Alumni Posts

On Deck Fellowship: My Experience And Why You Should Apply

January 24, 2020

Pujaa Rajan
Applications to the March 2020 Cohort are now open
APPLY NOW


Have you ever felt like it’s time to move on from your current company and role  but not sure what you want to work on next? 


I felt like that after I quit what I thought was my dream job in finance at BlackRock, the world’s largest asset manager, and pivoted to startups in the technology industry. 

If you’re restless and excited to explore, then you’re like me. You’re “on deck”, trying to figure out what boat you’re going to take and who’s going to be your crew. In other words, you’re taking time to explore your next step and find the people and mission most aligned with your values. 

If this is you, then I encourage you to apply to the On Deck Fellowship (check out the announcement post for the March 2020 cohort).

About the On Deck Fellowship

The On Deck Fellowship is a curated community of entrepreneurial people in the technology industry trying to figure out what they want to do next together. 

I heard about On Deck from Shriya Nevatia, founder and CEO of The Violet Society, and applied online. I was selected to be an On Deck Fellow in the Winter 2019 cohort. I accepted the invitation with the goal of meeting others who were interested in technology and entrepreneurship.


What is the program?

The On Deck Fellowship (ODF) is 8 weeks of world-class programming, jam-packed with events, discussions, and debates almost everyday. It mixes in a combination of full-cohort events (retreats/hackathons/dinners/workshops), along with smaller interest-based events (biotech, future of work, healthcare, enterprise/SaaS, etc). 

Beyond that, ODF creates an abundance of opportunities for small group and 1:1 conversations throughout.  Events include:

  • Weekday hack days at coworking spaces and weekend hackathons.
  • 1-on-1 matches for you to get to know.
  • Dinner clubs to get dinner with random small groups.
  • 2-day immersive deep dives into a specific topic.
  • Expert talks, fireside chats, panels, and webinars.
  • Facilitated small group discussions.


On Deck organized events not only for us to mingle, but also for us to learn from experts in various domains. For example, Keith Rabois spoke at one of the On Deck events after a group dinner. Keith is a Partner at Founders Fund, a member of the PayPal mafia, and a co-founder of OpenDoor. He spoke about what he’s invested in and why, what makes for good ideas, who are good founders, and how to start a company. 

A key takeaway: Good ideas don’t come to you overnight. Keith said he waited 10 years to find the right people to build Opendoor. 

Here are a few inspiring quotes from his talk:

  • “All rules are meant to be broken”
  • “If Henry Ford built what customers wanted, then they would have built faster horses.”
  • “You start with a vision. Then you cast the actors and create a trailer.”


Who else is in the On Deck Fellowship?

I met ~100 other On Deck Fellows, including accomplished engineers, lawyers, product managers, investors, and more, in the span of the 8 week cohort. There was a group of people passionate about artificial intelligence, which is my primary interest. If you’re reading my blog, then there’s a good chance that you are too, so I’ll list a few cool artificial intelligence experts I met: Alexander Galindo co-founded View Factor, a computer vision traffic control system. Preetham Vishwanatha founded Kena.ai, which applies artificial intelligence to provide feedback to your music practice sessions across 13 musical instruments including vocals. And many other talented engineers.

I met 100 other On Deck Fellows, including accomplished engineers, lawyers, product managers, investors, and more, in the span of the 8 week cohort.


I was excited to meet a diverse group of people outside of AI, from different backgrounds and locations as well. Many fellows were repeat founders, early employees at what are now breakout companies and unicorns, senior executives at large-scale companies, or subject matter experts. Let’s look at the numbers:

  • ~50% based in San Francisco, ~30% based in New York City, and the remainder were scattered around America and even a few internationally. I met Manar AlSagob who moved to San Francisco during On Deck from the Saudi Arabia. 
  • ~50% came from a technical background - a great place to link up with a technical or non-technical cofounder! I was able to broaden my non-technical perspective while my technical background was valued. 
  • 40% engineering, 20% product, 20% business, 20% other backgrounds. You’ll find an expert in whatever you’re looking for in this community. The curation of this group is what sets it apart from open meet up groups.
  • 50-60% are working full-time on their companies. I wasn’t, and still encourage you to apply to the program if you plan on starting something new in the next 3-6 months.
  • ~35% openly exploring, 40% exploring a specific idea, 20% have a prototype/MVP, 5% actively fundraising.

You’ll find an expert in whatever you’re looking for in this community. The curation of this group is what sets it apart


David Booth, the co-founder and CEO of On Deck, and his small and mighty team, are the kindest people who are dedicated to helping people find what’s next. They will connect you with people they think you’d like to meet and were always actively soliciting feedback to better personalize the program for each cohort. They are also creating a job search network, Via, and a peer-to-peer credential called Cosign that’s already being used by thousands of top operators and investors in SF/SV.

How to make the most of On Deck?

To make the most of On Deck, make time to attend all the events that On Deck organizes and then set up your own meetings with people in the community as well. Meeting people takes a lot of time and effort (especially if you’re an introvert like me), so try to join On Deck when you have a light schedule at work and no big vacations during the program. 

In addition to the big group dinners and smaller group discussions, I set up one-on-one meetings on the On Deck Hack Days where we all worked out of a coworking space. This was important to do because it helps to create a memorable connection with people you vibe with.

Regardless of whether you are on the East coast, West coast, or elsewhere, leverage the global On Deck networks. I simply messaged people on Slack or LinkedIn saying I was interested in getting to know them and to let me know if they were ever in SF. This led to many in person meetings and video calls.

On Deck has a Fellowship Hub where there is a directory of all the On Deck fellows and a list of all the partnership perks. The directory includes fellows’ contact information, social media profiles, what they’re working on, and what they’re interested in. You can always feel free to reach out to a fellow On Decker yourself, or can request an introduction to be made by the On Deck team. Remember to update your information if anything changes! I recommend using these resources to the fullest while you’re in On Deck and remembering they exist even after your cohort is over. 


What happens after On Deck?

The people I met are still my friends after On Deck. The Slack group continues to be active. You still have access to all the perks. There are events that alumni are also invited to.

After On Deck, I went through the On Deck directory, found in the Fellowship Hub, and sent a personalized connection request to all 197 people on LinkedIn over a period of a few weeks. I said I’d love to keep in touch and that they were welcome to reach out if they ever needed help with artificial intelligence or anything else even if our cohort of On Deck was officially over. I was pleased by the number of people who responded warmly. There were so many people that replied that they were interested in getting coffee to catch up, that I decided to organize a weekly small group brunch of rotating groups of people.

Even after I connected with people over social media, I still continue to communicate with other On Deck fellows in my cohort and previous cohorts on our Slack group. I know you’re probably thinking, “Oh no, not another Slack group”. This one is special. It's an incredibly active and engaged online community where past and present fellows are constantly helping each other. People form close connections on Slack. This is not a community where people only post random messages in public channels.

I’m planning to stay involved by hosting an event about artificial intelligence for the next cohort that I hope to see you at. I also hope to meet up with the NYC ODF crew whenever I visit next.


What opportunities did we get out of the On Deck Fellowship? 

I had many opportunities to join a startup as a cofounder or early engineer. I didn’t end up taking any of these offers because I wanted to work on my own ideas.  As I was doing this, I was able to get feedback on my own product ideas, designs, and demos faster. Even though I was working solo, many others in the program were able to find co-founders and early employees. I think more lucrative opportunities will continue to arise from my experience being an On Deck fellow.

Outside of job opportunities and my personal project, the On Deck community was willing to help with anything and everything. People who had experience being accepted to Y Combinator in the past were willing to look over my application and prep me for interviews. There was even a slack channel dedicated for pitch deck feedback. Rebecca Grubman was exploring launching a company to address mental health challenges around relationships, family planning and fertility and offered On Deckers free life coaching sessions around these difficult topics as part of her customer discovery.  Mark Alexander, another On Decker, offered free executive coaching to On Deckers.  People are willing to share each other’s work on social media to amplify reach. The fact that fellows were willing to help with things related to work and personal life shows how caring this group is.


Is the cost worth it?

One of the best parts of On Deck was the kickoff retreat when we all ventured out of the city for an overnight trip deep in nature among the towering redwoods and winding rivers north of San Francisco. There, we went on a hike, had rap battles, roasted marshmallows, and played board games. Unfortunately, many good things in life cost money. The fee associated with the fellowship covers this kickoff retreat, many weekday dinners during On Deck, and many lunches as well during hack days at various coworking spaces around SF. The next cohort will include coworking at On Deck’s new dedicated office for fellows to work out of during the 8 weeks.

On Deck creates a community of entrepreneurial individuals that push one another to be their best with a support system of experts, investors, and discounted tools useful for starting a company. Since you don’t need to give up any equity unlike accelerators like Y Combinator, paying cash upfront can be a much better deal. There are all sorts of perks from AWS, Stripe, Carta, and more, with a value of over $50k in credits.

If the price of On Deck is prohibitive, then I encourage you to apply to their scholarship program. I was lucky to be one of the partial scholarship recipients and am grateful for them offering this. There are a few fully paid scholarships available for the third cohort starting in March, funded by the generosity of previous On Deck Fellows and partners. 


How to apply and get accepted?

The application process is rolling. It asks for personal information, bio, what you’re looking to do next, and why you want to join On Deck. After applying online, you could be selected to do an interview. My interview was with Andrew Ng, a Senior Associate at SignalFire. Our conversation was super interesting and felt more like a conversation than an interview. My advice for the application and interview is to show you’re passionate about exploring new ideas. It’s okay if you don’t know what specifically you want to do, but it helps if you show that you have a few interests that you’re planning on exploring. If you know someone that did On Deck, ask them for a referral because there are special referral links you can apply through.


Just do it!

It’s for these reasons, and my great experience that I encourage you to apply to the fellowship.

I sincerely believe this fellowship had a positive impact on my life, and I would like to share that with others. 

Oftentimes, you have to be a part of the ingroup that hears about communities like this. The purpose of my article is to share it with people far and wide because it’s the diversity and balance between curation and randomness that made our discussions so enjoyable. If you’re interested in applying, feel free to reach out to me on Twitter or LinkedIn,  and I’ll be happy to help.