How We Raised Our Series A: On Deck’s Full Investor Memo

Learn the playbook and pragmatic tactics for early-stage fundraising from Mike Wilner, a startup founder, advisor, and author of Oversubscribed, a book on seed fundraising.

 min read
Last Updated: 
July 5,2021
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A Tactical Guide to Seed Fundraising

Learn the playbook and pragmatic tactics for early-stage fundraising from Mike Wilner, a startup founder, advisor, and author of Oversubscribed, a book on seed fundraising.

 min read
Last Updated: 
July 5,2021
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"On Deck is on a mission to build a modern education institution for the future of work. 

Today, On Deck has become the place top talent and ambitious builders go to accelerate their ideas and careers, empowered by a world-class community of their peers. 

An education business with software margins: On Deck turned a $763k net profit on $2.71M revenue in 2020, and entered 2021 on a ~$20M run rate. Our defensible advantage and pricing power draw from unprecedented customer love and advocacy, low cost to acquire and serve customers, and the unique interaction of our various community "flywheels" — explored in detail below.

With term sheets from two of the world's top four VC firms, we raised our  $20M series A round led by Founders Fund in March 2021 to extend and reinforce our market leadership, rapidly scale our product and engineering teams, and give our community the opportunity to participate in the value they've helped to create."

— David, Erik, and the On Deck team.


  • Executive Summary
  • The On Deck Journey || Where we came from
  • The On Deck Flywheels || Our strategy and approach
  • The On Deck Product || Come for the community, stay for the “Market Network”
  • The Macro Backdrop || Why now?
  • Team || Who we are
  • Appendices || Additional Resources

Executive Summary

In short, On Deck is “Stanford for the internet.”

A university is far more than its curricula. People discover what and whom they love, develop the skills and EQ to build a career, and make the most meaningful professional and personal relationships of their lives.

Why does that stop at the arbitrary age of twenty-two?

On Deck is building a "modern education institution" where top technology talent and ambitious builders go to start or join a company, develop new skills, build relationships and accelerate through the "step functions" of their careers — a campus for lifelong learning.

Specifically, we are building two things:

  • a new approach to continuous online education: delivered through synchronous 'cohorts' of 100 - 200 individuals, with an emphasis on peer-to-peer learning. In 2021, we will launch up to 120 of these cohorts across ~30 subsets, driving substantial upfront cash flow.
  • a private, professional social network and platform. Serving as the "campus" to our "college," the On Deck product is a “market network facilitating matching between talent and opportunity, knowledge, and more. Think: private LinkedIn/AngelList meets Quora — with potential to be as impactful as any of them.
What Twitter did for media, On Deck will do for online education.

When thinking about the future, it's easy to extrapolate existing business models onto new technologies, but very hard to predict emergent behavior.

When the internet first came along, we created PDFs of newspapers online and said, "This will change everything!"

But it didn't. That was Twitter — the experimentations of an online community led to the emergence of a new peer-to-peer medium, native to the internet.

Similarly, the first generation of "ed-tech" (MOOCs, etc) failed to live up to the hype. Learning from their shortcomings, On Deck "re-bundles" community with curriculum. We build the tools and culture that makes peer to peer education rewarding and personal.

What emerged is a place for continuing education and socialization for every curious human with an IP address. Stanford University, native to the internet.

4 key ideas we hope you take from this memo:

1. On Deck is already a substantial business, and is on track to 10x (again) in the next 2-3 years.

  • On Deck existed as a vibrant, volunteer-run community for three years before becoming a business. This "accrued goodwill" establishes both an authentic foundation for our community values and a substantial headstart over would-be competitors.
  • On Deck drives meaningful value for our customers with significant pricing power. Fellows even recommend we charge more, and publicly call for annual plans and subscriptions.  
  • Most communities are chronically undercapitalized. On Deck uses its pricing power/program revenue to hire the best talent, and invest in creating exceptional experiences. This in turn helps build reputation and drives new member demand, enabling further investment in R&D, acquisition, and distribution. A self-reinforcing flywheel:
↑ Source: The internal community flywheel

  • Scaling communities is hard, but we think we’ve cracked the code. At On Deck, each fellowship cohort is simultaneously small and intimate (think: "class"), nested within a broader, highly aligned sub-community ("program"), and woven into a larger ecosystem ("campus").
  • The secret: each new program contributes a specific "supply" that meets an existing "demand" we identify within our network. For example, our founders, angels, and talent fellowships are tightly interwoven. See the full "flywheels" thesis laid out on Twitter here.
 ↑ Source: The cross-community flywheel

  • While the majority of our current revenue comes from consumer-facing programs (where each Fellow pays personally), we now have our first career programs live — think: “YPO for X.” These sell into the "Learning & Development" budget, and are typically expensed to an employer.

2. Our customers LOVE us.

  • In a completely unsolicited fashion, many of our customers add On Deck to their Twitter and/or Linkedin headlines — choosing to align their core professional identity with their participation in an On Deck. To our knowledge, this is unprecedented within the tech industry.
  • Customers are exhibiting strong "repeat buying" behavior.
  • Our NPS consistently polls around 65-70. Even better: customers actually "walk the talk," making over 2,500 referrals in the past twelve months. This constitutes one of our biggest growth channels.
  • Of 2,000 people in the Founder Fellowship ("ODF") Slack Channel, 72% are active 3 months later, even after completing the 10 week program (most Slack communities retain 5-10% engagement maximum). Slack's Head of Enterprise Sales recently stated: "On Deck is an absolute anomaly — we’ve never seen a community like it.”
  • Participants have achieved very real success against a broad range of goals. Most notably, at least 330 companies have been founded and collectively raised upwards of $250M pre-seed/seed funding during the On Deck Founder Fellowship, in just 18 months.
↑ Source:

3. Why this team? 

We have assembled an all-star, rapidly growing team of former founders and experienced entrepreneurial leaders to scale into this opportunity.

Our fellowship communities offer a true unfair advantage when it comes to recruiting, allowing us to see talent and build relationships with hundreds of candidates before they get close to our internal team pipeline. Nearly a third of our current team were hired from the On Deck community.

4. Why now?

On Deck is riding a series of (at least) four "macro" waves / tailwinds:

  • The decline of traditional higher education and rise of "ed-tech 2.0," which anchors around the "re-bundling" of virtual curriculum and community.
  • The shift into the "deployment age" of the internet. Software has eaten/infiltrated the world. The half-life of professional skills has fallen to five years. Most people haven't yet learned to thrive in this new economy.
  • A shift to distributed living/working as the new norm — as accelerated by the COVID-19 pandemic. On Deck is "Silicon Valley in the Cloud".
  • The decline of organized religion, and an ongoing search for meaning, identity, and community in modern life (see: Peloton).

The goal of this Series A raise was four-fold:

(1) Further accelerate our engineering and product hiring. The On Deck product is an invaluable part of the experience, but also has break-out potential as a viable LinkedIn competitor. We're in full blitzscaling mode, and want to prioritize talent acquisition.

(2) Build a "war chest" (cash + equity value) to deploy an M&A growth strategy. Communities are valuable intangible assets — but most are extremely undercapitalized, make for commercially attractive targets, and offer high ROI once we plug in On Deck’s “distribution.” We have one completed example in "Lean Hire" and another which we have yet to announce. 

(3) With IRL returning, we have identified a unique opportunity to own the space between virtual education and physical connection — and want to accelerate into this opportunity. We’ve already had great success with our IRL Miami and NYC drops.

(4) Give our early supporters and community the opportunity to participate in the value they've helped to create, building an army of advocates in the process.

The On Deck Journey || Where we came from

Founded by Erik Torenberg in 2016, On Deck first emerged as an under-the-radar community and dinner series for repeat founders and experienced engineering, product, and operating talent to explore their next move — to be “on deck” in confidence, among a highly curated community of their peers.

In the first three years, over 5,000 people attended small, intimate On Deck dinners in 23 cities around the world, coordinated by a rolling cast of volunteers. On Deck CEO David Booth was one — joining to launch and lead our European chapters while living in London in 2017.

Early On Deckers at these dinners connected with co-founders, investors, and first hires —— and helped countless others by making introductions, brainstorming ideas, and being a sounding board through the process of starting up. The seeds were planted for many impactful friendships, investments, and companies.

Early retreats, first Fellowships

Momentum in the community built throughout 2018, culminating in a series of highly successful "founder retreats" in early 2019.

In June of that year, we launched the first On Deck Fellowship, pitched to the community as:

an intensive 8-week program for experienced engineering, product, and operating talent in the earliest stages of starting new startups.

120 Fellows joined the first cohort in person in San Francisco, attending a series of thematic dinners and co-working days, and founding a series of notable startups. Participants in that first group included Sean Linehan and Katie Kent of Placement, Maksim Stepanenko of Primer, Andrew Connor and Sam Corcos of Levels; Brandon Hill of Vori, Noor Siddiqui of Orchid, and many more.

The second Fellowship launched in October 2019 with ~120 Fellows in San Francisco and ~80 in NYC. For the first time, the signs of a powerful online community started to emerge, as Fellows connected cross-country to share knowledge and create early online programming.

COVID-19 and the unexpected virtual "product-market fit"

In March 2020, everything changed. One week out from the third On Deck Fellowship, we made the difficult (and at the time controversial) decision to cancel the physical ODF3 kick-off retreat — and delay programming a month until the threat had "passed." Battening down the hatches, we prepared for the worst. We didn't know if the community would survive.

But from that all-time low sprung a new high. The "virtual kick-off retreat” struck a chord, creating an instant bond among our group of ~170 Fellows. As the COVID crisis started to unfold, the On Deck community rallied: fellows sprung into action, launching 50+ projects to support those in need — sourcing PPE, developing and distributing tests, and so much more.

To its participants, ODF became a lifeline: a source of "serendipity" and supportive community for many, otherwise isolated during this most vulnerable stage of company building.

Uncertainty is a catalyst for opportunity. New norms create new needs.

Fellows were now busier than ever — forming teams and raising solid rounds, setting out to build impactful startups — when the world needed them most.

We rode the momentum into the announcement of another, totally virtual cohort: ODF4 doubled down on the global, distributed audience, and introduced a dedicated curriculum for the first time.

It's time to BUILD new institutions

In a post-COVID world, the cracks were starting to show in the institutions we grew up with.

On Deck set out on a mission to 10x the number of founders building world-changing companies. And we weren't stopping there...

If we plan to 10x the number of founders in the world—we reasoned—we should also build the ecosystem in which they can thrive. Seeing latent demand among our community, and with a desire to help more experienced operators get started investing in the next generation, we launched our second Fellowship: On Deck Angels. A new narrative was emerging:

*...ODF is for experienced talent in the earliest stages of starting companies.* 

 *...ODA is for experienced operators getting started as angels.*

The On Deck Flywheels || Our strategy & approach

Coming into 2021, we are entering what will be one of the craziest periods in On Deck history.

We are currently scheduled to kick off no fewer than fourteen new programs in Q1, with an ambitious target of launching 100+ cohorts across 25 programs in 2021.

With such aggressive pace, it's reasonable to ask: what's the play here? Why so many?

The Internal On Deck flywheels — compounding loops

We start by analysing the original Founder Fellowship — our most established community. We asked our Fellows: "Why did you join ODF?"

They said:

  • meet co-founders, early hires
  • obtain new knowledge
  • make deep, lasting connections
  • help others
  • build an MVP
  • raise funding
  • meet early customers
  • expand their network
  • narrow in on a specific idea

There's a "flywheel" spinning inside each community — simple on the surface, yet extraordinarily powerful:

  1. People pay a material amount to join a program: $2k-$10k. They then have "skin in the game" — and feel motivated to get their money's worth.
  2. We use that revenue to hire exceptional talent and dedicate them 100% to...
  3. Creating and curating incredible experiences, in particular through the facilitation of peer-to-peer interactions and user-generated content...
  4. This helps our members realize a lot of value — knowing the best way to benefit from the network is to first contribute to it.
  5. As the community’s reputation grows, so does new member demand.
  6. More demand allows us to better curate an ever stronger community — accelerating the flywheel further.
  7. Repeat.

The resulting community can uniquely help Fellows progress or exceed many of their goals and expectations by making deep, lasting connections, obtaining new knowledge, helping others, and so forth.

But for other goals — things like meeting co-founders, making early hires, raising capital, getting distribution — a small, intimate community will only get you so far. That is why we built...

The inter-community flywheels — bootstrapping marketplace supply

The first three things early-stage founders need most of all are:

  • Capital 💵
  • Talent 👩‍💻
  • Distribution 📢

The optimal state of these three is a marketplace.

The larger, more liquid, and "data-rich" this market, the more utility it creates for any given individual participating in it.

“In the long run, the ideal is to offer utility to your userbase... it's the most stable, long-term competitive advantage that you can have. However, it's also true that a lot of network-based utility is only realized at some level of scale. And so the question is, how do you get to that scale?” — @eugenewei, on the @NFX Podcast

So the question becomes:

Do we expand the ODF community and build the market internally? We have enough demand to add thousands per cohort. Or would that undermine the value loop that makes ODF so special today? 🤔

Here's the secret master plan:

On Deck is building a series of adjacent communities that each bootstrap “supply” to another's demand.

Each community is independent, intimate, focused on deeply understanding and serving the needs of a specific customer "persona" while simultaneously helping those customers achieve "marketplace" outcomes through their interaction with other communities.

Critically, every program is the centre of its own universe. For example, here’s what the value proposition looks like from the perspective of ODF vs. ODA:

On Deck Founders:

  • ODA (Angels), ODVC (Investors): capital
  • OD50 (First 50), ODNC (No-Code): talent
  • ODL (longevity biotech), ODCT (climate tech), ODH (health tech), ODDT (deep tech), and other sector-specific fellowships: specialized knowledge, talent

On Deck Angels: 

  • ODF, ODNC, ODCT, ODH: dealflow
  • OD50: recruit talent for your portfolio
  • ODVC: share jobs, scout capital, build relationships
  • ODLPs (coming soon): LP capital

Additional Resources: Explore the full "On Deck flywheels" and specific engagement between programs here

The On Deck Access Fund: the "meta" flywheel

Technology is a powerful force for good.

But while its use has become ubiquitous, the ability to participate in its development and the resulting wealth creation is severely limited.

The tech industry has an “access” problem, and it’s never been more obvious than in 2020.

We think a lot about how to “unlock” talent at On Deck.

We are on a mission to multiply the number of founders building world-changing startups, and create the world’s best support ecosystem around them: angels, early hires, distribution, and more.

For every person founding or working on an impactful company or cause today, there are hundreds who should be but can't.

In September 2020 we announced the On Deck Access Fund to support underserved talent in tech through scholarships and up to $1M in matched donations.

The On Deck Product || Come for the community, stay for the “Market Network”

A "Market Network" combines the main elements of

  • Marketplaces (think: eBay, Lending Club) and
  • Networks (think: Linkedin, Facebook, Twitter)

...and often provides a “SaaS” layer to facilitate transactions, aligning long-term interests with its users over quick one-off transactions. 

Market networks are also unique from a monetization and defensibility standpoint. They combine the strong network effects, defensibility, and scalability of direct networks such as LinkedIn with the lucrative revenue models of a SaaS, or, in our case, the education business.

The "Campus" to On Deck’s "College"

At On Deck, every Fellow is simultaneously:

  • matched and placed into a small, intimate group: a "squad", or "accountability group"
  • part of a larger, but still close-knit cohort (think: "class"), which is
  • nested within a broader, highly aligned sub-community ("program"), which is
  • woven into a larger ecosystem ("campus").

This "campus" is the On Deck Directory a unique combination of custom-built private social network  (think: AngelList/LinkedIn meets "Quora") and innovative usage of Slack, which provides the integrated communication layer (think: campus "common areas"). 

From the standpoint of this product, the education business serves as an incredibly effective, well-aligned revenue and engagement driver. Each cohort is like an 8-10 week-long product onboarding to create loyal users for life.

Users populate their On Deck profiles with far more detail than they do LinkedIn, AngelList, Twitter, or any other professional networking product.

On Deck is a "full stack" community

The old approach startups took was to sell or license their new technology to incumbents. The new, ‘full stack’ approach is to build a complete, end-to-end product or service that bypasses incumbents and other competitors.” - Chris Dixon, a16z

At On Deck, we are obsessed with Fellow experience.

To deliver the best experience, we need to own the experience end to end — and most importantly, use that ownership to understand how people interact with our product and how these interactions correlate with success.

This dedication has led to the Directory becoming an increasingly key part of the On Deck experience.

Between the nodes: On Deck’s Talent Marketplaces

At its core, On Deck is successful when we accelerate the rate at which talent connects with opportunity. Many join On Deck communities explicitly or opportunistically searching for a new role or project to work on. To facilitate this, we’re in the process of building several Talent Marketplaces that can help facilitate connections across a variety of categories of opportunities (co-founder, full-time, contract-to-hire, freelancer, and advisory roles).

Our most mature Talent Marketplace is Lean Hire.

For some roles, a contract-to-hire can be a win-win for both company and candidate. Classic interview processes can stretch for months, biasing on credentials and first impressions ahead of actual ability to build and perform on the job. The wrong hire can significantly impact teams, especially for senior roles.

On the other side, there’s substantial career risk for senior talent joining an early-stage venture. Establishing fit with culture, mission, and vision is vital before going full-time.

Lean Hire is an opportunity to “try before you buy".

The platform is free for candidates who have participated in any On Deck Fellowship, and charges a 20% "rake" for non-On Deck community members, simultaneously creating a valuable cashflow stream and a powerful incentive to join and stay in the On Deck ecosystem. The platform also charges a placement fee for companies that find full-time hires.

Job Boards

On Deck Fellows have access to an internal job board visible only to Fellows. Companies founded by On Deck Fellows can also feature their roles on the On Deck careers page.

Talent Hub

On Deck will soon launch a “Talent Hub” where vetted companies and candidates — with On Deck Fellows —  will be able to connect over opportunities and roles in a more nuanced way.

Additional resources: 

The Macro Backdrop || Why now?

On Deck is riding a series of (at least) four "macro" waves/tailwinds: 

  1. The decline of traditional higher education and the rise of "ed-tech 2.0";
  2. The shift into the "deployment age" of the internet;
  3. A shift to distributed living/working as the new norm accelerated by the COVID-19 pandemic;
  4. The decline of organized religion, and an ongoing search for meaning, identity, and community in modern life.

1) The decline of traditional higher education and the rise of "ed-tech 2.0"

Even before the COVID-19 pandemic, the university as an "institution" was in trouble.

The top U.S. colleges were all founded 200+ years ago, established to train citizens to be productive members of industrial-era society. Coasting on institutional momentum and credentialism, most have long since detached from reality.

Over the years, these learning communities began bundling education, community, and credentialing along with an ever-expanding list of functions in society. As “cost disease” set in, bloated administration forced endless tuition hikes. A disconnect from the realities of the job market resulted in a painful lack of career outcomes.

Over the last decade, many have tried to unbundle the university. Massive open online courses (“MOOCs”) unbundled the education component, accelerators and fellowships unbundled the network for certain careers, and companies like Github and Behance unbundled the credential for specific expertise areas.

But on the education front at least, MOOCs failed to live up to the hype. These programs failed to grasp a critical component of the learning process:

Learning is defined by who you learn with – the respect and perspective you develop among the camaraderie of the “classroom.”

According to The Rise of Universities, the term “university” simply refers to any group of people who came together for the purpose of learning. Curious individuals, learning together.

The core innovation at On Deck is not necessarily better education, although our programming does feature world-class guests, a growing content library, knowledge base, and thriving community.

On Deck is special because it re-bundles community with learning, and a commitment to outcomes.

2) The shift into the "deployment age" of the internet

The internet is a technological revolution, which is entering what Carlota Perez calls its "deployment phase".

The past ~250 years have seen four such great technological revolutions and the first half of a fifth. Each is characterized by a critical factor of production suddenly becoming very cheap, new infrastructure being built, and widespread gains in productivity from the newly developed technology.

In the “deployment phase”, what was new is now the “new normal”: Technology infiltrates every aspect of the economy but becomes invisible.

Software eats the world, and everybody stops noticing it.

Where do you go to learn to thrive in this world? Probably not college (see above).

Meanwhile, the half-life of a professional skill has fallen to 5 years. The only constant throughout your career will be change.

Today, most people finish school at 18 - 22 and never go back. Does that make sense?

Some say accelerators like YC are already quasi-education institutions. But VC is ultimately a feature of the past "installation" cycle. Many will continue to create immense value, but their best years are behind them.

3) A shift to distributed living/working as the new norm, accelerated by the COVID-19 pandemic.

The biggest impact of COVID-19 may be remote work. Pre-pandemic, roughly five percent of full-time employees with office jobs worked primarily from home.

That figure is likely to settle at 20-30 percent in the new normal, with variation across occupations and industries. Tech in particular makes clear that location will become less important in hiring.

4) The decline of organized religion, and an ongoing search for meaning, identity, and community in modern life.

In the 70s, the U.S. was a God-fearing nation. People were religious, with strong associations with their church or synagogue or mosque or whatever you grew up with.

Over the past 50 years later, society has experienced a dramatic decline in people's association with organized religion.

That's not to say that people no longer value guidance, ritual, identification, music, ceremony, spirituality, and reflection. The stuff that happened on Sunday morning at church or synagogue is still important to human beings and we believe it's still something humans need. So they're now looking elsewhere, and finding that fulfillment in communities, particularly online.

In the 70s and 80s, many wore crosses or Stars of David on their necks. Increasingly, we're seeing people identify with others as part of secular communities: they wear a SoulCycle tank-top, a Warriors jersey, an HBS hoodie, or a Barry's hat.

That's your identity. That's your community.

Team // Who we are

We have assembled an all-star, rapidly growing team of former founders and experienced entrepreneurial leaders to scale into this opportunity.

A Monopoly on Talent

The On Deck communities offer a truly unfair advantage when it comes to recruiting.

We have a birds-eye view over thousands of monthly applications from individuals of all different backgrounds, from the most junior engineers to senior technology executives with illustrious careers scaling top tech companies.

By inviting such talent to join our Fellowship programs, we have the opportunity to see them in action by observing their trajectory, gratitudes received, and alignment with On Deck values. We build relationships and trust and identify "hidden gems" before the market.

For the talent, they have an opportunity to experience our product first hand and by extension, to witness much of how On Deck works as a company before making the decision to join.

Over a third of our current team were hired from the On Deck community in this way, including two-thirds of our program directors.

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