Building with Jacob: My Week with On Deck

Week of 2023-11-06

Welcome back to the "Building with Jacob" series, a weekly update on my journey and experiences building Push Training. This past week was fully dedicated to the On Deck fellowship. In On Deck's words, "On Deck is a one-week, in-person sprint where a hundred talented founders figure out what company to build, and with whom. After the program we’ll onboard you to our online network of 2,000+ founders that combines software, support and IRL events to help you build early product momentum, get distribution, and raise capital."

First Day at On Deck: Expectations vs. Reality

I went into On Deck with one simple expectation: to connect with like-minded individuals in real life, and On Deck well exceeded that expectation.

Each day, about 80 people gathered, each optimistic about the future yet each understanding that 90% of their ventures would never turn a profit. This is a unique type of person, and while one may argue that the SF Bay Area is full of these types of people, they are not always identifiable and in a place that fosters connection and collaboration. The team at On Deck did an excellent job vetting and bringing together these people from all parts of the world.

Sessions That Changed My Perspective

Two sessions stood out for their impact on my thinking.

The first was led by Peter Walker, Head of Insights at Carta. It was a data-driven deep dive into equity splits, challenging the common advice of equal equity splits. This was incredibly insightful as we reviewed real equity split data from Carta’s platform. The biggest surprise was that the majority of multi-founder teams do not have equal equity splits, contrary to the advice given by many in the startup community.

The second session was led by Julian Weisser, co-founder of On Deck. In the session, Julian was able to share a real glimpse into both the ups and downs of co-founding On Deck which shifted my perspective on the expectations between investors and founders. It was also inspiring to hear from a startup leader who didn’t hesitate to share the imperfect moments in their company’s journey.

Product Feedback from The People of On Deck

I met so many fascinating people in different stages of their entrepreneurial journey, some still full-time employed, some secretly working on their next thing, some exploring new ideas, and some already with shipped products and revenue. Even though the majority were focused on B2B SaaS with LLMs somewhere in the mix, I didn’t feel out of place talking about Push Training and consumer fitness. Everyone was eager to provide feedback, poke holes in the strategy, connect me with others, and even try the product itself.

Part of being a founder is hearing a lot of ideas from a lot of different people, and often times the advice from one contradicts advice given by someone else. But when I hear the same piece of feedback from different people, I usually take it as a stronger signal to dive deeper. As I chatted with the On Deck cohort, one of the biggest recurring pieces of feedback I got was around Push Training’s in-app experience directly after onboarding. Users are met with a page full of text and are guided to view a 3-minute example workout. The feedback given suggested directing the user straight into the example workout or their first real workout, depending on whether they were ready to hop on a treadmill or not.

Post-On Deck

As a result of my experience from the On Deck fellowship, I'll be giving more thought to Push Training’s distribution through strategic partnerships. This direction came from a conversation with a fellow founder, Campbell Pritchard, in the final hours of the program as he talked about distribution methods I hadn’t yet considered. (I’ll also highlight that Campbell introduced me to someone in the fitness industry—another great example of the helpfulness of those I met from On Deck.)

Overall, the program has provided a community where we can learn from and help each other, further equipping individuals like myself to pursue whatever lies ahead. I'm eager to share more updates and insights with you, so please reach out with any questions about the On Deck fellowship and subscribe for more updates on Push Training's progress.

P.S. We got to experience a sunset harbor cruise out and around the Golden Gate Bridge which was truly unforgettable!