I recently left an amazing job in corporate development to co-found a venture fund. I cut my teeth in corporate development during Facebook’s massive acqui-hire movement, then ran M&A for Dropbox and built the function at Airbnb before shifting into VC to raise a $55M fund.
Over this seven-year journey, I’ve made more than my share of career transformations. Despite the fact that not everyone shares my exact journey, I strongly believe there are a lot of lessons that can be applied to any startup path. I haven’t always known the destination, but I think I stumbled into a solid framework for making informed career decisions that lead to positive outcomes.
How I got Started in Tech
Growing up near Shoreline Amphitheater, I would watch movies right next to the Googleplex, deeply curious about what was going on behind the scenes. Since I didn’t know how to approach tech, I started my career in investment banking. I figured out early on that it wasn’t a great fit for me so I quickly transitioned into venture capital.
Why did I choose venture?
Most people have no basis for comparing one startup to another, and investors learn to make assessments that help serve them down the road. I concluded, “even if I don’t end up loving VC, working in the venture industry will help me develop a decision-making thesis that will help me at any future job I choose.”
As an associate at Menlo Ventures, I realized I wanted to help founders. I had incredible conversations with these really smart individuals but felt like I didn’t have enough wisdom to impart. To cultivate that passion and improve my ability, I looked for roles where I could improve. Few roles in general get to interact with founders as frequently as M&A roles so corporate development was the path I chose.
My Career in Corp Dev
At its core, my role in corp dev was to help founders navigate the M&A journey into a bigger company. I had an incredible experience in the business, growing leaps and bounds through roles at top tech companies:
- In 2011, I was the second person on Facebook’s corp dev team. We closed Instagram and started many other big deals just before Facebook itself went public.
- From Facebook, I transitioned to lead M&A at Dropbox, closing approximately 16 acquisitions over two years.
- Most recently, I built Airbnb’s M&A function from scratch.
My “decision making thesis” from the beginning turned out to be a solid one. The time I spent at Menlo sharpened my ability to evaluate the potential of a startup: as a result, I ended up working at phenomenal companies.
From a work perspective, these experiences taught me everything M&A — from the basic mechanics to a deep understanding of how to build trust with founders. Through my time at companies, however, I always wanted to bring entrepreneurs more value, so VC was always in the back of my mind.
Why I Transitioned out of Corp Dev
Corp dev was a dream job, allowing me the opportunity to work on the toughest, most strategic decisions at great companies. That said, after 30+ acquisitions and thousands more conversations with founders, I started to see diminishing returns on the learning curve – which is my biggest metric for evaluating professional success.
I had to make a choice:
- Double down on being a corp dev exec
- Find something else
The first option would take me to more complex acquisitions at bigger and bigger companies. The second, however, would lead to more learning.
I ultimately realized: If my role at Airbnb was the perfect in-house position for me and I still didn’t feel like I was learning enough, I would never be satisfied by a job as an employee.
That simple realization was enough to inspire my move into VC — and I think anyone can evaluate a similar circumstance.
How I advise others on big career decisions
In general, I believe big career decisions come down to two key points:
- What do you love doing?
- How can you become the best at what you love doing?
What do you love doing?
While it may appear that I orchestrated this path from venture to industry and back, each of my decisions was simply following what I knew I loved. Along the way, I could have discovered I loved products, not founders. You can’t predict your path, so you have to make choices based on what you know at the present moment.
When I was done working at Facebook, I shifted to another company, and then another, I took a seven-year circuitous route, but the whole journey was worth it. Because I was following what I loved, I always felt like I was learning.
How can you become the best at what you love doing?
Whichever path you choose, do the work.
Starting out, I’m fortunate that Facebook took a chance on me. Having never been in the role, I had no idea what I was doing. I was thrust into a position where I was leading and closing deals. Fortunately, I had an amazing manager and support network that saw I was trying hard.
Since they knew I cared, they helped set me up for success.
Where I ended up: Wave Capital
I’ve helped founders from all different perspectives, and now it’s come full circle: I’m a co-founder at Wave Capital. As my Partners and I continue to work with founders while also learning the ropes myself, I have even more empathy for the ups and downs that come with the territory.
I plan (and hope) to impact founders in many ways, but there are three that stand out:
Working in M&A, I saw many founders arrive at the end of their journey so diluted by fundraising that they were no longer incentivized to build a great company. Now, Wave helps founders craft the right size investment upfront to ideally take them all the way to their Series A (and avoid taking more dilution in subsequent seed financings). This also aligns our incentives with the founders, so we’re all interested in building the best business possible.
Even if documents are technically done overnight, relationships are built over time. I’ve found the best experiences have come from working with the very best people, which take time to cultivate. And it’s when there’s a relationship rooted in trust that both M&A and VC partners are more likely to say yes.
I recommend tip-toeing into relationships. It’s an approach I also used in choosing to partner with my two co-founders at Wave and one that I think translates into all partnerships (M&A, venture, and others).
Educate from an unfair position
Corp dev and VCs negotiate all the time, which makes the dynamic unfair for founders. At Wave, I get to help founders navigate these difficult situations.
For example, my experience shows me the most effective negotiation tactics are rooted in honesty and trust. If you jockey or offer exploding terms, M&A or VCs can read through your posturing. And once you mislead, you lose their trust.
In M&A specifically, there’s a misconception that it’s good to overplay your hand. In my experience, it usually backfires.
You don’t know what you don’t know. By focusing on what you do know, you can make informed career decisions that ultimately take you to a place where it all comes together.
After a seven-year journey, I’m glad to be back at VC, where I focus exclusively on helping founders. Whenever I hit a transition point, I return to what drives me — which in my case is working with founders.
For anyone getting the itch to try something different, I encourage you to ask yourself these questions.
Photo credit: Career Contessa