Originally posted on LinkedIn.

There may be no better tell of a VC turned operator turned back to VC than the fact that my last long-form post was about leaving venture capital, this one is about returning to venture capital, and I literally did not write a single blog post in the 4 years in between.

As someone who enjoys writing, I didn’t expect to go dark for that long. I certainly didn’t have a shortage of things to say, but now I recognize why entrepreneurs “go heads down.” It’s not because they don’t want to do the other things, it’s because they need to be constantly — and ruthlessly — prioritizing the greatest and highest value use of their time at all times. For me, that meant personal writing always fell just “below the cut line” while we were in hypergrowth mode at Route.

Going forward, I am grateful that some writing may come back into priority again. A few weeks ago, alongside our Fund IV announcement, we shared that I’m back at Fika Ventures with TX, John, and the rest of the team, most of whom I have known for many, many years. The Fika team’s combination of steadfast values, discipline, work ethic, humility, and results made this a natural choice for me. Just as before, I’ll be investing in B2B marketplaces and software, but now with an earned appreciation for real world supply chain, logistics, and commerce enablement after four years at Route.

It would be hubris to return to venture and immediately share a plethora of opinions, theses on the market, and areas of focus, so I spent my first few quarters back at Fika focused on learning, reintegrating into the community, and looking inwards to the operations of running a fund itself vs rushing back into investing (though I do have one to share soon). There will be plenty of time for hubris in the future :)

When I left VC, I shared that “I felt incomplete, as if there was a great unknown I hadn’t explored.” I didn’t leave with the intention of coming back to VC. I was just in pursuit of that exploration and filling a void that I felt, following my own journey towards an experience that I otherwise would never have had.

THE JOURNEY AT ROUTE

Over the course of the last four years, I was incredibly lucky to live several operator lifetimes in just one operating experience at Route. This is partially due to the overall nature of operating in startups, but I also got “lucky” with my timing — I got to operate through COVID tailwinds and a historic ZIRP growth environment from 2020 to 2022, and then also a major market correction and adapting to a new reality from 2022 onwards. I joined the company at Series A and we went on to achieve incredible hypergrowth metrics across revenue, headcount, and financing. But I’m perhaps most proud of the work that we did after 2022’s market correction.

It would have been easy to ride high on the growth of 2020-’22, but we had to adapt, make hard decisions, innovate, and persevere. Ultimately, the perseverance paid off, Route recently announced a Series C at a $1.4B valuation and, most importantly, that we cleared $100M of collected revenue in 2023 and protected over $15B of merchandise across tens of millions of consumers and thousands of merchants. It’s only grown from there. Route is just scratching the surface of its future empowering eCommerce brands.

During my time as VP, then SVP of Strategy, I got to experience a little bit of everything. For over two years after I joined, we didn’t have a COO or CFO, so I played the role of cross-functional executive while still learning from colleagues and seasoned executives who had clearer ownership (CEO, CRO, CTO, etc.). We still were small enough that I ended up being the individual contributor tackling high priority initiatives but didn’t yet have clear owners. I’d take them on, learn the particular needs of the situation, solve the problem once or twice, then hire people much better suited than myself to build out those particular organizations going forward. Over the years, I had the fortune of working across almost every department in the company while also owning key initiatives along the way. I couldn’t have asked for a better role to suit my unique set of experiences, interests, and skills.

WHY I’M COMING BACK TO INVESTING

So what happened? Why am I coming back to venture? To be honest, I don’t think there is any better vocation for the balance of my skills, interests, and passions. Even while operating, I realized that the things that made me a good operator were the same things that made me a good investor. I love people. I love learning. I love simplifying complex information into approachable structures. I love process. I love authentic relationship building. I love to work (I really, sadly, do. Future post to come about my attempt at a sabbatical). I love building products and companies that people and companies use to improve their lives. I get to maximize on all of this by running a venture fund, and I think it can be quite fun, too.

The unlock for me was to focus all of my efforts around the things that came most effortlessly. For me, these were always about people. Partnerships, fundraising, recruiting, sales, business development, and strategy. They all have people in common.

In venture, you get to strategize your time and focus on the things that you feel uniquely position you for success and returns, but also are simultaneously natural and fulfilling. Because of my genuine appreciation for people and interest in developing relationships with them, I realized that my competitive advantage in venture is greater than it is in operating. I can do the same rewarding work I did as an operator, but do it as an intentional lead investor in three to four companies per year. Rather than raising capital, recruiting, and selling only for Route, I get to raise capital, recruit, and sell for the companies I invest in. And I get the benefit of my own network effects — the things I do to help one company are accretive to another.

WHAT I DID AND DIDN’T LEARN FROM OPERATING

One of the most common questions I get from people is, “What did you learn from operating?” In truth, I learned both a ton and nothing at all. To clarify what may have come across as incredibly pretentious: many of the experiences I had were experiences that I already knew but just hadn’t lived yet. There’s a big difference between being able to say the right thing because you know it and being able to feel it because you lived it. I feel it now.

I don’t think I’ve unlocked some incredible newfound level of human empathy, I’ve just lived it more. I realize how hard it is, how much it can suck, how many trade-offs there are, how it is never ending, how even with every hill you climb and conquer, more hills keep coming. But I also learned how rewarding it can be. How good it feels to climb a hill with a teammate. How great it is to “ship product” and celebrate that. How many friendships are formed. How high the highs are.

While at Route, we raised over $250M. I pitched a lot of investors. My experience was that while there are some wonderful and exceptional people in VC, there are also a lot of duds (I’m too polite to print what I really thought of them). I grew allergic to the number of false promises, platitudes, and occasional disrespect that many investors exhibited. So much of the venture industry is built on overpromises and sales, and not enough is built on integrity and follow-through. This industry holds so much power and influence, yet the bar for kindness, honesty, and respect can be so low that it motivated me to try to do it differently.

I have never had the inner resolve that attached my identity entirely to being a venture investor or an operating executive. I happen to love both, but I am so excited to be recommitted to investing for the long haul. I am thinking in decades now and I see myself in this seat for many years to come, doing what I believe to be the “true work” with entrepreneurs– side-by-side, not across the table.

HOW I’LL OPERATE GOING FORWARD

When I left venture, I shared my reasons for why I was ready to leave. Many of those criticisms still hold true today (saying “no” a lot, long feedback loops, you aren’t ”building,” lack of representation, and more) — but I now see them with more clarity and know how to work towards improving them. I don’t mean this in a macro, “I can change the world and fix all the systemic issues in venture capital” way; I mean this in a personal, introspective way.

I am excited, ready, and intentional about my desire and my reason (“why now”) to do the work. I have clarity on what parts of this industry I love (building a firm with people I respect and learn from, intellectual curiosity, helping people, meeting founders, meeting builders, being a resource) and what parts of it I hate (having to say no most of the time, needing to make judgment calls that have real ramifications on people’s businesses without absolute certainty, superficial networking). I feel equipped with a holistic understanding of this ecosystem to tackle it with my own approach and balance.

And, of course, I feel a little bit nervous! Venture capital has only become more competitive since I left. There are more new funds than ever, and many of them are full of intelligent, hard working, diligent, and excellent people. I intend on doing a lot of work to keep up, but I will follow intellectual curiosity, remain grounded, and seek first party data to support the decisions I make.

In the past, my favorite part of the job was sourcing and deciding which companies to invest in. Now, my favorite part (by far) is supporting companies after I decide to invest.

MY PLEDGE TO FOUNDERS

Investors will never make your business, but they can occasionally break it. Many VCs are so caught up in trying to “add value” that they have the reverse effect: becoming a time suck. While operating is still fresh in my mind, I wanted to write down the type of investor and the type of partner to founders I want to be.

Most importantly, I want to be side-by-side with entrepreneurs, not across the table. Part of why I love early stage investing is because the incentives between investor and founder are more aligned than any other stage. There is always a slight anxiety that comes with having to chat with your lead investor; but I will work tirelessly to reduce that anxiety and make founders feel that I am truly an extension of their team, slack channels, texts, or anything else, rather than a chore to be handled. I believe that relationship equips us to also have hard conversations and see around corners, together.

How will I go about doing that?

• I will never overpromise and underdeliver. No task is too small and I will go above and beyond for founders, but I will never overpromise in order to win a deal. I would rather set expectations low and pleasantly surprise you.
• I’ll operate with transparency. I will always be honest and truthful with you, even if we disagree. I won’t sugar coat, but I will never be rude either. My approach is to share my honest view, with the humility to know that this view is my own, and you will always have a more complete picture to make a decision.
• When it comes to “value add,” my philosophy is that investors can support in areas that we spend more time in, where founders are too busy to prioritize. I have learned to distill this into three categories, all “people-driven”: recruiting, customer development, and fundraising. If I can successfully help you recruit, sell, and raise capital (on top of the capital I invest), I think it’s a fair trade.
• Beyond this, every venture investor will tell you they want to be your thought partner. I, too, feel that way, but I believe I have to earn that right, not buy it. Too many investors think that their capital alone buys them that right; I think I have to earn it by building trust. Trust comes in the form of listening first, asking questions, understanding where and what is actually on your mind, and doing my best to support you in an actionable way.
• Trust also comes, perhaps most importantly, during the hard times. There are plenty of people on the cap table that you want to call when everything is good. There are only a few people you want to confide in when things are extremely challenging. I hope to be one of those people. Someone who has earned enough trust that you want to strategize through hard decisions like hiring, firing, layoffs, sticky capital situations, and anything/everything else.
• I will check in on you. People often say “my door is always open”, but that puts the impetus on the other person to walk through that door. In that vein, I will check in often and ask both about how you are doing on a personal, human level but also how you feel about our working dynamic, how I can improve, and what I can do better.
• I will stay out of your way. While there are many times to tangibly help, I also recognize there are many phases where outside help is not needed and you want to be in execution mode. I will respect that, give you that space to build, and be eager to activate again when the timing is right.

This is a personal approach that I know requires constant effort and maintenance. I hope to live up to my own standards here, but I will lean on founders to keep me honest in this endeavor.

For me, I have finally answered my “why.” I’ve answered all the “what ifs” in the back of my mind. I don’t have any boxes to check or voids to fill. I know why I love this work and I know how I love to do it. This operating journey was never about “completing an arc” for anyone other than myself. It was always a personal endeavor to fill my cup.

That cup is full now, and I’m ready to use that fullness to become an incredible venture investor and to, quite literally, pay it forward.

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