Going All-In

8 min read

It’s February 19, 2015, and I’ve just landed in Boston to be greeted by one of the biggest snowstorms ever recorded in the city. I’m there to meet with the leadership team at HubSpot before taking a role leading their new SEO team. I was running strategy at a marketing agency back in the UK at the time and had started working with a growing number of SaaS businesses that piqued my interest in what was becoming an increasingly fast-growing space.

While I’d been working with a lot of tech companies, I hadn’t worked at one before. This fact became glaringly obvious as I arrived at HubSpot HQ in a full suit. To say I felt overdressed would be an understatement. During my entire time at the company, I could probably count on one hand how many times I’ve seen anyone in a suit. As I walked through the beautifully designed office, laden with free snacks, beer taps, ping pong tables, games consoles, and of course, a nap room, I began wondering if this was a workplace at all. It was very new to me and was a million miles away from what I was used to.

After a full day of interviews with the team, it became clear to me that behind all of the office gimmicks there was an incredibly talented and driven team of leaders that I would be very lucky to get the opportunity to learn from. At this point in my career, I wanted to level up my leadership skills and get the opportunity to build a substantial team that could eventually lead to me becoming an exec. This was clearly going to take time, but I knew that I could absorb a ton of knowledge from the existing team at HubSpot and if a few other things fell in place I’d get the chance to take an accelerated path to my goal.

I flew back to the UK, spoke with my wife, and signed the contract with HubSpot the following week. It’s hands-down the greatest career decision I’ve made to date and has changed my life both personally and professionally.

From 600 to 6,000

I joined only a few months after we’d gone through our IPO, and with a little over 650 employees, the company was valued at ~$900 million. Fast forward to today and HubSpot has over 6,000 employees and a market cap of over $20 billion. Going through this level of growth has been a wild ride, and I’d love to say that when I joined I envisioned this all playing out, but the reality is that I was just excited to join a high-performing team that was willing to invest in me. Anything beyond that was a bonus. Needless to say, it was quite the bonus.

When you go through this kind of growth, a company needs to shed its skin several times. Processes, structure, culture – they all need to evolve. One thing that has surprised me the most over the years is that while we’ve had many people come and go, reorganizations of the team structure, a meteoric global office expansion, and then an equally meteoric shift to remote work, the core values set out by the founding team have persisted. I’ve no doubt that this is one of the primary reasons why the company has consistently been voted as one of the best places to work year after year. This relentless focus on being a value-driven company is something I’ll take with me for the rest of my career.

It’s worth calling out that I’d never planned to stay at HubSpot for 7 years. If you’d have told me that I’d be there this long when I first joined I would have laughed at you. In fairness, I was in my mid-20s so I wasn’t looking further ahead than a year at a time. There are many reasons behind my decision to stay this long, but one of these was by far and away the largest contributor: the company has consistently invested in my personal growth.

Having a company invest in you in the way that HubSpot has invested in me is incredibly rare. I’ll be eternally grateful for this. It gave me the privilege of living in three different countries (going above and beyond to help with my relocations), promoting me all the way from being an individual contributor up to eventually becoming a VP, and trusting me to run a team of ~80 people. I’ve worked alongside some of the greatest minds in the world, some of whom have opened doors to me that I’d never thought would be possible, and many of whom have become life-long friends.

For all of this and so much more, I’m incredibly thankful.

But now, it’s time for something new.

The Future of the Web

Anyone that’s had an extended conversation with me over the past half-decade has likely heard me talking about blockchain technology. The boom of 2017 brought a lot of attention to the wider crypto space, and while a lot of it wasn’t good attention, it validated for me that crypto was here to stay. More importantly, we were at the precipice of the next phase of the web. There was a lot of work to do.

I began immersing myself in the crypto community, reading countless books, attending every event I could, speaking to founders, investing in projects, and offering free marketing support to a few different foundations.

By mid-2017 I was hooked.

I started the Decrypting Crypto podcast with a colleague at HubSpot at the time, Austin Knight, and we’d spend the majority of our free time talking about all things blockchain. We got the chance to connect with some seriously talented individuals and this helped me get a better understanding of some of the big problems that these projects were going to face in the future.

After the ICO bubble burst and we moved into yet another multi-year crypto winter, it highlighted to me the fragility of the whole space, but I still felt very strongly that some of these early projects would pave the way to web3. At the same time, I didn’t love the idea of moving on from what is an incredible company in HubSpot into a company that could no longer exist in 3 month’s time. Plus, I wasn’t exactly in love with the mission of many of the crypto projects at the time, which was just “make the token price go up”. I was also suffering from imposter syndrome as all of my professional experience was outside of the crypto space.

I figured I’d wait it out. I’ll see how the space evolves and, in the meantime, keep levelling up my skills at HubSpot.

Enter, 2020.

2020 Vision

2020 was the most volatile year of most of our lifetimes. Mine was compounded by the fact that 2 weeks prior to the majority of the world going into a full state of lockdown, my wife gave birth to our first child.

Like most new parents, I was sleep-deprived, stressed, and overwhelmed. The global pandemic removed any external support we were hoping to have from parents and friends – we couldn’t even get postnatal midwife visits. Combine all of this with the fact that financial markets were in turmoil, companies around the world were having to lay off staff, and we had the looming threat of a virus that we knew very little about that was killing hundreds of thousands of people every day… well, it’s fair to say that my introduction to parenthood wasn’t exactly how I had imagined it.

It was a tough year, but in spite of the chaos, it was full of wonderful moments. Not only that but as the year progressed, the markets were rallying. In fact, they were booming. In the background of all this, the crypto space was making a sudden and dramatic revival through what we now refer to as the DeFi summer. Decentralized financial protocols such as Uniswap, Yearn, and Compound had arrived and they sparked a frenzy of new investment. This, combined with the breakout NFT craze that was unfolding, had put crypto, and most notable, web3, back into the mainstream.

A few dots were starting to connect for me. I was fascinated by the composability of different DeFi applications and how NFTs could be used to create whole new online experiences and communities. It was the perfect blend of community building, economics, and emerging technology that led me to go all the way down the rabbit hole once again.

In October of 2021, taking advantage of the generous policy that HubSpot offers to all employees once they reach 5 years of tenure at the company, I took a fully paid sabbatical for a month. Alongside having some much-needed downtime (and playtime with my daughter), I set aside time to figure out what I wanted from the next couple of years.

Being in a leadership position during the pandemic was a lot more mentally challenging than I’d anticipated. Everyone was struggling, and conversations with my team could feel like therapy sessions at times. I didn’t have a great outlet myself and felt horribly burnt out. This was really impacting how happy I was overall and it became obvious to me that I needed to make some changes.

Having Conviction

While I was incredibly thankful for the position I was in at HubSpot, loved my team, and always felt like my contributions were appreciated, I started to realize that my heart wasn’t quite in it anymore. More to the point, all of my spare time was spent thinking about web3. It was new and exciting, and I was loving learning new things again. At the same time, I still had this feeling of imposter syndrome, and while it may not always seem like it from the outside looking in, I’m generally a more risk averse person.

I realized that if I remained risk-off I’d never pursue something I was clearly very passionate about, so I decided to enter 2022 with a greater level of conviction. I started by giving myself more skin in the game. This meant moving a much larger percentage of my cash into crypto, and then actively looking for some advisory positions to get a better sense of how this new wave of decentralized organizations actually operate.

After a couple of months of working on some interesting projects in the GameFi space, I knew this was where I wanted to be. More importantly, I knew I could add value. 

Midway through March, I spoke to the HubSpot leadership team to let them know that I’d be leaving. I didn’t have anything lined up at that point but decided I needed to make the change to figure out what was next. They were incredibly understanding and supportive; yet another sign of what a great group of people they are.

During my notice period, I started getting more and more involved with GameFi company, Decentral Games. They boast the most trafficked venues across all of Decentraland, one of the largest metaverse projects, and have grown a treasury of over $50mm in just 6 months. The team is full of ambitious, hyper-intelligent people who are obsessed with building immersive, enjoyable gaming experiences in the metaverse. Not only that but the whole project is governed by a DAO, meaning that the community has real ownership over the direction it takes.

It’s with great excitement that I can announce that I’m joining the Decentral Games team as Chief Marketing Officer.

As well as being a radically different working environment to what I’m used to, I’ll also be paid exclusively in cryptocurrency. If I was lacking conviction before, the same can’t be said for now. It’s a space I’m passionate about, a project I’m excited to work on, and the shift in my lifestyle that I’ve been searching for.

I’m going all in.

See you in the metaverse 👋