Saying Goodbye to a Good Thing

Saying Goodbye to a Good Thing

May 24, 2021

I joined Bowery Capital in January 2020 to get a crash course in venture capital and seed-stage startups in hopes of one day becoming a founder myself. Little did I know I'd be doing it in the middle of a global pandemic, which created some opportunities (easier to observe a board meeting over Zoom) but also challenges (I haven't seen one of our partners IRL since meeting in the interview process). The last year and a half has been an incredibly positive experience, and it’s with mixed emotions that I'll be leaving Bowery and giving up a role that has been the highlight of my career to date. It's hard to say goodbye to a good thing, and I'll certainly miss getting to spend every day working with one of my close friends surrounded by founders and investors I admire. While I didn't expect to move on this soon, there's a lot to be thankful for when looking back on these past 18 months. From getting to work with our founders on hundreds of projects to helping put on Accelerate 2020 (our pre-seed B2B GTM accelerator) and the BC Marketing Summit, I've gotten the chance to learn and grow every step of the way. As I think about the best way to articulate all of my experiences at Bowery, three main themes emerge: exposure, network, and team/culture. I'll dig into each a bit more below:


Exposure

Before coming into this role, I spent three and a half years going really deep at one startup. I knew our industry front to back, I knew every nook and cranny of our GTM motion, I knew the complexities and nuances of our product, and I had gotten to know the culture and operating style of our team. I essentially had one very detailed data point on how startups work. One of the main goals joining Bowery was to increase the number of data points and get some of this exposure across a variety of companies, especially on the GTM side. This was hands down one of my favorite aspects of the role - getting broad exposure across an array of companies, founders, business models, GTM motions, company stages, industries, and situations. Not only did I get to see the board decks, operating models, fundraising decks, sales/GTM playbooks, hiring plans, etc., but in many cases I actually got to partner with founders to help create or refine them. On the go-to-market side of things (my main area of focus), it has been a fun challenge to work on so many different GTM strategies across the portfolio for different ICPs, buyer personas, price points, and types of solutions. It truly felt like an accelerated founder bootcamp getting to see so many companies and founders in parallel.

In addition to the exposure to founders and startups, there was also a huge learning curve on the investing side. Getting to join and participate in every Investment Committee Meeting was a completely new side of the startup world I had never been exposed to previously. How investors think about and evaluate new companies, what gets them excited, what gets companies dinged, how does the perception of the investor change based on XYZ factors, what happens in a competitive investment process, how to perform due diligence, what happens in follow-on bridge rounds, what makes a company successful/unsuccessful in the next round raise, what happens when a company fails to raise, and the list goes on - these are all questions I was clueless about before joining Bowery.

Network

Before joining Bowery, I only knew three founders personally - my startup's CEO, a buddy from college and another founder he introduced me to while I was living in Hong Kong. I knew a few CROs (all former bosses of mine), two marketing execs (all from that same startup), and a couple of customer success leaders (you guessed it, from the same startup). My network was, shall we say, limited...I didn't realize it at the time, though - I was meeting tons of people, mostly from the travel industry we were operating in. But these weren't the right people for me to call if I was going to be a founder trying to solve founder problems. For comparison, I've now been lucky enough to meet literally hundreds of founders and revenue leaders through Bowery pitches and portfolio companies, various accelerators/incubators, hosting our podcast, and general networking with Bowery friendlies and the broader global startup community. Some of these people run companies you've never heard of, others have built businesses that are household names. I remember when I was starting my first job out of college at JPMorgan, Jamie Dimon spoke to our analyst class and said something along the lines of, "There are two primary ways to learn: reading and talking to people. Talking to people is much faster." This couldn't be more true, and having the opportunity to build up such an extensive network of founders and revenue leaders has been the fastest way for me to learn the ins and outs of building companies.

Team/Culture

I knew when joining Bowery the team was best-in-class, but I don't think I fully appreciated how humble, open-minded, and supportive they'd be. I often found myself on the receiving end of "WDYT" questions on topics where they knew way more than me. When I'd bring a bad idea to the table, they'd let me know, and when I came with a good one, they were 100% behind me and eager to help.

It's a small but mighty group with only four people on the core team, and the culture is such that the team puts full trust in one another to own their respective areas of expertise. Whether it's spinning up a new offering for founders, launching a new content series, creating a new founder event, exploring new partnerships, building new initiatives to increase diversity of deal flow, focusing on a new sector, theme, or geography - this role offered me quite a bit of creativity to invest time in what I thought was most important. For me, this level of trust and autonomy has been the perfect training ground for what's to come, as there isn't a step-by-step playbook for what to do each day when building a company.


Truth be told, I actually tried removing myself from the interview process when I was first exploring this role. I had a lot going on personally - I had just gotten married, moved across the country to Seattle, and was recovering from a major surgery. Mike Brown called me and told me I should see the process through, emphasizing that this is an incredible and rare opportunity and that it'd be a big accelerator for my career. I've had a few life-changing phone calls in my life, and that was certainly one of them. I couldn't be more grateful for that call and all of the opportunities Bowery has provided since. As you can tell, it's not an easy decision to give all of this up, especially getting to do it with such an awesome group of people.

Reach out if any of this resonates as we're hiring my replacement ASAP!

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