The Magic of Engineered Serendipity

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
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At the beginning of this year, I joined On Deck – a fellowship of entrepreneurs at various stages of launching their startups – with the goal of expanding my professional network in the Bay Area and finding a co-founder for my next venture.

On Deck was designed as a 10-week onsite program, with social events such as weekend trips, lunches, etc. However, no one had anticipated a global pandemic to strike, and On Deck had to switch to fully remote operations even before the group had a chance to meet in person.

The decision to continue as a remote program came a few weeks before the cohort start date. By then, I have already flown into San Francisco, rented a place, and was testing several startup ideas. As such, the announcement was a huge blow to me, and I was disheartened to learn that the sessions would be conducted online. All the dinners, parties and team bonding activities I was looking forward to have been replaced with Slack chats and Zoom calls.

In retrospect, it is incredible how quickly On Deck managed to reorganize the entire curriculum into a fully-remote event. Kudos to their swift response and hard work in making On Deck 2020 possible! If they had cancelled the cohort, I would not have met all the amazing people and my co-founder.

So how did it all play out?

The first day started with a 4-hour virtual kickoff session. We were split into groups and played icebreaker games. Through introductions, games, and breakout activities, we got to know everyone in the cohort.

Without us knowing at the time, our groups were not random. On Deck evaluated the participants and thoughtfully paired those with complementary skills together. Therefore, it was not entirely coincidental that the first person I spoke to that day became my co-founder (months later). Job well done On Deck!

What followed was 10 weeks of diverse activities:

  • Breakout sessions
  • Hackathons
  • Speed dating
  • 1:1 meetings
  • Virtual dinners

The breakout sessions were a dream come true – imagine the cool founders you follow on Twitter all appearing in your calendar: Julia Lipton, Ryan Hoover, Vinay Hiremath, Andreas Klinger, Elizabeth Yin, and so on. You are free to select topics that are relevant or of interest to you to attend. Each session has around 10 participants, so there are ample opportunities to ask questions and interact with the speaker.

Snack was built for an ODF hackathon.
(Snack was built for an ODF hackathon)

Meanwhile, hackathons allowed groups to work together and demonstrate their strengths. It was during one of these hackathons that I built Snack. On Deck were the first adopters and their feedback shaped the product today. At this point in time, I already had several conversations with my future co-founder on starting a business together. I look up to him & like what he is working on, and him seeing me build a hackathon project that grew to be used by hundreds of Slack organizations is what sealed the deal.


My co-founder (Ben) and I are building a professional network for people you actually work with. Meanwhile, Tracy has taken over the day-to-day Snack operations of providing serendipity-as-a-service to teams.

Joining On Deck is undoubtedly one of the best moves I have pursued. Never have I thought a virtual program could be this engaging and inspiring. In fact, the 10 weeks with On Deck were some of the most sociable weeks in my professional life, and the sense of community continues to be felt to this day.

On Deck did an excellent job creating what felt like serendipity, but is actually a diligently orchestrated event with hand-picked individuals that form a supportive community of shared goals and deep subject expertise. I am excited to share the magic that I felt during On Deck with you through Snack. ❤️

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