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The On Deck (ODF5) Journey

Since we’re almost two weeks into the fellowship, this post will cover the time between acceptance and the end of the second week.  Check back for follow ups and I’ll probably do a final “synopsis” post at the end. Thanks for the support and I hope this helps someone!

(I’ve been advised to put an intro here. It will show up by tomorrow)

“Should we do On Deck?”

We learned about On Deck back in May of 2020.  Alex and I were interviewing with accelerators to help take Deft to the next level and break free from our 9-5’s. It was a hectic couple of weeks. COVID is in full swing, Alex just had a baby, and we’re juggling the demand for our product with stressful accelerator calls & demos. As the interviews dragged on, we started to come to our own conclusions about what we wanted over the next 6 months.  Accelerators can provide a ton of benefit in a short time (~3 months), but you want to make sure that you’re leveraging that time effectively for your startup.  In our case, we were still making monumental improvements to our text search and image search capabilities and weren’t ready to escape from the safe-space of closed beta.  We decided that using our time in an accelerator to go from 1 to 1,000 was probably a better use of the opportunity than going from 0 to 1.

Towards the end of one of the interview process(es), a good friend of mine gave me a call about On Deck.  He was working through a partnership deal and thought it would be a great fit for where Deft was. Their website read “Where top talent goes to explore what’s next”.  While we had a pretty good idea of what’s next for us, our curiosity was piqued by the tracks for explore vs. build.

I jumped to Twitter to check the sentiment.  Glowing reviews from #ODF1, #ODF2, #ODF3 participants and some amazing companies evolving from the program. I went back to the apply page.  The applications were due in 4 days…..

Applying to be On Deck

I could feel the dread bubbling within me.  For those who have applied to an accelerator before, you know how long an application can take. Either Mark Twain or Blaise Pascal is credited for saying “If I had more time, I would have written a shorter letter.”   A lot of these applications require 250 words or less for every answer. While I generally believe this constraint is helpful, both for the readers of 1,000’s of applications and startup founders who need to think more deeply about what they’re solving, it certainly makes applying in 4 days challenging.

We got to work over the weekend, but were relieved to find this wasn’t your standard accelerator application. The questions focused more on the founders and our aspirations than intricate parts of what we were building.  Our perception of On Deck started to change.  From an accelerator for our business to more of a community of like-minded individuals focused on making things.   On Deck felt like one of the new “startup communities” that were popping up.  It seemed similar to which we were already participants of.  However, we reasoned that a larger network is almost always a net positive.

Blank Paper and Pencil
Photo by Kelly Sikkema / Unsplash

The rise of idea-stage communities

If you’re just looking for the On Deck experience, skip over this.  I want to elaborate briefly on this trend to give someone a frame of reference if they’ve already joined a startup community.

Over the past few years, I’ve watched and participated in the rise of a number of startup communities.  Indiehackers,, Startup Grind to name a few. They cater to founders with different goals, but ultimately are solving the same problem. The problem is that the road to building a successful startup is lonely, testing, and rife with failure. To put a number on it, something like 90% of new startups fail and 75% of venture-backed startups. These communities are bringing like-minded individuals together so that collectively they can be more successful. The idea is that when you join, you’ll immediately have access to groups of willing user testers, businesses to sell your new products, introductions to people you need to speak with, etc.

Prior to this, accelerators were the golden ticket to having a startup community around you, but at the cost of a chunk of equity. That always felt like a reasonable trade-off, but over the past 5 years their selections have skewed towards later and later stage companies. From our own experience in those interviews, it doesn’t feel like the founder + founder-idea fit takes precedence any longer.  Instead, it’s been replaced by how much traction you have to de-risk their investment. I believe that this change, along with an increase in the number of startups applying, have opened the door for startup communities to capture the attention of earlier stage companies. Accelerators seem to have realized their mistake and are quickly trying to cross the divide, but they haven’t hit the mark.

Personally, the experience we’ve had in On Deck in two weeks has been worlds better than months at other programs I’ve tried.  The only other I would compare it to is Pioneer. To do a quick comparison, Pioneer has a very global reach while On Deck still feels a bit more centralized in the US (it is expanding though). In addition, On Deck’s curriculum is more intensive, so if you’d like more startup education, that’s the place to go.  However, both are incredibly valuable and I’d recommend both to anyone in a heartbeat.  

Photo by Daniel McCullough / Unsplash

Interviewing for On Deck

So, we applied within the 4 remaining days and anxiously awaited a response. Compared to the normal accelerator application, the whole process was much more streamlined. Alex and I both received an email soon after for an interview. Since the applications are individual, we were thrilled that we might have a chance to be in the fellowship together. We did some preparation and used the questions from the On Deck application to guide us. Our focus was on questions like: what did we really want out of the fellowship, how could we give back to the group, and why would we be a good fit.  

Our interview day came and aside from maybe talking a bit too fast, we both felt we did our best and got the point across. Fast forward a few more days and we both got our acceptances around the same time. After having re-evaluated what we wanted and feeling a bit bummed about stepping away from accelerators, this was a much-needed success.  Now we only needed to wait a few months for it to start….

The first and second week

I am certain people have already covered what it feels like when you start, but in one word: whirlwind.  There’s a bit of build up, then a kickoff and then you’re launched into the program like a cannonball. Community events, 1-1s, core curriculum, icebreakers, and socials are thrown at you faster than you can click “yes” on your calendar. It’s quite overwhelming, but honestly, I wouldn’t have it any other way.  You can feel the energy pouring through your screen, zipping up the wires of infrastructure that power Slack and Zoom. Given that we’re going through this during quarantine, everything has been fully remote, but I’ve got to say the On Deck team has done such an amazing job at making it just as good as in-person. On Deck has created Silicon Valley in the cloud.

The first and second week have focused a lot on the early stages of a idea. Namely, setting new founders up for success in the co-founder search and navigating the first steps of a product’s journey (ideating, validating, etc.). However, that doesn’t mean it hasn’t been valuable for those further along like we are with Deft. The instruction has helped us reconsider some of our own decisions and will certainly inform us with future endeavors. In addition, there has been a multitude of fundraising chats, perks, and advice have kept us running full speed ahead.

Pomeranian working on an iPad
Photo by Cookie the Pom / Unsplash

Learnings so far

Without going into too much detail on the programming and spoiling things, let me go through the intrinsic benefits I’m reaping from On Deck.  

  1. You’re not in it alone

    When I joined the Slack, I immediately felt a sense of relief. “Wow, there are really 1000+ people all around me going through the same things I’m going through”. It feels like even if you fail, you’ll instantly have a place to get back on your feet and try again.  

    Traditionally, startups have been an isolated experience.  You toil away day after day in a vacuum.  You finally get to a stage where you put it out into the world and…….crickets.  No one jumping up to help you figure out where you went wrong, no one to celebrate the small wins, nothing.  On Deck solves that. Everyday you hear and see people doing the same things.  Which leads me to my next learning from On Deck.

  2. Others have been where you are

    Trying to figure out your go-to-market? Yup, someone just got their first big customers.  Trying to fundraise? 2 people closed their seed round today.  Trying to figure out if your idea is worth it?  People in your market are ready to give feedback.

    With this many fellows, there is a high percentage chance that someone in this community has done it before and is willing to help. It’s like having access almost 24 hours a day to Napoleon Hill’s entire lifetime of interviewees. The best part is, On Deck has created a directory to sort and quickly access the exact right people for the problem you’re facing.  It’s about as close as you’ll get to having the answers to the startup test.

  3. Curing your imposter syndrome

    This a bit of a misnomer, as I think it’ll be difficult to cure it permanently, but being in On Deck has dampened (and will certainly continue to dampen) my imposter syndrome. As a bit of background, I’m not cut from the Forbes 30 Under 30 cloth.  I grew up in South Carolina.  I had modest grades at a public high school.  I went to a public state college because my mom said “You can go out of a state and pay loans for $40,000 a year or you can stay in state and pay $9,000”.  Who was I kidding, I didn’t have the grades to get into a school that would make out of state worth it. In college, I didn’t do anything to stand out other than make the dean’s list here and there.  My degree was in economics. Partly because it seemed a reasonable degree to get a reasonable job and partly because I had changed majors so many times I was worried about racking up more loans for a 5th year (which I ended up doing anyways). My first job out of college was in finance working as a stock broker.  I hated it.

    The realization that I might spend the rest of my life on this terrible career path woke me up in under a year. I wish I hadn’t been dragging my feet through life for the other 22.  I rekindled my love for computers and childhood web tinkering to teach myself modern day web programming.  Given the competition for tech jobs, I knew the only way for someone with my background to get an edge was to work harder. I got decent and applied to one of the only reputable tech companies in South Carolina.  I got the job which gave me my first win.  From there I kept trying things online, including my first business.  It did well and then I decided to shoot for a loftier business idea.  I moved out to San Francisco to pursue it, sleeping on a friend’s floor until I could find a place to move into.  It failed, but I learned resilience. I got a bigger product role there and then kept working and studying, making incremental improvements.

    I’ll stop there because it’s closer to present day and I’m taking forever to get to the point, but you can see that I’m not some cream of the crop.  In On Deck, like many other things I’ve qualified for since leaving that finance job, I was terrified.  I thought to myself there was no way was I going to fit in and be able to give value to these extraordinary people.

    But, this is what I love about the startup world. If you persevere and work hard and then create something wonderful, it doesn’t matter your background. The product speaks for itself. On Deck is no different.  Yes, there are a large number of very accomplished people here, but it’s not about your background.  It’s about the effort you put in to contribute so that everyone can make something wonderful.    

  4. What goes around comes around

    The final point was encapsulated in the previous sentence, but I’ll give some specific examples.  On Deck, like other startup communities, is not something you can come into and sit back.  You get out what you put in.  There’s a great post about it here.

    In the first two weeks, I’ve hopped on tons of 1-1s to give advice and support. That’s led me to doing deep dives on SEO to help an e-commerce product, connecting the founder of a new meal-delivery service with my personal network, and even building a landing page, mailing integration, and migrating servers in under 3 hours for someone who needed it urgently.  In return, I’ve gotten on-the-spot fundraising advice, pitch deck reviews, and even some $cash after having been part of one of the winning build weekend teams!

    This rule applies to life outside of On Deck, but it’s a valuable one and I’m not sure there’s a quicker way to learn it in the context of startups than 10 weeks with the On Deck program.


Well…not really because we still have 8 more weeks to go! I’ll report back closer to the end of week 4 and link the story here.

In terms of Deft, On Deck and its participants have helped introduce us to angels, we’ve been able to cut down on image search times significantly via some clever recommendations, and we launched our open beta!  This best part is that it’s only the beginning.

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