Reflecting on Year 1 in Venture
August marks the anniversary of my first * official * year at Flybridge. I sometimes find professional reflection posts slightly self indulgent. But, the one year milestone is a nice moment to pause and take stock, so here we go.
My journey to Flybridge started in 2016, when I crossed paths with Jesse Middleton while we were both working at WeWork. In 2019, after Jesse had joined as a partner at Flybridge, I very intentionally used Jesse as my wedge (sorry Jesse) to meet Flybridge cofounder Chip Hazard and secure an internship with XFactor — a Flybridge Network Fund — while completing my MBA at Wharton.
It feels wrong to say I was lucky that COVID made the bulk of my business school experience remote. But, the virtual MBA enabled me to devote a ton of time to XFactor — taking dozens and dozens of founder calls back-to-back between classes. (Also, had I not gone to business school when I did, I would have been at WeWork during their first IPO debacle, so yeah, silver linings).
Interning with XFactor was very much a deliberate maneuver — or so I hoped — to start working with the broader Flybridge team. I was luckily able to pull this off, which gave me a chance to get to know the other partners, Jeff and Anna, which eventually led to an offer to join Flybridge full-time after graduation.
When I talk to young professionals looking to “break into venture”, beyond the standard advice, I usually share that once you land an internship, just focus on doing a really good job. It doesn’t matter how “small” the engagement may seem — it could be an hour a week, making a market map, or doing some part-time research. Try to “land and expand” versus jumping from internship to internship early in your venture journey. Small caveat — if you’re testing out investment stages, geos, sectors, culture, etc. the “jumping around” approach makes sense. But if you find someplace you really like (which admittedly is rare) all efforts should be reoriented to doing an amazing job. To my current MBAs — I promise, the ROI of this is higher than joining another venture club and organizing lunch-and-learns.
So, now that I’m one year in to doing the actual job, what have I learned? Just the tip of iceberg, but three things:
First, send “hail mary” emails. I reach out to people I have no business contacting on a weekly basis (see below). While AirBnB’s CEO denied my pursuits to connect, you’d be surprised with how often these flyers work out. My email to Wharton’s dean with the subject line, “Giving this a try…” got my foot in the door for acceptance. The internet is a wonderful place where — with a well crafted cold email — you can connect with most people.
Second, treat people well. This doesn’t just mean founders and investors you meet in an “official” capacity. It also includes the doorman of your office building, the restaurant hostess, and maybe even the random person you match with on a dating app. (I have literally pinged an old Bumble match for diligence on a deal we ended up investing in, and he was happy to help out.) The world is a very, very small place — especially New York — and people are connected in ways that will surprise you. Act with integrity, and be mindful about the self perception you’re cultivating.
(please disregard grammatical errors)
Third, create opportunities for serendipity. This one’s a bit harder to describe how to enact. But, I’m a firm believer in putting things into the ether, and seeing what comes back. As an example, when I started at Flybridge, I created a TikTok account for our firm. My initial motivation here was to learn more about the content creation process and TikTok viewership analytics, because Flybridge invests in creator economy infrastructure. But, the account has led to meeting dozens of founders, operators, investors, friends, and even reporters, which recently led to a small feature in TechCrunch. TLDR — you never know where you’re going to meet that next, amazing CEO, so try to create space for serendipity. (Another caveat here — there is a limit. There is always another founder meeting to take, dinner to attend, blog post to write, etc. Feelings of FOMO in early stage venture are very real, and can become a bit crippling. Set clear parameters for yourself around how you can “put yourself out there” in a consistent and sustainable way.)
These lessons don’t even scratch the surface of all the takeaways from my first year in venture. I couldn’t be more excited to be heading into year two (as a newly minted Principal…there I said it) with the Flybridge team. Looking forward to many more learnings and years ahead.
