Three and a half months ago, I wrote about why I wanted to be On Deck ahead of my call with On Deck’s Head of Candidates.

I want to join the On Deck Founders Fellowship and be a part of a modern education institution for the future of work. That future, for me, is working and collaborating on interesting problems I’m curious about with other intelligent people. All the while, providing feedback, offering perspectives, and giving back to the network.

I applied to the On Deck Founders Fellowship (ODF) with ambitions to either launch Blynd, my food ordering startup, or join someone else’s startup. My reason for applying though ran much deeper than just working for a startup. For me, it was about developing meaningful relationships with other ambitious people that last long after the fellowship. I am happy to report that I think I succeeded, but not in the way I first thought. I made a lot of mistakes along the way, that hopefully can serve as an example for future fellows.

Mistakes Launching a Startup

Mistake #1: setting out to (only) build a startup

It didn’t take long to get to the first mistake. I skipped step 0. I had an idea and started to build it. I didn’t take the time to understand my customers, their problems, and validate the idea. Instead of starting a startup, I was merely building a software product. There was no ongoing communication channel, I didn’t “work with the garage door open”, I just built it. But they didn’t come. The value proposition was untested with the target customers.

Mistake #2: building in private (without product-market fit)

As an engineer, it’s fairly trivial to build out an MVP for a food ordering platform. It was a simple Progressive Web App (PWA) built with Django (a Python web framework). I hooked it up with PayPal, Stripe, and the Google Maps API. I was ready to go, but no one wanted it. I hadn’t spent the time to build a community around the product. Restaurants weren’t champing at the bit to use it. They didn’t even know about it and had no way to find out.

Mistake #3: Not having founder-market fit (and being unable to recruit someone)

I consider myself a foodie, but I have no rapport in the food or hospitality industry. Sure I worked at restaurants, country clubs, and Starbucks when I was younger, but I had no way to get Chicago restaurants interested in this unknown product. So I tried to recruit. I got in contact with my favorite local influencer. I was sure that she was the missing piece of the puzzle. Alas, she didn’t have the bandwidth to take on another project and the other influencers never got back to me. Most successful founding teams need someone who is a subject matter expert or at least has a proper network to leverage.

Mistake #4: trying to launch a food ordering platform during a global pandemic

Restaurants in Chicago are still struggling. In my head, Blynd was a great solution for these restaurants. Blynd gives restaurants a unique way to engage with their following through their socials, has an in-person community around it, and has favorable economics compared to the existing solutions like DoorDash. From their perspective, however, restaurants are suffering from app-fatigue (serving orders through DoorDash, UberEats, GrubHub, etc.), have condensed hours to save on labor costs, and lack the bandwidth to support an unfound company with no users.

Mistake #5: Incorporating before having customers

At the end I got desperate. I incorporated Blynd as a C-corporation with Stripe Atlas and used Mercury as my banking solution so that I could hook up ACH payouts to restaurants instead of PayPal (a must from restaurants). I even started offering influencers equity to become advisors and restaurants equity to come on as a pilot restaurant. This is the most costly mistake as I paid to incorporate the company as well as pay to unincorporate the company. The silver lining being that the unincorporation process was very clean since I never did any business and no one took me up on my offers.

Moving on from Blynd

After all of that, I decided to shelve Blynd for the time being. Born out of the pandemic, I wanted to build a solution for restaurants that were being charged insane fees from companies like DoorDash and GrubHub. Combine that with solving the decision fatigue my girlfriend and I faced weekly decided where to order dinner from. Good idea, so-so execution, no users. I didn’t fully understand what it took to acquire users or really start a company.

I still love the concept. In fact a neighborhood favorite of mine that I reached out to, Tortello, has a meal on DoorDash that embodies what I was really trying to do with Blynd.

I think once the technology is more mature, there is a great web3 play for Blynd that can help restaurants capture substantial value from their regulars with the help of NFTs.

Cofounder Dating in On Deck

After “failing fast” with Blynd, I wanted to maximize the rest of my time in the fellowship to meet with other founders. Specifically those who were looking for technical cofounders. I focused my time into my areas of interest and core competencies (learning from my mistakes with Blynd). I was most interested in joining companies working in web3, finance, health, and travel.

I was overwhelmed by the talent pool that On Deck offers. There’s so many brilliant people from diverse backgrounds who are building amazing companies. The whole process was exhausting, but in a good way.

After a number of insightful conversations, I matched with a few very bright founders. We set up a “try before you buy” trial period where I contributed to each of the projects to get a sense of what working there would be like should I choose to stay. This is beneficial for both the founder and myself since we each get to “test drive” each other as part of an informal interview process. It also gives me time to better align with the product, the technology, the people, as well as the workflow. Formally, these engagements were contract work. Some paid me and others did not.

Taking a step back

After doing this for a few months, I’ve decided to take a step back from my contracting work and cofounder dating. While I enjoyed my time working directly with brilliant founders, I struggled to find the right fit. Some were conflicts of interest with my current full-time role, others were looking for someone with more experience, but at the end of it all, I felt really drained. So much so that I had to take a week off of from my full-time job to get my mental and physical health back on track.

I’m unable put my finger on exactly why it didn’t work out, but I found that building someone else’s startup I wasn’t fully aligned with after programming all day at work was especially taxing on my energy. Pair that with the lack of ownership and not needing another contracting salary. It’s time for something new.

So What’s Next?

I’m rethinking and honing my thesis on what a career means for me. It considers three aspects that I find most promising. Each come with their own tradeoffs, but each offer their own unique upside and area for development.

1. Firm
2. Ventures
3. Content

Working for a Firm

The firm is where I work full-time. Right now it’s at a hedge fund where I am a full-stack software engineer. Here I’m focusing on growing my skills (both in finance and tech), becoming more senior/leading a team, and building out an engineering organization at scale. It’s not the right time for me to leave. I am helping build a new-grad program from the ground up and just spent the Fall helping recruit an internship class.

There’s tremendous upside to working for a firm. These include the security of a salary, health benefits, and in-person camaraderie especially in the remote world. Not to mention building something that is greater than yourself. My favorite part of working for an investment firm though is that there are clearly aligned incentives: generating returns for investors.

I’m especially fascinated by firms who manage money, generate returns for their investors, do great research (in the open), and have great community engagement. Some firms doing especially great work here are Jump Trading and Paradigm.

Building Ventures

The second pillar of my career are ventures. Ventures are what I build and own on the internet. This is what excites me so much about web3: people building projects, protocols and networks in the open. This space is new and growing rapidly. I’m focused on spending time

• Working with DAOs (am a part of Developer DAO)
• Shipping projects/dapps that are uniquely interesting to me (stay tuned!)
• Contributing to open-source projects

I have a few things in mind, but will be focusing my efforts on getting better at Rust, Solidity, and modern JavaScript/TypeScript.

Creating Content

The final pillar of my career is becoming a creator. Being a creator is the most high leverage thing anyone can do right now. The idea that anyone can create whatever they want and everyone can find whatever they’re interested in is incredibly powerful. Especially with the rise of web3, you can amass consumer attention at scale, create something that can capture attention, tell powerful stories all while owning the end-to-end channel. Building and fostering a community is an invaluable skill. One that builds rapport with an audience and one that would have been helpful while building Blynd.

I want to push myself to continue to be creative, but I feel especially new at this one. I used to be a small-time YouTuber back in 2010. I made mostly Call of Duty and Minecraft videos and I had a few thousand subscribers, but ended up deleting my presence because people I knew found it and I was mocked because of it. That led to me finding social media very toxic and instead gravitating towards having a minimal online presence. This was a huge mistake (partly). On one hand, I was consuming mindfully, but on another I was stagnant and not pushing myself.

Going forward, I want to create content that is unique to me and my interests. Right now, I’m especially interested in crypto, health data, and content creation. I find Twitter and TikTok to be my preferred content aggregators, but am also thinking about other formats like podcasting, newsletter, and starting a DAO.

Still early days here, but I’m optimizing for learning, building, and experimenting. Opportunities will come when the student is ready, but for now, I’m still on deck