Jessica Retrum

Kyle Harrison

Eric Tarczynski

Contrary HQ

Jason Chen

Will Robbins

For the past two years, we’ve run programs focused on identifying and supporting ambitious builders before their startups even exist.

The feedback - both internal and external to our community - was overwhelmingly positive. We received thousands of applications and backed several startups including Zepto, now the fastest growing startup in India.

Zepto CEO Aadit Palicha said, “When my co-founder and I were still finding our bearings, Contrary kickstarted our entrepreneurial journey by writing the first cheque.” Just 2 years later, they’ve raised hundreds of millions of dollars and hired over a thousand teammates.

So this year, we’re excited to launch Contrary Sabbatical, a program designed to help you quit your job or drop out of school to build an iconic startup of your own. 

And we’re upping the stakes - investing up to $250,000 in up to 5 founders who choose to forge their own path.

### The Details

Anyone can apply. Tech employees: quit your job. Students: take a break from school. The only requirement is that you commit to spending a full year with pure focus on your company.

We will support Sabbatical founders like any other portfolio company: with connections to operators who have scaled companies from zero to thousands of employees, a diverse network of potential hires, and tactical advice from our team.

We have no industry or geographic preferences, including international founders. Many of our portfolio companies were started by immigrants, and we don’t want physical location to get in the way of a startup.

We’ll invest in companies through a standard SAFE (no discount, no MFN clauses), on a generous valuation depending on your level of progress (e.g number of users, technical milestones achieved, etc.).

**Teams can apply by filling out the application [here](https://applications.contrary.com/).**

All applications are due by 8/31, and will be considered on a rolling basis. If you need to make a decision imminently, please also note that in your application, and we’ll fast-track it.

If you have any other questions, don't hesitate to reach out at [sabbatical@contrary.com](mailto:sabbatical@contrary.com).

Take a year off from school or work. Get up to $250,000 to start a company of your own.

Contrary Sabbatical 2022

Going against the grain is in Contrary’s DNA. From our radical focus on people to having nearly as many engineers as investors on the team, we think constantly about what the best venture firms in the world look like a decade from now – and how they’ll win.

One of those defining beliefs is that venture firms who don’t operate like startups – i.e., having world-class products and technology at their core – won’t be around in a decade.

We’ve spent the past several months scouring the country for the right person to spearhead those efforts – helping Contrary build the most sophisticated tech and product stack in existence.

Jen Yang-Wong is that person, and we’re thrilled to welcome her to the team as our Director of Product.

One of the constants throughout the process was just how well-respected she is by colleagues old and new. She brings a level of tenacity and execution to Contrary that’s unmatched, and the results are showing already.

Prior to joining, Jen was in senior product roles at Novi and Uber Eats, and has a proven track record of both the 0 to 1 and 1 to N, helping build startups from scratch while also managing multi-billion-dollar M&A, like Uber’s purchase of Cornershop and sale of Uber Eats India to Zomato.

On the side, she’s built an impressive angel portfolio focused on backing exceptional founders, and is an active advisor to many.

We're thrilled to announce that Jen has joined our team to lead Product.

Welcoming Jen Yang-Wong

Supporting people rather than companies is the core of what we do at Contrary. That's why we've worked hard over the past five years to build the infrastructure needed to identify exceptional individuals and build deep, long-term relationships with them years before they start companies.

A key component of this approach is connecting up-and-coming builders with high-growth startups. This is not only helpful to the startups that recruit from the Contrary network, but hopefully life-changing for those who embark on the journey most aligned with their goals.

That's why today, we're excited to announce that Anthony Nardini has joined Contrary as Head of Talent!

Anthony spent a decade in leadership roles at Goldman Sachs, but found himself with the itch to start a company of his own, specifically around guiding people through their own professional journeys.

So after building a career-coaching startup, he joined On Deck to launch the First 50 Fellowship and then ran their Hiring business as they scaled from less than 20 people to over 200.

Having spent quite literally years looking for someone so thoughtful about talent in the startup world, we can't wait to share more about everything Anthony will be leading at Contrary. More importantly, as many of you will soon see for yourselves, I'd have a tough time imagining somebody more kind and genuine taking the helm. (That's not to mention the fact that Anthony's a fellow New Jersey native!)

The ecosystem we've built at Contrary — stepping up to bat and helping people while asking little in return — is the most long-term-minded approach in existence. Talent is the core piece of that puzzle, which is why I'm so excited to welcome Anthony to the Contrary team.

We're thrilled to announce that Anthony has joined our team as Head of talent.

Welcoming Anthony Nardini

Today, we’re excited to announce our investment in Uprise, building the wealth management platform for everyone. Jess and Chris have extensive experience across consumer fintech and money management, having built highly relevant products at Wise, Earnin, Robinhood, and Justworks. We don’t think there’s a better team to build the next generation of personal finance software.

This investment is particularly special for me, as Jess is my older sister. Growing up, our mom spent over 20 years as a financial analyst at the Federal Deposit Insurance Corporation (FDIC). Every day, she would assess the various risk factors of banks and other financial institutions, and on rare occasions, she would be dispatched to shut down troubled banks and provide support to its panicked customers. Jess and I had a front-row seat to the importance of making smart personal financial decisions, primarily because we’ve seen what happens when things go awry.

These past few weeks and months have put this in sharp relief. Inflation is at a 40-year high, the Fed just raised its benchmark rate by 0.75 points (the largest such increase since 1994), and a recession may be just around the corner. Lightly regulated crypto companies that promised high yields and safe harbors have paused deposit withdrawals and are flirting with bankruptcy. This downturn is coupled with the continued popularity of consumer fintech that provides retail investors with newfound access to a wide variety of alternative assets.

All of this makes today’s personal finance decisions more difficult and complex. And in a down economy, mistakes are amplified. Well-compensated financial advisors help their clients navigate this environment, but their services are traditionally reserved for people with $5M in net worth or more.

Uprise aims to break down that barrier, starting with recent graduates and those a few years out of college. This generation has never had access to meaningful wealth management support and are now encountering their very first bear market. For them, Uprise is coming at just the right time.

At Contrary, we serve a similar profile across our various communities. We’ve had the privilege of seeing our Fellows, VPs, and alums become enthusiastic early users. They’ve referred friends and colleagues, provided valuable product feedback, and helped the team iterate. Most important, they have made smart and savvy financial decisions with their hard-earned money, confidently navigating an uncertain economy by leveraging advice I wish I had when I was younger.

We couldn’t be more proud to partner with Jess, Chris, and the whole Uprise team as they continue on this critical mission to expand wealth management to everyone.

Investing in Uprise

Data has driven change across industries, but data can only be as impactful as it is transparent. No dataset that businesses rely on has been less accessible or transparent than compensation data. 

Today, if you want to understand the market for compensation you have to rely on a mind-numbing network of spreadsheets and consultants. Matt and the Pave team are tackling that process head on. They're offering a better way to understand compensation and how to make sure your salary is competitive and equitable. 

The Contrary team has known Matt since before his early days at Facebook. My focus in joining Contrary is to drive later stage investments into companies that are perfectly aligned with Contrary's vision of identifying the very best people and supporting them throughout their careers. As a budding talent vortex Pave was a perfect fit. 

As we've continued to spend time working with the Pave team it's become clear that they're clearly focused on becoming a critical data tool for any company to add transparency to their compensation process.

We couldn't be more excited to back Matt and the team as they break down barriers to data-driven compensation planning. 


Investing in Pave

We met Jake Hillard and Rebecca Wong 4 years ago when they shared with us an ambitious vision: building a new approach to 3D Vision that makes sensing 100x more powerful.

This is no easy task: companies have spent billions of dollars over the past five years building large teams to push the boundaries of computer vision. "Hardware is hard" as the saying goes. But Jake and Rebecca are both persistent and brilliant. They literally invented mathematical theory and signal processing techniques that previously didn't exist, and spent years perfecting the technology.

This became Red Leader, and the results are revolutionary.

The story of Red Leader has been one of stealthy grit until now. I'll never forget how the specific configuration of cloud formations on a dreary day in Palo Alto was the deciding factor as to whether or not an early Red Leader demo unit worked properly. But with time, the hardware and software were ironed out, top executives from world-class companies joined Red Leader, and the product became ready to market.

The Red Leader difference can look like the difference between having your eyes open and closed. Look at this example -- one the current industry standard, and one using Red Leader -- moving down a street:

There's nothing else like it in the world. With this degree of 3D perception, problems such as autonomous driving will become far easier and safer. 

Jake and Rebecca are wonderful humans, stunningly smart, and their tech speaks for itself. This is why we're so excited to finally announce our pre-seed investment in Red Leader and publicly share that they have raised a $10M Series A.

Investing in Red Leader

I’m excited to share that Ryan Ma has joined from Stripe as our very first designer. I first met Ryan 10 years ago as classmates at Northeastern and distinctly remember thinking that he was exceptional — sharp, creative, hardworking and kind. Those characteristics continue to ring true today.

When it came time to bring on our first in-house designer, Ryan was the obvious choice and my first call. He brings with him world-class design experience from Stripe, Facebook and Lyft. In addition, we’re deeply aligned on Contrary’s people-first vision and team culture. We’re excited to see many of our internal and external initiatives come to life under Ryan’s design leadership.

We're thrilled to announce that Ryan Ma has joined our team to lead design.

Welcoming Ryan Ma

We've been living in a world devoid of human-to-human depth in the professional world for the past 20 years. Glassdoor and LinkedIn have been standard bearers of this era, which doesn't exactly set a high bar.

Kelsey and the team are reinventing this with Candor, building a humanity-filled product for people who care about knowing their colleagues on a personal level, all while improving themselves as teammates.

As with all things at Contrary, it comes back to the people. Kelsey’s a star who’s spent the bulk of the past five years deep in the operations and growth weeds of fast-growing startups like Vanta.

The more we spent time with her and witnessed her ability to execute, the more inspired we were. And when the opportunity to partner came along, it was an easy decision.

The future of work is going to look a lot like Candor, and we’re excited to back Kelsey and the team as they lead the way for the next generation.

Investing in Candor

I met Kyle Harrison 26 days after starting Contrary.

As with most of the early days, it was a matter of hustle and luck. I’d cold emailed him, wanting to build my network in Utah and BYU.

But unlike most cold emails, this one worked.

I’ll never forget how selfless Kyle was during our first conversation. He had no reason to help me – I was a nobody, and he surely wasn’t going to get anything out of this bargain.

And yet he went out of his way to help, introducing me to people like John Koelliker (whose company, Leland, we backed five years later) and the team at Album VC, among a dozen others.

We became fast friends and stayed close, with Kyle becoming an early advisor to Contrary six years ago.

And while our paths diverged for a few years, with me crisscrossing the country and Kyle doing true late-stage growth investing at TCV, a year and a half ago we went on a walk in San Francisco. While catching up on life, the conversation (inevitably) steered itself back to work, the future of venture, and what we both wanted out of our careers.

We believed deeply that venture was changing – fast – and that an opportunity existed to build one of the best venture firms of our generation.

It would be focused on identifying the brightest people in the world – first – and building infrastructure to relentlessly support those people for their entire careers.

Given Kyle had spent the better part of seven years across Index, Coatue, and TCV focused on working with founders later in their journeys, he’d play an integral role in building out this infrastructure.

A year and a half of sales efforts later (and with massive thanks to his wife Camden and children Dax, Jed, and Eve), I’m thrilled to share that Kyle Harrison has joined Contrary as a General Partner to co-found our later-stage practice.

There couldn’t be a better person at the helm. Welcome, Kyle!

We're thrilled to announce that Kyle has joined our investing team as General Partner.

Welcoming Kyle Harrison

Seven months ago, we led Leland’s pre-seed. Today, we are thrilled to share that we’ve doubled down and have led Leland’s seed, alongside friends like FJ Labs, Goodwater Capital, and strategic angels.

At its core, Leland is a bet on the belief in human potential. That with the right expertise and opportunities, anyone is capable of achieving their most ambitious goals. 

In the last nine months, young professionals have purchased over 2,500 hours of coaching on Leland, and coach orders have grown 90% every quarter since launching. Thousands of people on Leland are now reaching their goals—breaking into the best schools and companies in the world.

Best of all, we believe deeply in the team that John continues to build, and their execution over the past seven months has been nothing short of remarkable.

So if you’re looking for help with any career or educational goal, sign up for Leland.

And if you have a skill you’d like to share (and monetize), apply to be a coach.

Doubling Down on Leland

Today, we're excited to share that Megan Kao has joined the investment team.

The Contrary community is a collection of the world's most ambitious and curious people building across categories. When someone joins our investment team, we look for the same level of curiosity and drive -- and Megan is no exception. She's a perfect cultural fit with the ambitions we have for Contrary.

Prior to joining us, Megan was on the finance and strategy team at DoorDash, and spent several years at Goldman Sachs working with companies like Tesla, Uber, and Nvidia.

We're thrilled to announce that Megan has joined our investing team.

Welcoming Megan Kao

We’re excited to share that Nathan Chiu has joined us as a Software Engineer. Over the past few months, we’ve had conversations with multiple engineers. It was clear that Nathan was head-and-shoulders above the crowd — product-minded, experienced in building from zero to one, and most importantly a great cultural fit. We can’t wait to accelerate our engineering efforts with Nathan leading the effort on product engineering.

Prior to joining Contrary, Nathan was an early engineer at Stytch and a former engineer at Carta. He studied mathematics and economics at UT Austin and grew up in Dallas.

We're thrilled to announce that Nathan has joined our team as a software engineer.

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