyond Series A, its repeatability, scaling teams, metric optimization, and HR oversight. Some people love that stage. It’s not my favorite.
Back to my roots
During the early days of the pandemic, I started spending almost all of my time angel investing in pre-seed and seed-stage companies.
GitLab and Twilio had IPO’d and GitHub had been acquired all within a reasonably short period of time. I finally had the capital to start writing checks into founders that I liked at the earliest stages of their companies. I invested in 20 early stage companies and tried to help my founders with anything GTM related that they needed.
I loved what I was working on but I missed nature and exploring so I decided to go ramble for a while out west while working remotely. And I got a new dog who was a little demon at first but is my little demon now. She’s asleep in my lap. She’s been everywhere.
I spent a year exploring Wyoming and Montana; it was too cold in the winter, but the summers were absolutely magical. The first time I’d ever seen snow was at age 24 and someone thought it would be a good idea to strap a snowboard to my feet and throw me down a blue run in Tahoe. I decided to try again and took up skiing in Wyoming but falling hurts way worse when you’re older. I still hate snowboarding and skiing and get tired of the thinly veiled social class question of “Do you ski?” No, I’m a redneck. “Do you go noodling?”
I’d been introduced to the vermilion rocks and national parks around Southern Utah by one of the more important people in my story. My biological paternal grandfather–I have a confusing family tree; it’s fine–is one of my closest friends and favorite people in the world. Texting with your grandparent might seem like a chore, but he started using computers, email, and smartphones well before I did. He also was obsessed with technology and nature. He texted like a millennial. I think having kids at an older age keeps you young, and his two youngest daughters aren’t much older than me. They are the best. I still laugh at some of the emails he sent me 20 years ago and I still have his hilarious voicemails. We are very similar people. He also apparently bought crypto early. I did not.
He traveled the country in a giant motorhome, pulling his off-road jeep with whichever wife he was married to at the time. After my favorite grandmother passed from cancer at a very young age, he used to fly his puddle-jumper plane between various towns where I’m convinced he had girlfriends. He was an only child who inherited the family business, made some mistakes, made some good investments, then retired early and just explored. He lived in Moab for part of the year, Alaska for other times. He’d spend time at his house in Big Pine Key, Florida which he bought in the 70s for like $40. He was all over the place, taking his very modified off-road Jeep up and over almost anything that it could climb–and some things it couldn’t. I have photos of him with it on its side. He was such a character. I am just like him. Attitude and all.
He once trapped me and a friend in the Jeep for nine hours going up and over trails outside of Moab. It was terrifying. He was at least 75 and had this crew of burly old men that followed him around up and down and over mountains and cliffs talking in code words on their CB radios. He loved national parks. He loved Utah. He loved adventure. He knew how to live. And he loved me.
I bought a little house in a remote town in Southern Utah near Bryce National Park, Zion National Park, Grand Staircase-Escalante National Monument, Glen Canyon National Recreation Area, Lake Powell, the North Rim of the Grand Canyon, and the Vermilion Cliffs National Monument, and just enjoyed the incredible natural architecture of that area. I obsessively explored the American Southwest all while taking work calls from places that had to be very confusing for the people I was meeting with. Grandpa would tell me his favorite parks to visit and trails to ride. He loved Bryce Canyon National Park. It was his favorite place on earth. It is my favorite place on earth.
I’d go back to NY and reconnect with my home and friends from time to time, but my plants were all dying, the city was still recovering from the devastation of the pandemic, and my apartment had a leak that had escalated beyond what I wanted to deal with at the time. I don’t think I saw some of my closest friends for quite a while. They still love me. I have good friends.
The dog and I just hid in the desert while I’d work then go explore at every chance possible. I got a Starlink because we’d go so far into the wilderness there’d be zero chance of signal, and I climbed every inch of Zion, Bryce, Escalante, Grand-Staircase, and Vermilion. My stepdad was always saying, “be careful” when I’d tell him what I was up to–but if he knew some of the places I went in my various off-road vehicles, he’d absolutely explode. My mom learned to quit asking. My grandpa always told me when you get to the end of the trail, keep going. It’s one of the last text messages he ever sent me.
In the beginning of 2023, Grandpa passed away after a short illness and a long decline in health that stopped him from being able to get out and explore the places he loved. He texted that he was sick so I’d flown in with the dog from Wyoming. I stayed with him that night and it was just his time. His life was full of adventure and joy and I miss him every day and every time I find a new trail. I have his old Jeep now and I’ve been giving it hell just like he’d want. I wish he was still around to tell me about secret spots to explore, but I have all his old maps and guides and he’s marked them all up enough that there’s a lifetime more of his secret spots. Just the other day, I found one about three hours down a dirt road that takes you to a gorgeous overlook of the Grand Canyon from within the Kaibab National Forest.
If you look up the DNS information for vermilion.fund, I registered it a few days after his funeral. The night in the hospital I stayed with him, I stayed up all night working on what would become Vermilion Cliffs Ventures, because I was too afraid to fall asleep.
Brains cope in weird ways. Apparently, when I’m grieving, I launch my own venture fund. Life sometimes feels like a series of distractions.
Vermilion
I spent the rest of 2023 learning all I could about fundraising, running a venture fund, watching Silicon Valley Bank collapse (whoops), and writing a few small checks that I warehoused into the fund. I reached out to so many people I’d met along the way and asked for guidance and help. Life lesson: Ask for help. People like to help. You can’t do everything alone.
I built my fund model and strategy, and I officially started raising capital from institutions in November 2023 after raising a small amount from friends and people in the tech industry earlier in the year. What a learning curve.
Fundraising for a venture fund is nothing like fundraising for a startup. That is another blog post.
I named the fund after the Vermilion Cliffs National Monument because I love how unexplored and rugged it is, the grit of the sand, and the colors and imagery work great for branding. It’s not the typical fund name but I’m probably not a typical investor. It allows me to blend my love for the outdoors with my obsession with technology.
Also, it’s also an ode to my grandpa, the lifelong explorer.
I held my first institutional capital close in early 2024. For the non-VCs, venture funds have multiple “closes” where new investors–we call them LPs–join in investing in that specific vintage of a fund. In my case, I held three closes with my final close in September 2024. This fund is my first fund, so Fund 1 in a series of what will be many funds. Some LPs participate across multiple funds, and some don’t. So you’re starting pretty fresh for every fundraising cycle. You raise capital every 2-3 years, similar to how a startup raises different rounds. Except in a fund’s case, none of the investments in each fund are interconnected. Again, I had to learn a lot, and will likely always be learning.
Life is always providing new twists and turns. No stories are linear. I think people that present neat cohesive life stories that all fit into a singular narrative are in denial. Even my story has been sanitized for simplicity and purposely left out some of the darker things.
At the same time, as my first institutional close was happening earlier this year, my stepdad was diagnosed with two separate, unrelated types of cancer. Both were very advanced and being the stubborn old southern man that he is, he had been hiding his symptoms. Ask your parents about their health. Force them to go to the doctor for annual check-ups.
He called me on a Friday night. He didn’t want to bother me in the middle of a busy work week because he’d known for a day or two. The next morning, I drove home 14 hours to Hazlehurst with my dog in tow. We went to the first specialist visit in Savannah two hours away, and the doctor was laughably incompetent. This wasn’t how my stepdad’s story was going to end. I’m too stubborn, and so is he.
Life-altering moment. I called Memorial Sloan Kettering back in NYC, told them the very limited information we had from a single scan, and they scheduled him for an appointment in three days. I am forever grateful to the woman that made room in her surgical schedule to see us. She was our in. I immediately drove 14 hours back to NY. He flew up the next day with his devoted younger brother who still hasn’t left his side. Sometimes, I realize being an only child means I won’t have younger siblings to deal with me when I’m older. But it also means I would have had to learn how to share.
He and my uncle spent the next nine months in New York City being treated by the best doctors in the world. Two small-town southern men who had never been away from their mother and hometown for more than a few days were living in THE Upper East Side. Two regular old gossip girls. They were learning an entirely new way of life, during an incredibly stressful time for all of us, but horrible for him. It was a hard time, but I enjoyed having them nearby and watching them laugh at the idiosyncrasies of life in a big city. I got so much joy out of my stepdad wearing camouflage and Carhardt since before I was born, and now it’s among the fashion snobs’ favorite looks this year. Put him on the cover of Vogue.
We make sacrifices for the ones we love. Mine were small compared to the ones he made and is currently making. I didn’t get to explore much out west in 2024 but I’ve rediscovered all the things I love about NYC and how grateful I am for access to the healthcare system here.
We’re down to one cancer instead of two, and hopefully no cancer soon. I’m optimistic. He’s a tough motherfucker, and so am I. I get it honest.
If you emailed me in 2024, I was probably responding from a hospital or doctor’s office. The wifi is actually pretty good and MSK does a great job of making spaces for families to have comfortable places to relax.
If I rescheduled a meeting or seemed out of it, it was because I was at the whim of nine different world-class doctors and there were surprises around every corner.
I’ve learned that everyone is going through something. My LPs, my founders, my peers, my friends - everyone I shared my story with this year - had empathy and could relate in some way. It was helpful to have my work to focus on and my professional and personal support system. Thank you everyone for your kindness and patience. It has meant the world to me.
I achieved so much this year during a time where I think, if I had to imagine for myself, I’d not be able to do anything. I raised my first fund in a time when not many new funds can raise capital, and I’ve invested in 24 pre-seed and seed stage technical founders that are building truly category-defining companies. The LPs that believed in me invested in Vermilion because they know I’m different and see it as an asset.
When I think about what I hope to achieve with my first fund, I want to work with really incredible technical founders who remind me of all the founders I’ve been lucky enough to work alongside in my career. I want to help them build their startups. I want to invest in the Jeff Lawsons, the Ilya Sukhars, and the Sid Sibrandijs. Founders that are customer-obsessed and product-devoted, that love leading teams through the various phases of Startup-land. I want to be the person my founders can come to with questions or advice about GTM, strategy, fundraising, or anything at all. I’ve seen a lot of companies and I’ve helped solve a lot of problems, big and small.
I love having a small, collaborative fund. I set out to raise $10M for my first fund so I could work alongside many of the funds and investors I admire and consider friends. I raised $13.1M so I’d have a bit more room to write bigger checks and invest in a few more great founders.
And I get to focus on the most technical products. Developer tools, data, infrastructure, security (my current favorite), AI, and on and on and on. This is my dream job.
Life
I set out to write a simple blog post launching a venture fund. I think 1/50th of this post talks about the fund. But I think it’s hard to understand how I got to where I am without a fuller view of my story. I also think there are lessons within.
I want people to see that even if things feel out of reach, you shouldn't limit yourself because of preconceived notions you or others may have about how far you’re able to go. We can be our own worst critic. Yes, some people get an easier starting point; that’s okay. But don’t let that stop you from taking the leap, even if it might be a fall. Sometimes people look at me like I was raised by wolves instead of rednecks when they learn about my background. Sometimes I do feel like I came from a different planet. I think we all feel that way.
I’ve been told many times that I can’t call my success “luck” anymore. And logically, I agree, but I think we can help create our own luck. Ultimately, life is just going to happen. I can, however, give credit to all the people that have helped me along the way with advice, friendship, and a chance.
I credit my mother with making me resourceful and an incredibly hard worker. I credit my stepdad with making me tough and determined. I credit my grandpa for making me curious. That combination of personalities influencing a hard-headed, freckle-faced kid leads to someone with a lot of grit.
I’m really still just the nerdy kid that loves computers and the outdoors. I love what I do at Vermilion. I can’t imagine doing anything else and I’m good at it. Thanks to everyone who has believed in me along the way and I look forward to everything we will build together over the next few decades.
When you get to the end of the trail, keep going.
