Open-sourcing the playbook that took our 150-person overnight retreat "virtual" [COVID19]

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
Article Category

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
Sachin Maini
Editorial and Content Lead
Heading 1
Heading 2
Heading 3
Heading 4
Heading 5

Heading 1

Heading 2

Heading 3

Heading 4


Paragraph text goes here

Block Quote looks like this
  1. List 1
  2. List 2
  3. List 3

Looking back over the last month, the decision to postpone an overnight retreat in early March — with 140 talented founders flying in from around the U.S. — seems obvious. But in late February with our Fellowship cohort kick-off around the corner, the On Deck team was feeling nervous.

Since founding in 2016, On Deck has been a community anchored in facilitation of intimate, offline experiences — getting “in the room” with small groups of talented people in the earliest stages of starting or joining new ventures.

Like many, we always assumed the “room” had to be a physical one — but faced with a looming public health crisis, we decided to postpone all in-person programming until there was more clarity around the COVID-19 pandemic (opting to get creative with virtual programming in the meantime).

Starting with the kick off retreat — and continuing into small, thoughtful daily events and activities, the On Deck Fellowship is now 100% digital. But it’s not your stuffy, boring webinar series. The secret to On Deck is “manufactured serendipity” — reproducing the magic of hallway and dinner table conversations

We think we’ve cracked the formula for online serendipity — and in the interest of helping you all stay sane — we are now open sourcing that playbook. 

What Fellows were saying after the event

We’re open-sourcing our “Virtual Offsite” Playbook

It’s now more important than ever to share notes and help others—in the tech community and beyond. 

As such we’re taking this opportunity to open-source our learnings and tactics for designing and putting on memorable remote-first experiences. We hope that other organizations and communities can pull inspiration from this when designing their own events.

In this post, we’ll share: 

  • How we approached a remote-first event.
  • Examples of some of the virtual programming we included.
  • A bunch of highly tactical tips for organizing and executing a virtual event.
  • Things we’re doing post-kickoff to continue the momentum

We hope this guide for remote-first experiences can serve as a valuable resource. We believe having a strong community around you has never been more important.

Goal of the (Virtual) On Deck Fellowship Kickoff

The On Deck Fellowship is an 8-week program that creates an incredible community of 150 repeat founders, experienced engineering, product, and operating talent in the formative stages of starting a company, where we design an abundance of opportunities to meet co-founders and early hires through a series of dinners, retreats, workshops, co-working days, and 1:1 intros to experts, mentors and cohort alumni.

With the kickoff retreat, we wanted our Fellows to arrive as a group of strangers, and leave feeling like a big family that they could trust, be comfortable seeking advice from, and eager to support each other.

It was important that we instilled On Deck’s Guiding Values, which are the foundational pillars behind the pay-it-forward culture and positive-sum attitude of the community.

🔑 Video-chats often break down with anything over ~8 people. With this in mind, we designed the entire event as a series of small group breakout sessions.

(🔑 = Takeaways)

Programming Ideas

Both the communications leading up to the event, and the sequencing of programming during it, are critical to get right. We knew our event would be a failure and ruin our attendees’ first impressions of the On Deck Fellowship community if we weren’t intentional about setting the mood and expectations from the start.

We had a few ideas for creative programming we wanted to experiment with, so we started leaving breadcrumbs publicly on Twitter (i.e. virtual carpool tease and crowdsourcing icebreakers) to build the intrigue, and sprinkled some humor into our communications. Humor is important—especially when people are feeling anxious about the state of the world. By setting expectations and keeping things fun, the attendees were ready for the creative virtual programming we had in store for them.

Below are some examples of the programming and activities we included in our “Virtual Kickoff” that we felt worked well in the virtual format:

Zoom Bingo

A great "expectation setter" since it showed we were adding a bit of humor to this, and that some minor hiccups/technical difficulties were to be expected when running a fully remote event over video stream. 

Virtual Carpools

As attendees trickled in at the beginning of the event, we assigned each guest to a “car” (i.e. Zoom breakout room), and gave the following instructions:

  • 1 person should screen-share a “POV Driving” YouTube Video (this one is good). 
  • Mute the Youtube video audio, then play a Spotify playlist at low volume to simulate a car radio in the background (it may sound wacky, but it actually worked really well!)
  • Go around the car and answer the following questions: A, B, C

This was a big hit, and set the tone for the rest of the event: this was all about virtually recreating much of the same magic and serendipity you’d experience at our in-person kickoff retreat – even going as far as to recreate the carpool bonding on the way up to the “venue”.


Split the group into teams, use a random topic generator like this one, and let participants silently act out their topic. Was a great way to get some competitive juices flowing, and get people moving around out of their chairs.

Charades Random Topic Generator Example

“Hot Seat” / Rapid-fire Questions

In a game of “Hot Seat”, a group takes turns having one person be “in the hot seat”, where they’re asked a bunch of rapid-fire questions, and the person in the hot seat responds with the first thing that comes to mind.

We did a full-group one as an example and had one of our team members be the first to be  vulnerable in front of the whole group. Afterwards, we split into breakout groups of about 8 people and had each person go on the hot seat for 2-3 minutes.

Custom questions are the best, but if the ideas start to run dry, this question generator is a useful tool.

Freestyle Rap Session

No better way to break the ice than having people humiliate themselves trying to rap in front of a group of strangers, right? Erik spent the first part teaching the fundamentals in small learning blocks, which built up to an eventual virtual rap battle amongst the group. 

The only rule for attending the Freestyle Rap session: if you join, you can’t watch – everyone has to participate!

Disclaimer: we do not recommend this activity unless your founder is a rap genius.

Two truths and a lie

Each person in the group goes around and shares three “facts,” and the group has to guess which one is the lie. After they reveal their “truths,” the group is encouraged to dig in a bit and ask about the story behind the facts/lies.


You can use the Zoom Whiteboard feature to share a blank whiteboard, which you can then draw with your mouse the topic, person, animal, etc and the group tries to guess it.

Pictionary using Zoom Whiteboard


The takeaway here is the only limits for virtual icebreakers are that of your own creativity! (Got any other ideas? We’d love to hear them! Tweet at us :) )

Tactical Tips and Execution

This section is intended to be fairly tactical, so will be most applicable to those looking to organize remote events in the future.

Leveraging Zoom+Slack

Unsurprisingly, the heavyweights of remote tools, Zoom, Slack and Google Docs, are currently the optimal tool stack for most virtual events. 

There may be fancier tools with more bells and whistles, but sticking to the basics is the most reliable and lowest friction experience.

Below are some of the best ways to utilize them for remote experiences.

Zoom Breakout Rooms

🔑 Zoom’s “Breakout Rooms” feature is the most well-kept secret on the planet...

With it, the power and value of Zoom for running virtual experiences with large groups increases by 5x, since you can use these to split up larger “gatherings” into more intimate groups for breakout sessions. You need the upgrade to their Small & Medium Business plan, but it’s well worth it, especially if it’s just a one-off occasion.

You can split participants into various breakout rooms in one of the following ways:

Split participants into pre-assigned breakout groups in one-click:

  • You can import a CSV to Zoom of which participants to put in which room
  • This was helpful when we knew we wanted to group certain attendees with others, so once we hit that part of the agenda, we clicked a button, and everyone perfectly dispersed into these carefully curated sub-groups.
CSV Import to Pre-Assign Breakout Groups

Automatically split participants

  • You can randomly assign participants to groups of N participants by setting a room count that will divide your participants into the group size you desire.
  • For example, if you had 144 participants that you wanted to split into groups of 6, you’d set the “Room Count” to 24.
Auto-split participants in one click

Manually assign participants

  • We did this to run our “Virtual carpools”: as each participant trickled in to our main Zoom room at the start of the event, we’d added them 1-by-1 to the newest “car” (i.e. Zoom breakout room) until we filled that car up with 5 people, and then would start a new car and fill that one up until it hit 5 people, etc.
Manually assigning to breakout rooms

How to do a breakout, within a breakout 🤯

The Zoom Breakout feature is great if you want to split people off from the main room into sub-rooms.

But what if, for example, you want to split the group based on three different activities. And then within those three groups, split each one again into even smaller breakout groups within those three rooms?

Essentially, you want to split the group once, and then re-split them one more time.

Our approach was to spin up three independent Zoom rooms (one for each activity) with an admin/host from the On Deck team running point on each one. We then posted hyperlinks to the 3 rooms in our Public Agenda doc, as well as Slack channel, so attendees could click the link for whichever room they wanted to join (see agenda screenshot below)

Once the group was split into each activity room, each host could then run their room normally – first introducing the activity/session to the full group, and then automatically distributing the attendees into breakout rooms once ready to split into sub-groups.

Zoom Polls and Audience Engagement

Creating opportunities for interactive activities with the audience is a good way to keep the group engaged, while also feeling like they have some control and influence over parts of the experience.

Zoom Polls are an easy way to accomplish this – you can ask an icebreaker question by voting on multiple choice options, you can let your audience pick the content for parts of the programming or a presentation, you can get input on a meeting, etc.

Poll: Is it pronounced "gif" or "jif"?

We used Zoom Polls to demonstrate and introduce the “Two Truths and a Lie” activity we were planning to do next. I shared my three “facts”, and the audience voted on a Zoom Poll which one they thought was the lie.

After we split the groups and they finished their session, we brought everyone back together and popcorn-style called out a few randomly selected participants to ask them to share the highlight from their breakout group. This was a good way to pull participants in from the audience to help tie the takeaways back in to the larger group.

In-Event Logistics/Communications

Tech Management

🔑 Over-prepare on how to orchestrate the logistics behind the scenes with the tech/tools you’re using. 

🔑 Do a dry-run walkthrough beforehand, and have someone dedicated full-time to running “mission control” during.

We’d highly suggest that you have someone whose full-time job during the duration of the event is to serve as “Mission Control” behind the scenes.

Orchestrating the room assignments in Zoom, communicating announcements on Slack, fielding inbound messages from attendees, and more. 

Ensuring these transitions and technical pieces run smoothly is critical – it’s high-stress, and too hard to have the person MCing also be juggling the logistics for running the remote operations.

Have someone whose full-time job during the event is to serve as “Mission Control” behind the scenes.

Managing the Agenda & Communications

🔑 Over-communicate the agenda and expectations, both before and during the event

For in-event communications, we prepared two versions of our agenda doc: one as the detailed internal doc with stage notes and talking points, and another as the public doc that attendees could access.

With the public agenda doc, you can share it in advance as just a rough skeleton of the main time blocks in the agenda. In preparation before the event, use the internal agenda doc to draft pre-written blurbs for each agenda block with detailed information attendees should know. You can then have these ready to go, and simply copy over each blurb into the corresponding section of the public agenda doc as each block approaches.

Copying pre-written blurb from "internal" agenda to "public" agenda

This workflow proved beneficial for a number of reasons: it keeps the full game plan a bit of a mystery/surprise for attendees, it lets you control the timing of communications so that you keep attention focused on the right information at the right time, and it prevents attendees from looking ahead at the rest of the agenda and prematurely deciding which blocks to attend vs skip.


In a world with increasing levels of loneliness, coupled with a global pandemic requiring millions of people to be stuck in solitary work environments, it is critical that we all find ways to help people connect and build relationships, while creating opportunities for laughter, knowledge sharing, and support in a remote-only world.

We hope by open-sourcing the learnings from our experience, this may inspire others around the world to create unique and memorable virtual experiences for those in their organizations or communities.

Anything you can do in-person, you can find a creative way to do remotely

If you’re interested in learning more about the On Deck Fellowship program – an 8-week program for 150 world-class founders all of whom are in the early days of starting their next venture – you can check out our website, follow us on Twitter, or subscribe to our newsletter in the footer.

Think someone you know may benefit from this article? Tweet it

Stay safe, and thank you for reading!

Get tactical advice sent straight to your inbox every month.

Aaron Appleton
Abhijeet Patra
Abhishek Anirudhan
Ada Nguyen
Adam Gelman
Afraj Gill
Akanksha Manik Talya
Alexandra Barr
Alexandra Worthington
Ali Greenberg
Alice Wilson
Allison Dea-Kemp
Amine Aboura
Amrutha Adusumilli
Amy Story
Anastasia Chapman
Andre Bjork
Andrea Torres
Andreas Klinger
Andrew Rea
Andrew Yu
Andy Barr
Angie Ryan
Ani Pai
Ann Ferracane
Ann Miura-Ko
Anna Drabovskaya
Anne Bosman
Anthony Nardini
Ari Calumpang
Ari Gootnick
Arielle Tannenbaum
Ash Wesley
Asher King Abramson
Asher LaBostrie
Ashna Mahtani
Ashwin Lalendran
Asta Diabate
Barry Conrad
Bea Aguila
Becky Stephens
Benjamin Plummer
Bernadeth Madlangbayan
Blake Arensdorf
Blue Davis
Boydie Maraj
Brandon Taleisnik
Brandon Zhang
Brennan Foo
Brett Wietecha
Brianne Ilagan
Callie Cox
Callum McDonnell
Cam Sadler
Candice Ammori
Carly Dalgleish
Carolyn Wakulchik
Chai Flores
Chaitanya Choudhary
Chamod Gamage
Chance McAllister
Charles Cushing
Charles Liu
Charlie Taibi
Charm Lagura
Chioma Kalu
Chris Moreno
Clara Ma
Conor Brady
Cooper Charlton
Craig Montuori
Cullin McGrath
Curtis Sandy
Danitra Blue
David Booth
David Fallarme
David Hoang
David Jeon
David Weinstein
David Zhou
Denise Devlyn
Dishita Shah
Don Ho
Donté Verrill Huffman
Eade Bengard
Edgar Brown
Egor Zaitsev
Eliot Gattegno
Eliza Popa
Emily Edmonds
Eric Friedman
Erik Torenberg
Erika Batista
Fadi Hindi
Fernando Wittmann
Flo Bühringer
Gajus Kuizinas
Gautam Shewakramani
Gianna Chan
Gonz Sanchez
Haleigh Wilson
Harry Siggins
Harshita Jain
Hayley Wade
Heath Jamieson
Holly Stinson
Ilia Schelokov
Imran Mumtaz
Jack Fritzinger
Jackie Miller
Jackie Williams
Jackson Steger
Jacob Ruiz
James Sinka
Jamie Farrell
Janel Loi
Jared Gordon
Jason Piersialla
Jenna Kellner
Jennifer Dyck-Sprout
Jill Kismet
Joanna Cohen
Joe Penn
Jolisa Masucol
Jon Kent
Josefin Graebe
Josh Sushan
Julia Culhane
Julian Weisser
Julie Carroll
Juraj Pal
Karel van der Vyver
Karthik Puvvada (KP)
Katarina Smith
Katie Kent
Katya Delaney
Kaylyn Lu
Keith Williams
Kelly Hook
Kelly Kang
Khanh Nguyen
Kieran Ryan
Lana-Lea Dennis
Laura Thompson
Lauren Hoffman
Laís de Oliveira
Lei Ugale
Leon van der Vyver
Lili Welch
Lital Zigelboim
Logan Pugh
Lorenzo Castro
Lucas Hasselfeld
Lucas Vieira
Manar AlSagob
Maranda Dziekonski
Marc Havercroft
Margot Black
Maria Jimena Sanchez
Mariya Boykova
Marshall Kosloff
Marty Bode
Matias Sanchez Sarmiento
Max Nussenbaum
Michael Bassani
Michael Butler
Michael Gill
Michelle Kwok
Mike Daugherty
Mike Wilner
Mindaugas Petrutis
Mindy Zhang
Ming Lu
Minn Kim
Mohga Koshty
Morris Huang
Naida Rosenberger
Natalie Toren
Nate Snow
Nathan Cheng
Neha Khurram
Niko Zona
Noémie Federico
Nur Sevencan
Olga Stogova
Oliver Fisher
Oscar Ramos
Owen Willis
Pablo Martinez-Falero
Pablo Pinto
Patrice Madurai
Patrick Blumenthal
Paul Gleger
Paula Abarca
Paulina Sicius
Pawel Cebula
Payam Salehi
Peter Martin
Peter O'Rourke
Phillip Lemmons