On Joining a Seed Startup & Overcoming Dementors

Just a note that I’ve intentionally avoided specifics about the company I work at in an effort to make this as universally applicable as possible. I’m planning on publishing another post in a couple weeks to dig into why I specifically chose the company I did. Stay tuned!

A few months back, I quit my job to join a company that wasn’t even really a company yet. At the time, it was just two people pursuing an idea.

To many people, it seemed a bit crazy that I was leaving my job to join a non-existent company  (and they told me as much). Especially as the job I was leaving was at a very real company, one which was providing me with a good salary and my visa to live and work in the UK.  So, I wanted to take this opportunity to write out my internal rationalization for the choices I made, and why I continue to think I made the right choice.  Joining a seed stage company can be daunting, especially pre-funding. If my thoughts can help even a single person figure out what’s right for them, then writing this will have been worth it.

For me the decision boiled down to a few opportunities that I felt were unique to working at an early stage startup: 

• The opportunity to spark my creativity by building something truly new.
• The opportunity to work with a team that inspires me.
• The opportunity to truly share in the upside of a business.

But before I get into all that, I need to talk about why I left my previous job. And to explain that, I need to go back to Harry Potter.

On dementors & deciding to leave

Every few years, I ritualistically work my way back through the Harry Potter series. I am currently engaged in said re-reading ritual (triwizard tournament is underway).  At the time I was considering my next steps, I was midway through the 3rd book. For those familiar with the books, I had reached the scene where Harry is practicing the Patronus charm, and he asks Professor Lupin about the Dementor’s kiss (when your soul is sucked out of your body).  Lupin tells Harry, “You can exist without your soul, you know, as long as your brain and heart are still working. But you’ll have no sense of self anymore, no memory, no... anything. There’s no chance at all of recovery. You’ll just — exist. As an empty shell. And your soul is gone forever…  lost.” 

At the risk of being a bit melodramatic, when I read that line it was an awfully apt description for how I had been feeling at work. My brain and heart were still working. I was still going to meetings and doing work everyday, but I felt nothing; no joy, no anger, just an empty existence. I came to the conclusion that my job had performed the corporate equivalent of the dementor’s kiss, sucking my creative spirit out of my work.

To be fair to my ex-employer, it wasn’t really their fault. My time at the company had been one of the most spectacular experiences of my life. The people I got to work with were incredible, and the pace of personal and company growth had been dizzying.  But as often happens, the company got bigger, ownership got diluted, and it no longer felt like I was building anything. It felt like momentum was just carrying us along. Perhaps the simple truth was that after 5.5 years, I’d done everything I wanted to do, and my excitement had dimmed.  That’s when I knew it was time to move on.

On the opportunity to build

Call it burnout, call it creative malaise; one of my top priorities in finding a new job was to find something that would rebirth my passion and creativity. That’s why before I began searching, I did some reflecting on what was important to me, and worth spending my time on.  This section is probably the most personal, and therefore the least universally applicable.  All I would say is to give some real thought to what excites you. For me it was my belief in the value of building, and my excitement to get back to being a builder.

I believe very strongly that as people we have an obligation to build things that are useful, beautiful, and ideally both. Those who came before us worked to build the world we live in, and we owe it to those who come after us to continue building and making progress. The speed of our progress is largely a function of the tools we are able to put in the hands of the world’s best builders.  The more powerful the tools, the more they can express the fullness of their creativity, and the further they are able to push the boundary of what’s possible.  To me, there is no higher mission than building beautiful, useful tools. If you are successful, your impact is amplified by all the builders who go on to use it to change the world.

That’s why when I started my search, I prioritized jobs focused on building.  I reached out to people building tools, and was energized by the conversation I had.  I saw a huge opportunity to make a positive contribution to the world’s builders, and most importantly, joining a startup meant an opportunity for me myself to get back to building! Build a new tool, build a culture, build a company.  I’m now building for the builders, and I couldn’t be happier.

On the opportunity to work with a great team

Before I started university, my dad told me to pick my classes to have the best professors and not to worry as much about the course material.  The insight was that the best professors can use even the dullest material as a medium to inspire, and instruct you.  I think this is possibly the best advice I ever received. It was hugely valuable in making my college classes enjoyable, and it has been even more invaluable in building my career.  This advice was also at the heart of my decision to join a startup.

It was my experience that an overwhelming number of the people I had most respected, and enjoyed working with had gone on to join/found new startups. It’s a cliche, but it’s true; startups have a habit of attracting interesting, bright, passionate people to them. That’s why when I decided it was time for a change, early startups seemed like the best place to go.  I wanted to be surrounded by people I admired and inspired me to do my best work. I therefore went looking for a team that excited me.

In my case, I was fortunate enough to have previously worked with one of the co-founders of the company I ended up joining. I knew that the work I had done with the co-founder at a previous job was some of the best I’d done in my career, and so I had confidence that the team would bring out my best.

However, before I decided to join I had the opportunity to interview with several early startups. In the usual case where you don’t know the team, my advice is to spend as much time with them as possible. Put real thought into what questions you want to ask during the interview process.  Ask them for extra time to talk, and meet them in-person (even though it’s 2022) if possible.  Go so far as to ask them if you can work with them for a week to get a feel for the team. They may say no, but it never hurts to ask.  More than anything else, team determines success. Also, odds are you are going to be spending a lot of time with them the next few years, so you definitely want to like them. Being part of a great team has the potential to bring out the best in your work and indeed yourself.

On the opportunity for Growth

To me growth has two sides to it, personal (the acquisition of skills & knowledge), and financial (the acquisition of wealth).  It has always been acknowledged that joining an early stage startup optimizes your personal growth.  On such a small team, it is inevitable that you will have disproportionate ownership over the direction of the product and company.  Assuming the team is good, you will also be constantly exposed to amazing people who bring out the best in yourself. The combination of the two results in learning more than you ever could in a role at a larger company.  

Of course, as was mentioned,  personal growth is only half the equation. Financial upside definitely matters.  That’s where people have typically seen joining an early stage as either being a compromise or too big a risk.  I’m not going to argue there isn’t any financial risk with joining a startup, that would be silly.  However I do think the common conceptions that pay is low, and any wealth you build will be illiquid are exaggerated.  If the team is good, and the business opportunity exists, it’s probably not as risky as you think.  For a detailed numerical analysis, see this article.

As we enter an economic downturn, there is a natural human urge to pull up the drawbridge and retreat towards the ‘safe’ options.   However, I think the recent downturn in the market only makes the proposition of an early-stage startup more attractive.  Many employees at big tech companies will have seen the value of their equity packages (granted during the peak of the bull run) evaporate over the last few weeks. There is less incentive to stay at the safe companies as there was several weeks ago.  Meanwhile, the advantage of joining a later-stage startup (Series B+), fast liquidity, has been diminished as many push back their timeline for IPO.  

Early stage startups now represent a great opportunity for achieving both personal, and financial goals.  Coming off the strength of the last 2 years’ bull market, many early-stage startups are flush with cash. If they have raised recently, and are managed judiciously, they should have enough runway to weather a few years of a tough economic environment.

On taking the leap

Even after finding opportunities that I was really excited about, there was the final step - actually making the leap into the great unknown.  Now, I’m cognizant that everyone has unique circumstances and experiences which will come into play when making such a big decision. There’s no one size fits all approach, and this is again where individual philosophy becomes important. That’s because, no matter how much time you spend analyzing the decision, the reality is that there is still uncertainty and risk.

My personal philosophy is that when opportunities come along, you should bias to say yes.  As I went through the above, I do my best to qualify the people, the idea, and the growth.  After that, to deal with the remaining uncertainty, I’ve found that the duck test works well: if it sounds like a good opportunity, and walks like a good opportunity, then it probably is a good opportunity. 

I’m not being flippant, but there’s always risk when making the decision to pursue something new. I just try to remember that, to a large degree, the importance of ‘big’ decisions is an illusion.  It’s actually the thousands of subsequent actions that come after ‘the decision’, which retroactively determine whether it was good or not.  Energy is usually better spent working to make your decision a good one, than agonizing to get clarity on something inherently unclear.  

In my case, since I made the decision to join the startup, our energies have started to bear fruit.  3 months since coming on, our work has helped us secure funding from a prominent Silicon Valley VC fund, begin our initial user testing, and start to put together a great team.  Of course, I’m under no illusions that the success of the business is guaranteed. So far so good, but it’s day 1 of what promises to be a long but rewarding journey.  

And I am happy to report that one of my personal goals has already been achieved. Being able to sit down everyday with an opportunity to build, I’ve felt my creative spirit come back to life.  Thankfully unlike the dementor’s kiss, if you lose your creative spirit to your work, recovery is possible, all it takes is the right team and the right dream.

I hope that sharing this experience helps others get comfortable with taking the leap.

Some of the articles which were influential in my decision making: 

• Why you should join a startup
• Managing career risk in startups
• Paul Graham on wealth