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Why On Deck Reinvented the Program that Launched $10 Billion in Startups
How On Deck, the program that launched 1,000 startups worth a collective $10 billion, reinvented its flagship fellowship program for founders.
Andrew Logemann
Andrew Logemann
Head of Marketing
min read

In May of 2016, Erik Torenberg launched On Deck as a San Francisco-based dinner series for entrepreneurs looking to start or join their next "thing."

Over the next three years, the dinner series evolved into a thriving global community: more than 3,000 people in 24 cities around the world used On Deck to meet co-founders, collaborators, and their first early hires.

Then in May of 2019, On Deck announced its next chapter: an eight-week program called the On Deck Fellowship (ODF) designed to get even more founders off the sideline and into the startup game.

Its first two cohorts were a huge success: in the back half of 2019, around 300 Fellows formed almost 80 companies and raised over $23 million in pre-seed funding.

And a third cohort was about to get underway in March of 2020.

Until COVID changed everything.

IRL gatherings–the very interactions that On Deck members relied on to meet their next co-founder, advisor, or early hire–were no longer on the table.

With lots of unknowns on the horizon and a series of high-stakes decisions at hand, the On Deck leadership team was forced to confront its situation:

  • Do we completely change the way we do business and build out an entirely new program and set of remote experiences?
  • Do we postpone our March cohort and tell the Fellows who just quit their jobs that we don't have a program for them anymore?
  • Do we try a remote-first program until COVID passes and then switch back to IRL-focused programs?

With the fate of the company hanging in the balance, the On Deck leadership team set out to answer these company-defining questions with the best information they had.

Listen as Adam Nathan, CEO of Almanac, sits down with Julian Weisser, Co-Founder of On Deck, to talk about On Deck's biggest decision of the last ten years: turning its historically IRL-focused On Deck Fellowship into a remote-first program.

Here's their full conversation.

On viewing hardship as a problem or opportunity

Adam Nathan: Let's get right into it. What was the biggest decision you made in the last ten years?

Julian Weisser: It was a decision we made in the early days at On Deck. And it was one that ultimately could have gone either way. If the outcome of the decision had gone the opposite direction it did, we probably would have been irrelevant right now.

We were faced with the decision on how to view hardship: either as a temporary problem or an opportunity that could potentially catapult the business onto an entirely new trajectory. Ultimately, the decision that we made caused us to be very successful. It's the thing that got us to where we are today.

So the decision was this: how are we going to react to COVID? We had a community and business that were entirely predicated on IRL experiences. At the time, COVID was just thought of as a potential nuisance that might last for a month or two. Ultimately, we had to decide how we were going to react to that as a business that was entirely focused on IRL experiences. We held in person programming, helped people meet in person, find co-founders in person, fundraise in person, etc. So we had to ask ourselves: what were we going to do to ultimately rise up to this challenge?

Why COVID forced us to make a decision on the future of our founders' program

Adam Nathan: Can take us back to March 2020 and tell us what you were feeling or thinking? What did the landscape and the future look like for you?

Julian Weisser: So there's a couple of things that are worth mentioning. The first is that the pandemic wasn't predicted to be as long as it ended up being. People mocked the "no handshakes please" policy that a16z had. People thought it was an overreaction. They thought that anything other than taking a pause was making much ado about nothing. So we had a world where there was a stark divide between people who thought this was the next serious health crisis and people who thought this was just going to be a blip.

Next, we realized there was another thing going on. The people who were looking at On Deck were looking to either quit their jobs or take time off to focus on building a company. And timing is really everything when it comes to building a company. For our founders, it's not like they could say, oh, I can wait to join your program six months from now. They were saying, the right time for me to start a company is now–not six months from now.

So, we had a decision to make: respect the timelines of the people who had committed to being a part of our program or just postpone things and say, hey, I know that you just cleared your calendar to focus on building a company, but we can't do these in person events anymore.

The other thing we were seeing was people were thinking about solutions to COVID as temporary bandaids. They weren't necessarily addressing the problem as if it was going to be a permanent thing. They viewed COVID as a temporary inconvenience, not like the world was changing and that they needed to change with it.

Why we wanted to go all-in on creating an exceptional remote experience for founders

Adam Nathan: Just to recap there: the world felt really uncertain and many organizations were taking a temporary approach to this question of where to work and how to work. But your founders, the people that you serve through On Deck, had a certain urgency to their commitment. I'm assuming one of the options you considered was to go fully remote and distributed. Were there other options you were considering, and how did you weigh the pros and cons of each?

Julian Weisser: So it really came down to two things: either postpone or go digital. But there was a nuance to it. We could go digital as a temporary measure (a.k.a. Zoom University), or we could go digital as the new thing. Ultimately, postponing wasn't an option because of the timing situation.

So then the question really became: do we go digital and sort of half ass it in a way that is only going to work for the next couple of months? Or do we do it in a way that we think is the future? Like, imagine a world where we never went back to doing in person cohorts of the On Deck Founder Fellowship. What would our service to founders be like if we never went back to an in person world and we stayed fully remote?

Obviously, we never expected the world to not open up again. But we wanted to build an experience that was so good digitally that people would find it valuable, even post pandemic. And I think that's the key thing here.

If you look at the universities, they all said, we're going to go back to business as usual once the pandemic is over. And largely, they were right. Though I think that a lot of people are now looking at them and saying, I don't necessarily know how much I value the university experience. And there are a lot of factors around that–like preparing people for jobs and that sort of thing.

Ultimately, we wanted to build something that wasn't just a temporary fix. We wanted people to feel like our remote product was a better product than if we had just done a purely in person product, even if we had the ability to do so.

Adam Nathan: So what decision did you end up making and how did you end up making it?

Julian Weisser: We decided that we were going to do a remote program, or an experience, that would be superior to an in person experience in a lot of ways. And we decided that the remote experience wasn't just going to be a bandaid. It was going to be as full fledged as possible.

I was leading a team that was building another product outside of On Deck, but we shut down that project and pivoted the team to focus on building internal tooling–ways for the community to access content like directories and things like that. And this was a thing that wasn't necessary back when we were predominantly IRL, but became extremely important and a core part of our experience once we went fully digital.

The people who joined the first digital cohort of ODF (On Deck Founder Fellowship) were predominantly based in the Bay Area, because they thought it was going to be in person. But for ODF Four, which was the second digital cohort, people came from all over the world because it was the first cohort that was digital from the very beginning.

And the founders in that cohort heard about ODF on Twitter and LinkedIn. Other founders were talking about how they found their co-founders and how they were having this really great experience. Especially during the pandemic–when loneliness was acute and feelings of helplessness and hopelessness were really ravaging people's psyche. Founders heard about this thing where optimists were coming together and learning from each other and exploring ideas together. And that became really this oasis at a time when people really needed it more than ever.

How the remote experience opened up a world of opportunity for our founders

Adam Nathan: So I guess it turned out well! Were there any surprises along the way that you didn't expect when you originally made the decision to go fully remote?

Julian Weisser: We were surprised by just how well received it was. ODF was popular before the pandemic, but we were worried about how people would react to a digital cohort in place of our usual IRL cohort. We thought people would cancel.

But as it turned out, no one canceled. That was pretty wild to see. And people came with open minds and open hearts, and they ended up having an incredible experience. One that really changed the entire dynamic of the pandemic for them. So that was the first thing that surprised us–just how powerful the first digital cohort turned out to be.

The other thing that surprised us was how much the world opened up for so many founders once we went digital. All of a sudden, they could participate in what was really a Silicon Valley company in ethos. Like, the way that we act, the way that we behave, and the way that we think about things have typically been geographically locked. Traditionally, you could only get access to these ways of thinking and these ways of learning how to build businesses if you came here. Which isn't to say that there aren't flaws with those things, but you wouldn't have been able to have access that type of education unless you came here. And we really changed that by going digital for ODF Three and beyond.

Why you should always look for an opportunity when faced with a challenge

Adam Nathan: If you were to abstract from the specific case for founders who have to confront an uncertain future and make an important decision, what advice or lessons do you have for them?

Julian Weisser: Ultimately it comes down to how you deal with adversity and how you think about the type of adversity that you're dealing with. Is it a minor inconvenience? Is it a road bump? Is it a thing that's potentially going to shift the entire dynamic of your business?

If it's something that seems like it's going to be relatively long standing in terms of an issue, or thing that's challenging your business, are you using that as an opportunity to really evaluate where you could take this business? And use that not just as a challenge, but as a thing that could actually boost your business?

For us, it was like, okay, people are now in their homes. If they worked in an office, then they loved the camaraderie of being around their teammates or the various types of coconut water. Pre COVID, there was this one unicorn that served five different types of coconut water in the office. But once COVID hit, you didn't have the five different types of coconut water anymore. So then people were more inclined to say, hey, maybe I was just staying at this company because of the coconut water and the teammates that I liked, versus this was the thing that I actually wanted to do with my life.

And when you had that happen, we were in a place to serve these people and help them go and do things that were much more meaningful. I think that was the thing–can you find an opportunity out of the challenge?

Adam Nathan: Yes, that is great advice. It sounds like doubling down, or once you make a decision going fully after it and not being half in and half out, is critical to success as well. Thank you so much, Julian. It's fascinating to hear about how On Deck became the behemoth it is today from one of its co-founders. Appreciate you joining us today.

Julian Weisser: Thanks for having me.

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