🧡 No silver bullets: 5 lessons from Y Combinator Winter 2022

Y Combinator is the most renowned startup accelerator in the world. It has backed companies including Reddit, AirBnB, DoorDash, and Dropbox. As the Summer 2022 batch of Y Combinator begins, I had some time to reflect on our own experience of going through Winter 2022. In this post, I jot down some thoughts about that experience, and some lessons learned along the way.

Some background

Workflow86 is a software platform that allows anyone to document, automate and manage their internal business processes. Workflow86 was founded in 2021 after observing how poorly most organizations store, manage and scale their most valuable asset: the internal knowledge and processes that are critical to their day to day operations and teams. We are on a mission to codify the 99% of operational knowledge and expertise held by non-technical teams, and translate this into massively scalable software. 

How Workflow86 got into YC

Y Combinator (YC) is the most renowned startup accelerator in the world. It has backed companies including Reddit, AirBnB, DoorDash, and Dropbox. Getting into YC is incredibly competitive. The acceptance rate hovers around 2-3% (compared to 5% for getting into Harvard University). The most likely outcome of applying to YC is not getting into YC. But the odds will always be stacked against you in the world of startups, so this should not detract from anyone giving it a shot. Getting into YC starts with a written application, with questions covering all the basic and fundamental facts about your startup. You write out your answers, record a 60 second video of yourself introducing your company, include a demo video if you can, and then click submit. Then you wait.

Workflow86 submitted its application to YC in September 2021. At that time, we had raised a little pre-seed money and firmly focused on building product. We were beginning talks with investors for a seed round some time in 2022, but reception was lukewarm. In November 2021, we did our Hacker News launch. A week or so later, out of the 18,000 applications that came in for the batch, Workflow86 was one of the companies that received the following email:

What followed was a frenzy of interview prep and mock-interviews with YC alumni. The day of the interview came, and I thought I completely bombed it. I spent the 24 hours after the interview so focused on telling everyone not to get their hopes up, that I completely missed this email:

After another frenzied period of calling up YC, I finally reached a partner and confirmed that Workflow86 was in. We were now a YC-backed company. It was all pretty surreal for a while, but it finally sunk in when we turned up on the Y Combinator company directory:

5 lessons from Winter 2022

Y Combinator Winter 2022 took place between January 2022 and March 2022. It was certainly an interesting time to have gone through YC. It appears that Winter 2022 will be the last fully remote batch. Winter 2022 was also one of the largest and most international batches ever, as well as the first batch to receive the new YC deal. In the 12 or so weeks of the batch, these were a few (of the many) lessons learned, many of which can be applied or replicated by startups regardless of whether you are doing YC or not.

1. Progress expands to fill the time allocated to it

Parkinson’s Law: work expands to fill the time allotted for its completion.

Simply put, Parkinson’s Law states that you allocate yourself X amount of time to achieve Y, then Y will expand to fill X. One way in which you can use this to your advantage is to constrain the amount of time you have to complete a task or milestone. This is one of the core themes of the YC batch. As soon as you get accepted into YC, a time has been allocated for you, between that very moment and demo day. This is about 12 weeks from the start of batch to demo day. This time constraint is used to apply pressure and get startups in the cohort to make as much progress as they possibly can in a set amount of time. Additional time constraints during the batch are also set by weekly meetings with your partners and section. The underlying idea is simple: speed equals time over distance. If you can cover the same amount of distance over a shorter period of time, you are moving faster. This is one feature of the YC batch that can be replicated by any startup – set a deadline or time constraint for a goal and then subtract an extra 20-50% to make that deadline even more ambitious. It is surprising how much you can get done by imposing some additional time pressure.

2. Disclose your symptoms – it is your well-being at stake

Throughout the start-journey, you will seek and get advice. During YC, the process of seeking and receiving advice occurs on a regular basis during weekly office hours with your group partners. Assuming you have trusted and experienced advisors, the critical factor in the quality of advice you receive is the amount of context and information you provide to them. The analogy here is that your YC partners are a lot like doctors – the quality of their advice depends on you providing them with as much information as you can about your problems and pain points. If you hide or distort the problems you are facing, there is a good chance that you will get misdiagnosed, and things may seem to be less serious than they actually are or more serious than they actually are. This in turn can lead to the wrong remedial actions being prescribed with little to no impact on the problems you face, or potentially even making them worse.

Being transparent with advisors with the state of your company should not be a difficult or uncomfortable thing to do. None the less, it is difficult and uncomfortable. I think much of this is driven by a sense that if problems are disclosed then your advisors will somehow look down upon you or lose faith in your ability to deliver. However, if you have surrounded yourself with trusted, high-quality advisors who are truly invested in your success, it is clear that they much prefer bad news than no news at all. Good advisors (and investors) know it is in their interest to help you detect problems early and prevent them from becoming  potentially fatal to your company. In turn, they should create an environment in which this is encouraged and any hesitation is actively dispelled. YC was pretty clear with this at the start. To paraphrase one partner:

We know your startups are fundamentally broken…we are not going to take our money back. We are here to help, but we can’t help unless you talk to us

Early detection means early prevention – something that applies as equally to your startup as it does to your own health and well-being. This ultimately starts with sharing as much context and information as you can with those who want to help.

3. Someone has been through it (and worse) and survived

Building a startup is one of the most difficult things you can do. As much as it has been glorified in popular culture, the early days are often full of uncertainty.

Running a startup is a lot like running a marathon blindfolded. It is long and exhausting, and you have no idea about whether you are running in the right direction, whether you are running fast enough and where the finish line actually is.

One issue that emerges from this state of uncertainty is the lack of context on the relative scale of the problems and challenges you are facing. In the absence of any clear solution, many problems can seem insurmountable or even fatal. One way YC remedied this was by surrounding you with other founders across a wide range of stages. The YC alumni network is expansive, encompassing everything from founders who have been there and scaled their company to IPO and beyond, to founders at the same stage and experiencing the very same problems as well. Beyond the knowledge and experience that comes with this community, one of the benefits of this diverse range of experience is simply the reassurance that someone has been through exactly what you are going through (and sometimes much worse) and survived. You can’t help but realize you are a lot more resilient than you think after hearing about the early days at companies like AirBnB and Coinbase. YC provides such a network of founders almost instantly, but this is a lesson that any startup can also apply. Simply put, it pays to network and connect with other founders across a range of different stages.

4. Knowing you are wrong is better than not knowing at all

“I have heard that haste can be folly, but have never seen delay that was wise.”

One of the bad habits developed from years as an academic or professional overachiever is an aversion to making mistakes. I’ve found this is particularly the case if you have come from professional services such as consulting or law. The problem is that aversion to making mistakes often means you will default to inaction over action in the face of uncertainty. As a startup, you have a set amount of time and energy to live. Inaction means you are treading water and slowly drowning, rather than furiously swimming towards the shore like you should be.

One of the big lessons from YC was that when faced with uncertainty, it was better to make an assumption and vigorously pursue that to a conclusion of success or failure, than it was to leave it as a hypothetical question. Simply put, knowing you are wrong is infinitely better than not knowing whether you are right or wrong at all. The overarching uncertainty for any early-stage startup is “are we building something that people want?”. The most obvious and clearest way to manifest action towards this question is to launch your product and put it in front of people. Launch it early, and launch it over and over again. Defaulting to action can be difficult because action often means confronting uncomfortable situations like users rejecting what you have built. There is a temptation here to indefinitely delay action so you can remain in the realm of possibilities rather than a reality of rejection. But again, all you are doing is treading water while slowly drowning. Defaulting to action is perhaps one of the most important reflexes you can develop and certainly one which I keep top of mind on a day to day basis.

5. There are no silver bullets, only lots of lead bullets

At the end of the batch, the YC partners said something really stood out to me. To paraphrase:

“Success doesn’t come from a single silver bullet, but from a massive amount of lead bullets thrown at your target”

I like the analogy of silver bullets vs lead bullets because it highlights that what underpins startup success is far less glamorous or dramatic as we would think or hope. Many may come into YC thinking that it is the “silver bullet” for their startup. The logic goes “If I get into YC, then I will succeed”. Even once you get into YC, it is easy to fall into this “silver bullet logic” of “if I do/achieve/get X then all of my problems will be solved”. Without a doubt, YC will increase your chances of success. It does so by providing you with access to an incredible wealth of startup resources and knowledge. It will also connect you with perhaps the best startup community in the world. It will also provide you with a massive “loan of credibility” that will make investors, customers, potential employees, and others take you more seriously simply because you are backed by YC. But it will not solve fundamental problems of your business for you, nor will it alleviate the painful and frustrating work that is inherent to building a startup. As YC reinforced over and over again, building a startup is hard, unforgiving, and painful – it is getting punched in the face everyday and getting up the next day to do it all over again. YC does not change that. Neither does raising money from famous investors, getting featured on TechCrunch or whatever singular event you might think will magically solve everything. YC is not the silver bullet you have been hoping for, but it is the stockpile of lead bullets you actually need to succeed. The emphasis remains on you to make the best use of those resources.

So, was YC worth it?

I get asked this question a lot. My response is an unequivocal yes. YC is not a silver bullet, but it did alter the trajectory of our company, launching us from an obscure startup quietly building away in the suburbs of Sydney, into the same room as some of the best founders, companies and investors in Silicon Valley (and the world). There is still a long and likely difficult journey ahead of us and more lessons to come, but there is also exciting news to announce as well. Until then, it is back to work.

P.S. we are hiring.